5,093

Homes in ZIP Code 10918

Section Image
  • 25 High St, Chester, NY 10918

    $505,000

    Sold Feb 26, 2026

    25 High St, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,898 Sq Ft
    • Built 1850

    Last Sold Summary

    • 4% Below List Price
    • $174/SF
    • 192 Days On Market

    Current Estimated Value $527,927

    Last Listing Agent Alicia Goldman Christie's Int. Real Estate

    25 High St, Chester, NY 10918
    • 15 Park Dr, Chester, NY 10918

      Est $467,262

      Not Listed For Sale

      15 Park Dr, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,724 Sq Ft
      • Built 1968
      15 Park Dr, Chester, NY 10918

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Krista Fontenelle-Garcia Batiz Exit Realty DKC

  • 7 Hambletonian Ave, Chester, NY 10918
    7 Hambletonian Ave, Chester, NY 10918
    7 Hambletonian Ave, Chester, NY 10918
    /26

    $379,900

    $45K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 1,026 Sq Ft

    7 Hambletonian Ave, Chester, NY 10918

    Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay

    William Scolza HomeSmart Homes & Estates

    7 Hambletonian Ave, Chester, NY 10918
  • 2913 Whispering Hills Unit 595, Chester, NY 10918

    $288,000

    Sold Apr 17, 2026

    2913 Whispering Hills Unit 595, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Above List Price
    • $266/SF
    • 18 Days On Market

    Current Estimated Value $288,400

    Last Listing Agent Devon King HomeSmart Homes & Estates

    2913 Whispering Hills Unit 595, Chester, NY 10918
    • 52 Surrey Rd, Chester, NY 10918

      Est $450,990

      Not Listed For Sale

      52 Surrey Rd, Chester, NY 10918

      • 4 Beds
      • 2 Baths
      • 1,780 Sq Ft
      • Built 1969
      52 Surrey Rd, Chester, NY 10918

      Last Sold Summary

      • 104 Days On Market

      Last Listing Agent Brian Caplicki KW Hudson Valley United

  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    /21

    $370,000

    Pending
    • 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
  • 2203 Whispering Hills, Chester, NY 10918

    $348,000

    Sold Jun 11, 2026

    2203 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 6% Below List Price
    • $261/SF
    • 47 Days On Market

    Current Estimated Value $351,372

    Last Listing Agent Marie Altieri Howard Hanna Rand Realty

    2203 Whispering Hills, Chester, NY 10918
    • 22 Trotting Dr, Chester, NY 10918

      Est $397,700

      Not Listed For Sale

      22 Trotting Dr, Chester, NY 10918

      • 3 Beds
      • 1 Bath
      • 1,024 Sq Ft
      • Built 1968
      22 Trotting Dr, Chester, NY 10918

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Diane Blanton Howard Hanna Rand Realty

  • 49 Stone Mountain Trail, Chester, NY 10918
    49 Stone Mountain Trail, Chester, NY 10918
    49 Stone Mountain Trail, Chester, NY 10918
    /35

    $875,000

    • 4 Beds
    • 2.5 Baths
    • 3,656 Sq Ft

    49 Stone Mountain Trail, Chester, NY 10918

    Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

    Arya Rabinovits eRealty Advisors, Inc

    49 Stone Mountain Trail, Chester, NY 10918
  • 19 Lake Station Rd, Warwick, NY 10990

    $700,000

    Sold Oct 30, 2025

    19 Lake Station Rd, Warwick, NY 10990

    • 4 Beds
    • 1.5 Baths
    • 3,288 Sq Ft
    • Built 1865

    Last Sold Summary

    • $213/SF
    • 58 Days On Market

    Current Estimated Value $734,388

    Last Listing Agent Tammy Scotto Keller Williams Realty

    19 Lake Station Rd, Warwick, NY 10990
    • 21 Park Dr, Chester, NY 10918

      Est $503,912

      Not Listed For Sale

      21 Park Dr, Chester, NY 10918

      • 4 Beds
      • 2 Baths
      • 1,800 Sq Ft
      • Built 1967
      21 Park Dr, Chester, NY 10918

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Colin Seitz RE/MAX Benchmark Realty Group

  • 5 Hilltop Ln, Chester, NY 10918
    5 Hilltop Ln, Chester, NY 10918
    5 Hilltop Ln, Chester, NY 10918
    /5

