Dover Plains, NY Homes

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  /43

  $425,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,640 Sq Ft

  232 Old Route 22, Wassaic, NY 12592

  Step back in time without sacrificing modern comfort in this authentic 1890 Farmhouse nestled in the heart of Wassaic. From the moment you arrive, the magnificent wraparound porch welcomes you to kick back, relax, and take in the Hudson Valley surroundings.Inside, warmth and character abound with numerous built-ins and old world accents. The charming eat-in kitchen features a cozy

  Kathleen Manikowski Compass Greater NY, LLC

  232 Old Route 22, Wassaic, NY 12592
• 

  $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 $439,729

  Last Listing Agent Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  23 Bog Hollow Rd, Wassaic, NY 12592
• 

  Est $427,124

  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

  • 15 Days On Market

  Last Listing Agent Dawn Hough Coldwell Banker Realty
• 

  

  

  /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
• 

  $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 $326,074

  Last Listing Agent Toni Soule Daniel Soule Broker

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

  Est $715,813

  Not Listed For Sale

  6 Lee Cir, Kent, CT 06757

  • 3 Beds
  • 2.5 Baths
  • 2,014 Sq Ft
  • Built 1996

  6 Lee Cir, Kent, CT 06757

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Brian Hastings Serhant Connecticut, LLC
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  /35

  $1,650,000

  • 4 Beds
  • 5 Baths
  • 4,604 Sq Ft

  536 Camby Rd, Verbank, NY 12585

  Privately nestled along a picturesque country road, this exceptional country retreat is set on 8.8 acres of beautifully landscaped grounds, offering an extraordinary blend of privacy, comfort, and natural beauty. Surrounded by mature trees and peaceful scenery, the property provides a tranquil escape while remaining conveniently close to the region’s most sought-after destinations. Thoughtful

  Susan Whalen George T Whalen Real Estate

  536 Camby Rd, Verbank, NY 12585
• 

  

  /18

  $202,500

  Sold Jul 10, 2026

  17 Plymouth Rock Dr, Dover Plains, NY 12522

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1948

  Last Sold Summary

  • 9% Above List Price
  • $264/SF
  • 40 Days On Market

  Current Estimated Value $202,340

  Last Listing Agent Andrew Gates Houlihan Lawrence, Inc.

  17 Plymouth Rock Dr, 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

  • 95 Days On Market

  Last Listing Agent Pels Matthews W. Raveis Lifestyles Realty
• 

  

  /22

  $599,000

  $161K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,386 Sq Ft

  80 Hunter Ln, Amenia, NY 12592

  PRICE JUST REDUCED. DUE TO LIFE EVENTS RECENTLY WILLING TO WORK WITH BUYER THAT CAN APPRECIATE THE PROPERTY. LOCATION LOCATION ONE OF A KIND PROPERTY HUNTING LAND OR A VACATION DESTINATION TO RELAX AND DESTRESS IN THE BEAUTIFUL BERKSHIRE MOUNTAINS 132.4 ACRES PLUS POND.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

  John Melchior Howard Hanna Rand Realty

  80 Hunter Ln, Amenia, NY 12592
• 

  $408,000

  Sold Jun 24, 2026

  840 Old State Route 22, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft
  • Built 1997

  Last Sold Summary

  • 2% Above List Price
  • $220/SF
  • 39 Days On Market

  Current Estimated Value $409,080

  Last Listing Agent Michael Lund Corcoran Country Living

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

  Est $400,793

  Not Listed For Sale

  41 Johnson Rd, Kent, CT 06757

  • 2 Beds
  • 2.5 Baths
  • 1,734 Sq Ft
  • Built 1920

  41 Johnson Rd, Kent, CT 06757

  Last Sold Summary

  • 123 Days On Market

  Last Listing Agent Dave Fairty E.J. Murphy Realty
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  /36

  $475,000

  • 3 Beds
  • 1 Bath
  • 1,680 Sq Ft

  39 Johnson Rd, Kent, CT 06757

  Charming Country Cottage in the Heart of Kent Tucked away on a peaceful private road just a short walk from the vibrant village of Kent. This charming country cottage offers the perfect blend of privacy, convenience, and classic New England character. Surrounded by picturesque meadows and mountain views and located near the scenic Housatonic River, this home provides a tranquil setting while

  Rebecca Ward William Pitt Sotheby's Int'l

  39 Johnson Rd, Kent, CT 06757
• 

  $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 $376,045

  Last Listing Agent Diana Wiemer Houlihan Lawrence Inc.

