Chester, NY Homes

• 

  

  

  /20

  $489,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  3 Hickory Ln, Monroe, NY 10950

  Welcome to this beautifully fully renovated 4-bedroom, 2-bath home, thoughtfully updated in 2026 with modern finishes throughout. This spacious property offers a bright open-concept layout featuring a large living room, dining area, and a stunning modern kitchen complete with a skylight and abundant natural light. Enjoy new flooring and moldings throughout, freshly painted interiors, and

  Pearl Ungar eRealty Advisors, Inc

  3 Hickory Ln, Monroe, NY 10950
• 

  $270,000 Sold Apr 28, 2025

  1213 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1984

  Last Sold Summary

  • 4% Below List Price
  • $249/SF
  • 94 Days On Market

  Current Estimated Value $274,609

  Last Listing Agent Nicholas D'Aloisio Keller Williams Rlty Integrity

  1213 Whispering Hills, Chester, NY 10918
• 

  Est $557,776 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

  • 8% Above List Price
  • $246/SF
  • 42 Days On Market

  Last Sold Price $515,000

  Last Listing Agent Henry Raymond Thomas M David
• 

  

  

  /31

  $59,500 Pending

  • Land
  • 5.42 Acres
  • $10,978 per Acre

  L7 Macglashan Ln, Chester, NY 12817

  Very nice 5.42 acres of property with plenty of secluded building options. Gently sloping topography with mixed hardwood and conifers throughout. An abundance of wildlife signs from end to end of this parcel. This property is zoned ''Rural Use'' and would be used ideally for a home or cabin (one-primary single family residence) with garage or other auxiliary building. Seller financing possible

  Walter Swartz Gallo Realty ADK Inc

  L7 Macglashan Ln, Chester, NY 12817
• 

  

  

  /13

  $79,500 Sold Dec 09, 2025

  L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817

  • Land
  • 14.7 Acres
  • $5,408 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 110 Days On Market

  Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc

  L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
• 

  Est $478,791 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

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /19

  $83,500

  • Land
  • 2.84 Acres
  • $29,401 per Acre

  38 Granite Ridge Rd, Chester, NY 12817

  Private 2.84-acre partially cleared, buildable lot in a peaceful setting with proposed home and septic locations. Property features a gravel driveway with camper pad, Amish-built shed on gravel base, fire pit, and walking trail. Infrastructure in place includes 200-amp underground electric service plus 30-amp and 50-amp RV hookups. Conveniently located minutes from Cronin's Golf Resort, Friends

  Nicholas Khachadourian KW Platform

  38 Granite Ridge Rd, Chester, NY 12817
• 

  $550,000 Sold Mar 09, 2026

  12 Juniper Ln, Monroe, NY 10950

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft
  • Built 1972

  Last Sold Summary

  • 4% Below List Price
  • $240/SF
  • 120 Days On Market

  Current Estimated Value $544,185

  Last Listing Agent Shaylene Neumann Houlihan Lawrence Inc.

  12 Juniper Ln, Monroe, NY 10950
• 

  Est $704,870 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

  • 25% Above List Price
  • $188/SF
  • 124 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group
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  /7

  $39,500

  • Land
  • 2.38 Acres
  • $16,597 per Acre

  22 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 a

  Walter Swartz Gallo Realty ADK Inc

  22 Carriage Knolls Rd, Chester, NY 12817
• 

  $782,000 Sold Apr 03, 2025

  152 Gibson Hill Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,176 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Below List Price
  • $246/SF
  • 230 Days On Market

  Current Estimated Value $773,727

  Last Listing Agent Kimberly Corkum Keller Williams Realty

  152 Gibson Hill Rd, Chester, NY 10918
• 

  Est $675,043 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

  • 4% Above List Price
  • $240/SF
  • 38 Days On Market

  Last Sold Price $650,000

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center
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  /36

