Dover Plains, NY Homes

• 

  

  

  /49

  $398,000

  Pending

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

  95 Tinker Town Rd, Dover Plains, NY 12522

  Incredible value meets timeless country charm in this truly special property, tucked away on nearly a full acre of beautifully landscaped land. Set back from the road, this serene retreat is defined by a rare and captivating feature...a true whitewater stream that runs the entire length of the property, offering a peaceful soundtrack and a setting that feels like a getaway every single day. The

  Susan Todd BHHS Hudson Valley Properties

  95 Tinker Town 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 $414,009

  Last Listing Agent Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  23 Bog Hollow Rd, Wassaic, NY 12592
• 

  Est $314,656

  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
• 

  

  

  /17

  $55,000

  $10K PRICE DROP Pending

  • 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 $347,185

  Last Listing Agent Toni Soule Daniel Soule Broker

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

  Est $419,306

  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
• 

  /2

  $99,900

  $5K PRICE INCREASE

  • 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 $485,724

  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

  • 95 Days On Market
• 

  

  /22

  $759,000

  $1K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,386 Sq Ft

  80 Hunter Ln, Amenia, NY 12592

  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 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

  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 $370,925

  Last Listing Agent Diana Wiemer Houlihan Lawrence Inc.

  53 Glen Ave, Dover Plains, NY 12522
• 

  Est $365,803

  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
• 

  

  /32

  $479,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  326 Old State Route 22, Dover Plains, NY 12522

  Nestled along the banks of the Ten Mile River in Dover Plains, 326 Old State Route 22 offers something truly rare — sweeping open meadows, 800 feet of private river frontage, and a warm, character-filled home all on one extraordinary parcel. With its gambrel roofline, stone chimney, and beautiful grounds, the setting feels both timeless and alive, whether you're watching the current drift past

  Scott Zobre KW MidHudson

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

  $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 $261,645

  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
• 

  

  /23

  $599,000

  $66K 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 garage. Every

  Stacey Cronin Houlihan Lawrence Inc.

  276 Old Route 22, Wassaic, NY 12592
• 

  $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 $372,153

  Last Listing Agent Dan Axtmann BHHS Hudson Valley Properties

  50 Lake Ellis Rd, Wingdale, NY 12594
• 

  Est $1,261,114

  Not Listed For Sale

  19 Nodine Pasture Rd, Kent, CT 06757

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft
  • Built 1990

  19 Nodine Pasture Rd, Kent, CT 06757

  Last Sold Summary

  • 380 Days On Market
• 

  

  /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
• 

  $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 $452,891

  Last Listing Agent Rosa Santiago Weichert Realtors

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

  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
• 

  

  /40

  $7,500,000

  $500K PRICE DROP

  • 6 Beds
  • 9 Baths
  • 8,933 Sq Ft

  33 Nodine Pasture Rd, Kent, CT 06757

  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

  Jill Sloane Brown Harris Stevens

  33 Nodine Pasture Rd, Kent, CT 06757
• 

  $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
• 

  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
• 

  

  /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
• 

  $519,000

  Sold Jul 08, 2025

  476 Chestnut Ridge Rd, Dover Plains, NY 12522

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Below List Price
  • $337/SF
  • 76 Days On Market

  Current Estimated Value $526,259

  Last Listing Agent Emelisa Mendoza RE/MAX Town & Country

  476 Chestnut Ridge Rd, Dover Plains, NY 12522
• 

  

  /16

  Est $695,650

  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
• 

  

  /18

  $185,000

  Pending

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  17 Plymouth Rock Dr, Dover Plains, NY 12522

  A charming and sun-filled 2-bedroom, 1-bath home offering approximately 750 square feet of thoughtfully designed living space in Dover Plains. This inviting pied-à-terre combines comfort and efficiency, making it an ideal full-time residence or weekend retreat. Natural light pours through the home, creating a warm and welcoming atmosphere throughout. The layout maximizes space while maintaining a

  Andrew Gates Houlihan Lawrence, Inc.

  17 Plymouth Rock Dr, 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 $365,689

  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
• 

  

  /26

  $398,800

  Pending

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

  840 Old State Route 22, Dover Plains, NY 12522

  Welcome to this beautifully maintained three-bedroom home nestled in the heart of Dover. Offering the perfect blend of comfort and convenience, this property is ideal for both full-time living and a peaceful retreat. Step inside to find a bright and inviting layout featuring a spacious living area, a well-appointed kitchen, and a dining space perfect for everyday living or entertaining. The three

  Michael Lund Corcoran Country Living

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

  $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 $604,764

  Last Listing Agent Susan Todd BHHS Hudson Valley Properties

  222 Highview Rd, Dover Plains, NY 12522
• 

  Est $436,645

  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
• 

  

  /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
• 

  $80,000

  Sold Nov 13, 2025

  15 Evan Rd, Dover Plains, NY 12522

  • Land
  • 1.01 Acres
  • $79,208 per Acre

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Justin LaFalce KW MidHudson

  15 Evan Rd, Dover Plains, NY 12522
• 

  Est $282,109

  Not Listed For Sale

  26 Balsam Ct, Dover Plains, NY 12522

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft
  • Built 1987

  26 Balsam Ct, Dover Plains, NY 12522

  Last Sold Summary

  • 246 Days On Market
• 

  

  /18

  $185,000

  Pending

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  17 Plymouth Rock Rd, Dover Plains, NY 12522

  A charming and sun-filled 2-bedroom, 1-bath home offering approximately 750 square feet of thoughtfully designed living space in Dover Plains. This inviting pied-à-terre combines comfort and efficiency, making it an ideal full-time residence or weekend retreat.Natural light pours through the home, creating a warm and welcoming atmosphere throughout. The layout maximizes space while

  Andrew Gates Houlihan Lawrence Inc.

  17 Plymouth Rock Rd, Dover Plains, NY 12522
• 

  $389,000

  Sold Oct 13, 2025

  154 Bog Hollow Rd, Wassaic, NY 12592

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 2004

  Last Sold Summary

  • $312/SF
  • 22 Days On Market

  Current Estimated Value $395,517

  Last Listing Agent Stephen Pener William Pitt Sothebys Int Rlty

  154 Bog Hollow Rd, Wassaic, NY 12592
• 

  Est $252,658

  Not Listed For Sale

  8 Tinker Town Rd, Dover Plains, NY 12522

  • 2 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 1931

  8 Tinker Town Rd, Dover Plains, NY 12522

  Last Sold Summary

  • 122 Days On Market
• 

  

  /3

  $399,900

  $50K 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

Showing Results 41 - 80, Page 2 of 18