Middletown New York homes for sale starting at Fifty Thousand Dollars

$2,995,000 - Middletown, NY

40 Camp Orange Road Middletown, NY - This versatile and lucrative investment or user property sits on one of the largest open land parcels left in the Town of Wallkill. Great Location on Route 211 between Middletown and Montgomery. Presently used as a dairy farm with many options for ag business or other type of business. Views would make this a great hospitality site, wedding venue, winery, brewery, ag tourism, retail dairy or farm store and or farm to table. Good productive land with frontage on Route 211. 13,872 SF Dairy Barn, built in 2016 is a clear span metal building with 14 foot high ceilings and concrete floor which could be used as a warehouse type of structure. House is in very good condition. Land is productive with road frontage on two roads and could be potential future subdivision. Barn is 68X204 and there is another 68x96 attached building. 40x60 enclosed shop with over head doors that is 2 years old. Building total sf around 25000. Additional Information: HeatingFuel:Oil Above Ground,

$1,600,000 - Middletown, NY

565 Prosperous Valley Road Middletown, NY - Your dream countryside retreat located in Orange County NY. This custom-built 4,000 sq. ft. Contemporary Ranch is situated on an expansive 61-acre property. (two separate parcels) It includes a two-story 35'x60' barn with 7 horse stalls, a lean-to, a silo, and a tack room. Above the barn, you'll find a 20'x64' loft area with a separate well and 100-amp electric service. The 25'x50' concrete garage is ideal for a workshop. Perfect for hunting ,fishing, ATV riding, and hiking along wooded trails that lead to the Shawangunk Kill, with 1,000 feet of frontage. The one-level living space features soaring cathedral ceilings, a huge family room, a Generac generator, central A/C (two 3-ton compressors), and Andersen windows throughout, including the 20'x25' sky-lit sunroom and heated garage. Is truly a rare find and is also possible subdividable for future development. Located just 75 miles from Manhattan, it offers both convenience and serenity. (2 parcels being sold together )

$1,125,000 - Middletown, NY

255 Howells Road Middletown, NY - Enter the gates of this grand estate, where you'll find a stunning 5-bedroom, 5-bathroom home spanning 4,200 square feet, complete with a large barn and a natural pond, all set on 36.8 acres. This private estate is located in Middletown, NY, nestled among rolling pastures, tranquil woods, and your very own pond. The expansive property also features a two-story post-and-beam barn with horse stalls, wells, and an additional hay barn for storage. The original Colonial estate, built in 1821, serves as the main house. Enjoy horseback riding on your own property, or take advantage of the many recreational activities available, such as farming, hunting, snowmobiling, four-wheeling, and fishing. With too many upgrades to list, this once-in-a-lifetime property is a must-see! Additional Information: Amenities:Storage,

$999,999 - Middletown, NY

941 Mt Hope Road Middletown, NY - Welcome to 941 Mount Hope Road in beautiful Middletown, NY—an exceptional 4,295 sq ft estate set on a sprawling 46-acre property, offering the perfect blend of timeless character and modern upgrades. Built in 1926, this one-of-a-kind stone and siding home has been completely renovated, preserving its historic appeal while elevating comfort and functionality. Whether you're seeking a luxurious primary residence, a peaceful retreat, or a high-potential short- or long-term Airbnb rental, this property offers endless opportunity. Inside, you'll find 4 spacious bedrooms and 3 1/2 bathrooms, including a fully equipped studio apartment with its own full kitchen, walk-in closet, washer and dryer, and private entrance—ideal for guests, in-laws, or additional income. The home offers a warm and inviting flow, with a cozy family room, living room, and a beautiful formal dining room and sunroom combination that fills the space with natural light. A charming den provides the perfect area for kids to relax and play. The home also features two fireplaces and a dramatic spiral staircase that elegantly connects all three levels, serving as a striking architectural centerpiece. The master suite includes a spa-like bathroom with a ceiling-mounted rainfall shower, built-in Bluetooth music, and ambient color-changing lighting, offering a relaxing retreat at the end of the day. Two additional upstairs bedrooms are generously sized to fit king beds comfortably, while a fourth bedroom on the main floor adds flexibility for guests or multigenerational living. With two laundry rooms, a fully updated kitchen featuring stainless steel appliances, and thoughtful upgrades throughout, the home blends charm and convenience. Step outside and enjoy all the land has to offer, including quad trails, garden space, and two scenic ponds—one of which includes a small, tucked-away island with a basic hut and a fireplace, adding a bit of rustic charm to the landscape. Great for occasional fireside chats or quiet moments by the water, it’s a simple but unique feature of the property. There’s also a fishing boat dock already in place, making it easy to cast a line or enjoy the pond. For those interested in homesteading or hobby farming, the property includes two chicken coops: one measuring 4x8 feet within a 15x25-foot run, and another 8x8-foot coop in a larger 30x40-foot run—perfect setups for raising chickens or expanding into other small livestock ventures. A spacious three-car garage provides ample storage, and the RA zoning opens doors for various uses, from personal enjoyment to development or investment opportunities. Additionally there are three commercial buildings present on the property that will need complete restoration or demolition, loads of potential for new vision whether commercial or recreational usage is desired. The home is being sold as-is, with all existing structures included in the sale. Whether you're looking for a one-of-a-kind country estate, an income-generating property, or a versatile piece of land with room to grow, 941 Mount Hope Road delivers the space, features, and charm to make that happen. Schedule your private showing today.

