6,812

Chester, NY Homes

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  • 411 Prospect Rd, Chester, NY 10918

    $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 $594,859

    Last Listing Agent Dana Posner Howard Hanna Rand Realty

    411 Prospect Rd, Chester, NY 10918
    • 11 Townsend Place, Chester, NY 10918

      Est $524,137 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

      • $294/SF
      • 28 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Lora Juncaj BHG Real Estate Green Team

  • 70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    /23

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 1,357 Sq Ft

    70 Main St, Chester, NY 10918

    Discover the perfect blend of versatility and charm with this exceptional property. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn extends your options with beautifully finished space that carries rustic character alongside modern updates. Whether you

    Kassandra Mott Keller Williams Hudson Valley

    70 Main St, Chester, NY 10918
  • 11 Vista Dr, 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 $540,587

    Last Listing Agent James Feldhaus eXp Realty

    11 Vista Dr, Chester, NY 10918
    • 509 Laroe Rd, Chester, NY 10918

      Est $642,585 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

      Last Listing Agent Bridget Wallace Howard Hanna Rand Realty

  • 234 Old River Rd, Chester, NY 12853
    234 Old River Rd, Chester, NY 12853
    234 Old River Rd, Chester, NY 12853
    /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
  • 18 Miller Dr, 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 $415,432

    Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

    18 Miller Dr, Chester, NY 10918
    • 16 Bianca Blvd, Chester, NY 10918

      Est $642,320 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

      • 7% Above List Price
      • $188/SF
      • 21 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  • 71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    /17

    $59,900

    • Land
    • 1.89 Acres
    • $31,693 per Acre

    71 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

    71 Carriage Knoll Rd, Chester, NY 12817
  • 226 Eagleton Dr, Monroe, NY 10950

    $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 $369,737

    Last Listing Agent Lorrainne Pisciotta Weichert Realtors

    226 Eagleton Dr, Monroe, NY 10950
    • 3 Overlook Trail, Chester, NY 10918

      Est $698,343 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

      Last Listing Agent Robert Addon Keller Williams Realty

  • 16 Oakland Ave, Chester, NY 10918
    16 Oakland Ave, Chester, NY 10918
    16 Oakland Ave, Chester, NY 10918
    /49

    $425,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,090 Sq Ft

    16 Oakland Ave, Chester, NY 10918

    .

    Vikki Garby BHG Real Estate Green Team

    16 Oakland Ave, Chester, NY 10918
  • 11 N Hudson St Unit N, 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 $449,980

    Last Listing Agent Layla Rose Boyles Century 21 Realty Center

    11 N Hudson St Unit N, Chester, NY 10918
    • 109 Restdale Rd, Chester, NY 10918

      Est $760,011 Not Listed For Sale

      109 Restdale Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 3,422 Sq Ft
      • Built 2001
      109 Restdale Rd, Chester, NY 10918

      Last Sold Summary

      • 16% Above List Price
      • $191/SF
      • 22 Days On Market

      Last Sold Price $655,000

      Last Listing Agent Philip Szumlaski Keller Williams Realty

  • 32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    /5

    $259,000

    • Land
    • 20.18 Acres
    • $12,834 per Acre

    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 can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! .... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with

    Karen Gauvin Our House Real Estate Group

    32 Mountainside Dr, Chester, NY 10918
  • 3 Sunset Ridge Rd, Monroe, NY 10950

    $701,000 Sold Apr 01, 2025

    3 Sunset Ridge Rd, Monroe, NY 10950

    • 4 Beds
    • 3.5 Baths
    • 3,524 Sq Ft
    • Built 1996

    Last Sold Summary

    • $199/SF
    • 94 Days On Market

    Current Estimated Value $730,582

    Last Listing Agent Nicholas Cuomo Keller Williams Realty

    3 Sunset Ridge Rd, Monroe, NY 10950
    • 282 Laroe Rd, Chester, NY 10918

      Est $1,167,000 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

      • 9% Above List Price
      • $162/SF
      • 112 Days On Market

      Last Sold Price $1,075,000

      Last Listing Agent Jacob Matthews Ellis Sotheby's Intl Realty

  • 2113 Whispering Hills Unit 178, Chester, NY 10918
    2113 Whispering Hills Unit 178, Chester, NY 10918
    2113 Whispering Hills Unit 178, Chester, NY 10918
    /24

    $275,000

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

    2113 Whispering Hills Unit 178, Chester, NY 10918

    Welcome Home! 2 Bedrooms 1 Bathroom move in ready end unit. Recently renovated including a new kitchen with granite counter tops and stainless steel appliances, new bathroom, new windows, new laminate flooring, new water heater, new light fixtures and recessed lighting. Nothing to do but move in! Close to supermarket, post office, restaurants, urgent care, highway. Perfect commuter location.

