Middletown Homes for Sale

Middletown Homes for Sale

Welcome to Middletown, a charming gem nestled in the heart of the United States! This vibrant city offers a delightful blend of small-town warmth and modern conveniences, making it an ideal place to call home. With its rich history, friendly community, and beautiful parks, Middletown is perfect for families, professionals, and retirees alike.

Middletown boasts a variety of homes for sale, catering to diverse lifestyles and preferences. Whether you’re looking for a cozy bungalow, a spacious family home, or a contemporary townhouse, you’ll find an array of options that fit your needs. Many properties feature beautiful landscaping, updated interiors, and easy access to local amenities. The real estate market here is thriving, offering opportunities for first-time buyers and seasoned investors alike.

The city is known for its excellent schools, making it a top choice for families seeking quality education for their children. Outdoor enthusiasts will love the numerous parks and recreational areas that offer trails for hiking, biking, and picnicking. Additionally, Middletown's vibrant downtown area is filled with charming shops, restaurants, and cultural attractions, providing a lively atmosphere for residents to enjoy.

With its welcoming community spirit and a wide range of housing options, Middletown truly has something for everyone. If you’re considering a move to this delightful city, now is the perfect time to explore the homes for sale and discover your dream home in Middletown. Let the adventure begin!

Newest Middletown Homes for Sale

$649,340
5 Beds ⋅ 3 Baths ⋅ DENC2112052 MLS
Quick Delivery 5 bedroom home in Appoquinimink school district. READY BY THE END OF THE YEAR. This lovely home offers a 1st floor full bath with bedroom/office space, and the remaining 4 beds and 2 baths upstairs. The Charleston floor plan offers a well crafted layout with walk-in pantry, butler's pantry, switchback staircase, and much more. Quality products like Hardie Plank Siding, Timbertech front porch, and Anderson windows add to the fine construction by this local, semi-custom builder (Benchmark Builders). Check in at the model home during business hours for a tour and more information.

1621 Schwinn St, Middletown
$649,000
4 Beds ⋅ 4 Baths ⋅ MDFR2089606 MLS
Welcome to 7312 Countryside Circle, set on 2.54 acres in Middletown. This 4-bedroom, 3.5-bath home offers approximately 2,116 square feet above grade plus a finished lower level, creating plenty of flexibility for everyday living. The main level features comfortable gathering areas, while four bedrooms provide room for family, guests, or a home office. Downstairs, the finished lower level offers even more possibilities for a family room, gym, playroom, hobbies, or entertaining. Outside, the yard gives you room to garden, play, entertain, or simply enjoy the property and its peaceful surroundings. Served by well and septic, this home offers a more private setting while still being convenient to everyday necessities. Enjoy all that Middletown has to offer, including local restaurants, shops, parks, and schools, with Downtown Frederick just a short drive away. Easy access to Route 40A, Route 17, I-70, I-270, and Route 15 makes getting around Frederick County and commuting toward Montgomery County and the D.C. area convenient. If you’re looking for acreage, a versatile floor plan, and a Middletown location that keeps you connected without sacrificing breathing room, this one is worth a look.

7312 Countryside Cir, Middletown
$749,900
5 Beds ⋅ 4 Baths ⋅ DENC2111960 MLS
This is a one of kind historic home with an incredible amount of space and very impressive updates! Welcome to 26 South Main Street, a 5 bedroom 4 bathroom victorian home that has the charm and character of a historic home along with major updates and convenience of a newer home. The sellers have thoughtfully updated just about everything you could imagine - the major systems, the roof, piping and electrical. They worked alongside a licensed engineer and architect to create the perfect space and added even more square footage on to this already large home by adding the den off of the kitchen which leads to a covered deck and the primary suite was remastered with a sitting room, more closets than you can imagine and a deck that overlooks the C&D canal. It is stunning! When you walk through this home you will see that these aren't just every day improvements. They had almost every piece of woodwork replaced with matching moldings, the baseboards were stripped and restained, all floor joists have been secured, all corners enhanced with steel braces and the sheetrock was upgraded to 5/8 inch to comply with bed and breakfast standards. They not only had the HVAC updated but chose geothermal heat pumps. The gorgeous wood windows were rebuilt with storm windows to create efficiency while maintaining the home's historic beauty. This home has surprises around every corner and shows very well. The lot is just under 1/2 acre offering plenty of space for entertaining outside while enjoying the views of the canal. Just minutes from Route 1, this location cannot be beat!

