6,841

Chester, NY Homes

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

    $430,000

    $20K PRICE DROP
    • 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
  • 391 Bull Mill Rd, Chester, NY 10918

    $460,000

    Sold Apr 01, 2026

    391 Bull Mill Rd, Chester, NY 10918

    • 2 Beds
    • 2 Baths
    • 1,714 Sq Ft
    • Built 1900

    Last Sold Summary

    • 25% Below List Price
    • $268/SF
    • 217 Days On Market

    Current Estimated Value $463,163

    Last Listing Agent Alexandra Zinko Century 21 Realty Center

    391 Bull Mill Rd, Chester, NY 10918
    • 128 Booth Rd, Chester, NY 10918

      Est $572,258

      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

      • 179 Days On Market

  • 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
    /25

    $159,000

    $6K PRICE DROP
    • Land
    • 31,798 Sq Ft
    • $217,808 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
  • 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 $315,578

    Last Listing Agent Jeffrey Morrissey Epique Realty

    2317 Whispering Hills, Chester, NY 10918
  • 503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    /13

    $206,000

    $69K PRICE DROP
    • 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
  • 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 $419,147

    Last Listing Agent Pedro Garcia Curasi Realty, Inc.

    47 Greycourt Ave, Chester, NY 10918
  • 45 Whitetail Run, Chester, NY 10918
    45 Whitetail Run, Chester, NY 10918
    45 Whitetail Run, Chester, NY 10918
    /47

    $825,000

    • 4 Beds
    • 2.5 Baths
    • 2,732 Sq Ft

    45 Whitetail Run, Chester, NY 10918

    Set on over 10 private acres in the rolling hills of Orange County, this exceptional custom colonial offers the rare combination of luxury, privacy, and convenience AND just minutes from the heart of Chester and major commuter routes. Built in 2017 and thoughtfully designed with over 2,700 square feet of living space, 45 Whitetail Run delivers the kind of lifestyle buyers dream about but rarely

    Melissa Forsyth Hudson Valley Home Connection

    45 Whitetail Run, 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 $851,831

    Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

    11 Saddle Hill Rd, Chester, NY 10918
    • 11 Park Place, Chester, NY 10918

      Est $789,040

      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

      • 23 Days On Market

  • 58 Nancy Ln, Chester, NY 10918
    58 Nancy Ln, Chester, NY 10918
    58 Nancy Ln, Chester, NY 10918
    /49

    $769,000

    $31K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Price improvement! Wait until you see all this home has to offer! Perched atop the desirable Fieldcrest subdivision with sweeping panoramic views and unforgettable sunsets, this spectacular Colonial offers exceptional space, comfort, and versatility both inside and out. Set on 1.3 picturesque acres, this beautifully maintained home is designed for everyday living and effortless entertaining.A

    Gina Dudgeon Howard Hanna Rand Realty

    58 Nancy Ln, Chester, NY 10918
  • 21 Jeffrey Dr, Chester, NY 10918

    $560,000

    Sold Aug 19, 2025

    21 Jeffrey Dr, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,240 Sq Ft
    • Built 1993

    Last Sold Summary

    • 6% Above List Price
    • $250/SF
    • 37 Days On Market

    Current Estimated Value $583,259

    Last Listing Agent Kevin Tuhy Keller Williams Realty

    21 Jeffrey Dr, Chester, NY 10918
    • 2 Park Place, Chester, NY 10918

      Est $946,494

      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

      • 97 Days On Market

  • 38 Jefferson Dr, Monroe, NY 10950
    38 Jefferson Dr, Monroe, NY 10950
    38 Jefferson Dr, Monroe, NY 10950
    /21

    $549,000

    Pending
    • 3 Beds
    • 1.5 Baths
    • 1,644 Sq Ft

    38 Jefferson Dr, Monroe, NY 10950

    Welcome home! This wonderful quiet neighborhood, Lake Hill Farms, off of Lakes Rd. On the outskirts of Monroe, makes this a great commuter and convenient location, from hiking trails, parks, Woodbury Commons, shopping, train station, and dinning. This home has a nice sized backyard. The deck furniture and gazebo are included, underneath your deck is an enclosed screened in patio which will give