    $850,000

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

    5 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail

    Moshe Kaufman MK Realty Inc

    5 Hilltop Ln, Chester, NY 10918
  • 3601 Whispering Hills, Chester, NY 10918

    $296,000

    Sold Jun 05, 2026

    3601 Whispering Hills, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1990

    Last Sold Summary

    • 3% Below List Price
    • $273/SF
    • 23 Days On Market

    Current Estimated Value $296,837

    Last Listing Agent Janet Rendle Weichert Realtors

    3601 Whispering Hills, Chester, NY 10918
    • 27 Natures Trail, Chester, NY 10918

      Est $607,043

      Not Listed For Sale

      27 Natures Trail, Chester, NY 10918

      • 4 Beds
      • 2 Baths
      • 2,420 Sq Ft
      • Built 1966
      27 Natures Trail, Chester, NY 10918

      Last Sold Summary

      • 78 Days On Market

      Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

  • 121 Conklingtown Rd, Chester, NY 10918
    121 Conklingtown Rd, Chester, NY 10918
    121 Conklingtown Rd, Chester, NY 10918
    /50

    $749,000

    • 4 Beds
    • 2.5 Baths
    • 2,599 Sq Ft

    121 Conklingtown Rd, Chester, NY 10918

    Imagine coming home to a beautifully maintained and upgraded property designed for comfort, entertaining, and enjoying the outdoors. This home features a high-ceiling foyer flooded with natural sunlight, a granite kitchen with a tiled backsplash, a gas fireplace, extra living and dining room space, 9-foot ceilings, hardwood flooring, and central AC throughout. Step outside to an oversized double

    Chaim Weiss MS Realty Group USA, Inc

    121 Conklingtown Rd, Chester, NY 10918
  • 2503 Whispering Hills, Chester, NY 10918

    $340,000

    Sold Oct 15, 2025

    2503 Whispering Hills, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,316 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Below List Price
    • $258/SF
    • 59 Days On Market

    Current Estimated Value $347,984

    Last Listing Agent Sonia Gonzalez HomeSmart Homes & Estates

    2503 Whispering Hills, Chester, NY 10918
    • 2 Fields Ln, Chester, NY 10918

      Est $583,243

      Not Listed For Sale

      2 Fields Ln, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 2,604 Sq Ft
      • Built 1972
      2 Fields Ln, Chester, NY 10918

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Margaret Galatro ARC Realty 1 in Sales

  • 1 Hilltop Ln, Chester, NY 10918
    1 Hilltop Ln, Chester, NY 10918
    /2

    $750,000

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    1 Hilltop Ln, Chester, NY 10918

    Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

    Moshe Kaufman MK Realty Inc

    1 Hilltop Ln, Chester, NY 10918
  • 16 Oxford Springs Rd, Chester, NY 10918

    $725,000

    Sold May 27, 2026

    16 Oxford Springs Rd, Chester, NY 10918

    • 3 Beds
    • 3 Baths
    • 2,870 Sq Ft
    • Built 1988

    Last Sold Summary

    • 7% Below List Price
    • $253/SF
    • 117 Days On Market

    Current Estimated Value $716,894

    Last Listing Agent Jennifer Gold RE/MAX Benchmark Realty Group

    16 Oxford Springs Rd, Chester, NY 10918
    • 351 Sugarloaf Mountain Rd, Chester, NY 10918

      Est $538,227

      Not Listed For Sale

      351 Sugarloaf Mountain Rd, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,562 Sq Ft
      • Built 1993
      351 Sugarloaf Mountain Rd, Chester, NY 10918

      Last Sold Summary

      • 28 Days On Market

      Last Listing Agent Kasey Malone BHG Real Estate Green Team

  • 11 Old Dominion Rd, Blooming Grove, NY 10914
    11 Old Dominion Rd, Blooming Grove, NY 10914
    11 Old Dominion Rd, Blooming Grove, NY 10914
    /28

    $724,000

    Pending
    • 4 Beds
    • 2.5 Baths
    • 2,547 Sq Ft

    11 Old Dominion Rd, Blooming Grove, NY 10914

    Nestled on a stunning, level homesite, this classic Colonial offers the perfect blend of privacy, space, and timeless charm. The beautifully landscaped grounds, expansive front yard, and long private driveway create an impressive first impression. Enjoy peaceful surroundings, mature trees, and picturesque views while still being conveniently located to local amenities. With generous outdoor space

