Middletown Homes for Sale

Welcome to Middletown, New York – a hidden gem nestled in the heart of Orange County! With its rich history, vibrant community, and picturesque landscapes, Middletown offers the perfect blend of small-town charm and modern convenience. Situated just 70 miles northwest of New York City, this city is an ideal haven for those seeking a peaceful lifestyle without sacrificing access to urban amenities.

Middletown boasts a diverse array of homes for sale, catering to various tastes and budgets. Whether you're searching for a cozy starter home, a spacious family residence, or a charming historic property, you’ll find it all here. The real estate market in Middletown is thriving, with options that include contemporary townhouses, elegant single-family homes, and even sprawling estates nestled in serene surroundings. Each neighborhood has its unique character, providing a welcoming atmosphere that encourages community engagement.

For outdoor enthusiasts, Middletown is surrounded by stunning natural beauty, featuring parks, hiking trails, and recreational opportunities. The nearby Hudson Valley offers breathtaking views and outdoor adventures, making it a perfect playground for nature lovers. Additionally, the city is home to a variety of shops, restaurants, and cultural attractions, ensuring that there’s always something to explore.

If you’re considering making Middletown your home, now is the perfect time to dive into the local real estate market. With a range of homes for sale, you can find the ideal property that suits your lifestyle and budget. Embrace the charm of Middletown and discover the perfect place to call home!

Newest Middletown Homes for Sale

$874,900

3 Beds ⋅ 3 Baths ⋅ MDFR2089196 MLS

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

$725,000

4 Beds ⋅ 3 Baths ⋅ 1045550 MLS

Tucked away at the end of Roaring Brook Lane in the desirable Owl's Nest subdivision, this contemporary chalet offers a private Catskills retreat on five peaceful acres. Tastefully updated and very well maintained, the home has been enjoyed by the current owners as both a weekend getaway and a successful short-term rental, earning Super Host recognition for the past four years. Step inside through the spacious mudroom--an ideal landing spot for skis, boots, hiking gear, and everything that comes with four-season Catskills living. From here, enter the heart of the home: a bright and welcoming kitchen featuring gleaming granite countertops, stainless steel appliances, abundant workspace, and an oversized island with breakfast bar seating. Designed for both everyday living and entertaining, the open layout makes cooking and conversation feel effortless. Just beyond the kitchen, the dining area flows into the inviting living room, where soaring cathedral ceilings and a fireplace create a warm and cozy gathering space. The primary bedroom is conveniently located on the main level and offers its own fireplace along with a private full bath featuring a soaking tub and separate walk-in shower. A second full bath on the main level provides added convenience for day-to-day living. Upstairs, two additional bedrooms and another full bathroom provide comfortable accommodations for guests. Outdoor living is equally inviting. Unwind in your personal hot tub after a day on the slopes, gather under the gazebo, or enjoy the surrounding woods and fresh mountain air from the wraparound deck. The setting offers a wonderful sense of seclusion while remaining close to some of the Catskills' most popular destinations. Located next to Belleayre Mountain Ski Center in southern Delaware County, the property offers easy access to skiing, hiking, outdoor recreation, dining, shopping, and year-round activities. Phoenicia, Woodstock, and other beloved Catskills destinations are within reach, while New York City is just under three hours away. Whether you are searching for a full-time residence, weekend escape, or established short-term rental opportunity, this Highmount retreat offers privacy, comfort, and four-season Catskills living in an exceptional location.

