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$629,990
3 Beds ⋅ 3 Baths
Welcome to the Kerr, a beautifully designed home that pairs an open-concept layout with timeless Classic elements. Offering 3 bedrooms, 3 baths, and a 3-car garage, this home provides both elegance and everyday functionality. The spacious kitchen and dining area are both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with an optional freestanding tub and walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

29347 Blackiston St, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$479,990
2 Beds ⋅ 2 Baths
Welcome to the Spring Lake II, a beautifully designed home that pairs an open-concept layout with timeless Loft elements. Offering 2 bedrooms, 2 baths, and a 2-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with an optional freestanding tub and walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

7854 Ward Brothers Cir, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$489,990
2 Beds ⋅ 2 Baths
Welcome to the Spring Lake II, a beautifully designed home that pairs an open-concept layout with timeless Loft elements. Offering 2 bedrooms, 2 baths, and a 2-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with an optional freestanding tub and walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

29397 Jobes St, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$85,000
Rare buildable lot in Talbot County! Featuring an approved SDA Plat from the Health Department, this property offers a valuable head start in the building process. Located right outside of desirable Town Of Easton, you’ll enjoy peaceful surroundings with convenient access to RT 50 with a few minute drive. Don't miss out on this rare opportunity!

6199 Landing Neck, Easton

Listing courtesy of The Parker Group. Contact: 3022176692
$359,900
2 Beds ⋅ 3 Baths
Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living.

9531 Quail Hollow Dr Unit #405, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$850,000
4 Beds ⋅ 4 Baths
Easton Club. This beautiful 3300 sq. ft. home has been almost entirely renovated. Living room, formal dining room, renovated kitchen with Quartz countertops, new appliances and breakfast area, family room with stone gas fireplace, 1st floor primary suite with remodeled bath, laundry room and powder room. Wood flooring throughout 1st floor. 2nd floor offers 3 bedrooms, 2 baths and large media room or 5th bedroom. Exterior features a tiered deck with awning, lawn irrigation system and extensive landscaping. Sited on a .35 acre lot backing to open space on a quiet cul-de-sac. Roof (new 2023). HVAC (new 2022). Community amenities include a pool and tennis/pickleball court. Close to downtown Easton and many amenities. Short distance to the picturesque towns of St. Michaels and Oxford. A must to see!

28391 Masters Ct, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$649,990
3 Beds ⋅ 4 Baths
Welcome to the Franklin, a beautifully designed home that pairs an open-concept layout with timeless Classic elements. Offering 3 bedrooms, 3.5 baths, and a 2.5-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with an optional freestanding tub and walk-in closet. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

29401 Jobes St, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$534,900
3 Beds ⋅ 3 Baths
Welcome to this beautifully updated two-story Wittman model in the highly sought-after 55+ community of Easton Club East, where thoughtful upgrades and timeless design come together effortlessly. From the moment you step inside, you’ll notice the extensive improvements throughout, from custom paint and upgraded lighting to engineered wood flooring and high-end finishes that elevate every space. The heart of the home is the stunning, fully renovated kitchen (approx. 3 years young), featuring granite countertops, a center island with seating, custom cabinetry with soft-close drawers, and stainless steel appliances. Heated floors add an extra touch of comfort, while the adjoining breakfast nook and sunroom create the perfect setting for morning coffee overlooking the private backyard. The spacious great room is designed for both relaxing and entertaining, complete with a natural gas fireplace, along with built-in wiring for surround sound. A dedicated office provides flexibility for work or hobbies, while the main-level primary suite offers comfort and convenience with an updated bath, walk-in shower, and custom finishes. A guest bedroom and additional full bath on the main level provide ideal space for visitors. Upstairs, a large loft expands your living space, accompanied by an additional bedroom and full bath, perfect for guests or extended stays. Additional upgrades continue throughout the home, including custom window treatments, Hunter Douglas shades, enhanced storage solutions, and a fully insulated garage with built-in cabinetry, workbench, and its own mini-split heating and cooling system. Step outside to enjoy the extended paver patio, complete with a remote-controlled awning, landscape lighting, and irrigation system, creating a beautifully maintained outdoor retreat. Located in Easton Club East, residents enjoy resort-style amenities including a clubhouse, outdoor pool, tennis courts, bocce ball, putting green, scenic walking paths, and picnic areas with gazebos. This is a rare opportunity to own a meticulously maintained and extensively upgraded home in one of Easton’s most desirable communities. Schedule your private showing today and experience it for yourself.

