Middletown Real Estate | Middletown 4 Bedroom Properties for Sale

A little bit of country feel, a lot of usable space, and a location that is increasingly hard to find. Tucked at the end of a cul-de-sac on more than half an acre, this charming 4-bedroom, 2.5-bath cape cod offers a private, tree-lined setting in the sought-after Middletown school district. Inside, the home has been thoughtfully refreshed while retaining the warmth and character that make this style of home so inviting. The updated kitchen features warm wood cabinetry, stainless steel appliances, a farmhouse-style sink, generous storage, and an easy connection to the adjoining living spaces. Fresh paint, carpet, and lighting add to the home’s comfortable, move-in-ready feel. The flexible floor plan includes a bedroom and full bath on the main level, which is ideal for guests, a home office, or those looking for the convenience of main-level living, along with three additional bedrooms and another full bath upstairs. Downstairs, the finished walkout lower level provides valuable additional living space with plenty of flexibility for a recreation room, media space, gym, playroom, or home office, while unfinished space offers additional storage. Outside is where this property really sets itself apart. The large deck overlooks a wooded backdrop and offers a peaceful place to entertain, dine outdoors, or simply enjoy the privacy of the setting. The spacious .52-acre lot provides plenty of room to spread out, while mature trees give the property an established, tucked-away feel. An oversized detached two-car garage with additional storage, along with a generous driveway, provides exceptional parking and versatility. With four bedrooms, multiple living spaces, a finished walkout lower level, detached garage, more than half an acre, and a cul-de-sac setting backing to woods, this is a rare opportunity to enjoy space and privacy without giving up the convenience of Middletown. This one-of-a-kind property is located within close distance to Middletown Park, downtown shopping and dining, grocery stores, and all of Middletown’s charm on Main Street.

7 Eastern Cir, Middletown

Listing courtesy of Compass. Contact: (240) 335-7355

$665,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status

Welcome to this former model home on a spacious corner lot offering comfort, flexibility and inviting indoor and outdoor living. The main level features refinished hardwood floors, a dedicated office, a bright kitchen with granite counters and large island, and a family room with a wood-burning fireplace framed by a dramatic floor-to-ceiling brick surround. Just off the kitchen, the skylit three-season sunroom offers a peaceful retreat with electric heat. Upstairs, four bedrooms include a spacious primary suite with walk-in closet and renovated bath featuring a tub and separate shower. The fully finished and renovated basement adds a large recreation room with propane stove plus a separate flex room for guests, an office, workout space or hobbies. Outside, enjoy a fenced yard, maintenance-free deck with built-in bar counter, adjoining patio and fire pit, plus a side-load two-car garage. All this just a short distance to Middletown Park, downtown shops, restaurants, grocery shopping and the many amenities of this charming Main Street community.

301 Cone Branch Dr, Middletown

Listing courtesy of Samson Properties. Contact: 2406308689

$410,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status

Welcome to 5 Bankbarn Circle, a stunning three-story townhouse offering 2,416 square feet of beautifully designed living space in Middletown’s highly desirable Glenbrook community. This home features four spacious bedrooms, three and a half baths, and three levels of expanded space thanks to generous rear bump-outs and a step-up entryway leading to a large living room with a classic bay window. Perfect for relaxing or entertaining, the home has scenic mountain views, a bright kitchen with a center island and breakfast area, and a rear deck.��Retire to the primary suite featuring a luxurious soaking tub and separate shower, or utilize the fully finished lower level. Most importantly, this turnkey home offers ultimate peace of mind with major systems recently replaced: a new HVAC system in 2021, a new water heater in 2024, a brand-new roof in 2025, and updated gutters and downspouts in 2025. Located within the top-rated Frederick County Public Schools district, this remarkable property is ready to welcome you home.

