6,821

Chester, NY Homes

Section Image
    • 53 Elvis Blvd, Chester, NY 10918

      Est $715,250 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

      • 19% Above List Price
      • $211/SF
      • 39 Days On Market
      • Last Sold Price $600,000
      • Oct 06, 2023

      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
  • 219 Bull Mill Rd, Chester, NY 10918

    $535,000 Sold Feb 09, 2026

    219 Bull Mill Rd, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Above List Price
    • $277/SF
    • 36 Days On Market

    Current Estimated Value $531,998

    Last Listing Agent Claudia Lepore Keller Williams Realty

    219 Bull Mill Rd, Chester, NY 10918
    • 40 Valley View Dr, Chester, NY 10918

      Est $713,119 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

      • 31% Above List Price
      • $165/SF
      • 34 Days On Market
      • Last Sold Price $545,000
      • May 18, 2023

      Last Listing Agent Ammar Iqbal eXp 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
  • 354 Rande Rd Unit 354, Monroe, NY 10950

    $419,999 Sold Jan 07, 2026

    354 Rande Rd Unit 354, Monroe, NY 10950

    • 3 Beds
    • 2.5 Baths
    • 1,698 Sq Ft
    • Built 1999

    Last Sold Summary

    • $247/SF
    • 28 Days On Market

    Current Estimated Value $422,145

    Last Listing Agent Joel Ayala HomeSmart Homes & Estates

    354 Rande Rd Unit 354, Monroe, NY 10950
    • 47 Valley View Dr, Chester, NY 10918

      Est $742,415 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

      • 6% Above List Price
      • $183/SF
      • 72 Days On Market
      • Last Sold Price $699,000
      • Sep 13, 2024

      Last Listing Agent Claudia Lepore Keller Williams 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 Pending

    • 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
  • 3 Woodridge Dr, Chester, NY 10918

    $763,750 Sold Jun 20, 2025

    3 Woodridge Dr, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 1995

    Last Sold Summary

    • 4% Below List Price
    • $306/SF
    • 69 Days On Market

    Current Estimated Value $766,597

    Last Listing Agent Gina Dudgeon Howard Hanna Rand Realty

    3 Woodridge Dr, Chester, NY 10918
    • 121 Conklingtown Rd, Chester, NY 10918

      Est $727,664 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

      • 5% Above List Price
      • $265/SF
      • 22 Days On Market
      • Last Sold Price $690,000
      • Nov 12, 2024

      Last Listing Agent Joel Basch eRealty Advisors, Inc

  • 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
  • 19 Taurus Ave, Monroe, NY 10950

    $389,000 Sold Jul 09, 2025

    19 Taurus Ave, Monroe, NY 10950

    • 3 Beds
    • 1.5 Baths
    • 1,288 Sq Ft
    • Built 1954

    Last Sold Summary

    • 4% Above List Price
    • $302/SF
    • 30 Days On Market

    Current Estimated Value $388,594

    Last Listing Agent Christian Baez Keller Williams Hudson Valley

    19 Taurus Ave, Monroe, NY 10950
    • 79 Conklingtown Rd, Chester, NY 10918

      Est $630,689 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

      • 14% Above List Price
      • $211/SF
      • 13 Days On Market
      • Last Sold Price $555,000
      • Nov 15, 2024

      Last Listing Agent David Katina ESTMAX REALTY

  • 4 Oak St, Chester, NY 10918
    4 Oak St, Chester, NY 10918
    4 Oak St, Chester, NY 10918
    /42

    $499,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft

    4 Oak St, Chester, NY 10918

    SPRAWLING BRICK RANCH!!! VILLAGE OF CHESTER! ALMOST 1900 SQ. FT. ON THE MAIN LEVEL!!! X- LARGE 1/2 ACRE LOT!!! Welcome to 4 Oak Street, nestled in the charming Village of Chester, NY. Offered for the very first time, this exceptional home was custom built for its original owners and has been lovingly maintained ever since—a true testament to quality craftsmanship and pride of ownership. Set on a