26 S Main St, Middletown
$535,000
3 Beds ⋅ 3 Baths ⋅ DENC2111980 MLS
Back on the market, NO FAULT of SELLER. Here is your second chance at this perfect home at an attractive price. Why wait for new construction when you can own this beautifully maintained, just 4-year-old ranch home situated on a premium lot backing to peaceful open space? Located in the highly desirable 55+ active adult community of The Preserve at Deep Creek, you'll enjoy resort-style amenities including a clubhouse, fitness center, swimming pool, pickleball courts, walking paths, and open green space. Even better, lawn maintenance and snow removal are included, allowing you to spend more time enjoying life and less time on home maintenance. From the moment you step inside, you'll appreciate the bright, open floor plan featuring 9-foot ceilings and luxury vinyl plank flooring that flows throughout the foyer, kitchen, and great room. Designed for both everyday living and entertaining, the gourmet kitchen is the gathering space of the home and boasts a large center island with seating and pendant lighting, 42-inch cabinetry, gorgeous countertops, tiled backsplash, stainless steel appliances, gas cooking, a vented range hood, and upgraded LED lighting. The spacious dining area easily accommodates a large table and opens through sliding glass doors to the enclosed porch, creating a seamless indoor-outdoor living experience. The inviting great room provides the perfect space for entertaining, while the private owner's suite offers a relaxing retreat complete with a tray ceiling, crown molding, ceiling fan, walk-in closet, and a beautifully appointed en-suite bath featuring dual vanities, upgraded cabinetry, tile flooring, and a large tiled shower. Two additional generously sized bedrooms, a full hall bath, a convenient laundry room, and a practical mud space area just off the garage complete the main level. Step outside and discover one of this home's standout features—the enclosed porch overlooking scenic open space, making it the perfect spot to enjoy your morning coffee or unwind in the evening. Just beyond, the maintenance-free composite deck with its spacious gazebo/pergola provides an ideal setting for outdoor dining, entertaining, BBQs, or simply relaxing while taking in the peaceful backyard views. The finished lower level dramatically expands your living space and offers endless possibilities for a recreation room, media room, home office, fitness area, or hobby space. A full bathroom and an expansive unfinished storage area provide exceptional flexibility and convenience. Additional upgrades include a tankless water heater, irrigation system, security alarm, and an attached two-car garage. Conveniently located just minutes from grocery stores, restaurants, parks, shopping, Christiana Care's emergency facility, and major highways, this exceptional home combines modern comfort with an unbeatable location. If you're looking for a move-in ready home with outstanding amenities and truly maintenance-free living, this one checks every box. Schedule your private tour today and experience everything this exceptional home has to offer!

272 Anglesey Dr, Middletown
$519,000
3 Beds ⋅ 3 Baths ⋅ DENC2111750 MLS
Welcome to 420 Winterberry Dr. in Four Seasons at Silver Maple Farms, where the ease of low-maintenance living meets the space, privacy, and flexibility of a detached home. A beautiful tree-lined entrance introduces this thoughtfully designed community, where mature landscaping, well-spaced homes, walking trails, and frequent seating areas create a tranquil setting. The community offers a pool and clubhouse along with a wide variety of resident-organized clubs and activities, including mahjong, poker, sewing, book clubs, and more. Lawn cutting, snow removal, and common-area maintenance are included through the community association, offering the convenience of a low-maintenance lifestyle while allowing homeowners to retain their own yard, outdoor spaces, and privacy. Located in Middletown, 420 Winterberry Dr. offers access to major routes including I-95 and Route 1, while remaining close to shopping, the Delaware River, and the area's more relaxed surroundings. The combination of accessibility and a beautifully established community setting adds to the appeal of the location. Inside, this Magnolia by K. Hovnanian features the optional rear sunroom and third bedroom, creating additional flexibility within the main level. The mostly finished basement adds even more usable space, including a full bathroom and abundant storage. Outside, the oversized composite deck provides an inviting extension of the living space—whether you're grilling, hosting a crab feast, enjoying an outdoor meal, or simply taking in the peaceful surroundings. A front porch overlooking the mature trees offers another place to slow down and enjoy the setting. At 420 Winterberry Dr., the combination of a flexible floor plan, substantial finished and unfinished space, outdoor living areas, and the amenities and maintenance conveniences of Four Seasons at Silver Maple Farms creates a property with plenty of room to make the space your own.

