Middletown Real Estate

Welcome to Middletown, New York – a charming city nestled in the heart of Orange County. With its rich history, vibrant community, and stunning natural surroundings, Middletown offers a unique blend of small-town charm and modern conveniences.

Founded in the late 18th century, Middletown boasts a rich historical tapestry that can be seen in its well-preserved architecture and landmarks. The city is known for its friendly atmosphere and welcoming residents, making it an ideal place for families, young professionals, and retirees alike. With a diverse population, you’ll find a variety of cultural events and community activities that foster a strong sense of belonging.

Nature enthusiasts will delight in the scenic beauty surrounding Middletown. The city is conveniently located near the breathtaking landscapes of the Hudson Valley, offering ample opportunities for hiking, biking, and exploring the great outdoors. Local parks, such as the popular Fancher-Davidge Park, provide perfect spots for picnics, recreational activities, and family gatherings.

Middletown also boasts a thriving local economy, with a mix of retail shops, restaurants, and business services that cater to residents and visitors alike. The city’s strategic location along major transportation routes ensures easy access to nearby cities while maintaining its peaceful, suburban feel.

Whether you’re looking to buy your first home, invest in property, or simply explore a new area, Middletown, NY, is a hidden gem waiting to be discovered. With its perfect blend of community spirit, natural beauty, and convenient amenities, it’s no wonder that so many are choosing to call this delightful city home. Come experience the charm of Middletown for yourself!

Newest Listings in Middletown

$325,000

3 Beds ⋅ 2 Baths ⋅ 1052724 MLS

This 3-bedroom, 1.5-bath raised ranch in Middletown offers 1,092 square feet of living space on a 0.22-acre lot, with a practical layout, hardwood floors, an attached two-car garage, just needs a little cosmetic refreshing to make it shine. The main level features a spacious living and dining area with hardwood flooring and a large picture window, creating an open, comfortable setting for everyday living and entertaining. The kitchen includes extensive warm wood cabinetry, light-colored countertops, a tiled backsplash, a gas range, built-in microwave, dishwasher, refrigerator, and a ceiling fan, with a convenient layout that connects naturally to the dining area. The home offers three bedrooms and a full bathroom with a tub/shower combination and wood cabinetry for storage. The lower level offers excellent potential for additional living space and an attached two-car garage. Outside, the property offers a beautiful back yard with a broad lawn, established landscaping, a paved rear patio, and attractive hardscaping with retaining walls that help define the sloped lot. Located in Middletown within the Middletown School District, the property is convenient to local shopping, dining, recreation, and transportation. The nearby Metro-North station provides service to NYC on the Port Jervis Line, while the Galleria at Crystal Run offers more than 100 shopping, dining, and entertainment options. The city also maintains numerous parks and recreational facilities. Major road connections including NY-17/I-86, NY-211, and I-84 provide access throughout Orange County and the surrounding Hudson Valley.

55 Orange Terrace, Middletown

$1,499,900

4 Beds ⋅ 4 Baths ⋅ DENC2111682 MLS

Nestled in the prestigious Highlands at Back Creek, this exquisite residence embodies the perfect blend of luxury and comfort. Built in 2022, this stunning detached home showcases a captivating Colonial and A-Frame architectural style, offering a timeless elegance that welcomes you from the moment you arrive. As you step inside, you are greeted by an expansive layout that seamlessly integrates modern design with warm, inviting spaces. The heart of the home features a spacious living area bathed in natural light, perfect for both intimate gatherings and grand entertaining. The gourmet kitchen is a chef's dream, equipped with top-of-the-line appliances and ample counter space, making meal preparation a delight. With four generously sized bedrooms and three and a half beautifully appointed bathrooms, this home provides an abundance of space for relaxation and rejuvenation. The master suite is a true sanctuary, complete with luxurious finishes and a spa-like en-suite bathroom that invites you to unwind after a long day. The full, unfinished basement offers endless possibilities for customization, whether you envision a home theater, gym, or additional living space. Step outside to discover your own personal oasis-a private pool surrounded by lush landscaping, perfect for summer days spent lounging in the sun or hosting unforgettable poolside gatherings. The property sits on a sprawling 0.81-acre lot, providing ample outdoor space for recreation and relaxation. The side-entry attached garage accommodates three vehicles, ensuring convenience and ease for you and your guests. This home is not just a residence; it's a lifestyle. Enjoy the tranquility of suburban living while being just moments away from vibrant local amenities. The Highlands at Back Creek community offers a serene environment, perfect for those seeking a peaceful retreat without sacrificing accessibility to shopping, dining, and entertainment. Experience the epitome of luxury living in this remarkable home, where every detail has been thoughtfully curated to create a warm and inviting atmosphere. Don't miss the opportunity to make this dream home your reality. Schedule your private tour today and step into a world of elegance and comfort.

