Chester, NY Homes

• 

  

  

  /19

  $74,900

  • Land
  • 4.05 Acres
  • $18,494 per Acre

  85 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  85 Carriage Knoll Rd, Chester, NY 12817
• 

  $382,000 Sold Mar 25, 2026

  2915 Whispering Hills Unit 596, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Above List Price
  • $287/SF
  • 43 Days On Market

  Current Estimated Value $374,739

  Last Listing Agent Johanna Monzon Ruballos Century 21 Full Service Realty

  2915 Whispering Hills Unit 596, Chester, NY 10918
• 

  Est $575,318 Not Listed For Sale

  9 Adams Ct, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft
  • Built 1973

  9 Adams Ct, Monroe, NY 10950

  Last Sold Summary

  • 10% Above List Price
  • $228/SF
  • 21 Days On Market

  • Last Sold Price $525,000
  • Oct 19, 2023

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  

  /5

  $35,000 Pending

  • Land
  • 7.07 Acres
  • $4,950 per Acre

  L30 Lane Rd, Chester, NY 12853

  You won't want to miss out on this opportunity! A little over 7 acres (2 parcels) in the heart of the Adirondacks. Close proximity to all the local lakes (Schroon Lake, Loon Lake, Brant Lake) & 10 minutes from Gore Mountain.

  Julia Pucciarelli Gallo Realty ADK Inc

  L30 Lane Rd, Chester, NY 12853
• 

  $675,000 Sold Feb 20, 2026

  23 Pewter Cir, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,318 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Above List Price
  • $291/SF
  • 21 Days On Market

  Current Estimated Value $659,136

  Last Listing Agent Rosemary DelliCarpini eXp Realty

  23 Pewter Cir, Chester, NY 10918
• 

  Est $541,982 Not Listed For Sale

  59 Washington Rd, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,894 Sq Ft
  • Built 1973

  59 Washington Rd, Monroe, NY 10950

  Last Sold Summary

  • 5% Above List Price
  • $272/SF
  • 27 Days On Market

  • Last Sold Price $515,000
  • Aug 29, 2023

  Last Listing Agent Rebecca Kane Keller Williams Hudson Valley
• 

  

  /22

  $68,900

  • Land
  • 3.37 Acres
  • $20,445 per Acre

  86 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  86 Carriage Knoll Rd, Chester, NY 12817
• 

  $345,000 Sold Aug 05, 2025

  326 Heritage Ln, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $203/SF
  • 37 Days On Market

  Current Estimated Value $365,218

  Last Listing Agent Ernie Acampora River Realty Services, Inc.

  326 Heritage Ln, Monroe, NY 10950
• 

  Est $521,441 Not Listed For Sale

  26 Harding Way, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1979

  26 Harding Way, Monroe, NY 10950

  Last Sold Summary

  • 4% Above List Price
  • $287/SF
  • 58 Days On Market

  • Last Sold Price $500,000
  • Jul 15, 2024

  Last Listing Agent Carmela Lopez Borrazas Serhant LLC
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  /26

  $394,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,762 Sq Ft

  195 Eagleton Dr, Monroe, NY 10950

  Beautifully maintained 3-bedroom, 2.5 bath home offering scenic lake views and a comfortable, well-designed layout. This home features stainless steel appliances, fireplace, hardwood floors and numerous recent updates throughout. Enjoy tranquil water views from the charming Juliette balcony perfect for morning coffee or relaxing evenings watching the sunset. Experience the ease of condo living

  Patricia Spagna Century 21 Realty Center

  195 Eagleton Dr, Monroe, NY 10950
• 

  $555,000 Sold Oct 21, 2025

  114 Old Mansion Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 3,330 Sq Ft
  • Built 1930

  Last Sold Summary

  • 21% Below List Price
  • $167/SF
  • 76 Days On Market

  Current Estimated Value $605,125

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  114 Old Mansion Rd, Chester, NY 10918
• 

  Est $524,902 Not Listed For Sale

  67 Washington Rd, Monroe, NY 10950

  • 5 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • Built 1973

  67 Washington Rd, Monroe, NY 10950

  Last Sold Summary

  • 26% Above List Price
  • $199/SF
  • 25 Days On Market

  • Last Sold Price $415,000
  • Jun 12, 2023

  Last Listing Agent Matthew Gibbs Keller Williams Hudson Valley
• 

  

  /38

  $350,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,272 Sq Ft

  307 Gibson Hill Rd, Chester, NY 10918

  Looking for a solid built home with great bones and a lot of space in the Warwick School District? This spacious ranch home is waiting for your modern touches. Built strong, this home is in need of some cosmetic updates but you can live in the home and enjoy it as you go. This home offers 2 bedrooms (plus a den) and a full bath. The kitchen makes every square inch count with ample storage and

