5,274

Homes in ZIP Code 10918

Section Image
  • 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
    • 243 Bull Mill Rd, Chester, NY 10918

      Est $620,166 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

      • 3% Above List Price
      • $297/SF
      • 11 Days On Market
      • Last Sold Price $600,000
      • Mar 18, 2024

      Last Listing Agent Debra gay Coldwell Banker Realty

  • 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
  • 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 $623,362

    Last Listing Agent Karen Gauvin Our House Real Estate Group

    40 Mountainside Dr, Chester, NY 10918
    • 119 Booth Rd, Chester, NY 10918

      Est $536,585 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

      • 2% Above List Price
      • $270/SF
      • 39 Days On Market
      • Last Sold Price $525,000
      • Nov 20, 2024

      Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  • 2 Virginia Ln, Goshen, NY 10924
    2 Virginia Ln, Goshen, NY 10924
    2 Virginia Ln, Goshen, NY 10924
    /4

    $350,000 Pending

    • Land
    • 5.4 Acres
    • $64,815 per Acre

    2 Virginia Ln, Goshen, NY 10924

    Town of Goshen 3 commercial lots with road frontage. Selling all 3 lots together. Most likely lot 2 is not buildable due to wetland constraints. Great location with easy build. There is no engineering available. Survey is old and not accurate. Very little infrastructure needed. See brochure in documents. Additional Information: SoilType:Unknown,

    Joe Distelburger Keller Williams Realty

    2 Virginia Ln, Goshen, NY 10924
  • 69 Shore Dr, Blooming Grove, NY 10914

    $487,000 Sold Apr 14, 2026

    69 Shore Dr, Blooming Grove, NY 10914

    • 1 Bed
    • 1 Bath
    • 1,192 Sq Ft
    • Built 1971

    Last Sold Summary

    • 8% Above List Price
    • $409/SF
    • 29 Days On Market

    Current Estimated Value $431,286

    Last Listing Agent Laura Denberg Corcoran Baer & McIntosh

    69 Shore Dr, Blooming Grove, NY 10914
    • 61 Nancy Ln, Chester, NY 10918

      Est $713,507 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

      • 10% Above List Price
      • $241/SF
      • 35 Days On Market
      • Last Sold Price $650,000
      • Oct 31, 2023

      Last Listing Agent Martha Randazzo Howard Hanna Rand Realty

  • 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
  • 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 $488,704

    Last Listing Agent Alexandra Zinko Century 21 Realty Center

    391 Bull Mill Rd, Chester, NY 10918
    • 88 Nancy Ln, Chester, NY 10918

      Est $605,032 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

      • 10% Above List Price
      • $199/SF
      • 44 Days On Market
      • Last Sold Price $549,675
      • May 20, 2024

      Last Listing Agent Christopher Rose REALHome Services & Solutions

  • 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
  • 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 $345,572

    Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

    1610 Whispering Hills, Chester, NY 10918
    • 38 Rebecca Rd, Chester, NY 10918

      Est $572,523 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

      • 3% Above List Price
      • $291/SF
      • 30 Days On Market
      • Last Sold Price $555,000
      • Dec 12, 2024

      Last Listing Agent Steve Esposito HomeSmart Homes & Estates

  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    /23

    $400,000

    • 3 Beds
    • 1 Bath
    • 1,561 Sq Ft

    33 Meadow Ave, Chester, NY 10918

    One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

    Ernie Acampora River Realty Services, Inc.

    33 Meadow Ave, 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 $317,531

    Last Listing Agent Jeffrey Morrissey Epique Realty

    2317 Whispering Hills, Chester, NY 10918
    • 32 Rebecca Rd, Chester, NY 10918

      Est $591,341 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

      • 11% Above List Price
      • $222/SF
      • 38 Days On Market
      • Last Sold Price $535,000
      • Dec 05, 2023

      Last Listing Agent Rosalie Cook Weichert Realtors

  • 1221 Whispering Hills, Chester, NY 10918
    1221 Whispering Hills, Chester, NY 10918
    1221 Whispering Hills, Chester, NY 10918
    /31

    $389,000

    • 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
  • 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 $417,904

    Last Listing Agent Pedro Garcia Curasi Realty, Inc.

    47 Greycourt Ave, Chester, NY 10918
    • 3 Stacey Ln, Chester, NY 10918

      Est $688,388 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

      • 14% Above List Price
      • $208/SF
      • 20 Days On Market
      • Last Sold Price $605,000
      • Aug 27, 2023

      Last Listing Agent Abraham Schwartz Priority Management

  • 53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    /48

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 4,467 Sq Ft

    53 Odyssey Dr, Chester, NY 10918

    Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

    Hilary Ryan Goldman Howard Hanna Rand Realty

    53 Odyssey Dr, 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 $860,399

    Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

    11 Saddle Hill Rd, Chester, NY 10918
    • 56 Goosepond Mountain Rd, Chester, NY 10918

      Est $557,213 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

      • 4% Above List Price
      • $174/SF
      • 34 Days On Market
      • Last Sold Price $535,000
      • Jul 19, 2024

