Orchard Hill Homes for Sale

Orchard Hill Homes for Sale

Welcome to Orchard Hill, a picturesque subdivision nestled in the heart of Chestertown, Maryland. This charming community is located in Kent County, offering residents a peaceful and serene setting to call home.

Orchard Hill is known for its beautiful tree-lined streets, well-maintained homes, and friendly atmosphere. With a variety of architectural styles to choose from, including traditional Colonials and cozy bungalows, there is something for everyone in this sought-after neighborhood.

Homes for sale in Orchard Hill are in high demand, thanks to the community's convenient location, top-rated schools, and proximity to local amenities. Whether you're looking for a starter home, a spacious family residence, or a cozy retirement retreat, you're sure to find the perfect property in Orchard Hill.

Living in Orchard Hill offers residents a true sense of community, with neighbors who quickly become friends and a strong sense of pride in homeownership. From block parties to community events, there are plenty of opportunities to get to know your fellow residents and become a part of this vibrant neighborhood.

If you're looking for a place to call home in Chestertown, look no further than Orchard Hill. With its idyllic setting, charming homes, and welcoming community, this subdivision truly has it all. Come and discover the magic of Orchard Hill – where your dream home awaits.

Newest Orchard Hill Homes for Sale

$439,900
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained 3 bedroom, 2 bath home in the desirable Orchard Hill community! This inviting home features a spacious split-bedroom floor plan that offers both comfort and privacy. The oversized owner's suite is a true retreat, complete with a large walk-in closet and a versatile bonus space that's perfect for a sitting area, home office, or reading nook. Both bathrooms have been completely remodeled with tasteful, modern finishes, adding style and value throughout the home. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, ample cabinetry, a large pantry and plenty of workspace. A full unfinished basement provides endless possibilities for storage or future expansion to suit your needs. For an added piece of mind, the seller has installed a smart water monitoring system with leak detection and automatic shut-off, as well as a new garage door opener. Step outside to enjoy the low-maintenance backyard, where you'll find a beautiful inground saltwater pool surrounded by an expansive concrete patio ideal for relaxing, entertaining, or soaking up the summer sun. Conveniently located with easy access to Route 1, this home is just a short drive from Delaware's award-winning beaches, shopping, dining, and local attractions. Combining modern updates, functional living space, and an exceptional outdoor retreat, this Orchard Hill home is ready for its next owner!

201 Beaufort Ln, Milford

Listing courtesy of Iron Valley Real Estate at The Beach. Contact: (302) 541-8787
$514,900
4 Beds ⋅ 4 Baths
Welcome to 12 E. Green Lane, Milford, DE—a spacious 4-bedroom home designed for comfortable living and effortless entertaining! Step inside to an inviting open-concept floor plan featuring a bright and airy living space that flows seamlessly into the kitchen, complete with stainless steel appliances and plenty of room for gathering with family and friends. The finished basement offers the perfect space for entertaining, whether you're hosting game nights, movie marathons, or creating the ultimate recreation room. Outside, you'll find a large fenced-in backyard that's ready for summer cookouts, family gatherings, and unforgettable backyard parties. With plenty of room for kids, pets, and outdoor fun, this private outdoor space is sure to impress. Conveniently located near shopping, dining, schools, and local amenities, this move-in-ready home offers the perfect blend of space, comfort, and style. Don't miss your opportunity to make 12 E. Green Lane your new home—schedule your private tour today!

12 E Green Ln, Milford

Listing courtesy of Coldwell Banker Realty. Contact: 3022341888
$824,900
5 Beds ⋅ 4 Baths
Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort. Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub. Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath. The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market. Updates to the home are available in Documents

8999 Orchard Dr, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$519,900
5 Beds ⋅ 4 Baths
If you’re looking for a beautiful home with plenty of room to spread out, this is the one! Situated on a prime corner lot, this spacious five-bedroom, three-and-a-half-bath home offers a fenced backyard lined with mature trees for added privacy. Step inside to a stunning setting with 10-foot ceilings, crown molding, a large formal living room and ample windows for natural light. The oversized kitchen is designed for gathering and entertaining, with bar seating, abundant workspace, and two separate dining areas. Just off the kitchen, the second living room features a gas fireplace, creating a comfortable place to relax on cozy evenings. The spacious primary suite includes a vaulted ceiling, walk-in closet, and private bathroom. Upstairs, a large loft provides flexible space for a home office, media room, or additional sitting area. Four more bedrooms and two full bathrooms offer plenty of space for guests, hobbies, or everyday living. The full basement includes a walkout door and provides exceptional storage, along with ample room for a recreation area, home gym, workshop, or craft room. The backyard may be the best part of all. The fenced yard features a large paver patio that is perfect for outdoor dining and entertaining, a firepit for evenings under the stars, and plenty of open space to enjoy. There is also a separately fenced area for dogs. Conveniently located near Bayhealth Hospital, downtown Milford, and Route 1, this home offers easy access to destinations north and south, including Delaware’s popular beaches.