1270 Roaring Brook Lane, 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

$249,900

3 Beds ⋅ 1 Baths ⋅ PADA2064140 MLS

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

$175,000

3 Beds ⋅ 2 Baths ⋅ VAFV2044778 MLS

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

$1,885,000

2 Beds ⋅ 2 Baths ⋅ 1048430 MLS

Exceptional 33.6-acre equestrian property in the Town of Wallkill, thoughtfully developed for serious equestrians. Classified by Orange County as a Horse Farm and located within an NYS Agricultural District, it features a substantial barn complex, indoor and outdoor riding arenas, numerous paddocks and turnout areas, supporting structures, and a two-bedroom apartment for on-site living. The grounds include approximately 15 medium-size grass paddocks, 8 smaller sand paddocks/turnouts near the barn for winter and inclement-weather use, a dedicated medical turnout, and a fenced field of approximately 6.5 acres with an interior fenced area surrounding a 30 x 64 loafing shed built in 2013. The shed includes a 12 x 16 stall, feed room, storage room, and 30 x 48 matted area with wall-mounted hay feeders, providing flexibility for turnout, rotation, rehabilitation, and herd management. Many exposed wood edges are protected by metal edging to help prevent chewing and reduce wear. Each paddock has access to one or more Nelson automatic waterers. Numerous frost-resistant outdoor faucets, plus one in the barn, provide backup access to fresh water, while electrical outlets throughout the grounds support water heaters, tools, and daily needs. Built in 2007, the main barn is designed for efficient horse care. A 16-foot-wide center aisle serves 8 approximately 12 x 12 stalls, each with rubber mats and Nelson automatic waterers. Two wash/grooming stalls feature hot and cold water and heat lamps. A climate-controlled tack room offers protected storage for saddles, bridles, and equipment. A dedicated feed room includes a storage closet. A separate utility room has a washer and dryer, with numerous closets throughout the barn for organization. A camera system provides coverage in each stall and throughout the barn. Above, a massive hayloft includes storage closets and individual hay chutes serving the stalls below. It accommodates approximately 1,400–1,600 oversized 50–55 lb. bales of hay, plus substantial bedding-pellet storage on a reinforced plywood section suitable for pallet-jack movement. Covered ventilation hatches provide airflow and protection from the elements. A heated and air-conditioned barn lounge offers year-round comfort for riders, trainers, staff, and guests and is appointed with quality cabinetry, granite countertops, sink, microwave, under-counter refrigerator, tile flooring, and recessed lighting. A heated and air-conditioned half bath is appointed with quality finishes. The approximately 1,280 sq. ft. two-bedroom apartment features an open living layout, granite kitchen with generous cabinetry and peninsula offering additional workspace and seating potential, full bath, and utility/laundry area, well suited for an owner, trainer, barn manager, staff member, or guests. The 84 x 214 indoor riding arena is equipped with TravelRight dust-free footing for comfortable year-round riding and training and is complemented by a 130 x 235 outdoor arena. Permanent four-board and no-climb top-board fencing, gates, established lanes, and an organized barn-and-paddock layout enhance day-to-day horse management. An automatic entrance gate provides controlled access. A backup generator supports the property during outages, while a hand pump on the well offers another means of obtaining water for animals during a prolonged outage. Conveniently located a short drive from Route 17/I-86 Exit 119, the property combines easy regional access with the privacy and space of a country equestrian setting. The acreage, extensive infrastructure, riding facilities, and on-site accommodations create a rare opportunity to acquire an established horse property in the Middletown/Town of Wallkill area. Available as 120 Shaw Road on its own or as a package with 174 Shaw Road, adding approximately 3.8 acres and an additional building site for expansion, future development, residential use, or enhanced equestrian operations.

