Chester, NY Homes

• 

  $610,000 Sold Aug 25, 2025

  411 Prospect Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,987 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Above List Price
  • $307/SF
  • 39 Days On Market

  Current Estimated Value $616,497

  Last Listing Agent Dana Posner Howard Hanna Rand Realty

  411 Prospect Rd, Chester, NY 10918
• 

  Est $784,515 Not Listed For Sale

  215 Ridge Rd, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 3,005 Sq Ft
  • Built 1848

  215 Ridge Rd, Chester, NY 10918

  Last Sold Summary

  • 1% Below List Price
  • $262/SF
  • 119 Days On Market

  • Last Sold Price $788,500
  • Dec 04, 2024

  Last Listing Agent Deborah Marks Keller Williams Realty
• 

  

  

  /24

  $362,900 Pending

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

  2203 Whispering Hills, Chester, NY 10918

  Welcome to 2203 Whispering Hills, Chester, NY — Where Comfort Meets ConvenienceThis sun-drenched end-unit townhome offers the perfect blend of space, style, and location in the sought-after Whispering Hills community.Featuring 3 spacious bedrooms and 2.5 bathrooms, this home is designed for both everyday comfort and effortless entertaining. The inviting living room is anchored by a cozy

  Marie Altieri Howard Hanna Rand Realty

  2203 Whispering Hills, Chester, NY 10918
• 

  $525,000 Sold Jul 24, 2025

  11 Vista Dr, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,122 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Above List Price
  • $247/SF
  • 43 Days On Market

  Current Estimated Value $555,276

  Last Listing Agent James Feldhaus eXp Realty

  11 Vista Dr, Chester, NY 10918
• 

  Est $507,923 Not Listed For Sale

  201 Hambletonian Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,342 Sq Ft
  • Built 1966

  201 Hambletonian Rd, Chester, NY 10918

  Last Sold Summary

  • 11% Above List Price
  • $340/SF
  • 19 Days On Market

  • Last Sold Price $456,000
  • Jun 29, 2023

  Last Listing Agent Kimberly Corkum Keller Williams Realty
• 

  

  /50

  $699,000 Open Sun 1:45PM - 2:45PM

  • 4 Beds
  • 2.5 Baths
  • 3,120 Sq Ft

  558 Pine Hill Rd, Chester, NY 10918

  Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

  Charnie Guttmann eRealty Advisors, Inc

  558 Pine Hill Rd, Chester, NY 10918
• 

  $415,000 Sold May 30, 2025

  18 Miller Dr, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Above List Price
  • $363/SF
  • 16 Days On Market

  Current Estimated Value $433,516

  Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  18 Miller Dr, Chester, NY 10918
• 

  Est $653,037 Not Listed For Sale

  16 Fernglade Ct, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 3,327 Sq Ft
  • Built 1973

  16 Fernglade Ct, Chester, NY 10918

  Last Sold Summary

  • 19% Above List Price
  • $165/SF
  • 12 Days On Market

  • Last Sold Price $550,000
  • Apr 23, 2025

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

  

  /50

  $715,000

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft

  17 Woodridge Dr, Chester, NY 10918

  Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4 years young. The pools heating system runs on propane tank. Entire home was freshly

  Sharon Kushner eXp Realty

  17 Woodridge Dr, Chester, NY 10918
• 

  $365,000 Sold Sep 12, 2025

  226 Eagleton Dr, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Below List Price
  • $215/SF
  • 16 Days On Market

  Current Estimated Value $382,481

  Last Listing Agent Lorrainne Pisciotta Weichert Realtors

  226 Eagleton Dr, Monroe, NY 10950
• 

  Est $743,458 Not Listed For Sale

  590 Craigville Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,152 Sq Ft
  • Built 2002

  590 Craigville Rd, Chester, NY 10918

  Last Sold Summary

  • 6% Above List Price
  • $222/SF
  • 26 Days On Market

  • Last Sold Price $699,000
  • Aug 01, 2024

  Last Listing Agent Lazar Schvimmer Blooming Realty
• 

  

