Middletown Real Estate

Middletown Real Estate

Welcome to Middletown, a charming gem nestled in the heart of the United States! Known for its friendly atmosphere and vibrant community, Middletown offers a delightful blend of small-town charm and modern conveniences. This picturesque city is ideally situated, providing easy access to both urban amenities and serene natural landscapes, making it a perfect place for families, professionals, and retirees alike.

Middletown boasts a rich history that is reflected in its beautifully preserved architecture and cultural landmarks. Stroll through the historic downtown area, where you’ll find an array of boutique shops, cozy cafes, and delightful restaurants that cater to every palate. The local farmers' market is a must-visit, showcasing fresh produce and artisanal goods from the surrounding region, allowing residents to support local farmers while enjoying the best of what Middletown has to offer.

Outdoor enthusiasts will appreciate the abundance of parks and recreational opportunities available throughout the city. Whether you enjoy hiking, biking, or simply relaxing in nature, Middletown’s scenic trails and green spaces provide the perfect backdrop for your outdoor adventures. The community is also home to several annual events and festivals that celebrate the local culture, fostering a strong sense of belonging among residents.

With a variety of housing options, from quaint single-family homes to modern condos, Middletown is an ideal place to settle down. The city’s excellent schools, low crime rates, and welcoming neighborhoods make it a top choice for families looking for a safe and nurturing environment.

Explore the charm of Middletown today and discover why so many are proud to call this city home!

Newest Listings in Middletown

$739,990
3 Beds ⋅ 4 Baths
Brand New 55+ Community in Middletown, DE Welcome to the Carver, a beautifully designed home that combines an open-concept layout with plenty of natural light. Scheduled for settlement in October 2026, this home offers 3 bedrooms, 3.5 baths, and a 2.5-car garage, providing a comfortable blend of style and functionality. A welcoming front porch creates charming curb appeal, while the screened deck offers an inviting space to enjoy the outdoors. Inside, the finished basement provides additional living space, and a fireplace adds warmth and character to the main living area. The spacious kitchen features a huge island and quartz countertops, perfect for cooking, gathering, and entertaining. Laminate flooring throughout the first floor offers a cohesive and stylish finish, while the bathrooms feature a walk-in shower with tile walls. 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.

1620 Jaymes Cir, Middletown

Listing courtesy of Delaware Homes Inc. Contact: 3023789510
$680,000
5 Beds ⋅ 3 Baths
Step into a world of timeless elegance with this stunning Victorian home, a true masterpiece of craftsmanship and design. Built in 1900, this residence boasts and shows a life of owners who loved it and those who appreciated its unique architectural features. Beautiful hardwood floors throughout the entire home, including in the updated and modernized kitchen! Upgraded countertops and stainless steel appliances, including a dishwasher, 40" dual-fuel range and refrigerator. An extra refrigerator/freezer in the basement provide ample storage for all your culinary needs. The main floor laundry acts as a separator and tie between the rest of the house and the "in-law" suite which was once the summer kitchen. Retreat to one of the five generously sized bedrooms, each offering a peaceful haven for rest and relaxation. The home boasts 3 fireplaces, one fully flued for log burning, and though the other two are sealed off, the one in the kitchen has a wood-style, ventless propane stove installed. The bathrooms are thoughtfully designed, featuring walk-in showers, glass doors and electric, radiant-heat tile floors. One bathroom has even had accessibility in mind making it a "wet room" for those with mobility issues. Outside you will find no detail missed, as even the exterior shingles were hand scalloped to properly match the original victorian look and design. The front porch is inviting and relaxing to watch traffic drive by on their way through Middletown, and the sleeper porch allows you to have some peace and quiet while enjoying nature. With nearly a third acre lot, there's plenty of room for outdoor activities or gardening. This Victorian gem is not just a house; it's a place where memories are made, and stories are shared. Experience the perfect blend of classic elegance and contemporary comfort-your dream home awaits!

21 E Main St, Middletown

Listing courtesy of Maryland Real Estate Group. Contact: (301) 865-2037
$255,000
Totally rehabbed 2 unit with garage for extra rental space! One unit is rented for 1100 a month and 3 bedroom unit is vacant ready for a new tenant or a great place to move in yourself! Brand new kitchens, new bathrooms, all new vinyl plank floors and carpet, new appliances, freshly painted, updated electric and much more! Property is located in Middletown borough, land is leased.