  Donna Gennaro Howard Hanna Rand Realty

  307 Gibson Hill Rd, Chester, NY 10918
• 

  $725,000 Sold Jun 30, 2025

  56 Sunset Ridge Rd, Monroe, NY 10950

  • 4 Beds
  • 4 Baths
  • 3,626 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Above List Price
  • $200/SF
  • 34 Days On Market

  Current Estimated Value $771,542

  Last Listing Agent Moses Schreiber MS Realty Group USA, Inc

  56 Sunset Ridge Rd, Monroe, NY 10950
• 

  Est $561,902 Not Listed For Sale

  2 Tyler Place, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1973

  2 Tyler Place, Monroe, NY 10950

  Last Sold Summary

  • 8% Above List Price
  • $267/SF
  • 36 Days On Market

  • Last Sold Price $520,000
  • Oct 05, 2023

  Last Listing Agent Claudia Lepore Keller Williams Realty
• 

  

  /23

  $76,900

  • Land
  • 5.1 Acres
  • $15,078 per Acre

  112 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  112 Carriage Knoll Rd, Chester, NY 12817
• 

  $669,000 Sold Jan 12, 2026

  2 Dawn Ct, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,092 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $216/SF
  • 76 Days On Market

  Current Estimated Value $665,148

  Last Listing Agent Dulce M Ferrera Keller Williams Hudson Valley

  2 Dawn Ct, Chester, NY 10918
• 

  Est $541,566 Not Listed For Sale

  63 Pickerel Rd, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft
  • Built 1969

  63 Pickerel Rd, Monroe, NY 10950

  Last Sold Summary

  • 5% Above List Price
  • $246/SF
  • 42 Days On Market

  • Last Sold Price $515,000
  • Oct 16, 2024

  Last Listing Agent Henry Raymond Thomas M David
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  /32

  $319,900

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  2820 Whispering Hills, Chester, NY 10918

  Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

  Anne Marie Scouarnec R2M Realty Inc.

  2820 Whispering Hills, Chester, NY 10918
• 

  $222,000 Sold Nov 21, 2025

  42 Heaton Rd, Monroe, NY 10950

  • 2 Beds
  • 1 Bath
  • 484 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Below List Price
  • $459/SF
  • 63 Days On Market

  Current Estimated Value $233,152

  Last Listing Agent Maureen Schroder Keller Williams Valley Realty

  42 Heaton Rd, Monroe, NY 10950
• 

  Est $478,369 Not Listed For Sale

  17 Surrey Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,712 Sq Ft
  • Built 1970

  17 Surrey Rd, Chester, NY 10918

  Last Sold Summary

  • 1% Above List Price
  • $277/SF
  • 13 Days On Market

  • Last Sold Price $475,000
  • Nov 20, 2024

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /13

  $460,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  1367 Kings Hwy, Chester, NY 10918

  Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

  Mark Karten Karten Real Estate Svcs LLC

  1367 Kings Hwy, Chester, NY 10918
• 

  $612,500 Sold Sep 05, 2025

  81 Hambletonian Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,938 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Below List Price
  • $316/SF
  • 23 Days On Market

  Current Estimated Value $639,437

  Last Listing Agent Dean Diltz Keller Williams Realty

  81 Hambletonian Rd, Chester, NY 10918
• 

  Est $698,209 Not Listed For Sale

  69 Dug Rd, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 3,006 Sq Ft
  • Built 2001

  69 Dug Rd, Chester, NY 10918

  Last Sold Summary

  • 24% Above List Price
  • $188/SF
  • 124 Days On Market

  • Last Sold Price $565,000
  • Dec 05, 2023

  Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group
• 

  

  /10

  $37,500

  • Land
  • 1.62 Acres
  • $23,148 per Acre

  60 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for

  Walter Swartz Gallo Realty ADK Inc

  60 Carriage Knolls Rd, Chester, NY 12817
• 

  $480,000 Sold Jan 26, 2026

  24 Oak Dr, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft
  • Built 1965

  Last Sold Summary

  • 2% Above List Price
  • $289/SF
  • 35 Days On Market

  Current Estimated Value $482,342

  Last Listing Agent Jay Himelson Howard Hanna Rand Realty

  24 Oak Dr, Monroe, NY 10950
• 

  Est $666,222 Not Listed For Sale

  16 Twin Brooks Dr, Chester, NY 10918

  • 3 Beds
  • 4 Baths
  • 2,708 Sq Ft
  • Built 1968

  16 Twin Brooks Dr, Chester, NY 10918

  Last Sold Summary

  • 2% Above List Price
  • $240/SF
  • 38 Days On Market

  • Last Sold Price $650,000
  • Jun 18, 2024

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center
• 

  

  /36

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  2 Pine Hill Rd, Chester, NY 10918

