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$680,000
3 Beds ⋅ 2 Baths ⋅ 1047398 MLS
A little bit of magic lives at 16 Carlson Road. Built in 1850, this charming home feels like something out of a fairytale, surrounded by nearly nine acres of mature gardens and old-growth trees. Walking paths wind through the acreage, and the beautifully established landscape gives the property a character all its own. While the history of the home is felt throughout, recent thoughtful updates have been made, creating comfortable, beautifully considered spaces while preserving the character that makes it so special. Inside, natural light fills the rooms, with skylights overhead and windows framing views of the surrounding gardens. The main level unfolds through a series of inviting spaces, including a sunroom, formal and informal dining rooms, and a living room anchored by a wood-burning stove. A deck just off the dining room sits beneath an extraordinary mature hydrangea, creating a natural canopy for long summer lunches and dinners outside. The primary suite is on the main level, with radiant floor heating extending through both the bedroom and spacious bathroom. Two generously sized walk-in closets provide ample storage, while French doors open directly onto a bluestone patio. Just off the bedroom, a charming home office with built-ins makes working from home feel decidedly less like work. Upstairs, two sun-filled bedrooms share a bathroom with a clawfoot tub, with ample storage throughout. The property also includes two outbuildings: a one-car garage and a separate garage/workshop with a loft above, ready for projects, studio space, or whatever creative pursuits the property inspires. Just five minutes from the Harlem Valley Metro-North station, the property offers easy access to New York City, with Grand Central just over two hours away. Wassaic Metro-North is 20 minutes away, with Kent, Connecticut just 10 minutes away and Millbrook approximately 25 minutes. It’s a rare kind of Hudson Valley retreat, where beautiful gardens, a sense of history, and just a little everyday magic come together.

16 Carlson Road, Wingdale
$499,000
3 Beds ⋅ 3 Baths ⋅ 1043677 MLS
Tastefully updated 3 bedroom, 2.5 bathroom raised ranch with incredible backyard oasis. Ideal for relaxing or entertaining, this home includes an updated kitchen w/quartz counters & stainless appliances, large living room loaded with natural light and dining room with sliding glass door leading to deck and incredible backyard complete with heated pool & massive patio. Primary bedroom w/ensuite bathroom plus two additional bedrooms and full bathroom on main level. Lower level includes huge family room, laundry room, half bathroom and office/den. New flooring & fresh paint throughout. One car garage for storage. Enjoy the conveniences of 200 amp electric plus a 17kw standby generator. Easy access to local amenities, Wassaic train station, Route 22 and Route 55. Attractively low taxes.

45 Nicole Lane, Wingdale
$585,000
3 Beds ⋅ 3 Baths ⋅ 1036661 MLS
Welcome to this well-maintained 3-bedroom, 2.5-bath Colonial, beautifully situated on over 2 private acres near the Pawling border. Surrounded by mature trees, established gardens, and fruit trees, this property offers a peaceful and picturesque setting with plenty of room to relax, garden, and entertain. The main level features a spacious kitchen, attractive parquet wood flooring throughout much of the first floor, and a cozy wood-burning stove. A standout feature is the first-floor full bath with a Jacuzzi tub and separate shower, along with a convenient powder room for guests. Upstairs, you’ll find three spacious bedrooms and an additional full bath, offering a comfortable and functional layout. The huge unfinished basement is filled with possibilities, featuring large windows and direct egress to the backyard, making it ideal for future recreational, fitness, office, or additional living space. Additional highlights include central air conditioning, a two-car garage, generator hookup, and a water catchment system. With its generous acreage, privacy, mature landscaping, fruit trees, and convenient location near the Pawling border, this inviting Colonial offers space, comfort, thoughtful features, and wonderful potential both inside and out.

36 Hillside Avenue, Wingdale
$575,000
4 Beds ⋅ 3 Baths ⋅ 1036001 MLS
Great Colonial home features a wonderful, 40 ft covered front porch, where you can relax and enjoy the lovely view! Spacious Foyer with closet, large, very nice Living Rm with popular LVP flooring, Family Rm with Fireplace & door to deck. The Kitchen features a spacious Dining Area, an Island with a granite top, stainless appliances, propane range. There is also a formal Dining Rm, currently used as an office. Also on the first floor is a pretty half bath and a laundry area. Upstairs, you will find 4 Bedrooms, one of which is the Primary suite. Hall full bath offers a great vanity with a granite top. All bedrooms have ceiling fans! Large 21x23 Two-Car Garage features a very high ceiling. Basement is 24x40. All dimensions are approximate. Siding, Windows, and Roof 2019. Not far from the home are the Dover Schools, Town Library, Dykeman’s Farm and farm stand. Boyce Park in Wingdale offers a playground, baseball field, basketball court and a pavilion. *Metro-North has two nearby train stations, Wingdale and Pawling. Nature lovers will enjoy hiking the Appalachian Trail and exploring the beautiful area of well-known Stone Church in Dover. Short drive to Pawling, where you will find quaint shops, restaurants & pubs, grocery store, gym, medical offices, more.