  53 Glen Ave, Dover Plains, NY 12522
• 

  Est $459,084

  Not Listed For Sale

  53B Elizabeth St, Kent, CT 06757

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

  53B Elizabeth St, Kent, CT 06757

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Leigh Ann Lengyel Clarke RE/MAX Heritage
• 

  

  /23

  $575,000

  $90K PRICE DROP

  • 9 Beds
  • 4 Baths
  • 3,952 Sq Ft

  276 Old Route 22, Wassaic, NY 12592

  Whether you’re seeking an investment property, multi-generational living, or the opportunity to live in one unit while generating rental income from the other two, this versatile property is ready to meet your needs.This well-designed triplex features three townhome-style apartments, each offering three bedrooms, a welcoming front porch, a private rear patio, and a one-car attached

  Stacey Cronin Houlihan Lawrence Inc.

  276 Old Route 22, Wassaic, NY 12592
• 

  $570,000

  Sold Oct 21, 2025

  283 & 279 Johnson Rd, Wingdale, NY 12594

  • 3 Beds
  • 3 Baths
  • 2,058 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $277/SF
  • 32 Days On Market

  Last Listing Agent Lisa Liffland McGrath Realty Inc

  283 & 279 Johnson Rd, Wingdale, NY 12594
• 

  Est $269,833

  Not Listed For Sale

  59 Fuller Mountain Rd, Kent, CT 06757

  • 1 Bed
  • 1 Bath
  • 624 Sq Ft
  • Built 1900

  59 Fuller Mountain Rd, Kent, CT 06757

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Holly Mullins Coldwell Banker Realty
• 

  

  /20

  $4,495,000

  New Construction

  • 4 Beds
  • 5 Baths
  • 5,679 Sq Ft

  101 N Tower Hill Rd, Millbrook, NY 12545

  **TO BE BUILT** Prepare to be impressed. Nestled on nearly 8 private acres in the heart of Millbrook, this exceptional custom-built estate offers nearly 6,000 square feet of thoughtfully designed living space, blending timeless craftsmanship with modern efficiency and luxury. Featuring 4 spacious bedrooms, 5 full baths and oversized 3 car garage, the home provides an ideal balance of comfort,

  Ronald Green KW MidHudson

  101 N Tower Hill Rd, Millbrook, NY 12545
• 

  $374,000

  Sold Dec 12, 2025

  50 Lake Ellis Rd, Wingdale, NY 12594

  • 2 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1948

  Last Sold Summary

  • 1% Above List Price
  • $220/SF
  • 49 Days On Market

  Current Estimated Value $384,160

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  50 Lake Ellis Rd, Wingdale, NY 12594
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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
• 

  

  /11

  $190,000

  • Land
  • 1.66 Acres
  • $114,458 per Acre

  0 New York 22, Dover Plains, NY 12522

  Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
• 

  $202,500

  Sold Jul 10, 2026

  17 Plymouth Rock Rd, Dover Plains, NY 12522

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft
  • Built 1948

  Last Sold Summary

  • 9% Above List Price
  • $264/SF
  • 40 Days On Market

  Current Estimated Value $202,340

  Last Listing Agent Andrew Gates Houlihan Lawrence Inc.

  17 Plymouth Rock Rd, Dover Plains, NY 12522
• 

  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
• 

  

  /21

  $499,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft

  256 Hammond Hill Rd, Dover Plains, NY 12522

  Privately nestled on 3 serene acres in the rolling hills of Dover Plains, this beautifully reimagined country retreat offers an exceptional blend of privacy, refined modern updates, and effortless indoor-outdoor living. Set far back from the road and surrounded by mature trees and picturesque natural scenery, 256 Hammond Hill Road delivers a peaceful lifestyle with extraordinary entertaining

  Anna Proctor Compass Greater NY, LLC

  256 Hammond Hill Rd, Dover Plains, NY 12522
• 

  $450,000

  Sold Dec 09, 2025

  18 Furnace Bank Rd Unit 2, Wassaic, NY 12592

  • 1,920 Sq Ft
  • Built 1900

  Last Sold Summary

  • $234/SF
  • 32 Days On Market

  Current Estimated Value $462,454

  Last Listing Agent Rosa Santiago Weichert Realtors

  18 Furnace Bank Rd Unit 2, Wassaic, NY 12592
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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
• 

  

  /3

  $345,000

  $105K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,318 Sq Ft

  37 Glen Ave, Dover Plains, NY 12522

  2 homes for the price of 1. This is a multi-family property on multiple structures. Two separate electrical meters. 3318 total sq ft with a flowing stream in backyard. Main house consists of 3 bedrooms and 2 baths. Bungalow house has 2 bedrooms and 1 bath. 1 hr to NYC. INVESTORS AND CONTRACTORS SPECIAL. Needs Renovation.