129 Poplar St, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 7175342442
$64,900
3 Beds ⋅ 1 Baths
Welcome home to this beautifully renovated 3-bedroom, 1-bath mobile home located in Little Hollywood Mobile Home Court! Freshly updated and move-in ready, this home offers a bright and welcoming interior with comfortable living spaces and a functional layout. The renovations give the home a fresh, modern feel while offering an affordable opportunity to enjoy homeownership. With three bedrooms, there is plenty of flexibility for family, guests, a home office, or additional storage. Conveniently located in Middletown with easy access to shopping, dining, major roadways, and local amenities. All that’s left to do is move in and make it your own. Schedule your showing today!

109 Nancy Blvd, Middletown

Listing courtesy of NextHome Dream Seekers Realty). Contact: 7178025614
$300,000
3 Beds ⋅ 2 Baths
Welcome to this inviting bilevel home situated on a desirable corner lot with an amazing yard and fresh landscaping! Step inside the foyer and head upstairs to the main level, where the spacious living room features plush carpeting and a cozy gas fireplace. The formal dining room offers vinyl flooring and convenient outdoor access, while the eat-in kitchen provides plenty of cabinet space, a pantry for storage, vinyl flooring and a ceiling fan. Three generous bedrooms and a full bath complete the main level. Enjoy the changing seasons from the carpeted sunroom, a wonderful additional space to relax and take in views of the outdoors. The lower level offers even more living space with two additional bedrooms and a full bath, along with a spacious family room featuring exposed wood beams, chair railing, window treatments and a wet bar—perfect for entertaining or relaxing with family and friends. Outside, the deck overlooks the cleared backyard, providing a great setting for outdoor gatherings, play or simply enjoying your own private space. An oversized two-car garage offers plenty of room for vehicles, storage and more. Conveniently located near shopping, dining and entertainment, this well-loved home offers space, versatility and a location that is hard to beat. A joy to own!

1720 Oberlin Rd, Middletown

Listing courtesy of Joy Daniels Real Estate Group, Ltd. Contact: 7176953177
$598,000
3 Beds ⋅ 4 Baths
*MOVE IN READY* Welcome home to 3024 Ivyhouse Lane! Available for immediate move-in, this beautifully designed 3,223-square-foot Mendocino Luxe offers the perfect blend of space, comfort, and style. With 3 bedrooms, 4 bathrooms, a first-floor owner's suite, and a partially finished basement with a full bathroom, there's room for everything—from hosting family and friends to creating the perfect place to unwind. Located in the sought-after Venue at Winchelsea in Middletown, Delaware, the Mendocino Luxe floorplan is thoughtfully designed for comfort and luxury. Two versatile flex rooms welcome you off the foyer, leading into an open-concept living space that seamlessly connects the gourmet kitchen, dining area, and great room. Step into the sun room or outside to the covered rear porch—perfect for relaxing, entertaining, or enjoying the changing seasons. The partial finished basement with a full bathroom adds valuable living space, giving you the flexibility to create a home that fits your lifestyle. Tucked away at the back of the home, the luxurious owner's suite features a spa-inspired en-suite bathroom and two spacious walk-in closets. Upstairs, a generous loft provides the perfect setting for a media room, hobby space, home office, or cozy retreat. Don't miss your opportunity to call Venue at Winchelsea home! ** Please Read: Photos are for illustrative purposes only and may include renderings or images of the actual home or similar home/plan. Please see New Home Consultant for final pricing, finishes, and details. If you are working with a realtor, buyer representation must be acknowledged during the first interaction with Lennar, and the Realtor must accompany the client on their first visit. Appointments are highly encouraged to ensure the best customer experience. Taxes will be assessed after settlement. Open houses are held at the model home, not at this address. During your visit the sales team can review details, timelines, and current incentives. Financing is available through Lennar Mortgage upon qualification. ** For appointments and open houses, please visit the welcome home center located at 2405 Greyfriar Loop.*

