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Wingdale, NY Homes for Sale with Acreage

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  • /43

    $825,000

    • 4 Beds
    • 4.5 Baths
    • 2,234 Sq Ft

    360 Old State Route 22, Dover Plains, NY 12522

    A rare offering in today’s market - gorgeous River Front Home with calming water views and fishing every day right in your own back yard. Renovated and updated 3 bedroom home with a one bedroom pool house that doubles as a guest cottage. All the amenities you would expect in the best resort style property. Open concept Living and Dining area with 2 sets of French doors opening to an expansive

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    (845) 280-5286

    360 Old State Route 22, Dover Plains, NY 12522
  • /35

    $650,000

    • 4 Beds
    • 2.5 Baths
    • 3,446 Sq Ft

    786 N Clove Rd, Millbrook, NY 12545

    Escape the hustle and bustle of city life and discover true tranquility at this charming country home, nestled on 3 acres of picturesque, private land that abuts a creek with a built in stone grill. This property offers a unique lifestyle opportunity for those seeking serenity, space, and a connection with nature.The inviting home features a cozy, functional, and light-filled interior,

    Diana Wiemer Houlihan Lawrence Inc.

    786 N Clove Rd, Millbrook, NY 12545
  • /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
  • /31

    $1,395,000

    • 4 Beds
    • 3.5 Baths
    • 3,247 Sq Ft

    73 Long River Rd, Sherman, CT 06784

    This elegant four-bedroom home, built in 2021, is perfectly sited on 1.8 acres of professionally landscaped, private grounds. Designed for effortless single-level living, it features an open-concept layout with a chef's kitchen and center island, a welcoming living room with fireplace, and a sunlit dining area that all flows seamlessly to a covered porch with views toward the Housatonic River.

    Steve Pener William Pitt Sotheby's Int'l

    73 Long River Rd, Sherman, CT 06784
  • /4

    $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
  • /30

    $1,499,999

    • 2 Beds
    • 1 Bath
    • 1,600 Sq Ft

    165 Duell Hollow Rd, Wingdale, NY 12594

    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

    Bianca D'Alesandro Serhant LLC

    165 Duell Hollow Rd, Wingdale, NY 12594
  • /2

    $99,900

    • Land
    • 3.3 Acres
    • $30,273 per Acre

    Lot 7 Brookview Rd, Dover, NY 12522

    Located approximately 6.5 miles from the Village of Millbrook. Trains to New York City are available only 3.3 miles away at the Metro North Station in Dover Plains. Picturesque Stone Brook traverses the property. Ideal for your weekend or year-round dream home. Board of Health Approved and no fill required.

    Robert D Ferris R. Ferris Real Estate, LLC

    Lot 7 Brookview Rd, Dover, NY 12522
  • /2

    $599,000

    • 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
  • /10

    $1,200,000

    • Land
    • 51.38 Acres
    • $23,355 per Acre

    0 Brush Hill Rd Unit KEY935753, Union Vale, NY 12545

    A stunning 51+ acre parcel offering complete privacy and sweeping long views of the Clove Valley, this idyllic setting is the perfect canvas for your dream retreat. A beautiful blend of open meadow and wooded landscape, the land features both level and gently sloping terrain, highlighted by a seasonal stream and ample space to create your own trail system for recreation, exploration, or nature

    Byron Anderson Compass Greater NY, LLC

    0 Brush Hill Rd Unit KEY935753, Union Vale, NY 12545
  • /44

    $450,000

    • 2 Beds
    • 3 Baths
    • 1,939 Sq Ft

    1 Hoyt Rd, Wingdale, NY 12594

    A rare two-building property, 1 Hoyt Road pairs a classic farmhouse with a newer studio-style structure built in 2008, featuring a fireplace, full bath, and two-car garage. 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

    Stephanie Ruzzo RE/MAX Classic Realty

    1 Hoyt Rd, Wingdale, NY 12594
  • /23

    $499,000

    • 1 Bed
    • 1 Bath
    • 805 Sq Ft

    105 Sand Hill Rd, Dover Plains, NY 12522

    The Geosphere is a convergence of visionary design, tactical investment and natural sanctuary. Set on 7.18 secluded acres in the heart of Dover Plains, this fully legal, architect-designed geodesic residence and studio building give you something unmistakably distinctive: a home that feels like art, and a property that can perform like an asset. Inside, the striking residence is fully winterized,