5 Bankbarn Cir, Middletown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,050,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status

Carefully reimagined between 2018 and 2021 with over $1.5M in updates, this historic Main Street home now lives like a luxury boutique retreat hidden in the heart of Middletown — complete with a secret speakeasy concealed behind a swinging bookshelf, a breathtaking custom kitchen addition, and a covered courtyard entertaining area anchored by a stunning stone fireplace. Rich in history yet thoughtfully transformed for modern luxury living, this extraordinary four-bedroom residence with dedicated office space blends timeless craftsmanship with sophisticated design rarely found in historic homes. Perched above historic Main Street with sunset views toward South Mountain, the home showcases soaring ceilings, original architectural details, custom Mennonite-crafted millwork, designer Circa lighting, and extensive infrastructure updates throughout. At the heart of the home is the stunning kitchen addition featuring exposed historic brick, dramatic steel scissor-beam trusses, handcrafted cabinetry, quartz perimeter counters, granite center island, GE Monogram appliances, farmhouse sink, induction cooktop, and a dramatic picture window overlooking the beautifully landscaped courtyard and covered side porch. The original kitchen was transformed into a spacious dining room, creating exceptional flow for entertaining while preserving the home’s historic character. Outdoor living spaces feel like an extension of the home itself with stamped concrete, custom stone fireplace, a covered entertaining area, and beautifully landscaped gathering spaces designed for both intimate evenings and large-scale entertaining. The front parlor was transformed into a stunning library with built-in shelving, restored historic shutters, statement lighting, and the hidden swinging bookshelf leading to the speakeasy featuring a solid wood bar, wet bar, beverage refrigerator, custom ceiling paneling, and dramatic finishes. The family room was created by opening two original parlors and is crowned by a dramatic bay window that floods the space with natural light. Upstairs, the home offers two primary suites along with spacious secondary bedrooms featuring exceptional flexibility, including a custom Murphy bed/work table system and built-in bay window seating. A dedicated office conceals a hidden opening into an untouched portion of the original home, creating a fascinating preserved time capsule rarely found in homes of this era. A covered upper porch overlooks the courtyard below, while the redesigned laundry room introduces statement lighting and additional storage. The finished attic was transformed into a truly unique owner’s retreat featuring reclaimed oak flooring, exposed brick chimneys, preserved historic wall surfaces, dressing room, laundry chute, separate staircase access, and a spa-inspired bath with a hidden Japanese-inspired Ofuro soaking tub room. Infrastructure improvements include dedicated high-end Carrier HVAC systems with hospital-grade filtration and smart thermostats, radiant heated floors, replaced electrical systems in 2020, updated copper plumbing, Japanese toilets, hand-tooled standing seam metal roof, replacement gutters, energy-efficient wooden sash windows, composite porch decking, central vacuum, Sonos integration, and extensive custom woodworking throughout. Stretching from Main Street to West Green Street, the property also has a subdivided, buildable rear lot. The purchaser of 19 E Main Street will have first right of refusal on the lot, which is also available separately, creating a rare opportunity for future expansion or investment in the heart of Middletown. Located on one of Maryland’s historic designated Main Streets, just steps from Middletown’s restaurants, library, shops, parks, & sought-after schools, this extraordinary residence offers a lifestyle as rare as the home itself. Sellers are sad to leave, as they finished it as their forever home.

19 E Main St, Middletown

Listing courtesy of RE/MAX Results. Contact: (301) 698-5005

$539,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status

Welcome to 4492 Jade Court, where a complete interior and exterior renovation meets an exceptional private backyard retreat. Situated on a generous .55-acre lot, this truly move-in-ready home offers 4 bedrooms, 2.5 bathrooms, approximately 2,200 square feet of finished living space, and an extensive list of major improvements. The exterior has been completely refreshed with a new architectural-shingle roof, brand-new vinyl siding, new gutters and shutters, and all-new double-hung, double-pane replacement windows. The fully fenced backyard is designed for both relaxation and entertaining, featuring an impressive 40-by-20-foot in-ground pool with a diving board and slide, a spacious concrete entertaining area, and a gazebo that conveys with the property. A matching storage shed provides additional convenience, while the brand-new two-level deck creates multiple outdoor living spaces overlooking the private backyard. Inside, beautifully refinished original hardwood floors add warmth and character throughout the main living areas. The completely renovated kitchen features quartz countertops, brand-new stainless-steel appliances, a true exterior-vented range hood, and a center island with overhang seating. A new sliding glass door provides direct access from the kitchen to the lower deck, making indoor-outdoor entertaining effortless. The entry level includes a primary bedroom with an en-suite full bathroom and its own private exterior access to the backyard. The main living area is highlighted by a natural wood-burning stove, creating a warm and inviting setting for colder evenings. Upstairs, you will find three additional bedrooms and a second full bathroom. One of the upper-level bedrooms offers direct access to the bathroom and could serve as an additional primary bedroom. A second new sliding glass door opens onto the upper deck, where you can enjoy elevated views of the pool and backyard. The fully finished lower level adds even more versatile living space with brand-new vinyl plank flooring, a convenient half bathroom, and walkout access to the exterior. Additional improvements include new recessed lighting throughout and a brand-new HVAC system. With the major systems, exterior, interior finishes, kitchen, bathrooms, windows, decks, and outdoor entertaining areas already completed, this home is the definition of move-in ready. Simply unpack, settle in, and enjoy your beautifully renovated home and private backyard oasis.