    Frank Muccari Cronin & Company Real Estate

    4 Oak St, Chester, NY 10918
  • 116 Carriage Knoll Rd, Chester, NY 12817
    116 Carriage Knoll Rd, Chester, NY 12817
    116 Carriage Knoll Rd, Chester, NY 12817
    /16

    $60,000 Sold Jun 12, 2025

    116 Carriage Knoll Rd, Chester, NY 12817

    • Land
    • 5.34 Acres
    • $11,236 per Acre

    Last Sold Summary

    • 4% Below List Price
    • 30 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    116 Carriage Knoll Rd, Chester, NY 12817
    • 70 Conklingtown Rd, Chester, NY 10918

      Est $351,048 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
      • Jan 05, 2024

      Last Listing Agent Moses Roth Blooming Realty

  • 145 Kings Highway Bypass, Chester, NY 10918
    145 Kings Highway Bypass, Chester, NY 10918
    145 Kings Highway Bypass, Chester, NY 10918
    /50

    $1,450,000

    • 4 Beds
    • 4 Baths
    • 4,508 Sq Ft

    145 Kings Highway Bypass, Chester, NY 10918

    Set gracefully on 3.8 private acres within the highly coveted Warwick School District, this exceptional custom home offers a rare blend of architectural elegance and refined living. Surrounded by a collection of equally distinguished residences, the property provides an expansive, park-like sanctuary while remaining nestled in the heart of one of the region’s most sought-after communities.

    Courtney Tablante Keller Williams Realty

    145 Kings Highway Bypass, Chester, NY 10918
  • 507 Bull Mill Rd, Chester, NY 10918

    $675,000 Sold Feb 18, 2026

    507 Bull Mill Rd, Chester, NY 10918

    • 5 Beds
    • 2.5 Baths
    • 3,115 Sq Ft
    • Built 2003

    Last Sold Summary

    • 4% Below List Price
    • $217/SF
    • 134 Days On Market

    Current Estimated Value $699,976

    Last Listing Agent Alison Orlando Keller Williams Hudson Valley

    507 Bull Mill Rd, Chester, NY 10918
    • 3976 Summerville Way, Chester, NY 10918

      Est $515,586 Not Listed For Sale

      3976 Summerville Way, Chester, NY 10918

      • 3 Beds
      • 1.5 Baths
      • 1,474 Sq Ft
      • Built 1955
      3976 Summerville Way, Chester, NY 10918

      Last Sold Summary

      • 2% Below List Price
      • $357/SF
      • 32 Days On Market
      • Last Sold Price $526,000
      • Dec 11, 2024

      Last Listing Agent David Kraus MK Realty Inc

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

    $449,900 Pending

    • 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
  • 3 Grant Dr, Monroe, NY 10950

    $530,000 Sold May 19, 2025

    3 Grant Dr, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft
    • Built 1989

    Last Sold Summary

    • 6% Above List Price
    • $274/SF
    • 21 Days On Market

    Current Estimated Value $554,933

    Last Listing Agent Rosalie Cook Weichert Realtors

    3 Grant Dr, Monroe, NY 10950
    • 3966 Summerville Way, Chester, NY 10918

      Est $753,000 Not Listed For Sale

      3966 Summerville Way, Chester, NY 10918

      • 5 Beds
      • 3 Baths
      • 2,882 Sq Ft
      • Built 1945
      3966 Summerville Way, Chester, NY 10918

      Last Sold Summary

      • 12% Above List Price
      • $232/SF
      • 6 Days On Market
      • Last Sold Price $670,000
      • Aug 22, 2024

      Last Listing Agent Leon Klein Keller Williams Hudson Valley

  • 19 High St, Chester, NY 10918
    19 High St, Chester, NY 10918
    19 High St, Chester, NY 10918
    /50

