6,841

Chester, NY Homes

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  • 1414 N Gore Rd, Chester, NY 12817
    1414 N Gore Rd, Chester, NY 12817
    1414 N Gore Rd, Chester, NY 12817
    /3

    $48,000

    • Land
    • 3.6 Acres
    • $13,333 per Acre

    1414 N Gore Rd, Chester, NY 12817

    North Gore Lot - Come build your dream on home this 3.6 acre wooded lot with power available roadside and perc test completed. Secluded location, yet only 15 minutes to Gore Mountain and 10 minutes to Minerva Beach with abundant outdoor recreation opportunities.

    Agent Photo

    Amanda Gadway

    Gadway Realty

    (518) 768-9981

    1414 N Gore Rd, Chester, NY 12817
  • 256 Heritage Ln, Monroe, NY 10950
    256 Heritage Ln, Monroe, NY 10950
    256 Heritage Ln, Monroe, NY 10950
    /22

    $3,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,699 Sq Ft
    • Townhouse for Rent

    256 Heritage Ln, Monroe, NY 10950

    Monroe, NY - Spacious, two-level townhouse end unit. First floor features living room/dining area, kitchen with dinette area, half bath, laundry room & garage. Top level contains master bedroom suite with full bath & walk-in closet, second bedroom, third bedroom, second full bathroom and hallway walk-in closet. Additional features: Young carpeting, entry way flooring, butcher block counter top &

    Frank Gomez HomeSmart Homes & Estates

    256 Heritage Ln, Monroe, NY 10950
  • 4703 Whispering Hills Dr, Chester, NY 10918

    $382,000

    Sold Jan 12, 2026

    4703 Whispering Hills Dr, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1991

    Last Sold Summary

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

    Current Estimated Value $370,987

    Last Listing Agent Erin Connolly-Frontino Artisan Realty

    4703 Whispering Hills Dr, Chester, NY 10918
  • 1 Oakland Ave, Chester, NY 10918
    1 Oakland Ave, Chester, NY 10918
    1 Oakland Ave, Chester, NY 10918
    /50

    $1,000,000

    • 4 Beds
    • 2.5 Baths
    • 3,955 Sq Ft

    1 Oakland Ave, Chester, NY 10918

    Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    (845) 237-3716

    1 Oakland Ave, Chester, NY 10918
  • 27 Midway Dr, Monroe, NY 10950
    27 Midway Dr, Monroe, NY 10950
    27 Midway Dr, Monroe, NY 10950
    /13

    $2,800 Per Month

    • 3 Beds
    • 1 Bath
    • 988 Sq Ft
    • House for Rent

    27 Midway Dr, Monroe, NY 10950

    Charming Ranch home is waiting for you! Super condition! Beautiful perfectly maintained kitchen, 3 Bedrooms and 1 full bath. Enjoy the secluded deck surrounded with beautiful greenery! This Home has Walton Lake rights! Schedule your tour today!

    Joseph Rosenfeld Flag Realty Group

    27 Midway Dr, Monroe, NY 10950
  • 242 Meadow Ave, Chester, NY 10918

    $225,000

    Sold Jun 30, 2025

    242 Meadow Ave, Chester, NY 10918

    • 4 Beds
    • 3 Baths
    • 2,519 Sq Ft
    • Built 1930

    Last Sold Summary

    • $89/SF
    • 56 Days On Market

    Current Estimated Value $348,000

    Last Listing Agent Kathleen Strong Hudson Valley Griffith

    242 Meadow Ave, Chester, NY 10918
  • 2722 Whispering Hills Unit 542, Chester, NY 10918
    2722 Whispering Hills Unit 542, Chester, NY 10918
    2722 Whispering Hills Unit 542, Chester, NY 10918
    /37

    $424,999

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

    2722 Whispering Hills Unit 542, Chester, NY 10918

    New beginnings offered in this light and bright fully refreshed end unit in the highly sought after Whispering Hills community. Featuring new designer paint throughout, brand new luxury vinyl plank (LVP) flooring, new stainless steel appliances, two car garage with recently installed garage doors and so much more. Located close to major highway, NYC bus and shopping. Club house with gym,

    Agent Photo

    Erin Connolly-Frontino

    Artisan Realty

    (845) 932-1237

    2722 Whispering Hills Unit 542, Chester, NY 10918
  • 1502 Whispering Hills, Chester, NY 10918
    1502 Whispering Hills, Chester, NY 10918
    1502 Whispering Hills, Chester, NY 10918
    /33

    $2,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Townhouse for Rent

    1502 Whispering Hills, Chester, NY 10918

    Beautiful 3 bedrooms and 2 baths in Whispering Hills. Updated and freshly painted. New carpeting. Fire place and vaulted ceiling.Enjoy resort style living with pools, tennis courts, club house, gym, playgrounds and basketball courts. Located close to major highways for an easy commute. Additional Information: ParkingFeatures:1 Car Attached,Storage: Garage,