  /49

  $735,000

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  55 Beverly Rd, Chester, NY 10918

  Welcome to 55 Beverly Road, Chester—A Stunning, Move-In Ready Home This beautifully updated 3,156 square-foot home blends timeless charm with modern upgrades, offering space, comfort, and style throughout. The expansive floor plan features bright, inviting living areas with soaring vaulted ceilings, gleaming hardwood floors throughout, and a cozy masonry fireplace that serves as a perfect focal

  Jay Himelson Howard Hanna Rand Realty

  55 Beverly Rd, Chester, NY 10918
• 

  $475,000 Sold May 15, 2025

  11 N Hudson St Unit N, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1956

  Last Sold Summary

  • 11% Above List Price
  • $317/SF
  • 22 Days On Market

  Current Estimated Value $472,346

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center

  11 N Hudson St Unit N, Chester, NY 10918
• 

  Est $613,307 Not Listed For Sale

  13 Townsend Place, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft
  • Built 1969

  13 Townsend Place, Chester, NY 10918

  Last Sold Summary

  • 5% Above List Price
  • $188/SF
  • 25 Days On Market

  • Last Sold Price $585,000
  • Jul 29, 2024

  Last Listing Agent Hershel Mittelman The Middleman Team
• 

  

  /41

  $569,000

  • 4 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  78 Pickerel Rd, Monroe, NY 10950

  Beautiful and spacious 4 Bedroom, 2.5 Bath Colonial set on park-like property in a lovely neighborhood with a serene backdrop of mature trees, offering both privacy and a peaceful setting. This home features a large eat-in kitchen with abundant cabinetry, tremendous counter space, and a sliding glass door leading to a newer rear deck—perfect for relaxing or entertaining outdoors.The oversized

  Mary Ann Mitchell eXp Realty

  78 Pickerel Rd, Monroe, NY 10950
• 

  $869,000 Sold Jul 24, 2025

  26 W Meadow Way, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 3,100 Sq Ft
  • Built 2024

  Last Sold Summary

  • 3% Below List Price
  • $280/SF
  • 85 Days On Market

  Current Estimated Value $118,000

  Last Listing Agent Nancy Sardo BHG Real Estate Green Team

  26 W Meadow Way, Chester, NY 10918
• 

  Est $520,716 Not Listed For Sale

  11 Townsend Place, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,788 Sq Ft
  • Built 1968

  11 Townsend Place, Chester, NY 10918

  Last Sold Summary

  • 1% Below List Price
  • $294/SF
  • 28 Days On Market

  • Last Sold Price $525,000
  • Dec 10, 2024

  Last Listing Agent Lora Juncaj BHG Real Estate Green Team
• 

  

  /30

  $550,000

  • 5 Beds
  • 2.5 Baths
  • 1,815 Sq Ft

  208 Glenmere Rd, Chester, NY 10918

  Welcome to 208 Glenmere Rd, Chester, NY! This charming country home, nestled on picturesque grounds, is now available for sale. The main level features an eat-in kitchen, a formal dining room, and two spacious bedrooms, while the upper level offers three additional bedrooms. The newly renovated cottage boasts new flooring, windows, kitchen, and heating system. The interior has been freshly

  David Kraus MK Realty Inc

  208 Glenmere Rd, Chester, NY 10918
• 

  $100,000 Sold Feb 12, 2026

  0 Renies Rd, Chester, NY 10918

  • Land
  • 1.85 Acres
  • $54,054 per Acre

  Last Sold Summary

  • 50% Below List Price
  • 102 Days On Market

  Last Listing Agent Kristie Jacques Century 21 Full Service Realty

  0 Renies Rd, Chester, NY 10918
• 

  Est $643,204 Not Listed For Sale

  509 Laroe Rd, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft
  • Built 1981

  509 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 12% Above List Price
  • $245/SF
  • 50 Days On Market

  • Last Sold Price $575,000
  • Feb 08, 2024

  Last Listing Agent Bridget Wallace Howard Hanna Rand Realty
• 

  

  /38

  $635,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  25 Sugarloaf Mountain Rd, Chester, NY 10918

