6,812

Chester, NY Homes

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  • 9 Country Woods Dr, Chester, NY 10918
    9 Country Woods Dr, Chester, NY 10918
    9 Country Woods Dr, Chester, NY 10918
    /30

    $725,000 Pending

    • 5 Beds
    • 2.5 Baths
    • 3,124 Sq Ft

    9 Country Woods Dr, Chester, NY 10918

    Thoughtfully repositioned with a nearly $15,000 price adjustment makes this Country Woods colonial an unbeatable value! Now priced to allow for updates while securing a prime location, generous living space, a beautiful setting, and room to add your personal style. Country Woods is one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers

    Kimberly Starks Howard Hanna Rand Realty

    9 Country Woods Dr, Chester, NY 10918
  • 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
    • 32 Rebecca Rd, Chester, NY 10918

      Est $579,693 Not Listed For Sale

      32 Rebecca Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,411 Sq Ft
      • Built 2000
      32 Rebecca Rd, Chester, NY 10918

      Last Sold Summary

      • 8% Above List Price
      • $222/SF
      • 38 Days On Market

      Last Sold Price $535,000

      Last Listing Agent Rosalie Cook Weichert Realtors

  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /2

    $350,000

    • Land
    • 2 Acres
    • $175,000 per Acre

    220 Oxford Rd, Chester, NY 10918

    A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

    Chaim Weiss Exit Realty Venture

    220 Oxford 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 $540,609

    Last Listing Agent Courtney Tablante Keller Williams Realty

    13 Tulip Ln Unit 4, Monroe, NY 10950
    • 3 Stacey Ln, Chester, NY 10918

      Est $673,350 Not Listed For Sale

      3 Stacey Ln, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,904 Sq Ft
      • Built 1988
      3 Stacey Ln, Chester, NY 10918

      Last Sold Summary

      • 11% Above List Price
      • $208/SF
      • 20 Days On Market

      Last Sold Price $605,000

      Last Listing Agent Abraham Schwartz Priority Management

  • 30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    /7

    $500,000

    • Land
    • 9.78 Acres
    • $51,125 per Acre

    30 Harding Way, Chester, NY 10950

    An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

    Ida Payne Keller Williams Realty

    30 Harding Way, Chester, NY 10950
  • 16 Fernglade Ct, Chester, NY 10918

    $550,000 Sold Apr 23, 2025

    16 Fernglade Ct, Chester, NY 10918

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

    Last Sold Summary

    • 13% Above List Price
    • $165/SF
    • 12 Days On Market

    Current Estimated Value $629,405

    Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group

    16 Fernglade Ct, Chester, NY 10918
    • 56 Goosepond Mountain Rd, Chester, NY 10918

      Est $561,308 Not Listed For Sale

      56 Goosepond Mountain Rd, Chester, NY 10918

      • 3 Beds
      • 3 Baths
      • 3,080 Sq Ft
      • Built 1996
      56 Goosepond Mountain Rd, Chester, NY 10918

      Last Sold Summary

      • 5% Above List Price
      • $174/SF
      • 34 Days On Market

      Last Sold Price $535,000

      Last Listing Agent Linda Ross Linda C Ross Real Estate Inc

  • L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    /3

    $75,000

    • Land
    • 12 Acres
    • $6,250 per Acre

    L62.2 Moffitt Rd, Chester, NY 12817

    12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

    Carol Monroe Najer Realty

    L62.2 Moffitt Rd, 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 $332,846

    Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

    65 Hudson St, Chester, NY 10918
    • 149 Creamery Pond Rd, Chester, NY 10918

      Est $708,404 Not Listed For Sale

      149 Creamery Pond Rd, Chester, NY 10918

      • 3 Beds
      • 3 Baths
      • 2,740 Sq Ft
      • Built 2002
      149 Creamery Pond Rd, Chester, NY 10918

      Last Sold Summary

      • 9% Above List Price
      • $237/SF
      • 47 Days On Market

      Last Sold Price $649,000

      Last Listing Agent Layla Rose Boyles Century 21 Realty Center

  • 1005 Whispering Hills, Chester, NY 10918
    1005 Whispering Hills, Chester, NY 10918
    /2

    $249,900

    • 2 Beds
    • 1.5 Baths
    • 1,053 Sq Ft

    1005 Whispering Hills, Chester, NY 10918

    ONLY CASH OFFERS!! LOW TAXES! Two Level Living! 2 Bedrooms! 1 1/2 Bathrooms! 1 Car Garage! Updated Kitchen! Updated Bathrooms! Living Room with Fireplace! Sliders To Patio! Perfect Commuter Location! Walk to NYC Bus & Shopping! Close to Major Highways! Country Club Living! Clubhouses! Pools! Tennis! Tot Lot! Basketball! Dog Walk!