  The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the

  Richard Ellis Ellis Sotheby's Intl Realty

  2 Pine Hill Rd, Chester, NY 10918
• 

  $338,000 Sold May 15, 2025

  4120 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,282 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $264/SF
  • 69 Days On Market

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

  4120 Whispering Hills Dr, Chester, NY 10918
• 

  Est $494,889 Not Listed For Sale

  14 Twin Brooks Dr, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,692 Sq Ft
  • Built 1968

  14 Twin Brooks Dr, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $281/SF
  • 50 Days On Market

  • Last Sold Price $475,000
  • Feb 18, 2025

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center
• 

  

  /25

  $78,900

  • Land
  • 5.76 Acres
  • $13,698 per Acre

  106 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  106 Carriage Knoll Rd, Chester, NY 12817
• 

  $499,000 Sold Oct 23, 2025

  358 Bull Mill Rd, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 3,120 Sq Ft
  • Built 1840

  Last Sold Summary

  • $160/SF
  • 40 Days On Market

  Current Estimated Value $535,885

  Last Listing Agent Amy Wilhelm Corcoran Baer & McIntosh

  358 Bull Mill Rd, Chester, NY 10918
• 

  Est $598,661 Not Listed For Sale

  73 Dug Rd, Chester, NY 10918

  • 5 Beds
  • 4 Baths
  • 2,554 Sq Ft
  • Built 1971

  73 Dug Rd, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $225/SF
  • 69 Days On Market

  • Last Sold Price $575,000
  • Dec 11, 2024

  Last Listing Agent David Kraus MK Realty Inc
• 

  

  /42

  $305,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  3601 Whispering Hills, Chester, NY 10918

  Welcome to effortless living in the highly sought-after Whispering Hills community! This beautifully maintained 2-bedroom, 1-bath condo with a 1-car garage offers the perfect blend of comfort, style, and convenience.Step inside to discover a warm and inviting space enhanced by custom wall detailing, stylish flooring, and a cozy fireplace, creating the perfect setting for relaxing and

  Janet Rendle Weichert Realtors

  3601 Whispering Hills, Chester, NY 10918
• 

  $425,000 Sold Oct 16, 2025

  8 Hom St, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,410 Sq Ft
  • Built 1962

  Last Sold Summary

  • 11% Below List Price
  • $301/SF
  • 74 Days On Market

  Current Estimated Value $433,393

  Last Listing Agent Joao Rodrigues Preferred Properties Real Esta

  8 Hom St, Chester, NY 10918
• 

  Est $504,139 Not Listed For Sale

  4 Stevens Place, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,882 Sq Ft
  • Built 1969

  4 Stevens Place, Chester, NY 10918

  Last Sold Summary

  • 6% Above List Price
  • $252/SF
  • 56 Days On Market

  • Last Sold Price $475,000
  • Jul 03, 2024

  Last Listing Agent Joan Wortmann Weichert Realtors
• 

  

  /43

  $750,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft

  16 Oxford Springs Rd, Chester, NY 10918

  Discover modern living at its best in this beautifully designed 2,870 sq ft contemporary home with flexible floor plan and wonderful tranquility! Set on 4.1 private acres and featuring its own pond and seasonal babbling brook, 16 Oxford Springs Road is perfect for those seeking a full-time residence or Hudson Valley getaway. This home offers retreat-like privacy yet is only minutes to all

  Jennifer Gold RE/MAX Benchmark Realty Group

  16 Oxford Springs Rd, Chester, NY 10918
• 

  $475,000 Sold Sep 08, 2025

  4 Wood Rd, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,554 Sq Ft
  • Built 1960

  Last Sold Summary

  • $306/SF
  • 73 Days On Market

  Current Estimated Value $474,371

  Last Listing Agent Matthew Skowronski HomeSmart Homes & Estates

  4 Wood Rd, Chester, NY 10918
• 

  Est $628,511 Not Listed For Sale

  46 Ayr Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,784 Sq Ft
  • Built 1971

  46 Ayr Rd, Chester, NY 10918

  Last Sold Summary

  • 28% Above List Price
  • $176/SF
  • 70 Days On Market

  • Last Sold Price $490,000
  • Sep 07, 2023

  Last Listing Agent Eliezer Safdie Sage Realty Center LLC
• 

  

  /48

  $425,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,108 Sq Ft

  40 Poplar Dr, Monroe, NY 10950

  -----Best Value in Monroe — Updated Ranch on Quiet Street with Room to Grow! There may be no better house for the money in Monroe. This adorable, well-maintained ranch clearly shows the pride of ownership from 16 years of loving care. A brand-new front entrance door welcomes you into a bright foyer and spacious living room featuring a large picture window that fills the home with natural

  Richard Froehlich RE/MAX Benchmark Realty Group

  40 Poplar Dr, Monroe, NY 10950

Showing Results 281 - 320, Page 8 of 18