Middletown Homes for Sale

Discover Your Dream Home in Stephens City/Winchester! Choose from five wooded homesites, each offering over 2 acres of privacy and natural beauty. With six available floor plans, there’s a home to fit every lifestyle, including main-level living designs, main-level owner’s suite plans, traditional two-story homes with four bedrooms upstairs, and homes featuring a main-level in-law suite. Our Dogwood floor plan is Priced

Ridings Mill Road, Stephens City

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$695,000

3 Beds ⋅ 2 Baths

Discover Your Dream Home in Stephens City/Winchester! Choose from five wooded homesites, each offering over 2 acres of privacy and natural beauty. With six available floor plans, there’s a home to fit every lifestyle, including main-level living designs, main-level owner’s suite plans, traditional two-story homes with four bedrooms upstairs, and homes featuring a main-level in-law suite. Our Evergreen floor plan is Priced

Ridings Mill Road, Stephens City

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$895,000

4 Beds ⋅ 4 Baths

Discover Your Dream Home in Stephens City/Winchester! Choose from five wooded homesites, each offering over 2 acres of privacy and natural beauty. With 7 available floor plans, there’s a home to fit every lifestyle, including main-level living designs, main-level owner’s suite plans, traditional two-story homes with four bedrooms upstairs, and homes featuring a main-level in-law suite. Our Huntwick Farm floor plan is Priced

Ridings Mill Road, Stephens City

Listing courtesy of Pearson Smith Realty, LLC. Contact:

$800,000

4 Beds ⋅ 3 Baths

Middletown Icon - Introducing a truly distinctive property where timeless stone architecture meets exceptional versatility! A unique opportunity to capture a piece of Middletown - the proud new owner will appreciate "3 Stone Beauties"! 503 S. Broad; your 4 bdrm/2.5 baths Colonial. 505, your 4 car detached garage. 507 S. Broad; your lovely stone cape cod with a fenced in yard! 3 Parcels being sold together.

503 S Broad St, Middletown

Listing courtesy of RE/MAX Advantage Realty. Contact:

$650,000

4 Beds ⋅ 4 Baths

A HOME THAT MAKES EVERYDAY LIFE FEEL GOOD! Some homes impress you with features. 303 Cone Branch wins you over with the way it lives. Warm, comfortable, and just steps from Middletown Park and walking trails, this custom-built Admar home offers 3,274 finished square feet, four bedrooms, three full and one half baths, a large, flat .35-acre lot in Foxfield, and sought-after Middletown schools. A STATELY WELCOME. Step inside and you’ll find something increasingly hard to find in newer construction—a true formal foyer with a beautiful oak staircase, giving this classic Colonial a gracious sense of arrival. Oak hardwood floors continue through the foyer, living room, and large dining room, while a private first-floor office with doors just off the entry gives you dedicated work-from-home space without sacrificing a bedroom. THE HEART OF THE HOME. Move toward the back of the home, and everything opens up. This is where the house really comes to life. The kitchen and sunken family room create one warm, light-filled gathering space—the kind of place where someone is cooking at the island, someone else is curled up by the fire, and everyone can still be together. Tall windows bring in beautiful natural light, while hickory hardwood floors add warmth through both spaces. The kitchen features granite countertops, a tile backsplash, a center island, and KitchenAid appliances, including the dishwasher, microwave, and range replaced in 2020. Just a step down, the family room invites you to settle in with a floor-to-ceiling wood-burning fireplace, custom Roman blinds, and built-ins on either side. From quiet nights by the fire to a house full of family and friends, it’s easy to imagine life happening here. SPACE FOR REAL LIFE. With 2,444 finished square feet above grade, there is plenty of room to spread out. All four bedrooms are generously sized, including the spacious primary with its private en-suite bath, while the main-level laundry room adds everyday convenience. A LOWER-LEVEL IN-LAW SUITE. The finished lower level adds another 830 square feet and tremendous flexibility. Designed as an in-law suite, it offers its own kitchen, full bath, private side entrance, living space, and workshop, plus an impressive amount of storage—wonderful for extended family, guests, hobbies, or simply another comfortable living area. OUTDOOR SPACES THAT FEEL LIKE EXTRA ROOMS. The sellers’ favorite spot is the large, deep front porch. Shaded and welcoming, it feels like another room—a place for rocking chairs, morning coffee, a good book, or an evening glass of wine as neighbors stroll by. A wooded area across the street adds a peaceful view while still keeping you connected to the neighborhood. Out back, mature landscaping creates a wonderful sense of privacy. The large, flat, aluminum-fenced yard is highlighted by a beautiful red leaf maple, while the rear deck with a Sunsetter power retractable awning creates another outdoor room for dining, entertaining, or relaxing in the shade. A long driveway provides plenty of parking. MIDDLETOWN PARK IS JUST STEPS AWAY. This is one of those locations where the community becomes an extension of home. Middletown Park and the walking trails are literally just steps away, making morning walks, afternoons at the park, and time outdoors an easy part of everyday life. Set on a non-through street near the cul-de-sac, you’ll enjoy a quieter neighborhood feel while staying connected to the heart of Middletown. Walk toward Main Street for local restaurants, shops, and community events, with Safeway and CVS also nearby. A 2018 roof, 2015 HVAC, 400-amp electrical service, and updated KitchenAid appliances add practical value behind the scenes. 303 Cone Branch gives you the best of both worlds—the stately character and defined spaces of a classic Colonial paired with the warm, light-filled gathering spaces buyers love today.