  MONROE WOODBURY SCHOOLS! BRAND NEW KITCHEN! ABSOLUTE MUST SEE!Welcome to your dream home in the highly sought-after Monroe Woodbury School District. Privately set at the end of a long driveway on just under one acre, this beautifully renovated Colonial offers an incredible balance of peace, privacy, and recent upgrades.From the moment you step inside, you are greeted by a stunning foyer that

  Frank Muccari Cronin & Company Real Estate

  25 Sugarloaf Mountain Rd, Chester, NY 10918
• 

  $525,000 Sold Sep 02, 2025

  10 Tulip Ln, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • Built 1961

  Last Sold Summary

  • 3% Below List Price
  • $299/SF
  • 38 Days On Market

  Current Estimated Value $536,967

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  10 Tulip Ln, Monroe, NY 10950
• 

  Est $635,741 Not Listed For Sale

  16 Bianca Blvd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,192 Sq Ft
  • Built 1987

  16 Bianca Blvd, Chester, NY 10918

  Last Sold Summary

  • 6% Above List Price
  • $188/SF
  • 21 Days On Market

  • Last Sold Price $600,000
  • Oct 04, 2024

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group
• 

  

  /38

  $565,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,846 Sq Ft

  52 Wilson Rd, Monroe, NY 10950

  Welcome to this beautifully maintained 4-bedroom, 3-bath raised ranch in the highly sought-after Lake Hill Farms community, located within the Monroe-Woodbury School District.Upon entry, you’re greeted by an oversized foyer featuring wide stairs updated with stunning hardwood that runs throughout. The main level offers a bright eat-in kitchen with sliding glass doors that open to a deck

  Claudia Lepore Keller Williams Realty

  52 Wilson Rd, Monroe, NY 10950
• 

  $655,000 Sold Feb 18, 2026

  3 Derose Ln, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 2,550 Sq Ft
  • Built 1997

  Last Sold Summary

  • 1% Above List Price
  • $257/SF
  • 44 Days On Market

  Current Estimated Value $649,508

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  3 Derose Ln, Chester, NY 10918
• 

  Est $668,215 Not Listed For Sale

  142 Laroe Rd, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 3,385 Sq Ft
  • Built 1981

  142 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 10% Above List Price
  • $180/SF
  • 107 Days On Market

  • Last Sold Price $607,700
  • Apr 29, 2025

  Last Listing Agent Peter Persaud HomeSmart Homes & Estates
• 

  

  /5

  $54,900

  • Land
  • 10.14 Acres
  • $5,414 per Acre

  15 Deer Run, Chester, NY 12817

  10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

  Patricia Seitz McAlonen Pearsall Realty

  15 Deer Run, Chester, NY 12817
• 

  

  /39

  $579,000 Sold Jun 12, 2025

  2754 Schroon River Rd, Chester, NY 12817

  • 3 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • Built 1989

  Last Sold Summary

  • $348/SF
  • 8 Days On Market

  Last Listing Agent Angie Mead Gallo Realty ADK Inc

  2754 Schroon River Rd, Chester, NY 12817
• 

  Est $697,855 Not Listed For Sale

  3 Overlook Trail, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 1985

  3 Overlook Trail, Chester, NY 10918

  Last Sold Summary

  • 12% Above List Price
  • $241/SF
  • 35 Days On Market

  • Last Sold Price $625,000
  • Sep 14, 2023

  Last Listing Agent Robert Addon Keller Williams Realty
• 

  

  /49

  $635,000

  • 5 Beds
  • 3 Baths
  • 2,983 Sq Ft

  9 Mount Ridge Ct, Monroe, NY 10950

  Spacious Center Hall Colonial with open concept kitchen, fireplace, deck, and large primary suite with walk-in closets. A dramatic two-story entry leads to an open concept kitchen with abundant counter space, large dinette area, and sliding doors to a spacious deck --perfect for entertaining. The kitchen flows into the open family room and living room with fireplace, creating an ideal setup for

