Dover, NY Homes

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  /46

  $795,000

  $20K PRICE DROP

  • 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

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

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

  

  

  /5

  $1,650 Per Month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  22 Maple Ln Unit 1, Dover Plains, NY 12522

  Property Id: 2773715 This move-in ready 1-bedroom, 1-bath apartment offers a bright and comfortable living space with an open living room, spacious bedroom, full bathroom, and convenient kitchen. The apartment includes off-street parking, garbage removal, snow removal, and landscaping, making maintenance simple and hassle-free. Located in the heart of Dover Plains, you’ll enjoy easy

  22 Maple Ln Unit 1, Dover Plains, NY 12522
• 

  $100,000

  Sold Jun 03, 2026

  23 Clearview Rd, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1977

  Last Sold Summary

  • 23% Below List Price
  • $69/SF
  • 267 Days On Market

  Last Listing Agent Peggy MacLeay-Generoso McGrath Realty Inc

  23 Clearview Rd, Wingdale, NY 12594
• 

  Est $574,349

  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

  • 65 Days On Market

  Last Listing Agent Jackie Calhoun Coldwell Banker Realty
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  /38

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 3,434 Sq Ft

  128 Old Pawling Rd, Pawling, NY 12564

  Beautifully situated on 5.5 private acres, this impressive home offers a gated entrance and a long private driveway leading to breathtaking mountain views and a peaceful setting. Relax on the charming rocking-chair front porch and enjoy the serenity of the surrounding landscaped front lawn. Step inside to a dramatic two-story foyer and an abundance of natural light. The spacious kitchen features

  

  Teddie Leonaggeo

  McGrath Realty Inc

  128 Old Pawling Rd, Pawling, NY 12564
• 

  

  /4

  $1,400 Per Month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Condo for Rent

  22 Maple Ln Unit 3, Dover Plains, NY 12522

  Property Id: 2757004 Studio Apartment for Rent Move-in ready first-floor studio apartment (this is a studio, not a one-bedroom) located in a quiet, well-maintained property in Dover Plains. The unit features an open living/sleeping area, a full bathroom, and a functional kitchen with full-size appliances and ample cabinet space. Rent includes cold water, landscaping, snow removal,

  22 Maple Ln Unit 3, Dover Plains, NY 12522
• 

  $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 $566,200

  Last Listing Agent Barbara Negro Century 21 Alliance Realty Grp

  105 Sheldon Rd, Wingdale, NY 12594
• 

  Est $535,734

  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

  • 96 Days On Market

  Last Listing Agent Stacey Cronin Houlihan Lawrence Inc.
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  /40

  $375,000

  • 2 Beds
  • 1 Bath
  • 816 Sq Ft

  28 Birch Terrace, Pawling, NY 12564

  Welcome to 28 Birch Terrace, a charming 2-bedroom, 1-bath Ranch nestled on a private 0.79-acre cul-de-sac lot in the sought-after Pawling Lake Estates community. This move-in ready home features beautifully refinished hardwood floors throughout the Living Room, Dining Area, and bedrooms. The bright Kitchen offers new quartz countertops (2026), tiled floors, and a convenient washer and dryer.

  

  Shannon Tully

  McGrath Realty Inc

  28 Birch Terrace, Pawling, NY 12564
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  /4

  $950 Per Month

  • Studio
  • 1 Bath
  • Condo for Rent

  31 Wing Ave Unit C3, Dover Plains, NY 12522

  Property Id: 2521509 Studio apartment - one tenant only. Third floor. Brand new shower. No pets/smoking. Hot water, garbage collection, snow removal included.

  31 Wing Ave Unit C3, Dover Plains, NY 12522
• 

  $515,000

  Sold Jul 31, 2026

  978 W Dover Rd, Pawling, NY 12564

  • 3 Beds
  • 3 Baths
  • 1,556 Sq Ft
  • Built 1990

  Last Sold Summary

  • 17% Above List Price
  • $331/SF
  • 31 Days On Market

  Current Estimated Value $472,495

  Last Listing Agent Regan Andrews Coldwell Banker Realty

  978 W Dover Rd, Pawling, NY 12564
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  Not Listed For Sale

  0 Drovers Ln Unit KEYM413718, Dover, NY 12522

  0 Drovers Ln Unit KEYM413718, Dover, NY 12522

  Last Sold Summary

  • 233 Days On Market

  Last Listing Agent Mark Snyder eXp Realty
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  /44

