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Newest Homes for Sale in Wingdale, NY

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  • /35

    $385,000

    • 1 Bed
    • 1 Bath
    • 1,080 Sq Ft

    884 Camby Rd, Millbrook, NY 12545

    Estate property being sold AS, including contents. 5+/-acre parcel of lovely land with meadows, views of rolling hill tops and majestic trees. There is an old growth of grape vines and an orchard with various fruit trees. A truly special piece of property conveniently located to communte to NYC either by car or train. Just the land and improvements alone proof the value of this offering. The

    Amy Levine Howard Hanna Rand Realty

    884 Camby Rd, Millbrook, NY 12545
  • /32

    $479,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    326 Old State Route 22, Dover Plains, NY 12522

    Nestled along the banks of the Ten Mile River in Dover Plains, 326 Old State Route 22 offers something truly rare — sweeping open meadows, 800 feet of private river frontage, and a warm, character-filled home all on one extraordinary parcel. With its gambrel roofline, stone chimney, and beautiful grounds, the setting feels both timeless and alive, whether you're watching the current drift past

    Scott Zobre KW MidHudson

    326 Old State Route 22, Dover Plains, NY 12522
  • /45

    $349,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    1889 New York 22, Wingdale, NY 12594

    Move right into this beautifully maintained 3-bedroom, 2-bath home in Dover, NY featuring cathedral ceilings, an open-concept layout, and comfortable everyday living. Conveniently located along Route 22, the property offers easy access to outdoor recreation, local dining, shopping, and Metro-North commuting options. Nearby attractions and amenities include: Scenic hiking, waterfalls, and nature

    Agent Photo

    Milton Hyatt

    KFortuna All Aspects Realty

    (845) 251-3348

    1889 New York 22, Wingdale, NY 12594
  • /24

    $1,999,000

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

    40 Long River 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

    40 Long River Rd, Sherman, CT 06784
  • /40

    $2,495,000

    Open Sun 1PM - 4PM
    • 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
  • /45

    $1,299,000

    • 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
  • /35

    $690,000

    • 2 Beds
    • 2 Baths
    • 1,892 Sq Ft

    231 Kent Rd, Kent, CT 06757

    Tucked away in a peaceful, nature-filled setting just moments from the river, this one-of-a-kind home feels like a private retreat while still being conveniently located for everyday living. Surrounded by mature trees and beautiful scenery, the property offers the kind of setting that's hard to find and even harder to leave. This approximately 1,866 square foot home offers privacy, character, and

    Mark Mermelstein eXp Realty

    231 Kent Rd, Kent, CT 06757
  • /23

    $99,999

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    160 Holsapple Rd Unit 52, Dover Plains, NY 12522

    Spacious 3-Bed, 2-Bath Double-Wide on Premium Corner Lot in Dover Plains Welcome to this large and bright 3-bedroom, 2-full-bath double-wide home, beautifully situated on a meticulously landscaped corner lot. Offering a wonderful blend of private outdoor space and community perks, this property boasts a lush, thick green lawn and a fantastic rear covered deck that is absolutely perfect for

    Steven Collier BHHS Hudson Valley Properties

    160 Holsapple Rd Unit 52, Dover Plains, NY 12522
  • /23

    $499,900

    Open Sun 2PM - 4PM
    • 3 Beds
    • 2 Baths
    • 2,050 Sq Ft

    79 Wendy Dr, Poughquag, NY 12570

    Welcome to 79 Wendy Drive, privately sited on 1.84 beautifully landscaped acres offering a peaceful oasis with mature landscaping, while still enjoying the charm of cul-de-sac living — perfect for neighborhood walks and bike rides. This is a unique opportunity to own this versatile property offering endless potential — ideal for single-family living, multi-generational living, or the opportunity

    Agent Photo

    Amber Thomas

    Compass Greater NY, LLC

    (845) 684-2719

    79 Wendy Dr, Poughquag, NY 12570
  • /23

    $195,000

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    110 Gina Dr, Dover Plains, NY 12522

    Beautifully maintained and absolutely gorgeous double manufactured home offering spacious open-concept living in the desirable Tally Ho 55+ community. This home features a large living room with a cozy electric fireplace and a gourmet kitchen loaded with extras, including refrigerator, dishwasher, microwave, propane stove, abundant cabinetry, and a breakfast island perfect for casual dining and

    Robert Dunlop Havens Real Estate

    110 Gina Dr, Dover Plains, NY 12522
  • /18

    $1,495,000

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,770 Sq Ft

    4 Pond View Ln, Sherman, CT 06784

    New construction 5 bedroom 4.5 bath modern farmhouse colonial in gated upscale golf community. River Oaks offers private 18 hole golf course under new ownership. Lots of upgrades to the clubhouse, restaurand/bar, and the course. River Oaks also has a community pool and tennis courts. The custom home has 2 primary bedrooms, one on the main level and one upstairs. 3 car attcahed garage. 9 Ft

    Joe Chemero Coldwell Banker Realty

    4 Pond View Ln, Sherman, CT 06784
  • /36

    $715,000

    • 3 Beds
    • 3.5 Baths
    • 3,629 Sq Ft

    921 W Dover Rd, Pawling, NY 12564

    A One-of-a-Kind Custom Ranch on Nearly 4 Private Acres. Discover exceptional space, quality, and versatility in this expansive custom-built 3+ bedroom ranch, perfectly tucked away in a serene country setting. Designed for comfort and flexibility, this home is ideal for extended family living, multi-generational needs, or a spacious mother-daughter layout. The main floor offers true single-level