$995,000 - Middletown, NY

494 Fiddlers Elbow Road Middletown, NY - This Nordic style home has undergone a stunning transformation. Driving up the circular driveway to the house the quality, care and beauty are evident. Entering the house you are met with an open, spacious, light filled living area. The living, dining and kitchen areas are a seamless blend of space & light with cathedral ceilings, large windows and a harmonious feeling throughout. The gourmet kitchen has imported Calacatta Italian marble, high end appliances, custom cabinetry and easy access to an exterior deck. The living room has a Jutul wood burning stove with stone hearth, large picture windows and access to two decks. American white oak floors are found through out the house. Integrated Smart Home technology controls the heat, lighting and Nest cameras inside & out. There is a large ensuite primary bedroom on the first floor and two bedrooms and full bath on the second floor. On the lowest level is a bedroom/home office, a safe room, a laundry room, a 1/2 bath and storage. Outside is a greenhouse, a wood bin and a storage shed. Privately sited in the upscale Thornapple Ridge which has a heated pool & a private nature trail. Minutes to skiing, shopping and 2.5 hours from NYC.

$899,000 - Middletown, NY

482 Scotchtown Avenue Middletown, NY - Mint condition, classic, fully-restored 1863 farmhouse. This 4-bedroom, 2 1/2-bathroom home sits on 10 serene acres with stunning horse farm views and features including original hardwood floors, a brick fireplace, and formal dining with exquisite molding. Also noted is the updated plumbing. Enjoy a wraparound porch, a pond with fish, and river access for kayaking. Completely inspiring with a pony barn, goat pen, chicken and duck runs, and a fenced inground pool with a slide. A significant bonus is the separate 2-bedroom, 1-bath cottage with its own entrance, perfectly suited for guests or extended family. 90 minutes from New York City, and only 15 minutes to Stewart Airport and convenient to shopping, this is your ideal escape from the hustle and bustle..

$825,000 - Middletown, NY

104 Elise Drive Middletown, NY - LAST HOME AVAILABLE! Welcome to The Woodlands at Scotchtown Estates! This exquisite picturesque community sits in the highly sought after Valley Central SD, featuring luxury and convenience at your fingertips. Custom built colonials lead the way as you drive down the beautiful tree lined road of this development. This expansive colonial now complete and ready to welcome it's new owners! The main level features gleaming hardwood floors throughout, a formal living room and family room, bedroom with an ensuite, a spacious dining room, chefs kitchen with plenty of cabinetry, laundry room on main level for easy access, and a half bath for convenience. As you make your way up to the second floor, you're welcomed by a large master suite with a full walk in closet, master bath with double vanities, oversized spa like tiles, and a walk in shower. Additionally, there are 3 additional generously sized bedrooms with plenty of closet space and a 600SF bonus room ready for you to create your own space! Appliances and upgraded lighting included!! Close to shopping, restaurants, schools, public transportation, major highways ie: I84 and RT 17. Schedule your appointment today!

