Cuddebackville Homes for Sale

Welcome to Cuddebackville, a hidden gem nestled in the heart of Orange County, New York. This charming community offers a unique blend of rural tranquility and modern convenience, making it an ideal destination for families, retirees, and anyone seeking a peaceful lifestyle. Surrounded by lush landscapes and scenic views, Cuddebackville is perfect for nature enthusiasts and outdoor lovers, with easy access to hiking trails, rivers, and parks that showcase the beauty of the Hudson Valley.

Cuddebackville boasts a rich history, evident in its quaint architecture and friendly neighborhoods. Here, you’ll find a close-knit community that values both tradition and progress. The town is conveniently located near major highways, providing easy access to nearby cities and amenities while maintaining its serene atmosphere. Local shops, eateries, and markets contribute to a vibrant community spirit, making it easy to connect with neighbors and enjoy the charm of small-town living.

For those looking to find their dream home, Cuddebackville offers a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re searching for a cozy cottage, a spacious family home, or a modern retreat, you’ll discover properties that reflect the warmth and character of this delightful town. With its stunning landscapes, friendly community, and affordable housing options, Cuddebackville is a place where you can truly feel at home. Explore the available listings today and take the first step toward your new beginning in this enchanting corner of New York!

Newest Cuddebackville Homes for Sale

$1,500,000

13 Beds ⋅ 6 Baths ⋅ 1044137 MLS

Grand estate residence on 149 acres, including 20+ acres of a Hazel Nut farm. The original orchard trees were planted in 2010 and have been successfully harvested and brought to market in the Hudson Valley and New York City areas. Aside from the working orchard, the grounds have numerous specimen trees and plantings – some dating back to the early 1900s and prior. The spacious main residence features 6 bedrooms, 4 full bathrooms, and powder room. Your spacious primary bedroom and ensuite bathroom are located on the first floor in addition to a second bedroom/office and full bathroom. Four Bedrooms and 2.5-bathrooms are located on the second floor. The updated kitchen has a gas range with vented hood and stainless-steel appliance package, wood cabinetry, composite countertops, and breakfast counter. The dining room and living room each have working wood-burning fireplaces and provide access to a large wrap sunroom with wood-burning stove, large windows, and French doors that lead to your private stone patio. Living areas have hardwood and tile floors throughout, and ceiling fans are located in every room. The main home features plenty of closets, built-ins, large-scale bedrooms, an attic, large second floor deck (providing views of the grounds) laundry closet with LG washer/dryer, and so much more. Vehicle storage on the property is a car-collector’s dream. The main garage with a depth for 2 cars has a second-floor studio space with a half bathroom that is great for quiet, creative artistry, office, or short-term visitors. The second garage/workshop has depth and width to accommodate 4 vehicles and work areas. There is also an additional 5-6 bay garage and maintenance building, with a 3-bedroom, 2-bath apartment above. The inground swimming pool is complete with planted patio, diving board, and mechanical shed, with room for the pool toys. There are stone walls, extensive wooded acreage, two greenhouses, flower gardens, rolling hills, and mountain views complete this grand estate property. Proximate to Monticello Resorts World Casino, Monticello Motor Club, the Delaware River, Breweries, Wineries, excellent restaurants, shopping, and numerous options for outdoor adventures.

151 Prospect Hill Road, Cuddebackville

$409,999

3 Beds ⋅ 2 Baths ⋅ 1046129 MLS

This is a must see Beautiful Ranch home on private road close to the elementary school, trains in Otisville and Port Jervis. take a short drive down Galley Hill Road to Benton Drive to see this inviting property and home with a welcoming half moon driveway and welcoming porch. You will notice outside that there is a carport, a two car garage and shed for storage of outdoor items. You will also see the large deck for entertaining family and friends who will also enjoy the fire pit for those cooler days and nights. Upon entering the homes foyer you will be greeted by the warmth of the hardwood floors and the open floorplan with the living room and dining room which is just off the galley kitchen with quartz counter tops. The appliances all stay. Off the kitchen is the laundry (which also stays)and pantry. To the left of the foyer is the master bedroom with a double door closet and a walk-in closet and the en-suite. At the other end of the home is a full bath, an office / bedroom, and a 3rd bedroom. Both rooms are carpeted and each have double door closets. Then take a walk down the carpeted steps to the full size basement where you will notice the walls are studded out waiting to be finished off, the 200 amp electric service recently updated. Th owner has his work shop in the other half of the basement which also has the boiler, hot water heater and two oil tanks all well maintained. The possibilities in the basement are endless and only limited by your imagination. You won't want to miss seeing this home. There are two additional double lots included in the sale SBL 32-4-3 and SBL 32-4-4

