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Wingdale, NY Homes for Sale with Acreage

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  • /38

    $3,900,000

    • 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

    (860) 936-9247

    6 Hoyt Rd, Sherman, CT 06784
  • /26

    $398,800

    • 3 Beds
    • 2 Baths
    • 1,852 Sq Ft

    840 Old State Route 22, Dover Plains, NY 12522

    Welcome to this beautifully maintained three-bedroom home nestled in the heart of Dover. Offering the perfect blend of comfort and convenience, this property is ideal for both full-time living and a peaceful retreat. Step inside to find a bright and inviting layout featuring a spacious living area, a well-appointed kitchen, and a dining space perfect for everyday living or entertaining. The three

    Michael Lund Corcoran Country Living

    840 Old State Route 22, Dover Plains, NY 12522
  • /8

    $239,000

    • Land
    • 2.4 Acres
    • $99,583 per Acre

    0 Route 22 Unit KEY976107, Dover, NY 12594

    Just above the Town of Pawling border, you will find this 2.4 acre parcel. Now, the Zoning is RU Residential. However, the town of Dover is making zoning changes, expanding the use to include commercial, retail, offices, businesses.

    Lisa Liffland McGrath Realty Inc

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

    $999,000

    • 3 Beds
    • 3.5 Baths
    • 3,258 Sq Ft

    6 River Bend Ln, Sherman, CT 06784

    A spacious contemporary located in a resort quality setting. Located above the fairway of the 13th hole of the Club at River Oaks, an 18 hole golf course masterfully designed around the meandering contours of the Housatonic River on beautifully rolling farmland. The home site boasts mountain valley and seasonal river views and is equipped with a heated gunite, infinity edge pool with attached

    Tyler O'Hazo William Pitt Sotheby's Int'l

    6 River Bend Ln, Sherman, CT 06784
  • /6

    $349,999

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    163 Old State Route 22, Dover Plains, NY 12522

    Discover the perfect blend of potential and land with this quaint cottage in Dover Plains. Nestled on 10.02 acres of expansive property, this two-bedroom, two-bathroom home is ideal for buyers looking to invest in a fixer-upper with endless possibilities. This property is a dream come true for outdoor lovers or those seeking privacy and space to roam, garden, or build. With a very affordable

    German Nielsen Newman Realty Inc

    163 Old State Route 22, Dover Plains, NY 12522
  • /42

    $409,000

    • 3 Beds
    • 1 Bath
    • 1,012 Sq Ft

    113 Dog Tail Corners Rd, Wingdale, NY 12594

    This is an overbuilt charming brick house that can easily be expanded. Look through double windows to an amazing view across the street. In Living room and Kitchen, tongue- and- groove knotty pine from ceiling to floor, brick fireplace in living room will keep the house cozy day/night. Kitchen has knotty-pine cabinets. Park your car (electric garage door) and walk through basement to upstairs and

    Tela Cook McGrath Realty Inc

    113 Dog Tail Corners Rd, Wingdale, NY 12594
  • /35

    $1,175,000

    • 3 Beds
    • 2.5 Baths
    • 2,584 Sq Ft

    46 Spooner Hill Rd, South Kent, CT 06785

    Overlooking neighboring pastureland and set on 5+ private acres with a small pond, this three-bedroom cottage is rich in charm and character. A gracious foyer welcomes you into a sitting room with fireplace and built-ins, and an adjacent formal dining room framed by handsome casement windows. The spacious kitchen offers a center island and sunny breakfast area, opening seamlessly to an outdoor

    Steve Pener William Pitt Sotheby's Int'l

    46 Spooner Hill Rd, South Kent, CT 06785
  • /41

    $548,000

    • 3 Beds
    • 2 Baths
    • 1,852 Sq Ft

    503 Chestnut Ridge Rd, Dover Plains, NY 12522

    Escape to your own private sanctuary on two serene acres in the town of Unionvale. This charming oversized ranch home offers the perfect blend of comfort and nature, featuring a cleared, landscaped backyard ideal for gardening or peaceful afternoons, bordered by partly wooded grounds for ultimate privacy. Inside, the warmth of hardwood floors and a wood-burning stove in the dining area creates an

    Tamara LaBarbera Howard Hanna Rand Realty

    503 Chestnut Ridge Rd, Dover Plains, NY 12522
  • /12

    $3,850,000

    • 4 Beds
    • 4.5 Baths
    • 3,542 Sq Ft

    114 Brush Hill Rd, Millbrook, NY 12545

    Perched above the Clove Valley just minutes from the Village of Millbrook, this exceptional modern residence is designed to celebrate light, landscape, and elevated living in the heart of the Hudson Valley. Set on 51.38 acres of rolling countryside, the home offers breathtaking, panoramic views and a rare sense of privacy, while remaining conveniently close to village amenities. The proposed

    Byron Anderson Compass Greater NY, LLC

    114 Brush Hill Rd, Millbrook, NY 12545
  • /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
  • /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
  • /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
  • /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
  • /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
  • /41

    $460,000

    • 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
  • /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
  • /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
  • /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

    Michael Sadis Compass Greater NY LLC

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