303 Cone Branch Dr, Middletown

Listing courtesy of RE/MAX Results. Contact:

$309,900

3 Beds ⋅ 2 Baths

If you're looking for an updated home with just under 1 acre of land with plenty of privacy.... look no further! Home is in Lower Dauphin SD and boarders State Game Land. You wont have to worry about any nighbors behind you. Come see the updated ranch home, one floor living, new kitchen, new bathrooms new flooring and so much more. Home has 3 bedrooms, 2 full bathrooms, oversized two car garage and almost 1 acre of land. Still plenty of time to enjoy your summer nights on the deck. Home is located in quiet, wooded area but still has great access to rt 283 and pa turnpike. Come see for yourself!!!

1384 Roundtop Rd, Middletown

Listing courtesy of Coldwell Banker Realty. Contact:

$1,250,000

6 Beds ⋅ 4 Baths

The Dr. Dorsey Lewis House — A Middletown Landmark! One of Middletown's most distinguished historic manor residences, this magnificent Colonial Revival home occupies nearly an acre in the heart of town. An expansive, columned front porch welcomes you into a grand center hall, generously proportioned rooms, beautiful hardwood floors, rich architectural details, and multiple fireplaces. Offering six bedrooms and three full and one half baths, the residence was featured as a 2011 Decorator Show House. Outside, a private backyard oasis features an in-ground swimming pool, spa, inviting patios, and mature landscaping. An extraordinary collection of outbuildings includes a detached two-car garage, a 14-bay carriage building, and a 2,700-square-foot detached pole-building currently serving as a decorator/retail storefront with its own six-car parking lot. Lovingly maintained by its current owners, this remarkable estate offers a rare opportunity to become the next steward of a treasured piece of Middletown history. Truly one of a kind and nearly impossible to replicate today!

217 N Broad St, Middletown

Listing courtesy of Patterson-Schwartz-Hockessin. Contact:

$42,000

2 Beds ⋅ 1 Baths

69 Caravan Ct, Middletown

Listing courtesy of KW Greater West Chester. Contact:

$250,000

3 Beds ⋅ 1 Baths

INVESTOR SPECIAL! Fixer Upper with a separate lot! .16 Ranch Home and .08 Adjacent Lot.