7401 Casey Ave, Easton

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$1,250,000
4 Beds ⋅ 3 Baths
Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.

5480 Windward Dr, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$1,250,000
Here's your chance to own a full service waterfront restaurant and a piece of Tilghman Island history. This property has operated as a restaurant for almost 90 years. Located on Knapps Narrows, Gina's at the Bridge, is literally right next to one of the busiest drawbridges in the country. Bridge openings are by "demand of the boat" waterfront diners have many opportunities to see a wide variety of boats and watercraft coming and going. There is a full service bar inside. Indoor dining has 3 separate areas. Upstairs is an area for private dinners or small gatherings and opens to an outside deck with views of the Chesapeake Bay. Outside dining along Knapps Narrows seats about 80 people. There is also an outdoor Tiki Bar. This restaurant is turnkey. All restaurant equipment, tables, chairs, artwork etc. convey. Price includes real estate and restaurant business.

6136 Tilghman Island Rd, Tilghman

Listing courtesy of Tilghman Island Realty Inc. Contact:

$4,125,000
Zoned MXW this is one of the last remaining large parcels in the Town of Easton, Maryland Plans must be approved by Easton Planning and Zoning . See zoning for permitted uses. With approved residential uses there are some applications that will go along with an appropriate commercial applications. However the main use for this will be residential. Current leases are all cancellable and will be done a settlement.

306 Port St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$4,125,000
Largest remaining undeveloped parcel in the Town of Easton with attractive zoning of MXW. Please review permitted applications and development requirements. Agents must represent Buyers as their agent. Existing radio towers to be removed by seller, building lease is cancelable with a small land lease to adjacent building. Reasonable due diligence time will be considered with an executed contract. Prefer Buyers use local engineering and legal counsel. Close to Easton Point and the Tred Avon with great upside potential for future development. Currently zoned MXW a special Town zoning. Contact agent with questions.

306 Port St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$2,895,000
4 Beds ⋅ 5 Baths
With sweeping sunset views, this picturesque estate—perfectly situation on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the property features an impressive two‑story Tidewater Colonial of approximately 3,500± fsf that includes a first‑floor primary suite with a private library, multiple walk‑in closets, and a beautifully finished bath; two additional bedrooms and full bath upstairs; a guest apartment with separate kitchenette, bedroom and full bath; a large two‑car garage; and a stunning concrete pool framed by expansive stone patios. The current owners thoughtfully reimagined and upgraded the interior, relocating the kitchen to the waterside, expanding and renovating the spacious family room and first‑floor primary suite, adding an exceptional bar/butler’s pantry with custom cabinetry, refrigerator, dishwasher, and icemaker, and creating a central multi-purpose laundry room. Exterior features include low‑maintenance brick and siding, new roof on the renovated waterside, paved drive with ample parking, and an attached two‑car garage with a separate climate‑controlled workout room and half bath. The fully protected, riprapped shoreline spans approximately 665 feet and features a new pier with two deepwater slips (6’+ MLW), electric and water service, plus a separate kayak dock and launch. From any of the property’s many vantage points, enjoy majestic shade trees, mature landscaping, and an ever-changing panorama of natural beauty—imagine watching schools of fish and abundant waterfowl daily—making this an ideal Eastern Shore retreat.

