Wingdale, NY Homes

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  /38

  $3,900,000

  • 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

  

  Eric Bergers

  William Raveis Real Estate

  (860) 936-9247

  6 Hoyt Rd, Sherman, CT 06784
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  /8

  $2,800 per month

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Apartment for Rent

  804 Berkshire Rd Unit 806, Dover, NY 12594

  Charming 3 bedroom, 1 bath single family home located in Dutchess County. Home features open floor, plenty of storage, close to shopping and minutes from train station. Heat and Hot water included.

  Antoinetta Carino Tag Realty & Property Mang

  804 Berkshire Rd Unit 806, Dover, NY 12594
• 

  $549,000 Sold Jan 28, 2026

  105 Sheldon Rd, Wingdale, NY 12594

  • 4 Beds
  • 3 Baths
  • 2,792 Sq Ft
  • Built 1996

  Last Sold Summary

  • $197/SF
  • 48 Days On Market

  Current Estimated Value $549,531

  Last Listing Agent Barbara Negro Century 21 Alliance Realty Grp

  105 Sheldon Rd, Wingdale, NY 12594
• 

  Est $566,531 Not Listed For Sale

  8 Benson Ln, Dover Plains, NY 12522

  • 4 Beds
  • 2.5 Baths
  • 2,420 Sq Ft
  • Built 2004

  8 Benson Ln, Dover Plains, NY 12522

  Last Sold Summary

  • 8% Above List Price
  • $217/SF
  • 65 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Jackie Calhoun Coldwell Banker Realty
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  /23

  $399,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,788 Sq Ft

  106 Johnson Rd, Wingdale, NY 12594

  Raised Ranch with 3 bedrooms, 1 full bath - Open floor plan with kitchen, dining room and living room. Sliding glass doors to deck and back yard. Basement has finished family room with exterior door to driveway. Laundry room. Lots of potential. Does need work. Owner is selling it as is. Septic 2021, Roof is 15 years old, new breaker box 2025. Located minutes to Route 22 and the Wingdale train

  

  Teddie Leonaggeo

  McGrath Realty Inc

  (845) 252-8278

  106 Johnson Rd, Wingdale, NY 12594
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  /21

  $3,000 per month

  • 3 Beds
  • 1 Bath
  • 1,078 Sq Ft
  • House for Rent

  19 Cedar Ln, Wingdale, NY 12594

  Whole house rental: 3 bedroom, 1 bath, on level .5 acre . First floor: 3 bedroom ,1 bath, living room, dining room, eat in kitchen with door out to deck. Full finished basement with 2 bonus rooms and walk out to patio. Tenant responsible for unities, cable, internet(optimum),garbage, snow and lawn maintenance.Due at Lease signing: 1 month rent & 1 month security. Application, credit check,

  Diana Cirocco Coldwell Banker Realty

  19 Cedar Ln, Wingdale, NY 12594
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  $1,650,000 Sold Feb 10, 2026

  1 Cloverleaf Farm S, Sherman, CT 06784

  • 4 Beds
  • 4.5 Baths
  • 5,475 Sq Ft
  • Built 1989

  Last Sold Summary

  • 8% Below List Price
  • $301/SF
  • 239 Days On Market

  Current Estimated Value $1,578,772

  Last Listing Agent Alan O'Doherty William Pitt Sotheby's Int'l

  1 Cloverleaf Farm S, Sherman, CT 06784
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  Est $531,132 Not Listed For Sale

  6 Jordyn Ln, Dover Plains, NY 12522

  • 3 Beds
  • 3 Baths
  • 1,943 Sq Ft
  • Built 2023

  6 Jordyn Ln, Dover Plains, NY 12522

  Last Sold Summary

  • 12% Above List Price
  • $244/SF
  • 96 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Stacey Cronin Houlihan Lawrence Inc.
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  /38