    Amanda Dnistrian ARC Realty 1 in Sales

    1005 Whispering Hills, Chester, NY 10918
  • 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 $506,294

    Last Listing Agent Christine Koenig Keller Williams Realty

    6 Vista Dr, Chester, NY 10918
    • 169 Creamery Pond Rd, Chester, NY 10918

      Est $676,918 Not Listed For Sale

      169 Creamery Pond Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,436 Sq Ft
      • Built 2002
      169 Creamery Pond Rd, Chester, NY 10918

      Last Sold Summary

      • 16% Above List Price
      • $240/SF
      • 16 Days On Market

      Last Sold Price $585,000

      Last Listing Agent Michele Tobin Keller Williams Realty

  • 34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    /8

    $39,500

    • Land
    • 1.82 Acres
    • $21,703 per Acre

    34 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

    34 Carriage Knolls Rd, Chester, NY 12817
  • 53 Gibson Hill Rd, Chester, NY 10918

    $960,000 Sold Jun 05, 2025

    53 Gibson Hill Rd, Chester, NY 10918

    • 5 Beds
    • 4 Baths
    • 5,312 Sq Ft
    • Built 2010

    Last Sold Summary

    • 4% Below List Price
    • $181/SF
    • 45 Days On Market

    Current Estimated Value $996,840

    Last Listing Agent Roxanne Hartman Timothy W. Kramer

    53 Gibson Hill Rd, Chester, NY 10918
    • 19 Mount Ridge Ct, Monroe, NY 10950

      Est $640,639 Not Listed For Sale

      19 Mount Ridge Ct, Monroe, NY 10950

      • 4 Beds
      • 2.5 Baths
      • 2,698 Sq Ft
      • Built 2000
      19 Mount Ridge Ct, Monroe, NY 10950

      Last Sold Summary

      • 6% Above List Price
      • $223/SF
      • 15 Days On Market

      Last Sold Price $602,000

      Last Listing Agent Christian Baez Keller Williams Hudson Valley

  • 2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    /45

    $1,300,000

    • 4 Beds
    • 2.5 Baths
    • 3,866 Sq Ft

    2948 State Route 94, Chester, NY 10918

    Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

    Elizabeth Broderick Tuxedo Hudson Realty Corp

    2948 State Route 94, Chester, NY 10918
  • 3816 Whispering Hills, Chester, NY 10918

    $380,000 Sold Jul 30, 2025

    3816 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1987

    Last Sold Summary

    • 4% Above List Price
    • $285/SF
    • 28 Days On Market

    Current Estimated Value $384,229

    Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

    3816 Whispering Hills, Chester, NY 10918
    • 7 Mount Ridge Ct, Monroe, NY 10950

      Est $585,395 Not Listed For Sale

      7 Mount Ridge Ct, Monroe, NY 10950

      • 4 Beds
      • 2.5 Baths
      • 2,136 Sq Ft
      • Built 2002
      7 Mount Ridge Ct, Monroe, NY 10950

      Last Sold Summary

      • 6% Above List Price
      • $257/SF
      • 10 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Rosalie Cook Weichert Realtors

  • 1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    1401 Whispering Hills, Chester, NY 10918
    /33

    $289,500

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

    1401 Whispering Hills, Chester, NY 10918

    Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

    Debbie Goldstein Howard Hanna Rand Realty

    1401 Whispering Hills, Chester, NY 10918
  • 40 Mountainside Dr, Chester, NY 10918

    $799,900 Sold Sep 15, 2025

    40 Mountainside Dr, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,500 Sq Ft
    • Built 2024

    Last Sold Summary

    • $320/SF
    • 47 Days On Market

    Current Estimated Value $609,297

    Last Listing Agent Karen Gauvin Our House Real Estate Group

    40 Mountainside Dr, Chester, NY 10918
    • 465 Meri Ln, Monroe, NY 10950

      Est $415,725 Not Listed For Sale

      465 Meri Ln, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,694 Sq Ft
      • Built 2001
      465 Meri Ln, Monroe, NY 10950