4440 Baildon Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$2,995,000
3 Beds ⋅ 4 Baths
Welcome to Holly House – A Rare Waterfront Legacy Estate on the Miles River Holly House presents an extraordinary opportunity to own one of the Upper Miles River’s most captivating waterfront estates. Set gracefully on five spectacular, beautifully landscaped acres, this contemporary French-inspired residence offers approximately 150 feet of private shoreline, panoramic water views, and unforgettable sunsets. Designed for effortless one-level living, the impeccably constructed brick home blends timeless architecture with endless potential. The current residence features a gracious living room, formal dining room, inviting den, spacious kitchen, sunroom, private office, study/optional bedroom, an elegant waterfront primary suite with dual bathrooms and separate walk-in closets, two additional en-suite bedrooms, a powder room, unfinished basement, and an attached two-car garage. Outdoor living is equally impressive. A waterside 8-foot-deep swimming pool, expansive terrace overlooking the Miles River, private 150-foot pier, tennis court, and oversized outbuilding create an exceptional setting for entertaining, recreation, and peaceful waterfront living. Whether you choose to thoughtfully refresh the existing home or create a spectacular new estate, Holly House offers an unmatched canvas to realize your vision. Adding even greater value, the property includes fully approved architectural, structural, and interior design plans for an extraordinary three-story Modern Country French estate. Every detail has been thoughtfully curated to create a truly remarkable waterfront residence featuring: ● Five bedrooms, including a luxurious waterfront primary suite on the first floor ● Four-stop elevator ● Six full baths and two half baths (powder room and dedicated pool bath) ● Five fireplaces ● Grand staircase ● Dramatic vaulted living room ● Glass-enclosed dining room with black iron NanoWall doors opening to breathtaking Miles River views ● Spacious family room seamlessly connected to an entertainer’s dream kitchen ● Bar, butler’s pantry, and separate catering kitchen with silver vault ● Expansive lower level with a temperature-controlled wine cellar, billiards room, home theater, oversized fitness center, full bath with dog wash, and abundant storage ● Covered 440-square-foot vaulted timber patio with an outdoor wood-burning fireplace and television, creating the ultimate year-round outdoor living space The property has also received its long-awaited approval from Talbot County for a new 5-6 bedroom septic system, allowing construction to begin immediately. Fully permitted architectural and structural plans, along with a stunning full-color exterior fly-through video, are included with the sale. For those wishing to personalize the design, the approved plans can be modified to reflect a buyer’s individual style and lifestyle needs. This is more than a home—it’s a once-in-a-generation opportunity to create a landmark waterfront estate in one of the Eastern Shore’s most coveted locations.

9338 Bantry Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: chevychase@ttrsir.com
$525,000
3 Beds ⋅ 3 Baths
Welcome to Easton Club East, Easton's premiere 55+ community with mature trees and sidewalks and ton of amenities for a vibrant lifestyle! Bright and open with first floor bedroom, this Newcomb model on a large corner lot offers ease of living with just the right amount of space. Nearly 3,000sf, the home features wood floors throughout the first floor and a soaring 10-foot ceilings for a truly spacious feel. The sunny kitchen dining area leads to a bright sun porch offering great space for a craft room, office or additional seating. Kitchen features stainless appliances and granite counter tops while the family room w/ gas fireplace offers warm and inviting everyday living. Glass doors lead off the entry to a private office or media space while across the hall is a formal dining area with elegant tray ceiling ... perfect for family gatherings or quiet dinners. The primary suite is also on the first floor and features wood floors and a stunning tray ceiling. The primary suite includes a large walk-in closet and en-suite bath with double sinks, soaking tub, and walk-in shower. Upstairs there are two bedrooms and a full bath ... perfect for house guests or option for a second workspace. The large back patio is the ideal place to enjoy a sunny morning with your coffee or a relaxing evening with friends. Spacious two-car garage offers additional storage. Laundry on the main level. Easton Club East residents enjoy amenities including a clubhouse with fitness center, library, and game room. Outdoor amenities include a swimming pool, tennis and pickle ball courts, bocce courts, putting green, walking trails, and scenic ponds. Located just minutes from downtown Easton, you'll have easy access to shopping, restaurants, healthcare, and everyday conveniences. For commuters and travelers, the Bay Bridge is approximately 30 minutes away, with Annapolis, Baltimore, Washington, D.C., and the Delaware and Maryland beaches all within an easy drive.

7351 Casey Ave, Easton

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$509,000
3 Beds ⋅ 3 Baths
Chesapeake by Del Webb. Nicely sited for maximum sunshine , this handsome and beautifully cared for two story Wittman model awaits you. Recent upgrades include luxury Vinyl flooring throughout the entire house ( even the stairs ! ) , entire house repainted neutral tones, custom blinds, enhanced lighting and fans, architectural roof, new high quality kitchen appliances including washer/dryer, primary bedroom closet organization, all bathrooms refreshed, fenced rear yard and drywalled/painted garage interior. The layout offers traditional rooms that blend together with attractive sight lines and connectivity. Step outside and find a relaxing brick paver patio with mature privacy plantings and a natural gas Weber Grill connected to town gas service all encompassed within the fenced back yard. This is a great house, move in ready for you! 55+ age-restricted section. Community amenities include Clubhouse with meeting room, exercise rooms, library and game rooms, outdoor pool, tennis/pickleball courts, picnic areas and common grounds, putting green, exercise paths, bocce ball, horse shoes and more. Located close to downtown Easton with fine restaurants and shopping and medical facilities, St. Michaels and Oxford. 1.5 hours to MD/DE beaches. 30 minutes to Bay Bridge.