    $1,195,000

    • 9 Beds
    • 6.5 Baths
    • 4,965 Sq Ft

    19 High St, Chester, NY 10918

    Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

    Beth Palma Keller Williams Realty

    19 High St, Chester, NY 10918
  • L2 Friends Lake Rd, Chester, NY 12817
    L2 Friends Lake Rd, Chester, NY 12817
    L2 Friends Lake Rd, Chester, NY 12817
    /20

    $155,000 Sold Apr 01, 2026

    L2 Friends Lake Rd, Chester, NY 12817

    • Land
    • 22.6 Acres
    • $6,858 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 607 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    L2 Friends Lake Rd, Chester, NY 12817
    • 1689 Kings Hwy, Chester, NY 10918

      Est $761,303 Not Listed For Sale

      1689 Kings Hwy, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,682 Sq Ft
      • Built 1999
      1689 Kings Hwy, Chester, NY 10918

      Last Sold Summary

      • 14% Above List Price
      • $248/SF
      • 158 Days On Market
      • Last Sold Price $665,000
      • Dec 20, 2023

      Last Listing Agent Rita Geissler ARC Realty 1 in Sales

  • 5 N Hudson St Unit N, Chester, NY 10918
    5 N Hudson St Unit N, Chester, NY 10918
    5 N Hudson St Unit N, Chester, NY 10918
    /28

    $500,000

    • 3 Beds
    • 2 Baths
    • 2,688 Sq Ft

    5 N Hudson St Unit N, Chester, NY 10918

    3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.

    Bernadette Corrigan Keller Williams Realty

    5 N Hudson St Unit N, Chester, NY 10918
  • 10 Spectrum Dr, Chester, NY 10918

    $800,000 Sold Sep 15, 2025

    10 Spectrum Dr, Chester, NY 10918

    • 5 Beds
    • 4 Baths
    • 4,496 Sq Ft
    • Built 1991

    Last Sold Summary

    • 11% Below List Price
    • $178/SF
    • 24 Days On Market

    Current Estimated Value $832,231

    Last Listing Agent David Hopstein eRealty Advisors, Inc

    10 Spectrum Dr, Chester, NY 10918
    • 128 Booth Rd, Chester, NY 10918

      Est $557,482 Not Listed For Sale

      128 Booth Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,102 Sq Ft
      • Built 1975
      128 Booth Rd, Chester, NY 10918

      Last Sold Summary

      • 2% Above List Price
      • $259/SF
      • 179 Days On Market
      • Last Sold Price $545,000
      • Jan 17, 2025

      Last Listing Agent Tracy McNamara Keller Williams 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
  • L47 Cobble Creek Rd, Chester, NY 12853
    L47 Cobble Creek Rd, Chester, NY 12853
    L47 Cobble Creek Rd, Chester, NY 12853
    /12

    $189,500 Sold Jun 02, 2025

    L47 Cobble Creek Rd, Chester, NY 12853

    • Land
    • 97.28 Acres
    • $1,948 per Acre

    Last Sold Summary

    • 5% Below List Price
    • 11 Days On Market

    Last Listing Agent Sara Gallipo-Sammis Century 21 - Adirondacks

    L47 Cobble Creek Rd, Chester, NY 12853
    • 272 Bull Mill Rd, Chester, NY 10918

      Est $675,179 Not Listed For Sale

      272 Bull Mill Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,504 Sq Ft
      • Built 1998
      272 Bull Mill Rd, Chester, NY 10918

      Last Sold Summary

      • 13% Above List Price
      • $240/SF
      • 50 Days On Market
      • Last Sold Price $600,000
      • Jul 18, 2023

      Last Listing Agent Joseph Rosenfeld Flag Realty Group

  • 151 Laroe Rd, Chester, NY 10918
    151 Laroe Rd, Chester, NY 10918
    151 Laroe Rd, Chester, NY 10918
    /43

    $450,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,177 Sq Ft

    151 Laroe Rd, Chester, NY 10918

    What a remarkable property in the town of Chester, NY-a highly sought after town in the southern Hudson Valley, only 45 minutes from the GW Bridge! This 3 bedroom, 2 bathroom house boasts tons of modern and energy efficient features. A massive renovation done only 5 years ago leaves you with nothing to maintain except to pick your paint colors and finishes. 1st floor main bedroom and additional

