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Wingdale, NY Homes for Sale

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  • /20

    $379,900

    • 3 Beds
    • 1.5 Baths
    • 1,520 Sq Ft

    10 Raymond Ave, Dover Plains, NY 12522

    Tucked away at the end of a quiet cul-de-sac, this beautifully maintained country home is on the market for the first time since 1995. The home showcases gleaming hardwood floors throughout, with tasteful tile in the bathrooms. Each room has its own distinct charm and character.The main level features a sun-filled eat-in kitchen that flows seamlessly into a spacious great room with vaulted

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 493-2818

    10 Raymond Ave, Dover Plains, NY 12522
  • /10

    $359,000

    • 3 Beds
    • 1.5 Baths
    • 1,628 Sq Ft

    39 Maple Ln, Dover Plains, NY 12522

    Accepted Offer For the first time this well constructed 3-bedroom, 1.5 bath home on a huge level lot is being offered to settle the Estate. there are no photos online until the home is emptied out. Each room is well proportioned, ample closets, the ceiling height is 7'6", the home is dated, the carpets are worn and need to be replaced. Under the carpet are hardwood floors that will change the

    Agent Photo

    Larry Havens

    Havens Real Estate

    (845) 506-8855

    39 Maple Ln, Dover Plains, NY 12522
  • /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
  • /44

    $575,000

    • 3 Beds
    • 3 Baths
    • 2,058 Sq Ft

    283 & 279 Johnson Rd, Wingdale, NY 12594

    Beautiful house, quiet setting, level park-like property with fully fenced back yard! In 2002, a huge 2nd floor addition and a full renovation of the main floor created an amazing home! The homeowners are INCLUDING 279 Johnson Rd, an adjoining lot with 2 Garages, 40x28 w/heat & 1/2 bath. 2nd garage is 24x24 - More info further down... Total acreage of lots is 1.13 acres. Let's go back to the

    Lisa Liffland McGrath Realty Inc

    283 & 279 Johnson Rd, Wingdale, NY 12594
  • /38

    $548,000

    • 2 Beds
    • 2 Baths
    • 1,425 Sq Ft

    10 Anderson Rd E, Sherman, CT 06784

    MOVE IN READY! Looking for a country retreat, weekend home, artist escape or a work from home space? This charming, ranch home set in a beautiful serene setting has your name on it. This home has great flow and allows the peaceful outside space in- you can feel this the minute you walk through the front door. The living room has almost a full wall of windows showcasing the private garden with

    Ginny Gordon-O’Neill William Raveis Real Estate

    10 Anderson Rd E, Sherman, CT 06784
  • /25

    $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
  • /47

    $649,900

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

    28 Gobblers Knob Rd, Pawling, NY 12564

    Welcome to 28 Gobblers Knob Road – A Hudson Valley Equestrian Retreat! Nestled in the heart of the stunning Hudson Valley, this beautiful 3-bedroom, 2-bathroom home sits on a breathtaking 20+ acre property offering peace, privacy, and natural beauty in every direction. Whether you're looking for a serene country getaway or a horse property, this one-of-a-kind home is the perfect match. The

    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
  • /48

    $799,900

    • 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, 1,25 acres .Gorgeous Oak eating kitchen with sliding door to the deck outside, family room and half bath. Second floor offer 4

    Drita Shala Howard Hanna Rand Realty

    134 Old Pawling Rd, Pawling, NY 12564
  • /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
  • /16

    $289,000

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft

    59 Corbin Rd, Dover Plains, NY 12522

    Welcome to your brand-new, beautifully renovated ranch in the peaceful and sought-after Town of Dover. This isn't just a house; it's a golden opportunity to own a piece of tranquility. Situated on over an acre of lush land, this home offers the perfect escape from the everyday hustle.Step inside and be captivated by the stunning new kitchen, complete with sleek stainless steel appliances. The

    Daniel Deutsch eRealty Advisors, Inc

    59 Corbin Rd, Dover Plains, NY 12522
  • /18

    $290,000

    • 2 Beds
    • 1 Bath
    • 1,362 Sq Ft

    20 Hemlock Ln, Wingdale, NY 12594

    Welcome to this 2 bedroom raised ranch nestled on a quiet cul-de-sac. Offering a perfect blend of privacy and comfort, this home features a spacious, tree-lined yard-ideal for relaxing, entertaining, or gardening. Step out onto the cozy deck and enjoy your morning coffee. Inside, the layout offers functional living space with great natural light and potential to make it your own. The highlight of