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,644 Sq Ft

  2 Moffatt Ln, Chester, NY 10918

  Quaint ranch offering comfort, convenience, and room to make it your own. This 2-bedroom, 2-full bathroom home features hardwood floors and a practical layout with great natural light. The finished walk-out basement adds valuable living space with plenty of possibilities: home office, recreation area or guest space. There is also abundant storage throughout the home. Enjoy outdoor living with a

  Maria Kriesel Century 21 Full Service Realty

  2 Moffatt Ln, Chester, NY 10918
• 

  $75,000 Sold Jul 09, 2025

  31 Leone Ln, Chester, NY 10918

  • Land
  • 7.5 Acres
  • $10,000 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 73 Days On Market

  Last Listing Agent Carole McCann Hudson Heritage Realty

  31 Leone Ln, Chester, NY 10918
• 

  Est $487,828 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

  • 3% Above List Price
  • $281/SF
  • 50 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center
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  /48

  $499,999

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  35 Maple Ln, Monroe, NY 10950

  Is there a 3-bed ranch in Monroe NY under $500K with a finished basement, pool, and commuter convenience? 35 Maple Ln is a 3-bedroom, 2-bathroom ranch offered at $499,999 with 1,460 sq ft of living space, including 960 sq ft above grade and a 500 sq ft finished basement. Built in 1964, this single family residence offers true single level living plus flexible lower level space ideal for

  Kewin Garabito eXp Realty

  35 Maple Ln, Monroe, NY 10950
• 

  $665,000 Sold Jul 15, 2025

  174 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,608 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $255/SF
  • 27 Days On Market

  Current Estimated Value $675,162

  Last Listing Agent Michele Tobin Keller Williams Realty

  174 Creamery Pond Rd, Chester, NY 10918
• 

  Est $607,223 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

  • 6% Above List Price
  • $225/SF
  • 69 Days On Market

  Last Sold Price $575,000

  Last Listing Agent David Kraus MK Realty Inc
• 

  

  /8

  $849,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
• 

  $465,000 Sold Aug 04, 2025

  559 Laroe Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1970

  Last Sold Summary

  • 11% Below List Price
  • $245/SF
  • 239 Days On Market

  Current Estimated Value $468,095

  Last Listing Agent Eliezer Safdie Sage Realty Center LLC

  559 Laroe Rd, Chester, NY 10918
• 

  Est $506,636 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

  • 7% Above List Price
  • $252/SF
  • 56 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Joan Wortmann Weichert Realtors
• 

  

  /16

  $37,500

  • Land
  • 2 Acres
  • $18,750 per Acre

  13 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 a

  Walter Swartz Gallo Realty ADK Inc

  13 Carriage Knolls Rd, Chester, NY 12817
• 

  $501,500 Sold Mar 03, 2026

  16 Mari Rd, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,098 Sq Ft
  • Built 1970

  Last Sold Summary

  • $239/SF
  • 75 Days On Market

  Current Estimated Value $502,865

  Last Listing Agent Kimberly Corkum Keller Williams Realty

  16 Mari Rd, Chester, NY 10918
• 

  Est $605,962 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

  • 24% Above List Price
  • $176/SF
  • 70 Days On Market

  Last Sold Price $490,000

  Last Listing Agent Eliezer Safdie Sage Realty Center LLC
• 

  

  /4

  $350,000

  • Land
  • 5.1 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  Theresa Powers Keller Williams Realty

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
• 

  $457,500 Sold Jul 25, 2025

  12 Mari Rd, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,842 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $248/SF
  • 32 Days On Market

  Current Estimated Value $460,344

  Last Listing Agent Ryan Degnan Howard Hanna Rand Realty

  12 Mari Rd, Chester, NY 10918
• 

  Est $436,391 Not Listed For Sale

  13 Mari Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,358 Sq Ft
  • Built 1970

  13 Mari Rd, Chester, NY 10918

  Last Sold Summary

  • 10% Above List Price
  • $291/SF
  • 40 Days On Market

  Last Sold Price $395,000

  Last Listing Agent Debbie Goldstein Howard Hanna Rand Realty
• 

  

