6,751

Chester, NY Homes

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  • /41

    $1,139,900

    $20K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 4,624 Sq Ft

    16 Lori Ln, Chester, NY 10918

    Welcome to Chester, NY, a resort-style luxury colonial set on a private 1.1-acre cul-de-sac lot in the Monroe-Woodbury area of Orange County. This custom residence delivers the space, craftsmanship, and lifestyle today's relocation and move-up buyers are searching for, with approximately 4,624 square feet, refined architectural detail, mountain views, and seamless indoor-outdoor living. From the

    Agent Photo

    Randolph Rogers

    eXp Realty

    16 Lori Ln, Chester, NY 10918
  • /4

    $4,200 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,894 Sq Ft
    • House for Rent

    3 Brookside Ave, Chester, NY 10918

    Come see this mixed use residential and commercial property for rent. Enjoy the benefits of working from home as you can have your business in the same home. 3 bed 3 bath home in Chester. Enjoy the ample amount of parking available, fitting well over 10 cars on your lot. Call today for a showing

    Agent Photo

    Joel Ayala

    HomeSmart Homes & Estates

    3 Brookside Ave, Chester, NY 10918
  • 10 Damian Ct, Chester, NY 10918

    $1,225,000

    Sold Apr 17, 2026

    10 Damian Ct, Chester, NY 10918

    • 11 Beds
    • 6.5 Baths
    • 4,327 Sq Ft
    • Built 2004

    Last Sold Summary

    • 11% Below List Price
    • $283/SF
    • 47 Days On Market

    Current Estimated Value $1,216,706

    Last Listing Agent Elimelech Kremer MS Realty Group USA, Inc

    10 Damian Ct, Chester, NY 10918
    • 10 El Dorado Trail, Chester, NY 10918

      Est $266,799

      Not Listed For Sale

      10 El Dorado Trail, Chester, NY 10918

      10 El Dorado Trail, Chester, NY 10918

      Last Sold Summary

      • 152 Days On Market

      Last Listing Agent Lisandra Rivera Keller Williams Realty

  • /48

    $1,100,000

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

    53 Gibson Hill Rd, Chester, NY 10918

    Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene

    Agent Photo

    Ammar Iqbal

    eXp Realty

    53 Gibson Hill Rd, Chester, NY 10918
  • /20

    $16,380

    Total Monthly Price

    • 7 Beds
    • 6 Baths
    • Condo for Rent

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918

    The advertised rate of $16,380/month is the lowest available price, based on a 30 day(s) stay with a move-in date of January 11, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    45 Conklingtown Rd Unit SI ID1466647P, Chester, NY 10918
  • 25 Sugarloaf Mountain Rd, Chester, NY 10918

    $635,000

    Sold Jun 22, 2026

    25 Sugarloaf Mountain Rd, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,954 Sq Ft
    • Built 1999

    Last Sold Summary

    • $325/SF
    • 29 Days On Market

    Current Estimated Value $630,676

    Last Listing Agent Frank Muccari Cronin & Company Real Estate

    25 Sugarloaf Mountain Rd, Chester, NY 10918
    • 495 Laroe Rd, Chester, NY 10918

      Est $483,498

      Not Listed For Sale

      495 Laroe Rd, Chester, NY 10918

      • 3 Beds
      • Built 2025
      495 Laroe Rd, Chester, NY 10918

      Last Sold Summary

      • 170 Days On Market

      Last Listing Agent Dylan Piazza Howard Hanna Rand Realty

  • /37

    $789,900

    Open Sun 12PM - 2PM
    • 5 Beds
    • 4 Baths
    • 4,697 Sq Ft

    19 Grand View Terrace, Chester, NY 10918

    Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests. The generous interior features multiple living

    Agent Photo

    Randolph Rogers

    eXp Realty

    19 Grand View Terrace, Chester, NY 10918
  • /20

    $2,300 Per Month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    82 High St Unit 5, Chester, NY 10918

    Fresh carpet has just been laid throughout this luminous top-floor penthouse, where an open layout and abundant sunshine create an inviting canvas for daily life. At 900 square feet, this 2-bedroom, 1-bath home balances spaciousness with a cozy, lived-in warmth. Cooks will appreciate the updated kitchen, outfitted with a new stainless steel refrigerator and dishwasher that bring both style and