    Crystal Neceda Briante Realty Group, LLC

    20 Hemlock Ln, Wingdale, NY 12594
  • /23

    $250,000

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

    6634 Route 55, Wingdale, NY 12594

    This charming 1930s 1,200 sq ft home, with its inviting front enclosed porch, features a traditional layout. The home is in need of some cosmetic updates, a great opportunity for a buyer looking to add their personal touch. The cozy living spaces are bathed in natural light, creating a warm and inviting atmosphere. The home features two comfortable bedrooms, one and a half baths, large dining

    LUCIANA BENNETT McGrath Realty Inc

    6634 Route 55, Wingdale, NY 12594
  • /22

    $279,000

    • Land
    • 5 Acres
    • $51,099 per Acre

    LOT 30 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 Keller Williams Realty

    LOT 30 Long River Rd, Sherman, CT 06784
  • /14

    $80,000

    • Land
    • 1.01 Acres
    • $79,208 per Acre

    15 Evan Rd, Dover Plains, NY 12522

    Attention builders and end users! Level, cleared and shovel ready 1 acre lot in the heart of Dover Plains! Current 4 bedroom BOHA, no fill required for the septic. Backing up to 16+ acres of farm land, come build your dream home today! Bring your own builder or ask about options. Excellent location, minutes to town, the Town of Amenia, Wassaic Train Station, culinary grade restaurants shops and

    Justin LaFalce KW MidHudson

    15 Evan Rd, Dover Plains, NY 12522
  • /9

    $275,000

    • Land
    • 15 Acres
    • $17,776 per Acre

    0 Cricket Hill Rd, Wingdale, NY 12594

    This land is ready for you to fulfill your dreams. 15.47 acres in a pastoral setting. With multiple potential hilltop building sites, choose your view from awe inspiring western sunsets to eastern mountain views overlooking the Ten Mile River. There is plenty of room up top to build your country escape and fulfill your dreams, whether it is adding a barn for a small hobby farm, avid collector,

    Brian McGrath McGrath Realty Inc

    0 Cricket Hill Rd, Wingdale, NY 12594
  • /10

    $130,000

    • 3 Beds
    • 1 Bath
    • 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
  • /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
  • /2

    $100,000

    • Land
    • 0.83 Acre
    • $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

    9 Terbar Ct, Dover Plains, NY 12522
  • /4

    $100,000

    • Land
    • 1.00 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

    149 Johnson Rd, Wingdale, NY 12594
  • /24

    $339,999

    • 3 Beds
    • 2 Baths
    • 1,459 Sq Ft

    218 Johnson Rd, Wingdale, NY 12594

    Charming 3-Bedroom Home on 2.5 Acres in WingdaleWelcome to this well-maintained 3-bedroom, 2-bathroom single-family home offering 1,459 sq. ft. of comfortable living space. Nestled on 2.5 private acres in Wingdale, this home combines peace, privacy, and practicality—perfect for those seeking a forever home. Home is being sold AS-IS.Recent updates include a new sump pump, front

    Jennifer McQueen-Sealy Clarke Realty & Associates LLC

    218 Johnson Rd, Wingdale, NY 12594
  • /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
  • /37

    $497,500

    • 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
  • /33

    $429,000

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    593 Old State Route 22, Dover Plains, NY 12522

    Discover a remarkable, unique country retreat featuring 2 bedrooms and 2 full bathrooms. This home was completely and impeccably renovated in 2022. Nestled on 3.1 acres of private land, this exquisite property offers peace and tranquility as well as wide open spaces just up the hill behind the home with amazing mountain views. When you enter this open concept home, you immediately feel the

    MAUREEN MCELDUFF MULLANEY BHHS Hudson Valley Properties

    593 Old State Route 22, Dover Plains, NY 12522
  • /39

    $1,795,000

    • 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
  • /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
  • /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
  • /14

    $135,000

    • 3 Beds
    • 1.5 Baths
    • 1,900 Sq Ft

    160 Holpsapple Rd Unit 52, Dover Plains, NY 12522

    Welcome to this charming 3-bedroom, 2-bathroom mobile home in Dover! Enjoy the open floor plan with a spacious living area, perfect for gatherings. The well-appointed kitchen offers ample storage, and the primary suite comes with a private bath for added comfort. With two additional bedrooms, this home is perfect for all! Located in a great community, close to local amenities and schools. Don't

    MICHAEL SANTARPIA K. Fortuna Realty, Inc.

    160 Holpsapple Rd Unit 52, Dover Plains, NY 12522
  • /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
  • /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
  • /2

    $97,000

    • Land
    • 3.30 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
  • /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 themunicipality. 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 themunicipality. 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 themunicipality. 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
  • /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 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, 12570 and 06784.
What are the most popular neighborhoods near Wingdale, NY?
The most popular neighborhoods near Wingdale, NY are Dover, Washington, Amenia and Stanford.
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