Middletown Real Estate

Middletown Real Estate

Welcome to the charming subdivision of Middletown, located in the heart of Middletown, US. This vibrant community offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place to call home.

Middletown is known for its picturesque streets lined with beautiful homes, lush greenery, and a strong sense of community. Residents here enjoy easy access to top-rated schools, shopping centers, dining options, and recreational facilities, making it a sought-after location for families and professionals alike.

With a variety of housing options to choose from, including single-family homes, townhouses, and condos, Middletown caters to a diverse range of preferences and lifestyles. Whether you're looking for a cozy starter home or a spacious property for your growing family, you'll find the perfect fit in this welcoming neighborhood.

Beyond its residential appeal, Middletown also boasts easy access to major highways and public transportation, making it a breeze to explore the surrounding areas and beyond. Whether you're commuting to work or seeking weekend adventures, Middletown's convenient location ensures that everything you need is within reach.

Experience the best of suburban living with a touch of urban flair in Middletown. Discover the warm community spirit, modern amenities, and endless possibilities that await you in this exceptional subdivision. Come and make Middletown your new home sweet home.

Newest Listings in Middletown

$425,000
3 Beds 2 Baths
Built in 1958 and tucked into the heart of historic Middletown, this distinctive all-brick rancher has a story all its own. Offering approximately 2,580 finished square feet—1,440 above grade and 1,140 finished below grade—on a .73-acre corner lot, the home was custom built by its original owners and reflects craftsmanship, character, and thoughtful design throughout. Tall ceilings and custom built-ins immediately set this home apart. The main level offers three spacious bedrooms, a full bath, and the comfort of radiant floor heating. The dining room features a built-in hutch and a clever pass-through connecting the kitchen and dining room with original rotating doors that close when not in use—a charming detail that speaks to the thoughtful design of the home. Main-level laundry is conveniently located in the kitchen. Just off the dining room, a screened porch creates a natural extension of the living space for dining and entertaining, while a rear covered porch offers another place to enjoy the outdoors. At the heart of the home is a dramatic masonry fireplace, centrally positioned and extending through both the main and lower levels. On the main level, it anchors a remarkable family room where a vaulted, beamed ceiling adds distinctive mid-century character with hints of Frank Lloyd Wright-inspired design. The fireplace continues into the lower-level family room, creating an architectural connection between the two living spaces. A tall, narrow vertical window beside the main-level entrance further complements the home’s design. One of the home’s most interesting features is the way its 1,440-square-foot main level and 1,140-square-foot finished lower level each have their own private exterior entrance. The lower level substantially expands the living space with a large second family room, full bath, and multiple finished flex rooms, several featuring high-set windows that bring in natural light. These versatile spaces offer options for guest accommodations, home offices, hobbies, or other uses. One was originally used as a photography darkroom for developing film—a unique detail that adds another layer to the home’s story. With its separate exterior entrance, full bath, and generous finished space, the lower level provides an opportunity to create a more private, independent living area depending on the next owner’s needs and applicable requirements. An extra-long attached one-car garage provides room for parking, storage, hobbies, or projects. A fold-away wall-mounted ironing board is another clever feature tucked into the home. Radiant heating within the main-level flooring provides warmth underfoot while also allowing heat to radiate into portions of the spaces below, including the garage beneath the dining room. Outside, the .73-acre corner lot offers off-street parking with access from more than one side, a large storage shed, and a private recreational court complete with a basketball hoop and markings for tennis and pickleball. Basketball and tennis have been enjoyed here through four generations, adding another chapter to the property’s history. All of this is within walking distance of schools, downtown Main Street, shops, restaurants, community amenities, and much of what makes historic Middletown special. This isn’t a cookie-cutter rancher. It was never intended to be. It’s a custom-built home with architectural personality, flexible living spaces, and details that tell a story. Perhaps the most meaningful part of that story is the land itself. The home was built on a portion of the original family farm—land that once extended across what is now home to Middletown Primary School, the Middletown Volunteer Fire Company, and Remsberg Park. Today, this property remains a tangible piece of that history. For the first time, it’s ready for its next chapter. **Full listing & photos will be available 9/24.  Showings to begin 9/25, not before.**