  $450,000

  Pending

  • 2 Beds
  • 2 Baths
  • 2,096 Sq Ft

  35 Gobblers Knob Rd, Pawling, NY 12564

  Welcome to 35 Gobblers Knob, a charming Contemporary Cape set on 1.67 beautifully landscaped acres. This spacious 2,009 square foot home offers an open and inviting floor plan featuring a bright Living Room, updated Kitchen, and Dining Area perfect for everyday living and entertaining. The Kitchen opens to a private patio overlooking the scenic property. The main level includes a lovely office

  

  Shannon Tully

  McGrath Realty Inc

  35 Gobblers Knob Rd, Pawling, NY 12564
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  /15

  $2,900 Per Month

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • House for Rent

  32 Reimer Ave, Dover Plains, NY 12522

  Step into this beautifully renovated 3-bedroom, 2-bathroom home and enjoy the perfect blend of modern updates and small-town charm. Featuring brand-new flooring, fresh paint throughout, updated appliances, and numerous recent improvements, this great home has been thoughtfully refreshed from top to bottom. The bright, welcoming interior creates a comfortable place to unwind, while the partially

  Matthew Cave Hudson Property Services, LLC

  32 Reimer Ave, Dover Plains, NY 12522
• 

  $395,000

  Sold Apr 17, 2026

  3057 Pleasant Ridge Rd, Wingdale, NY 12594

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Below List Price
  • $411/SF
  • 78 Days On Market

  Current Estimated Value $397,301

  Last Listing Agent Richard Rennia Richard A. Rennia

  3057 Pleasant Ridge Rd, Wingdale, NY 12594
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  Not Listed For Sale

  0 Cooperstown Rd Unit KEY854621, Dover, NY 12522

  0 Cooperstown Rd Unit KEY854621, Dover, NY 12522

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Curtis Darragh Legacy Land & Homes LLC
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  /40

  $585,000

  • 3 Beds
  • 2.5 Baths
  • 2,122 Sq Ft

  36 Hillside Ave, Wingdale, NY 12594

  Welcome to this well-maintained 3-bedroom, 2.5-bath Colonial, beautifully situated on over 2 private acres near the Pawling border. Surrounded by mature trees, established gardens, and fruit trees, this property offers a peaceful and picturesque setting with plenty of room to relax, garden, and entertain.The main level features a spacious kitchen, attractive parquet wood flooring throughout

  

  Jackie Calhoun

  Coldwell Banker Realty

  36 Hillside Ave, Wingdale, NY 12594
• 

  $449,000

  Sold Jun 03, 2026

  41 Holly Hill Dr, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1996

  Last Sold Summary

  • $335/SF
  • 45 Days On Market

  Current Estimated Value $445,100

  Last Listing Agent Kevin Chin KRC Elegant Homes Realty Corp.

  41 Holly Hill Dr, Wingdale, NY 12594
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  Not Listed For Sale

  70 Sasso Ln, Wingdale, NY 12594

  • 2 Beds
  • 1 Bath
  • 980 Sq Ft
  • Built 1978

  70 Sasso Ln, Wingdale, NY 12594

  Last Sold Summary

  • 106 Days On Market

  Last Listing Agent Tela Cook McGrath Realty Inc
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  /2

  $100,000

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

  9 Ter Bar 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 Ter Bar Ct, Dover Plains, NY 12522
• 

  $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 $392,849

  Last Listing Agent Larry Havens Havens Real Estate

  105 S Nellie Hill Rd, Dover Plains, NY 12522
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  Not Listed For Sale

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

  • 6 Beds
  • 5 Baths
  • 5,532 Sq Ft
  • Built 2009

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

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Ann Stettner Neil Charles Real Estate, LLC
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  /12

  $314,900

  • 2 Beds
  • 1 Bath
  • 1,378 Sq Ft

  122 Weil Rd, Wingdale, NY 12594

  Two bedroom, one bath cottage on an amazing pastoral setting on a 6.16 acre lot in the town of Dover. Great place for a weekend retreat or year-round home. Bring your imagination and renovate this home to your needs. Amazing setting! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with rehab loan financing must be accompanied by a pre-qualification letter; cash offers with proof

  Brian Smith River Realty Services, Inc.

