85 houses for sale in Wingdale

FALL in Love- In every season this home doesn't disappoint. Set on 2.2 acres overlooking picturesque lawns and pastures at the end of a quiet road. Distinctive architecture, abundant natural light, and a strong connection to the outdoors define this home. Cathedral ceilings, large windows, sliders, skylights, and a semi-open floor plan create a light, spacious interior. The welcoming foyer opens to the vaulted family room, to the inviting living room to the right. French glass-paneled doors connect the foyer, living, and dining rooms, allowing the flow of natural light, creating a comfortable setting for everyday living and entertaining. Hardwood floors and two fireplaces add warmth, including a new wood-burning fireplace insert framed by a floor-to-ceiling brick surround. The home's silo-inspired design, with rounded walls in the stairways, creates a unique connection between levels. An open upper-level landing serves as a bridge between the primary suite and three additional bedrooms

Opportunity awaits with this authentic 1700s Colonial located in the picturesque Gaylordsville section of New Milford. Offering over 1,800 square feet with three bedrooms and two full baths, this historic home is ready for its next chapter. In need of renovation and updating throughout, the property provides a unique opportunity to restore a classic New England home while preserving its original character and charm. A large two-car garage offers substantial additional space above, providing even more flexibility and potential. With a generous footprint, traditional Colonial architecture, and plenty of room to reimagine, this is an ideal project for a buyer looking to bring their vision to life. A true fixer-upper with history, character, and tremendous potential

Custom Dream home that blends modern luxury, comfort and peaceful living. Nestled in a beautiful 18-hole golf course community, this stunning better than new home offers spacious open living, abundant natural light and thoughtfully designed details throughout. From the moment you enter you'll notice the airy layout, oversized windows, 10ft ceilings and seamless flow. The heart of the home features a beautifully appointed kitchen with generous workspace, custom cabinets and finishes with all high-end appliances. This home includes many upgraded systems including whole house generator, whole house water and air filtration systems, water softener and so much more. Upstairs has 4 spacious bedrooms with 3 large bathrooms and laundry room. Primary bedroom is absolute magic. with large balcony overlooking the course and pond. Massive bathroom suite with spa like details including jacuzzi tub and walk in rain shower with 3 shower heads! His and hers walk in closets with plenty of built ins. Ex

Tucked away on.28 acres with seasonal views of the Housatonic River, this eclectic 1920 cottage is full of character and potential. Featuring 2 bedrooms, hardwood floors, central air, and a cozy woodstove, the home offers a unique opportunity for buyers looking to restore and personalize a property with charm. The detached artist studio provides the perfect space for creative pursuits, while an additional detached shed offers extra storage. In need of updating and repairs, this one-of-a-kind property is ideal for those with vision who appreciate distinctive homes, a peaceful setting, and the chance to create something special

Welcome to this inviting 3-bedroom, 2-full-bath ranch situated on 4.84 private acres, offering plenty of space, privacy, and potential. Surrounded by mature trees and expansive open yard space, this property provides a peaceful setting with room to enjoy the outdoors. The home features convenient one-level living, a functional floor plan, and two full bathrooms. An expansive unfinished basement provides plenty of storage. Several major improvements have already been completed, including a new boiler, along with new roof and vinyl siding completed in 2022- giving the next owner added peace of mind

Stunning Riverfront Retreat offers serene water views and the luxury of fishing and kayaking right in your own backyard. Beautifully renovated three-bedroom home is complemented by a one-bedroom pool house that works perfectly as a guest cottage. True resort-style living. Open-concept living and dining areas are filled with natural light, featuring two sets of French doors that lead to a spacious deck—ideal for seamless indoor-outdoor entertaining. Expansive windows showcase picturesque views of the famous Duchess County Ten Mile River. Designer kitchen includes recessed lighting, stylish pendant accents, and stainless-steel appliances. Pamper yourself in a primary en-suite with vaulted ceilings, a generous closet and spa-like bathroom complete with Jacuzzi tub, separate tiled shower, double vanity and water closet. A second bedroom with its own en-suite bath provides comfort and privacy for guests. Walkout lower level offers exceptional versatility, featuring a large family room perfe

Set in the scenic Merryall countryside, this beautifully expanded Colonial offers a balance of generous gathering spaces, private retreats, and landscaped grounds, with the flexibility to accommodate changing needs. At the heart of the home, a custom kitchen showcases rich cherry cabinetry, a distinctive coffered ceiling, granite countertops, a large center island, and an adjoining dining area. A butler's pantry adds convenience and storage, while wide openings create a natural flow between the kitchen and surrounding living spaces.The main level offers an appealing collection of rooms, including a formal dining room, inviting den with pellet stove and custom built-ins, dedicated office, and a bright four-season sunroom overlooking the landscaped grounds. The versatile floor plan also offers the potential to create a first-floor bedroom, adding yet another dimension to the home's adaptability. Crown molding, hardwood flooring, and distinctive architectural details bring warmth and char