  $1,295,000 Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,121 Sq Ft

  32 Long River Rd, Sherman, CT 06784

  Welcome home to this exceptionally beautiful modern ranch style property, in a gated community and on one of the areas most elite 18 hole Golf Courses. This sprawling 4 bedroom, 3121 sq. ft. floorplan, on one level and located in the Sherman River Oaks Golf Course, is all you will ever need for family, entertainment and quality living. (whether weekend or year round) Enjoy the beautiful scenery

  Joe Chemero Coldwell Banker Realty

  32 Long River Rd, Sherman, CT 06784
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  $115,000 Sold May 23, 2025

  4 Neighborly Ln, Dover Plains, NY 12522

  • 3 Beds
  • 1 Bath
  • 1,728 Sq Ft
  • Built 1972

  Last Sold Summary

  • 39% Below List Price
  • $67/SF
  • 173 Days On Market

  Current Estimated Value $235,044

  Last Listing Agent Jessica Chutka-Pelletier

  4 Neighborly Ln, Dover Plains, NY 12522
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  Est $179,952 Not Listed For Sale

  7 River Bend Ln, Sherman, CT 06784

  • 4 Beds
  • Built 2001

  7 River Bend Ln, Sherman, CT 06784

  Last Sold Summary

  • 6% Above List Price
  • $65/SF
  • 38 Days On Market

  Last Sold Price $170,000

  Last Listing Agent Donna Kennedy Compass Connecticut, LLC
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  /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
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  $459,000 Sold Jan 27, 2026

  104 Susan Dr, Poughquag, NY 12570

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1985

  Last Sold Summary

  • $270/SF
  • 32 Days On Market

  Current Estimated Value $449,880

  Last Listing Agent Ashley Olson Minard eXp Realty

  104 Susan Dr, Poughquag, NY 12570
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  Est $667,142 Not Listed For Sale

  30 Smoke Ridge Dr, Sherman, CT 06784

  • 4 Beds
  • 2.5 Baths
  • 2,720 Sq Ft
  • Built 1993

  30 Smoke Ridge Dr, Sherman, CT 06784

  Last Sold Summary

  • 27% Above List Price
  • $193/SF
  • 89 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Terence Dominick Exceptional Real Estate LLC
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  /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
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  $383,000 Sold Mar 13, 2026

  105 S Nellie Hill Rd, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,523 Sq Ft
  • Built 1952

  Last Sold Summary

  • 18% Below List Price
  • $251/SF
  • 184 Days On Market

  Current Estimated Value $404,877

  Last Listing Agent Larry Havens Havens Real Estate

  105 S Nellie Hill Rd, Dover Plains, NY 12522
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  Est $641,860 Not Listed For Sale

  28 Anderson Rd, Sherman, CT 06784

  • 4 Beds
  • 2.5 Baths
  • 2,642 Sq Ft
  • Built 1985

  28 Anderson Rd, Sherman, CT 06784

  Last Sold Summary

  • 24% Above List Price
  • $196/SF
  • 46 Days On Market

  Last Sold Price $517,000

  Last Listing Agent Melissa Gordon Coldwell Banker Realty
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  /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
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  $370,000 Sold Feb 02, 2026

  42 Lime Kiln Rd, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,397 Sq Ft
  • Built 1977

  Last Sold Summary

  • 13% Below List Price
  • $265/SF
  • 201 Days On Market

  Current Estimated Value $378,080

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  42 Lime Kiln Rd, Dover Plains, NY 12522
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  Est $817,118 Not Listed For Sale

  10 Smoke Ridge Dr, Sherman, CT 06784

  • 3 Beds
  • 2.5 Baths
  • 3,313 Sq Ft
  • Built 1987

  10 Smoke Ridge Dr, Sherman, CT 06784

  Last Sold Summary

  • 9% Above List Price
  • $226/SF
  • 26 Days On Market

  Last Sold Price $750,000

  Last Listing Agent Kathleen Harrison Coldwell Banker Realty
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  /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
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  $577,000 Sold Oct 21, 2025