7432 Karen Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$410,000
4 Beds ⋅ 2 Baths
Renovated 4 BR, 2 full bath home close to schools and Idlewild Park. Situated on private 1.54 acres. R10A  zoning which allows up to 5 building lots according to study. Possibility of building your dream home on the back of the property near the pond and stream that runs along the property line while living in the current residence, then sell off the existing house to help offset your building costs. One could also make and sell off additional lots to keep the cost of home ownership down. The zoning also allows for apartments, condos, or townhouses to be built.

29328 Dutchmans Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$7,800,000
4 Beds ⋅ 5 Baths
Grafton Manour Estate—A Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86±-acre peninsula wrapped by approximately 1.5± miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true Chesapeake Bay access. Property Highlights: 86± acres with sweeping water vistas, open fields, and meticulously manicured lawns. Varied shoreline: riprap, sandy beaches, and natural grasses. Deep-water pier with 7' MLW, suitable for larger boats and sailboats; direct access to the Chesapeake Bay. Two subdivided, waterfront lots included: Lot 2: 6± acres on Briary Cove (east side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Lot 3: 5.5± acres is located on Waterhole Cove (west side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Historic Lowes Family Cemetery on the west side, dating to the 1700s. Land mix: approximately 60± acres tillable; balance in timber and lawns along the eastern shoreline. Main Residence: Custom-built in 2004, approx. 7,400 sq ft, four en suite bedrooms. Primary suite in the main-floor north wing with private laundry, library, office/workout room, and sunroom. Dramatic great room and dining room with vaulted ceiling, chestnut beams, cedar ceiling, and a raised-hearth stone fireplace. Signature silo feature: 1st and 2nd floors: full baths serving two bedrooms. 3rd floor: window-lined observatory with 360° views across the estate. Wide-plank wood floors milled from the same chestnut as the great room beams. Exceptional craftsmanship throughout; a must-see for discerning buyers. Guest/Farmhouse: Approx. 2,000 sq ft with three bedrooms and one bath. Two wood-burning fireplaces (living room and dining room). Charming and versatile for guests, caretakers, or rental income. Barns and Outbuildings: Large heated barn with concrete floors, three overhead doors, expansive workbench, and open-loft recreation room. Attached a conditioned office/hunters’ lodge with full bath and hookups for laundry and kitchenette. Adjacent irrigated, fenced raised-bed garden; nearby small apple orchard. Additional smaller barn for equipment or livestock. Lifestyle and Possibilities: Ideal for a family compound, equestrian pursuits, or an exclusive retreat. Premier sporting opportunities: shoreline waterfowl, whitetail deer, and turkey. Ample acreage and infrastructure for hobby farming, vineyards, or conservation. A once-in-a-generation opportunity to own an iconic waterfront estate where open water, open sky, and open fields meet. Follow the country road home to the place you belong—Grafton Manour Estate. By appointment only. Do not enter the property by water or land without the listing agent. The property is monitored by camera surveillance 24/7.

22101 Grafton Manour Ln, Wittman

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$1,700,000
3 Beds ⋅ 3 Baths
Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for relaxing, entertaining and enjoying life on the water. Inside, a gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Property is offered as part of an estate and is being sold as is.

104 Myrtle St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$325,000
4 Beds ⋅ 3 Baths
Move-in ready, one-owner end-unit townhome built in 2022, proudly owner-occupied and meticulously maintained, located in the desirable Patriot Square community. This home offers 4 bedrooms and 2.5 bathrooms, with a primary suite and private bathroom on the main level, along with a convenient half bath—perfect for main-level living. The upper level features three additional bedrooms and one full bathroom, providing flexible space for family, guests, or a home office. The modern kitchen includes stainless steel appliances, including a dishwasher, stove, refrigerator, built-in microwave, and a washer and dryer that convey with the home. Ideally situated less than one mile from shopping, dining, and historic downtown Easton, MD, this home offers comfort, convenience, and location. Patriot Square is a well-maintained community of 133 single-family and townhome residences, supported by an active Homeowners Association committed to preserving property values and fostering a welcoming neighborhood atmosphere.