205 Franklin St, Middletown

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

$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

$375,000
3 Beds 2 Baths
OPEN HOUSE SATURDAY 8/29 11AM-1PM Welcome to this charming 3-bedroom home right across the street from Memorial Park in the heart of Middletown. offering classic character, flexible living space, and convenient off-street parking . Step inside to find beautiful hardwood floors and timeless woodwork that add warmth and character throughout the home. The main level features a comfortable living room that flows into your separate dining room and kitchen. Just beyond the kitchen, a spacious addition provides a versatile main-level third bedroom with access to its own private balcony. This flexible space could also make an excellent home office, guest room, den, or additional living area depending on your needs. Upstairs you'll find two additional bedrooms and a full bathroom. The primary bedroom connects to an additional walk-through room offering plenty of possibilities as a walk-in closet, dressing room, home office, nursery, or additional flex space. The unfinished basement provides additional storage and houses the home's mechanical systems, including newer heating and hot water equipment. Outside, enjoy a manageable backyard, detached shared garage, a reserved parking space, and a private driveway with room for approximately two additional vehicles. This home presents a great opportunity for its next owner to bring their own vision while preserving the hardwood floors, woodwork, and character that make the property unique. With three bedrooms, flexible bonus space, outdoor space, and hard-to-find off-street parking, this South Church Street home has plenty of potential to make your own. NOTE: This is an estate sale being sold strictly AS-IS where is by an out of state seller. Seller has never occupied the home, therefore are exempt from property disclosure/disclaimer, they do not have knowledge of the condition of the property, nor are they responsible to warrant or guarantee the condition.

319 S Church St, Middletown

Listing courtesy of Corner House Realty. Contact: (443) 499-3839

$375,000
3 Beds 3 Baths
A true life, “not many homes like this come along” scenario … just waiting for YOU! Step inside the charm of a 1930s PORCHFRONT semi-detached, RENOVATED, blending timeless character with modern conveniences. Featuring 3 nicely-sized bedrooms and 2.5 bathrooms, this inviting home offers all that you want and all that you’ll need! From an OPEN-CONCEPT FLOORPLAN, to beautiful LUXURY VINYL PLANK FLOORING THROUGHOUT and plenty of THOUGHTFUL UPDATES, you’ll be ready to call this home. Noticed immediately upon entry, the SPACIOUS FIRST FLOOR features a family room/dining room combo with an UPDATED KITCHEN that is bright, fresh and perfect for everyday living. Plus a CONVENIENT HALF BATH AND MAIN FLOOR LAUNDRY that add hard-to-find and highly desirable functionality. Beyond the kitchen, you’ll find the cutest COZY SUN PORCH that overlooks the FENCED-IN YARD. Upstairs, you’ll find more rarities that set this home apart, including the PRIMARY EN-SUITE and the FULLY FINISHED, FULLY FUNCTIONAL THIRD FLOOR ATTIC. The 3 UPDATED BATHROOMS complete the overall fresh and modern feel. Rounding out the MAJOR UPDATES are the 3 year YOUNG ROOF & HEAT PUMP plus the VINYL REPLACEMENT WINDOWS. Outside, you’ll enjoy an adorable, sizable storage shed plus OFF-STREET PARKING. To find all of this, in an ULTRA CONVENIENT in-town location close/walkable to shops & dining, you’ll just have to see for yourself. And as you do, WELCOME HOME!