313 Jefferson St, Middletown

Listing courtesy of RE/MAX Advantage Realty. Contact:

$535,000

3 Beds ⋅ 1 Baths

Perfect time to settle in before the holiday season! Start your mornings with coffee on the deck, surrounded by peaceful, pasture-like views and a gentle breeze. This well-built all-brick 3-bedroom rancher sits on a beautiful 2.08-acre lot and offers easy one-level living, an attached two-car garage, and exceptional storage throughout. Wood floors on the main level, gas fireplace in living room and wood fireplace in lower level, French doors with built in shades in dining room allows for generous natural sunlight to filter through. The owners have thoughtfully completed numerous upgrades over the years while fully enjoying everything this special property has to offer. The full bathroom offers a double vanity with generous counter space, a deep linen closet with shelving and a laundry chute that drops next to the laundry area in the lower-level making that task a bit easier. The lower level provides additional flexibility, currently arranged with a comfortable living area featuring a wood stove, along with a separate storage area with auto-fan for ventilation. 2 mini split units to heat and cool the space .With its generous layout and exterior access through a French door with built-in shades and extra-wide steps to the backyard, this space can be easily reimagined to suit your needs. Outside, the setting truly shines. Meander through the lovely garden, where seasonal color, beautiful plantings, a charming potting shed, and a stepping-stone path create a serene place to relax and explore. Continue a bit farther to discover the 56x36 pole barn with electricity and water, once used for horses, offering even more possibilities for hobbies, plenty of storage for your tractor, lawn equipment, etc) or whatever suits your needs.

8922 Mount Tabor Rd, Middletown

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

$268,000

3 Beds ⋅ 2 Baths

**All the updates, none of the projects!** Welcome to 312 Elizabeth Street, a beautifully updated 3-bedroom, 2-full-bath ranch in the heart of Middletown and the Appoquinimink School District! From the ALL NEW stainless steel kitchen appliances to the NEW ROOF and NEW SIDING, the improvements have already been made so you can simply move in and enjoy. Inside, you'll find durable laminate flooring, an updated kitchen, a private primary bathroom, and a refreshed hall bathroom featuring a brand-new tub. Step outside to enjoy the spacious deck, oversized driveway, and convenient backyard storage shed. Whether you're purchasing your first home or looking to simplify your lifestyle, this move-in-ready property delivers modern updates, practical living, and the convenience of single-level living. Come see why buyers are raving about the condition of this home! Mortgage savings may be available for buyers of this listing.

312 Elizabeth St, Middletown

Listing courtesy of Redfin Corporation. Contact:

$658,139

3 Beds ⋅ 2 Baths

Discover an exceptional opportunity to embrace a luxurious lifestyle in this stunning new construction home, nestled within the exclusive Parks Edge at Bayberry, Middletown's 55+community. Set to be completed in 2026, this exquisite detached ranch-style home features three spacious bedrooms and two full bathrooms, providing ample space for relaxation and entertaining. The architectural design reflects a modern aesthetic, while the high-end construction materials promise durability and sophistication. With an expansive lot size of 0.29 acres, you'll enjoy a sense of privacy and tranquility in your own personal oasis. Step inside to discover a thoughtfully designed layout that maximizes both space and natural light. The unfinished basement presents a blank canvas, allowing you to customize it to your liking-whether it be a cozy den, a home gym, or additional storage. The attached two-car garage, complete with a garage door opener, offers convenience and security for your vehicles. As a resident of this vibrant community, you'll have access to a range of exclusive amenities, including a community clubhouse and pool that invites you to unwind and socialize with neighbors. The surrounding area is perfect for leisurely strolls, fostering a sense of camaraderie among residents who appreciate an active and engaging lifestyle. This property is not just a house; it's a place to call home, where luxury meets comfort in a welcoming environment. The meticulous attention to detail in the design and construction ensures that every corner of this residence exudes quality and style. Imagine hosting gatherings in your spacious living areas or enjoying quiet evenings on your patio, surrounded by the beauty of your new community. Don't miss the chance to be part of this extraordinary living experience. With its prime location, luxurious features, and a focus on an exclusive lifestyle, this home is poised to become a cherished retreat for those seeking the best in life. Embrace the opportunity to create lasting memories in a place that truly feels like home.

2901 Mailly Davis Ct, Middletown

Listing courtesy of Blenheim Marketing LLC. Contact:

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