Middletown Real Estate

Middletown Real Estate

Welcome to Middletown, a charming subdivision nestled in the heart of the United States, where community spirit and suburban tranquility come together in perfect harmony. Known for its picturesque landscapes and friendly atmosphere, Middletown is the ideal place for families, professionals, and retirees alike to call home.

As you stroll through the tree-lined streets of Middletown, you’ll discover a variety of beautiful homes, each with its own unique character. From cozy single-family residences to spacious townhouses, the real estate options here cater to diverse lifestyles and budgets. The well-maintained yards and inviting front porches create a warm sense of community, making it easy to meet your neighbors and forge lasting friendships.

Middletown boasts an array of amenities that enhance the quality of life for its residents. Enjoy leisurely afternoons at the local parks, complete with playgrounds, walking trails, and picnic areas perfect for family gatherings. For those who appreciate the arts, the nearby cultural centers and galleries provide a vibrant backdrop for community events and exhibitions.

Education is a cornerstone of Middletown, with highly-rated schools that prioritize student success and community involvement. Families can rest easy knowing their children have access to quality education and extracurricular activities.

Conveniently located near major highways, Middletown offers easy access to nearby cities, shopping centers, and dining options. Whether you’re looking for a quiet retreat or a lively suburban lifestyle, Middletown has it all. Come and discover the charm and warmth of this delightful subdivision—your dream home awaits!

Newest Listings in Middletown

$425,000
3 Beds 2 Baths MDFR2089292 MLS
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

$658,139
3 Beds 2 Baths DENC2111176 MLS
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

$375,000
3 Beds 2 Baths MDFR2088998 MLS
Nestled in the charming community of Middletown, this delightful bungalow offers a perfect blend of comfort and convenience. Built in 1945, this home exudes character with its classic architectural style and inviting ambiance. With 3 bedrooms and 2 full bathrooms, this residence is designed for both relaxation and functionality. As you step inside, the warmth of hardwood flooring welcomes you, leading you to a cozy living area complete with a gas fireplace-perfect for those chilly evenings spent with loved ones. This home offers a newer HVAC(2022) system and updated windows(2022) on the main level. Enjoy the kitchen with stainless appliances and granite countertops. The partially finished basement provides additional space for a home office, playroom, or storage, while the side entrance adds convenience for everyday living. The exterior features low-maintenance vinyl siding and a brand new roof(2026), ensuring you can spend more time enjoying the community and less time on upkeep. The generous lot size of 0.21 acres offers ample outdoor space for gardening, play, or simply unwinding in the fresh air. Middletown is not just a place to live; it's a vibrant community that fosters connection and engagement. Residents enjoy easy access to local parks, where you can take leisurely strolls, have picnics, or let the kids play freely. The neighborhood is known for its friendly atmosphere, making it easy to meet neighbors and build lasting friendships. The community is well-served by public services, providing peace of mind and convenience for all residents. The location also offers easy access to local amenities, including shops, restaurants, and recreational facilities, making everyday errands simple and enjoyable. This home in Middletown is more than just a property; it's a place where memories are made, and community bonds are strengthened. Experience the warmth and charm of this inviting bungalow, and discover the lifestyle that awaits you in this wonderful neighborhood. Don't miss the opportunity to make this house your home!

400 W Green St, Middletown

$650,000
3 Beds 3 Baths MDFR2088606 MLS
Step into timeless charm without leaving behind today's comforts. This distinctive Painted Lady captures the character, craftsmanship, and gracious proportions that make a home truly memorable, right in the heart of Middletown. Set well back from historic Main Street behind an expansive front lawn, the home has an impressive presence, with a wide wraparound porch inviting you to sit awhile and enjoy the rhythm of small-town living. Located within the sought-after Middletown school district, this is a home that feels a part of the town’s story. Offering over 3,000 finished square feet above grade, the home has been lovingly cared for by the same owners since 1997. Natural light and tall ceilings on every level create a remarkably open and airy feel, while fresh paint complements the beautiful architectural details throughout. An impressive entry foyer sets the tone with original millwork and wood floors, fireplace mantels, pocket doors, a built-in bookcase, and a distinctive split staircase. Stacked bay windows on separate levels feature diamond-pattern divided-light upper sashes and clear glass below—one of the many details that makes this home so special. The spacious front living room features custom built-ins, a fireplace, and pocket doors connecting both the foyer and dining room. The large dining room is ready for holidays, celebrations, and everyday dinners, with a side door opening directly onto the wraparound porch. The updated kitchen blends classic character with modern function, featuring a large center island, wall oven, cooktop, built-in cabinetry, and a charming original pass-through cupboard. A mudroom provides a practical everyday entrance and access to the covered rear porch, while a main-level half bath adds convenience. Upstairs are three generously sized bedrooms, including a spacious primary suite with a private full bath, plus an additional hall bath. An open loft area provides flexible space for an office, study, reading nook, or sitting area. The completely remodeled finished third floor adds another exceptional level of living space, with tall ceilings, abundant natural light, a large recreation room, separate den, and laundry area. Use it as an office, studio, exercise space, media room, hobby room, or private retreat. A unique glass-floor feature allows light to pass through and adds an unexpected architectural element. Outside, there is room to breathe—something increasingly difficult to find right in the heart of town. The large, level property stretches from Main Street to Green Street with access from both streets, offering an expansive front lawn and spacious backyard. A detached one-car garage adds convenience, while eligibility for future subdivision through the Town of Middletown adds another unique dimension. Additional features include air conditioning, radiator heat, updated electrical, a clean unfinished basement for utility and storage, and eligibility for a one-year home warranty. Perhaps what makes this home most memorable is simply the feeling of it—the sunlight, tall ceilings, warmth of the wood floors, beautiful architectural details, and the ability to step onto that wonderful wraparound porch and watch Main Street go by. Filled with charm and personality, yet offering the light, space, and functionality for the way we live today, this gracious Painted Lady is ready for its next chapter.

305 E Main St, Middletown

$375,000
3 Beds 2 Baths MDFR2087904 MLS
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

$375,000
3 Beds 3 Baths DENC2109160 MLS
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

$649,000
VAFV2043814 MLS
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

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