505 Wheatley Dr, Easton

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$849,000
3 Beds ⋅ 2 Baths
Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled interior featuring soaring vaulted ceilings and an open-concept floor plan designed for effortless everyday living and entertaining. Rich hardwood flooring flows throughout, complemented by a beautifully appointed chef’s kitchen, three well-proportioned bedrooms, and two elegantly finished full baths—all conveniently situated on a single level. Virtually every component of the home has been renewed, allowing the next owner to enjoy a truly turnkey property with the peace of mind that comes with comprehensive renovation. Outside, professionally designed landscaping surrounds a private backyard, creating a tranquil setting for outdoor dining, entertaining, or quiet relaxation. Ideally located in the heart of St. Michaels, the home is just moments from the town’s renowned boutiques, acclaimed restaurants, waterfront parks along the Miles River, the community pool, and the YMCA. Offering the rare combination of like-new construction and one of Maryland’s most desirable small-town settings, 803 New Lane presents an exceptional opportunity to enjoy Eastern Shore living at its finest.

803 New Ln, St Michaels

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

$1,495,000
5 Beds ⋅ 5 Baths
Some homes check the boxes. Others create a lifetime of memories......Welcome Home to 28091 Oaklands Circle Perfectly situated on over 2.5 beautifully landscaped acres in the highly desirable Oaklands community, this exceptional five-bedroom, four-and-a-half-bath custom home offers the rare combination of luxury, comfort, privacy, and a truly move-in-ready lifestyle. From the moment you arrive, you’ll appreciate the mature trees, manicured landscaping, fresh mulch, and natural privacy that surround this beautifully maintained property. Every detail reflects years of thoughtful care and pride of ownership. Inside, timeless craftsmanship meets thoughtful updates. Rich hardwood flooring flows throughout the home, complemented by replacement windows, recessed LED lighting, custom built-in shelving, window seats with hidden storage, and pocket doors that add both character and functionality. At the heart of the home is the beautifully updated kitchen featuring granite countertops, generous island workspace, coffee bar, breakfast area with lots of natural light and an inviting layout designed for everything from family dinners to holiday gatherings. With five spacious bedrooms, 4 1/2 bathrooms, great room, formal areas, and a fully finished bonus room above the attached three-car garage, the flexible floor plan easily accommodates growing, blended, or multi generational families, overnight guests, a home office, fitness room, or recreation space. Comfort can be found in every season. Enjoy the warmth of both a gas fireplace and a traditional wood-burning fireplace, or gather around the fire pit on cool evenings during cooler months. Just outside you will discover your own private retreat. Relax on the screened-in covered porch, multiple decks, spend afternoons and weekends lounging by the sparkling swimming pool with diving board, featuring a new pool cover and new pool pumps. Explore the custom tree fort and zip line, or simply enjoy the open green space that makes this property so special. Relax on any one of the multiple deck spaces overlooking the peaceful backyard or just simply soak up the AC in the summertime. A large storage shed provides plenty of room for lawn equipment, tools, and outdoor gear. Significant improvements—including replacement windows, approximately three-quarters of the roof replaced, and a whole-house backup generator—offer lasting value and peace of mind. A state-of-the-art security, alarm, and surveillance system adds another level of comfort for today’s homeowners. Located just minutes from historic downtown Easton or the waterfront town of Oxford, both with outstanding restaurants, boutique shopping, access to local healthcare, schools, and the waterfront lifestyle of Maryland’s Eastern Shore, this home offers the perfect balance of convenience and tranquility. Beautifully updated, meticulously maintained, and designed for everyday living as well as unforgettable entertaining, 28091 Oaklands Circle is more than a home—it’s where birthdays are celebrated, holidays are shared, and lifelong memories are made. Come experience the warmth, quality, and lifestyle that make this remarkable property truly one of Easton’s finest.

28091 Oaklands Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$395,000
2 Beds ⋅ 2 Baths
Comfortable living spaces can be found in this well-maintained 2BR/2BA townhome located just minutes from downtown Easton. Features include hardwood floors, wood-burning fireplace, newer kitchen appliances, washer and dryer. Carpeting was replaced a couple years ago. Convenient location with quick access to the Easton bypass and Rt 50, hospital and downtown.

1175 S Washington St Unit #18, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,550,000
Great Investment Opportunity – This 5500+/- sq ft Commercial Condo has a long term Lease with a well-established Tenant. Zoned Commercial, ideal for Medical or related Business. Excellent condition, great visibility and plenty of parking.

