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Studio to 4 Bedroom Homes for Sale in Wingdale, NY

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  • /23

    $419,000

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

    105 S Nellie Hill Rd, Dover Plains, NY 12522

    Sellers are Motivated. The seller's family has moved abroad. They are very motivated. See new Price! 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

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 478-1624

    105 S Nellie Hill Rd, Dover Plains, NY 12522
  • /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
  • /22

    $130,000

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

    23 Clearview Rd, Wingdale, NY 12594

    23 Clearview Rd, Wingdale, NY – Multi-Family OpportunityTwo 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

    Peggy MacLeay-Generoso McGrath Realty Inc

    23 Clearview Rd, Wingdale, NY 12594
  • /23

    $429,000

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    45 Nicole Ln, Wingdale, NY 12594

    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

    Gianna Schiavone Compass Greater NY, LLC

    45 Nicole Ln, Wingdale, NY 12594
  • /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
  • /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
  • /17

    $59,900

    • 2 Beds
    • 2 Baths
    • 924,924 Sq Ft

    62 Cardinal Ct, Dover Plains, NY 12522

    This home is in good condition and is located in a well maintained 55 and over community. Monthly rentincludes: taxes, water, streetlights and garbage pickup.

    Richard Rennia Richard A. Rennia

    62 Cardinal Ct, Dover Plains, NY 12522
  • /16

    $79,900

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    108 Bluebird Way, Dover Plains, NY 12522

    This home is in good condition and located in a well maintained 55 and over community. Monthly rent includes: taxes, water, streetlights and garbage pickup.

    Richard Rennia Richard A. Rennia

    108 Bluebird Way, Dover Plains, NY 12522
  • /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
  • /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
  • /12

    $150,000

    • 3 Beds
    • 2 Baths
    • 980 Sq Ft

    63 Sasso Ln, Wingdale, NY 12594

    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!!

    Michael Herman McGrath Realty Inc

    63 Sasso Ln, Wingdale, NY 12594
  • /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
  • /47

    $574,900

    • 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
  • /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
  • /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
  • /11

    $169,000

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft

    14 SE Mountain Rd, Wingdale, NY 12594

    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

    Crystal Jones Voro LLC

    14 SE Mountain Rd, Wingdale, NY 12594
  • /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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