3024 Ivyhouse Ln, Middletown

Listing courtesy of Atlantic Five Realty. Contact: 8564243339
$675,000
4 Beds ⋅ 4 Baths
Professional photos coming soon! WHERE HOME MEETS HOMETOWN! Beautifully built in 2019 and ideally located on a premium corner homesite, this exceptional Colonial offers the rare combination of a beautifully appointed, move-in-ready home and the welcoming lifestyle of Historic Middletown, one of Maryland's most desirable small towns. With three finished levels, four bedrooms, 3 full and 1 half baths, a covered front porch, a covered rear maintenance-free deck, and a location where schools, restaurants, the recently built library, community parks, and Historic Main Street are all within easy reach, this is a home designed to be lived in, enjoyed, and remembered. From the moment you arrive, the covered front porch invites you to slow down and enjoy the neighborhood and serene mountain views. Inside, the light-filled open floor plan creates an effortless flow for both everyday living and entertaining. Beautiful, engineered wood flooring throughout the main level, high ceilings, and an abundance of windows give the main level a bright, welcoming feel. The private office with French doors offers the perfect place to work from home, while the heart of the home is undoubtedly the spacious kitchen, breakfast/dining area, and family room. Gather around the oversized island in the gorgeous kitchen featuring timeless white cabinetry, quartz countertops, stainless steel appliances, gas range, wall oven, built-in microwave, dishwasher, refrigerator, and plenty of workspace for preparing everything from weekday meals to holiday dinners. The kitchen opens to the breakfast/dining area and family room, making it easy to stay connected with family and guests. A gas fireplace adds warmth and ambiance, while the extra windows bring the outdoors in. Just beyond the kitchen, the covered maintenance-free deck creates another inviting place to relax, dine al fresco, or gather with friends. A convenient rear hallway includes a pantry closet, powder room, coat closet, and access to the two-car garage. Upstairs, the spacious primary suite feels like a private retreat, complete with room for a sitting area, massive walk-in closet, and beautifully appointed ensuite bath with walk-in shower, dual-sink vanity, and private toilet room. Three additional bedrooms provide space for family, guests, hobbies, or a second home office. One bedroom features a large picture window that fills the room with natural light. The convenient upper-level laundry room with built-in shelving and full hall bath add to the thoughtful functionality of this level. The finished lower level adds an entirely new dimension to the home with a generous recreation room and walkout to a paver pad and the rear yard, along with a full bath, storage room, and utility room. Whether envisioned as a game room, movie night destination, guest space, exercise area, or simply a place to spread out, this flexible level adapts beautifully to your lifestyle. Freshly painted interiors, newly installed carpeting, a tankless water heater, natural gas heat, and an exceptionally well-designed floor plan make this home truly move-in ready. But perhaps what makes this property most special is the life you can live here. Step outside, and you're part of a community where neighbors gather, traditions matter, and there is always something to look forward to. Walk to Historic Main Street for restaurants and local events, enjoy Friday night football, stroll to the library, hear the church bells ring, or spend an afternoon at nearby Middletown Community Park with its trails, playgrounds, soccer and football fields, fishing pond, picnic areas, sand volleyball, disc golf, bandstand, and more. Middletown has a way of taking you back to a simpler time with holiday celebrations, parades down Main Street, outdoor movies, concerts in the park, and the familiar rhythm of a community that comes together. This is more than a beautiful house. It is a place to put down roots, make memories, and truly enjoy coming home.

12 Dean Ln, Middletown

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 746-2090
$874,900
3 Beds ⋅ 3 Baths
23+ ACRES *** 4,000+ TOTAL FINISHED SQ. FT. *** HORSE BARN *** TRAILS *** MIDDLETOWN VALLEY A rare opportunity to enjoy space, privacy and versatility in the heart of scenic Middletown Valley. Set on approximately 23.1 acres, this distinctive property brings together a spacious residence, expansive open acreage, equestrian improvements, a substantial barn and beautiful countryside surroundings—all while remaining convenient to Middletown and Frederick. The home offers more than 4,000 total finished square feet, with generous gathering spaces designed to take advantage of the property’s natural setting. One of the highlights is the impressive window-lined living/sunroom area, where abundant natural light and views of the surrounding acreage create a wonderful connection between the indoors and outdoors. A second expansive living area features a wood-burning stove, skylights and walls of windows overlooking the property. The main level offers a comfortable and functional layout with a primary bedroom suite featuring a private bath and walk-in closet, two additional bedrooms and another full bath. The spacious kitchen features granite countertops, stainless steel appliances, upgraded cabinetry and a large casual dining area, complemented by separate living and dining spaces. Hardwood flooring extends through much of the main level. The lower level significantly expands the home's usable space and offers excellent flexibility for recreation, guests, extended living arrangements, hobbies or a home office. Additional features include the laundry area and plumbing rough-in for another full bathroom. Outside is where this property becomes truly special. Step onto the large rear deck with a covered section and enjoy views across your own acreage. The property has been enhanced with trails throughout the land, creating opportunities for horseback riding, walking, recreation and simply enjoying the privacy of the setting. The deck and gazebo have also been repaired and refreshed. For the equestrian enthusiast, hobby farmer, collector or buyer simply looking for substantial additional space, the approximately 42' x 70' barn is an exceptional feature. The barn has its own electrical panel, an upper level and three horse stalls, providing substantial room for horses, equipment, storage, workshops or other permitted uses. Horse containment areas have also been improved. And despite the peaceful country setting, you don't have to give up convenience. Historic Main Street Middletown offers locally owned restaurants, shops and services, while the surrounding Middletown Valley is known for its mountain scenery, farmland and outdoor recreation. The Appalachian Trail, South Mountain area and Middletown's parks and walking trails add even more opportunities to enjoy the outdoors. For more extensive shopping, dining and entertainment, Downtown Frederick offers more than 200 specialty shops, galleries, breweries, distilleries and restaurants. The Middletown area is positioned along the historic US-40 Alternate/National Road corridor, providing connectivity toward Frederick and the surrounding region. 23+ acres. 4,000+ finished square feet. Horse facilities. An oversized barn. Trails. Privacy. Mountain-country surroundings. Properties offering this combination of acreage, living space and versatility in Middletown are difficult to duplicate.

