Middletown New York homes for sale starting at Fifty Thousand Dollars

$599,999 - Middletown, NY

594 County Route 22 Middletown, NY - MINISINK SCHOOLS - WORK FROM HOME AND HAVE ROOM FOR EXTENDED FAMILY - Nestled at the end of a long driveway is this spacious four-bedroom, five-bathroom home situated on just under four spacious acres. It is absolutely perfect for multi-generational living, offering a separate in-law suite with a kitchenette and bathroom. This home features not one, but TWO primary suites, one located on the main level and the second located on the upper level. The home boasts several generously sized bedrooms as well as additional rooms for dedicated office space, a den or library. The full basement can be used for storage or has the possibility to be finished and has egress windows. Large garage space - 684 square foot two-car garage for your cars or a workshop. Enjoy the country outdoors right in your backyard with a nice stream in the back with active fish, frogs, and crayfish. The rest of the yard is perfect for other outdoor activities and entertaining. Enough room for an RV, camper, company car, build a second garage, or even add a pool! Minutes to Minisink schools, town parks, local restaurants, golf courses, and major highways. Under 20 minutes to Legoland, Garnett Hospital, medical offices such as Crystal Run Healthcare, the mall, and anything else you would need. Easy access into NYC being about a one-hour drive to the GWB. Whether you’re working from home or spending time with your extended family, this house offers the perfect balance of functionality, comfort, and convenience. Don't miss out on this wonderful opportunity to own a home in the fantastic Orange County!

$599,900 - Middletown, NY

718 Mount Hope Road Middletown, NY - Let's welcome the Summer of 2025 with this beautiful and spacious contemporary home. It is nestled up on the hill with great views in the town of Wallkill. This gorgeous home is going to be ready in less than 6 to 8 weeks. The upper level is featuring an open layout with gleaming oak hardwood floors throughout a massive living room with a very high ceiling & built in electric fireplace to a formal dining area and a very wide and spacious gorgeous kitchen with a great size island, granite countertops & stainless appliances. There are two great size bedrooms, a hallway bathroom and a primary master bedroom with two closets and its own master bathroom. All the three bedrooms on the upper level are with hardwood floor and high ceiling. The lower level is where you find your main entrance with a great size foyer to a huge family room great for your entertainment, the 4th bedroom and a full stand up shower with a laundry room and 2 car garages. It's definitely a must see home and it is minutes to NYC Busses and train, major highways, hospital and medical centers and shopping.

$599,000 - Middletown, NY

708 Kirbytown Road Middletown, NY - Such a peaceful setting for this immaculate 4 BR, 2.5 bath Colonial in the heart of The Minisink School District. This home is a dream for pet owners! The fenced backyard keeps your pets safe and secure while they play, and the underground dog fence lets them roam worry-free. There is a woodstove that is perfect for chilly evenings that will help with your heating costs during the cold winter months, a rear deck and firepit for family parties in the summer and a cozy front Trex porch for drinking your morning coffee. This beautifully landscaped, level lot with a garden area is protected from behind by farmland that ensures privacy and tranquility. With multiple sheds you are more than covered for storage of your lawn care items and gardening needs. The partially finished basement adds versatile space for a home office, gym, or playroom. Perfectly located for both convenience and adventure, you're just minutes from major highways and only 1 hour to NYC. Just a short drive to Legoland, The Kartrite Resort, Resorts World Catskill, local breweries, wineries, and scenic trails.