$729,000 - Middletown, NY

446 M And M Road Middletown, NY - Luxury meets comfort in this spacious meticulously kept home with bonus room nestled on 3 lush, tree-lined acres in the desirable Pine Bush School District! Designed with both comfort and sophistication in mind, this residence features a 3-car garage with organized work area, central air, and an energy-efficient solar system. The gourmet kitchen includes granite counters, stainless steel appliances, double wall ovens, and a center island—plus a butler’s pantry and first-floor laundry. Main level offers formal dining, living, and family rooms, plus a half bath. Retreat to the primary suite with jacuzzi tub, water closet, shower, dual sinks, and walk-in closet. All bedrooms have walk-in closets; Jack & Jill main bath. Enjoy a walk-out basement with 9-ft ceilings, workstation, and simulated golf. Backyard is an entertainer’s dream or your own private oasis --complete with heated in-ground pool with built-in tanning shelf and slide, 40x16 Trex deck, patio, and lighting. Also includes generator setup, whole-house vacuum, wall-mounted power washer, water filtration system with reverse osmosis and much more. Too many features to list. Check out the Video Tour link for more pics and details, then come see for yourself!

$699,000 - Middletown, NY

200 Mt Orange Road Middletown, NY - Welcome to this most charming 1870's farmhouse situated on idyllic 6.4 level pastoral acres with small pond. This property boasts wide moldings and other intricate detailing that showcase the exceptional craftmanship that went into its construction. Enjoy both gorgeous sunrises and sunsets from almost any room. This home has been well maintained, with some newer additions, such as the family room. It presents an excellent opportunity to create a unique living space that incorporates the original charm and character of the home with modern amenities. Hardwood floors are under many of the carpeted areas. One of the highlights of the property is the large 45X90 garage workshop. This space offers endless possibilities, and could be used for a variety of purposes. Enjoy its beautiful natural surroundings, mature trees, open fields and pond. Located in a beautiful area, a great location, only minutes to I84, 17M, shopping. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:3 Car Detached,

$695,000 - Middletown, NY

2185 Hog Mountain Road Middletown, NY - MODERN ARCITECTURAL GEM ON 7.25 ACRES WITH HISTORIC BARN AND PANORAMIC VIEWS. Step into contemporary elegance with this architecturally designed, single-level home, completed in 2023 and barely lived in, offering the pristine feel of new construction. Nestled on a picturesque parcel with 2 ponds, this thoughtfully crafted residence blends modern design with warm, natural materials, delivering both luxury and comfort in every detail. The open-concept Great Room with soaring 15' ceilings and a striking 16-foot wall of glass seamlessly unites the living, dining, and kitchen spaces while framing panoramic views of the tranquil surroundings. Wide-board maple floors and custom lighting set a refined tone, while a propane fireplace adds warmth and ambiance. Each wing of the home boasts its own spacious primary suite, ideal for privacy and each complete with 8' French doors out to a deck, walk-in closets, & spa-style baths featuring stepless open showers, radiant heated tile floors, and elegant vanities. The kitchen is a chef's dream with quartz countertops, a breakfast bar, farmhouse sink, and stainless steel appliances, including a 6-burner propane range, side-by-side refrigerator, dishwasher and microwave. An adjacent laundry room and pantry enhance the home’s functionality. PREMIUM FEATURES: Foyer with tiled half bath. Cathedral ceilings range from 12’ to 15'. 8' custom plantation pine doors throughout, including 8' sliders to the back decks. (4) mini-split systems & radiant bathroom floors and a propane fireplace for customizable climate control. Heated closets and ceiling fans in great room and bedrooms. The home sits atop a high-ceilinged, poured concrete basement, offering future potential for additional living space. EXTERIOR & GROUNDS: Handicap-accessible ramp. Durable standing seam metal roof and 6” metal half-round gutters. Steel cable deck railings, hot/cold outdoor spigot, rain chain downspouts. Backyard firepit—perfect for evening gatherings under the stars HISTORIC BARN: The converted dairy barn features a 60-amp electric panel and a spacious high-ceiling hayloft upstairs—ideal for a studio, workshop, or storage area

Middletown, New York listings for sale

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