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Wingdale, NY Homes for Sale with Garage

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  • /20

    $356,500

    • 3 Beds
    • 1.5 Baths
    • 1,108 Sq Ft

    39 Maple Ln, Dover Plains, NY 12522

    39 Maple Lane, Dover Plains, NY is being offered for sale for the first time since it was built in 1970. There is a blacktop driveway, a fenced in level yard and an ELEVATOR from ground level to upper level. This home appears to be well built and offers plenty of useable space. The main floor living space speaks for itself with 3 bedrooms, a full bath, living room and dining room. We

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 506-8855

    39 Maple Ln, Dover Plains, NY 12522
  • /49

    $1,299,000

    • 4 Beds
    • 2.5 Baths
    • 4,880 Sq Ft

    53 Dugway Dr, Pawling, NY 12564

    Tucked away on 4.5 acres with hundreds of Acres of landlocked State land behind us in the iconic rolling hills of Pawling Lake Estates, 53 Dugway Drive is more than a house—it's a lifestyle. Just a bit over an hour to NYC by Metro North.... Pull into Our gated fully blacktopped driveway, Nestled in the mountains of Dutchess County. Built in 2025 boasting lifestyle with 10’

    Agent Photo

    Jeannie Shipman

    NextGen Real Estate LLC

    (845) 415-7093

    53 Dugway Dr, Pawling, NY 12564
  • /23

    $469,000

    • 3 Beds
    • 2 Baths
    • 1,523 Sq Ft

    105 S Nellie Hill Rd, Dover Plains, NY 12522

    Circa 1952 - A delightful home that has been totally transformed into a casually elegant masterpiece.The roof was replaced in 2012. The siding was replaced in 2022. The interior of the home was totally redone in 2024.The floors are exquisite, the tiled baths are luxurious, the kitchen is a dream (quartz counter and back splash), and the flow is welcoming. The sun filled deck supports

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 478-1624

    105 S Nellie Hill Rd, Dover Plains, NY 12522
  • /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
  • /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
  • /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
  • /38

    $1,685,000

    • 4 Beds
    • 4.5 Baths
    • 5,475 Sq Ft

    1 Cloverleaf Farm S, Sherman, CT 06784

    Experience the epitome of modern luxury in this expansive contemporary home with captivating long-range southerly VIEWS! This architectural masterpiece is designed with an open plan that seamlessly integrates living, dining and kitchen spaces, creating an environment perfect for sophisticated entertaining and comfortable daily living. Culinary adventures await in the state-of-the-art kitchen,

    Alan O'Doherty William Pitt Sotheby's Int'l

    1 Cloverleaf Farm S, Sherman, CT 06784
  • /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
  • /42

    $899,000 Coming Soon

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

    73 Lake Ellis Rd, Wingdale, NY 12594

    4 miles to Harlem-Valley Wingdale Train Station - 4 miles to beautiful Kent, CT - Less then 2 miles access to route 7, and 2 miles to route 22 - Tucked in/secluded on private road off of Lake Ellis Rd. - Beautiful 10 year old 10 stall barn with hay loft, heated wash stall & tack room - 4 Stall shed row barn - 4 paddocks; 2 large beautiful paddocks and 2 smaller - Beautiful fenced in outdoor

    Christine Ricci Keller Williams NY Realty

    73 Lake Ellis Rd, Wingdale, NY 12594
  • /29

    $595,000

    • 3 Beds
    • 1.5 Baths
    • 1,548 Sq Ft

    311 Kent Rd, Kent, CT 06757

    Set on 3.5 scenic acres overlooking the Housatonic River, this beautifully updated Colonial offers the perfect blend of charm, comfort, and modern living. The property features sweeping mountain views and an in-ground pool, creating an ideal retreat for both relaxation and entertaining. Inside, the sleek, renovated kitchen boasts a center island and opens to a gracious formal dining room, as well

    Steve Pener William Pitt Sotheby's Int'l

    311 Kent Rd, Kent, CT 06757
  • /33

    $369,000

    • 2 Beds
    • 2 Baths
    • 1,700 Sq Ft

    50 Lake Ellis Rd, Wingdale, NY 12594

    Tastefully updated colonial situated on one acre park-like property. Flexible and versatile floor plan offers spacious renovated kitchen w/quartz counters & stainless appliances, huge living room, first floor mudroom/laundry room, two first floor bedrooms and full bathroom. Second floor includes three additional rooms plus full bathroom. New vinyl flooring, fresh paint, new furnace, water heater

    Dan Axtmann BHHS Hudson Valley Properties

    50 Lake Ellis Rd, Wingdale, NY 12594
  • /50

    $865,000

    • 4 Beds
    • 6 Baths
    • 4,788 Sq Ft

    211 Cricket Hill Rd, Dover Plains, NY 12522

    This is the one—an exceptional and truly special property offering the perfect blend of refined living, natural beauty, and flexibility. Set against a breathtaking countryside backdrop, this Colonial Farmhouse-style home is nestled on just over 5 private, picturesque acres—perfectly suited for horses, weekend escapes, or year-round living. With nearly 4,800 square feet of thoughtfully crafted

    Sherri Malone Coldwell Banker Realty

    211 Cricket Hill Rd, Dover Plains, NY 12522
  • /47

    $599,900

    • 3 Beds
    • 2 Baths
    • 2,107 Sq Ft

    28 Gobblers Knob Rd, Pawling, NY 12564

    Welcome to 28 Gobblers Knob Road – A Hudson Valley Retreat! Nestled in the heart of the rolling hills of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on over 20 acres, offering peace, privacy, and natural beauty in every direction. Just over 3 miles from the Metro-North line to Manhattan, you can enjoy the quiet of a country escape without sacrificing

    Mark Snyder eXp Realty

    28 Gobblers Knob Rd, Pawling, NY 12564
  • /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

    149 Johnson Rd, Wingdale, NY 12594
  • /33

    $599,000

    • 4 Beds
    • 4.5 Baths
    • 3,088 Sq Ft

    763 Old State Route 22, Dover Plains, NY 12522

    For those seeking the ultimate in charm and comfort, The Preston House, one of the accommodations at the renowned Old Drovers Inn Bed and Breakfast, is now available for sale. This beautifully renovated 3,088 SF colonial blends old-world elegance with modern conveniences, offering a truly unique living experience. Steeped in history, the home features period architectural details throughout,

    Brian McGrath McGrath Realty Inc

    763 Old State Route 22, Dover Plains, NY 12522
  • /37

    $492,500

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

    122 Susan Dr, Poughquag, NY 12570

    It's Pretty in Poughquag! 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 throughout! Step in main level, you'll

    Susan Stevens BHHS Hudson Valley Properties

    122 Susan Dr, Poughquag, NY 12570
  • /13

    $4,675,000

    • 4 Beds
    • 4.5 Baths
    • 4,024 Sq Ft

    114 Brush Hill Rd, Millbrook, NY 12545

    Brush Hill Contemporary is a to-be-built masterpiece in the Hudson Valley with an inviting and expansive floor plan designed to allow freedom to roam with absolute comfort and luxury. Huge southerly views of the Clove Valley, and beyond, through floor to ceiling windows in the public spaces allow for maximum light and an indoor/outdoor flow that enhances every season. The home will consist of

    Byron Anderson Compass Greater NY, LLC

    114 Brush Hill Rd, Millbrook, NY 12545
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