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Wingdale, NY Homes for Sale

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  • /27

    $1,199,000

    • 6 Beds
    • 5 Baths
    • 5,532 Sq Ft

    206-208 Dog Tail Corners Rd, Wingdale, NY 12594

    Have you dreamed of owning an incredibly special and unique property? Well, dream no more, now is your chance! A winding driveway off of a small country road, brings you to a custom-built, private, 6-bedroom, 5-bath, light-filled contemporary home with a 2- bedroom guest house, on 7.2+ acres that enjoys 550 feet of frontage on the beautiful Tenmile River, as well as a pond, perfect for swimming,

    Agent Photo

    Ann Stettner

    Neil Charles Real Estate, LLC

    (845) 524-9528

    206-208 Dog Tail Corners Rd, Wingdale, NY 12594
  • /39

    $1,795,000

    • 3 Beds
    • 4.5 Baths
    • 6,831 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
  • /38

    $1,449,000

    • 4 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    32 Long River Rd, Sherman, CT 06784

    Surrounded by breathtaking panoramic views, this newley home offers the ultimate retreat for golf enthusiasts. This single-level residence in the prestigious community of Club River Oaks boasts a variety of amenities tailored to enhance your experience. The generous gourmet kitchen provides the perfect setting for post-game gatherings. Unwind in the open-concept, spacious living areas, where a

    Kevin Donovan Compass Connecticut, LLC

    32 Long River Rd, Sherman, CT 06784
  • /34

    $1,300,000 Open Sat 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 3,544 Sq Ft

    175 Kent Rd, Kent, CT 06757

    Secluded Country Estate with Modern Amenities Nestled on over 11 acres in the charming town of Kent, CT, this beautifully renovated country home, built in 2002, offers the perfect blend of rustic charm and contemporary elegance. The spacious interior boasts a newly renovated country kitchen, ideal for entertaining, and extensive renovations throughout, including new floors, fresh paint inside

    John Engel Douglas Elliman of Connecticut

    175 Kent Rd, Kent, CT 06757
  • /30

    $1,799,999

    • 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
  • /19

    $1,300,000

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

    42 Long River Rd, Sherman, CT 06784

    READY FOR IMMEDIATE OCCUPANCY!! Look forward to spring in Connecticut with views of the Litchfield Hills. Contemporary farm house on beautiful lot located in the Club at River Oaks in Sherman, Connecticut. Located in the rolling hills of Litchfield County, the Club at River Oaks has a signature 18 hole golf course, beautiful club house with a full service bar, gourmet restaurant. tennis courts

    Cynthia Szentkuti Ridgefield Homes Realty

    42 Long River Rd, Sherman, CT 06784
  • /38

    $938,500 New Construction

    • 3 Beds
    • 3 Baths
    • 3,500 Sq Ft

    41 Long River Rd, Sherman, CT 06784

    Fully customizable Scandinavian modern home with walkout finished lower level set on a sprawling 5.46 acre lot on Long River Rd in River Oaks Country Club, a private gated golf course community in Sherman, CT. You select exterior & interior colors, finishes, tile/stone, appliances, etc. 3 bd / 3 bath / 3,500 SF open-concept residence with main level primary, seamlessly connects kitchen (w/

    Donna Kennedy Keller Williams Realty

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

    $650,000

    • 3 Beds
    • 3.5 Baths
    • 3,292 Sq Ft

    50 N Chippawalla Rd, Wingdale, NY 12594

    Have you ever thought to yourself "Someday I'm going to have my own farm or a private retreat upstate..." Well, NOW is your opportunity to own your own PRIVATE 8 ACRE RETREAT in the highly desirable Mid-Hudson Valley! This complex has boundless possibilities including TWO living quarters: A Cape Cod Style Main Home featuring 2 large bedrooms, 2 baths, and a kitchen with so much natural light

    CHRISTOPHER FILANGERI BHHS Hudson Valley Properties

    50 N Chippawalla Rd, Wingdale, NY 12594
  • /30

    $399,000

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    11 Birch Terrace, Pawling, NY 12564

    Welcome to Pawling Lake Estates - a private lake community about 10 minutes outside the Village of Pawling. This adorable cozy Cape is located on a dead-end road. Has 2 bedrooms but can easily live like a 3-bedroom home. Main level has eat in kitchen with breakfast nook, cozy living room with big bay window. 2 Bedrooms and a main bath. Doors in kitchen that lead out to a nice size deck

    Teddie Leonaggeo McGrath Realty Inc

    11 Birch Terrace, Pawling, NY 12564
  • /48

    $799,900 Open Sun 1PM - 3PM

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

    134 Old Pawling Rd, Pawling, NY 12564

    Beautiful Colonial home, Well Maintained level land W/Meadow view, for the first time on the market .This beautiful home offer 4 bedroom and 2 full bathroom and half Den room on the first floor, Bonus Room on the second floor, Formal living room and formal dining room, Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4 bedroom and 2