      Last Listing Agent Linda Ross Linda C Ross Real Estate Inc

  • 4 Greycourt Rd, Chester, NY 10918
    4 Greycourt Rd, Chester, NY 10918
    4 Greycourt Rd, Chester, NY 10918
    /20

    $599,000 Pending

    • 3 Beds
    • 1.5 Baths

    4 Greycourt Rd, Chester, NY 10918

    Magnificent sprawling ranch situated on a park like setting with 2.80 acres with mature landscaping. This home features a spacious 2014 renovated EIK for entertaining with soft close cabinets, granite countertops, stainless steel appliances and an island cook top. Kitchen leads to an open concept large living /dining room combo with a large bay window for natural light with newly refinished

    Scott Loyer Coldwell Banker American Homes

    4 Greycourt 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 $584,766

    Last Listing Agent Kevin Tuhy Keller Williams Realty

    21 Jeffrey Dr, Chester, NY 10918
    • 137 Creamery Pond Rd, Chester, NY 10918

      Est $780,654 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

      • 4% Above List Price
      • $266/SF
      • 53 Days On Market
      • Last Sold Price $750,000
      • Apr 25, 2025

      Last Listing Agent John Stika Keller Williams Realty

  • 165 Round Hill Rd, Washingtonville, NY 10992
    165 Round Hill Rd, Washingtonville, NY 10992
    165 Round Hill Rd, Washingtonville, NY 10992
    /32

    $585,000 Pending

    • 4 Beds
    • 1.5 Baths
    • 2,191 Sq Ft

    165 Round Hill Rd, Washingtonville, NY 10992

    Welcome to 165 Round Hill Road, a beautiful traditional home set on a peaceful acre with mountain views that never get old. From the moment you arrive, you'll feel the care and history that's been poured into this home over the years. Inside, you'll find many original details that add character and warmth, including parquet flooring and stained glass windows flanking the front door. The family

    Victoria Wander Divine Realty NY, LLC

    165 Round Hill Rd, Washingtonville, NY 10992
  • 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 $510,543

    Last Listing Agent Nicholas Carbone HomeSmart Homes & Estates

    15 Mari Rd, Chester, NY 10918
    • 169 Creamery Pond Rd, Chester, NY 10918

      Est $661,299 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

      • 13% Above List Price
      • $240/SF
      • 16 Days On Market
      • Last Sold Price $585,000
      • Dec 13, 2023

      Last Listing Agent Michele Tobin Keller Williams Realty

  • 0 Main St, Chester, NY 10918
    0 Main St, Chester, NY 10918
    /2

    $500,000 Pending

    • Land
    • 36,098 Sq Ft
    • $603,355 per Acre

    0 Main St, Chester, NY 10918

    Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

    Claude Brischoux Keller Williams Realty

    0 Main St, Chester, NY 10918
  • 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 $407,522

    Last Listing Agent Harmoni VanEtten eXp Realty

    7 Garden St, Chester, NY 10918
    • 51 Pewter Cir, Chester, NY 10918

      Est $535,229 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
      • Sep 19, 2024

      Last Listing Agent Michele Tobin Keller Williams Realty

  • 8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    /11

    $349,999

    • Land
    • 4.9 Acres
    • $71,428 per Acre

    8 Camelback Rd, Chester, NY 10918

    Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

    James Feldhaus eXp Realty

    8 Camelback Rd, 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 $702,931

    Last Listing Agent Virginia Corbett eXp Realty

    2 Laura Dr, Chester, NY 10918
    • 53 Pewter Cir, Chester, NY 10918

      Est $538,269 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

      • 4% Above List Price
      • $235/SF
      • 33 Days On Market
      • Last Sold Price $520,000
      • May 28, 2024

      Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  • 2 Imperial Park, Chester, NY 10918
    2 Imperial Park, Chester, NY 10918
    2 Imperial Park, Chester, NY 10918
    /9

    $149,900

    • Land
    • 8,873 Sq Ft
    • $735,886 per Acre

    2 Imperial Park, Chester, NY 10918

    Large 2 story storage barn approx 80' x 30' with silo for sale in the Town of Chester. 5 garage doors - 4 are 6 feet high, 1 door is 7 foot high with loading dock. Plenty of storage on first and second level. Small office. Has electric, but is turned off. Has well water, but no septic - lot is too small - only .20 acre. Not a buildable lot. Barn was subdivided off from neighboring farm. Has loft

    William Scolza HomeSmart Homes & Estates

    2 Imperial Park, 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 $375,571

    Last Listing Agent Hershel Lowy Master Realty Group Inc.

    3911 Whispering Hills, Chester, NY 10918
    • 15 Pewter Cir, Chester, NY 10918

      Est $693,702 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
      • Jun 13, 2024

      Last Listing Agent Jennifer Connolly BHHS Gross & Jansen

  • 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
  • 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 $551,471

    Last Listing Agent Luanne McGann Century 21 Full Service Realty

    16 Ayr Rd, Chester, NY 10918

Showing Results 121 - 160, Page 4 of 18

New York Orange County Chester 10918

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group