6,751

Chester, NY Homes

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  • 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 Pending
    • 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
  • 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 $467,771

    Last Listing Agent Alexandra Zinko Century 21 Realty Center

    391 Bull Mill Rd, Chester, NY 10918
    • 243 Bull Mill Rd, Chester, NY 10918

      Est $617,889

      Not Listed For Sale

      243 Bull Mill Rd, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,021 Sq Ft
      • Built 1985
      243 Bull Mill Rd, Chester, NY 10918

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Debra gay Coldwell Banker Realty

  • 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
  • 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 $319,576

    Last Listing Agent Jeffrey Morrissey Epique Realty

    2317 Whispering Hills, Chester, NY 10918
    • 119 Booth Rd, Chester, NY 10918

      Est $547,020

      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

      Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  • 985 Craigville Rd, Chester, NY 10918
    985 Craigville Rd, Chester, NY 10918
    985 Craigville Rd, Chester, NY 10918
    /36

    $800,000

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

    985 Craigville Rd, Chester, NY 10918

    Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

    DAVID DEBERARDINIS Serhant LLC

    985 Craigville Rd, Chester, NY 10918
  • L14 Adirondack Heights Rd Lot 8, Chester, NY 12817
    L14 Adirondack Heights Rd Lot 8, Chester, NY 12817
    L14 Adirondack Heights Rd Lot 8, Chester, NY 12817
    /6

    $27,000

    Sold Jul 08, 2026

    L14 Adirondack Heights Rd Lot 8, Chester, NY 12817

    • Land
    • 1.57 Acres
    • $17,197 per Acre

    Last Sold Summary

    • 32% Below List Price
    • 25 Days On Market

    Last Listing Agent Norman Benjamin KW Platform

    L14 Adirondack Heights Rd Lot 8, Chester, NY 12817
    • 61 Nancy Ln, Chester, NY 10918

      Est $717,290

      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

      Last Listing Agent Martha Randazzo Howard Hanna Rand Realty

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

    $749,999

    $50K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Imagine ending every day watching the sun set from your front porch, with breathtaking views that change beautifully through every season. Sunset views, a fenced backyard, brand-new Trex deck, above-ground pool, home office, and the flexibility of **four sleeping spaces** make this property truly stand out. Perched atop the highly sought-after Fieldcrest subdivision, this stunning Colonial is

    Gina Dudgeon Howard Hanna Rand Realty

    58 Nancy Ln, Chester, NY 10918
  • 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 $418,638

    Last Listing Agent Pedro Garcia Curasi Realty, Inc.

    47 Greycourt Ave, Chester, NY 10918
    • 88 Nancy Ln, Chester, NY 10918

      Est $639,280

      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

      Last Listing Agent Christopher Rose REALHome Services & Solutions

  • 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
  • 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 $864,445

    Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

    11 Saddle Hill Rd, Chester, NY 10918
    • 38 Rebecca Rd, Chester, NY 10918

      Est $587,370

      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

      Last Listing Agent Steve Esposito HomeSmart Homes & Estates

  • 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 Imperial Park, Chester, NY 10918

    $107,500

    Sold Aug 06, 2026

    2 Imperial Park, Chester, NY 10918

    • Land
    • 8,873 Sq Ft
    • $527,737 per Acre

    Last Sold Summary

    • 28% Below List Price
    • 109 Days On Market

    Last Listing Agent William Scolza HomeSmart Homes & Estates

    2 Imperial Park, Chester, NY 10918
    • 32 Rebecca Rd, Chester, NY 10918

      Est $593,425

      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

      Last Listing Agent Rosalie Cook Weichert Realtors

  • 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
  • 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 $584,873

    Last Listing Agent Kevin Tuhy Keller Williams Realty

    21 Jeffrey Dr, Chester, NY 10918
    • 3 Stacey Ln, Chester, NY 10918

      Est $681,569

      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

      Last Listing Agent Abraham Schwartz Priority Management

  • 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 10 X 10-ft. 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

    Asha Keegan Howard Hanna Rand Realty

    3318 State Route 94, Chester, NY 10918
  • 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 $503,371

    Last Listing Agent Nicholas Carbone HomeSmart Homes & Estates

    15 Mari Rd, Chester, NY 10918
    • 56 Goosepond Mountain Rd, Chester, NY 10918

      Est $566,684

      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

      • 34 Days On Market

      Last Listing Agent Linda Ross Linda C Ross Real Estate Inc

  • 166 Bull Mill Rd, Chester, NY 10918
    166 Bull Mill Rd, Chester, NY 10918
    166 Bull Mill Rd, Chester, NY 10918
    /37

    $340,000

    • 2 Beds
    • 1 Bath
    • 1,004 Sq Ft

    166 Bull Mill Rd, Chester, NY 10918

    Step into the timeless charm of this historic 1800s farmhouse, where character and history come together in a warm, inviting setting. Original details, classic craftsmanship, and the unique character of a bygone era create a home unlike today’s new construction. Adding to its rich history, the original deed to the property is included and will be conveyed to the new owner—a rare keepsake that