  Ishwar Rameshar YourHomeSold Guaranteed Realty

  37 Glen Ave, Dover Plains, NY 12522
• 

  $875,000

  Sold May 15, 2026

  0 Brush Hill Rd Unit KEY935753, Union Vale, NY 12545

  • Land
  • 51.38 Acres
  • $17,030 per Acre

  Last Sold Summary

  • 27% Below List Price
  • 164 Days On Market

  Last Listing Agent Byron Anderson Compass Greater NY, LLC

  0 Brush Hill Rd Unit KEY935753, Union Vale, NY 12545
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  Not Listed For Sale

  0 Killearn Rd Unit ONEH801744, Washington, NY 12545

  0 Killearn Rd Unit ONEH801744, Washington, NY 12545

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent George Whalen III George T Whalen Real Estate
• 

  /2

  $45,000

  • Land
  • 27,878 Sq Ft
  • $70,312 per Acre

  0 Aldrich Rd, Wingdale, NY 12594

  This 0.64-acre parcel on Aldrich Road in Wingdale, NY is offered at $45,000. This property presents a unique opportunity for an investor or a visionary builder looking to create a custom residence in a quiet, rural setting.Property HighlightsAcreage: 0.64 acres of land in a serene, off-the-beaten-path location.Price: Competitive entry-point pricing at $45,000, reflecting the current

  Mark Snyder eXp Realty

  0 Aldrich Rd, Wingdale, NY 12594
• 

  $9,650,000

  Sold Jun 18, 2026

  1190 Chestnut Ridge Rd, Dover Plains, NY 12522

  • 5 Beds
  • 8 Baths
  • 5,867 Sq Ft
  • Built 2006

  Last Sold Summary

  • 29% Below List Price
  • $1,645/SF
  • 86 Days On Market

  Current Estimated Value $7,695,847

  Last Listing Agent Oliver Brown Houlihan Lawrence Inc.

  1190 Chestnut Ridge Rd, Dover Plains, NY 12522
• 

  

  /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.
• 

  

  /11

  $205,000

  • Land
  • 2.5 Acres
  • $82,000 per Acre

  0 New York 22, Dover Plains, NY 12522

  Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522
• 

  $357,000

  Sold Nov 14, 2025

  10 Raymond Ave, Dover Plains, NY 12522

  • 3 Beds
  • 1.5 Baths
  • 1,520 Sq Ft
  • Built 1964

  Last Sold Summary

  • 6% Below List Price
  • $235/SF
  • 86 Days On Market

  Current Estimated Value $372,570

  Last Listing Agent Larry Havens Havens Real Estate

  10 Raymond Ave, Dover Plains, NY 12522
• 

  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
• 

  

  /24

  $275,000

  $75K PRICE DROP Pending

  • 4 Beds
  • 1.5 Baths
  • 1,792 Sq Ft

  6A Birch Hill Ln, Kent, CT 06757

  Welcome to 6A Birch Hill Lane in Kent, a rare opportunity to own a home with direct frontage on the scenic Housatonic River. If you have been dreaming about peaceful views, the sound of the water, and a setting that truly feels like an escape, this is it. This 4 bedroom, 1.5 bathroom home offers 1,792 square feet of living space with a layout that is both practical and full of potential. The main

  Mark Mermelstein eXp Realty

  6A Birch Hill Ln, Kent, CT 06757
• 

  $503,500

  Sold Jun 02, 2026

  222 Highview Rd, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Above List Price
  • $316/SF
  • 25 Days On Market

  Current Estimated Value $500,421

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  222 Highview Rd, Dover Plains, NY 12522
• 

  Est $483,595

  Not Listed For Sale

  998 Route 343, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft
  • Built 2009

  998 Route 343, Dover Plains, NY 12522

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Ellen 'Ellie' Savoy Houlihan Lawrence Inc.
• 

  

  /11

  $195,000

  • Land
  • 1.85 Acres
  • $105,405 per Acre

  0 New York 22, Dover Plains, NY 12522

  Located on Route 22 in the town of Dover Plains, this Eight-acre site consists of four lots: 1.66-acre(lot 1), 1.85-acre(lot 2),2.03-acre(lot 3), and 2.5-acre(lot 4) development sites. It is currently being re-zoned to Gateway Commercial (GC) by themunicipality. The purpose of the Gateway district is to encourage the development of a compatible mix of commercial, office,light retail,

  Adam Hade Compass Greater NY, LLC

  0 New York 22, Dover Plains, NY 12522

Showing Results 41 - 80, Page 2 of 18