    Drita Shala Howard Hanna Rand Realty

    134 Old Pawling Rd, Pawling, NY 12564
  • /15

    $390,000

    • Land
    • 10 Acres
    • $40,583 per Acre

    4,10,12 River Oaks Ln, Sherman, CT 06784

    Exceptional opportunity to purchase a 3-lot package totaling 9.62 acres in the prestigious gated community of The Club at River Oaks in Sherman, CT. This private enclave features 66 home sites spread across 350 acres, centered around an 18-hole, par-70 golf course that flows naturally through the Berkshire foothills. The three lots-4 River Oaks Lane (3.12 acres) 10 River Oaks Lane(3.07 acres),

    David Landau RE/MAX Right Choice

    4,10,12 River Oaks Ln, Sherman, CT 06784
  • /32

    $150,000

    • Land
    • 6 Acres
    • $25,685 per Acre

    0 Dugway Dr Unit KEY846082, Dover, NY 12564

    Welcome to Peace and Privacy! Almost 6 acres of Amazing Property, bordering over 400 acres of State Land!! Located just about a 90 min by Metro North, you will have endless outdoor adventures such as The Adirondack Trail as well as the nearby exciting Whaley Lake. Or, if you can have fun without a motorboat, you have your own neighborhood lake and beach around the corner. This expansive property

    Robert Pape Keller Williams NY Realty

    0 Dugway Dr Unit KEY846082, Dover, NY 12564
  • /9

    $1,075,000

    • Land
    • 86 Acres
    • $12,500 per Acre

    Northrup Northrup Rd, Dover, NY 12522

    A special property for someone seeking a quiet private location to create an estate with great view potential. The property is grown over but offers approximately 4o plus or minus acres of crop land if and when reclaimed. High elevations -highest point is 1050 feet. Excellent location, conveniently situated to Millbrook Village, Amenia Village, Kent, Ct., and only two miles to the Hamlet of

    Robert D Ferris R. Ferris Real Estate, LLC

    Northrup Northrup Rd, Dover, NY 12522
  • /25

    $125,000

    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    70 Sasso Ln, Wingdale, NY 12594

    Turn key Living in a Fully Renovated Home!Step into this beautifully renovated home, where comfort meets convenience in a move-in-ready space! Every detail has been upgraded, from the brand-new flooring to the newer appliances, ensuring modern functionality throughout.The spacious living room invites you in with a cozy wood-burning fireplace, perfect for chilly evenings, while the

    Tela Cook McGrath Realty Inc

    70 Sasso Ln, 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
  • /25

    $475,000

    • 3 Beds
    • 3 Baths
    • 2,508 Sq Ft

    1 Craig Ln, Dover Plains, NY 12522

    Great Mother-daughter or income producing apartment in this very well maintained home in Dover. Upstairs has 3 bedrooms and 2 full bathrooms and a separate laundry room. The living room features hardwood flooring and an energy efficient heating and cooling mini split. Downstairs you’ll find a complete one bedroom, 1 bathroom apartment, perfect to offset the mortgage or produce income. New boiler

    Richard Brenner Rich Brenner Realty, LLC

    1 Craig Ln, Dover Plains, NY 12522
  • /26

    $529,000

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

    476 Chestnut Ridge Rd, Dover Plains, NY 12522

    Escape to the serenity of the countryside with this beautifully updated California-style ranch, set on a private and picturesque 2.2-acre property. Designed for both comfort and style, this 3 bedroom home features a 32x16 in-ground pool and ample space for horses, with open fields extending beyond the backyard. Inside, gleaming hardwood floors flow through most of the living space, complementing

    Emelisa Mendoza RE/MAX Town & Country

    476 Chestnut Ridge Rd, Dover Plains, NY 12522
  • /3

    $89,900

    • Land
    • 5 Acres
    • $17,767 per Acre

    0 Sheldon Rd Unit KEY832601, Dover, NY 12594

    Sheldon Rd is peaceful and quiet, not a through road. The road is town maintained. Residential use only, Off-the-Grid homes are acceptable. Upward sloping property is lightly wooded with a pretty seasonal view.