17 Benton Drive, Cuddebackville

$299,000

3 Beds ⋅ 2 Baths ⋅ 1004038 MLS

**Nestled on 1.9 acres framed by timeless stone walls and mature trees, this isn’t just a home—it’s a hideaway.** Quiet, private, and filled with natural light, this 3-bedroom, 2-bath retreat is the kind of place you discover and never want to leave. From the moment you walk in, the oversized windows steal the show—flooding the space with light and letting the outside in. The first floor features easy-living with laminate floors throughout, a generous kitchen ready for everything from Sunday pancakes to last-minute takeout, and a cozy bedroom that keeps things flexible. Laundry is conveniently on the main level—no hauling baskets up and down stairs. Out back, a wide deck stretches into the peaceful yard, perfect for grilling, unwinding, or watching the stars put on a show. Upstairs, the primary suite is seriously oversized—your own personal retreat with a private bath and plenty of room to spread out. A third bedroom, tucked upstairs, adds even more possibilities: guest space, office, art studio—you name it. Mechanically, the home checks all the boxes: the roof is just about two years old with 50-year shingles, the heating and central air systems are under 10 years old, and there’s a **whole-house generator** for year-round peace of mind. And the location? Just 20 minutes to Route 17 and I-84 in Port Jervis—right near the **New Jersey and Pennsylvania borders, the Delaware River, and local shopping.** Whether you're commuting, adventuring, or running errands, you’re right where you need to be. If you’ve been searching for that rare mix of character, space, and serenity—this is it. The kind of place where you exhale the second you pull into the driveway.

68 Kennel Road, Cuddebackville

$239,000

4 Beds ⋅ 1 Baths ⋅ 911821 MLS

Welcome to this adorable & maintained ranch-style cottage offering comfort, convenience, and instant rental income. The open floor plan maximizes natural light and easy living. This makes an ideal turnkey opportunity for investors seeking stable cash flow from day one or move right in! Situated on a peaceful street, the sale also includes an additional parcel located at 8 Old Road, offering even more value and potential for future use. Whether you’re expanding your portfolio, entering the investment market, or looking for a starter home, this charming cottage delivers low-maintenance living, strong rental history, and plenty of upside.

4 Old Road, Cuddebackville

$585,000

2 Beds ⋅ 1 Baths ⋅ 911578 MLS

Welcome to Kiernan Glen a beautiful generational property for your mini-estate, compound or camp! It's a"get everyone together" country homestead offering an Amazing Rare Opportunity to Own Two Homes, adjacent parcels (one with deeded rights to the Basha Kill running by property) and abutting 11.6 Acres of land for privacy that are all included in this sale. As you ride down the country road and turn into the tree-lined drive along the fields to the Main House you'll be stepping back in time to imagine the days when relatives and friends visited and gathered making memories that are still being shared today. The main house has a vintage flair throughout with an original stone fireplace. The separate nearby house is a one floor guest ranch home that was built later. This sale is an "As Is" sale of all included and all inspections by buyers would be for buyers benefit only no warranties by the sellers. Due to the uniqueness of the property and all that is included it must be seen to be appreciated and see firsthand all that's included for the potential offered with this sale not only for its private location but to see and experience the beauty of this country property. You'll be able to embrace the charm of a bygone era as you immerse yourself in planning how you can blend it all with your upgrades to your lifestyle and today's needs. It's where you will make new lasting memories on this beautiful country property!!

12 Kiernan Glen, Cuddebackville

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