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Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

101 Mulberry St, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$945,000

Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor primary suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor with 4 additional guest bedrooms and bath. This renovated home also has a separate 3 bay garage with a 2-bedroom 2-bath water view apartment with a nice open living and dining area and total square footage of 768. The main house has an attached 1 bedroom 1 bath in-law suite. Great space for your guests or potential for a vacation rental. A nice wide-open lawn leads you to the dock with 7 boat slips. Right on the Knapps Narrows. Tilghman is the perfect place to start making your Eastern Shore Memories. New pictures to come...

5 Beds ⋅ 2 Baths

Located minutes from St. Michaels this waterfront property is a boater's dream. Tilghman, is a small island big on history, nature and local lore. Situated just over the Knapps Narrows Bridge this home offers a main house with first floor primary suite. The first floor is open with custom details and just perfect for hosting friends and family. A custom spiral staircase leads to a second floor with 4 additional guest bedrooms and bath. This renovated home also has a separate 3 bay garage with a 2-bedroom 2-bath water view apartment with a nice open living and dining area and total square footage of 768. The main house has an attached 1 bedroom 1 bath in-law suite. Great space for your guests or potential for a vacation rental. A nice wide-open lawn leads you to the dock with 7 boat slips. Right on the Knapps Narrows. Tilghman is the perfect place to start making your Eastern Shore Memories. New pictures to come...

21552 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$449,000

The perfect renovated, water view cottage, dating back to circa 1890. Has been meticulously maintained and thoughtfully expanded over the years. Located in the waterfront Village of Neavitt (+/- 70 homes). Move-in mint condition with numerous recent upgrades. First floor primary bedroom, first floor renovated full bathroom, two additional bedrooms and full bathroom upstairs. Outdoor Living: A large screened porch and deck extend the living space outdoors, providing opportunities to enjoy views of the large backyard and breezes off the water. Detached garage/shed with electric for storage of boats in addition to space for a workshop. Solar panels on roof are owned and convey. They substantially lower electric cost to heat and cool the home. Only about 12 miles from the shops and restaurants of charming St Michaels but without St. Michael's town taxes. The village has its own park and playground as well as a public landing with a launch for canoes and kayaks. While currently on a septic system, public sewer is in the process of servicing the town, adding convenience and potentially increasing property value. Overall, this Eastern Shore retreat offers a blend of historical character, modern updates, and a desirable water view location, making it suitable for both full-time residence or part-time retreat. County sewer soon available. Neavitt yard sale moved to September while other village get-togethers/activities remain as scheduled.

The perfect renovated, water view cottage, dating back to circa 1890. Has been meticulously maintained and thoughtfully expanded over the years. Located in the waterfront Village of Neavitt (+/- 70 homes). Move-in mint condition with numerous recent upgrades. First floor primary bedroom, first floor renovated full bathroom, two additional bedrooms and full bathroom upstairs. Outdoor Living: A large screened porch and deck extend the living space outdoors, providing opportunities to enjoy views of the large backyard and breezes off the water. Detached garage/shed with electric for storage of boats in addition to space for a workshop. Solar panels on roof are owned and convey. They substantially lower electric cost to heat and cool the home. Only about 12 miles from the shops and restaurants of charming St Michaels but without St. Michael's town taxes. The village has its own park and playground as well as a public landing with a launch for canoes and kayaks. While currently on a septic system, public sewer is in the process of servicing the town, adding convenience and potentially increasing property value. Overall, this Eastern Shore retreat offers a blend of historical character, modern updates, and a desirable water view location, making it suitable for both full-time residence or part-time retreat. County sewer soon available. Neavitt yard sale moved to September while other village get-togethers/activities remain as scheduled.

6390 Bozman Neavitt Rd, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$899,000

The opportunities abound for this waterfront home overlooking the Knapps Narrows. Formally, Maynard Lowery's boat building business, this residentially zoned, single-family home comes with 5 boat slips and unlimited possibilities. Can be easily expanded up to 6 bedrooms and 4 baths. The first level would make an ideal hobby area or additional living area. Handicap Accessible with elevator. Commercial potential.

2 Beds ⋅ 3 Baths

The opportunities abound for this waterfront home overlooking the Knapps Narrows. Formally, Maynard Lowery's boat building business, this residentially zoned, single-family home comes with 5 boat slips and unlimited possibilities. Can be easily expanded up to 6 bedrooms and 4 baths. The first level would make an ideal hobby area or additional living area. Handicap Accessible with elevator. Commercial potential.

21572 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$845,000

Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

21560 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$799,000

📍Luxury resort-style living in the prestigious waterfront community of Easton Village! This spacious 4-bedroom, 3.5-bath home features a rare dual primary suite layout—with options on both the first and second floors—complemented by a $5,000 seller allowance to choose your own brand-new flooring. 📍The light-filled interior has been freshly painted throughout and features a versatile sunroom/office space that flows seamlessly off the main living area. Cooking and entertaining are a breeze in the gourmet kitchen, which boasts quartz countertops, a butler's pantry, and a brand-new built-in dishwasher. Retreat to the first-floor primary suite, which features an upgraded Safe Step hydrotherapy spa tub—perfect for relaxing muscles and ultimate comfort. 📍The premium upgrades continue outdoors. Enjoy low-maintenance luxury on both the welcoming front porch and the private side porch, both fully updated with durable, long-lasting Trex® decking. 📍The large, enclosed backyard offers the ultimate private retreat, beautifully framed by premium, durable HardiePlank® siding on the exterior. Additional unique features include a cozy gas fireplace and a rare 2-car garage with a heated and cooled third-bay workshop—perfect for hobbies or extra storage. 📍Live the ultimate Eastern Shore lifestyle with community access to scenic trails, boat slips, a pool, a fitness center, and a clubhouse, all just minutes from downtown Easton.

4 Beds ⋅ 4 Baths

📍Luxury resort-style living in the prestigious waterfront community of Easton Village! This spacious 4-bedroom, 3.5-bath home features a rare dual primary suite layout—with options on both the first and second floors—complemented by a $5,000 seller allowance to choose your own brand-new flooring. 📍The light-filled interior has been freshly painted throughout and features a versatile sunroom/office space that flows seamlessly off the main living area. Cooking and entertaining are a breeze in the gourmet kitchen, which boasts quartz countertops, a butler's pantry, and a brand-new built-in dishwasher. Retreat to the first-floor primary suite, which features an upgraded Safe Step hydrotherapy spa tub—perfect for relaxing muscles and ultimate comfort. 📍The premium upgrades continue outdoors. Enjoy low-maintenance luxury on both the welcoming front porch and the private side porch, both fully updated with durable, long-lasting Trex® decking. 📍The large, enclosed backyard offers the ultimate private retreat, beautifully framed by premium, durable HardiePlank® siding on the exterior. Additional unique features include a cozy gas fireplace and a rare 2-car garage with a heated and cooled third-bay workshop—perfect for hobbies or extra storage. 📍Live the ultimate Eastern Shore lifestyle with community access to scenic trails, boat slips, a pool, a fitness center, and a clubhouse, all just minutes from downtown Easton.