503 Cynwood Dr Unit #1, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$495,000
3 Beds ⋅ 2 Baths
Enjoy the ease of one-level living in this well-maintained rancher, built in 2002 and situated on 2+/- acres in the quaint village of Wittman. Offering 1,662+/- sqft, this 3-bedroom, 2-bath home provides comfortable living with plenty of room to enjoy both inside and out. Hardwood flooring welcomes you into the foyer, which opens to a spacious living room. The kitchen features ample cabinetry, generous table space and overlooks the backyard, creating the perfect setting for everyday meals or entertaining. The spacious primary bedroom features a large walk-in closet. A convenient side entry leads to the laundry room and a separate full bath. Outside, the open yard offers endless possibilities with plenty of space for gardening, recreation or simply enjoying the outdoors. The oversized detached garage provides abundant room for vehicles, a workshop, hobbies and additional storage, while the blacktop driveway adds convenience and curb appeal. A recently installed 3-ton HVAC system provides added comfort and peace of mind. Located less than ¾ of a mile from the Wittman boat landing, you'll have easy access to Cummings Creek, the Chesapeake Bay, and surrounding tributaries for boating, fishing, crabbing, kayaking, and waterfront dining. Conveniently situated between Tilghman Island and Historic downtown St. Michaels, this property offers the perfect opportunity to enjoy the relaxed lifestyle and natural beauty of Maryland's Eastern Shore.

8658 Cummings Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$115,000
Great Potential for this cleared lot !! , attention Investors , builders, or someone who wants to build the house of their dreams. 2.41 cleared Flat acres off of Rt 50, . Lot ready to be built . Lot has right of way through lot #2 Buyer responsible for doing diligent research on this residential lot and or other land use .

13433 Ocean Gateway, Queen Anne

Listing courtesy of Samson Properties. Contact: 3017555613
$3,595,000
5 Beds ⋅ 6 Baths
Perfectly nestled on 4.96± private waterfront acres between Easton and St. Michaels, this extraordinary estate embodies the very best of Eastern Shore living, anchored by rare deep water dockage (6’+ MLW) for the ultimate Chesapeake boating lifestyle. This Royal Oak home’s western exposure offers amazing sunset views across Solitude Creek.This listing also includes a fully prepaid 96-year recorded ground lease on an adjoining 5.48± acre parcel of land -- featuring a picturesque wildflower pasture, a mature 4± acre maple orchard, and charming outbuildings (detached garage and red barn) -- creating unparalleled privacy, beauty, and tranquility. A winding, tree-lined private drive sets the tone for the peaceful retreat that awaits. Inside, panoramic water views fill nearly every room, while the recently updated home blends timeless elegance with warm, inviting comfort. Soaring ceilings, rich hardwood floors, exquisite custom moldings, and expansive living spaces create an atmosphere that is both refined and welcoming. The formal living and dining rooms, each centered around a cozy fireplace, offer inviting spaces for memorable gatherings and celebrations. The light-filled family room features dramatic volume ceilings, oversized windows, a fireplace, and stunning waterfront views that bring the outdoors in. Designed for both everyday living and effortless entertaining, the gourmet kitchen features slate flooring, stainless steel appliances, a walk-in pantry, and a waterside breakfast area where every meal is paired with breathtaking scenery. The luxurious main-level owner’s suite is a private sanctuary with its own fireplace, spectacular water views, dual walk-in closets with custom built-ins, and a spa-inspired bath designed for relaxation. Upstairs, guests and family are comfortably accommodated with a spacious bedroom suite, two additional guest bedrooms, and a versatile bonus room ideal for a home theater, fitness studio, or playroom. Above the oversized, air-conditioned three-car garage, a separate guest retreat with a kitchenette, full bath, and private balcony with beautiful waterfront views offers the perfect space for visiting friends and family. Outdoor living is equally exceptional. A sprawling slate patio, recently added waterside pool, and enclosed porch with vaulted ceilings and flagstone flooring create inviting spaces to relax, entertain, and take in the serene surroundings. Set on a peninsula with more than 1,000 feet of shoreline, the property offers remarkable privacy and endless water views in seemingly every direction. A private deep water pier on Solitude Creek makes boating effortless and permits a memorable arrival by water for your guests. Enoy fishing and crabbing and direct water access to the Choptank River and Chesapeake Bay. Rarely does a property so gracefully combine timeless architecture, resort-style amenities, and one of Talbot County’s most coveted waterfront settings into a place that truly feels like home.