    Lisa Liffland McGrath Realty Inc

    0 Sheldon Rd Unit KEY832601, Dover, NY 12594
  • /34

    $787,000

    • 3 Beds
    • 3 Baths
    • 1,450 Sq Ft

    54 Nanny Hill Rd, Pawling, NY 12564

    This stunning home is brand new from Westchester modular, built with top-of-the-line finishes and quality materials. As soon as you step inside, you'll be greeted by a bright and airy open floor plan that creates a spacious and inviting atmosphere. The chef's kitchen is a standout feature, featuring an oversized island with a prep sink and high-end appliances that are sure to appeal to the

    Kaye Saglibene

    54 Nanny Hill Rd, Pawling, NY 12564
  • /14

    $815,000

    • Land
    • 85 Acres
    • $9,626 per Acre

    0 Chestnut Ridge Rd Unit KEY823877, Dover, NY 12522

    Located on Chestnut Ridge Road, seven miles from the Village of Millbrook, this exceptional and unique 84+ acre land property offers not only great topographic diversity but also has ready approved subdivisions. It consists of two separate tax parcels, complementing each other as a whole or separately. The first 15+ acre lot is accessible with its own long driveway up to a large hay field with

    Marie-Laure Collins Compass Greater NY, LLC

    0 Chestnut Ridge Rd Unit KEY823877, Dover, NY 12522
  • /22

    $319,000

    • 3 Beds
    • 2 Baths
    • 1,080 Sq Ft

    19 Nanas Way, Wingdale, NY 12594

    Nestled on a secluded and private cul de sac with fully developed trees, lies 19 Nanas Way, a light filled 3 bedroom, 2 full bath ranch style home. This is one level living at its best. The kitchen, dining, and living area featuring cathedral ceilings is open concept. The kitchen boasts Bosch SS appliances and a separate pantry. The kitchen door allows direct access to a large walk out deck, with

    Michael Manzino Brown Harris Stevens

    19 Nanas Way, Wingdale, NY 12594
  • /23

    $270,000

    • Land
    • 5 Acres
    • $49,451 per Acre

    LOT 30 Long River Rd, Sherman, CT 06784

    Discover the epitome of tranquility and seclusion with this exceptional 5.46-acre lightly wooded lot, proudly positioned as one of the best in Club River Oaks private country club community in Sherman, CT. Offering an unparalleled canvas for your dream residence, this lot stands out as a gem within the development providing the perfect balance of privacy and access to premium amenities. Situated

    Donna Kennedy Keller Williams Realty

    LOT 30 Long River Rd, Sherman, CT 06784
  • /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
  • /36

    $1,495,000

    • 6 Beds
    • 4.5 Baths
    • 4,110 Sq Ft

    57 Cedar Berry Ln, Dover Plains, NY 12522

    Just 90 miles north of NYC, this stunning Hudson Valley property offers the ultimate live, work, play lifestyle. Nestled on 4.08 private acres, this custom-built log home captures the vibrant essence of the area, known for its booming art and music scene, farm-to-table eateries, outdoor adventures, and local wineries. Generating over $80,000 in VRBO rental income in 2022, this turnkey estate is

    Lindsay Stevens eXp Realty

    57 Cedar Berry Ln, 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 the municipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office, light retail, and

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /11

    $205,000

    • Land
    • 2.50 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 the municipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office, light retail, and

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /11

    $205,000

    • Land
    • 2.03 Acres
    • $100,985 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 the municipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office, light retail, and

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /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 the municipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office, light retail, and

    Adam Hade Compass Greater NY, LLC

    0 New York 22, Dover Plains, NY 12522
  • /7

    $69,900

    • Land
    • 2.70 Acres
    • $25,889 per Acre

    0 Old Pawling Rd Unit ONEH6268329, Dover, NY 12564

    An expansive 2.7-acre parcel of land nestled serenely along a picturesque country road, offering a charming and tranquil setting.The land goes downhill from the road to a designated wetland and then rises quite sharply through mature woodland. This idyllic property is conveniently situated near the highly accessible and major thoroughfare, Route 22, ensuring ease of travel and connectivity to

    Michael Martell eXp Realty

    0 Old Pawling Rd Unit ONEH6268329, Dover, NY 12564
  • /2

    $119,000

    • Land
    • 13 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
  • /2

    $119,000

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

    0 Cart Rd Unit KEYH6268558, 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 KEYH6268558, Dover, NY 12522
  • /2

    $99,900

    • Land
    • 3.30 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 incitive to allow multifamily dwellings to be built and/or commercial use buildings IE shopping centers. Available is survey, and several documents limited topo, tax map, ariels etc. Proposal of a large box store drawings available but not approved.

    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

Frequently Asked Questions

What are the most popular zip codes in Wingdale, NY?
The most popular zip codes in Wingdale, NY include 12603, 12601, 06488, 10512 and 06776.
What are the most popular neighborhoods near Wingdale, NY?
The most popular neighborhoods near Wingdale, NY are Dover, Union Vale, Washington, Beekman and Amenia.
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