      Last Sold Summary

      • 4% Above List Price
      • $236/SF
      • 55 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Wenpeng Guan Keller Williams Hudson Valley

  • 50 Elkay Dr, Chester, NY 10918
    50 Elkay Dr, Chester, NY 10918
    50 Elkay Dr, Chester, NY 10918
    /3

    $675,000

    • Land
    • 2 Acres
    • $337,500 per Acre

    50 Elkay Dr, Chester, NY 10918

    Last remaining parcel available on Elkay Drive in the Chester Industrial Park.This 2-acre industrial lot was previously fully approved for a two-story building with loading docks. While approvals expired approximately 10 years ago, the site’s industrial potential remains strong. Both adjacent parcels are currently under development, with 30,000+ SF warehouse facilities being constructed,

    Leib Glanz Point Realty USA

    50 Elkay Dr, Chester, NY 10918
  • L7 Atateka Dr, Chester, NY 12817
    L7 Atateka Dr, Chester, NY 12817
    /2

    $87,500 Sold Aug 18, 2025

    L7 Atateka Dr, Chester, NY 12817

    • Land
    • 6.38 Acres
    • $13,715 per Acre

    Last Sold Summary

    • 47% Below List Price
    • 608 Days On Market

    Last Listing Agent Jill Brady Hunt ERA

    L7 Atateka Dr, Chester, NY 12817
    • 463 Meri Ln, Monroe, NY 10950

      Est $371,560 Not Listed For Sale

      463 Meri Ln, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,694 Sq Ft
      • Built 2001
      463 Meri Ln, Monroe, NY 10950

      Last Sold Summary

      • 16% Above List Price
      • $189/SF
      • 34 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Beth Palma Keller Williams Realty

  • 3 Tulip Ln, Monroe, NY 10950
    3 Tulip Ln, Monroe, NY 10950
    3 Tulip Ln, Monroe, NY 10950
    /22

    $450,000

    • 4 Beds
    • 2 Baths
    • 1,932 Sq Ft

    3 Tulip Ln, Monroe, NY 10950

    Spacious raised ranch style home offering three bedrooms and two full bathrooms with 1,932 square feet of comfortable living space. Features a 1-car garage and a functional layout perfect for everyday living. The home has been freshly painted, giving it a bright, clean, move-in ready feel. A great opportunity for buyers seeking space, style, and value.

    Geni Silva Ethos Realty LLC

    3 Tulip Ln, Monroe, NY 10950
  • 1610 Whispering Hills, Chester, NY 10918

    $334,900 Sold Jun 20, 2025

    1610 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1984

    Last Sold Summary

    • 6% Below List Price
    • $252/SF
    • 185 Days On Market

    Current Estimated Value $334,012

    Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

    1610 Whispering Hills, Chester, NY 10918
    • 301 Heritage Ln, Monroe, NY 10950

      Est $389,786 Not Listed For Sale

      301 Heritage Ln, Monroe, NY 10950

      • 3 Beds
      • 2.5 Baths
      • 1,698 Sq Ft
      • Built 1998
      301 Heritage Ln, Monroe, NY 10950

      Last Sold Summary

      • 3% Above List Price
      • $224/SF
      • 111 Days On Market

      Last Sold Price $380,000

      Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  • 12 Damian Ct, Chester, NY 10918
    12 Damian Ct, Chester, NY 10918
    12 Damian Ct, Chester, NY 10918
    /34

    $999,000

    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft

    12 Damian Ct, Chester, NY 10918

    Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

    Elimelech Kremer MS Realty Group USA, Inc

    12 Damian Ct, Chester, NY 10918
  • 2317 Whispering Hills, Chester, NY 10918

    $320,000 Sold Dec 12, 2025

    2317 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft
    • Built 1984

    Last Sold Summary

    • 7% Above List Price
    • $299/SF
    • 20 Days On Market

    Current Estimated Value $302,417

    Last Listing Agent Jeffrey Morrissey Epique Realty

    2317 Whispering Hills, Chester, NY 10918
    • 51 Pewter Cir, Chester, NY 10918

      Est $537,800 Not Listed For Sale

      51 Pewter Cir, Chester, NY 10918

      • 3 Beds
      • 3.5 Baths
      • 2,623 Sq Ft
      • Built 2007
      51 Pewter Cir, Chester, NY 10918