2313 Bidle Rd, Middletown

Listing courtesy of Taylor Properties. 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 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 Unit #164, Middletown

Listing courtesy of Blenheim Marketing LLC. Contact: 3022540100
$249,900
3 Beds ⋅ 1 Baths
This renovated brick Cape Cod is completely move-in ready! Inside, you’ll find a more traditional layout with a separate living room and beautiful eat-in kitchen offering plenty of counter space. The main floor also features two spacious bedrooms and a full bathroom, perfect for anyone looking for one-level living. Upstairs, you’ll find a third bedroom with plenty of additional space. Out back, the fully fenced yard includes a swing set that stays, while the large detached garage offers plenty of room for parking, storage or a workshop. Conveniently located near shopping, restaurants and major highways, and offered at an affordable price, this home won’t last long! Schedule your showing today.

139 Columbia St, Middletown

Listing courtesy of Keller Williams Keystone Realty. Contact: 7177555599
$175,000
3 Beds ⋅ 2 Baths
Property is being sold AS IS. Spacious home in the beautiful town of Middletown with a 2-car garage, large lot, and plenty of square footage. This property offers an opportunity for the right buyer to renovate and make it their own. The home requires significant work and is priced accordingly. Bring your vision and contractor to transform this property into something special!

7976 Church St, Middletown

Listing courtesy of RE/MAX Roots. Contact: (540) 686-7362
$539,000
3 Beds ⋅ 3 Baths
Welcome to this well-maintained 3BR/3BA home in the desirable 55+ Spring Arbor community in Middletown. Offering approximately 3,110 square feet of living space, this home features one of the largest floor plans in the neighborhood and a thoughtfully designed layout that blends comfort, flexibility, and convenient first-floor living. Step inside to an inviting foyer with beautiful hardwood flooring that flows throughout much of the main level. The heart of the home is the spacious family room, highlighted by a soaring ceiling, abundant natural light, and a striking floor-to-ceiling stone fireplace. The open layout connects easily to the dining area and kitchen, creating a comfortable space for both everyday living and entertaining. The kitchen offers plenty of cabinetry and counter space, stainless steel appliances, recessed lighting, and a large center island. An adjoining breakfast nook provides a casual dining option, while the separate dining room is ready for larger gatherings. Additional main-level living spaces include a formal living room and a separate sitting room, offering plenty of flexibility for a home office, reading room, or quiet retreat. The spacious primary suite is conveniently located on the main level and features a large walk-in closet and a private bath with dual vanities, ceramic tile, a relaxing garden tub, and a separate tiled shower. A second bedroom and full hall bath are also located on the main level, providing an excellent setup for guests or anyone looking for the convenience of first-floor living. Just off the main living area, the bright sunroom provides a wonderful place to enjoy views of the backyard throughout the seasons. Step outside to the hardscaped patio and spacious yard, offering an inviting setting for morning coffee, outdoor dining, or simply relaxing and enjoying the outdoors. Upstairs, the home continues to offer impressive flexibility with a third bedroom, full bath, spacious loft, and a separate bonus room or office that connects to the primary suite. Whether used for guests, hobbies, a home office, or additional living space, there are plenty of options to make the second floor fit your needs. A large floored attic storage room provides an abundance of easily accessible storage and even more versatility. Outside, attractive stone and siding accents, mature landscaping, and a two-car garage add to the home's curb appeal. Spring Arbor's convenient location adjacent to Westown Town Center puts groceries, shopping, dining, and everyday conveniences just minutes from home, while still offering the comfortable residential setting of an established 55+ community. With 3 bedrooms, 3 full baths, multiple living areas, a main-level primary suite, generous storage, and flexible spaces throughout, this Spring Arbor home offers plenty of room to enjoy today with the versatility to meet your needs for years to come. MAKE THIS YOUR NEW HOME TODAY!

13 Palisade Cir, Middletown

Listing courtesy of EXP Realty, LLC. Contact: 8885434829
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