    Valerie Quinn Keller Williams Realty

    2113 Whispering Hills Unit 178, Chester, NY 10918
  • 26 W Meadow Way, Chester, NY 10918

    $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 $121,064

    Last Listing Agent Nancy Sardo BHG Real Estate Green Team

    26 W Meadow Way, Chester, NY 10918
    • 412 Laroe Rd, Chester, NY 10918

      Est $575,051 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

      Last Listing Agent Teresa Gavan BHG Real Estate Green Team

  • 77 Carriage Knoll Rd, Chester, NY 12817
    77 Carriage Knoll Rd, Chester, NY 12817
    77 Carriage Knoll Rd, Chester, NY 12817
    /19

    $74,900

    • Land
    • 4.17 Acres
    • $17,962 per Acre

    77 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

    77 Carriage Knoll Rd, Chester, NY 12817
  • 0 Renies 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
    • 53 Elvis Blvd, Chester, NY 10918

      Est $690,031 Not Listed For Sale

      53 Elvis Blvd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,838 Sq Ft
      • Built 1999
      53 Elvis Blvd, Chester, NY 10918

      Last Sold Summary

      • 15% Above List Price
      • $211/SF
      • 39 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  • 31 Hudson St, Chester, NY 10918
    31 Hudson St, Chester, NY 10918
    31 Hudson St, Chester, NY 10918
    /25

    $449,900

    • 2 Beds
    • 2 Baths
    • 1,998 Sq Ft

    31 Hudson St, Chester, NY 10918

    Set on nearly half an acre in the Village of Chester, this charming brick Cape Cod offers a rare combination of privacy and convenience, featuring a flexible four room layout and a fully finished lower level with full bath. Positioned well back from the road with a long private driveway and no homes directly across the street, the setting feels peaceful and tucked away while remaining minutes

    Geoffrey Green BHG Real Estate Green Team

    31 Hudson St, Chester, NY 10918
  • 10 Tulip Ln, Monroe, NY 10950

    $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 $525,906

    Last Listing Agent Philip Szumlaski Keller Williams Realty

    10 Tulip Ln, Monroe, NY 10950
    • 40 Valley View Dr, Chester, NY 10918

      Est $690,686 Not Listed For Sale

      40 Valley View Dr, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 3,308 Sq Ft
      • Built 2000
      40 Valley View Dr, Chester, NY 10918

      Last Sold Summary

      • 27% Above List Price
      • $165/SF
      • 34 Days On Market

      Last Sold Price $545,000

      Last Listing Agent Ammar Iqbal eXp Realty

  • 62 Carriage Knolls Rd, Chester, NY 12817
    62 Carriage Knolls Rd, Chester, NY 12817
    62 Carriage Knolls Rd, Chester, NY 12817
    /23

    $62,000

    • Land
    • 11.11 Acres
    • $5,581 per Acre

    62 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

    62 Carriage Knolls Rd, Chester, NY 12817
  • 3 Derose Ln, Chester, NY 10918

    $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 $648,174

    Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

    3 Derose Ln, Chester, NY 10918
    • 47 Valley View Dr, Chester, NY 10918

      Est $749,699 Not Listed For Sale

      47 Valley View Dr, Chester, NY 10918

      • 5 Beds
      • 3.5 Baths
      • 3,812 Sq Ft
      • Built 1998
      47 Valley View Dr, Chester, NY 10918