307 S Cass St, Middletown

Listing courtesy of Crown Homes Real Estate. Contact: (302) 504-6147

$649,000
THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $649,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to assume a VA loan. Assumption is subject to buyer qualification and approval by the loan servicer/VA. Ask about the VA ASSUMABLE LOAN opportunity when scheduling your showing! Rare commercial opportunity in the heart of Middletown, ideally located directly across the street from the famous Wayside Theater and just minutes from I-81 with excellent accessibility and visibility. Zoned B-1 Commercial, this versatile property offers endless possibilities for business owners, investors, or developers seeking a unique space with flexible use options. Take advantage of the opportunity to live in or rent the attached apartment while running your business from the main portion of the home. See the attached document that outlines potential uses. The property features a beautifully maintained 1920s building full of character, including an inviting front porch, welcoming foyer, grand staircase, hardwood floors, exposed brick, and multiple decorative fireplaces that create a distinctive setting for a variety of commercial uses. The updated kitchen, numerous private rooms, and multiple bathrooms provide a functional layout well suited for professional offices, boutique retail, medical or wellness practices, hospitality, event space, or other approved commercial ventures. A significant advantage is the attached second unit, complete with its own kitchen, living area, two bedrooms, and two-and-a-half baths, offering exceptional flexibility for additional office space, employee accommodations where permitted, rental income, or complementary business operations. The configuration also allows the spaces to function independently or be integrated into one larger commercial operation. Situated on an expansive lot, the property includes a detached two-car garage with additional storage, a storage shed, abundant off-street parking, and ample outdoor space to accommodate a variety of business needs. Combining historic charm, modern updates, and valuable commercial zoning, this is a rare opportunity to establish or expand your business in a prime Middletown location with outstanding long-term investment potential.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$649,000
THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $649,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to assume a VA loan. Assumption is subject to buyer qualification and approval by the loan servicer/VA. Ask about the VA ASSUMABLE LOAN opportunity when scheduling your showing! Exceptional investment opportunity in the heart of Middletown, directly across from the famous Wayside Theater, and conveniently located just minutes from I-81. This unique property features two attached living units, offering outstanding income potential, multigenerational living, or the flexibility to occupy one unit while generating rental income from the other. The main residence showcases the timeless charm of a 1920s home with an inviting front porch, welcoming foyer, beautiful staircase, wood floors, exposed brick, and multiple decorative fireplaces. The updated kitchen features modern cabinetry and a center island. The main unit includes two main-level bedrooms with private en-suite baths, while the upper level offers a spacious primary suite with a walk-in closet and attached bath, plus two additional bedrooms that share a hall bath. The attached second unit is fully equipped with its own kitchen, living room, two bedrooms, and two-and-a-half baths, making it ideal for long-term tenants, short-term rental opportunities (subject to local regulations), or extended family. The property's layout also provides the option to combine both units into one expansive residence if desired. Situated on a generous lot, the property includes a detached two-car garage with additional storage, a storage shed, ample off-street parking, and plenty of outdoor space. Whether you're an investor seeking strong rental potential or a buyer looking for a property with flexible living and income opportunities, this one-of-a-kind multifamily property offers exceptional value in a prime location.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

$1,349,900
4 Beds 4 Baths
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

$649,000
7 Beds 7 Baths
THE FINANCING MAY BE AS IMPRESSIVE AS THE HOME! Offered at $649,000 with the potential opportunity for a qualified purchaser to assume the seller's existing VA loan. A VA assumption could offer a tremendous financing advantage compared with obtaining an entirely new mortgage, depending upon the existing loan terms and the buyer's financing structure. Veteran status is not necessarily required to assume a VA loan. Assumption is subject to buyer qualification and approval by the loan servicer/VA. Ask about the VA ASSUMABLE LOAN opportunity when scheduling your showing! Single family or multi-family with an approved, attached apartment - directly across from the famous Wayside Theater! This is a rare opportunity to own prime real estate in Middletown on a beautiful, large lot. Nestled in the heart of Middletown and just minutes from I-81, this exceptional 1920s home blends timeless character with modern updates. From the inviting front porch to the welcoming foyer with its stunning staircase, you'll immediately appreciate the home's classic charm. Beautiful wood floors, exposed brick, and multiple decorative fireplaces add warmth and character throughout. The updated kitchen features modern cabinetry, a center island, and ample space for gathering. Two main-level bedrooms each offer private en-suite baths, providing flexible living arrangements. Upstairs, the spacious primary suite includes a walk-in closet and attached bath, along with two additional bedrooms that share a hall bath. A unique highlight of this property is the attached second living unit located at the rear of the home. Complete with two bedrooms, two-and-a-half baths, a full kitchen, and living room, this space offers endless possibilities. It can serve as an in-law suite, guest quarters, or be seamlessly incorporated into the main residence to significantly expand the home's living space. The property also includes a detached two-car garage with additional storage, a storage shed, abundant parking, and plenty of outdoor space to enjoy. This one-of-a-kind property offers historic charm, flexible living options, and an unbeatable location.

7760 Main St, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099

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