    Lance Gibbs Arrowhead Realty

    38 Jefferson Dr, Monroe, NY 10950
  • 15 Mari Rd, Chester, NY 10918

    $500,000

    Sold Oct 20, 2025

    15 Mari Rd, Chester, NY 10918

    • 4 Beds
    • 2 Baths
    • 1,888 Sq Ft
    • Built 1971

    Last Sold Summary

    • $265/SF
    • 56 Days On Market

    Current Estimated Value $503,340

    Last Listing Agent Nicholas Carbone HomeSmart Homes & Estates

    15 Mari Rd, Chester, NY 10918
  • 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
  • 7 Garden St, Chester, NY 10918

    $400,000

    Sold Jul 28, 2025

    7 Garden St, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • Built 1900

    Last Sold Summary

    • $279/SF
    • 25 Days On Market

    Current Estimated Value $403,960

    Last Listing Agent Harmoni VanEtten eXp Realty

    7 Garden St, Chester, NY 10918
    • 119 Booth Rd, Chester, NY 10918

      Est $555,148

      Not Listed For Sale

      119 Booth Rd, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft
      • Built 1976
      119 Booth Rd, Chester, NY 10918

      Last Sold Summary

      • 39 Days On Market

  • 1414 Kings Hwy, Chester, NY 10918
    1414 Kings Hwy, Chester, NY 10918
    1414 Kings Hwy, Chester, NY 10918
    /9

    $879,900

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

    1414 Kings Hwy, 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

    1414 Kings Hwy, Chester, NY 10918
  • 2 Laura Dr, Chester, NY 10918

    $690,000

    Sold Jul 09, 2025

    2 Laura Dr, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,592 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Above List Price
    • $266/SF
    • 31 Days On Market

    Current Estimated Value $694,059

    Last Listing Agent Virginia Corbett eXp Realty

    2 Laura Dr, Chester, NY 10918
    • 61 Nancy Ln, Chester, NY 10918

      Est $715,227

      Not Listed For Sale

      61 Nancy Ln, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,700 Sq Ft
      • Built 2002
      61 Nancy Ln, Chester, NY 10918

      Last Sold Summary

      • 35 Days On Market

  • 78 Goshen Rd, Chester, NY 10918
    78 Goshen Rd, Chester, NY 10918
    78 Goshen Rd, Chester, NY 10918
    /50

    $725,000

    Pending
    • 4 Beds
    • 4 Baths
    • 3,908 Sq Ft

    78 Goshen Rd, Chester, NY 10918

    STOP THE SEARCH!!!! THIS ONE, IS ONE OF A KIND!!! HALF-COURT BASKETBALL COURT, RADIANT HEATED PRIVATE POOL, KILLER FINISHED LOWER LEVEL!!!!! Welcome to 78 Goshen Road, a beautifully maintained 4-bedroom Colonial in the Town of Blooming Grove within the sought after Washingtonville School District, set on a quiet country road with 2.3 acres of space and privacy. With over 3,900 square feet of

    Frank Muccari Cronin & Company Real Estate

    78 Goshen Rd, Chester, NY 10918
  • 9 Country Woods Dr, Chester, NY 10918

    $690,000

    Sold Jun 08, 2026

    9 Country Woods Dr, Chester, NY 10918

    • 5 Beds
    • 2.5 Baths
    • 3,124 Sq Ft
    • Built 2002

    Last Sold Summary

    • 8% Below List Price
    • $221/SF
    • 140 Days On Market

    Current Estimated Value $720,595

    Last Listing Agent Kimberly Starks Howard Hanna Rand Realty

    9 Country Woods Dr, Chester, NY 10918
    • 88 Nancy Ln, Chester, NY 10918

      Est $641,608

      Not Listed For Sale

      88 Nancy Ln, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,768 Sq Ft
      • Built 1992
      88 Nancy Ln, Chester, NY 10918

      Last Sold Summary

      • 44 Days On Market

  • 3318 State Route 94, Chester, NY 10918
    3318 State Route 94, Chester, NY 10918
    3318 State Route 94, Chester, NY 10918
    /29

    $549,900

    • 3 Beds
    • 2 Baths
    • 2,138 Sq Ft

    3318 State Route 94, Chester, NY 10918

    This beautifully updated homes features wood floors throughout, three spacious bedrooms, two den/office spaces, formal dining room, and two full baths. The expansive primary suite has an additional 10X10 sitting room, generous walk-in closet, an en-suite with linen closet, walk-in shower and Venetian soaking tub. The main floor bathroom is equally large with a jetted bathtub. Both the living room

    Asha Keegan Howard Hanna Rand Realty

    3318 State Route 94, Chester, NY 10918
  • 3911 Whispering Hills, Chester, NY 10918

    $367,500

    Sold Aug 29, 2025

    3911 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,316 Sq Ft
    • Built 1987

    Last Sold Summary

    • 1% Above List Price
    • $279/SF
    • 25 Days On Market

    Current Estimated Value $372,599

    Last Listing Agent Hershel Lowy Master Realty Group Inc.