8050 Easton Village Dr, Easton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$1,685,000

UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

5 Beds ⋅ 5 Baths

UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

9180 Saint Michaels, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$515,000

Just 12 miles from St Michaels, this house is in a quiet community of 60+ homes at the end of a lovely peninsula. A public landing is at the end of Bozman Neavitt Road, and a community center and park are in the heart of the village. This property has been renovated and updated from the studs out. Features now include 2-3 Bedrooms 2 Full baths Living room with built-ins Light-filled kitchen with cathedral ceiling Large landscaped lot with patio A Short-term Rental application is underway. Ask owner for details. Some furniture conveys

2 Beds ⋅ 2 Baths

Just 12 miles from St Michaels, this house is in a quiet community of 60+ homes at the end of a lovely peninsula. A public landing is at the end of Bozman Neavitt Road, and a community center and park are in the heart of the village. This property has been renovated and updated from the studs out. Features now include 2-3 Bedrooms 2 Full baths Living room with built-ins Light-filled kitchen with cathedral ceiling Large landscaped lot with patio A Short-term Rental application is underway. Ask owner for details. Some furniture conveys

6394 Bozman Neavitt Rd, Neavitt

Listing courtesy of TTR Sotheby's International Realty. Contact:

$399,900

Set on nearly an acre in the heart of Wittman, this cedar shake–sided home offers space, character, and a relaxed Eastern Shore lifestyle. Built in 1900, the 3-bedroom, 1.5-bath residence blends timeless charm with thoughtful updates for comfortable everyday living. Hardwood flooring runs throughout, complemented by a sun-filled dining room and a cozy living room with a gas fireplace and built-in shelving. The kitchen has been refreshed with new flooring, afarmhouse sink, updated butcher block countertops, and a new refrigerator—bright, functional, and well-suited for daily life while preserving the home’s original character. Outdoors, the spacious 0.86-acre lot is dotted with mature trees and beautiful landscaping, offering plenty of room to add a deck or fence. A covered front porch and outdoor shower enhance the home’s easygoing coastal feel. An oversized two-car garage with attic storage and a large driveway provide ample parking and storage. Located just 0.1 miles from Wittman Community Park, 0.3 miles from Wittman Wharf, and only 7 miles from historic downtown St. Michaels, this property offers peaceful small-town living with convenient access to waterfront amenities, dining, and shopping. A rare opportunity to enjoy space, charm, and location on Maryland’s Eastern Shore.

Set on nearly an acre in the heart of Wittman, this cedar shake–sided home offers space, character, and a relaxed Eastern Shore lifestyle. Built in 1900, the 3-bedroom, 1.5-bath residence blends timeless charm with thoughtful updates for comfortable everyday living. Hardwood flooring runs throughout, complemented by a sun-filled dining room and a cozy living room with a gas fireplace and built-in shelving. The kitchen has been refreshed with new flooring, afarmhouse sink, updated butcher block countertops, and a new refrigerator—bright, functional, and well-suited for daily life while preserving the home’s original character. Outdoors, the spacious 0.86-acre lot is dotted with mature trees and beautiful landscaping, offering plenty of room to add a deck or fence. A covered front porch and outdoor shower enhance the home’s easygoing coastal feel. An oversized two-car garage with attic storage and a large driveway provide ample parking and storage. Located just 0.1 miles from Wittman Community Park, 0.3 miles from Wittman Wharf, and only 7 miles from historic downtown St. Michaels, this property offers peaceful small-town living with convenient access to waterfront amenities, dining, and shopping. A rare opportunity to enjoy space, charm, and location on Maryland’s Eastern Shore.

22582 Pot Pie Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$450,000

Rare opportunity: Updated ranch-style home offering 3 bedrooms and 2 full baths, including a private primary suite, set on a semi-private property on Maryland’s Eastern Shore. The sale includes an additional separate 1.55-acre lot (Tax ID: 2101039261), providing added space and privacy for a total of 2.41 acres. The upgraded kitchen features updated countertops, cabinetry, appliances, flooring, and modern lighting, while updated flooring extends throughout most of the main level. A wood-burning fireplace anchors the additional living space. The primary suite and second bedroom both include walk-in closets, and both full bathrooms have been tastefully updated. Enjoy year-round comfort and efficiency with a recently replaced HVAC system featuring energy-saving geothermal technology. A large sunroom and exterior deck overlook the wooded backyard, offering the perfect setting to relax and enjoy the natural surroundings. The property also features a 12x24 shed for additional storage, a LeafGuard gutter system with transferable warranty, and a separate forced-air propane furnace in the garage for added comfort during colder months. A 2-car attached garage completes the home’s features. Experience rural living with beautiful mature trees and privacy, all just minutes from Easton’s shopping, dining, and local amenities.

Rare opportunity: Updated ranch-style home offering 3 bedrooms and 2 full baths, including a private primary suite, set on a semi-private property on Maryland’s Eastern Shore. The sale includes an additional separate 1.55-acre lot (Tax ID: 2101039261), providing added space and privacy for a total of 2.41 acres. The upgraded kitchen features updated countertops, cabinetry, appliances, flooring, and modern lighting, while updated flooring extends throughout most of the main level. A wood-burning fireplace anchors the additional living space. The primary suite and second bedroom both include walk-in closets, and both full bathrooms have been tastefully updated. Enjoy year-round comfort and efficiency with a recently replaced HVAC system featuring energy-saving geothermal technology. A large sunroom and exterior deck overlook the wooded backyard, offering the perfect setting to relax and enjoy the natural surroundings. The property also features a 12x24 shed for additional storage, a LeafGuard gutter system with transferable warranty, and a separate forced-air propane furnace in the garage for added comfort during colder months. A 2-car attached garage completes the home’s features. Experience rural living with beautiful mature trees and privacy, all just minutes from Easton’s shopping, dining, and local amenities.