134 Ayshire Dr, Middletown

$79,900

PADA2063830 MLS

Rare Opportunity in Middletown Borough! This spacious .58-acre corner lot offers road frontage and sidewalks on two sides, located within the borough of Middletown. Public utilities available include water, sewer, electric, and natural gas. Currently zoned Residential R2, the property was previously zoned commercial and lot adjacent to property is zoned commercial C-2 —making a zoning change to Commercial C2 a viable option. Property has been granted a variance to permit storage unts to be built on property. The location, near Route 441 and the railroad, makes it ideal for a storage garage, contractor yard, or equipment parking, pending appropriate zoning approval. A rare find with exceptional potential for both residential or light commercial use!

Wilson St, Middletown

$420,000

3 Beds ⋅ 2 Baths ⋅ 1052153 MLS

Welcome home to this beautifully updated 3-bedroom, 1.5-bathroom house located in a quiet neighborhood! This home features new flooring and fresh paint throughout, an updated kitchen, and a large deck with an expansive yard—perfect for relaxing or entertaining. The property includes private driveway parking and a full basement providing ample storage. With the added convenience of an in-unit washer and dryer, this home is move-in ready and designed for easy living.

4 Westminster Drive, Middletown

$289,900

3 Beds ⋅ 2 Baths ⋅ PADA2064318 MLS

Country living with convenience. Located between Elizabethtown and Middletown in Londonderry Township within Lower Dauphin School District. One level living brick ranch home with spacious covered front porch and a pleasant view of pristine farmland. Property consists of two parcels that total 1.07 acres with road frontage an front and rear of lot which would accommodate a pole building at rear of lot if needed. 1350 square feet of finished living area above grade, open living and dining room with large windows and pristine hardwood floors. Three bedrooms which include a primary bedroom with half bath, and a main bath with tub/shower. Full unfinished basement, professionally waterproofed with wood stove, laundry area (laundry temporarily located in 2nd bedroom) and both interior and exterior access. Architectural shingled roof, two hundred Amp Electrical distribution box, central air conditioning, and attic access. Attached oversize 20 x 29 garage with two new windows and a detached two-car garage that sits behind home and is accessible by paved driveway. Peaceful setting, just minutes from Elizabethtown and Middletown and will provide you with a place to decompress. Let us help you make this your home, call now!

275 N Deodate Rd, Middletown

$375,000

6 Beds ⋅ 3 Baths ⋅ PADA2064272 MLS

2 homes on 1 lot!!! Exceptional flexibility on a spacious Lower Swatara Township property: a main residence, finished lower-level living space, and a separate second home on the same lot. The main residence offers a large living room, kitchen and dining area, five bedrooms, 2½ baths, and a three-season porch. The primary bedroom is set apart from the others and includes a walk-in closet, with a layout that flexes for offices, hobby spaces, or guests. Not to mention new carpet throughout! The lower level adds a finished living area, kitchen, full bath, additional room, storage, utility space, and its own exterior access — ideal for extended family or added privacy. A 20x35 pole barn with concrete floor, electric, and water hookup availability provides covered space for campers, vehicles, and projects. The separate second home includes two bedrooms and one bath and is currently tenant-occupied.. Outdoor spaces include a covered front porch, a 40' deck, a 10x10 deck connecting the handicap ramp to the three-season porch, and a back porch on the second home. Lower Swatara Township, Middletown Area School District.