$589,900 - Middletown, NY

658 Ingrassia Road Middletown, NY - Welcome to this beautifully maintained Cape Cod-style home offering 2,628 square feet of versatile living space set on a private and picturesque 2.3-acre lot. This charming residence blends classic design with modern comfort, featuring generous room sizes, abundant natural light, and timeless appeal. The main level boasts a thoughtfully designed floor plan, ideal for both daily living and entertaining. Enjoy a spacious kitchen with ample cabinetry and counter space, a cozy family room with a fireplace, and formal living and dining areas that provide flexibility for hosting guests or relaxing in style. With 4 bedrooms and 2-1/2 bathrooms, this home is perfect for those who crave space to grow. Upstairs, find additional bedrooms and bonus huge walk in closet! Step outside to enjoy expansive outdoor living, with a sprawling yard, mature trees, and plenty of space for gardens, a pool, or future expansion. The peaceful, wooded setting offers privacy and tranquility, all while being just minutes from local amenities, schools, and Routes 17/86 and 84. If you’re looking for a blend of classic country charm, space to spread out, and a serene natural setting, this is the one you’ve been waiting for.

$585,000 - Middletown, NY

83 Dosen Road Middletown, NY - Welcome to your private retreat, perfectly nestled on 4.6 scenic, park-like acres in the heart of the Pine Bush School District. This 1 owner home has 3 bedrooms 2 baths on 1st level, screened in porch off kitchen, enormous living room offers plenty of room for the whole family plus extended family and is ideal for those who love to entertain or simply enjoy the peaceful Hudson Valley lifestyle. Living space featuring cathedral ceilings and an open-concept design that seamlessly connects the living room, dining area, and modern eat-in kitchen. The kitchen boasts granite countertops, a double wall oven, stylish tile floors, and a contemporary backsplash, a perfect setup for both casual meals and holiday gatherings. You'll find three generously sized bedrooms, including a primary suite with ample closet space and its own private bath. A full hallway bath with double sinks adds convenience for family or guests. The lower level boasts, 5 bedrooms and bathroom, boiler room, washer and dryer, large livingroom plus rec room with seperate entrance. Off the kitchen, step out to a spacious screened-in porch and an oversized back deck, ideal for outdoor dining, relaxing, or watching the kids and pets play in the fenced-in backyard. Whether you’re hosting summer BBQs or enjoying fall foliage, the outdoor space truly shines. Major updates include a brand-new roof, new central air conditioning, a recently replaced hot water heater, and a new oil tank, making this home as reliable as it is comfortable. Outside, the home features a detached garage, a large driveway with plenty of parking, and even your very own private pond, adding a peaceful and unique touch to the property. Conveniently located near local farms, wineries, hiking trails, and with easy access to Route 17, this home offers rural tranquility with modern convenience. If you're searching for a well-maintained home with space, updates, charm, and location, this one is a must-see. Don’t miss your chance , schedule your private showing today! Don't let this one get away!

$579,900 - Middletown, NY

30 Daly Road Middletown, NY - New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partially wooded lot. The first floor offers an oversized living room, dining room, a kitchen with granite countertops and stainless appliances, and sliders leading to a backyard deck. Also on the first floor, you'll find a den/study, a laundry room, and a good-sized 1/2 bath. The second floor features a large loft area and 3 bedrooms, including the master suite with an en-suite bath. Central A/C and hardwood floors throughout. A detached 2-car garage is also included. Additional Information: ParkingFeatures:2 Car Detached,

$579,000 - Middletown, NY

1114 Bull Run Road Middletown, NY - 1820s Farmhouse on 89 Acres with Breathtaking Mountain Views. Nestled on a quiet country road, this picturesque 1820s farmhouse offers the perfect blend of historic charm and natural beauty. Set on 89 acres of rolling fields and serene woodland, this three-bedroom, one-bath home features an inviting eat-in kitchen, a cozy living area, and a covered porch perfect for enjoying peaceful mornings and breathtaking sunsets. The house needs some work, so it’s ideal for those looking for a project. The property boasts a large barn, ideal for storage, or a workshop, as well as a detached garage and a two story root cellar for added convenience. A year-round stream meanders through the land, and at the top of the mountain, you’ll be captivated by stunning 360° Catskill Mountain views—a truly remarkable sight in every season. Land on two sides of the road ensures lasting privacy and two very active springs add to the overall value. Whether you’re looking for a country retreat, or a place to build your dream homestead, this exceptional property offers endless possibilities. Don’t miss your chance to own a piece of history in an unbeatable setting! Minutes to the charming village of Margaretville and close to skiing, hiking, fishing, shopping and more!

