3,179

Dover Plains, NY Homes

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  • /46

    $815,000

    • 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

    (845) 412-9430

    360 Old State Route 22, Dover Plains, NY 12522
  • /8

    $1,000 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    34 Railroad St Unit 11, Dover Plains, NY 12522

    Property Id: 1266681The 1 bedroom apartment features a grassy yard. Additionally it has ceramic tile in kit, LR, bthrm and engineered floor in bdrm. There are 3 new East-facing windows. Small dogs considered with in-person meet & greet + up to date vet records. Apartment and area outside unit is designated as 100% non-smoking.Semi-designated parking spot for

    (845) 605-7915

    34 Railroad St Unit 11, Dover Plains, NY 12522
  • 214 Old Route 22, Wassaic, NY 12592

    $325,000

    Sold Aug 04, 2025

    214 Old Route 22, Wassaic, NY 12592

    • 3 Beds
    • 1 Bath
    • 1,750 Sq Ft
    • Built 1881

    Last Sold Summary

    • $186/SF
    • 247 Days On Market

    Current Estimated Value $329,903

    Last Listing Agent Samantha Davis BHHS Hudson Valley Properties

    214 Old Route 22, Wassaic, NY 12592
  • /34

    $299,000

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

    14-16 Glen Hill, Dover Plains, NY 12522

    Surrounded by nature. An affordable multifamily compound in the quiet hamlet of Dover Plains—an increasingly rare opportunity to own two homes for the price of one. This unique property features a 3-bedroom/1-bath residence and a separate 2-bedroom/1-bath home, 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

    Barry Malawer Coldwell Banker Realty

    14-16 Glen Hill, 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: 2521509Studio apartment - one tenant only.Third floor.Brand new shower.No pets/smoking.Hot water, garbage collection, snow removal included.

    (845) 442-5021

    31 Wing Ave Unit C3, Dover Plains, NY 12522
  • 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 $378,796

    Last Listing Agent Christopher Ferraro RE/MAX Town & Country

    263 Bog Hollow Rd, Wassaic, NY 12592
  • /46

    $130,000

    Open Sat 12PM - 2PM Coming Soon
    • 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 living and

    Virginia Corbett eXp Realty

    30 Tally-Ho Dr, Dover Plains, NY 12522
  • /2

    $1,050 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    31 Wing Ave Unit A2, Dover Plains, NY 12522

    Property Id: 2506027Ground floor one bedroom apartment. No pets allowed. Minimum credit score 550 required ($20 .00 fee).

    (845) 442-4919

    31 Wing Ave Unit A2, Dover Plains, NY 12522
  • 53B Elizabeth St, Kent, CT 06757

    $440,000

    Sold Jul 11, 2025

    53B Elizabeth St, Kent, CT 06757

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft
    • Built 1962

    Last Sold Summary

    • $399/SF
    • 70 Days On Market

    Current Estimated Value $438,774

    Last Listing Agent Leigh Ann Lengyel Clarke RE/MAX Heritage

    53B Elizabeth St, Kent, CT 06757
  • /3

    $79,000

    $10K PRICE DROP
    • Land
    • 1.49 Acres
    • $53,020 per Acre

    0 Tinker Town Rd, Dover Plains, NY 12522

    Escape the NYC and come to see THIS MIX USE 1.49 acre lot in Amenia, NY. Nestled in the beautiful Dutchess County, this level plot offers endless possibilities for those looking to build a custom home or business or both. This property provides a canvas for your dreams . A Natural Haven Just Minutes from Modern Conveniences, The lots proximity to the Taconic State Parkway and the Dover Plains

    Adnane Chahi Keller Williams Realty Partner

    0 Tinker Town Rd, Dover Plains, NY 12522
  • /15

    $3,100 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
  • 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 $384,020

    Last Listing Agent Larry Havens Havens Real Estate

    105 S Nellie Hill Rd, Dover Plains, NY 12522
  • /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 138 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
  • /13

    $2,200 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
  • /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
  • /35

    $7,500,000

    $500K PRICE DROP
    • 6 Beds
    • 8 Baths
    • 8,933 Sq Ft

    Unlisted Address

    West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open

    Joseph Lorino Brown Harris Stevens HV LLC

    Unlisted Address
  • /35

    $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
  • 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 $382,570