    Sheneur Menaker Hudson Modern Co

    105 Sand Hill Rd, 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
  • /42

    $899,000

    • 4 Beds
    • 3 Baths
    • 1,850 Sq Ft

    73 Lake Ellis Rd, Wingdale, NY 12594

    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,

    Christine Ricci Keller Williams NY Realty

    73 Lake Ellis Rd, Wingdale, NY 12594
  • /3

    $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
  • /2

    $119,000

    • Land
    • 13.31 Acres
    • $8,941 per Acre

    0 Cart Rd Unit KEY833895, Dover, NY 12522

    Nice wooded property with frontage on Cart Rd and 343. Ideal for camp or your hunting cabin. Beautiful view of the town. Priced to sell. 40+ acres also for sale, next to it.

    Graziano Tassone Tassone Realty Corp.

    0 Cart Rd Unit KEY833895, Dover, NY 12522
  • /37

    $490,000

    • 3 Beds
    • 2 Baths
    • 2,168 Sq Ft

    122 Susan Dr, Poughquag, NY 12570

    It's Pretty in Poughquag/Town of Union vale! Must see inside this spacious 3-bedroom, 2-bath home has a versatile, finished lower level with walk-out, separate laundry room & full bath has been nicely renovated! Added bonus of expansive finished lower-level w/walk-out on 1.53 private acres set back on 1.53-acre lot backed up to woods for privacy, this bright, light home features updates

    Susan Stevens BHHS Hudson Valley Properties

    122 Susan Dr, Poughquag, NY 12570
  • /29

    $1,049,000

    • 4 Beds
    • 3.5 Baths
    • 3,350 Sq Ft

    42 Long River Rd, Sherman, CT 06784

    Spend your summer in this beautiful, gated community playing golf on the signature 18-hole course, enjoying a game of tennis or swimming in the heated in ground pool. There is full-service club house complete with a pro shop, pub and restaurant. You can enjoy dining on the patio that overlooks the greens. Inquire about membership details. The home is ready for immediate occupancy, so come up and

    Cynthia Szentkuti Ridgefield Homes Realty

    42 Long River Rd, Sherman, CT 06784
  • /25

    $279,000

    • Land
    • 5.46 Acres
    • $51,099 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
  • /9

    $275,000

    • Land
    • 15.47 Acres
    • $17,776 per Acre

    0 Cricket Hill Rd, Wingdale, NY 12594

    This land is ready for you to fulfill your dreams. 15.47 acres in a pastoral setting. With multiple potential hilltop building sites, choose your view from awe inspiring western sunsets to eastern mountain views overlooking the Ten Mile River. There is plenty of room up top to build your country escape and fulfill your dreams, whether it is adding a barn for a small hobby farm, avid collector,

    Brian McGrath McGrath Realty Inc

    0 Cricket Hill Rd, Wingdale, NY 12594
  • /41

    $480,000

    • 3 Beds
    • 2 Baths
    • 2,230 Sq Ft

    487 Chestnut Ridge Rd, Dover Plains, NY 12522

    Located in Dover Plains, this charming 3-bedroom, 2-bath Colonial offers 2,230 sq. ft. of living space on a 1.27-acre corner lot and includes a detached 2-car garage. Inside, you’ll find an inviting open-concept layout. The main level is perfect for entertaining or everyday living and features a spacious living room with hardwood floors, a large dining room that flows seamlessly to an eat-in

    Robert Washburn RE/MAX Ace Realty

    487 Chestnut Ridge Rd, Dover Plains, NY 12522
  • /50

    $1,399,999

    • 6 Beds
    • 4.5 Baths
    • 4,200 Sq Ft

    57 Cedar Berry Ln, Dover Plains, NY 12522

    Just 90 miles from New York City, at the end of a winding, tree-lined drive, a world unfolds where time slows down, and life takes on a different rhythm. This is the Hudson Valley escape you’ve been waiting for. A custom-built home with detached workshop on nearly five private acres, where every detail was designed to bring comfort, inspiration, and beauty into daily living.The moment you

    Lindsay Stevens eXp Realty

    57 Cedar Berry Ln, Dover Plains, NY 12522
  • /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
  • /44

    $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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