420 Winterberry Dr, Middletown
$599,900
4 Beds ⋅ 3 Baths ⋅ DENC2112006 MLS
Welcome to 106 Marley Road, spacious 4 bedroom, 2 1/2 bath quality Stover built home with owned solar panels, 3 car turned garage plus finished basement on a large 1.45-acre lot and located within the award winning Appoquinimink School District! Covered front porch leads to grand 2 story foyer with 3/4 inch cherry hardwood flooring leading through the living room, dining room, and includes 9' ceilings throughout the first floor plus a first-floor office. Eat-in kitchen features tile flooring, 42" cabinets, breakfast bar and pantry. Sliders lead to patio overlooking a gorgeous, flat, fenced lot with apple trees, blueberry bush patch, blackberries, red raspberries and a fig tree. The kitchen opens to a light-filled family room with gas fireplace, vaulted ceiling and skylights. Convenient first floor laundry! Upstairs you will find the primary suite with 2 walk-in closets plus sitting room and en-suite 4 piece bath. The finished basement adds extra living space—currently a rec room and exercise room plus storage. Hurry to schedule your private tour today!

106 Marley Rd, Middletown
$683,500
5 Beds ⋅ 4 Baths ⋅ DENC2111858 MLS
Ready for a simpler lifestyle but not ready to sacrifice the space and comforts you love? Welcome to 646 Swansea Drive in the desirable 55+ community of Preserve at Deep Creek. Situated on a premium lot backing to open space that will not be developed and with over 4,525 finished square feet, 5 bedrooms and 4 full baths, this beautifully maintained Craftsman-style home makes it possible to right-size your lifestyle without feeling like you're downsizing your home. Enjoy the convenience of main-level living while keeping all the extra space you've grown accustomed to. The first floor features a spacious primary suite with a sitting area and private bath, a second bedroom and full bath, home office and main-level laundry. The gourmet kitchen with center island and pantry opens to generous living space accented by a gas fireplace—ideal for everything from quiet evenings at home to holiday gatherings and entertaining. And there's no need to give up room for family and guests. Upstairs you'll find two additional bedrooms and a full bath, while the partially finished lower level offers another bedroom, full bath and an expansive 26' x 24' family room—perfect for guests, hobbies, movie nights or extended stays. There's even a remarkable 38' x 35' storage room, so moving here doesn't mean parting with everything you've collected over the years. A 2-car garage with additional storage, extensive hardscaping, and a community pool complete the package. Your lawn care needs are completely taken care of with the community lawn cutting and an irrigation system in place for a lush green lawn! This is downsizing without the sacrifice—less to worry about, but plenty of room to live, entertain, host family and keep the things that matter most. 646 Swansea Drive offers the space of a substantial home with the convenience and lifestyle many buyers are looking for in their next chapter. In addition to this home being 8 years young, the seller is offering a 1-year home warranty for assurance and ease of mind.