4492 Jade Ct, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: (717) 757-2717

$799,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status

Welcome to 411 Glenbrook Drive in the desirable Glenbrook community of Middletown. This home offers over 4,600 finished square feet of living space with a great layout, beautiful golf course views, and several recent updates. The main level features a two-story foyer, formal living and dining rooms, and a spacious kitchen with upgraded cabinetry, a large center island, and a bright morning room overlooking the surrounding landscape. The open living area features soaring ceilings, abundant natural light, and a welcoming space that is ideal for relaxing or entertaining. The main level primary suite offers convenience with an ensuite bathroom and generous closet space. The upper level includes additional bedrooms and flexible living areas to fit a variety of needs. The finished walk-out lower level provides additional space for recreation, a home office, or additional living areas. Outside, enjoy the patio and peaceful golf course setting that Glenbrook has to offer. Recent improvements include a brand new roof, new gutters, and an owned photovoltaic solar system that conveys with the property, providing energy efficiency and added value for the next homeowner. Conveniently located in Middletown with easy access to shopping, dining, commuter routes, and Frederick County schools. This wonderful home offers a combination of space, updates, and a desirable location - don't miss your opportunity to call this house, home!

411 Glenbrook Dr, Middletown

Listing courtesy of Real Estate Teams, LLC. Contact: 3016953020

$1,349,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 3.78 beautiful acres, 7452 Heritage Oak Terr (Lot 4W) is a gorgeous build-ready homesite with perc approval and well installed. Advertised is the ACL4 plan which features over 4,400 finished sqft, 4 bedrooms and 3.5 baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, formal dining room, morning room, private office, a stately Owner's suite w/260 sqft walk-in closet, Hardie Plank siding and full stone water table are just a few standard options in this model. Advertised is the base price for the ACL4 model on this lot. Photos are of a previously built ACL4 model a modern farmhouse elevation. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

7453 Heritage Oak Ter, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

$1,249,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 4.65 beautiful acres, 3130 Bidle Rd (Lot 1E) is a gorgeous build-ready homesite that offers a perfect combination of protected woodlands and rolling pastoral landscape. Advertised is the ACL3 plan which features over 3,000 finished sqft, 4 bedrooms, 3.5 baths including a main level owner's suite. Additional standard features include a spacious open concept kitchen with large center island and high end cabinetry, beautiful 2 story foyer, morning room, private office, luxurious Owner's suite, Hardie Plank siding and full stone water table. Photos are of a home that builder recently finished in Frederick County. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

3130 Bidle Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

$499,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Welcome to this beautiful colonial in the heart of Middletown, MD, where small-town charm, community character, and a prime Main Street address come together on a generous half acre lot! There is SO MUCH potential to revitalize this home to your most creative imagination. Bathed in natural light throughout, this spacious 4-bedroom, 2-bath home features gleaming hardwood floors and a comfortable, flowing layout. The main level offers a primary bedroom with a private ensuite bath, ideal for single-level living convenience, while the upper-level hosts three additional generously sized bedrooms and a full bath. The expansive lot provides plenty of outdoor space to enjoy, entertain, and make your own. A roof updated in 2025 offers genuine peace of mind, and the home is connected to the public sewer system via a Sanitary Sewer Lift Pump, offering the reliability of public utilities. Middletown offers everything you come here for, a small-town feel with walkability to parks, restaurants, the library, and shopping, including beloved local spots like The Main Cup, Fratelli's Italian & Seafood, and Aleko's Village Cafe just down the road. The 79-acre Middletown Community Park is just minutes away, offering basketball courts, soccer fields, disc golf, fishing, picnic shelters, and walking trails. Commuters will appreciate the easy access to I-70 and Rt. 340, with Downtown Frederick just a short drive away. Don't miss this one!