  122 Weil Rd, Wingdale, NY 12594
• 

  $365,000

  Sold May 01, 2026

  106 Johnson Rd, Wingdale, NY 12594

  • 3 Beds
  • 1 Bath
  • 1,788 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $204/SF
  • 24 Days On Market

  Current Estimated Value $377,446

  Last Listing Agent Teddie Leonaggeo McGrath Realty Inc

  106 Johnson Rd, Wingdale, NY 12594
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  Not Listed For Sale

  126 Reagans Mill Rd, Wingdale, NY 12594

  • 2 Beds
  • 2 Baths
  • 1,048 Sq Ft
  • Built 1992

  126 Reagans Mill Rd, Wingdale, NY 12594

  Last Sold Summary

  • 68 Days On Market

  Last Listing Agent Mark Snyder eXp Realty
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  /43

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,686 Sq Ft

  73 Lake Ellis Rd, Wingdale, NY 12594

  A rare opportunity for the dedicated equestrian, this beautiful gentleman’s farm is set on nearly 9 acres of gently rolling countryside, offering the ideal balance of privacy, usability and convenience. Whether you’re an active competitor, trail rider or simply seeking a peaceful horse property, this special offering provides the setting to pursue your passion.Perfect as a full-time residence

  Lonnie Lum Coldwell Banker Realty

  73 Lake Ellis Rd, Wingdale, NY 12594
• 

  $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 $389,662

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  42 Lime Kiln Rd, Dover Plains, NY 12522
• 

  Est $572,457

  Not Listed For Sale

  46 Peaceable Way, Dover Plains, NY 12522

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

  46 Peaceable Way, Dover Plains, NY 12522

  Last Sold Summary

  • 86 Days On Market

  Last Listing Agent Laura Fasciglione Keller Williams Realty Partner
• 

  

  /30

  $1,299,999

  $500K PRICE DROP Pending

  • 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 Compass Greater NY LLC

  165 Duell Hollow Rd, Wingdale, NY 12594
• 

  

  /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 $387,499

  Last Listing Agent Larry Havens Havens Real Estate

  39 Maple Ln, Dover Plains, NY 12522
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  Not Listed For Sale

  0 Chestnut Ridge Rd Unit KEY823877, Dover, NY 12522

  0 Chestnut Ridge Rd Unit KEY823877, Dover, NY 12522

  Last Sold Summary

  • 82 Days On Market

  Last Listing Agent Marie-Laure Collins Compass Greater NY, LLC
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  /45

  $1,250,000

  $49K PRICE DROP

  • 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
• 

  $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 $380,590

  Last Listing Agent Claudia Jiskra McGrath Realty Inc

  9 Nicole Ln, Wingdale, NY 12594
• 

  

  /16

  Est $663,036

  Not Listed For Sale

  565 Poplar Hill Rd, Dover Plains, NY 12522

  565 Poplar Hill Rd, Dover Plains, NY 12522

  Last Sold Summary

  • 106 Days On Market

  Last Listing Agent Michael Tellerday Houlihan Lawrence, Inc.
• 

  

  /5

  $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
• 

  $55,000

  Sold Jun 24, 2026

  62 Cardinal Ct, Dover Plains, NY 12522

  • 2 Beds
  • 2 Baths
  • 924,924 Sq Ft
  • Built 1981

  Last Sold Summary

  • 15% Below List Price
  • $0/SF
  • 209 Days On Market

  Last Listing Agent Richard Rennia Richard A. Rennia

  62 Cardinal Ct, Dover Plains, NY 12522
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  Not Listed For Sale

  116 Bluebird Way, Dover Plains, NY 12522

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1985

  116 Bluebird Way, Dover Plains, NY 12522

  Last Sold Summary

  • 112 Days On Market

  Last Listing Agent Richard Rennia Richard A. Rennia
• 

  

  /11

  $199,000

  $40K PRICE DROP

  • Land
  • 2.4 Acres
  • $82,917 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
• 

  $99,000

  Sold Jul 15, 2026

  61 Sasso Ln, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $88/SF
  • 23 Days On Market

  Last Listing Agent BRIDGET CAPAWANA Exit Realty Connections

  61 Sasso Ln, Wingdale, NY 12594
• 

  Est $476,204

  Not Listed For Sale

  31 White Oak Cir, Wingdale, NY 12594

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • Built 2000

  31 White Oak Cir, Wingdale, NY 12594

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Joann Perna Guardian Realty Center, LLC

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