3,089

Dover Plains, 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

    Agent Photo

    Judith 'Judy' Albert

    BHHS Hudson Valley Properties

    360 Old State Route 22, Dover Plains, NY 12522
  • /47

    $4,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • House for Rent

    222 Bog Hollow Rd, Wassaic, NY 12592

    Enjoy privacy, peaceful surroundings, and abundant outdoor space at 222 Bog Hollow Road. This single-family rental is currently configured as a two-bedroom home with two full bathrooms and a private sauna. Two beautiful decks—including an upper-level balcony—provide inviting places to relax, entertain, and enjoy birdwatching. The property is equipped with solar panels and is served by a private

    Agent Photo

    JOSE SANTOS

    K Fortuna Lighthouse Realty

    222 Bog Hollow Rd, Wassaic, NY 12592
  • 263 Bog Hollow Rd, Wassaic, NY 12592

    $380,000

    Sold Feb 04, 2026

    263 Bog Hollow Rd, Wassaic, NY 12592

    • 4 Beds
    • 3 Baths
    • 1,792 Sq Ft
    • Built 1938

    Last Sold Summary

    • 5% Below List Price
    • $212/SF
    • 126 Days On Market

    Current Estimated Value $386,238

    Last Listing Agent Christopher Ferraro RE/MAX Town & Country

    263 Bog Hollow Rd, Wassaic, NY 12592
    • 8 Benson Ln, Dover Plains, NY 12522

      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

  • /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
  • /11

    $2,500 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    173 S Amenia Rd Unit 2 & 4, Wassaic, NY 12592

    Welcome to your new home in the charming district of Wassaic, NY! This inviting property offers a wonderful opportunity for comfortable living in a vibrant community, close to several great restaurants for your dining enjoyment.This property features well-proportioned bedrooms and convenient bathrooms, providing the perfect space for relaxation. With ample floor area, you’ll find plenty

    173 S Amenia Rd Unit 2 & 4, Wassaic, NY 12592
  • 105 S Nellie Hill Rd, 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
    • 460 Sinpatch Rd, Wassaic, NY 12592

      Est $1,826,195

      Not Listed For Sale

      460 Sinpatch Rd, Wassaic, NY 12592

      • 5 Beds
      • 4.5 Baths
      • 3,132 Sq Ft
      • Built 1870
      460 Sinpatch Rd, Wassaic, NY 12592

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Michael Dunstan RE/MAX Town & Country

  • /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
  • /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
  • /15

    $200,000

    Sold May 21, 2026

    0 Kent Rd Unit 20252538, Amenia, NY 12592

    • Land
    • 9.19 Acres
    • $21,763 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 201 Days On Market

    Last Listing Agent Larry Havens Havens Real Estate

    0 Kent Rd Unit 20252538, Amenia, NY 12592
    • 1402 Route 343, Washington, NY 12522

      Est $559,995

      Not Listed For Sale

      1402 Route 343, Washington, NY 12522

      • 4 Beds
      • 3 Baths
      • 2,946 Sq Ft
      • Built 1960
      1402 Route 343, Washington, NY 12522

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Blake Michaud BHHS Hudson Valley Properties

  • /30

    $275,000

    • 5 Beds
    • 2 Baths
    • 2,100 Sq Ft

    14-16 Glen Hill, Dover Plains, NY 12522

    Surrounded by nature. An affordable compound in the quiet hamlet of Dover Plains—an increasingly rare opportunity to own two dwellings for the price of one. This unique property features a 3-bedroom/1-bath residence and a separate 2-bedroom/1-bath residence, both in solid condition with some TLC needed to make them your own. Set on a picturesque parcel at the end of a country road, the setting is

    Barry Malawer Coldwell Banker Realty

    14-16 Glen Hill, Dover Plains, NY 12522
  • /11

    $2,200 Per Month

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

    173 S Amenia Rd Unit 1 & 3, Wassaic, NY 12592

    Welcome to your ideal rental opportunity in the charming community of Wassaic, NY. This delightful property serves as a fantastic base for those seeking comfort and convenience, ideally located near a selection of exceptional restaurants. The residence features central heating and cooling, along with air conditioning and ceiling fans to ensure your comfort year-round. Experience the ease

    173 S Amenia Rd Unit 1 & 3, Wassaic, NY 12592
  • 42 Lime Kiln Rd, Dover Plains, NY 12522

    $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
    • 1046 New York 343, Dover Plains, NY 12522

      Est $620,338

      Not Listed For Sale

      1046 New York 343, Dover Plains, NY 12522

      • 3 Beds
      • 2.5 Baths
      • 3,060 Sq Ft
      • Built 1950
      1046 New York 343, Dover Plains, NY 12522