8953 Treesdale Dr, Easton

Listing courtesy of Keller Williams Flagship. Contact:

$425,000

Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced backyard with a 6‑ft wood privacy fence, creating an ideal space for outdoor living, pets, or quiet relaxation. Inside, the home presents like new with thoughtful upgrades throughout, including hardwood flooring, recessed lighting & fresh interior paint. The kitchen and bathrooms shine with quartz countertops, tile flooring, and modern finishes. The kitchen is equipped with stainless steel appliances, new cabinetry, quartz countertops, and an under‑sink water filtration system. A front‑loading Samsung washer and dryer and a 50‑gallon water heater add to the home’s move‑in‑ready appeal. Offering 3 bedrooms and 2 full bathrooms, this well‑designed floor plan provides comfortable single‑floor living in one of the Eastern Shore’s most desirable towns. Whether you’re seeking a full‑time residence, a weekend retreat, or an investment opportunity, this St. Michaels gem delivers style, convenience, and exceptional value. The driveway access is on N Talbot St. Please see agent remarks. Try before you buy with a minimum 4-month lease. Please see rental listing! Seller may accept an offer at any time without notice.

Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced backyard with a 6‑ft wood privacy fence, creating an ideal space for outdoor living, pets, or quiet relaxation. Inside, the home presents like new with thoughtful upgrades throughout, including hardwood flooring, recessed lighting & fresh interior paint. The kitchen and bathrooms shine with quartz countertops, tile flooring, and modern finishes. The kitchen is equipped with stainless steel appliances, new cabinetry, quartz countertops, and an under‑sink water filtration system. A front‑loading Samsung washer and dryer and a 50‑gallon water heater add to the home’s move‑in‑ready appeal. Offering 3 bedrooms and 2 full bathrooms, this well‑designed floor plan provides comfortable single‑floor living in one of the Eastern Shore’s most desirable towns. Whether you’re seeking a full‑time residence, a weekend retreat, or an investment opportunity, this St. Michaels gem delivers style, convenience, and exceptional value. The driveway access is on N Talbot St. Please see agent remarks. Try before you buy with a minimum 4-month lease. Please see rental listing! Seller may accept an offer at any time without notice.

101 Brooks Ln, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$414,900

Charming Victorian in Historic Easton! This unique single-family home offers the perfect blend of modern style and classic early-1900s character. Featuring 4 bedrooms and 2 fully renovated full baths, this multi-level home showcases timeless architectural details including two fireplaces, a welcoming large front porch, and original/rebuilt single-pane wood windows across the front that preserve its historic charm. Inside, enjoy an open-concept layout with a spacious living room, dining room, and kitchen—ideal for entertaining. Step right out from the dining area onto a huge rear deck, perfect for outdoor gatherings and relaxing evenings. While the home offers a modern feel with historic touches, it does require additional work and will not qualify for standard financing. Ideal opportunity for an investor or buyer looking to restore and build equity in one of Easton’s most desirable historic areas on Maryland’s Eastern Shore.

Charming Victorian in Historic Easton! This unique single-family home offers the perfect blend of modern style and classic early-1900s character. Featuring 4 bedrooms and 2 fully renovated full baths, this multi-level home showcases timeless architectural details including two fireplaces, a welcoming large front porch, and original/rebuilt single-pane wood windows across the front that preserve its historic charm. Inside, enjoy an open-concept layout with a spacious living room, dining room, and kitchen—ideal for entertaining. Step right out from the dining area onto a huge rear deck, perfect for outdoor gatherings and relaxing evenings. While the home offers a modern feel with historic touches, it does require additional work and will not qualify for standard financing. Ideal opportunity for an investor or buyer looking to restore and build equity in one of Easton’s most desirable historic areas on Maryland’s Eastern Shore.

101 Chapel Rd, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: howardcounty@penfedrealty.com

$2,500,000

Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access.

5 Beds ⋅ 1 Baths

Discover one of Talbot County’s rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72-acre agricultural property features approximately 80± acres of tillable ground and is well suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature hardwoods and softwoods, including pine and oak, providing privacy, scenic beauty, and excellent wildlife habitat. The property is zoned agricultural, offering flexibility for farming, recreation, or investment use. Property is being offered in cooperation with Casey Kennedy and Whitetail Properties. The tillable acreage carries an overall NCCPI rating of approximately 57.3, indicating solid, productive ground suitable for row crops, small grains, and conservation programs. The farm boasts over 2,500 feet of water frontage on Miles Creek, offering excellent duck and goose hunting opportunities. The property is located on a known migratory flyway for ducks and geese along the Chesapeake Bay, making it a proven waterfowl destination. A network of trails through the wooded areas leads to a cleared waterfront area on Miles Creek featuring a dock and picnic table, ideal for family activities, swimming, and fishing. A small point along the creek includes a strategically placed booby blind, positioned for effective duck and goose hunting. Additional amenities include multiple duck blinds on Miles Creek and a goose pit. The historic two-story farmhouse, dating to the early 1900s, offers five bedrooms and one full bathroom and features a new roof and siding. Beginning with the main floor, the home offers a large living room, dining room, kitchen, and the first of five bedrooms. The second floor includes four large bedrooms and a full bath. The residence is accessed by a private driveway off Saulsbury Road, providing convenient access while maintaining a high level of privacy. A small shed next to the home provides additional storage. This property is income-producing, with revenue potential from farming operations, CRP enrollment, and hunting leases, making it a versatile investment opportunity, productive farm, or private recreational retreat with waterfront access.

4108 Saulsbury Rd, Trappe

Listing courtesy of VYBE Realty. Contact: 4102204648

$489,990

Ideally located in a prime cul-de-sac, this main level living home showcases a sophisticated interior with artisan trim and impressive 10-foot ceilings throughout. The welcoming covered entry leads you to the heart of the home: a spacious family room open to a chef-inspired kitchen and a comfortable dining area. The kitchen is a highlight, featuring a substantial island, abundant white cabinets, Carrara Morro quartz countertops, a gourmet stainless steel appliance package with range hood, and a large walk-in pantry. Extend your living space to the rear screened porch, accessible from the family room and dining room. A dedicated study offers a quiet sanctuary for work or hobbies. The primary suite offers a private retreat with dual walk-in closets and a deluxe primary en suite bathroom featuring a soaking tub. The opposite wing houses two secondary bedrooms and a full bathroom. A well-appointed laundry room with a sink, conveniently located off the two-car garage, also functions as a practical mudroom. Located in Lakeside at Trappe, a vibrant lakeside community with a plethora of amenities and ideally located on Maryland's Eastern Shore. Lakeside at Trappe is a private retreat to live, work, and play all in one place. Community currently offers a pool, bathhouse with fitness room, ping pong, corn hole and Bark park, playground and racquet sports courts. An immersive lakeside experience also in the works! Ask about special fixed rate financing and closing costs!