  311 Kent Rd, Kent, CT 06757

  • 3 Beds
  • 1.5 Baths
  • 1,548 Sq Ft
  • Built 1947

  Last Sold Summary

  • 3% Below List Price
  • $373/SF
  • 31 Days On Market

  Current Estimated Value $594,548

  Last Listing Agent Steve Pener William Pitt Sotheby's Int'l

  311 Kent Rd, Kent, CT 06757
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  Est $466,443 Not Listed For Sale

  267 Kent Rd, Kent, CT 06757

  • 3 Beds
  • 2 Baths
  • 1,669 Sq Ft
  • Built 1939

  267 Kent Rd, Kent, CT 06757

  Last Sold Summary

  • 10% Above List Price
  • $255/SF
  • 1 Day On Market

  Last Sold Price $425,000

  Last Listing Agent Bonnie Bevans BRealEstate.net
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  /35

  $1,175,000

  • 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
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  /20

  $375,000 Sold Dec 31, 2025

  39 Maple Ln, Dover Plains, NY 12522

  • 3 Beds
  • 1.5 Baths
  • 1,628 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Above List Price
  • $230/SF
  • 132 Days On Market

  Current Estimated Value $370,132

  Last Listing Agent Larry Havens Havens Real Estate

  39 Maple Ln, Dover Plains, NY 12522
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  Est $399,115 Not Listed For Sale

  12 Birch Hill Ln, Kent, CT 06757

  • 2 Beds
  • 1 Bath
  • 1,378 Sq Ft
  • Built 1930

  12 Birch Hill Ln, Kent, CT 06757

  Last Sold Summary

  • 6% Below List Price
  • $308/SF
  • 15 Days On Market

  Last Sold Price $424,500

  Last Listing Agent Dawn Hough Coldwell Banker Realty
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  /41

  $548,000

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft

  503 Chestnut Ridge Rd, Dover Plains, NY 12522

  Escape to your own private sanctuary on two serene acres in the town of Unionvale. This charming oversized ranch home offers the perfect blend of comfort and nature, featuring a cleared, landscaped backyard ideal for gardening or peaceful afternoons, bordered by partly wooded grounds for ultimate privacy. Inside, the warmth of hardwood floors and a wood-burning stove in the dining area creates an

  Tamara LaBarbera Howard Hanna Rand Realty

  503 Chestnut Ridge Rd, Dover Plains, NY 12522
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  $410,000 Sold Jul 24, 2025

  11 Birch Terrace, Pawling, NY 12564

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $293/SF
  • 34 Days On Market

  Current Estimated Value $410,070

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  11 Birch Terrace, Pawling, NY 12564
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  Not Listed For Sale

  211 Kent Rd, Kent, CT 06757

  • 4 Beds
  • 3.5 Baths
  • 2,951 Sq Ft
  • Built 1850

  211 Kent Rd, Kent, CT 06757

  Last Sold Summary

  • $407/SF
  • 95 Days On Market

  Last Sold Price $1,200,000

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty
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  /12

  $3,850,000

  • 4 Beds
  • 4.5 Baths
  • 3,542 Sq Ft

  114 Brush Hill Rd, Millbrook, NY 12545

  Perched above the Clove Valley just minutes from the Village of Millbrook, this exceptional modern residence is designed to celebrate light, landscape, and elevated living in the heart of the Hudson Valley. Set on 51.38 acres of rolling countryside, the home offers breathtaking, panoramic views and a rare sense of privacy, while remaining conveniently close to village amenities. The proposed

  Byron Anderson Compass Greater NY, LLC

  114 Brush Hill Rd, Millbrook, NY 12545
• 

  $380,000 Sold Jan 16, 2026

  9 Nicole Ln, Wingdale, NY 12594

  • 3 Beds
  • 1.5 Baths
  • 1,036 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Above List Price
  • $367/SF
  • 19 Days On Market