    Nikki Grzegorzewski Keller Williams Realty

    1502 Whispering Hills, Chester, NY 10918
  • 12 Bianca Blvd, Chester, NY 10918

    $575,000

    Sold Sep 23, 2025

    12 Bianca Blvd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Built 1987

    Last Sold Summary

    • 2% Below List Price
    • $180/SF
    • 126 Days On Market

    Current Estimated Value $653,625

    Last Listing Agent Aoife Freeman eXp Realty

    12 Bianca Blvd, Chester, NY 10918
    • 78 Panther Mtn Rd, Chester, NY 12817
      78 Panther Mtn Rd, Chester, NY 12817
      78 Panther Mtn Rd, Chester, NY 12817
      /33

      Not Listed For Sale

      78 Panther Mtn Rd, Chester, NY 12817

      • 3 Beds
      • 1 Bath
      • 876 Sq Ft
      • Built 1961
      78 Panther Mtn Rd, Chester, NY 12817

      Last Sold Summary

      • 68 Days On Market

  • 223 Eagleton Dr, Monroe, NY 10950
    223 Eagleton Dr, Monroe, NY 10950
    223 Eagleton Dr, Monroe, NY 10950
    /36

    $395,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,694 Sq Ft

    223 Eagleton Dr, Monroe, NY 10950

    Welcome home to this tastefully updated and meticulously maintained 3 bedroom, 2.5 bath unit in a highly sought after community in the Monroe Woodbury school district. The Windridge community is clustered around ponds adding to the country feel. Located near the back of the cul-de-sac, this home features an open floorplan for easy living and entertaining. Step out of the sliding door in the

    Agent Photo

    Theresa Powers

    Keller Williams Realty

    (329) 218-1935

    223 Eagleton Dr, Monroe, NY 10950
  • 1403 Kings Hwy, Chester, NY 10918
    1403 Kings Hwy, Chester, NY 10918
    1403 Kings Hwy, Chester, NY 10918
    /43

    $3,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 3,200 Sq Ft
    • Apartment for Rent

    1403 Kings Hwy, Chester, NY 10918

    Luxury Farmhouse Rental in the Heart and Soul of Sugar Loaf – Warwick Schools! Experience country luxury at its finest in this stunning farmhouse rental located in the charming hamlet of Sugar Loaf. Designed for those who appreciate quality craftsmanship and timeless character, this exceptional home offers approximately 3,200 square feet of beautifully appointed living space. Step inside to

    Carla Terranova Keller Williams Realty

    1403 Kings Hwy, Chester, NY 10918
  • 100 Marian Ct, Warwick, NY 10990

    $411,000

    Sold Jul 08, 2025

    100 Marian Ct, Warwick, NY 10990

    • 3 Beds
    • 2.5 Baths
    • 1,528 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Above List Price
    • $269/SF
    • 26 Days On Market

    Current Estimated Value $431,265

    Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

    100 Marian Ct, Warwick, NY 10990
    • L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
      L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
      L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
      /3

      Not Listed For Sale

      L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

      L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

      Last Sold Summary

      • 16 Days On Market

  • 492 Black Meadow Rd, Chester, NY 10918
    492 Black Meadow Rd, Chester, NY 10918
    492 Black Meadow Rd, Chester, NY 10918
    /18

    $399,000

    • Land
    • 46 Acres
    • $8,674 per Acre

    492 Black Meadow Rd, Chester, NY 10918

    Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife. Ideal for recreational use including hiking, hunting, nature walks, bird watching,

    Agent Photo

    Ewa Kusmierek

    eXp Realty

    (845) 582-7035

    492 Black Meadow Rd, Chester, NY 10918
  • 71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    /17

    $58,900

    Sold Jun 12, 2026

    71 Carriage Knoll Rd, Chester, NY 12817

    • Land
    • 1.89 Acres
    • $31,164 per Acre

    Last Sold Summary

    • 39% Above List Price
    • 576 Days On Market

    Last Listing Agent Walter Swartz Gallo Realty ADK Inc

    71 Carriage Knoll Rd, Chester, NY 12817
  • 86 Long Vista Ln, Chester, NY 10918
    86 Long Vista Ln, Chester, NY 10918
    86 Long Vista Ln, Chester, NY 10918
    /47

    $985,000

    • 5 Beds
    • 3.5 Baths
    • 3,764 Sq Ft

    86 Long Vista Ln, Chester, NY 10918

    Some properties are simply worth talking about... this one has all the bells & whistles you're seeking! Privately set on 5.2 scenic acres within the Warwick School District and just one hour from NYC, this distinguished Colonial pairs timeless elegance with resort-style outdoor living, mountain views, and exceptional multi-generational flexibility. A gracious front porch sets the tone, welcoming