Ideally located in a prime cul-de-sac, this main level living home showcases a sophisticated interior with artisan trim and impressive 10-foot ceilings throughout. The welcoming covered entry leads you to the heart of the home: a spacious family room open to a chef-inspired kitchen and a comfortable dining area. The kitchen is a highlight, featuring a substantial island, abundant white cabinets, Carrara Morro quartz countertops, a gourmet stainless steel appliance package with range hood, and a large walk-in pantry. Extend your living space to the rear screened porch, accessible from the family room and dining room. A dedicated study offers a quiet sanctuary for work or hobbies. The primary suite offers a private retreat with dual walk-in closets and a deluxe primary en suite bathroom featuring a soaking tub. The opposite wing houses two secondary bedrooms and a full bathroom. A well-appointed laundry room with a sink, conveniently located off the two-car garage, also functions as a practical mudroom. Located in Lakeside at Trappe, a vibrant lakeside community with a plethora of amenities and ideally located on Maryland's Eastern Shore. Lakeside at Trappe is a private retreat to live, work, and play all in one place. Community currently offers a pool, bathhouse with fitness room, ping pong, corn hole and Bark park, playground and racquet sports courts. An immersive lakeside experience also in the works! Ask about special fixed rate financing and closing costs!

1549 Lake Tahoe Dr, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322

$564,000

TILGHMAN ISLAND. Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite countertops, stylish modern appliances, a large center island, and an oversized walk-in pantry—perfect for both everyday cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, where a stunning gas fireplace creates a warm and inviting atmosphere for daily living and special gatherings. Upstairs, you will find a thoughtfully designed layout offering comfort and privacy. The expansive primary suite is a true retreat, complete with two separate walk-in closets and a luxurious en-suite bath. An additional generously sized ensuite bedroom provides excellent flexibility for family or guests, while the remaining bedrooms offer ample space and versatility for a home office, gym, or guest accommodations. Situated in the tranquil Tilghman on Chesapeake community, residents enjoy access to exceptional amenities, including a community pool, clubhouse, and deep-water boat slips available through the HOA. Ideally located near the Chesapeake Bay and surrounding tributaries, this home offers unparalleled access to boating, deep-water fishing, crabbing, and scenic coastal adventures. Miles of open bike trails and the peaceful charm of Tilghman Island complete the experience, making this property the perfect blend of luxury, comfort, and true Bay living.

5 Beds ⋅ 4 Baths

TILGHMAN ISLAND. Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout. The gourmet kitchen is a true centerpiece, featuring granite countertops, stylish modern appliances, a large center island, and an oversized walk-in pantry—perfect for both everyday cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, where a stunning gas fireplace creates a warm and inviting atmosphere for daily living and special gatherings. Upstairs, you will find a thoughtfully designed layout offering comfort and privacy. The expansive primary suite is a true retreat, complete with two separate walk-in closets and a luxurious en-suite bath. An additional generously sized ensuite bedroom provides excellent flexibility for family or guests, while the remaining bedrooms offer ample space and versatility for a home office, gym, or guest accommodations. Situated in the tranquil Tilghman on Chesapeake community, residents enjoy access to exceptional amenities, including a community pool, clubhouse, and deep-water boat slips available through the HOA. Ideally located near the Chesapeake Bay and surrounding tributaries, this home offers unparalleled access to boating, deep-water fishing, crabbing, and scenic coastal adventures. Miles of open bike trails and the peaceful charm of Tilghman Island complete the experience, making this property the perfect blend of luxury, comfort, and true Bay living.

5559 Trafalgar Cir, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166

$11,000,000

Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is the Tidewater Colonial Main Residence, meticulously renovated in 2025. Blending Coastal Charm with modern luxury, the home features: Gourmet Kitchen, equipped with custom cabinetry and top-tier luxury appliances. Waterfront Great Room, an architectural masterpiece with floor-to-ceiling glass offering expansive views of the Chesapeake Bay. Owner’s Wing, a first-floor primary suite featuring dual bathrooms and dual walk-in closets. Refined Finishes: Time-period hardwood flooring throughout, four brick wood-burning fireplaces, and durable HardiePlank siding with a metal roof. Outdoor Living: A tree-lined drive leads to a resort-style grounds featuring a swimming pool, pool house, built-in hot tub, and dedicated pickleball and basketball courts. Estate Infrastructure: 3-car garage, geothermal heating, backup generator, professional hardscaping and multiple barns and storage buildings . Additional Housing: The compound includes three private guest houses and a dedicated caretaker’s residence . The Land & Conservation: Comprised of five distinct parcels, the acreage is a diverse blend of productive agriculture and natural sanctuary. Acreage Breakdown: 390+/- acres of fertile, income-producing cropland and 175+/- acres of mature forest. Waterfowl & Wildlife: A premier destination for sportsmen, the property includes a 7+ acre stocked fishpond/waterfowl holding and six well-fed, water-controlled waterfowl impoundments designed for quality game management. Shoreline & Pier: Over 1,200 feet of shoreline revetment protects the coast. The private pier is equipped with two boat lifts and additional mooring capacity. Middleville is a "turn-key" legacy estate on Maryland’s Eastern Shore, offering a rare fusion of historic significance, 2025 modern luxury, and vast natural resources. In an era where land is the ultimate luxury, this is a unique opportunity to secure one of the region's most significant holdings.

4 Beds ⋅ 5 Baths

Presenting "Middleville" (est. 1880), one of the largest waterfront farm and residential estates currently available in the State of Maryland. Spanning over 662 pristine acres in Talbot County, this once-in-a-lifetime landholding features 1.8 miles of shoreline and a world-class infrastructure for luxury living and elite conservation. The Residences & Amenities: The centerpiece of the Estate is the Tidewater Colonial Main Residence, meticulously renovated in 2025. Blending Coastal Charm with modern luxury, the home features: Gourmet Kitchen, equipped with custom cabinetry and top-tier luxury appliances. Waterfront Great Room, an architectural masterpiece with floor-to-ceiling glass offering expansive views of the Chesapeake Bay. Owner’s Wing, a first-floor primary suite featuring dual bathrooms and dual walk-in closets. Refined Finishes: Time-period hardwood flooring throughout, four brick wood-burning fireplaces, and durable HardiePlank siding with a metal roof. Outdoor Living: A tree-lined drive leads to a resort-style grounds featuring a swimming pool, pool house, built-in hot tub, and dedicated pickleball and basketball courts. Estate Infrastructure: 3-car garage, geothermal heating, backup generator, professional hardscaping and multiple barns and storage buildings . Additional Housing: The compound includes three private guest houses and a dedicated caretaker’s residence . The Land & Conservation: Comprised of five distinct parcels, the acreage is a diverse blend of productive agriculture and natural sanctuary. Acreage Breakdown: 390+/- acres of fertile, income-producing cropland and 175+/- acres of mature forest. Waterfowl & Wildlife: A premier destination for sportsmen, the property includes a 7+ acre stocked fishpond/waterfowl holding and six well-fed, water-controlled waterfowl impoundments designed for quality game management. Shoreline & Pier: Over 1,200 feet of shoreline revetment protects the coast. The private pier is equipped with two boat lifts and additional mooring capacity. Middleville is a "turn-key" legacy estate on Maryland’s Eastern Shore, offering a rare fusion of historic significance, 2025 modern luxury, and vast natural resources. In an era where land is the ultimate luxury, this is a unique opportunity to secure one of the region's most significant holdings.

