Dover Plains, NY Homes

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  /15

  $215,000 Pending

  • Land
  • 9.19 Acres
  • $23,395 per Acre

  0 Kent Rd Unit 20252538, Amenia, NY 12592

  Welcome to 9.19 acres of rolling meadow, offering breathtaking vistas of the Eastern Dutchess County countryside. Tucked away from the road, this peaceful and private setting provides the perfect canvas for your dream home.Whether you're envisioning a simple retreat, a working farm, or a lush garden oasis, this land supports a wide range of possibilities.Enjoy easy access to Metro-North,

  

  Larry Havens

  Havens Real Estate

  (845) 442-1853

  0 Kent Rd Unit 20252538, Amenia, NY 12592
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  /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
• 

  $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 $323,239

  Last Listing Agent Samantha Davis BHHS Hudson Valley Properties

  214 Old Route 22, Wassaic, NY 12592
• 

  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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  /24

  $459,500

  • 4 Beds
  • 4 Baths
  • 3,132 Sq Ft

  3481 New York 22, Dover Plains, NY 12522

  Accepted Offer Conveniently located yet privately tucked away, this home impresses with its large, light filled rooms and thoughtful layout. The lower-level apartment provides excellent flexibility- perfect for multigenerational living or rental income.The first floor offers easy, seamless flow while the finished basement contributes to valuable additional space.Recent updates mean the

  

  Larry Havens

  Havens Real Estate

  (845) 723-3894

  3481 New York 22, 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
• 

  $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 $376,823

  Last Listing Agent Christopher Ferraro RE/MAX Town & Country

  263 Bog Hollow Rd, Wassaic, NY 12592
• 

  Est $547,119 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

  • 37% Above List Price
  • $136/SF
  • 72 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Blake Michaud BHHS Hudson Valley Properties
• 

  

  /11

  $215,000 Pending

  • Land
  • 9.19 Acres
  • $23,395 per Acre

  0 Kent Rd Unit KEY882325, Amenia, NY 12592

  This property is PENDING This listing was extended only. 9.19 versatile acres with remarkable vistas of the gorgeous Eastern Dutchess County countryside. At the moment you will have the ability to select a site for your dream home on this open rolling open meadow. Offering privacy and set well off the road the ideal homesite welcomes your vision and ingenuity.This parcel is currently being

  

  Larry Havens

  Havens Real Estate

  (845) 439-2876

  0 Kent Rd Unit KEY882325, Amenia, NY 12592
• 

  $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 $452,154

  Last Listing Agent Leigh Ann Lengyel Clarke RE/MAX Heritage

  53B Elizabeth St, Kent, CT 06757
• 

  Est $676,737 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

  • 1% Above List Price
  • $219/SF
  • 109 Days On Market

  Last Sold Price $670,000

  Last Listing Agent Arlene Campbell BHHS Hudson Valley Properties
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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
• 

  $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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  /26

  Est $349,680 Not Listed For Sale

  60 Willow Ln, Wassaic, NY 12592

  • 2 Beds
  • 1.5 Baths
  • 1,152 Sq Ft
  • Built 1951

  60 Willow Ln, Wassaic, NY 12592

  Last Sold Summary

  • 15% Above List Price
  • $265/SF
  • 13 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Ron Knowles Century 21 Alliance-NP
• 

  

  /31

  $2,850,000 Pending

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

  644 Tower Hill Rd, Millbrook, NY 12545

  A true country retreat on 109 picturesque acres on one of Millbrook’s most coveted roads, Tower Hill. This extraordinary country estate offers a rare blend of elegance, comfort, and timeless charm. The main residence, originally built in 1909 and remodeled in 2002, features five or six bedrooms, four full bathrooms, and three half bathrooms, designed for both everyday living and grand

  Byron Anderson Compass Greater NY, LLC

  644 Tower Hill Rd, Millbrook, NY 12545
• 

  $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
• 

  Not Listed For Sale

  198 Sinpatch Rd, Wassaic, NY 12592

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft
  • Built 1986

  198 Sinpatch Rd, Wassaic, NY 12592

  Last Sold Summary

  • $56/SF
  • 38 Days On Market

  Last Sold Price $55,000

  Last Listing Agent Evelyn Heady BHHS Hudson Valley Properties
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  /50

  $1,399,999

  • 6 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  57 Cedar Berry Ln, Dover Plains, NY 12522

  Just 90 miles from New York City, at the end of a winding, tree-lined drive, a world unfolds where time slows down, and life takes on a different rhythm. This is the Hudson Valley escape you’ve been waiting for. A custom-built home with detached workshop on nearly five private acres, where every detail was designed to bring comfort, inspiration, and beauty into daily living. The moment you

