Wingdale Real Estate

Welcome to Wingdale, a charming hamlet nestled in the heart of Dutchess County, New York. This picturesque community is part of the Town of Dover and is renowned for its serene landscapes and friendly atmosphere. With a rich history dating back to the 19th century, Wingdale offers a unique blend of small-town charm and modern convenience.

Surrounded by the natural beauty of the Hudson Valley, Wingdale is a haven for outdoor enthusiasts. Residents and visitors alike can enjoy the stunning views and recreational activities that the nearby Appalachian Trail and local parks provide. Whether you're hiking, biking, or simply taking a leisurely stroll, the area’s lush greenery and tranquil environment offer a perfect escape from the hustle and bustle of city life.

Wingdale is also conveniently located near major highways, making it easy to access nearby towns and cities, including the vibrant communities of Poughkeepsie and Beacon. With a variety of shopping, dining, and entertainment options just a short drive away, you’ll never be far from what you need.

Families will appreciate the strong sense of community and the excellent school system that serves the area. Wingdale is a place where neighbors know each other, and community events bring residents together, fostering a warm and welcoming spirit.

Whether you’re looking to settle down in a peaceful environment or seeking a weekend retreat, Wingdale offers a perfect blend of rural charm and accessibility. Explore the possibilities of calling this delightful hamlet your home!

Newest Listings in Wingdale

$314,900

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

$450,000

3 Beds ⋅ 3 Baths ⋅ 1025570 MLS

Welcome to the sought-after Wood Winds subdivision in the heart of Wingdale! This beautifully maintained 3-bedroom, 3-full bath home offers over 1,700 square feet of comfortable living space. Luxury vinyl plank flooring flows throughout, while the spacious kitchen features stainless steel appliances, granite countertops, and abundant cabinet space. The dining room opens through sliding glass doors to your own backyard retreat, where a heated in ground pool creates the perfect setting for relaxing, entertaining, and making the most of summer. Large windows throughout the home fill the space with natural light. The primary suite features a private ensuite bath, while two additional generously sized bedrooms share a full hall bath. The finished lower level offers a spacious recreation room or flexible living area complete with a third full bath—ideal for a mother/daughter set up, family room, home office, gym, or guest space. Conveniently located just minutes from the Harlem Valley-Wingdale Metro-North station, Route 22, local shops and restaurants, the Appalachian Trail, Dover Stone Church, and numerous parks and recreational opportunities, this home offers the perfect balance of neighborhood living and everyday convenience. Community water and sewer!

6 Hemlock Lane, 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

$375,000

3 Beds ⋅ 1 Baths ⋅ 960070 MLS

Located on 1.54 acres of scenic land, this charming overbuilt home has a perfect blend of comfort, privacy, and natural beauty. Enjoy open field views across the street from your living room, creating a peaceful backdrop for everyday living and relaxing evenings. The home features a warm and inviting layout, in the living room and kitchen, walls are tongue and groove knotty pine from ceiling to floor, brick fireplace in living room will keep the house cozy day/night. Retro knotty-pine cabinets from Crown Kitchen Cabinet Corporation (Brooklyn, NY) with a Tracy spacious stainless steel sink. Park your car (electric garage door) and walk through basement to upstairs, basement also has Bilco doors. Potential for wine cellar in pantry/cold room, have a project you would like to work on.....additional heating is already in basement. There is a separate well that can be used for gardening. Each room has original cast iron baseboards, keeping house warm in winter months. Surrounded by open space and mature landscape (grape vine can be found in the backyard) the property provides ample room for outdoor enjoyment, gardening, or future expansion. Minutes from Wingdale Metro North Station. Whether you’re seeking a serene retreat or a place to call home year-round, this property delivers space, views, and timeless appeal in a picturesque setting.

113 Dog Tail Corners 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

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