29245 Howell Point Rd, Trappe

Listing courtesy of Holiday Real Estate. Contact: 4105247700

$475,000

Chesapeake By Del Webb. Popular 2 story Wittman model. Great room with gas fireplace, dining room, large eat-in kitchen with breakfast nook and center island, sunroom, office, 1st floor primary suite with walk-in closet and bath with walk-in shower and soaking tub, guest bedroom, hall bath and laundry. 2nd floor is perfect for guests with a loft, bedroom and bath. Features a 2 car rear loading garage, patio and lawn irrigation. Improvements include roof (2020), water heater (2019) and HVAC (November 2016). This is an active 55+ adult community with Clubhouse, outdoor pool, tennis/pickleball courts, putting green, bocce ball, picnic areas, gazebos and exercise paths. Close to downtown Easton with nice restaurants, medical facilities, YMCA, churches, parks and more. This one owner home has been immaculately maintained.

Chesapeake By Del Webb. Popular 2 story Wittman model. Great room with gas fireplace, dining room, large eat-in kitchen with breakfast nook and center island, sunroom, office, 1st floor primary suite with walk-in closet and bath with walk-in shower and soaking tub, guest bedroom, hall bath and laundry. 2nd floor is perfect for guests with a loft, bedroom and bath. Features a 2 car rear loading garage, patio and lawn irrigation. Improvements include roof (2020), water heater (2019) and HVAC (November 2016). This is an active 55+ adult community with Clubhouse, outdoor pool, tennis/pickleball courts, putting green, bocce ball, picnic areas, gazebos and exercise paths. Close to downtown Easton with nice restaurants, medical facilities, YMCA, churches, parks and more. This one owner home has been immaculately maintained.

7344 Casey Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$335,000

Historic Farmhouse with Significant Value-Add Potential Built in 1919 and offering approximately 3,448 square feet, this stately farmhouse sits on a .44-acre lot and presents a rare opportunity for investors or renovation enthusiasts to restore a historic property with substantial upside. The home features many original architectural elements, including hardwood floors, crown molding, multiple fireplaces, wood pocket doors, and a grand staircase that highlight the craftsmanship of the era. The spacious main level includes two large sitting rooms, a formal dining room with floor-to-ceiling windows overlooking the wraparound porch, and a large kitchen with walk-in pantry. Additional features on this floor include a laundry area, half bath, and a secondary staircase leading to the upper level. Upstairs you’ll find five bedrooms and two full bathrooms, along with multiple linen closets and a long hallway lined with original wood doors. The third floor offers a sixth bedroom and an additional flex space, providing even more potential for added living area. With 3 levels of living space and a large footprint, this property offers an excellent canvas for renovation or restoration. Homes in the area that have been updated command significantly higher values, making this a compelling value-add investment opportunity. Property is being sold strictly as-is.

6 Beds ⋅ 3 Baths

Historic Farmhouse with Significant Value-Add Potential Built in 1919 and offering approximately 3,448 square feet, this stately farmhouse sits on a .44-acre lot and presents a rare opportunity for investors or renovation enthusiasts to restore a historic property with substantial upside. The home features many original architectural elements, including hardwood floors, crown molding, multiple fireplaces, wood pocket doors, and a grand staircase that highlight the craftsmanship of the era. The spacious main level includes two large sitting rooms, a formal dining room with floor-to-ceiling windows overlooking the wraparound porch, and a large kitchen with walk-in pantry. Additional features on this floor include a laundry area, half bath, and a secondary staircase leading to the upper level. Upstairs you’ll find five bedrooms and two full bathrooms, along with multiple linen closets and a long hallway lined with original wood doors. The third floor offers a sixth bedroom and an additional flex space, providing even more potential for added living area. With 3 levels of living space and a large footprint, this property offers an excellent canvas for renovation or restoration. Homes in the area that have been updated command significantly higher values, making this a compelling value-add investment opportunity. Property is being sold strictly as-is.

4096 Main St, Trappe

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$5,350,000

Envisioned for a premier waterfront setting along the Tred Avon River, this exceptional TO-BE-BUILT coastal residence by award-winning firm - Pacquin Design Build, presents a rare opportunity to create a refined Eastern Shore retreat on a remarkable 4.18-acre homesite within the exclusive Morgan’s Point community of Oxford. Thoughtfully designed in classic shingle-style architecture, the proposed home is perfectly oriented to capture sweeping river views, abundant natural light, and a seamless connection between indoor and outdoor living. The proposed floor plan balances timeless elegance with everyday comfort, featuring open yet well-defined living spaces that flow effortlessly toward the waterfront. A chef’s kitchen anchors the main level, opening to inviting gathering areas and expansive terraces overlooking the river. Walls of glass frame the ever-changing water views, while a main-level bedroom suite offers flexibility for guests or convenient single-level living. The upper level is designed as a private retreat, highlighted by a serene primary suite with elevated river views and additional bedrooms thoughtfully arranged for family and guests. Outdoors, the concept plan showcases a resort-inspired setting with a waterfront pool, generous patios, and sweeping lawn leading to approximately 389 feet of rip-rap shoreline. Boating, paddleboarding, and relaxed days by the water are central to the lifestyle this property affords. The lot is fully usable, offers ample mean low water depth, has an approved perc, and does not require flood insurance, making it an ideal canvas for a custom estate, family compound, or legacy retreat. Lot can be purchased separately for $2,250,000 (MDTA2012470) Set within the natural beauty and refined charm of Talbot County, and just moments from the Chesapeake Bay, this extraordinary offering combines privacy, scale, and location. A rare chance to bring a bespoke coastal vision to life on one of the Eastern Shore’s most desirable riverfront parcels—perfect as a year-round residence or second-home sanctuary. Located in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC; Northern Virginia; Annapolis; and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

