Middletown, New York listings for sale

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$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.
1928 | 1 | 1 | 1,088 sqft.
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$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.
1987 | 3 | 2 | 1,428 sqft.
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$525,000 - Middletown, NY
7 Highland View Place Middletown, NY - Welcome home to this beautifully maintained 5-bedroom, 4-bathroom raised ranch, ideally situated near the highly-rated Presidential Park Elementary School in Middletown, NY. Perfect for growing families or multi-generational living, this expansive home offers generous living space, natural light throughout, and thoughtful updates that make it move-in ready. Step inside to discover an open-concept main floor with gleaming hardwood floors, a large eat-in kitchen with stainless steel appliances, and a spacious living room perfect for entertaining. The primary suite includes a private bath, and the lower level features additional bedrooms and a full bath — perfect for guests or an in-law suite. Step outside to your oasis: an oversized deck overlooking a meticulously landscaped backyard — ideal for summer BBQs, gardening, or simply relaxing in privacy. Located in a quiet, family-friendly neighborhood just minutes from local parks, shopping, and dining, this home combines convenience with comfort. With easy access to I-84 and Route 17, commuting is a breeze. Don’t miss this rare opportunity to own a versatile, spacious home in one of Middletown’s most desirable school zones!
1965 | 5 | 4 | 3,140 sqft.
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$510,000 - Middletown, NY
612 Shoddy Hollow Road Middletown, NY - Located on one of the most scenic and peaceful roads in Orange County, this spacious mother-daughter home offers exceptional privacy on a full acre of land, just minutes from Middletown shopping, dining, and NYC train access. Tucked away on a quiet road, the home provides a rare sense of seclusion while still being close to everyday conveniences. Inside, you’ll find two full kitchens with stainless steel appliances, making it ideal for extended family living, guests, or rental possibilities. The lower-level apartment offers step-free entry through the oversized heated two-car garage, providing easy single-level living. Outdoor living is just as inviting, with two separate decks perfect for relaxing, entertaining, or enjoying the surrounding nature. The property is equipped with a newer roof that was replaced in the last 2 years with solar panels — a valuable feature for today’s energy-conscious buyers. The flexible layout supports multigenerational living, with separate entrances and plenty of space to spread out. Expanded driveway makes it really easy for bigger cars or big family gatherings this summer. Located in the desirable Minisink Valley School District, the home also features oil heat (above ground tank), an easy-to-maintain yard, and an upgraded water system all throughout the home. This is a unique opportunity to enjoy space, privacy, and smart living — all in one beautiful package.
1988 | 4 | 3 | 2,160 sqft.
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$499,000 - Middletown, NY
1302 Swart Road Middletown, NY - Escape the ordinary in this enchanting 1963 mid-century modern retreat just outside Margaretville, set on 20 serene acres bordering 35 acres of pristine NYC DEP land. A rare find for those seeking character, this eclectic 3BR, 3.5BA home blends vintage charm with thoughtful updates—including a stunning newly renovated kitchen perfect for culinary inspiration. Spacious bonus rooms invite creativity, while the attached garage adds convenience. If you’re weary of cookie-cutter houses, you’ll fall in love with this home’s soul. A grand dairy barn, with a finished main floor, offers endless potential—studio, workshop, or what ever, Much love has been poured in, with just a bit left to make it your own. A true Catskills gem waiting to be discovered.
1963 | 3 | 4 | 2,898 sqft.
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$479,999 - Middletown, NY
919 Silver Lake Sctn Road Middletown, NY - This beautifully maintained home sits on a full acre of flat, usable land in a lovely, quiet, and peaceful area—yet you're just minutes from shopping, entertainment, the train station, and major highways, making your daily commute a breeze. Offering 4 spacious bedrooms and 2.1 bathrooms, this home features modern updates throughout and a layout designed for comfort and functionality. Enjoy summer days or cozy evenings on the large deck or relax under the charming pergola—perfect for entertaining or unwinding after a long day. Additional highlights include central air, a two-car garage, plenty of parking, a full basement with abundant storage, and a water filtration system with reverse osmosis for pure, clean water throughout the home. The property also features well water with public sewer and a school bus stop right at your doorstep. Located in the desirable Pine Bush School District, this home offers the perfect balance of privacy, space, and convenience.