  /18

  $299,000 Pending

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

  3120 Whispering Hills, Chester, NY 10918

  Welcome to this charming 2-bedroom condo in the desirable Whispering Hills community! This unit faces green space and trees for added privacy as well as comfortable living spaces. The home features a cozy living room with a fireplace, a dining area, and a full kitchen ready for everyday meals or weekend entertaining. Enjoy the convenience of having your own in-unit washer and dryer, plus a

  Bente Brown John J Lease REALTORS Inc

  3120 Whispering Hills, Chester, NY 10918
• 

  $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 $433,774 Not Listed For Sale

  33 Trotting Dr, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft
  • Built 1968

  33 Trotting Dr, Chester, NY 10918

  Last Sold Summary

  • 14% Above List Price
  • $242/SF
  • 84 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Jackie Siracuse Absolute Real Estate of NY Inc
• 

  

  /8

  $225,000

  • Land
  • 1 Acre
  • $225,000 per Acre

  34 Mountainside Dr, Chester, NY 10918

  Lovely 1-Acre lot w/MOUNTAIN VIEWS & NATURAL GAS in a beautiful newly built SUB-DIVISION. Build out this nearly completely built lovely sub-division, curb-cuts, paved road sloping lot perfect for a WALK-OUT BASEMENT and DECKS FOR BEAUTIFUL VIEWS ... FULLY APPROVED LOT, ESTABLISHED NEIGHBORHOOD, VERY COMMUTABLE location! Close to the vibrant shopping, restaurants, nightlife, shows/events at Sugar

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
• 

  $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 $502,799 Not Listed For Sale

  62 Surrey Rd, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,872 Sq Ft
  • Built 1968

  62 Surrey Rd, Chester, NY 10918

  Last Sold Summary

  • 3% Above List Price
  • $262/SF
  • 37 Days On Market

  Last Sold Price $490,000

  Last Listing Agent Valerie Quinn Keller Williams Realty
• 

  

  /24

  $74,900 Pending

  • Land
  • 4.31 Acres
  • $17,378 per Acre

  102 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

  102 Carriage Knoll Rd, Chester, NY 12817
• 

  $749,900 Sold Apr 18, 2025

  2 Grand View Terrace, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,480 Sq Ft
  • Built 2004

  Last Sold Summary

  • $215/SF
  • 29 Days On Market

  Current Estimated Value $732,408

  Last Listing Agent Randolph Rogers eXp Realty

  2 Grand View Terrace, Chester, NY 10918
• 

  Est $479,568 Not Listed For Sale

  30 Trotting Dr, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1968

  30 Trotting Dr, Chester, NY 10918

  Last Sold Summary

  • 5% Above List Price
  • $280/SF
  • 30 Days On Market

  Last Sold Price $455,000

  Last Listing Agent Christine Koenig Keller Williams Realty
• 

  

  /71

  $299,900 Pending

  • Land
  • 165.92 Acres
  • $1,807 per Acre

  L9 Atateka Rd, Chester, NY 12817

  This is a fantastic opportunity to own your own patch of beautiful Adirondack woods, nearly 166 acres, complete with a perennial stream, beaver pond, mature timber, and plenty of wild game. Use this property as your own recreational playground or build your dream home or camp in this peaceful, wooded retreat. Property is access by a right of way from Atateka Rd. Proceed ~400 feet to property line

  John O'Donnell Timberland Realty

  L9 Atateka Rd, Chester, NY 12817
• 

  $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 $596,550

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  114 Old Mansion Rd, Chester, NY 10918
• 

  Est $616,334 Not Listed For Sale

  38 Park Dr, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 2,770 Sq Ft
  • Built 1968

  38 Park Dr, Chester, NY 10918

  Last Sold Summary

  • 2% Above List Price
  • $218/SF
  • 28 Days On Market

  Last Sold Price $605,000

  Last Listing Agent Patricia Hyer Howard Hanna Rand Realty
• 

  $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 $756,952

  Last Listing Agent Moses Schreiber MS Realty Group USA, Inc

  56 Sunset Ridge Rd, Monroe, NY 10950

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