    Agent Photo

    Ourania Pizzolato

    Weichert Realtors

    82 High St Unit 5, Chester, NY 10918
  • /9

    $43,000

    Sold Oct 31, 2025

    L17 Vanderwalker Rd, Chester, NY 12817

    • Land
    • 4 Acres
    • $10,750 per Acre

    Last Sold Summary

    • 12% Below List Price
    • 5 Days On Market

    Last Listing Agent Zachary Layton Four Seasons Sotheby's International Realty

    L17 Vanderwalker Rd, Chester, NY 12817
    • 303 Sugarloaf Mountain Rd, Chester, NY 10918

      Est $750,246

      Not Listed For Sale

      303 Sugarloaf Mountain Rd, Chester, NY 10918

      • 4 Beds
      • 3 Baths
      • 2,287 Sq Ft
      • Built 2024
      303 Sugarloaf Mountain Rd, Chester, NY 10918

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Courtney Tablante Keller Williams Realty

  • /22

    $329,000

    Pending
    • 2 Beds
    • 1.5 Baths
    • 1,294 Sq Ft

    4118 Whispering Hills, Chester, NY 10918

    Beautifully maintained two bedroom condo with a two car garage in an excellent location within the highly desirable Whispering Hills community. Updated kitchen and newer flooring on the main level. Wood burning fireplace in the spacious living room. Sliding door from the dining area to the patio. The primary bedroom with tall vaulted ceilings has a large walk-in closet with custom

    Agent Photo

    Joseph Paoli

    Howard Hanna Rand Realty

    4118 Whispering Hills, Chester, NY 10918
  • /10

    $1,750 Per Month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    105 Pine Hollow Way, Chester, NY 10918

    Welcome to the desirable Pine Hollow Complex in Chester! This spacious one-bedroom, one-bath residence offers a bright, open-concept floor plan filled with natural light, creating a warm and inviting atmosphere. The open living area features a gas fireplace and central air conditioning, providing comfort throughout every season. The generously sized bedroom offers generous closet space, while a

    Kristie Jacques Century 21 Full Service Realty

    105 Pine Hollow Way, Chester, NY 10918
  • 2912 Whispering Hills, Chester, NY 10918

    $320,000

    Sold Mar 11, 2026

    2912 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 5% Above List Price
    • $295/SF
    • 19 Days On Market

    Current Estimated Value $313,526

    Last Listing Agent Rebecca Matta-Candela Keller Williams Realty

    2912 Whispering Hills, Chester, NY 10918
    • 30 Mount Ridge Ct, Monroe, NY 10950

      Est $119,470

      Not Listed For Sale

      30 Mount Ridge Ct, Monroe, NY 10950

      30 Mount Ridge Ct, Monroe, NY 10950

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  • /35

    $399,999

    Pre-Foreclosure
    • 4 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    241 Meadow Ave, Chester, NY 10918

    Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship.Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming

    Agent Photo

    Chativa Bowen

    Keller Williams Realty

    241 Meadow Ave, Chester, NY 10918
  • /14

    $2,350 Per Month

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Condo for Rent

    4013 Whispering Hills, Chester, NY 10918

    Welcome to this well-maintained 2-bedroom, 1 bath townhouse located in Whispering Hills. This unit features an open layout with laminate flooring throughout the main living areas. The living room includes a fireplace and a slider to your own private deck. Enjoy a functional kitchen and dining room that makes everyday living and hosting a breeze. Down the hallway an updated bathroom and two

    Joseph Trifono HomeSmart Homes & Estates

    4013 Whispering Hills, Chester, NY 10918
  • 2104 Whispering Hills, Chester, NY 10918

    $260,000

    Sold Mar 11, 2026

    2104 Whispering Hills, Chester, NY 10918

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

    Last Sold Summary

    • 13% Below List Price
    • $195/SF
    • 24 Days On Market

    Current Estimated Value $283,151

    Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

    2104 Whispering Hills, Chester, NY 10918
    • 154 Hambletonian Rd, Chester, NY 10918

      Est $1,294,943

      Not Listed For Sale

      154 Hambletonian Rd, Chester, NY 10918

      • 4 Beds
      • 3.5 Baths
      • 4,350 Sq Ft
      • Built 2013
      154 Hambletonian Rd, Chester, NY 10918

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Claudia Lepore Keller Williams Realty

  • /38

    $499,900

    Pending
    • 3 Beds
    • 2 Baths
    • 1,778 Sq Ft

    1 N Hudson St Unit N, Chester, NY 10918

    Welcome home to 1 North Hudson Street — a meticulously maintained Cape Cod that is truly beautiful inside and out. From the moment you arrive, the curb appeal speaks for itself. Lush, manicured grounds frame this charming brick and white-sided Cape Cod, where mature trees, vibrant landscaping, and a stunning bluestone patio set the stage for a lifestyle of comfort and ease. Whether you're hosting