1980 | 4 | 2 | 1,664 sqft.
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$479,000 - Middletown, NY
38 Woodside Knolls Drive Middletown, NY - Welcome to Woodside Knolls! Discover this stunning tri-level townhouse located in one of the area’s most desirable communities. This beautifully maintained home features 9' ceilings on the main level, a bright white kitchen with granite countertops and stainless steel appliances, and gleaming hardwood floors throughout the main level. Enjoy 3 spacious bedrooms and 3.5 bathrooms, including a fully finished basement with a full bath—perfect for guests, entertainment space, or home office. The oversized double garage offers ample storage and convenience. Community amenities include a swimming pool, tennis courts, basketball court and a children’s play area, all nestled in a well-kept, friendly neighborhood. With low taxes and easy access to shopping, transportation, and major highways, this townhome offers the perfect blend of comfort, style, and convenience.
2008 | 3 | 4 | 1,899 sqft.
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$479,000 - Middletown, NY
16 Beth Drive Middletown, NY - Welcome to this charming bilevel home that combines classic comfort with contemporary upgrades. Situated in a desirable neighborhood, this residence offers a perfect retreat for family living and entertaining. Main Features: Updated Interiors: ** Recent renovations include a modern kitchen with stainless steel appliances, updated countertops, and custom cabinetry. The bathrooms have been refreshed with new fixtures, tiles, and vanities. The living spaces feature hardwood floors. The home offers 3 spacious bedrooms and 2 full bathrooms and 1 half. The lower level provides a cozy family room, perfect for movie nights or relaxing with loved ones and great for entertaining. Step outside to your private backyard oasis featuring a large, maintenance-free deck ideal for barbecues, outdoor dining, and relaxing with friends. The deck overlooks the inviting swimming pool, perfect for hot summer days. Additional Features are Attached garage, ample storage, and a landscaped yard complete this wonderful home. This bilevel home beautifully blends comfort, style, and outdoor enjoyment. Don't miss the opportunity to make it your new home!
1985 | 3 | 2 | 1,540 sqft.
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$465,000 - Middletown, NY
450 Mt Orange Road Middletown, NY - Welcome to this move in ready, spacious and versatile 4-bedroom, 3-bathroom bi-level home located in Minisink Valley School District. Thoughtfully designed and meticulously maintained, this home offers comfort, flexibility, and the potential for multigenerational living. Upstairs features 3 bedrooms and 2 full bathrooms, including a private en-suite in the primary bedroom. Gleaming hardwood floors flow throughout the main living areas, creating a warm and inviting atmosphere. The open-concept kitchen, dining and living room area are perfect for gatherings and overlook the landscaped front yard, adding to the home's curb appeal. The lower level offers a second living area and an additional full bathroom, with flexible living space ideal for a fourth bedroom, guest suite, in-law setup, or home office. Additional features include a paved driveway, two car attached garage, new water softener system. Close to schools, parks, shops and less than 65 miles to the GWB make is a great commuter location as well.
2008 | 4 | 3 | 2,100 sqft.
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$450,000 - Middletown, NY
484 Route 211 W Middletown, NY - Welcome to 484 Route 211 – an amazing opportunity in the heart of Middletown for anyone ready to take on a rewarding project with big potential! This spacious home features 4 generously sized bedrooms and 2 full bathrooms, offering plenty of room for a large or growing family. The eat-in kitchen is perfect for family meals, and there’s even a first-floor bedroom for added convenience. One of the standout features of this property is the attached in-law suite—while it could use a little TLC, it holds incredible promise as an extended living space or even a potential rental unit for added income. Other highlights include an updated roof, a separate laundry area, and a fantastic location close to shops, schools, gas stations, and more. If you’re a pet lover, you’ll be glad to know there’s even a dog daycare just down the road! This home is being sold as-is, but with the right vision and some updates, it could become a true gem. Don’t miss this chance to own a property in one of Middletown’s most convenient locations. Make your offer today and take advantage of this summer opportunity!
1949 | 4 | 2 | 2,531 sqft.