228 Dog Tail Corners – Country Charm with Endless Potential. Welcome to this classic 1928 family home, brimming with country charm and timeless character. With hardwood floors, a welcoming living room, and a handy entryway mudroom, this home offers both comfort and functionality throughout. The kitchen is ready to be reimagined into your dream cooking and gathering space. The first-floor features two comfortable bedrooms and a full bath, while a full walk-up attic provides plenty of room for storage or future expansion. Recent updates include modernized windows for efficiency and a basement housing the oil tank and furnace, with Bilco doors offering easy access to the backyard. Outside, you’ll find a detached one-car garage complete with pull-down attic stairs and a workshop area—perfect for hobbies or extra storage. Enjoy relaxing on the front porch and rest easy with a whole-house Generac generator already in place. Set on nearly a full acre, there’s plenty of space to add a pool, garden, or design your ideal outdoor retreat. With 1,296 sq. ft. of living space, this home offers solid bones, enduring charm, and endless possibilities to make it your own.
Walking Distance to Metro North Railroad, here is your chance to own a charming 3-bedroom, 2-full bathroom mobile home in tight-knit Wingdale Village. The screened in front porch leads to an open concept living room/kitchen combo - perfect for entertaining! This move-in ready home is waiting for you!!
Set among the rolling hills of Wingdale, New York, near the Sherman, Connecticut border, 1 Hoyt Road offers the quiet beauty of country living and the artistry of a thoughtfully built home. Morning light filters through tall windows, gliding across hardwood floors on the main level and the wide-plank flooring above. Each window frames views of trees and sky, blending the indoors with the surrounding landscape. The farmhouse combines timeless warmth with subtle sophistication. A brick entryway sets the tone for craftsmanship that continues throughout. The kitchen pairs rustic charm with everyday function, featuring exposed brick accents, built-in cabinetry, and a butcher block island that invites gathering and morning coffee. A first-floor bedroom and full bath offer convenience, while the upper bedroom and bath provide a private retreat beneath gentle eaves. Across the lawn, a detached two-car garage leads to a stunning great room, originally designed as an artist’s studio. Sunlight pours through three walls of windows, highlighting cathedral ceilings with exposed beams, a brick fireplace framed in detailed millwork, and granite tile floors that shimmer in the changing light. Built-in bookcases define the entryway with quiet elegance, while a full bath designed for accessibility adds comfort and versatility. Above the garage lies a loft-like open area, unfinished yet full of character, ready to serve as generous storage or a blank canvas for the imagination. The property sits essentially on the Wingdale, NY/Sherman, CT border, an area known for its sweeping natural beauty and multiple protected lands. To the east lies the newly established Grape Hollow State Forest, preserving hundreds of acres of wilderness and ensuring that the surrounding landscape remains untouched. The Appalachian Trail winds nearby, and favorite local destinations such as Bulls Bridge, Candlewood Lake, and Squantz Pond offer endless opportunities for hiking, kayaking, and peaceful weekends by the water. Less than two hours from New York City and close to Metro-North, this home welcomes both full-time residents and weekend retreat seekers who value beauty, privacy, and connection to nature. 1 Hoyt Road is more than a home. It is a composition of light, craftsmanship, and calm, surrounded by land that will remain beautifully still.
Welcome to your private equestrian retreat, just 4 miles from the Harlem–Valley Wingdale Train Station, 4 miles to charming Kent, CT, a mile away to the Appalachian Trail & easy access to Route 7 & Route 22. Set on a secluded private road off Lake Ellis, this property offers both convenience & privacy. Equestrian amenities include a main barn with 6 (12x10) stalls w/ hay loft, heated wash stall, & tack room, plus a 3-stall shed row barn, four paddocks, & a fully fenced in 180’ x 90’ outdoor riding arena. A heated workshop w/ car lift, air compressor & ability to install work benches, along w/ a pristine 2-car garage featuring epoxy flooring, providing excellent space for projects. Above the garage, a private studio apartment w/ separate entrance is ideal for guests or extended family. Enjoy a peaceful retreat by the stream w/ fire pit & hammock, or unwind in the radiant-heated sunroom w/ exposed beams & natural light.
