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Wingdale, NY Homes for Sale with Acreage

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  • /34

    $3,200,000

    $700K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,933 Sq Ft

    6 Hoyt Rd, Sherman, CT 06784

    Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a

    Agent Photo

    Eric Bergers

    William Raveis Real Estate

    6 Hoyt Rd, Sherman, CT 06784
  • /40

    $585,000

    • 3 Beds
    • 2.5 Baths
    • 2,122 Sq Ft

    36 Hillside Ave, Wingdale, NY 12594

    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

    Agent Photo

    Jackie Calhoun

    Coldwell Banker Realty

    36 Hillside Ave, Wingdale, NY 12594
  • /38

    $899,000

    • 4 Beds
    • 3.5 Baths
    • 3,434 Sq Ft

    128 Old Pawling Rd, Pawling, NY 12564

    Beautifully situated on 5.5 private acres, this impressive home offers a gated entrance and a long private driveway leading to breathtaking mountain views and a peaceful setting. Relax on the charming rocking-chair front porch and enjoy the serenity of the surrounding landscaped front lawn. Step inside to a dramatic two-story foyer and an abundance of natural light. The spacious kitchen features

    Agent Photo

    Teddie Leonaggeo

    McGrath Realty Inc

    128 Old Pawling Rd, Pawling, NY 12564
  • /46

    $795,000

    Open Sun 1PM - 3PM $20K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,234 Sq Ft

    360 Old State Route 22, Dover Plains, NY 12522

    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

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    360 Old State Route 22, Dover Plains, NY 12522
  • /16

    $895,000

    • 4 Beds
    • 2 Baths
    • 2,160 Sq Ft

    2536 Wingdale Mtn Rd, Poughquag, NY 12570

    Horse Property with Indoor Arena & Loads of PotentialBring your horses home to this small horse property featuring a 4-bedroom house with an indoor riding arena and private wooded trails on the property. Located only 2 miles from Tymor Park for an abundance of additional riding opportunities and trails. The property offers a practical setup for horse owners looking for the convenience of

    Agent Photo

    Diana Murphy

    HomeSmart Homes & Estates

    2536 Wingdale Mtn Rd, Poughquag, NY 12570
  • /17

    $314,900

    • 2 Beds
    • 1 Bath
    • 1,378 Sq Ft

    122 Weil Rd, Wingdale, NY 12594

    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

    Brian Smith River Realty Services, Inc.

    122 Weil Rd, Wingdale, NY 12594
  • /43

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,686 Sq Ft

    73 Lake Ellis Rd, Wingdale, NY 12594

    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

    Lonnie Lum Coldwell Banker Realty

    73 Lake Ellis Rd, Wingdale, NY 12594
  • /2

    $1,195,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 3,675 Sq Ft

    60 Long River Rd, Sherman, CT 06784

    River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have

    Joe Chemero Coldwell Banker Realty

    60 Long River Rd, Sherman, CT 06784
  • /45

    $1,250,000

    $49K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,770 Sq Ft

    110 Hillside Ave, Wingdale, NY 12594

    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

    Janet Myer Houlihan Lawrence Inc.

    110 Hillside Ave, Wingdale, NY 12594
  • /5

    $649,000

    • 3 Beds
    • 3 Baths
    • 2,000 Sq Ft

    149 Johnson Rd, Wingdale, NY 12594

    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

    Bliss Voutsinas Hillside Realty & Development

    149 Johnson Rd, Wingdale, NY 12594
  • /11

    $199,000

    $40K PRICE DROP
    • Land
    • 2.4 Acres
    • $82,917 per Acre

    0 Route 22 Unit KEY976107, Dover, NY 12594

    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.

    Lisa Liffland McGrath Realty Inc

    0 Route 22 Unit KEY976107, Dover, NY 12594
  • /40

    $2,395,000

    $100K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 6,368 Sq Ft

    2 Pond View Ln, Sherman, CT 06784

    Custom Dream home that blends modern luxury, comfort and peaceful living. Nestled in a beautiful 18-hole golf course community, this stunning newer-construction residence 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

    Joe Chemero Coldwell Banker Realty

    2 Pond View Ln, Sherman, CT 06784
  • /28

    $799,000

    • 3 Beds
    • 3.5 Baths
    • 4,208 Sq Ft

    150 Deer Hollow Rd, Poughquag, NY 12570

    A Private Hudson Valley Retreat on 12+ AcresWelcome to 150 Deer Hollow Road, a truly special private retreat set amid more than 12 acres of picturesque Hudson Valley countryside in the Town of Union Vale. Surrounded by mature trees, open space and the peaceful beauty of the landscape, this exceptional property offers the rare combination of privacy, space and versatility—while remaining

    Marlena Mucci The Select Team, LLC

    150 Deer Hollow Rd, Poughquag, NY 12570
  • /15

    $349,000

    • Land
    • 9.61 Acres
    • $36,316 per Acre

    4,10,12 River Oaks Ln, Sherman, CT 06784

    Exceptional opportunity to purchase a three-lot package totaling 9.62 acres in the gated community of The Club at River Oaks in Sherman, CT. The offering includes 4 River Oaks Lane (3.12 acres), 10 River Oaks Lane (3.07 acres), and 12 River Oaks Lane (3.42 acres), all bordering the 9th green of the community's 18-hole, par-70 golf course. Lot 12 includes a 4-bedroom septic design and offers