    Lazar Schvimmer Mount Realty

    11 Old Dominion Rd, Blooming Grove, NY 10914
  • 2409 Whispering Hills, Chester, NY 10918

    $365,000

    Sold Nov 14, 2025

    2409 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 2% Above List Price
    • $274/SF
    • 26 Days On Market

    Current Estimated Value $367,013

    Last Listing Agent Linda Clark Hudson Valley Griffith

    2409 Whispering Hills, Chester, NY 10918
    • 110 Ridge Rd, Chester, NY 10918

      Est $991,541

      Not Listed For Sale

      110 Ridge Rd, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 4,190 Sq Ft
      • Built 1995
      110 Ridge Rd, Chester, NY 10918

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Teresa Gavan BHG Real Estate Green Team

  • 1005 Whispering Hills, Chester, NY 10918
    1005 Whispering Hills, Chester, NY 10918
    1005 Whispering Hills, Chester, NY 10918
    /28

    $290,000

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

    1005 Whispering Hills, Chester, NY 10918

    Welcome to Whispering Hills! This spacious two-level, 2-bedroom, 1.5-bath condo with a 1-car garage features a great combination of updates and an ideal commuter location. Step inside to a freshly painted interior featuring an updated kitchen and bathrooms. The inviting living room features a fireplace and sliders leading to a private patio, perfect for relaxing and enjoying the outdoors.

    Kristie Jacques Century 21 Full Service Realty

    1005 Whispering Hills, Chester, NY 10918
  • 48 Brennan Ct, Chester, NY 10918

    $740,000

    Sold Nov 21, 2025

    48 Brennan Ct, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 3,063 Sq Ft
    • Built 2006

    Last Sold Summary

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

    Current Estimated Value $750,207

    Last Listing Agent Claude Brischoux Keller Williams Realty

    48 Brennan Ct, Chester, NY 10918
    • 392 Bellvale Rd, Chester, NY 10918

      Est $755,572

      Not Listed For Sale

      392 Bellvale Rd, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,900 Sq Ft
      • Built 1993
      392 Bellvale Rd, Chester, NY 10918

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Mitchell Kass eXp Realty

  • 0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
    /2

    $1,700,000

    • Land
    • 46.5 Acres
    • $36,559 per Acre

    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914

    Incredible opportunity to own approximately 55 acres of land being offered as a package with two adjoining parcels. This expansive property offers endless potential for investors, builders, or those seeking a private estate or recreational retreat. Preliminary information suggests the property may have the potential for approximately 400,000 square feet of warehouse space. Both parcels are being

    Lazar Schvimmer Mount Realty

    0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
  • 17 Woodridge Dr, Chester, NY 10918

    $625,000

    Sold Aug 17, 2026

    17 Woodridge Dr, Chester, NY 10918

    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft
    • Built 1998

    Last Sold Summary

    • 17% Below List Price
    • $248/SF
    • 85 Days On Market

    Current Estimated Value $632,048

    Last Listing Agent Sharon Kushner eXp Realty

    17 Woodridge Dr, Chester, NY 10918
    • 81 Hambletonian Rd, Chester, NY 10918

      Est $630,563

      Not Listed For Sale

      81 Hambletonian Rd, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,938 Sq Ft
      • Built 2002
      81 Hambletonian Rd, Chester, NY 10918

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Dean Diltz Keller Williams Realty

  • 2820 Whispering Hills, Chester, NY 10918
    2820 Whispering Hills, Chester, NY 10918
    2820 Whispering Hills, Chester, NY 10918
    /32

    $319,900

    $4K PRICE INCREASE Pending
    • 2 Beds
    • 1.5 Baths
    • 1,072 Sq Ft

    2820 Whispering Hills, Chester, NY 10918

    Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

    Anne Marie Scouarnec R2M Realty Inc.