Experience the ease of single-level living in this well-maintained 3-bedroom, 2-bath ranch. The inviting covered front porch and fresh curb appeal lead into an open, light-filled main floor with hardwood flooring throughout the living areas. The updated kitchen offers maple cabinetry, granite countertops, stainless appliances, a seating island, and glass subway tile backsplash, flowing into the dining area and a spacious living room with fireplace. Travertine and marble tiles in the bathrooms add an elevated touch, while a full attic provides extra storage potential. A second large living area offers flexible space, and the dedicated laundry room adds everyday convenience. Three bedrooms and two bathrooms (including a walk-in shower) complete the main level, with French doors opening to the fenced backyard that includes mature fruit trees. A large unfinished basement and full attic offers substantial storage potential. Set in the Town of Beekman (Poughquag area) of the Hudson Valley, t

Multiple Offers Received. Highest and Best by 1pm Monday 10/12. Attention investors, builders, and contractors! Unlock the incredible potential of this 4-bedroom ranch situated on over a full acre just outside the Village of Pawling. The property features a permitted mother-daughter setup, a spacious unfinished basement ready for expansion, and a large two-car garage. Recent updates include a newer roof, a fresh driveway, and a water heater. Ideally positioned just moments from I-84, Route 22, the Pawling Train Station, and the village's vibrant shops and restaurants. This home is offered strictly as-is

Welcome to 55 Beach Road in Poughquag, NY! Situated on approximately 1.14 acres with beautiful mountain views, this spacious center hall colonial offers 4 bedrooms, 2.5 bathrooms, and approximately 2,144 square feet of living space. Lovingly maintained by its original owners since 1999, this home reflects years of pride in ownership and exceptional care. Step inside to a welcoming two-story entryway with vaulted ceilings, a spacious and inviting layout, and plenty of natural light throughout. The home features a beautiful kitchen with granite countertops and stainless steel appliances, a cozy sunken family room with a wood-burning fireplace, and recently remodeled bathrooms. Additional features include a charming covered front porch, an attached two-car garage, and a full unfinished basement offering ample storage and potential for additional living space. Several major updates have already been completed, including a new boiler in 2023, central air conditioning approximately 5 years o

Expansive Colonial on 1.3 Private Acres Featuring Two Primary Suites, Heated Pool & Three-Car Garage! Nestled on beautiful private property, this impressive Colonial offers exceptional space, comfort, and versatility, surrounded by expansive front and rear lawns. A spacious three-car garage with additional storage adds to the home's many desirable features. Step inside the welcoming formal entry foyer and discover a thoughtfully designed layout ideal for everyday living and entertaining. The main level features an elegant formal dining room accented by a tray ceiling and recessed lighting, a generously sized first-floor primary bedroom suite, and an open-concept kitchen with direct access to an expansive deck. A comfortable family room, powder room, laundry room, and convenient garage access complete the first floor. An elegant staircase leads to the second level, where you'll find a second spacious primary bedroom suite, a versatile room ideal for a home office, library, or nursery, t

Morning coffee on the deck, birds singing, and deer wandering through the yard. At 84 Stowe Drive, this is how your day can begin. Set on 1.2 acres along a quiet street nestled in a mountain valley, this four-bedroom, two-and-a-half-bath home offers year-round mountain views and space to slow down and enjoy your surroundings. Step into the foyer and your eye travels straight through to the backyard, a glimpse of the setting that makes this home special. Natural light pours through the many windows, keeping the outdoors part of everyday life. In the kitchen, wood cabinetry, granite countertops, wine storage and an island with seating for four create a welcoming place to gather. The open flow connects the kitchen with the dining room and family room, while access to the deck makes taking dinner outside an easy decision. When autumn brings crisp air and changing leaves, settle into the family room beside the wood-burning fireplace and look out over the property and mountains. A separate f

Welcome to Quaker Hill Estate, a circa 1800 former dairy barn on 5.4 private acres on Quaker Hill, one of Pawling's most coveted areas. Horse and sheep farms and hiking trails surround the hill, yet New York City is about 90 minutes away. Set at the end of a long drive off a quiet, well-maintained county road, the post-and-beam barn was converted into a residence around 1980 and appeared on the cover of Country Living magazine a few years later. Today it offers four bedrooms, three and a half baths, and 3,660 square feet across three levels, framed by hand-hewn timbers and wide pine floors. A two-story masonry fireplace anchors the great room, and a separate-entry guest wing, a gunite pool, and long meadow views round out the property. The barn has a rich history; it was part of the Taber farm on Quaker Hill, purchased in 1760 by Thomas Taber of Dartmouth, Massachusetts, and held by his descendants for nearly two centuries. The conversion preserved the scale and craftsmanship of the or