120 Shaw Road, Middletown

$539,000

3 Beds ⋅ 3 Baths ⋅ DENC2110072 MLS

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

$550,000

4 Beds ⋅ 3 Baths ⋅ 1049857 MLS

Beautiful home for Sale that features 4 bedrooms with 2.5 baths in a desirable area of Middletown just minutes from Orange County Community College. Do NOT let the outside fool you as this home is bigger than expected inside as it has many finished levels! Newly remodeled and ready for its final touches. Open floor layout from Living room to dining room & kitchen all with newly stained hardwood floors. The kitchen features new cabinets, granite counters and new stainless steel appliances right out the box! 4 bedrooms are located on the upper level, one which is a Suite with its own private bath and shower. Completely remodeled tiled bath with new toilet vanity & sink. A 2nd full bathroom with a tub AND tiled shower completes the upper floor. Again all new top to bottom! A finished lower level offers a Family room, office, and a 3rd half bath along with a laundry room with a new washer & dryer! So much open space is found in this level ideal for an oversized family room, entertainment area, office or workout room. The basement is ALSO finished adding more than enough storage space if it’s needed. Nice size yard that just needs to be cleaned up ideal for gathering & entertaining. Grill and enjoy morning coffee right off the newly pavered patio!!! Plenty of parking along with a 2 car garage. Among some of the upgrades this home offers are the new roof, baths, kitchen, new mechanicals and more! Close proximity to Schools, Colleges, Touro Medical, Garnet Health, and shopping. Call and make this house your home! (AS-IS SALE)

44-50 Ingalls Street, Middletown

$569,900

3 Beds ⋅ 3 Baths ⋅ DENC2111116 MLS

Superb colonial located on private, nearly 3/4 acre lot in the ever popular community of Thomas Cove!! Enter this home through the dramatic two story foyer, formal living room w/crown molding, spacious dining room w/laminate flooring, crown molding and ceiling fan, oversized family room w/gas fireplace and newer carpeting and spacious kitchen w/12x12 ceramic tile flooring, island and newer range and dishwasher. Upstairs included owners suite with vaulted ceiling, ceiling fan and walk-in closet, soaking tub, laundry and generous sized secondary bedrooms. Full basement, paver patio, brand new deck, updated HVAC, roof and hot water heater, and the list goes on. Don't miss this gem!!

127 Middessa Dr, Middletown

$465,000

3 Beds ⋅ 1 Baths ⋅ 1020678 MLS

Welcome to this charming Middletown home offering classic character, comfortable living, and great curb appeal. The inviting covered front porch sets the tone as you enter a home filled with warmth and natural light. The spacious kitchen features an abundance of cabinetry, ample counter space, and stainless-steel appliances, providing plenty of room for everyday cooking and entertaining. Outside, enjoy a generous front lawn and private driveway with convenient off-street parking. Ideally located in Middletown with easy access to shopping, dining, schools, parks, and major roadways. Whether you're looking for a place to call home or an opportunity to make it your own, this property is ready to welcome its next owner. Schedule your showing today!

13 Columbia Avenue, Middletown

$215,000

3 Beds ⋅ 1 Baths ⋅ PADA2063256 MLS

This delightful traditional home located in Middletown borough offers a perfect blend of comfort and potential. Built in 1930, the residence exudes character with its traditional design, inviting you to create lasting memories within its walls. This home features two bedrooms and a full bathroom on the main level. The bonus second level provides additional space with third bedroom and a flex area and additional storage. The inviting front porch creates a warm atmosphere that feels just like home for relaxing on summer evenings. The unfinished basement, accessible from both interior and exterior, presents an exciting opportunity for future customization to fit the new owner's needs. Step outside to discover the charming rear yard, perfect for summer gatherings, gardening, or simply just relaxing . This property is conveniently located with both on-street and off-street parking options, and is also close to local amenities for shopping, dining and easy highway access. Whether you’re looking to settle down or invest in a property with great possibilities, this Middletown gem is ready to welcome you home. Embrace the opportunity to make this space your own and enjoy the comfort and community this home has to offer. * Listing agent is related to seller.

215 Hoffer St, Middletown

$415,000

3 Beds ⋅ 2 Baths ⋅ MDFR2089156 MLS

3 bed 1.5 bath split foyer with garage, walkout basement with den, office, and storage at the end of cul de sac. Replaced within the last 5 years: roof, hvac, sewer main, flooring, paint. Located in Fountaindale neighborhood. Middletown school district. 8 min drive to Golden Mile.

7101 Flint Ct, Middletown

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.