    Joyce Brennan-Zolnik BHHS Hudson Valley Properties

    921 W Dover Rd, Pawling, NY 12564
  • /30

    $440,000

    • 3 Beds
    • 3 Baths
    • 1,556 Sq Ft

    978 W Dover Rd, Pawling, NY 12564

    Welcome to 978 W Dover Road in Pawling, NY—where comfort, space, and scenic beauty come together effortlessly. This inviting home features 3 generously sized bedrooms, 3 full bathrooms, and a dedicated home office, making remote work both productive and enjoyable. The open-concept main level creates a seamless flow between living spaces, perfect for hosting gatherings or simply spending quality

    Regan Andrews Coldwell Banker Realty

    978 W Dover Rd, Pawling, NY 12564
  • /40

    $1,489,000

    Open Sun 12PM - 3PM
    • 4 Beds
    • 3.5 Baths
    • 4,884 Sq Ft

    27 Smoke Ridge Dr, Sherman, CT 06784

    A rare opportunity to own a private 3.70-acre retreat in Sherman-set back from the road down a scenic driveway, offering you seclusion. The stand out one-of-a-kind oversized six car garage easily adapts for, car collections, workspace, or recreational needs. Sherman is known for its low taxes, located just 90 minutes from NYC, this property delivers the ideal balance of privacy and convenience. A

    Ginny Gordon-O’Neill William Raveis Real Estate

    27 Smoke Ridge Dr, Sherman, CT 06784
  • /18

    $185,000

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft

    17 Plymouth Rock Rd, Dover Plains, NY 12522

    A charming and sun-filled 2-bedroom, 1-bath home offering approximately 750 square feet of thoughtfully designed living space in Dover Plains. This inviting pied-à-terre combines comfort and efficiency, making it an ideal full-time residence or weekend retreat.Natural light pours through the home, creating a warm and welcoming atmosphere throughout. The layout maximizes space while

    Andrew Gates Houlihan Lawrence Inc.

    17 Plymouth Rock 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
  • /46

    $815,000

    • 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

    (845) 412-9430

    360 Old State Route 22, Dover Plains, NY 12522
  • /11

    $239,000

    • Land
    • 2.4 Acres
    • $99,583 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
  • /2

    $45,000

    • Land
    • 27,878 Sq Ft
    • $70,312 per Acre

    0 Aldrich Rd, Wingdale, NY 12594

    This 0.64-acre parcel on Aldrich Road in Wingdale, NY is offered at $45,000. This property presents a unique opportunity for an investor or a visionary builder looking to create a custom residence in a quiet, rural setting.Property HighlightsAcreage: 0.64 acres of land in a serene, off-the-beaten-path location.Price: Competitive entry-point pricing at $45,000, reflecting the current

    Mark Snyder eXp Realty

    0 Aldrich Rd, Wingdale, 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

    $249,999

    $100K PRICE DROP
    • 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
  • /34

    $399,000

    $26K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,012 Sq Ft

    113 Dog Tail Corners Rd, Wingdale, NY 12594

    Located on 1.54 acres of scenic land, this charming overbuilt home has a perfect blend of comfort, privacy, and natural beauty. Enjoy open field views across the street from your living room, creating a peaceful backdrop for everyday living and relaxing evenings. The home features a warm and inviting layout, in the living room and kitchen, walls are tongue and groove knotty pine from ceiling to

    Tela Cook McGrath Realty Inc

    113 Dog Tail Corners Rd, Wingdale, NY 12594
  • /40

    $3,750,000

    $150K 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

    (860) 936-9247

    6 Hoyt Rd, Sherman, CT 06784
  • /31

    $900,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,434 Sq Ft

    128 Old Pawling Rd, Pawling, NY 12564

    You finally have the opportunity to own a home with year-round mountain views set on an expansive property. A place where you can bring your vision to life and transform the space into a true masterpiece. 128 Old Pawling Road is a beautifully positioned property in Pawling, NY, offering a rare combination of scenic views, generous land, and the potential to create a truly special home. Set back

    Juliska Martino Compass Greater NY, LLC

    128 Old Pawling Rd, Pawling, NY 12564
  • /35

    $1,175,000

    $120K PRICE DROP
    • 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
  • /9

    $140,000

    $10K PRICE DROP
    • Land
    • 20,037 Sq Ft
    • $304,348 per Acre

    20 Hickory Ln, Pawling, NY 12564

    Build your dream home on this exceptional 0.46-acre parcel, offering a rare blend of privacy, nature, and convenience. The property is BOH approved (3 bedroom residential dwelling), providing a smooth path to construction, and is landlocked at the rear, creating a peaceful, secluded setting. Enjoy access to two nearby lakes for fishing or swimming, or relax at the clubhouse. Drive into Pawling

    Tela Cook McGrath Realty Inc

    20 Hickory Ln, Pawling, NY 12564
  • /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
  • /23

    $450,000

    $49K PRICE DROP
    • 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

    105 Sand Hill Rd, Dover Plains, NY 12522
  • /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
  • /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
  • /2

    $100,000

    • Land
    • 36,154 Sq Ft
    • $120,482 per Acre

    9 Terbar Ct, Dover Plains, NY 12522

    Beautiful flat building lot, no clearing needed! Board of health approved for 4 bedroom home and you only need a small septic on this lot which makes building a home here more cost effective! This level lot is perfect to build your dream home. Bring your own builder or use ours! We can help and assist the first time homebuyer build their dream home through the whole process.

    Bliss Voutsinas Hillside Realty & Development

    9 Terbar Ct, Dover Plains, NY 12522
  • /11

    $175,000

    $24K PRICE DROP
    • 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
  • /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

    $5K PRICE INCREASE
    • 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

    $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

Frequently Asked Questions

What are the most popular zip codes in Wingdale, NY?
The most popular zip codes in Wingdale, NY include 12522, 12594, 12564, 12545 and 06757.
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