    Agent Photo

    Jennifer DiCostanzo

    RE/MAX Town & Country

    (845) 606-3942

    86 Long Vista Ln, Chester, NY 10918
  • 4508 Whispering Hills, Chester, NY 10918

    $300,000

    Sold Apr 20, 2026

    4508 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1987

    Last Sold Summary

    • 8% Below List Price
    • $280/SF
    • 44 Days On Market

    Current Estimated Value $301,889

    Last Listing Agent Ammar Iqbal eXp Realty

    4508 Whispering Hills, Chester, NY 10918
  • 133 E East Shore Dr, Chester, NY 12817
    133 E East Shore Dr, Chester, NY 12817
    133 E East Shore Dr, Chester, NY 12817
    /25

    $875,000

    Pending
    • 2 Beds
    • 2.5 Baths
    • 1,572 Sq Ft

    133 E East Shore Dr, Chester, NY 12817

    A rare opportunity to own a Lakefront Home on Loon Lake. Nestled along the shores of beautiful Loon Lake, this private waterfront retreat offers breathtaking sunset views with a stunning mountain backdrop. This 2-bedroom, 2.5-bath home could live comfortably as a 3-bedroom (septic is sized for a 3 BR) The flexible space is currently used as a home office. Enjoy indoor-outdoor living with a

    Barbara Kearney Hunt ERA

    133 E East Shore Dr, Chester, NY 12817
  • 9 June Rd, Chester, NY 10918

    $620,000

    Sold Oct 29, 2025

    9 June Rd, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,402 Sq Ft
    • Built 1999

    Last Sold Summary

    • 4% Below List Price
    • $258/SF
    • 52 Days On Market

    Current Estimated Value $627,056

    Last Listing Agent Jason Madison eXp Realty

    9 June Rd, Chester, NY 10918
    • 20 High St, Chester, NY 10918

      Est $487,249

      Not Listed For Sale

      20 High St, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 2,488 Sq Ft
      • Built 1825
      20 High St, Chester, NY 10918

      Last Sold Summary

      • 35 Days On Market

  • 1.2 Cobble Creek Rd, Chester, NY 12853
    1.2 Cobble Creek Rd, Chester, NY 12853
    1.2 Cobble Creek Rd, Chester, NY 12853
    /22

    $79,995

    • Land
    • 20.26 Acres
    • $3,948 per Acre

    1.2 Cobble Creek Rd, Chester, NY 12853

    Escape to the mountains with this beautiful 20-acre property in Chester, NY, ideally situated along a year-round maintained town road. The terrain gently climbs from the road, leading to multiple APA-approved building sites for an off-grid cabin or hunting camp offering excellent privacy in a quiet woodland setting. The property features a healthy forest of Northern hardwoods including maple,

    Marc Christmas Christmas and Associates

    1.2 Cobble Creek Rd, Chester, NY 12853
  • 3708 Whispering Hills, Chester, NY 10918

    $310,000

    Sold Nov 10, 2025

    3708 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1990

    Last Sold Summary

    • 5% Above List Price
    • $289/SF
    • 26 Days On Market

    Current Estimated Value $311,601

    Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

    3708 Whispering Hills, Chester, NY 10918
    • 221 Oxford Rd, Chester, NY 10918

      Est $984,623

      Not Listed For Sale

      221 Oxford Rd, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 4,644 Sq Ft
      • Built 2000
      221 Oxford Rd, Chester, NY 10918

      Last Sold Summary

      • 132 Days On Market

  • 1.4 Cobble Creek Rd, Chester, NY 12853
    1.4 Cobble Creek Rd, Chester, NY 12853
    1.4 Cobble Creek Rd, Chester, NY 12853
    /23

    $99,995

    Pending
    • Land
    • 22.88 Acres
    • $4,370 per Acre

    1.4 Cobble Creek Rd, Chester, NY 12853

    Experience the best of Adirondack living on this scenic 22-acre property in Chester, New York. Accessible year-round from a town-maintained road with power nearby, the land offers several elevated APA-approved building sites perfectly positioned for a private cabin, vacation home, or full-time residence. The property is richly forested with mature Northern hardwoods including maple, oak, birch,

    Marc Christmas Christmas and Associates

    1.4 Cobble Creek Rd, Chester, NY 12853
  • 23 Renies Rd, Chester, NY 10918

    $644,000

    Sold Feb 12, 2026

    23 Renies Rd, Chester, NY 10918

    • 3 Beds
    • 3 Baths
    • 3,200 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $201/SF
    • 100 Days On Market