      Last Sold Summary

      • 109 Days On Market

      Last Listing Agent Arlene Campbell BHHS Hudson Valley Properties

  • /46

    $130,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    30 Tally-Ho Dr, Dover Plains, NY 12522

    Welcome to this beautifully maintained 2-bedroom, 2-bath mobile home in a 55+ community in Dover Plains. Renovated approximately 10 years ago and thoughtfully cared for since, this home offers a warm blend of comfort, character, and practical living space.Inside, you'll find an open-concept layout connecting the living room, dining area, and kitchen, creating an easy flow for everyday

    Virginia Corbett eXp Realty

    30 Tally-Ho Dr, Dover Plains, NY 12522
  • /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
  • 644 Tower Hill Rd, Millbrook, NY 12545

    $2,300,000

    Sold Apr 07, 2026

    644 Tower Hill Rd, Millbrook, NY 12545

    • 6 Beds
    • 8 Baths
    • 6,100 Sq Ft
    • Built 1909

    Last Sold Summary

    • 19% Below List Price
    • $377/SF
    • 160 Days On Market

    Current Estimated Value $2,468,146

    Last Listing Agent Byron Anderson Compass Greater NY, LLC

    644 Tower Hill Rd, Millbrook, NY 12545
    • 6 Jordyn Ln, Dover Plains, NY 12522

      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.

  • /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
  • /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
  • /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
    • 27 Macedonia Brook Rd, Kent, CT 06757

      Est $6,589,215

      Not Listed For Sale

      27 Macedonia Brook Rd, Kent, CT 06757

      • 5 Beds
      • 4.5 Baths
      • 7,632 Sq Ft
      • Built 1827
      27 Macedonia Brook Rd, Kent, CT 06757

      Last Sold Summary

      • 736 Days On Market

      Last Listing Agent Stacey Matthews W. Raveis Lifestyles Realty

  • /26

    $16,500,000

    • 4 Beds
    • 8 Baths
    • 7,500 Sq Ft

    365 Tower Hill Rd, Wassaic, NY 12592

    Introducing Sky House. This 7,500-square-foot modern estate atop 165 acres of meadows, woodland, and rolling hills in Millbrook’s storied hunt country is a study in serenity and design intelligence. Conceived by the celebrated firm Resolution: 4 Architecture and completed in 2019, the residence rises from the landscape with a long, linear silhouette tempered by floor-to-ceiling glass that invites

    Ashley Whittaker Spence Compass Greater NY, LLC

    365 Tower Hill Rd, Wassaic, NY 12592
  • /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
  • 95 Tinker Town Rd, Dover Plains, NY 12522

    $420,000

    Sold Jun 15, 2026

    95 Tinker Town Rd, Dover Plains, NY 12522

    • 2 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • Built 1930

    Last Sold Summary

    • 6% Above List Price
    • $210/SF
    • 48 Days On Market

    Current Estimated Value $416,608

    Last Listing Agent Susan Todd BHHS Hudson Valley Properties

    95 Tinker Town Rd, Dover Plains, NY 12522
    • 51 Elizabeth St, Kent, CT 06757

      Est $1,270,098

      Not Listed For Sale

      51 Elizabeth St, Kent, CT 06757

      • 4 Beds
      • 3.5 Baths
      • 3,866 Sq Ft
      • Built 2010
      51 Elizabeth St, Kent, CT 06757

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Chris Garrity Bain Real Estate

  • /19

    $159,000

    $6K PRICE DROP Pending
    • Land
    • 5.1 Acres
    • $31,176 per Acre

    565 Halls Corners Rd, Dover Plains, NY 12522

    Builder's Dream... A lot was Completed on this Property, survey, well, electric, foundation started, driveway started and more. Build your DREAMHOME on this Beautiful Magnificent Property with BOHA 5.1 acre lot. Many Permits are Completed. Well/ Septic and plans are Board of HealthApproved for a 3 Bedroom home, valid thru July 2027. Completed projects include: Survey. 1+ acre building

    Helen Sclafani World Homes Realty

    565 Halls Corners Rd, Dover Plains, NY 12522
  • /13

    $2,175 Per Month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    173 S Amenia Rd, Wassaic, NY 12592

    Enjoy convenient, commuter-friendly living in these newly renovated one-bedroom apartments, available on both the first and second floors. Thoughtfully updated throughout, each unit features a modern kitchen, updated bath, and an open floor plan designed for comfortable everyday living. Select second-floor units offer a private balcony, providing additional outdoor space to relax and unwind. The

    Arleen Shepley Elyse Harney Real Estate

    173 S Amenia Rd, Wassaic, NY 12592
  • 62 Cardinal Ct, Dover Plains, NY 12522

    $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
    • 16 Elizabeth St Unit 12, Kent, CT 06757