    Stephen Ramundo Keller Williams Valley Realty

    166 Bull Mill 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 $772,831

    Last Listing Agent Kimberly Starks Howard Hanna Rand Realty

    9 Country Woods Dr, Chester, NY 10918
    • 137 Creamery Pond Rd, Chester, NY 10918

      Est $770,947

      Not Listed For Sale

      137 Creamery Pond Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,822 Sq Ft
      • Built 2002
      137 Creamery Pond Rd, Chester, NY 10918

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent John Stika Keller Williams Realty

  • 0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914
    0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914
    /2

    $1,975,000

    • Land
    • 79.2 Acres
    • $24,937 per Acre

    0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914

    A once-in-a-generation opportunity to acquire 79.2 acres in the highly sought-after Town of Blooming Grove. Rarely does a parcel of this size become available in one of Orange County's fastest-growing and most desirable communities. Whether you're a long-term investor, developer, or land banker, this exceptional property offers tremendous upside and the potential to capitalize on the area's

    Yoel Kornbluh Mount Realty

    0 Route 94 Unit KEY1035933, Blooming Grove, NY 10914
  • 5 Gabriels Dr, Chester, NY 10918

    $830,000

    Sold Jul 07, 2026

    5 Gabriels Dr, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,722 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Below List Price
    • $305/SF
    • 38 Days On Market

    Current Estimated Value $853,625

    Last Listing Agent Naomi Streicher Q Home Sales

    5 Gabriels Dr, Chester, NY 10918
    • 157 Creamery Pond Rd, Chester, NY 10918

      Est $847,988

      Not Listed For Sale

      157 Creamery Pond Rd, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 4,021 Sq Ft
      • Built 2001
      157 Creamery Pond Rd, Chester, NY 10918

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Carla Terranova Keller Williams Realty

  • 402 Mountain Laurel Dr, Monroe, NY 10950
    402 Mountain Laurel Dr, Monroe, NY 10950
    402 Mountain Laurel Dr, Monroe, NY 10950
    /31

    $374,000

    Open Sun 12PM - 4PM $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    402 Mountain Laurel Dr, Monroe, NY 10950

    Waterfront living at its finest! Welcome to this beautifully maintained center-unit townhome in one of Monroe's most sought-after communities. Offering over 1,800 square feet of living space, this home features 3 bedrooms, 2 full bathrooms, 1 half bath, and breathtaking lake views right from your backyard. The updated eat-in kitchen is the heart of the home, showcasing a center island, newer

    Alexandria Sarki Keller Williams Realty

    402 Mountain Laurel Dr, Monroe, NY 10950
  • 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 $370,107

    Last Listing Agent Hershel Lowy Master Realty Group Inc.

    3911 Whispering Hills, Chester, NY 10918
    • 169 Creamery Pond Rd, Chester, NY 10918

      Est $686,342

      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 Days On Market

      Last Listing Agent Michele Tobin Keller Williams Realty

  • 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
  • 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 $626,608

    Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

    18 Grant Dr, Monroe, NY 10950
    • 189 Creamery Pond Rd, Chester, NY 10918

      Est $733,182

      Not Listed For Sale

      189 Creamery Pond Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,980 Sq Ft
      • Built 2004
      189 Creamery Pond Rd, Chester, NY 10918

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Patricia Brady Keller Williams Realty

  • 23 Pike Ct, Monroe, NY 10950
    23 Pike Ct, Monroe, NY 10950
    23 Pike Ct, Monroe, NY 10950
    /8

    $425,000

    • 3 Beds
    • 2 Baths
    • 2,460 Sq Ft

    23 Pike Ct, Monroe, NY 10950

    Welcome to 23 Pike Court. Unlock the potential of this spacious 3-bedroom, 2-bath raised ranch, which offers 2,460 square feet of living space on a generous .75 acre lot, giving you the space and flexibility to create something truly special. Perfect for an investor, contractor, or DIY enthusiast, this home is ready for someone with vision. While it needs work, it is move-in ready and offers an

    Patricia Sassi RE/MAX Benchmark Realty Group

    23 Pike Ct, Monroe, NY 10950
  • 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 $522,094

    Last Listing Agent Julie Klein BHG Real Estate Green Team

    80 Pewter Cir, Chester, NY 10918
    • 174 Creamery Pond Rd, Chester, NY 10918

      Est $698,858

      Not Listed For Sale

      174 Creamery Pond Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,608 Sq Ft
      • Built 2004
      174 Creamery Pond Rd, Chester, NY 10918

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Michele Tobin Keller Williams Realty

  • 1221 Whispering Hills, Chester, NY 10918
    1221 Whispering Hills, Chester, NY 10918
    1221 Whispering Hills, Chester, NY 10918
    /35

    $377,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft

    1221 Whispering Hills, Chester, NY 10918

    Update: Last buyers financing fell through so this wonderful property can be yours!! This is a must see! Will not last! Welcome to this beautifully renovated, spacious 3-bedroom, 2.5-bathroom, end-unit condo offering privacy, comfort, and elevated living in the desirable Whispering Hills community in picturesque Chester, NY! Perfectly positioned at the end of the row for added privacy and natural

    Malia Leonard BUY NY REALTY LLC

    1221 Whispering Hills, Chester, NY 10918

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