    Last Listing Agent Susan Todd BHHS Hudson Valley Properties

    42 Lime Kiln Rd, Dover Plains, NY 12522
  • /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

    $2,200 Per Month

    • 1 Bed
    • 1 Bath
    • 2,788 Sq Ft
    • Apartment for Rent

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

    Move right into these beautifully renovated, commuter-friendly one-bedroom apartments. This first- and second-floor one-bedroom apartments offer comfortable, modern living. Each unit features a new kitchen and bathroom, along with an open-concept layout that seamlessly connects the living room, dining area, and kitchen. Second-floor apartments include a private balcony. Residents enjoy on-site

    Arleen Shepley Elyse Harney Real Estate

    173 S Amenia Rd Unit 1 & 3, Wassaic, NY 12592
  • 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 $2,923,398

    Last Listing Agent Byron Anderson Compass Greater NY, LLC

    644 Tower Hill Rd, Millbrook, NY 12545
  • /23

    $185,000

    $10K 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
  • /11

    $2,300 Per Month

    • 2 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Townhouse for Rent

    44 Elizabeth St Unit D, Kent, CT 06757

    PRISTINE HALF DUPLEX, TWO BEDROOMS, ONE FULL BATH END UNIT WITH 750 SQ FT ON THE MAIN LEVEL AND 750 SQ FT IN THE LOWER LEVEL FOR STORAGE /UNFINISHED AREA, ALSO A LAUNDRY ROOM AND WASHER/DRYER HOOK-UP IS FOUND IN THE LOWER LEVEL.THE WATER AND LANDSCAPING ARE INCLUDED IN THE RENT. THE TENANT MUST HAVE EXCELLENT CREDIT (700+), AND PROOF OF INCOME. THE RENTAL IS VERY CLOSE TO KENT SCHOOL, KENT

    Bob Camillone Berkshire Hathaway NE Prop.

    44 Elizabeth St Unit D, Kent, CT 06757
  • /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 $378,550

    Last Listing Agent Larry Havens Havens Real Estate

    39 Maple Ln, Dover Plains, NY 12522
    • 51 Elizabeth St, Kent, CT 06757

      Est $1,200,151

      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

  • /23

    $450,000

    $49K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 805 Sq Ft

    105 Sand Hill Rd, Dover Plains, NY 12522

    The Geosphere is a convergence of visionary design, tactical investment and natural sanctuary. Set on 7.18 secluded acres in the heart of Dover Plains, this fully legal, architect-designed geodesic residence and studio building give you something unmistakably distinctive: a home that feels like art, and a property that can perform like an asset. Inside, the striking residence is fully winterized,

    Sheneur Menaker Hudson Modern

    105 Sand Hill Rd, Dover Plains, NY 12522
  • /13

    $2,500 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Apartment for Rent

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

    Now available are two newly renovated two-bedroom apartments, offering comfortable, commuter-friendly living in a convenient location. One unit is located on the first floor and the other on the second floor, providing options to suit a variety of lifestyles. Each apartment has been thoughtfully updated and features a modern kitchen, updated bathroom, and an open-concept layout that seamlessly

    Arleen Shepley Elyse Harney Real Estate

    173 S Amenia Rd Unit 2 & 4, Wassaic, NY 12592
  • 268 Lime Kiln Rd, Dover Plains, NY 12522

    $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 $474,741

    Last Listing Agent Jacqueline Redahan Century 21 Alliance Realty Grp

    268 Lime Kiln Rd, Dover Plains, NY 12522
  • /40

    $3,750,000

    • 7 Beds
    • 7 Baths
    • 6,138 Sq Ft

    151 Benson Hill Rd, Dover Plains, NY 12522

    Rarely does an offering of this scale and provenance come to market. Set across more than 114 acres, Honey Lane Farm is a private estate of exceptional beauty-three distinct period residences forming a serene, self-contained retreat in the heart of the Harlem Valley. The four-bedroom mid-19th century main house is both refined and inviting, bathed in southern light and thoughtfully updated for

    Andrew Gates Houlihan Lawrence

    151 Benson Hill Rd, Dover Plains, NY 12522
  • /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
  • 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

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