  Current Estimated Value $377,103

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  9 Nicole Ln, Wingdale, NY 12594
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  Est $399,519 Not Listed For Sale

  182 Bulls Bridge Rd, South Kent, CT 06785

  • 2 Beds
  • 1 Bath
  • 1,470 Sq Ft
  • Built 1700

  182 Bulls Bridge Rd, South Kent, CT 06785

  Last Sold Summary

  • 20% Above List Price
  • $226/SF
  • 55 Days On Market

  Last Sold Price $332,500

  Last Listing Agent Anna Sogliuzzo Berkshire Hathaway Home Services
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  /13

  $399,999 Pending

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  3057 Pleasant Ridge Rd, Wingdale, NY 12594

  Home needs updating and great potential to expand. Offers walk out basement whichcould be developed for additional spaced. Two car detached garage and house recentlyhad a new roof installed. Located on a county road with easy access on 15 acres with ascenic setting. Less than two hours from New York City and very close to Metro-North.

  Richard Rennia Richard A. Rennia

  3057 Pleasant Ridge Rd, Wingdale, NY 12594
• 

  $465,000 Sold Aug 01, 2025

  268 Lime Kiln Rd, Dover Plains, NY 12522

  • 3 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • Built 2021

  Last Sold Summary

  • $266/SF
  • 19 Days On Market

  Current Estimated Value $465,115

  Last Listing Agent Jacqueline Redahan Century 21 Alliance Realty Grp

  268 Lime Kiln Rd, Dover Plains, NY 12522
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  Est $358,916 Not Listed For Sale

  335 Kent Rd, Kent, CT 06757

  • 3 Beds
  • 3 Baths
  • 1,304 Sq Ft
  • Built 1962

  335 Kent Rd, Kent, CT 06757

  Last Sold Summary

  • 31% Above List Price
  • $210/SF
  • 49 Days On Market

  Last Sold Price $274,000

  Last Listing Agent Dave Fairty E.J. Murphy Realty
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  /22

  $449,000

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  41 Holly Hill Dr, Wingdale, NY 12594

  Newly renovated single-family home located in a quiet community. This 3-bedroom, 2-bathroom residence features updated finishes throughout and a bright, functional layout ideal for everyday living. Enjoy the brand new back deck, perfect for outdoor gatherings and relaxation. A 4-car driveway offers ample off-street parking. The partial basement provides additional storage and flexible space.

  Kevin Chin KRC Elegant Homes Realty Corp.

  41 Holly Hill Dr, Wingdale, NY 12594
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  $435,000 Sold Sep 29, 2025

  27 Cavelo Dr, Wingdale, NY 12594

  • 3 Beds
  • 3 Baths
  • 1,794 Sq Ft
  • Built 1974

  Last Sold Summary

  • $242/SF
  • 31 Days On Market

  Current Estimated Value $431,011

  Last Listing Agent Shannon Tully McGrath Realty Inc

  27 Cavelo Dr, Wingdale, NY 12594
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  Est $322,657 Not Listed For Sale

  232 S Kent Rd, South Kent, CT 06785

  • 3 Beds
  • 1 Bath
  • 716 Sq Ft
  • Built 1900

  232 S Kent Rd, South Kent, CT 06785

  Last Sold Summary

  • 4% Below List Price
  • $468/SF
  • 42 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Dave Fairty E.J. Murphy Realty
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  /4

  $100,000

  • Land
  • 1 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 Hillside Realty & Development

  149 Johnson Rd, Wingdale, NY 12594
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  $550,000 Sold Jul 29, 2025

  46 Peaceable Way, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $281/SF
  • 86 Days On Market

  Current Estimated Value $560,125

  Last Listing Agent Laura Fasciglione Keller Williams Realty Partner

  46 Peaceable Way, Dover Plains, NY 12522

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