Orchard Hill Homes for Sale

Orchard Hill Homes for Sale

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Orchard Hill and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

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Newest Orchard Hill Homes for Sale

8986 Orchard Dr, Chestertown
$679,900
3 Beds ⋅ 4 Baths
COMING SOON! Welcome to 8986 Orchard Drive, tucked away in the sought-after Orchard Hill neighborhood just outside of Chestertown! This move-in-ready home offers comfortable one-level living with 3 bedrooms, 2 bathrooms, and a partially finished basement with endless possibilities. Enjoy a spacious living room with recessed ceilings, an inviting primary suite with a jetted soaking tub, and updates throughout, including a new roof in 2025 and an efficient HVAC system upgraded in 2022. The partially finished basement features a private, ground-level walkout entrance, studio-style living space with a pool table, an efficient mini-split system, and plenty of additional storage or workshop space. French drains and an automatic sump pump add peace of mind. Outside, enjoy multiple spaces to relax and entertain, including a screened-in porch, open deck, patio with a hot tub that conveys, and a partially fenced backyard surrounded by beautiful crepe myrtles. Additional highlights include a two-car garage, a large floored attic for extra storage, and a solar system installed in August 2025. Conveniently located within 10 minutes of Chestertown's everyday amenities, shopping, dining, and more, this property offers the perfect blend of comfort, flexibility, and convenience. Come see all that this home has to offer! **Interiors pics available on 10/14**

8986 Orchard Dr, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact:

6252 Dawn Day Dr, Columbia
$575,000
4 Beds ⋅ 3 Baths
Recently updated Colonial-style single-family residence offering 4 bedrooms, 2.5 bathrooms, and 2,124 finished square feet in established Orchard Hill. Nearly $10,000 in 2026 improvements include exterior updates such as shutter repairs, added exterior lighting, and cleaning, along with select interior paint, updated light fixtures, recently installed carpet, two handrails on all stairs, and more. Additional improvements include the HVAC system and attic insulation in 2017, updated bathrooms in 2017, and a water heater installed in 2024. // Distinctive geometrical doorways add character throughout the main level, beginning in the welcoming foyer featuring updated lighting. A carpeted formal living room flows into the freshly painted formal dining room, accented by a chair rail molding and an updated light fixture. The main level also offers a convenient powder room and an inviting family room centered around a brick-accented wood-burning fireplace with direct access to the deck. // The charming eat-in kitchen features stainless steel appliances installed in 2021, quartz countertops, white Shaker-style cabinetry, a custom backsplash, updated lighting, a pantry, and a cozy breakfast area highlighted by a custom Pella® greenhouse window. // Upstairs, four newly carpeted bedrooms are accompanied by two full bathrooms. The owner’s suite includes a walk-in closet and a private ensuite bathroom. // The fully finished, waterproofed walk-up lower level (2025) expands the living space with a spacious recreation room and two freshly painted bonus rooms ideal for a home office, playroom, hobby space, or other flexible uses. A separate storage room with laundry completes the lower level. // Outdoor living continues on the deck, where a tall guardrail adds privacy while overlooking the spacious backyard, accented by a mature tree. Lush landscaping enhances the front exterior, which also features a private driveway leading to an attached 1-car garage with a freshly painted floor.

6252 Dawn Day Dr, Columbia

Listing courtesy of Keller Williams Lucido Agency. Contact:

602 Saint Johns Rd, Shiremanstown
$299,900
3 Beds ⋅ 3 Baths
Welcome home to this freshly updated single-family residence in the heart of Shiremanstown! Conveniently located in the highly desirable Mechanicsburg School District, this 3-bedroom, 2.5-bath home offers the perfect blend of comfort and convenience. The thoughtfully designed floor plan features a spacious first-floor primary suite, providing easy one-level living. Enjoy the added benefit of an attached carport for off-street parking, along with fresh updates that make this home move-in ready. Just minutes from shopping, dining, parks, and major commuter routes, this centrally located property offers everything you need in a place you'll love to call home. Schedule your private showing today!

602 Saint Johns Rd, Shiremanstown

Listing courtesy of Keller Williams of Central PA. Contact:

12 E Green Ln, Milford
$489,900
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:

6 Costabella Ct, Milford
$469,500
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:

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