646 Swansea Dr, Middletown
$585,000
5 Beds ⋅ 3 Baths ⋅ DENC2111918 MLS
Village of Bayberry North Colonial ideally situated across from a lush community park and just one block from the beautiful neighborhood lake. This spacious, move in ready 5 bedroom 2 1/2 bath home offers more than 3,000 finished square feet of comfortable living space. The main level features a welcoming kitchen with granite countertops, stainless steel appliances, and a large breakfast bar that opens to the generously sized family room—an ideal space for relaxing with family or entertaining guests. A separate dining room and flexible living room/office provide additional room for gatherings, work, or everyday living. Upstairs, you’ll find four bedrooms, including a spacious owner’s suite, along with a bright, conveniently located laundry room. The finished basement adds even more versatility with a large recreation room and a fifth bedroom featuring an egress window. Enjoy outdoor living in the backyard, complete with a large patio and hardscaped fire-pit area—perfect for entertaining or unwinding. A two-car garage offers vehicle protection and additional storage, while the expansive driveway provides plenty of off-street parking. Bayberry North offers an exceptional community lifestyle with three playgrounds, tree-lined streets, walking paths, picnic pavilions, and a well-stocked community lake. Residents also enjoy access to a beautiful lake house available for community and private events. Conveniently located near shopping, restaurants, and the Appoquinimink School District, this home presents a wonderful opportunity to enjoy comfortable living in a thoughtfully planned and highly desirable community.

1173 S Olmsted Pkwy, Middletown
$499,900
4 Beds ⋅ 2 Baths ⋅ MDFR2089766 MLS

7217 Picnic Woods Rd, Middletown
$344,900
4 Beds ⋅ 4 Baths ⋅ PADA2064520 MLS
Welcome to 1460 Woodridge Drive, a beautiful single-family home located in the desirable Woodridge community within the Middletown Area School District. Situated on a quiet 0.26-acre lot, this 4-bedroom, 4-bathroom residence offers over 2,150 square feet of finished living space, including a fully finished walkout basement. Key upgrades provide some peace of mind, including a complete roof replacement in 2010, replacement windows installed in 2012 and 2016, new gutters in 2019, a newer water heater installed in 2018, and a recently serviced electric heat pump system (June 2026). Enjoy low-maintenance living with a modest HOA fee of just $35 quarterly. Conveniently located near local parks, school campuses, and major commuter routes including PA-283 and PA-441, this well-maintained home is completely move-in ready!

1460 Woodridge Dr, Middletown
$479,000
3 Beds ⋅ 2 Baths ⋅ VAFV2045112 MLS
Sprawling 20-acre property in a great location with easy access to I-81, I-66, and Main Street in Middletown. This property offers a fantastic investment opportunity with plenty of potential to renovate the existing home and make it your own. The modular home features 3 bedrooms and 2 bathrooms, with a basement offering additional space that could be finished for even more usable living area. With ample acreage and a convenient location, this property offers plenty of possibilities for investors, builders, or buyers looking for space and potential.

797 S Buckton Rd, Middletown
$550,000
3 Beds ⋅ 3 Baths ⋅ DENC2111700 MLS
Some homes simply check the boxes; this one delivers the lifestyle you’ve been waiting for—beautifully designed spaces, effortless one-level living, and an exeptional setting in The Legends at Frog Hollow. This thoughtfully crafted and carefully maintained ranch homes offers causal elegance and an inviting open-concept design. The vaulted great room features gleaming hardwood floors and a gas fireplace, flowing seamlessly into the classic formal dining room and spacious kitchen with crisp white cabinetry, granite countertops, center island, and cozy breakfast nook - the perfect place for morning coffee. The versatile four-season sunroom leads to the private E.P. Henry patio for indoor and outdoor entertaining or relaxing with a good book. The primary suite provides a restful retreat, complete with a huge walk-in closet and luxurious en-suite bath featuring a jetted tub, walk-in shower, and double vanity. Two additional bedrooms and a full bath provide comfortable accommodations for family or guests. The finished lower level adds more than 1,000 square feet of flexible living space with a second gas fireplace - ideal for a media room, home gym, hobbies, home office, recreation or entertaining - pool table included! A large unfinished room provides abundant storage. Other highlights include a two-car garage, new HVAC, new water heater, and a new roof installed in 2016. Ideally situated on a quiet cul-de-sac and surrounded by the amenities of The Legends, including Frog Hollow Golf Club, a public links-style 18-hole championship course, and The Edge 18 swim club & venue featuring a pool, pool house, tennis courts, playground, and ballroom/special event space for arts, fitness, and recreation, all just around the corner - then walk over an enjoy dinner or drinks with friends at The Pub at Frog Hollow. Discover The Legends—more than an address, it's a lifestyle.

1 Weiskopf Cir, Middletown
Start Your Search