718 E Main St, Middletown

Listing courtesy of Keller Williams Realty Centre. Contact:

$475,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status

Welcome to this charming 4-bedroom, 2-bathroom home ideally situated on Main Street in the heart of Middletown, offering the perfect blend of character, comfort, and convenience. Step inside to beautiful hardwood floors that flow throughout the main level, creating a warm and inviting atmosphere. The formal living room features a cozy wood-burning fireplace, making it the perfect place to gather on chilly winter evenings. Just beyond, the formal dining room provides an elegant setting for holiday celebrations, dinner parties, and everyday meals. The updated kitchen is designed with both style and functionality in mind, featuring a spacious island perfect for entertaining, ample cabinet storage, and a bright breakfast area where you can enjoy your morning coffee while overlooking the expansive backyard. The main level offers two comfortable bedrooms and a full bathroom, providing flexible living options for guests, family, or a home office. The finished lower level includes two additional generously sized bedrooms, a second full bathroom, and a spacious laundry room with abundant storage. Outdoor living is just as inviting, with a large deck that's perfect for summer barbecues, outdoor dining, and relaxing evenings. The one-car garage offers additional storage, while the oversized backyard provides endless possibilities with plenty of room for play, gardening, pets, or future outdoor entertaining spaces. Located just moments from Middletown's charming shops, restaurants, parks, and top-rated schools, this home offers small-town living with all the conveniences you need. Don't miss your opportunity to make this beautiful Main Street home your own.

708 E Main St, Middletown

Listing courtesy of Keller Williams Realty Centre. Contact:

$499,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status

*One or more photos in this listing have been virtually staged using AI* Completely Renovated & Move-In Ready! Welcome to this beautifully updated ranch-style home situated on a picturesque 2-acre lot in the heart of Middletown Valley. Every detail has been thoughtfully renovated, offering a bright, modern interior with quality finishes throughout. The open and inviting floor plan is perfect for everyday living and entertaining. Step outside to enjoy the spacious backyard, offering endless possibilities for outdoor gatherings, recreation, gardening, or simply relaxing while taking in the peaceful surroundings. Enjoy the tranquility of country living while remaining just minutes from downtown Middletown, Frederick, shopping, dining, schools, parks, and major commuter routes. Whether you're looking for your forever home or a quiet retreat with modern comforts, this exceptional property is ready for its new owner. Don't miss this rare opportunity!

9001 Hollow Rd, Middletown

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact:

$839,999

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status

Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown Glen community. Ideally located within walking distance of schools, parks, and the library, this home also enjoys a beautiful view of the neighborhood’s open common area directly across the street, creating a spacious and inviting setting . Also this exceptional home is also just minutes from the nature center, local restaurants, golf courses, and major commuter routes. Step inside to a welcoming foyer featuring a private home office, then continue past the elegant formal dining room into the spacious living room that seamlessly opens to the bright, eat-in kitchen—perfect for everyday living and entertaining. Entering through the attached 2-car garage, you'll appreciate the thoughtfully designed mudroom with built-in storage, along with an oversized pantry and convenient powder room on the main level. Upstairs offers an ideal layout with an additional loft-style lounge that provides flexible living space. The luxurious primary suite occupies its own private wing and features a sitting area, two walk-in closets, and a spa-like ensuite bath. Two additional bedrooms share a full hall bath, while the opposite wing includes a fourth bedroom with its own ensuite bath and a conveniently located laundry room. The finished walkout basement is an entertainer's dream, featuring a large recreation area, wet bar, full bathroom, and ample storage space. Outside, the beautifully hardscaped backyard offers a low-maintenance setting that's perfect for relaxing or hosting gatherings. Meticulously maintained and truly move-in ready, this thoughtfully upgraded home combines generous living spaces, quality finishes, and an unbeatable location. 5 Dean Lane has everything you've been looking for.