4 Beds ⋅ 6 Baths

Envisioned for a premier waterfront setting along the Tred Avon River, this exceptional TO-BE-BUILT coastal residence by award-winning firm - Pacquin Design Build, presents a rare opportunity to create a refined Eastern Shore retreat on a remarkable 4.18-acre homesite within the exclusive Morgan’s Point community of Oxford. Thoughtfully designed in classic shingle-style architecture, the proposed home is perfectly oriented to capture sweeping river views, abundant natural light, and a seamless connection between indoor and outdoor living. The proposed floor plan balances timeless elegance with everyday comfort, featuring open yet well-defined living spaces that flow effortlessly toward the waterfront. A chef’s kitchen anchors the main level, opening to inviting gathering areas and expansive terraces overlooking the river. Walls of glass frame the ever-changing water views, while a main-level bedroom suite offers flexibility for guests or convenient single-level living. The upper level is designed as a private retreat, highlighted by a serene primary suite with elevated river views and additional bedrooms thoughtfully arranged for family and guests. Outdoors, the concept plan showcases a resort-inspired setting with a waterfront pool, generous patios, and sweeping lawn leading to approximately 389 feet of rip-rap shoreline. Boating, paddleboarding, and relaxed days by the water are central to the lifestyle this property affords. The lot is fully usable, offers ample mean low water depth, has an approved perc, and does not require flood insurance, making it an ideal canvas for a custom estate, family compound, or legacy retreat. Lot can be purchased separately for $2,250,000 (MDTA2012470) Set within the natural beauty and refined charm of Talbot County, and just moments from the Chesapeake Bay, this extraordinary offering combines privacy, scale, and location. A rare chance to bring a bespoke coastal vision to life on one of the Eastern Shore’s most desirable riverfront parcels—perfect as a year-round residence or second-home sanctuary. Located in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC; Northern Virginia; Annapolis; and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

Morgans Point Dr, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$7,500,000

Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of thoughtfully curated living space, positioned to capture sweeping waterfront views. A gracious front porch welcomes you into a grand foyer, setting the tone for the exceptional craftsmanship found throughout. The main level offers soaring 12-foot ceilings, rich hardwood floors, expansive windows and doors and custom millwork including crown molding, coffered and tray ceilings and elegant board-and-batten detailing. At the heart of the home, the living room serves as a remarkable gathering space with a dramatic floor-to-ceiling stone fireplace, custom built-ins, coffered ceilings, a wet bar and access to the rear porch. The kitchen is a stunning focal point, featuring a diamond coffered ceiling, custom handmade walnut cabinetry, two oversized islands, white and leathered granite countertops, and a Wolf six-burner, dual-oven range. A fully equipped butler’s pantry offers extensive cabinetry, generous counter space, a secondary refrigerator, dual dishwashers, a wine refrigerator and an electric oven. The open dining area flows seamlessly between the kitchen and living room. The primary suite is a private retreat with a tray ceiling, wood-burning fireplace, expansive walk-in closet with custom built-ins and vanity and a luxurious bath featuring heated floors, a jetted soaking tub, separate vanities, an open tile-and-glass shower and a private water closet. The suite is completed by a private sitting room with fireplace and wet bar, along with a private screened porch overlooking the gardens and serene waterfront. Four additional ensuite bedrooms each offer unique and luxurious bath designs. A well-appointed laundry room with ample cabinetry and generous counter space enhances everyday convenience and leads directly to a functional mudroom with access to the attached two-car garage. The second level features 9-foot ceilings and is anchored by a spacious family room with a stone hearth wood-burning fireplace and built-in window seating, flowing into a billiards area with wet bar, creating an ideal space for entertaining. The sixth bedroom currently includes custom built-in bunk beds but was originally designed as a home office and offers flexibility to be restored to its original use. The home’s exceptional design extends seamlessly outdoors, with a spacious screened porch leading to an open-air porch with a wood-burning fireplace and outdoor entertainment setup. Bluestone walkways and patios lead to a 20’ x 40’ lagoon-style Gunite pool with a waterfall feature, an outdoor kitchen and a waterside fire pit offering stunning sunset views over the cove. The property also includes a charming one-bedroom guest house with a luxury kitchen, open living area with fireplace and screened porch. A private dock with approximately 6’ MLW offers two boat slips, a floating dock and access to waterfront dining and premier fishing throughout the Chesapeake Bay and surrounding tributaries. Additional highlights to the home include a greenhouse with raised garden beds, a fenced garden area, professional landscaping with accent lighting, and a full irrigation system. This exceptional estate is truly one-of-a-kind!

6 Beds ⋅ 8 Baths

Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of thoughtfully curated living space, positioned to capture sweeping waterfront views. A gracious front porch welcomes you into a grand foyer, setting the tone for the exceptional craftsmanship found throughout. The main level offers soaring 12-foot ceilings, rich hardwood floors, expansive windows and doors and custom millwork including crown molding, coffered and tray ceilings and elegant board-and-batten detailing. At the heart of the home, the living room serves as a remarkable gathering space with a dramatic floor-to-ceiling stone fireplace, custom built-ins, coffered ceilings, a wet bar and access to the rear porch. The kitchen is a stunning focal point, featuring a diamond coffered ceiling, custom handmade walnut cabinetry, two oversized islands, white and leathered granite countertops, and a Wolf six-burner, dual-oven range. A fully equipped butler’s pantry offers extensive cabinetry, generous counter space, a secondary refrigerator, dual dishwashers, a wine refrigerator and an electric oven. The open dining area flows seamlessly between the kitchen and living room. The primary suite is a private retreat with a tray ceiling, wood-burning fireplace, expansive walk-in closet with custom built-ins and vanity and a luxurious bath featuring heated floors, a jetted soaking tub, separate vanities, an open tile-and-glass shower and a private water closet. The suite is completed by a private sitting room with fireplace and wet bar, along with a private screened porch overlooking the gardens and serene waterfront. Four additional ensuite bedrooms each offer unique and luxurious bath designs. A well-appointed laundry room with ample cabinetry and generous counter space enhances everyday convenience and leads directly to a functional mudroom with access to the attached two-car garage. The second level features 9-foot ceilings and is anchored by a spacious family room with a stone hearth wood-burning fireplace and built-in window seating, flowing into a billiards area with wet bar, creating an ideal space for entertaining. The sixth bedroom currently includes custom built-in bunk beds but was originally designed as a home office and offers flexibility to be restored to its original use. The home’s exceptional design extends seamlessly outdoors, with a spacious screened porch leading to an open-air porch with a wood-burning fireplace and outdoor entertainment setup. Bluestone walkways and patios lead to a 20’ x 40’ lagoon-style Gunite pool with a waterfall feature, an outdoor kitchen and a waterside fire pit offering stunning sunset views over the cove. The property also includes a charming one-bedroom guest house with a luxury kitchen, open living area with fireplace and screened porch. A private dock with approximately 6’ MLW offers two boat slips, a floating dock and access to waterfront dining and premier fishing throughout the Chesapeake Bay and surrounding tributaries. Additional highlights to the home include a greenhouse with raised garden beds, a fenced garden area, professional landscaping with accent lighting, and a full irrigation system. This exceptional estate is truly one-of-a-kind!