100 Beaufort Ln, Milford

Listing courtesy of Iron Valley Real Estate Premier. Contact: 3027414545
$535,000
5 Beds ⋅ 5 Baths
Handyman Special with Instant Equity Potential! Welcome to 290 Cherry Blossom Drive in Holland, PA, located in highly desirable Northampton Township and the award-winning Council Rock School District. This rare opportunity offers tremendous upside with an estimated ARV well over $850,000+. Situated on nearly one acre, this spacious home features 5 bedrooms, 4.5 bathrooms, and over 3,700 square feet of living space. The main level offers a welcoming foyer, formal living room, spacious dining room, large family room, expansive kitchen with breakfast area, laundry room, full bathroom, powder room, and access to the attached garages. Upstairs, you'll find four generously sized bedrooms and two full bathrooms, including a large primary suite with ample closet space and a private en-suite bath. The finished lower level provides exceptional flexibility with a large recreation room, full bathroom, second kitchen, potential 5th bedroom, and abundant storage space—perfect for extended family, guests, or additional living quarters. An enclosed patio overlooks the expansive backyard, while the oversized driveway and peaceful neighborhood setting add to the home's appeal. Conveniently located near parks, shopping, dining, and major commuter routes, this property combines privacy, space, and value. Being sold strictly as-is. Bring your vision and unlock the incredible potential this property has to offer. Schedule your private showing today before it's gone!

290 Cherry Blossom Dr, Holland

Listing courtesy of KW Empower. Contact: vicki@kwempower.com
$479,500
4 Beds ⋅ 3 Baths
Welcome to your dream home tucked away in the desirable Orchard Hill community! Situated on a premium 0.26-acre cul-de-sac lot, this beautifully maintained 2,900 sq. ft. contemporary colonial perfectly blends spacious living with effortless entertaining. Step inside to find an inviting open-concept layout featuring modern luxury vinyl flooring flowing throughout the main level. The heart of the home is the bright, refreshed kitchen, complete with upgraded countertops, a brand-new central island maximizing counter space, a functional pantry, and a sunny breakfast area—the perfect hub for gathering with friends and family. The spacious living and dining areas flow effortlessly, highlighted by a cozy gas fireplace ideal for chilly evenings. Also on the main level is a dedicated library, providing the perfect space for a home office, reading room, study, or flex space to suit your needs. Upstairs, the expansive owner’s suite serves as a true private retreat, complete with a walk-in closet and a luxurious en-suite bathroom featuring a double vanity and a deep soaking tub. Three additional generously sized bedrooms and a meticulously updated guest bath provide plenty of room for family, guests, or a home office. The outdoor space is an entertainer’s paradise, boasting a fully vinyl-fenced backyard and a custom patio designed for weekend barbecues or quiet, secluded relaxation. Need storage or room to expand? The massive full, unfinished basement offers endless possibilities for a home gym, workshop, or future recreation room. Complete with a true 2-car garage and an expanded driveway, this move-in-ready gem offers unparalleled convenience. Ideally located just minutes from historic downtown Milford, residents enjoy easy access to shopping, dining, and medical facilities. Commuters will appreciate the convenient drive to Dover Air Force Base, while beach lovers are just a straight drive away from Delaware’s premier coastal destinations. Don't miss your chance to own this exceptional home—schedule your tour today!

6 Costabella Ct, Milford

Listing courtesy of Keller Williams Realty. Contact: (302) 856-1458
$445,000
4 Beds ⋅ 3 Baths
Owned solar panels will be paid off at settlement, allowing the new owner to enjoy a system designed to offset up to 100% of annual electric usage. Built by Riverview Builders, this 4-bedroom, 2.5-bath Hampton model offers over 2,500 square feet of thoughtfully designed living space, plus an insulated unfinished basement ready to fit your needs. Step inside to a welcoming foyer where French doors open to a private home office. The open-concept main level features 9-foot ceilings, a spacious family room, and a beautifully appointed kitchen with granite countertops, a walk-in pantry, and plenty of room to gather. Upstairs, you'll find the convenience of second-floor laundry, a spacious primary suite with two walk-in closets and a private bath, along with three additional generously sized bedrooms. Out back, relax and enjoy peaceful golf course views. Conveniently located between Route 1 and Route 113, this home offers the perfect combination of space, efficiency, and location.

121 W Green Ln, Milford

Listing courtesy of Keller Williams Realty Central-Delaware. Contact: 3026770020
$524,998
5 Beds ⋅ 4 Baths
✨ Outstanding 5-Bedroom Home in Orchard Hills ✨ Welcome to this exceptional 5-bedroom, 3.5-bath and full rough in for another bathroom in the basement in the highly sought-after Orchard Hills community. Since 2021, this home has been extensively updated with: Fresh paint throughout New LVP flooring on both levels Updated banisters A brand-new full bathroom upstairs that's like going to a high-end spa! New siding and shutters for enhanced curb appeal 🌟 Curb Appeal & Outdoor Living A large, paved entrance leads you to the front door, complemented by a gorgeous paver patio. Out back, enjoy another paved patio with a built-in fire pit—perfect for relaxing or entertaining. 🏡 Interior Highlights Two primary suites one on each floor! Main-level suite for convenience and comfort Upstairs suite with private full bath, ideal for guests or multi-generational living A grand foyer welcomes you in Versatile flex room (home office, study, or playroom) Elegant formal dining room flowing into the kitchen Formal living room with cozy fireplace 🍴 Gourmet Kitchen Features High-end stainless-steel appliances Striking tile backsplash Granite countertops & premium cabinetry Spacious center island Bright sunroom with walk-out to the patio 🛏 Upstairs Retreat Four spacious bedrooms with generous closet space, including the impressive second primary suite. 🔨 Additional Features Expansive unfinished basement with full rough-in plumbing, framing, and walk-out—ready to customize Finished garage with sleek epoxy floors Solar panels installed in 2022 (transferable to approved buyer) 💎 Well-Maintained This home has been extremely well cared for. With thoughtful updates, two primary suites, and incredible living space, this Orchard Hills beauty is truly one-of-a-kind. Don’t wait—schedule your private tour today!

26 E Green Lane, Milford

Listing courtesy of Iron Valley Real Estate Premier. Contact: 3027414545
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