      Last Sold Summary

      • 7% Above List Price
      • $183/SF
      • 72 Days On Market

      Last Sold Price $699,000

      Last Listing Agent Claudia Lepore Keller Williams Realty

  • 503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    /13

    $239,900

    • 2 Beds
    • 1.5 Baths
    • 1,240 Sq Ft

    503 Mountain Laurel Dr, Monroe, NY 10950

    Peaceful country living in this two-story center lakefront unit with full basement located in Windridge community. Enjoy incredible mountain views from this large private Townhome. Primary bedroom on upper level with walk in closet and large sitting area which can be used as home office. Slider to rear patio with beautiful lake views!! Large living and dining area. Beautiful quiet complex close

    Margaret Galatro ARC Realty 1 in Sales

    503 Mountain Laurel Dr, Monroe, NY 10950
  • 2754 Schroon River Rd, Chester, NY 12817
    2754 Schroon River Rd, Chester, NY 12817
    2754 Schroon River Rd, 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
    • 121 Conklingtown Rd, Chester, NY 10918

      Est $705,756 Not Listed For Sale

      121 Conklingtown Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,599 Sq Ft
      • Built 2000
      121 Conklingtown Rd, Chester, NY 10918

      Last Sold Summary

      • 2% Above List Price
      • $265/SF
      • 22 Days On Market

      Last Sold Price $690,000

      Last Listing Agent Joel Basch eRealty Advisors, Inc

  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    /23

    $400,000

    • 3 Beds
    • 1 Bath
    • 1,561 Sq Ft

    33 Meadow Ave, Chester, NY 10918

    One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

    Ernie Acampora River Realty Services, Inc.

    33 Meadow Ave, Chester, NY 10918
  • 68 Walter Foote Rd, Chester, NY 12853
    68 Walter Foote Rd, Chester, NY 12853
    68 Walter Foote Rd, Chester, NY 12853
    /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
    • 79 Conklingtown Rd, Chester, NY 10918

      Est $608,554 Not Listed For Sale

      79 Conklingtown Rd, Chester, NY 10918

      • 4 Beds
      • 3 Baths
      • 2,636 Sq Ft
      • Built 1988
      79 Conklingtown Rd, Chester, NY 10918

      Last Sold Summary

      • 10% Above List Price
      • $211/SF
      • 13 Days On Market

      Last Sold Price $555,000

      Last Listing Agent David Katina ESTMAX REALTY

  • 20 Carriage Knolls Rd, Chester, NY 12817
    20 Carriage Knolls Rd, Chester, NY 12817
    20 Carriage Knolls Rd, Chester, NY 12817
    /7

    $49,500

    • Land
    • 3.36 Acres
    • $14,732 per Acre

    20 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

    20 Carriage Knolls Rd, Chester, NY 12817
  • 30 Meadow Ave, Chester, NY 10918

    $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
    • 70 Conklingtown Rd, Chester, NY 10918

      Est $348,557 Not Listed For Sale

      70 Conklingtown Rd, Chester, NY 10918

      • 3 Beds
      • 1 Bath
      • 835 Sq Ft
      • Built 1945
      70 Conklingtown Rd, Chester, NY 10918

      Last Sold Summary

      • 11% Above List Price
      • $377/SF
      • 22 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Moses Roth Blooming Realty

  • L2 Friends Lake Rd, Chester, NY 12817
    L2 Friends Lake Rd, Chester, NY 12817
    L2 Friends Lake Rd, Chester, NY 12817
    /20

    $169,500 Pending

    • Land
    • 22.6 Acres
    • $7,500 per Acre

    L2 Friends Lake Rd, Chester, NY 12817

    Seller financing now available with decent deposit and good credit. Previously approved 4-lot subdivision with beach rights to Murphy Beach on Friends Lake. 8.6 acre lot, 7.5 acre lot, 3.2 acre lot, and a 3 acre lot. Rough house and septic locations have been approved. (reference survey map) Possible views from the upper areas of the property with some select clearing. Make arrangements to walk

    Walter Swartz Gallo Realty ADK Inc

    L2 Friends Lake Rd, Chester, NY 12817
  • 16 Kerner Dr, Chester, NY 10918

    $405,000 Sold Apr 30, 2025

    16 Kerner Dr, Chester, NY 10918

    • 3 Beds
    • 1 Bath
    • 1,222 Sq Ft
    • Built 1962

    Last Sold Summary

    • 9% Above List Price
    • $331/SF
    • 35 Days On Market

    Current Estimated Value $404,656

    Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

    16 Kerner Dr, Chester, NY 10918

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