    3911 Whispering Hills, Chester, NY 10918
    • 38 Rebecca Rd, Chester, NY 10918

      Est $592,914

      Not Listed For Sale

      38 Rebecca Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 1,910 Sq Ft
      • Built 1990
      38 Rebecca Rd, Chester, NY 10918

      Last Sold Summary

      • 30 Days On Market

  • 607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    /46

    $319,900

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    607 Mountain Laurel Dr, Monroe, NY 10950

    Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

    Rosalie Cook Weichert Realtors

    607 Mountain Laurel Dr, Monroe, NY 10950
  • 18 Grant Dr, Monroe, NY 10950

    $610,000

    Sold Sep 19, 2025

    18 Grant Dr, Monroe, NY 10950

    • 4 Beds
    • 2.5 Baths
    • 2,144 Sq Ft
    • Built 1994

    Last Sold Summary

    • 6% Above List Price
    • $285/SF
    • 27 Days On Market

    Current Estimated Value $612,824

    Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

    18 Grant Dr, Monroe, NY 10950
    • 32 Rebecca Rd, Chester, NY 10918

      Est $612,514

      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

      • 38 Days On Market

  • 152 Eagleton Dr, Monroe, NY 10950
    152 Eagleton Dr, Monroe, NY 10950
    152 Eagleton Dr, Monroe, NY 10950
    /37

    $385,000

    • 2 Beds
    • 2.5 Baths
    • 1,490 Sq Ft

    152 Eagleton Dr, Monroe, NY 10950

    Move right into this beautifully maintained townhouse in the highly desirable Windridge Complex, offering approximately 1,500 square feet of comfortable living space and peaceful lake views. This inviting home features 2 spacious bedrooms, 2.5 bathrooms, and a functional floor plan designed for today's lifestyle.The main level boasts a dramatic two-story living room with a cozy gas fireplace,

    Alissa Taylor-Vetell Keller Williams Realty

    152 Eagleton Dr, Monroe, NY 10950
  • 16 Ayr Rd, Chester, NY 10918

    $536,000

    Sold Aug 06, 2025

    16 Ayr Rd, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,716 Sq Ft
    • Built 1972

    Last Sold Summary

    • 9% Above List Price
    • $312/SF
    • 62 Days On Market

    Current Estimated Value $540,751

    Last Listing Agent Luanne McGann Century 21 Full Service Realty

    16 Ayr Rd, Chester, NY 10918
    • 3 Stacey Ln, Chester, NY 10918

      Est $690,573

      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

      • 20 Days On Market

  • L1.34 McPhillips Pine Ln, Chester, NY 12817
    L1.34 McPhillips Pine Ln, Chester, NY 12817
    L1.34 McPhillips Pine Ln, Chester, NY 12817
    /9

    $275,000

    • Land
    • 7.53 Acres
    • $36,521 per Acre

    L1.34 McPhillips Pine Ln, Chester, NY 12817

    If you are looking for an ultra private lot with access (dock and beach rights) to one of the pristine exclusive lakes in the Adirondacks, you found it. Friends Lake is the home to cool people and is private, jet-ski free, with a water ski course and simply no nonsense. Only 2O minutes to Lake George and Gore Mountain Ski Area. About 4 hours from NYC and 2.5 hours to Montreal. Saratoga Springs is

    Michael Lynch Coldwell Banker Prime Properties

    L1.34 McPhillips Pine Ln, Chester, NY 12817
  • 80 Pewter Cir, Chester, NY 10918

    $520,000

    Sold Feb 11, 2026

    80 Pewter Cir, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,946 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $267/SF
    • 25 Days On Market

    Current Estimated Value $523,804

    Last Listing Agent Julie Klein BHG Real Estate Green Team

    80 Pewter Cir, Chester, NY 10918

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