5 Dean Ln, Middletown

Listing courtesy of Real Estate Innovations. Contact:

$2,500,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status

Experience the flow of space and harmony a private 5-acre sanctuary where mid-century soul meets meticulous architectural restoration. Set among park-like grounds and hundreds of flowering trees, this retreat-like residence is wrapped by protected conservation land on two sides, delivering incomparable privacy and a serene stage for entertaining, work, and retreat. From the views of Middletown Valley and South Mountain to 1960s design roots, to modern comfort, the home embodies seclusion without sacrificing accessibility. At the heart of the living spaces, a grand fireplace anchors the flow, guiding the eye and gathering rooms into a seamless continuum. The layout invites conversations to drift from indoor to outdoor and back again, with spaces merging around this warm, sculptural anchor. From Kentucky pink sandstone and cedar exteriors to warm interior touches—wood floors, custom concrete sinks, maple doors and trim, and a well-organized mudroom and laundry area—every surface speaks to craft and longevity. On the main level the Center Room is designed for living and entertaining. It is enriched by commissioned art, beautiful Kentucky sandstone fireplace and huge windows that look out over the Middletown Valley. A wrap around deck allows transition from the indoors to out, with just a few footsteps. A dedicated library with custom maple shelving creates a quiet, sunlit mezzanine of ideas—is a perfect retreat for reading, group study, or inspiration. The stunning kitchen was designed in collaboration with local architect, Clyde Burger. The two 12’ long walnut islands and all the kitchen cabinetry is hand-built Mennonite woodwork. The work surfaces are polished concrete, and the built-in appliances are professional grade. A kitchen lounge houses built-in cabinetry and encourages family and social time as meals are prepared and enjoyed. An 18-foot NanaWall opens to dissolve the boundary between inside and outdoor. The main level laundry has clean lines, beautiful carpentry, wonderful hand built floating shelves, custom concrete surfaces and sink as well as a wet floor and direct access to the decks and yard. The mudroom and powder room also feature custom cabinetry and specially designed features, such as the concrete sink and the floating concrete benches. The primary suite is un-filled, architectural artistry with an imported floor, two walk-in closets (one cedar-lined), and a bath featuring terrazzo floors and a standout view. Two en-suite bedrooms, renovated December 2025, have wood floors with custom Navajo-inspired wood inlays. Commissioned furnishings fill of the rooms and both enjoy nature views. The lower-level spaces are also remarkable. The second grand room has a vibrant MCM fireplace and is ideal for family activities, mediation or intimate gatherings. The windows showcase the valley view, and the doors open directly to the saltwater pool. Two private rooms are ready to use as bedrooms or office spaces. The full bathroom also has a custom concrete vanity and floor and warm cork tiling. This wing of the lower-level embraces angles and has built floating shelves in the lower library. Additionally, this level offers a bright, versatile studio providing space for creativity of all types—art, writing, design, or restorative projects— to inspire and nurture imagination. The exterior grounds are a living landscape. The 5-acre parcel unfolds as a natural paradise with park-like landscaping and hundreds of flowering trees seen from every window. The long drive lined with light poles and the parking area edged by planters sets a welcoming tone as you approach the home. A multi-level Brazilian hardwood deck overlooks a heated saltwater pool; a detached barn houses a traditional Scandinavian sauna and a lounge for year-round wellness. The homes systems are wellness-oriented including geothermal HVAC, a brand-new roof with a 50-year warranty, a multi-stage water softening system.

9237 Frostown Rd, Middletown

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$1,185,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status

HOME TO BE BUILT - Don't miss the final opportunity to build your custom home! Experience the breathtaking mountain views and modern luxury in this stunning new construction home to be built by Grossnickle Construction, nestled in the heart of Middletown Valley. This thoughtfully designed 4-bedroom, 3.5 bath home offers the perfect blend of elegance, comfort and functionality. Step inside to discover an open concept floor plan featuring spacious living areas, abundant natural light and high-end finishes throughout. The gourmet kitchen will impress with premium cabinetry, quartz countertops, oversized island and seamless flow into the dining and family rooms - perfect for entertaining or everyday living. Conveniently located near charming downtown Middletown, parks and commuter route, this exceptional to be built home offers the rare opportunity to personalize your dream home.

5901 Cloudberry Ct, Middletown

Listing courtesy of Charis Realty Group. Contact: 3018315099

Middletown 4 Bedroom Properties for Sale

Newest Middletown 4 Bedroom Properties for Sale