7508 Cooper Point Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$449,000

No neighbors, private and set back off the road. Beautifully Updated Split-Level Retreat on Nearly an Acre Along Route 50! Set back on a private, wooded lot just under an acre, this beautifully remodeled 3-bedroom, 2.5-bath split-level home offers the perfect blend of comfort, style, and outdoor enjoyment. A long circular driveway welcomes you home, setting the tone for the peaceful setting that surrounds this 2,676 sq. ft. property. Inside, the home has been thoughtfully updated since purchase, including new replacement windows, mini-splits, new paint, new LVP flooring, a fully remodeled bathroom, and a vapor barrier with insulated crawl space—providing both modern comfort and long-term peace of mind. The main level features bright, open living spaces with sliding doors from both the living and dining rooms leading to the screened-in porch. From here, you can relax while overlooking the serene pond and the inviting in-ground pool—an ideal setup for entertaining or unwinding after a long day. The finished lower level expands your living possibilities with a cozy den complete with a bar area, a utility/laundry room, and two bonus rooms that can easily be converted into a large fourth bedroom or additional sleeping quarters. Sliding doors from the den offer direct access to the pool area, creating a seamless indoor-outdoor flow. Additional highlights include a wood-burning stove, ample storage, and the flexibility to add 1–2 more bedrooms if desired. With professional photos coming soon, this move-in-ready home is sure to draw attention quickly. A rare combination of privacy, upgrades, and lifestyle amenities—this one truly won’t last. Pool will be open soon.

No neighbors, private and set back off the road. Beautifully Updated Split-Level Retreat on Nearly an Acre Along Route 50! Set back on a private, wooded lot just under an acre, this beautifully remodeled 3-bedroom, 2.5-bath split-level home offers the perfect blend of comfort, style, and outdoor enjoyment. A long circular driveway welcomes you home, setting the tone for the peaceful setting that surrounds this 2,676 sq. ft. property. Inside, the home has been thoughtfully updated since purchase, including new replacement windows, mini-splits, new paint, new LVP flooring, a fully remodeled bathroom, and a vapor barrier with insulated crawl space—providing both modern comfort and long-term peace of mind. The main level features bright, open living spaces with sliding doors from both the living and dining rooms leading to the screened-in porch. From here, you can relax while overlooking the serene pond and the inviting in-ground pool—an ideal setup for entertaining or unwinding after a long day. The finished lower level expands your living possibilities with a cozy den complete with a bar area, a utility/laundry room, and two bonus rooms that can easily be converted into a large fourth bedroom or additional sleeping quarters. Sliding doors from the den offer direct access to the pool area, creating a seamless indoor-outdoor flow. Additional highlights include a wood-burning stove, ample storage, and the flexibility to add 1–2 more bedrooms if desired. With professional photos coming soon, this move-in-ready home is sure to draw attention quickly. A rare combination of privacy, upgrades, and lifestyle amenities—this one truly won’t last. Pool will be open soon.

7364 Ocean Gtwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$499,990

Discover the charm of 8699 Harper Way, a new home in Gannon Range, ideally located minutes away from downtown Easton, MD, boasting serene surroundings and convenient proximity to Route 50. This 2,401 square foot, open concept two-story home offers three bedrooms, including a first-floor primary, a flex room, three full bathrooms, 9’ ceilings, a loft, and a two-car garage. A welcoming foyer leads you to the spacious guest bedroom with a closet, the guest bathroom and a linen closet. The inviting flex room is a versatile space with an abundance of natural light. The home's well-designed kitchen features modern white cabinets, granite countertops, a generous walk-in pantry, an oversized island and stainless-steel appliances. The kitchen is open to the ample living room and dining room that leads to the privately covered patio at the back of the home and a fully sodded, landscaped and irrigated lawn. The large first floor owner’s suite is a retreat in the back of the home; its private bathroom has a substantial double bowl vanity, shower and linen closet and the impressive walk-in closet is must-see. Tucked away, the laundry room and a coat closet are located just off the two-car garage next to the stairs which will lead you to a third bedroom, full bathroom, and a spacious loft with lots of additional storage space. This home includes the exclusive America’s Smart Home® package through ADT and white window treatments. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

Discover the charm of 8699 Harper Way, a new home in Gannon Range, ideally located minutes away from downtown Easton, MD, boasting serene surroundings and convenient proximity to Route 50. This 2,401 square foot, open concept two-story home offers three bedrooms, including a first-floor primary, a flex room, three full bathrooms, 9’ ceilings, a loft, and a two-car garage. A welcoming foyer leads you to the spacious guest bedroom with a closet, the guest bathroom and a linen closet. The inviting flex room is a versatile space with an abundance of natural light. The home's well-designed kitchen features modern white cabinets, granite countertops, a generous walk-in pantry, an oversized island and stainless-steel appliances. The kitchen is open to the ample living room and dining room that leads to the privately covered patio at the back of the home and a fully sodded, landscaped and irrigated lawn. The large first floor owner’s suite is a retreat in the back of the home; its private bathroom has a substantial double bowl vanity, shower and linen closet and the impressive walk-in closet is must-see. Tucked away, the laundry room and a coat closet are located just off the two-car garage next to the stairs which will lead you to a third bedroom, full bathroom, and a spacious loft with lots of additional storage space. This home includes the exclusive America’s Smart Home® package through ADT and white window treatments. Pictures, artist renderings, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Image representative of plan only and may vary as built. Images are of model home and include custom design features that may not be available in other homes. Furnishings and decorative items not included with home purchase.