    Todd Sullivan Keller Williams Realty

    151 Laroe Rd, Chester, NY 10918
  • 13 Tulip Ln Unit 4, Monroe, NY 10950

    $555,000 Sold Sep 18, 2025

    13 Tulip Ln Unit 4, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 1,844 Sq Ft
    • Built 1960

    Last Sold Summary

    • 1% Above List Price
    • $301/SF
    • 87 Days On Market

    Current Estimated Value $555,442

    Last Listing Agent Courtney Tablante Keller Williams Realty

    13 Tulip Ln Unit 4, Monroe, NY 10950
    • 71 Winding Trail, Chester, NY 10918

      Est $672,269 Not Listed For Sale

      71 Winding Trail, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,800 Sq Ft
      • Built 1987
      71 Winding Trail, Chester, NY 10918

      Last Sold Summary

      • $239/SF
      • 10 Days On Market
      • Last Sold Price $670,000
      • May 14, 2024

      Last Listing Agent Frank Muccari Cronin & Company Real Estate

  • L3 Emily Ln Unit Lot 3, Chester, NY 12817
    L3 Emily Ln Unit Lot 3, Chester, NY 12817
    L3 Emily Ln Unit Lot 3, Chester, NY 12817
    /24

    $165,000

    • Land
    • 31,798 Sq Ft
    • $226,027 per Acre

    L3 Emily Ln Unit Lot 3, Chester, NY 12817

    Rare opportunity to own a .73-acre vacant building lot with deeded dock and lake rights on beautiful Loon Lake. Located within the small and intimate Lakemont Association--featuring just 8 members--this property offers a unique chance to secure one of the few lake rights parcels with guaranteed docking. The lot is level and has already undergone selective clearing, making it an ideal canvas for

    Saraha Millington Gallo Realty ADK Inc

    L3 Emily Ln Unit Lot 3, Chester, NY 12817
  • 65 Hudson St, Chester, NY 10918

    $305,000 Sold Feb 20, 2026

    65 Hudson St, Chester, NY 10918

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1930

    Last Sold Summary

    • 12% Below List Price
    • $272/SF
    • 57 Days On Market

    Current Estimated Value $313,271

    Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

    65 Hudson St, Chester, NY 10918
    • 11 Park Place, Chester, NY 10918

      Est $783,928 Not Listed For Sale

      11 Park Place, Chester, NY 10918

      • 5 Beds
      • 3.5 Baths
      • 2,923 Sq Ft
      • Built 1996
      11 Park Place, Chester, NY 10918

      Last Sold Summary

      • 12% Above List Price
      • $239/SF
      • 23 Days On Market
      • Last Sold Price $700,000
      • Jul 20, 2023

      Last Listing Agent Jennifer Connolly BHHS Gross & Jansen

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

    $215,000

    • 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
  • 6 Vista Dr, Chester, NY 10918

    $515,000 Sold Mar 09, 2026

    6 Vista Dr, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,934 Sq Ft
    • Built 1998

    Last Sold Summary

    • 3% Above List Price
    • $266/SF
    • 41 Days On Market

    Current Estimated Value $519,124

    Last Listing Agent Christine Koenig Keller Williams Realty

    6 Vista Dr, Chester, NY 10918
    • 2 Park Place, Chester, NY 10918

      Est $838,047 Not Listed For Sale

      2 Park Place, Chester, NY 10918

      • 4 Beds
      • 4.5 Baths
      • 4,492 Sq Ft
      • Built 1999
      2 Park Place, Chester, NY 10918

      Last Sold Summary

      • 6% Above List Price
      • $176/SF
      • 97 Days On Market
      • Last Sold Price $789,000
      • Dec 13, 2024

      Last Listing Agent Claudia Lepore Keller Williams Realty

Showing Results 121 - 160, Page 4 of 18

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