Charming ranch nestled on a generous. 57-acre property in Pawling. Offering approximately 832 square feet of above-grade living space, this 2-bedroom, 1-bath home features a comfortable and functional layout with the primary living areas conveniently located on one level. Access to the main living area includes approximately 10 exterior steps. Inside, hardwood flooring and abundant natural light create a warm and inviting atmosphere. A deck extends the living space outdoors and provides a peaceful setting to enjoy the surrounding wooded landscape. The partial unfinished basement/garage offers additional storage, utility space, and flexibility. Set on a spacious lot with a tranquil natural backdrop, this inviting home offers a manageable footprint, valuable storage, and outdoor space with the opportunity to make it your own. Located in the scenic Hudson Valley, Pawling is known for its charming village atmosphere and access to an abundance of outdoor recreation, including the Appalachia

Welcome to your own little piece of heaven in sought after pawling ny. Property has two separate lots with a total of 23.50 acres and has outstanding outstanding mountain views. Owner has not tried to subdivide, however there are two wells on property. There is a newly constructed deck off the kitchen. Living room has a pellet stove which was installed in 2020 and keeps the whole house warm and cozy! Home has an unfinished basement with recent blown in insulation installed. Home was renovated in 2019 which includes a new furnace. If you love nature, this is the place to be, you will not be disappointed, come take a look

A European Inspired Oasis in Dover Plains! This meticulously cared for custom built home is being offered by the original owners for the first time. The impressive front entrance is where the grace and style begins. This 2,409 square foot home has too many custom features to list-making it a MUST SEE! In the primary residence you will find a primary bedroom, 2 additional bedroom, 2 full baths, one with a marble tile shower and floor, updated appliances, recessed lighting. The dining room has glass doors to the expansive, European baluster railed, veranda with breathtaking views overlooking the property, river and distant mountains. The lower level includes a legal 1 bedroom, 1 bath accessory apartment with living room. Perfect for multigenerational living. A one room studio is also on the lower level. A great space for an artist studio or overnight guests. Both lower level spaces open to the grand stone patios with fountain surrounded by stone walls. Sited on over 2 acres of lush garde

Classic 4-Bedroom Colonial in the desirable Cameo Farm neighborhood. Set on a spacious, nearly acre lot, this home offers a bright, traditional layout with a functional flow from the spacious kitchen open to the cozy family room to the formal living, and dining areas. The main level is completed by convenient laundry and access to the 2 car garage. Upstairs, the vaulted primary suite offers a private retreat with two large closets and an en-suite bathroom, accompanied by three additional generous bedrooms and a hall bath. Outdoor living is a highlight, featuring a welcoming front porch and a large back deck overlooking the sprawling, private backyard with endless potential for your personal vision. This home offers a newer roof and furnace. Fantastic opportunity for the next owner to move in and add their personal touches. Enjoy quiet, tree-lined suburban living with unmatched everyday convenience. Commuters will appreciate the effortless access to Route 55 and the Taconic Parkway, whi

Privately set on 3.6 acres in Dover Plains, this spacious Colonial offers a unique and versatile layout with plenty of room to make it your own. Built in 2005, the home features 3 legal bedrooms, 3 full bathrooms and 1 half bathroom, with a standout feature being the legal accessory apartment complete with its own private entrance. The main living space offers a traditional Colonial layout with generous room throughout. Upstairs, the primary bedroom features a walk-in closet and private full bathroom, along with 2 additional bedrooms, a hallway full bathroom and a versatile bonus room ideal for a home office or flex space. The legal accessory apartment adds another level of versatility, featuring its own kitchen, living room, bedroom, full bathroom and separate entrance. Whether used for extended household living, guests or simply additional private space, it is a valuable feature that can be difficult to find. Outside, the 3.6-acre setting provides a sense of privacy and separation wi

Versatility, comfort, and an exceptional lifestyle come together in this charming Cape Cod-style home in Pawling Lake Estates, a picturesque lake community nestled atop West Mountain and bordering West Mountain State Forest. Offering 2,188 SF across the first two levels, plus an additional 320 SF finished recreation room in the basement, this thoughtfully designed home features three bedrooms, four full baths, and a flexible floor plan that adapts to your lifestyle. A two-story entry sets the stage for the inviting interior. The main level offers a living room warmed by a pellet stove, a country kitchen with pantry, laundry closet, and dining area with sliding glass doors opening to the expansive walk-off rear deck. A den provides endless possibilities as a family room, home office, formal dining room, or could even be incorporated into the adjacent living room to create a more open layout. Completing the first floor is a full hall bath and a private ensuite bedroom featuring its own b