125 Sheldon Road, Wingdale
$299,900
2 Beds ⋅ 1 Baths ⋅ 1028548 MLS
Two bedroom, one bath cottage on an amazing pastoral setting on a 6.16 acre lot in the town of Dover. Great place for a weekend retreat or year-round home. Bring your imagination and renovate this home to your needs. Amazing setting! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with rehab loan financing must be accompanied by a pre-qualification letter; cash offers with proof of funds. Please see agent remarks for access, showing instructions and offer presentation remarks.

122 Weil Road, Wingdale
$649,000
3 Beds ⋅ 3 Baths ⋅ 1025768 MLS
New construction home to be built ! This raised ranch home features 3 bedrooms and 3 full bathrooms and 2 car garage. The open floor plan connects the kitchen, dining room and living room. The primary bedroom with ensuite bathroom features a spa like walk in shower. The plans are approved and ready to build, don't miss the opportunity to customize this home

149 Johnson Road, Wingdale
$100,000
1025750 MLS
Land for sale with board of health approval- Approved plans for a 3 bedroom, 3 bathroom raised ranch home. Well is drilled, land is ready to start building your dream home today

149 Johnson Road, Wingdale
$899,000
3 Beds ⋅ 2 Baths ⋅ 1015591 MLS
A rare opportunity for the dedicated equestrian, this beautiful gentleman’s farm is set on nearly 9 acres of gently rolling countryside, offering the ideal balance of privacy, usability and convenience. Whether you’re an active competitor, trail rider or simply seeking a peaceful horse property, this special offering provides the setting to pursue your passion. Perfect as a full-time residence or idyllic weekend getaway, the property offers a welcome escape from city life while remaining easily accessible. Horse show enthusiasts will appreciate the convenient proximity to many of the regions’ premier equestrian venues, training facilities and riding opportunities. The nearly 9 acres parcel provides ample space for paddocks, turnout and a sand riding ring. Beyond its equestrian appeal, the property also caters to the automotive enthusiasts. A spacious garage equipped with a vehicle lift provides the ideal place to work on your projects. Adding to the property’s versatility is a legal accessory apartment, perfect for extended family, guests, a caretaker or trainer. Spend your days riding, relaxing and enjoying the beauty of the surrounding countryside, then take advantage of the property’s convenient access to the Harlem Vally-Wingdale train station for seamless travel to and from NYC. Combining the charm for a gentleman’s farm with the lifestyle and conveniences sought by today’s horse owners, car enthusiasts and weekend retreat seekers, this exceptional property is a place where passions can flourish and country living is enjoyed to its fullest.

73 Lake Ellis Road, Wingdale
$1,250,000
4 Beds ⋅ 4 Baths ⋅ 1001139 MLS
Set on four beautiful acres with sweeping long range views of the foothills and ridges around Litchfield Hills and The Taconic Mountains, this thoughtfully designed contemporary home offers exceptional privacy, tranquility, and quality throughout. Built by the owners for their own use, no expense was spared, with high end materials and meticulous attention to detail. Incredible natural light fills the home, enhanced by oversized windows that capture the surrounding landscape and bring the outdoors in. A gracious front entry welcomes you into the formal living and dining rooms. The living room features a wood-burning fireplace and beautiful views overlooking the backyard and surrounding landscape. The spacious kitchen is designed for both everyday living and entertaining, featuring a large center island, pantry, and sunny eat-in area. The kitchen opens seamlessly to the family room, where oversized windows frame peaceful nature views and fill the space with light. Both rooms open onto a tiered deck overlooking the gardens and distant mountain views, an ideal setting for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. The expansive primary suite offers a true retreat with a spacious en-suite bath, walk-in closet, and separate sitting area. A large laundry room is conveniently located off the kitchen and two car garage, while a half bathroom and private office complete the main level. The second floor includes three additional bedrooms, including one with its own en-suite bath, while the remaining two bedrooms share a full bathroom. The lower level offers tremendous flexibility and is currently used as workspace. With large windows and direct exterior access, it presents endless possibilities for future finishing as recreation space, studio, gym, media room, or guest area. A newly built two-story barn is a standout addition to the property, featuring durable Hardie Board siding and superior construction quality. Beautifully landscaped and private, this property offers a rare combination of craftsmanship, comfort, and natural beauty. This property is located in an area of the Hudson Valley known for its scenic beauty, and farm to table restaurants. Less than ten minutes to Metro North Railroad.