$540,000 - Middletown, NY

282 Hillys Lane Middletown, NY - Tucked away at the end of a private road in the bucolic Thompson Hollow, this private two-bedroom, one-bath chalet on 14.6 acres is a true Catskills retreat. Backing directly onto 390 acres of NYC DEP forever-wild land, and surrounded by hundreds more acres of protected land, this property offers unmatched peace and seclusion in scenic New Kingston, NY. A 0.16-acre spring-fed pond with a small waterfall and water wheel creates a tranquil focal point, perfect for relaxing or enjoying nature. A short walk from the front door brings you to the stream that winds through Thompson Hollow—an ideal spot to unwind and connect with the landscape. The chalet features two well-sized bedrooms and an open kitchen/living area anchored by a striking fieldstone wood-burning fireplace. Soaring ceilings and a wall of windows fill the space with natural light, and a cozy loft above the main room offers additional sleeping or lounging space. A newly built deck stretches across the front of the home, providing elevated views of the surrounding greenery. Downstairs, the full unfinished basement offers ample storage and workshop potential. Step outside to an impressive covered outdoor dining area complete with a built-in stone BBQ, ceiling fan, and room to host guests. A charming small barn on the property lends itself to multiple uses—studio, storage, or hobby space. Located just 15 minutes from the villages of Margaretville, Roxbury, and Andes, you’ll enjoy easy access to shopping, dining, and local markets. Skiing at Belleayre and Plattekill Mountains is within easy reach, as are hiking, fishing, and all-season outdoor adventure. This one-of-a-kind Catskills property blends rustic comfort, natural beauty, and total privacy—making it a perfect full-time home or weekend getaway.

$535,000 - Middletown, NY

727 Route 17M Middletown, NY - Single Family home and mix-use property in prime location. Live on the property and have your business or use entirely for commercial purposes. This unique property offers incredible potential for various business or residential opportunities in a highly commercial area. Zoned Light Enterprise, this property provides flexibility for special uses, making it ideal for entrepreneurs, tradespeople, or those looking for a live/work setup. This one/two bedroom home offers one bathroom and spans 1088 sf with an additional room. This home features a classic layout with charm and functionality. Open and airy with cathedral ceiling, fireplace, sky light in large kitchen with peninsula, separate laundry room, enclosed porch, and full basement. Additionally, the property includes a detached 400sf garage, perfect for storage, parking, or workshop needs. A separate 360sf work area is also available, ideal for workshop, business, machinery, or additional storage. With its prime location and versatile zoning, this property represents an opportunity for business, investors, or homeowners seeking a strategic and adaptable space. Municipal Water.

$529,000 - Middletown, NY

100 Clear Springs Lane Middletown, NY - THE GREAT ESCAPE - Luxury Turn-Key Ski Retreat Near Belleayre Impeccably maintained 3BR/2BA home on 5 private acres with sweeping mountain views, mature trees, and a quiet cul-de-sac location— just 10 minutes from Belleayre Mountain. Inside, enjoy soaring ceilings, a dramatic stone fireplace, and an open-concept layout perfect for entertaining. Thoughtful upgrades include fully renovated bathrooms with radiant floor heating, heated towel racks, and a spa-style oversized shower in the primary suite. A spacious mudroom entry with custom cubbies offers smart storage for ski gear and outdoor essentials. Outside, relax or entertain on the expansive front deck, gather around the fire pit, and take advantage of extra storage in the detached shed. Whether you're looking for a serene family getaway or a high-performing short-term rental investment, this property offers year-round appeal. Convenient to farm markets, hiking, fly fishing, and the charming villages of Fleischmanns, Margaretville, Pine Hill, and Roxbury—just 2.5 hours from the GWB.

Middletown, New York listings for sale

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