      Est $326,161

      Not Listed For Sale

      16 Elizabeth St Unit 12, Kent, CT 06757

      • 2 Beds
      • 1.5 Baths
      • 1,232 Sq Ft
      • Built 1974
      16 Elizabeth St Unit 12, Kent, CT 06757

      Last Sold Summary

      • 13 Days On Market

      Last Listing Agent Dottie MacRitchie William Pitt Sotheby's Int'l

  • /23

    $175,000

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    110 Gina Dr, Dover Plains, NY 12522

    Beautifully maintained and absolutely gorgeous double manufactured home offering spacious open-concept living in the desirable Tally Ho 55+ community. This home features a large living room with a cozy electric fireplace and a gourmet kitchen loaded with extras, including refrigerator, dishwasher, microwave, propane stove, abundant cabinetry, and a breakfast island perfect for casual dining and

    Robert Dunlop Havens Real Estate

    110 Gina Dr, Dover Plains, NY 12522
  • /30

    $25,000 Per Month

    • 4 Beds
    • 6 Baths
    • 3,978 Sq Ft
    • House for Rent

    85 Kennel Rd, Wassaic, NY 12592

    Unforgettable summer (and perhaps longer) stays in Millbrook’s Tower Hill area of Kennel Road. Comforting sounds of joyful birdsong, lazy days floating in the heated pool, a quick game of hoops or pickleball on your own court, located on the quietest scenic road one could ever find! Ideal proximity to the endless variety the Hudson Valleys local way of life from regenerative farm stands, great

    Candy Anderson Compass Greater NY, LLC

    85 Kennel Rd, Wassaic, NY 12592
  • 108 Bluebird Way, Dover Plains, NY 12522

    $65,000

    Sold Jan 28, 2026

    108 Bluebird Way, Dover Plains, NY 12522

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

    Last Sold Summary

    • 28% Below List Price
    • $70/SF
    • 98 Days On Market

    Last Listing Agent Richard Rennia Richard A. Rennia

    108 Bluebird Way, Dover Plains, NY 12522
    • 34 Macedonia Brook Rd, Kent, CT 06757

      Not Listed For Sale

      34 Macedonia Brook Rd, Kent, CT 06757

      • 4 Beds
      • 4.5 Baths
      • 6,251 Sq Ft
      • Built 2004
      34 Macedonia Brook Rd, Kent, CT 06757

      Last Sold Summary

      • 183 Days On Market

      Last Listing Agent Chris Garrity Bain Real Estate

  • /16

    $950,000

    • 4 Beds
    • 2 Baths
    • 3,005 Sq Ft

    41 Flint Rd, Millbrook, NY 12545

    Welcome to The Flint Road Retreat!! Beautifully maintained one-owner ranch situated on 3.53 private acres along a quiet country road, this property offers a peaceful and serene setting with plenty of room to enjoy the surrounding natural beauty, while remaining just minutes from local shops, restaurants and area amenities. The home features stunning hardwood floors, custom cherry cabinetry,

    AURA QUARTARARO William Pitt Sothebys Int Rlty

    41 Flint Rd, Millbrook, NY 12545
  • /40

    $6,000 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,296 Sq Ft
    • House for Rent

    47 Johnson Rd, Kent, CT 06757

    Embrace the art of living well at Poetess Place, a haven designed for writers, birders, and nature lovers, tucked away on a private riverfront perch in the heart of picturesque Kent, CT. This lovingly remodeled 3-bedroom cottage, each room adorned with queen-sized comfort, invites you into a world of warmth and serenity. Wake up to the soothing melody of the Housatonic River and be captivated by

    Inna Agujen Coldwell Banker Realty

    47 Johnson Rd, Kent, CT 06757
  • 12 Neighborly Ln, Dover Plains, NY 12522

    $69,900

    Sold Aug 13, 2026

    12 Neighborly Ln, Dover Plains, NY 12522

    • 3 Beds
    • 1 Bath
    • 1,324 Sq Ft
    • Built 1960

    Last Sold Summary

    • $53/SF
    • 34 Days On Market

    Current Estimated Value $269,904

    Last Listing Agent Brian Smith River Realty Services, Inc.

    12 Neighborly Ln, Dover Plains, NY 12522
    • 16 Elizabeth St Unit 19, Kent, CT 06757

      Est $318,943

      Not Listed For Sale

      16 Elizabeth St Unit 19, Kent, CT 06757

      • 2 Beds
      • 1.5 Baths
      • 1,232 Sq Ft
      • Built 1980
      16 Elizabeth St Unit 19, Kent, CT 06757

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Lisa Bowman Coldwell Banker Realty

Showing Results 1 - 40, Page 1 of 18

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