110 Hillside Avenue, Wingdale
$199,000
976107 MLS
Just north of the Town of Pawling border, you will find this 2.4 acre parcel. Convenient location is close to schools, town library, Thomas Boyce Park, Wingdale Metro-North train station. This is a residential parcel, zoned RU.

Route 22, Wingdale
$45,000
971928 MLS
This 0.64-acre parcel on Aldrich Road in Wingdale, NY is offered at $45,000. This property presents a unique opportunity for an investor or a visionary builder looking to create a custom residence in a quiet, rural setting. Property Highlights Acreage: 0.64 acres of land in a serene, off-the-beaten-path location. Price: Competitive entry-point pricing at $45,000, reflecting the current approval status. Status: The parcel is not currently Board of Health (BOH) approved. Buyers will need to conduct their own due diligence regarding well and septic requirements to secure future building permits. Privacy: Located on Aldrich Road, known for its peaceful atmosphere and proximity to natural landscapes. Local Amenities & Lifestyle Wingdale offers a perfect balance of country living and essential convenience: Commuter Friendly: Close to the Wingdale Metro-North station, providing a direct link for those traveling to New York City or lower Westchester. Outdoor Recreation: Enjoy easy access to the Appalachian Trail and nearby trout streams for hiking and fishing. Community: Residents describe the area as a tight-knit, friendly community that takes pride in local holiday traditions and a quiet environment. Schools: Served by the Dover Union Free School District, which locals highly value for its community-focused upbringing. This property is ideal for someone looking to secure a piece of the Hudson Valley at an affordable price and take the next steps toward development.

Aldrich Road, Wingdale
$1,290,000
933993 MLS
Discover an extraordinary turnkey opportunity to own a fully renovated, free-standing restaurant in the heart of Dutchess County, perfectly positioned for success in the thriving Hudson Valley dining scene. This impressive 3,236-square-foot single-level building has been meticulously transformed, offering seating for 100 guests across multiple inviting dining spaces, plus a stylish bar area and additional outdoor seating beneath a spacious covered patio for outdoor dining spring, summer and fall. Step through the welcoming double-door entry into a bright and expansive main dining room, where guests are greeted by a sophisticated bar and direct access to the covered patio for seamless indoor-outdoor flow. A second generously sized dining room provides flexibility for larger parties, while an intimate private dining room sets the stage for memorable special events, celebrations, and catered affairs. A long hallway connects three well-appointed public restrooms and offers convenient secondary access to the patio. The kitchen is massive and awaits your customization, allowing the new owner to design the perfect layout for their culinary concept. The room is outfitted with a commercial ventilation system and plumbed for sinks along the walls. Supporting spaces include a dedicated staff bathroom, pantry, and mechanical rooms, all thoughtfully arranged for maximum efficiency. Below, a full basement houses brand-new multi-zoned HVAC systems, water filtration system, and offers abundant dry storage to keep operations running smoothly. Outside, multiple expansive parking lots provide ample spaces for patrons and staff, a rare and valuable asset that eliminates parking concerns. Location is everything, and this prime Wingdale address delivers unbeatable visibility and accessibility on well-traveled Old State Route 22, just seconds from Route 22 and moments from Route 55—the primary corridor connecting New York to the Connecticut border. Less than a mile away, the Wingdale Metro North train station offers effortless commutes to Manhattan, drawing city dwellers seeking weekend getaways and authentic Hudson Valley experiences. Surrounded by the charming towns of Dover, Pawling, Millbrook, Amenia, and Millerton to the north, south and west, and the picturesque Connecticut communities of New Milford, Kent, Gaylordsville, and Sherman to the east, the restaurant sits at the crossroads of a vibrant, affluent market eager for exceptional dining. Whether you envision an upscale farm-to-table destination, a lively craft-beer gastropub, or a sophisticated event venue, this move-in-ready property provides the canvas, infrastructure, and unbeatable location to bring your restaurant dreams to life. The potential of owner financing can make this a truly rare and compelling investment. Schedule your private tour today and step into a future filled with possibility.

34 Old State Route 22, Wingdale
$599,000
H6222664 MLS
Raw Land - Located on Route 22 in Wingdale/Dover Plains. Approximately 8 acres. The Town of Dover is progressing with a comprehensive rezoning initiative to allow multifamily dwellings to be built OR commercial use buildings IE shopping centers or other uses. Available is survey, and several documents limited topo, tax map, ariels etc. Proposal of a large box store drawings available but not approved. NO trespassing and all showings must have prior written approval to walk the property.

Route 22, Wingdale

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.