      Last Sold Summary

      • 6% Above List Price
      • $193/SF
      • 67 Days On Market

      Last Sold Price $505,000

      Last Listing Agent Michele Tobin Keller Williams Realty

  • 3-4 Adirondack Heights Rd, Chester, NY 12817
    3-4 Adirondack Heights Rd, Chester, NY 12817
    3-4 Adirondack Heights Rd, Chester, NY 12817
    /33

    $89,500

    • Land
    • 12.79 Acres
    • $6,998 per Acre

    3-4 Adirondack Heights Rd, Chester, NY 12817

    Seller financing now available. 12.79 acres of mixed forest and wetlands. Perc tests and engineered plot plans have been completed. APA approved building sites with well & septic locations identified. (2-lots can each be built upon or just have one large lot) Power at the road pedestal box. Tons of hemlock, spruce, and pine trees throughout. Close to Chestertown, 20-minutes to Gore Mountain or

    Walter Swartz Gallo Realty ADK Inc

    3-4 Adirondack Heights Rd, Chester, NY 12817
  • 47 Greycourt Ave, Chester, NY 10918

    $415,000 Sold Jan 23, 2026

    47 Greycourt Ave, Chester, NY 10918

    • 4 Beds
    • 1.5 Baths
    • 1,386 Sq Ft
    • Built 1959

    Last Sold Summary

    • 8% Below List Price
    • $299/SF
    • 81 Days On Market

    Current Estimated Value $420,969

    Last Listing Agent Pedro Garcia Curasi Realty, Inc.

    47 Greycourt Ave, Chester, NY 10918
    • 53 Pewter Cir, Chester, NY 10918

      Est $546,334 Not Listed For Sale

      53 Pewter Cir, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,210 Sq Ft
      • Built 2007
      53 Pewter Cir, Chester, NY 10918

      Last Sold Summary

      • 5% Above List Price
      • $235/SF
      • 33 Days On Market

      Last Sold Price $520,000

      Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  • 4 Well Sweep Ln, Chester, NY 10918
    4 Well Sweep Ln, Chester, NY 10918
    4 Well Sweep Ln, Chester, NY 10918
    /6

    $869,900

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    4 Well Sweep Ln, Chester, NY 10918

    Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

    Carla Terranova Keller Williams Realty

    4 Well Sweep Ln, Chester, NY 10918
  • 11 Saddle Hill Rd, Chester, NY 10918

    $845,000 Sold Dec 18, 2025

    11 Saddle Hill Rd, Chester, NY 10918

    • 4 Beds
    • 4 Baths
    • 3,489 Sq Ft
    • Built 2006

    Last Sold Summary

    • 4% Below List Price
    • $242/SF
    • 97 Days On Market

    Current Estimated Value $838,643

    Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

    11 Saddle Hill Rd, Chester, NY 10918
    • 15 Pewter Cir, Chester, NY 10918

      Est $697,613 Not Listed For Sale

      15 Pewter Cir, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 3,223 Sq Ft
      • Built 1999
      15 Pewter Cir, Chester, NY 10918

      Last Sold Summary

      • 8% Above List Price
      • $200/SF
      • 218 Days On Market

      Last Sold Price $645,000

      Last Listing Agent Jennifer Connolly BHHS Gross & Jansen

  • 2915 Whispering Hills Unit 596, Chester, NY 10918
    2915 Whispering Hills Unit 596, Chester, NY 10918
    2915 Whispering Hills Unit 596, Chester, NY 10918
    /23

    $369,000 Pending

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

    2915 Whispering Hills Unit 596, Chester, NY 10918

    Welcome to your next home in the highly desirable Whispering Hills community! Completely renovated in 2025, this end-unit with a 2-car garage features new flooring on the main level, gleaming hardwood floors upstairs, a modern kitchen with stainless steel appliances, updated bathrooms, recessed lighting throughout, high ceilings, and beautiful modern chandeliers. The bright, open layout includes

    Johanna Monzon Ruballos Century 21 Full Service Realty

    2915 Whispering Hills Unit 596, Chester, NY 10918

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