Experience refined privacy in this light-filled 3-bedroom, 3-bath Hi-Ranch in a peaceful country setting. This property sits on a beautiful and level 3.19 acres in Pawling, NY, framed by evergreen trees and mature landscaping reflecting a gardener's legacy. The interior reflects a loving family’s touch; it is functional and comfortable, with great potential for modern updates. Its standout location offers easy access to Metro-North, the Taconic State Parkway, NYS Route 22, Route 55, I-84 and I-684 within a short drive. A long driveway, wrought-iron entry gates, a 2-car garage, and a fenced yard enhance privacy. With some work, this home can shine and fully capitalize on its exceptional setting and Pawling location. The main living area features vaulted ceilings, a living room with a pellet stove, an eat-in kitchen with a convenient laundry area leading to a dining room with sliders to a screened-in porch and large deck. There is also a primary bedroom with a full bath and double closet

Welcome home to 36 bronson road! Set on 1.6 picturesque acres in the highly sought-after Arlington School District, this fully renovated raised ranch offers the perfect blend of timeless style and modern comfort. Featuring 3 bedrooms, 2 full bathrooms, a brand-new high-efficiency heat pump system with central air, and nearly 1,900 square feet of beautifully updated living space, this move-in-ready home has been thoughtfully redesigned from top to bottom. The bright, open-concept main level showcases gleaming new hardwood floors, recessed lighting, and abundant natural light. The stunning chef's kitchen features crisp white shaker cabinetry, gorgeous stone countertops, stainless steel appliances, breakfast bar seating, and flows seamlessly into the dining area with sliding glass doors leading to the oversized rear deck, creating the perfect space for indoor and outdoor entertaining. The spacious primary suite offers a beautifully renovated en-suite bathroom with a custom tiled walk-in s

Set on beautiful grounds next to the Akin Free Library, this one-of-a-kind Colonial offers a rare combination of privacy and charm. The property, including the adjacent BOHA 4 bed parcel, spans 7.48 acres of old-growth trees, a creek, and an open field overlooking Kirby Hill Farm. A gated, tree-lined driveway leads to a home that blends functional living with the timeless character of Quaker Hill

Don't miss this newly listed one of a kind home nestled on 8.44 private acres with views so outstanding they could take your breath away. This 5700 plus sq. Ft. home w/6 generous sized Brs, 5.5 baths is only the start. Its primary Br. 25X18 w/Fp, Lg. Tiled bath w/jacuzzi & those mountain top views again then to a spacious walk/in closet. There are an additional 4 more bedrooms all with oak floors on this level. (2nd Floor) The main level all with oak floors. (Exception tile foyer) features a lg. Country equipped kitchen w/all appliances, center island, granite counters, dinning area and more abutting 23' a family room a w/10 ft' ceiling & gas Fp

Welcome home to this LIKE NEW CONSTRUCTION—without the wait! This stunning, completely top to bottom renovated 3-bedroom (lives like a 4), 2.5-bath, 3,600+ sq. Ft. Farmhouse Colonial sits on over an acre in the heart of Beekman, within the Arlington School District. Step onto the expansive Trex rocking-chair front porch, the perfect place to enjoy morning coffee or evening cocktails while taking in breathtaking mountain views. Inside, the elegant two-story foyer showcases a Hudson Valley Lighting chandelier and oversized windows that flood the home with natural light. Every detail radiates charm and sophistication. Gorgeous new oak floors flow throughout, leading into a bright, spacious living room featuring a cozy fireplace with a barnwood mantle—ideal for both relaxation and entertaining. The open layout continues into a breakfast nook with a striking floor-to-ceiling brick accent, seamlessly connecting to the custom kitchen of your dreams. This chef’s kitchen is meticulously designe

Custom Dream home that blends modern luxury, comfort and peaceful living. Nestled in a beautiful 18-hole golf course community, this stunning better than new home offers spacious open living, abundant natural light and thoughtfully designed details throughout. From the moment you enter you'll notice the airy layout, oversized windows, 10ft ceilings and seamless flow. The heart of the home features a beautifully appointed kitchen with generous workspace, custom cabinets and finishes with all high-end appliances. This home includes many upgraded systems including whole house generator, whole house water and air filtration systems, water softener and so much more. Upstairs has 4 spacious bedrooms with 3 large bathrooms and laundry room. Primary bedroom is absolute magic. with large balcony overlooking the course and pond. Massive bathroom suite with spa like details including jacuzzi tub and walk in rain shower with 3 shower heads! His and hers walk in closets with plenty of built ins. Ex