8699 Harper Way, Easton

Listing courtesy of D.R. Horton Realty of Virginia, LLC. Contact: 3017013700

$575,000

Spacious Colonial in Charlestown Village - Welcome home to this beautifully cared-for Colonial offering 4 bedrooms, 2.5 baths, and over 2,288 sq. ft. of living space (actual square footage exceeds the tax record). The main level features hardwood flooring and a comfortable flow designed for everyday living and entertaining. At the back of the home, the kitchen with stainless steel appliances and granite countertops opens to a breakfast area and a cozy family room with a gas fireplace, all with easy access to the deck and in-ground pool. The main level also includes a formal dining room and a flexible living room/office. Upstairs, a spacious bonus room over the garage offers the perfect hangout space—or could easily serve as the 4th bedroom. Outside, enjoy a fenced backyard, large storage shed, paved driveway, and an attached 2-car garage. Charlestown Village is a sought-after neighborhood featuring lighted streets, sidewalks, and in-town convenience. This home combines space, comfort, and an ideal location. The owners are currently building a new home.

Spacious Colonial in Charlestown Village - Welcome home to this beautifully cared-for Colonial offering 4 bedrooms, 2.5 baths, and over 2,288 sq. ft. of living space (actual square footage exceeds the tax record). The main level features hardwood flooring and a comfortable flow designed for everyday living and entertaining. At the back of the home, the kitchen with stainless steel appliances and granite countertops opens to a breakfast area and a cozy family room with a gas fireplace, all with easy access to the deck and in-ground pool. The main level also includes a formal dining room and a flexible living room/office. Upstairs, a spacious bonus room over the garage offers the perfect hangout space—or could easily serve as the 4th bedroom. Outside, enjoy a fenced backyard, large storage shed, paved driveway, and an attached 2-car garage. Charlestown Village is a sought-after neighborhood featuring lighted streets, sidewalks, and in-town convenience. This home combines space, comfort, and an ideal location. The owners are currently building a new home.

316 Spring Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$999,000

A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual needs, all while maintaining privacy and a connection to the surrounding natural landscape. Restaurants, shops, seasonal events, waterfront parks, and the charm of the historic district are all close at hand, yet the property feels quietly removed. Approximately three times the size of a typical in-town lot, the parcel allows for thoughtful home placement, outdoor living areas, and driveway access from Miles Avenue, Canton Street, or both, depending on the final plan. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual needs, all while maintaining privacy and a connection to the surrounding natural landscape. Restaurants, shops, seasonal events, waterfront parks, and the charm of the historic district are all close at hand, yet the property feels quietly removed. Approximately three times the size of a typical in-town lot, the parcel allows for thoughtful home placement, outdoor living areas, and driveway access from Miles Avenue, Canton Street, or both, depending on the final plan. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

108 Miles Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$779,000

A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces that can be tailored to the buyer’s preferences while preserving privacy and connection to the natural setting. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and tucked away. Approximately three times the size of a typical in-town lot, the parcel allows generous room for outdoor living and thoughtful home placement, with driveway access possible from Miles Avenue, Canton Street, or both, depending on final design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces that can be tailored to the buyer’s preferences while preserving privacy and connection to the natural setting. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and tucked away. Approximately three times the size of a typical in-town lot, the parcel allows generous room for outdoor living and thoughtful home placement, with driveway access possible from Miles Avenue, Canton Street, or both, depending on final design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

108 Miles Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$479,000

Move-In Ready Kensington Model in Mulberry Station. Welcome home to this spacious 4 bedroom, 2.5 bath residence offering over 2,300 sq. ft. of beautifully designed living space in the sought-after Mulberry Station community. Perfectly positioned on a large lot that backs to open farmland, this property combines modern upgrades with timeless charm. Key Features & Upgrades: 9’ ceilings on the main level with hardwood foyer and elegant 2-story design. Chef’s kitchen with Merillat cabinetry, granite counters, and full suite of appliances (including microwave) Family room with natural gas fireplace—a cozy centerpiece for gatherings. Vaulted primary suite with cathedral ceiling, bay window, and a luxurious super bath featuring whirlpool tub. Dual-zone HVAC for year-round comfort. Andersen windows, insulated doors, and brick skirt detail for lasting quality. Landscaping, concrete driveway, and sodded front & sides for instant curb appeal. 2-car attached garage with 220V line. Lifestyle Benefits: Bright breakfast area plus formal dining room for entertaining. Hardwood floors throughout the main level for a refined touch. Large lot with space for outdoor living, gardening, or future pool installation. Convenient location—close to town amenities and just minutes to Rt. 50 for an easy commute. This home is move-in ready, priced to sell, and designed for comfort and style. With its thoughtful upgrades, spacious layout, and prime Easton location, it’s the perfect blend of elegance and everyday convenience. This home is currently being painted, professionally cleaned and carpets professionally steam cleaned!

Move-In Ready Kensington Model in Mulberry Station. Welcome home to this spacious 4 bedroom, 2.5 bath residence offering over 2,300 sq. ft. of beautifully designed living space in the sought-after Mulberry Station community. Perfectly positioned on a large lot that backs to open farmland, this property combines modern upgrades with timeless charm. Key Features & Upgrades: 9’ ceilings on the main level with hardwood foyer and elegant 2-story design. Chef’s kitchen with Merillat cabinetry, granite counters, and full suite of appliances (including microwave) Family room with natural gas fireplace—a cozy centerpiece for gatherings. Vaulted primary suite with cathedral ceiling, bay window, and a luxurious super bath featuring whirlpool tub. Dual-zone HVAC for year-round comfort. Andersen windows, insulated doors, and brick skirt detail for lasting quality. Landscaping, concrete driveway, and sodded front & sides for instant curb appeal. 2-car attached garage with 220V line. Lifestyle Benefits: Bright breakfast area plus formal dining room for entertaining. Hardwood floors throughout the main level for a refined touch. Large lot with space for outdoor living, gardening, or future pool installation. Convenient location—close to town amenities and just minutes to Rt. 50 for an easy commute. This home is move-in ready, priced to sell, and designed for comfort and style. With its thoughtful upgrades, spacious layout, and prime Easton location, it’s the perfect blend of elegance and everyday convenience. This home is currently being painted, professionally cleaned and carpets professionally steam cleaned!

8800 Roundhouse Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$3,100,000

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

4 Beds ⋅ 4 Baths

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch—perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butler’s pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

23961 Lynnewood Dr, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$774,000

Designed to optimize water views of the Tred Avon and access to the community kayak launch and beach area is this to be built home. Centrally located between Easton and St Michaels and just a stone's throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County's premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Additional floor plans, options, and upgrades available. Some photos and renderings are for illustrative purposes only and may include additional upgrades.