Cuddebackville Real Estate

Welcome to Cuddebackville, a hidden gem nestled in the heart of New York’s picturesque Hudson Valley. This charming hamlet, part of the Town of Deerpark in Orange County, is a delightful blend of natural beauty and small-town charm. With its serene landscapes, Cuddebackville is an ideal retreat for those seeking a peaceful lifestyle while remaining conveniently close to urban amenities.

Cuddebackville boasts a rich history, with roots tracing back to the early 19th century. The area is characterized by its scenic vistas, including the majestic Neversink River, which offers residents and visitors alike a plethora of outdoor activities such as fishing, hiking, and kayaking. The lush greenery and rolling hills create a perfect backdrop for nature enthusiasts and those who appreciate a tranquil environment.

Community spirit thrives in Cuddebackville, where neighbors know each other by name and local events foster a strong sense of belonging. The hamlet is conveniently located near major highways, making it easy to access nearby towns and cities, including Port Jervis and Middletown, where you can find shopping, dining, and entertainment options.

Cuddebackville is not just a place to live; it’s a lifestyle. Whether you’re drawn to the area for its natural beauty, tight-knit community, or historical charm, you’ll find that this quaint hamlet offers a perfect blend of tranquility and connection. Explore the opportunities that await you in Cuddebackville, where your dream home is just around the corner!

Newest Listings in Cuddebackville

$109,900

1049080 MLS

Build your dream home on this partially wooded 5 acre lot on a quiet road. This parcel of land had been engineered and approved for a 4 bedroom single family home. But could be modified to build a attached side-by-side 2 family or attached mother/daughter house as well. Beautiful lot with a stream runs across. Part of the driveway has been built. Previously approved site plan is available. Adjacent Lot is available for sale as well.

143 Brandt Road, Cuddebackville

$109,900

1049079 MLS

Build your dream home on this partially wooded 4+ acre lot on a quiet road. This parcel of land had been engineered and approved for a 6 bedroom single family home. But could be modified to build a attached side-by-side 2 family or attached mother/daughter house as well. Beautiful lot with a stream runs across. Part of the driveway has been built. Previously approved site plan is available. Adjacent Lot is available for sale as well.

145 Brandt Road, Cuddebackville

$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

$235,000

3 Beds ⋅ 2 Baths ⋅ 1034523 MLS

Multi-family investment opportunity featuring a 2-bedroom, 1-bath main home and a detached 1-bedroom, 1-bath guest cottage requiring a full rehab. Situated on approximately 4.70 acres with a stream at the rear of the property, this property offers multiple value-add opportunities, including expansion potential with zoning for an additional 50' x 12' footprint.

153 Kennel Road, Cuddebackville

$59,900

1011186 MLS

Nice 1 Acre Building lot in Great Commuter location. Just 5 minutes to NYC Metro North Train Sation in Otisville - Just 10 minute Drive to Interstate 17 and just 10 Minute Drive to Middletown and Port Jervis which is a Renaissance City complete with upscales shops and restaurants and 45 Miles of Hiking Biking trails and Delaware river recreation. This is a level lot and has been approved through zoning. Just bring your engineer and build the Home of your dreams in a clean rural environment. Two 1 acre lots available.

1176 Us Route 209, Cuddebackville

$312,000

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

$51,500

986814 MLS

Beautiful wooded lot in a desirable location, offering privacy and natural surroundings. Property will require installation of a septic system and well; electricity is available nearby. Buyer's Agent to perform their own due diligence.

1304 Us Route 209, 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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