    Current Estimated Value $675,208

    Last Listing Agent Kristie Jacques Century 21 Full Service Realty

    23 Renies Rd, Chester, NY 10918
    • 26 Maple Ln, Monroe, NY 10950

      Est $506,856

      Not Listed For Sale

      26 Maple Ln, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,956 Sq Ft
      • Built 1964
      26 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 22 Days On Market

  • 1.3 Cobble Creek Rd, Chester, NY 12853
    1.3 Cobble Creek Rd, Chester, NY 12853
    /2

    $119,995

    • Land
    • 30.95 Acres
    • $3,877 per Acre

    1.3 Cobble Creek Rd, Chester, NY 12853

    Rarely does a property combine privacy, natural beauty and convenience as well as this 30-acre tract in Chester, New York. Located on a year-round town road, the land offers easy access while maintaining the peaceful feeling of a true Adirondack forest retreat. Several elevated APA-approved building sites are scattered throughout the property, offering ideal locations for an off-grid cabin or

    Marc Christmas Christmas and Associates

    1.3 Cobble Creek Rd, Chester, NY 12853
  • 27 Grand View Terrace, Chester, NY 10918

    $780,000

    Sold Aug 15, 2025

    27 Grand View Terrace, Chester, NY 10918

    • 5 Beds
    • 3.5 Baths
    • 4,490 Sq Ft
    • Built 2004

    Last Sold Summary

    • 3% Above List Price
    • $174/SF
    • 43 Days On Market

    Current Estimated Value $797,760

    Last Listing Agent Randolph Rogers eXp Realty

    27 Grand View Terrace, Chester, NY 10918
    • 13 Maple Ln, Monroe, NY 10950

      Est $460,663

      Not Listed For Sale

      13 Maple Ln, Monroe, NY 10950

      • 4 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1962
      13 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 36 Days On Market

  • Rd, Chester, NY 12853
    Rd, Chester, NY 12853
    Rd, Chester, NY 12853
    /22

    $89,995

    • Land
    • 25.03 Acres
    • $3,595 per Acre

    Rd, Chester, NY 12853

    Adirondack Mountain Retreat with Stream and Trails Discover 25 acres of classic Adirondack wilderness in Chester, New York, tucked along a year-round, town-maintained road. This exceptional property rises gently from the roadside to several attractive, APA-approved building locations, offering excellent opportunities for an off-grid cabin, or vacation retreat. The land is heavily wooded with a

    Marc Christmas Christmas and Associates

    Rd, Chester, NY 12853
  • 68 Southside Dr, Monroe, NY 10950

    $380,000

    Sold Sep 15, 2025

    68 Southside Dr, Monroe, NY 10950

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft
    • Built 1940

    Last Sold Summary

    • 15% Below List Price
    • $233/SF
    • 49 Days On Market

    Current Estimated Value $406,534

    Last Listing Agent Carol Buchanan BHG Real Estate Green Team

    68 Southside Dr, Monroe, NY 10950
    • 7 Maple Ln, Monroe, NY 10950

      Est $531,906

      Not Listed For Sale

      7 Maple Ln, Monroe, NY 10950

      • 3 Beds
      • 2 Baths
      • 2,104 Sq Ft
      • Built 1961
      7 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 30 Days On Market

  • 9 Derose Ln, Chester, NY 10918
    9 Derose Ln, Chester, NY 10918
    9 Derose Ln, Chester, NY 10918
    /50

    $675,000

    • 4 Beds
    • 2.5 Baths
    • 3,100 Sq Ft

    9 Derose Ln, Chester, NY 10918

    Welcome to this elegant colonial in the highly regarded Warwick School District, where timeless charm meets modern comfort. Relax on the inviting front porch while enjoying your morning coffee and breathtaking mountain views. Inside, spacious sun-filled rooms and hardwood flooring throughout the formal living and dining areas create a warm, welcoming atmosphere. A dramatic two-story foyer sets

    Donna Gennaro Howard Hanna Rand Realty

    9 Derose Ln, Chester, NY 10918
  • 284 Bull Mill Rd, Chester, NY 10918

    $850,000

    Sold Oct 22, 2025

    284 Bull Mill Rd, Chester, NY 10918

    • 5 Beds
    • 3 Baths
    • 3,485 Sq Ft
    • Built 1997

    Last Sold Summary

    • $244/SF
    • 20 Days On Market

    Current Estimated Value $843,057

    Last Listing Agent Jayne M. Prechtel Keller Williams Valley Realty

    284 Bull Mill Rd, Chester, NY 10918
    • 31 Maple Ln, Monroe, NY 10950

      Est $445,015

      Not Listed For Sale

      31 Maple Ln, Monroe, NY 10950

      • 3 Beds
      • 1 Bath
      • 1,686 Sq Ft
      • Built 1969
      31 Maple Ln, Monroe, NY 10950

      Last Sold Summary

      • 18 Days On Market

Showing Results 41 - 80, Page 2 of 18

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