25610 Chance Farm Ct, Royal Oak

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$369,000
2 Beds ⋅ 1 Baths
Welcome to 5116 Ocean Gateway, a thoughtfully updated rancher in Trappe offering Eastern Shore charm, comfortable one-level living, 1.5 acres, and an exceptional detached workshop and four-car garage. Conveniently located along Route 50, the property provides easy access to Easton, Cambridge, Oxford, St. Michaels, shopping, dining, waterfront destinations, and everyday conveniences, with Ocean City approximately one hour away. From the moment you arrive, the property makes a memorable impression with its established perennial gardens, expansive landscape, flagpole, security doors, new windows installed in 2022, and a brand-new roof completed in 2026. A 12-by-24 hobby shed with an upper storage level provides even more room for lawn equipment, seasonal items, projects, or recreational gear. Inside, a brand-new, fully insulated 225-square-foot sunroom completed in 2026 expands the home’s living space and creates a bright, inviting place to relax, entertain, or enjoy views of the surrounding property throughout the year. A new whole-house split system installed in 2026 provides energy-efficient heating and air conditioning in addition to the home’s existing baseboard heat. The renovated kitchen combines style, character, and everyday functionality with new cabinetry, granite countertops, a farmhouse sink, recessed lighting, a large island with a Boos Block butcher-block countertop, built-in pot filler, range hood, and a brand-new 36-inch Cosmo gas range. A mudroom, pantry, and butler’s pantry add valuable storage and help keep the home organized. The updated bathroom offers a spa-inspired retreat with a soaking tub, dual-sink vanity, built-in shelving, and a spacious walk-in shower with a built-in bench. The standout feature of this property is the hand-built 24-by-36 heated workshop, barn, and four-car garage. Designed for vehicle access, equipment, hobbies, and serious project space, the building features handcrafted 10-by-10 Ipe wood carriage doors, a rear 8-by-7 roll-up garage door, concrete flooring, a water hookup, high-intensity lighting, 120- and 230-volt receptacles, and 120/230-volt electrical service supported by a 60-amp subpanel. The generous layout provides space for multiple vehicles, boat or RV storage, woodworking equipment, tools, recreational gear, or a dedicated creative workspace. With major improvements, flexible storage, an updated one-level home, a beautiful new sunroom, and a substantial four-car garage and workshop, this unique Trappe property offers a rare combination of comfort, land, character, and utility. Schedule your private tour and experience everything 5116 Ocean Gateway has to offer.

5116 Ocean Gateway, Trappe

Listing courtesy of Keller Williams Flagship. Contact:

$324,990
3 Beds ⋅ 3 Baths
August Delivery! Discover the Elmwood, a luxury three-story townhome offering 2,254 square feet of thoughtfully designed living space in Lakeside at Trappe. This move-in ready home features 3 bedrooms, 2.5 baths, and a 2-car garage with a private driveway. The entry level includes a spacious recreation room with direct access to the outdoor patio, providing the perfect space for entertaining or relaxing. The main level showcases an open-concept design where the kitchen, dining area, and Great Room flow seamlessly together. The designer kitchen is appointed with quartz countertops and stainless steel appliances, creating both style and functionality. Upstairs you'll find two secondary bedrooms, a full bath, and a luxurious owner's suite complete with a walk-in closet and private en-suite bathroom. Backing to open green space, this home offers a peaceful setting while providing modern comfort and convenience. Don't miss this opportunity for luxury townhome living at Lakeside at Trappe.

1410 Lake Geneva Dr, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$299,900
3 Beds ⋅ 3 Baths
Welcome to this spacious 3-bedroom, 2.5-bath middle-unit townhome located in Easton. Conveniently situated near shopping, dining, parks, schools, and many of the amenities the town has to offer, this home also provides easy access to major highways for commuters The main living area features a large, combined living and dining room, perfect for everyday living and entertaining. Step outside onto the rear deck for outdoor relaxation and enjoyment. The galley-style kitchen offers ample cabinet space and includes a cozy eat-in area for casual meals. Upstairs, you'll find nearly 1,600 square feet of comfortable living space, including three generously sized bedrooms and two full bathrooms. The lower level offers almost 800 square feet of additional space, providing endless possibilities for storage, a home gym, recreation room. A rear-loading garage adds convenience and extra storage options. Don't miss this opportunity to own a well-located townhome with plenty of space and easy access to everything Easton has to offer.

29595 Dutchmans Ln Unit #603, Easton

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