Wingdale, NY Homes for Sale

• 

  

  

  /41

  $435,000

  • 3 Beds
  • 3 Baths
  • 1,794 Sq Ft

  27 Cavelo Dr, Wingdale, NY 12594

  Tucked away at the end of a quiet cul-de-sac on 1.79 picturesque acres, this beautifully maintained 3-bedroom, 3-bath home offers the perfect blend of privacy, space, and convenience. Step inside and head upstairs to a sun-filled, open-concept living space where the hardwood floors flow through a spacious Living Room and adjoining Dining Room. Large windows bathe the space in natural light, while

  

  Shannon Tully

  McGrath Realty Inc

  (845) 328-6912

  27 Cavelo Dr, Wingdale, NY 12594
• 

  

  

  /34

  $650,000

  • 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
• 

  

  

  /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
• 

  

  

  /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

  $749,900

  • 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
• 

  

  /44

  $750,000

  • 3 Beds
  • 4.5 Baths
  • 5,500 Sq Ft

  238 Deer Hollow Rd, Poughquag, NY 12570

  This elegant contemporary colonial style home has 3 bedrooms, 4 baths, a library and is reminiscent of the Nantucket Cottage style with a New York flair. three car attached garage.Built, with septic and well installed, the home is ready for you to finish with heat and plumbing. Electrical 75% complete and interior finishes to your own taste. With a separate home office space, a work life balance

  Howard Payson RE/MAX Town & Country

  238 Deer Hollow Rd, Poughquag, NY 12570
• 

  

  /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, 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
• 

  

  /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
• 

  /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
• 

  

  /24

  $1,850,000

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft

  783 N Clove Rd, Millbrook, NY 12545

  Sited far off the road, this charming Colonial Revival home sits discreetly amongst the surrounding fields, meadows, and woodlands comprising the 122 acre property. There are two parcels, the main parcel with house on 77 acres, and the adjacent parcel of 45.7 acres, both spanning North Clove Rd with well over 2000’ of road frontage. The home was built in 1986, with major renovations in 2000, but

  Dan Kessler Compass Greater NY, LLC

  783 N Clove Rd, Millbrook, NY 12545
• 

  

  /40

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft

  42 Lime Kiln Rd, Dover Plains, NY 12522

  Perfectly set back on beautiful park-like property showcasing spectacular panoramic mountain views and a small babbling brook at the back of the property that flows from the Ten Mile River. Bright spacious floor plan features hardwood floors through first floor, updated granite & maple kitchen with stainless steel appliances, and a recently remodeled bath with a custom tile & seamless glass

  Susan Todd BHHS Hudson Valley Properties

  42 Lime Kiln 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
• 

  

  /33

  $419,000

  • 4 Beds
  • 2 Baths
  • 1,656 Sq Ft

  198 Benson Hill Rd, Dover Plains, NY 12522

  Your Private Oasis Awaits: A Raised Ranch with Panoramic Views!Discover the potential in this four-bedroom, two-bath raised ranch, perfectly situated on just over an acre of private land. Imagine waking up to breathtaking panoramic mountain views right from your own home!This property offers a fantastic layout, including a finished basement that provides versatile living space with a family room,

  LUCIANA BENNETT McGrath Realty Inc

  198 Benson Hill Rd, Dover Plains, NY 12522
• 

  

  /39

  $449,000

  • 3 Beds
  • 1.5 Baths
  • 1,610 Sq Ft

  22 Riverdale Dr, Wingdale, NY 12594

  Lovely raised ranch home. Large flat backyard for entertaining with a deck and an inground pool. Three bedroom, 1.5 bath. Living room has a lovely fireplace.Finished basement with pellet stove, family room and bar and laundry. Central A/C. Town water and sewer. Separate large shed for workshop/storage. NY Star savings $572.29 not included in taxes. A/O 6/18/25

  Dianna Ferrieri My Seasons Realty LLC

  22 Riverdale Dr, Wingdale, NY 12594
• 

  

  /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

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,108 Sq Ft

  25 White Farm Rd, Wingdale, NY 12594

  Beautifully Updated Raised Ranch in Country Mill EstatesThis move-in ready home offers the perfect blend of comfort, charm, and convenience. Nestled in the serene neighborhood of Country Mill Estates, the property features a spacious front and back yard with mature shade trees and well-maintained flower beds, creating a welcoming outdoor space.Inside, you'll find a bright and open floor plan. The

  Jonathan Scarinzi Elyse Harney Real Estate

  25 White Farm Rd, Wingdale, NY 12594
• 

  

  /24

  $380,000

  • 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.Recent updates include a new sump pump, front siding, and sunroom windows (2023), along

  Jennifer McQueen-Sealy Clarke Realty & Associates LLC

  218 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
• 

  

  /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

  Tucked away in the tranquil hills of Poughquag town of Unionvale, 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
• 

  

  /33

  $449,000

  • 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

  • 3 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
• 

  

  /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
• 

  

  /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
• 

  

  /26

  $119,900

  • 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 primary bedroom

  Tela Cook McGrath Realty Inc

  70 Sasso Ln, Wingdale, NY 12594
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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

Showing Results 1 - 40, Page 1 of 2