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

$549,000

4 Beds ⋅ 3 Baths ⋅ 1023084 MLS

Welcome to this beautiful and spacious contemporary home perfectly set on 3.11 private acres. This impressive property offers the perfect blend of comfort, style, and convenience with an open-concept design and exceptional living space throughout. The upper level features gleaming oak hardwood floors, soaring high ceilings, and a massive living room with a stunning built-in electric fireplace that flows seamlessly into the formal dining area. The gorgeous oversized kitchen is designed to impress with a large center island, quartz countertops, and stainless steel appliances — perfect for everyday living and entertaining alike. You’ll also find two generously sized bedrooms, a full hallway bathroom, and a spacious primary suite complete with two closets and a private master bathroom. All three upper-level bedrooms feature hardwood flooring and high ceilings, adding warmth and elegance throughout. The lower level welcomes you with a spacious foyer leading to a huge family room ideal for entertaining, a 4th bedroom, a full bathroom with a stand-up shower, laundry room, and access to the attached 2-car garage. The pictures are from previous house that was built in 2025. It has similar style and size with some upgrades with additional costs plus central ac is additional cost. The property is on the left side of the driveway.

470 State Route 211, Cuddebackville

$29,975

3 Beds ⋅ 1 Baths ⋅ 1021795 MLS

FULLY AVAILABLE NOW! Being valued for land only with working well. Remove this mobile home and place your dream mobile home on this lot with current well. Double sized lot 100x100, Includes Carport. Only Full Priced offers will be considered. Rear yard construction materials belong to a separate lot.

35 Grove Street, 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

$549,000

4 Beds ⋅ 3 Baths ⋅ 1006433 MLS

Welcome to this beautiful and spacious contemporary home perfectly set on 2.77 private acres. This impressive property offers the perfect blend of comfort, style, and convenience with an open-concept design and exceptional living space throughout. The upper level features gleaming oak hardwood floors, soaring high ceilings, and a massive living room with a stunning built-in electric fireplace that flows seamlessly into the formal dining area. The gorgeous oversized kitchen is designed to impress with a large center island, quartz countertops, and stainless steel appliances — perfect for everyday living and entertaining alike. You’ll also find two generously sized bedrooms, a full hallway bathroom, and a spacious primary suite complete with two closets and a private master bathroom. All three upper-level bedrooms feature hardwood flooring and high ceilings, adding warmth and elegance throughout. The lower level welcomes you with a spacious foyer leading to a huge family room ideal for entertaining, a 4th bedroom, a full bathroom with a stand-up shower, laundry room, and access to the attached 2-car garage. It will be early to mid September 2026. Ps. The pictures are from previous house that was built in 2025. It has similar style and size with some upgrades with additional costs plus central ac is additional cost. The property is on the left side of the driveway.

506 State Route 211, 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

$7,000

974658 MLS

Just reduced . seller has life event. can not keep the land. was listed at $ 11,500 now selling price $7,000 cash buyers only.property has an old foundation on the upper part. nice old time stone work. blue stone steps. roof is no longer. time has caused it to no longer function. is on the ground. all ways stop in and check with the town office and building inspector on what plans you might be thinking about for the property. check with the Orange County Planning Board and building inspector on rt 209. may be it is grand fathered.? one of those tiny homes might fit? or use car sales? or land scaper equipment storage building shed? dimentions are rt 209 road frontage 104 feet.225 feet on Brandt Road back line 101 feet side 222 feet 5 minutes from rt 17 east and west. on route 209 usually if a property has been vacant over a year. new usages need to talk with town? they can give you the information you need. neighbors mentioned that the cute little building. use to be a little school house back in the day. good location heavy traffic flow for visibility.

1501 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

$650,000

2 Beds ⋅ 1 Baths ⋅ 911578 MLS

Welcome to Kiernan Glen a very Special Country Place for your "get everyone together" Mini Estate. Compound or Camp! Amazing Rare Opportunity to Own Two Homes, adjacent parcels (one with deeded rights to the Basha Kill running by property) and adjacent 11.6 Acres of a beautiful field that are all included in this sale. As you ride down the country road and turn into the tree-lined drive along the field to the Main House you'll be stepping back in time to 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 for a good understanding of all included and the potential offered with this sale not only for its private location plus to see firsthand the beauty of this country property. You'll be able to experience the charm of a bygone era here and plan how you can compliment it all with your upgrades to your lifestyle and today's needs. Make new lasting memories now!

12 Kiernan Glen, Cuddebackville

$475,000

8 Beds ⋅ 4 Baths ⋅ H6286653 MLS

All things are possible with this one! Live in one & rent the other 3 units out or bring your extended family/guests and host all the holiday gatherings. Whether you're seeking a multi-generational living arrangement or an investment opportunity this property offers excellent possibilities. The main house is a 2-family. One unit with 3-4 bedrooms, 1-2 baths, (a new 408 Sqft addition that’s partially finished which is a bedroom and bath). 2nd unit has 2 bedrooms, 2 baths. Also, two charming cottages: The first cottage offers 2 bedrooms & 1 bath. The 2nd cottage offers 1 bedroom 1 bath. The roof on all were done within the last 5 years. As well as appliance, updated kitchen, flooring, and electrical upgrades in some of the units. There is also a 2-car detached garage w/ loft area & an additional 1.25-acre BUILDABLE lot on its own section block and lot (Town verbally approved this lot for another 2-family home) also bringing it to a little over 5 acres. A wonderful opportunity for all! Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:2 Car Detached,

33 Eden Road Unit #41, Cuddebackville

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