    2820 Whispering Hills, Chester, NY 10918
  • 1 Boville Ct, Chester, NY 10918

    $700,000

    Sold Sep 15, 2026

    1 Boville Ct, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft
    • Built 2022

    Last Sold Summary

    • $269/SF
    • 2 Days On Market

    Last Listing Agent Dovid Hoffman MK Realty Inc

    1 Boville Ct, Chester, NY 10918
    • 63 Hambletonian Rd, Chester, NY 10918

      Est $664,121

      Not Listed For Sale

      63 Hambletonian Rd, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,310 Sq Ft
      • Built 1997
      63 Hambletonian Rd, Chester, NY 10918

      Last Sold Summary

      • 25 Days On Market

      Last Listing Agent Dean Diltz Keller Williams Realty

  • 2007 Whispering Hills, Chester, NY 10918
    2007 Whispering Hills, Chester, NY 10918
    2007 Whispering Hills, Chester, NY 10918
    /44

    $279,999

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,086 Sq Ft

    2007 Whispering Hills, Chester, NY 10918

    Welcome to 2007 Whispering Hills Drive! This 2-bedroom, 1.5-bath condo offers comfortable living in one of Chester’s most desirable communities.The main level features a spacious living room with a real wood-burning fireplace, a dining area, and a kitchen with stainless steel appliances. Luxury vinyl plank flooring adds a modern touch throughout the main living areas. Upstairs, you’ll

    Philip Szumlaski Keller Williams Realty

    2007 Whispering Hills, Chester, NY 10918
  • 5 Roggia Rd, Chester, NY 10918

    $450,000

    Sold Aug 04, 2026

    5 Roggia Rd, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft
    • Built 1951

    Last Sold Summary

    • $239/SF
    • 31 Days On Market

    Current Estimated Value $445,012

    Last Listing Agent Nazma Sooknanan Nazma Real Estate LLC

    5 Roggia Rd, Chester, NY 10918
    • 15 Banker Dr, Chester, NY 10918

      Est $789,998

      Not Listed For Sale

      15 Banker Dr, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 2,396 Sq Ft
      • Built 2000
      15 Banker Dr, Chester, NY 10918

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  • 2604 Whispering Hills, Chester, NY 10918
    2604 Whispering Hills, Chester, NY 10918
    2604 Whispering Hills, Chester, NY 10918
    /35

    $350,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 1,086 Sq Ft

    2604 Whispering Hills, Chester, NY 10918

    Welcome to 2604 Whispering Hills! This beautifully maintained, move-in-ready 3-bedroom, 2.5-bath townhome offers comfort, style, and numerous recent updates. Major improvements completed within the last five years include new windows, furnace, water heater, washer, and dryer, providing peace of mind for the new owner. The bright, spacious floor plan is perfect for everyday living and

    Sonia Gonzalez HomeSmart Homes & Estates

    2604 Whispering Hills, Chester, NY 10918
  • 4309 Whispering Hills Dr, Chester, NY 10918

    $375,000

    Sold Dec 11, 2025

    4309 Whispering Hills Dr, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,355 Sq Ft
    • Built 1989

    Last Sold Summary

    • $277/SF
    • 27 Days On Market

    Current Estimated Value $378,329

    Last Listing Agent Sean Israelski Howard Hanna Rand Realty

    4309 Whispering Hills Dr, Chester, NY 10918
    • 1301 Kings Hwy, Chester, NY 10918

      Est $646,635

      Not Listed For Sale

      1301 Kings Hwy, Chester, NY 10918

      • 4 Beds
      • 2.5 Baths
      • 2,676 Sq Ft
      • Built 1835
      1301 Kings Hwy, Chester, NY 10918

      Last Sold Summary

      • 146 Days On Market

      Last Listing Agent Susan Walski HomeSmart Homes & Estates

  • 2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    /36

    $875,000

    • 3 Beds
    • 2.5 Baths
    • 2,302 Sq Ft

    2 Pine Hill Rd, Chester, NY 10918

    The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the

    Richard Ellis Ellis Sotheby's Intl Realty

    2 Pine Hill Rd, Chester, NY 10918
  • 1 N Hudson St Unit N, Chester, NY 10918

    $500,000

    Sold Aug 12, 2026

    1 N Hudson St Unit N, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,778 Sq Ft
    • Built 1953

    Last Sold Summary

    • $281/SF
    • 20 Days On Market

    Current Estimated Value $474,210

    Last Listing Agent Alison Orlando KW Hudson Valley United

    1 N Hudson St Unit N, Chester, NY 10918

Showing Results 241 - 280, Page 7 of 18

New York Orange County Chester

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