  Richard Froehlich RE/MAX Benchmark Realty Group

  9 Mount Ridge Ct, Monroe, NY 10950
• 

  

  /13

  $300,000 Sold Dec 23, 2025

  68 Walter Foote Rd, Chester, NY 12853

  • Land
  • 194 Acres
  • $1,546 per Acre

  Last Sold Summary

  • 52% Below List Price
  • 86 Days On Market

  Last Listing Agent Cindy Brower Coldwell Banker Prime Properties

  68 Walter Foote Rd, Chester, NY 12853
• 

  Est $1,138,000 Not Listed For Sale

  282 Laroe Rd, Chester, NY 10918

  • 6 Beds
  • 5 Baths
  • 6,622 Sq Ft
  • Built 1900

  282 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 6% Above List Price
  • $162/SF
  • 112 Days On Market

  • Last Sold Price $1,075,000
  • Nov 20, 2024

  Last Listing Agent Jacob Matthews Ellis Sotheby's Intl Realty
• 

  /2

  $1,299,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 5,712 Sq Ft

  16 Sunset Ridge, Monroe, NY 10950

  Secluded Trout Brook Estate: Expansive 5,700+ Sq Ft ready for Multi-Gen Living and Entertaining. Nestled on nearly six private acres in the exclusive Trout Brook Estates Community, this expansive Colonial-style estate delivers classic elegance with modern comfort. Built in 1993 and thoughtfully designed for multi-generational living and refined entertaining, this home offers generous spaces, lush

  Carmela Lopez Borrazas Serhant LLC

  16 Sunset Ridge, Monroe, NY 10950
• 

  $829,000 Sold May 12, 2025

  30 Meadow Ave, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • Built 2024

  Last Sold Summary

  • $307/SF
  • 85 Days On Market

  Last Listing Agent Nancy Sardo BHG Real Estate Green Team

  30 Meadow Ave, Chester, NY 10918
• 

  Est $572,512 Not Listed For Sale

  412 Laroe Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1995

  412 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 1% Below List Price
  • $313/SF
  • 19 Days On Market

  • Last Sold Price $579,000
  • Dec 05, 2024

  Last Listing Agent Teresa Gavan BHG Real Estate Green Team
• 

  

  /23

  $68,900

  • Land
  • 3.11 Acres
  • $22,154 per Acre

  72 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

  72 Carriage Knoll Rd, Chester, NY 12817
• 

  $125,000 Sold Oct 03, 2025

  0 William Hill Rd, Chester, NY 12817

  • Land
  • 45.83 Acres
  • $2,727 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 99 Days On Market

  Last Listing Agent Jason Minch William Raveis-New York LLC

  0 William Hill Rd, Chester, NY 12817
• 

  Est $746,137 Not Listed For Sale

  76 Restdale Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,838 Sq Ft
  • Built 1997

  76 Restdale Rd, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $252/SF
  • 20 Days On Market

  • Last Sold Price $715,000
  • Apr 01, 2025

  Last Listing Agent Philip Szumlaski Keller Williams Realty
• 

  

  /22

  $738,850 Pending

  • Land
  • 561.54 Acres
  • $1,316 per Acre

  234 Old River Rd, Chester, NY 12853

  This property is 562 Ac of Adk field and forest with 2,000 ft. of frontage on the Hudson River, 2 beaver ponds, stream and trails. Structures on this dormant farm include an uninhabited house, barn and shed in need of rehab. An authentic log cabin is situated at a higher elevation above the field, beside an active beaver pond. Adjacent is a 'Morton' building, ideal for storage of equipment and

  John O'Donnell Timberland Realty

  234 Old River Rd, Chester, NY 12853
• 

  $617,000 Sold May 19, 2025

  1301 Kings Hwy, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft
  • Built 1835

  Last Sold Summary

  • 10% Below List Price
  • $231/SF
  • 146 Days On Market

  Current Estimated Value $645,589

  Last Listing Agent Susan Walski HomeSmart Homes & Estates

  1301 Kings Hwy, Chester, NY 10918

Showing Results 81 - 120, Page 3 of 18