23 Clearview Rd, Wingdale, NY – Multi-Family Opportunity Two homes for the price of one! This unique multi-family property sits on a .38-acre lot and includes a detached two-car garage—perfect for extra storage or workshop space. The main home features a primary bedroom with an ensuite bath, plus two additional bedrooms, a spacious kitchen, and a comfortable living room. The second home offers flexible living or rental potential. Each home comes equipped with its own septic system, well, and dry well, making this an ideal setup for extended family or investment income. While the property does need some TLC, it offers incredible potential for the right buyer. Don’t miss your chance to bring your vision and make this fixer-upper shine! Schedule your appointment today! Being sold AS IS
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
RARE FIND !! FULLY DETACTED 3 BR / 1 BTH / SPLIT LEVEL SINGLE FAMILY HOUSE W UNFIN. BSMT & FULL REAR DECK W LARGE WRAP AROUND BACK YARD LOCATED IN THE HEART OF PEACE AND TRANQILITY OF WINGDALE.. Featurning 3 BR's + WALK IN LARGE PANTRY ( 1st Floor Walk In Bedroom) Living Room, Kitchen, Basement, Large Back & Side Yard. Septic Tank for plumbing and Underground Oil Tank For Heating (SELLER NOT BRINGING ABOVE GROUND). Neighboring Horse Ranch and Houstotanic River complete this Serene Home. Close To Shops, Eateries, Schools, Train and Highway. Home Is Being Sold IN "AS IS' Condition. Home Needs Rubish Removal, Cosmetic Reno and Lawn Care... LOW TAXES.. THIS IS THE ONE YOU HAV E BEEN WAITING FOR... Don't Let This One Get Away. Call Now!!
Experience the charm of this classic raised ranch, located in the suburban town of Wingdale, NY, within Dutchess County. This home offers 3 bedrooms and 2 full baths, including a private ensuite in the primary bedroom. The spacious kitchen flows into a separate dining and living room, with a fireplace, creating a warm and inviting atmosphere. Additionally, this home has a partially finished basement, which offers endless potential, with space for an additional bedroom, a half bath, and a large family room. Outside, the expansive backyard features an in-ground pool and a play area, perfect for entertaining or relaxing. Other highlights include an attached garage and a washer and dryer for added convenience.
Exceptional opportunity to acquire this contemporary masterpiece designed by renowned architect Allan Shope. Tucked away in the serene woods of Wingdale, this property spans 29.7 acres and boasts a substantial pond, once part of the historic Camp Sacajawea. The residence is positioned on a secluded, wooded parcel, offering breathtaking views of mountains and the tranquil pond—making it an ideal retreat or permanent abode. This distinctive copper-clad home comprises 2 bedrooms and 1 bath, showcasing meticulous craftsmanship with handcrafted Black Walnut woodwork imported from Thailand. As you step inside, the attention to detail is immediately evident, highlighted by floor-to-ceiling windows adorned with custom drapes, glass countertops, a gas fireplace, and radiant heated floors throughout. The kitchen is equipped with top-of-the-line Thermador appliances, ensuring a premium culinary experience. The home also features an automatic generator, providing peace of mind during power outages. Architectural excellence extends beyond the existing dwelling, with available plans for the construction of an additional larger home on the expansive property. Embrace the opportunity to own a unique piece of architectural history while enjoying the tranquility and natural beauty that surrounds this remarkable residence.
Located in the sought-after Country Mill Estates in Wingdale, New York, this impressive colonial-style home, proudly offered by the original owners, is a remarkable find in the community. The property boasts level, meticulously landscaped grounds adorned with various specimen plantings, creating a picturesque outdoor setting. The residence features four well-proportioned bedrooms and two and a half bathrooms, offering ample space for comfort and privacy. An unfinished basement presents additional square footage, ripe for customization to suit personal tastes or needs. The heart of the home, the kitchen, is equipped with high-end stainless steel appliances and elegant granite countertops, leading out to a tranquil back deck, perfect for relaxation or entertaining. The property is conveniently situated near the local train station, enhancing its appeal to commuters.

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Wingdale is located in New York. Wingdale, New York 12594has a population of 1,358. Wingdale 12594 is less family-centric than the surrounding county with 27.18% of the households containing married families with children. The county average for households married with children is 29.92%.
The median household income in Wingdale, New York 12594 is $48,790. The median household income for the surrounding county is $87,112 compared to the national median of $69,021. The median age of people living in Wingdale 12594 is 41.4 years.
The average high temperature in July is 83.2 degrees, with an average low temperature in January of 14.9 degrees. The average rainfall is approximately 47.5 inches per year, with 43.5 inches of snow per year.