    David Landau RE/MAX Right Choice

    4,10,12 River Oaks Ln, Sherman, CT 06784
  • /2

    $599,000

    $200K PRICE INCREASE
    • Land
    • 8 Acres
    • $74,875 per Acre

    0 Route 22 Unit ONEH6222664, Dover, NY 12594

    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

    Lydia Nioras Commerce Properties

    0 Route 22 Unit ONEH6222664, Dover, NY 12594
  • /11

    $190,000

    • Land
    • 1.66 Acres
    • $114,458 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /11

    $205,000

    • Land
    • 2.5 Acres
    • $82,000 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /11

    $195,000

    • Land
    • 1.85 Acres
    • $105,405 per Acre

    0 New York 22, Dover Plains, NY 12522

    Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /26

    $595,000

    $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,409 Sq Ft

    20 Craig Ln, Dover Plains, NY 12522

    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

    CAROL LYNNE PENTA K. Fortuna Realty, Inc.

    20 Craig Ln, Dover Plains, NY 12522
  • /25

    $299,000

    • Land
    • 5.46 Acres
    • $54,762 per Acre

    41 Long River Rd, Sherman, CT 06784

    This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities,

    Donna Kennedy Compass Connecticut, LLC

    41 Long River Rd, Sherman, CT 06784
  • /5

    $100,000

    • Land
    • 1 Acre
    • $100,000 per Acre

    149 Johnson Rd, Wingdale, NY 12594

    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

    Bliss Voutsinas Hillside Realty & Development

    149 Johnson Rd, Wingdale, NY 12594
  • /35

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 2,222 Sq Ft

    125 Sheldon Rd, Wingdale, NY 12594

    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

    Lisa Liffland McGrath Realty Inc

    125 Sheldon Rd, Wingdale, NY 12594
  • /2

    $110,000

    • Land
    • 3 Acres
    • $36,667 per Acre

    7 Brookview Rd, Dover Plains, NY 12522

    Private country setting with abundant wildlife to enjoy. Ideally located a short driving distance from Millbrook to the West, Amenia to the North, on the East by Kent, CT, and the South by Pawling. BOHA until 2029, no fill required for a 3 or 4 bedroom home. Close to railroad for NYC commuters. Specific area is known as Ridgebrook Country Estates. Must see to appreciate!

    Robert D Ferris R. Ferris Real Estate, LLC

    7 Brookview Rd, Dover Plains, NY 12522
  • /24

    $1,999,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 5,900 Sq Ft

    41 Long River Lot 30 Rd, Sherman, CT 06784

    Craft your dream home from the ground up with this luxury built-to-suit offering set on a sprawling 5.46 acre lot on Long River Rd in River Oaks Country Club, a private gated community in Sherman, CT. This 4 bd / 3.5 bath / 3500 SF open-concept residence with main level primary suite seamlessly connects a chef's kitchen (w/ pantry) to an elegant dining area and a living room w/ cozy fireplace.

    Donna Kennedy Compass Connecticut, LLC

    41 Long River Lot 30 Rd, Sherman, CT 06784
  • /7

    $40,000

    $10K PRICE DROP
    • Land
    • 2.7 Acres
    • $14,815 per Acre

    0 Old Pawling Rd Unit KEY1020201, Dover, NY 12564

    An expansive 2.7-acre parcel of land nestled serenely along a picturesque country road, offering a charming and tranquil setting.The land goes downhill from the road to a designated wetland and then rises quite sharply through mature woodland. This idyllic property is conveniently situated near the highly accessible and major thoroughfare, Route 22, ensuring ease of travel and connectivity to

    Michael Martell eXp Realty

    0 Old Pawling Rd Unit KEY1020201, Dover, NY 12564
  • /2

    $97,000

    • Land
    • 3.3 Acres
    • $29,394 per Acre

    488 Pleasant Ridge Rd, Poughquag, NY 12570

    Beautiful 3+ acres wooded lot in the Town of Union Vale. Convenient to TSP, Route 55 and Hudson River. BOHA.

    Graziano Tassone Tassone Realty Corp.

    488 Pleasant Ridge Rd, Poughquag, NY 12570
  • /46

    $2,475,000

    • 4 Beds
    • 4.5 Baths
    • 2,412 Sq Ft

    56 Northrup Rd, Dover Plains, NY 12522

    At the very end of a quiet country road, you'll find 56 Northrup — a stunning, architect-designed retreat blending 19th-century farmhouse charm with thoughtful, award-winning modern design. Originally built in 1870 and reimagined by NYC architects Neumann & Rudy, this 33-acre property includes a restored main house, a sleek single-story primary suite addition, and expansive grounds featuring a

    Adam Hade Compass Greater NY, LLC

    56 Northrup Rd, Dover Plains, NY 12522
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