834 Oberlin Rd, Middletown

$349,900

3 Beds ⋅ 3 Baths ⋅ DENC2111460 MLS

Welcome to 501 Aidone Drive! This well-maintained end-unit townhome is located in the popular Middletown Village community and is truly move-in ready. The main level offers a bright and open layout with plenty of natural light and a gas fireplace that makes the living space feel warm and inviting. The kitchen offers plenty of cabinet and counter space with an adjoining dining area, making it easy to entertain or enjoy everyday meals. Upstairs you’ll find three nicely sized bedrooms, including a spacious primary bedroom with its own private bath and ample closet space. Two additional bedrooms and a full hall bath complete the upper level. Need more room? The finished lower level gives you plenty of options. Use it as a family room, home office, gym, playroom, or additional entertainment space. Step outside and enjoy the rear deck and fenced backyard that backs to open space, giving you a little extra privacy. The home has been well cared for and also features a new HVAC system. Conveniently located in the Appoquinimink School District with easy access to shopping, restaurants, major roadways, and everything Middletown has to offer. There’s nothing left to do but unpack and make it yours. Schedule your tour of 501 Aidone Drive today!

501 Aidone Dr, Middletown

$655,000

4 Beds ⋅ 3 Baths ⋅ DENC2111478 MLS

Welcome to 202 W Thomas Ct, a spacious 4-bedroom, 2.5-bath Colonial offering approximately 2,700 sq. ft. of above-grade living space on a beautiful half-acre lot in the peaceful Thomas Landing II community. Enjoy a private setting while remaining just minutes from shopping, dining, everyday conveniences, and major roadways. Step inside to a dramatic two-story foyer with a turned staircase, flanked by formal living and dining rooms. A beautifully updated first-floor office provides a stylish, dedicated space for working from home, studying, or managing everyday tasks. The inviting family room features a fireplace with marble surround and flows into the eat-in kitchen, complete with upgraded cabinetry, granite countertops, and a center island offering additional workspace and storage. A main-level bedroom, powder room, and laundry room complete the first floor. Upstairs, the spacious primary suite offers a sitting area, walk-in closet, and private full bath. Two additional bedrooms share a full hall bath. The full basement provides approximately 1,574 sq. ft. of additional below-grade space, including finished areas ideal for recreation, entertaining, fitness, or hobbies, along with abundant storage. Outdoor living truly sets this home apart. The expansive fenced backyard offers plenty of room to relax and entertain, complemented by a mature willow tree, screened gazebo perfect for morning coffee, and a rear deck for enjoying peaceful afternoons and evenings. Additional highlights include central air, an attached two-car garage, a radon mitigation system, and approximately two years remaining on the home's warranty. Located within the Appoquinimink School District, this Thomas Landing II home delivers an exceptional combination of space, flexibility, and indoor-outdoor living. Come experience 202 W Thomas Ct and make it your new home! (Professional photos coming soon)

202 W Thomas Ct, Middletown

$549,999

5 Beds ⋅ 4 Baths ⋅ 1049513 MLS

Welcome to 11 Amy Lane, where generous living space meets a surprisingly private setting in the heart of the Middletown area. Set on over half an acre with a wooded backdrop, this spacious 5-bedroom, 4-bath bi-level offers plenty of room to spread out, both inside and out. The upper level opens into a bright, open-concept living, dining, and kitchen area. The kitchen features stone countertops, an undermount sink, double wall ovens, and a large island with a built-in cooktop. Double French doors off the dining area lead directly onto the back deck, extending the living space outdoors. Down the hall, you'll find a full bath and additional bedroom. At the end of the hall is the large primary suite, complete with a private bath featuring a whirlpool tub, dual vanity, and separate water closet. Downstairs, the full walkout lower level nearly doubles the possibilities. Three additional bedrooms, two full baths, one with a convenient accessible walk-in tub, a second kitchen, laundry room, and additional living spaces create an incredibly versatile layout with room for guests, work, hobbies, or simply more space to call your own. One of the bedrooms also has its own exterior foyer and entrance, opening up even more possibilities for how the space could be used. Outside is where this property really sets itself apart. The spacious upper deck overlooks the wooded surroundings, while a lower stone patio, beautiful hardscaping, koi pond, and plenty of yard create multiple spaces to enjoy the outdoors. The fully fenced side yard adds another defined outdoor space, while the wide driveway and attached two-car garage provide plenty of room for parking and storage. And yet, you're just minutes from Route 211, shopping, dining, and major commuter routes, giving you the convenience of Middletown with a setting that feels pleasantly removed from it all.