  Lindsay Stevens eXp Realty

  57 Cedar Berry Ln, 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 $378,080

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  42 Lime Kiln Rd, Dover Plains, NY 12522
• 

  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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  /44

  $2,475,000

  • 4 Beds
  • 4.5 Baths
  • 2,412 Sq Ft

  56 Northrup Rd, Dover Plains, NY 12522

  At the very end of a quiet country road, you'll find 56 Northrup — a stunning, architect-designed retreat blending 19th-century farmhouse charm with thoughtful, award-winning modern design. Originally built in 1870 and reimagined by NYC architects Neumann & Rudy, this 33-acre property includes a restored main house, a sleek single-story primary suite addition, and expansive grounds featuring a

  Adam Hade Compass Greater NY, LLC

  56 Northrup Rd, 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 $370,132

  Last Listing Agent Larry Havens Havens Real Estate

  39 Maple Ln, Dover Plains, NY 12522
• 

  Est $1,203,037 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

  • 1% Above List Price
  • $309/SF
  • 37 Days On Market

  Last Sold Price $1,195,000

  Last Listing Agent Chris Garrity Bain Real Estate
• 

  

  /3

  $79,000

  • 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
• 

  $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
• 

  Est $328,799 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

  • 16% Above List Price
  • $230/SF
  • 13 Days On Market

  Last Sold Price $283,000

  Last Listing Agent Dottie MacRitchie William Pitt
• 

  

  /35

  $8,000,000

  • 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
• 

  $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
• 

  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

  • $440/SF
  • 183 Days On Market

  Last Sold Price $2,750,000

  Last Listing Agent Chris Garrity Bain Real Estate
• 

  

  /19

  $159,000

  • 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
• 

  $415,000 Sold Dec 22, 2025

  23 Bog Hollow Rd, Wassaic, NY 12592

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Above List Price
  • $274/SF
  • 40 Days On Market

  Current Estimated Value $414,533

  Last Listing Agent Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  23 Bog Hollow Rd, Wassaic, NY 12592
• 

  Est $313,506 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

  • 10% Above List Price
  • $232/SF
  • 37 Days On Market

  Last Sold Price $285,500

  Last Listing Agent Lisa Bowman Coldwell Banker Realty
• 

  

  /17

  $59,900

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

  62 Cardinal Ct, Dover Plains, NY 12522

  This home is in good condition and is located in a well maintained 55 and over community. Monthly rentincludes: taxes, water, streetlights and garbage pickup.

  Richard Rennia Richard A. Rennia

  62 Cardinal Ct, Dover Plains, NY 12522
• 

  $290,000 Sold Aug 27, 2025

  126 Christian Hill Rd Unit 128, Dover Plains, NY 12522

  • 2 Beds
  • 1.5 Baths
  • 1,416 Sq Ft
  • Built 1940

  Last Sold Summary

  • 3% Below List Price
  • $205/SF
  • 59 Days On Market

  Current Estimated Value $455,581

  Last Listing Agent Toni Soule Bain Real Estate

  126 Christian Hill Rd Unit 128, Dover Plains, NY 12522
• 

  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
• 

  /2

  $99,900

  • Land
  • 3.3 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
• 

  $485,000 Sold Jul 02, 2025

  3211 Route 22, Dover Plains, NY 12522

  • 3 Beds
  • 3 Baths
  • 1,976 Sq Ft
  • Built 1909

  Last Sold Summary

  • 2% Above List Price
  • $245/SF
  • 52 Days On Market

  Current Estimated Value $475,952

  Last Listing Agent Luis Diaz Century 21 Alliance Realty Grp

  3211 Route 22, Dover Plains, NY 12522
• 

  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
• 

  

  /22

  $759,000

  • 2 Beds
  • 1 Bath
  • 1,386 Sq Ft

  80 Hunter Ln, Amenia, NY 12592

  LOCATION LOCATION ONE OF A KIND PROPERTY HUNTING LAND AND 1,368 sq ft cabin.plus 462 sq ft loft. sleeps 8. three land parcels. 70 ACRES 50 ACRES and 12.4 ACRES for a total of 132.4 Acres. spring fed water system full bath and shower.hot water.wood stove and fire place. generator for electric. taxes approx. $2943 Part in forestry program . every 13 or 14 years you can harvest more mature

  John Melchior Howard Hanna Rand Realty

  80 Hunter Ln, Amenia, NY 12592
• 

  $375,000 Sold Aug 27, 2025

  53 Glen Ave, Dover Plains, NY 12522

  • 3 Beds
  • 1 Bath
  • 1,786 Sq Ft
  • Built 1989

  Last Sold Summary

  • $210/SF
  • 22 Days On Market

  Current Estimated Value $369,661

  Last Listing Agent Diana Wiemer Houlihan Lawrence Inc.

  53 Glen Ave, Dover Plains, NY 12522

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