11 Amy Lane, Middletown

$1,550,000

5 Beds ⋅ 4 Baths ⋅ DENC2111350 MLS

A truly extraordinary opportunity to own a restored piece of Delaware history, 220 Nighthawk Drive—historically known as the Mrs. Templeman Farmhouse—is a remarkable circa-1830 residence where nearly two centuries of character have been preserved and paired with modern luxury. Set on 5.81 acres, this approximately 5,500 sq. ft., 5-bed, 3.5-bath home underwent an extensive renovation completed in 2026 with superior craftsmanship and high-end finishes, while preserving many original architectural elements. Original boxwood trees remain along the drive, offering a glimpse into the property’s past as you approach the historic farmhouse and its outbuildings. Brick paver walkways lead toward the home and grounds. Step through the original wooden front door to find rich red oak hardwood flooring, solid wood doors and the preserved original staircase. To the left of the foyer, the living room features oversized crown molding and a gas fireplace framed by its original brick surround. To the right, the formal dining room is filled with natural light and enhanced by a tray ceiling and oversized crown molding. Continue to the stunning kitchen, where handcrafted solid wood cabinetry is paired with quartz countertops, a striking hickory wood island and walk-in pantry. Shiplap walls add warmth, while original exposed wooden ceiling beams preserve the farmhouse character. A double-sided fireplace connects the kitchen and adjoining sunroom and features a mantel constructed from fieldstone found on the property. The sunroom features brick flooring, recessed lighting and a fireplace surrounded by original fieldstone. Double doors from the kitchen open onto a brick patio, creating a connection to the surrounding acreage. A beautifully appointed powder room completes the first floor. Upstairs are three bedrooms, two full bathrooms and a dedicated second-floor laundry room. The expansive primary suite offers a walk-in closet, ensuite bathroom and direct access to the third-floor loft. The primary bath features a classic claw-foot tub paired with a frameless glass shower. The third floor offers two additional bedrooms with Jack-and-Jill access to a full bathroom. The finished basement is not to be missed. Portions of the original stone foundation walls have been strengthened, preserved and left exposed as a dramatic architectural feature. Wood-paneled walls and ceilings create incredible ambiance, while Bilco doors provide convenient yard access. While the home's character has been carefully preserved, its infrastructure has been extensively modernized. The 2026 renovation includes all-new electrical and plumbing, roof, Andersen windows, appliances, four HVAC systems and a tankless water heater. Recessed lighting is found throughout, and both the detached garage and barn received new foundations. The property itself is equally remarkable. The oversized, heated 24' x 36' detached two-car garage provides generous parking, workspace and storage. Nearby, the original chicken house remains as another connection to the property’s agricultural past. The impressive 31' x 26' barn features a new foundation and floored upper level for additional storage. Even stormwater management has been thoughtfully considered, with the home's downspouts directed to a rain garden. Historically documented as the Mrs. Templeman Farmhouse and associated with the former Lovett Farm/Chestnut Grove Farm. 220 Nighthawk Drive is far more than a renovated farmhouse. It is the thoughtful restoration of a nearly 200-year-old property where modern systems, luxurious finishes and exceptional craftsmanship have been carefully integrated without erasing its irreplaceable character. From the 5.81-acre setting to the historic farmhouse, barn, original chicken house and preserved architectural details, this is a rare opportunity to become the next steward of an exceptional piece of DE history.

220 Nighthawk Dr, 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

$274,900

3 Beds ⋅ 2 Baths ⋅ DENC2111538 MLS

Coming Soon! 3-Bedroom ranch in Middletown with 2 full bathrooms. Well maintained and ready for its next owners! More info and professional photos coming soon! Mortgage savings may be available for buyers of this listing.

312 Elizabeth St, Middletown

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