    Agent Photo

    Alison Orlando

    KW Hudson Valley United

    1 N Hudson St Unit N, Chester, NY 10918
  • /22

    $3,250 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,699 Sq Ft
    • Townhouse for Rent

    256 Heritage Ln, Monroe, NY 10950

    Monroe, NY - Spacious, two-level townhouse end unit. First floor features living room/dining area, kitchen with dinette area, half bath, laundry room & garage. Top level contains master bedroom suite with full bath & walk-in closet, second bedroom, third bedroom, second full bathroom and hallway walk-in closet. Additional features: Young carpeting, entry way flooring, butcher block counter top &

    Frank Gomez HomeSmart Homes & Estates

    256 Heritage Ln, Monroe, NY 10950
  • 52 Wilson Rd, Monroe, NY 10950

    $588,000

    Sold Aug 07, 2026

    52 Wilson Rd, Monroe, NY 10950

    • 4 Beds
    • 3 Baths
    • 1,846 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Above List Price
    • $319/SF
    • 22 Days On Market

    Current Estimated Value $557,558

    Last Listing Agent Claudia Lepore Keller Williams Realty

    52 Wilson Rd, Monroe, NY 10950
    • /12

      Not Listed For Sale

      L47 Cobble Creek Rd, Chester, NY 12853

      L47 Cobble Creek Rd, Chester, NY 12853

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Sara Gallipo-Sammis Century 21 Adirondacks

  • /5

    $49,900

    • Land
    • 1.76 Acres
    • $28,352 per Acre

    Unlisted Address

    Opportunity awaits on this 1.76-acre building lot in the heart of the Adirondacks, just minutes from Gore Mountain. Whether you're dreaming of an affordable year-round home or the perfect basecamp for skiing, hiking, mountain biking, snowmobiling, and everything the Adirondacks have to offer, this property provides an excellent starting point. Existing improvements include electric service, as

    Agent Photo

    Sean Rogge

    Howard Hanna Capital Inc

    Unlisted Address
  • /6

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 1,316 Sq Ft
    • Condo for Rent

    3102 Whispering Hills Unit 678, Chester, NY 10918

    CURRENT TENANTE IS SEEKING A ROOMMATE. Looking to rent a fully furnished 1 bedroom 1 bath. This is within the 3 bedroom unit and common area/kitchen will be shared with the owner. This is a fully air conditioned unit. This would be a month-to-month tenancy and owner is very flexible. Assigned parking spot is available with access to the swimming pool, common area and gym. Located in Chester, NY

    Stephanie Landeck BHG Real Estate Green Team

    3102 Whispering Hills Unit 678, Chester, NY 10918
  • 3308 Whispering Hills Dr, Chester, NY 10918

    $290,000

    Sold Apr 09, 2026

    3308 Whispering Hills Dr, Chester, NY 10918

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

    Last Sold Summary

    • 3% Below List Price
    • $271/SF
    • 39 Days On Market

    Current Estimated Value $294,428

    Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

    3308 Whispering Hills Dr, Chester, NY 10918
    • 4401 Whispering Hills Dr, Chester, NY 10918

      Est $309,698

      Not Listed For Sale

      4401 Whispering Hills Dr, Chester, NY 10918

      • 2 Beds
      • 1 Bath
      • 1,118 Sq Ft
      • Built 1989
      4401 Whispering Hills Dr, Chester, NY 10918

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty

  • /3

    $48,000

    • Land
    • 3.6 Acres
    • $13,333 per Acre

    1414 N Gore Rd, Chester, NY 12817

    North Gore Lot - Come build your dream on home this 3.6 acre wooded lot with power available roadside and perc test completed. Secluded location, yet only 15 minutes to Gore Mountain and 10 minutes to Minerva Beach with abundant outdoor recreation opportunities.

    Agent Photo

    Amanda Gadway

    Gadway Realty

    1414 N Gore Rd, Chester, NY 12817
  • 98 High St, Chester, NY 10918

    $323,500

    Sold Aug 11, 2025

    98 High St, Chester, NY 10918

    • 4 Beds
    • 1.5 Baths
    • 1,360 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Below List Price
    • $238/SF
    • 35 Days On Market

    Current Estimated Value $348,393

    Last Listing Agent Zachary Foley eXp Realty

    98 High St, Chester, NY 10918
    • 4120 Whispering Hills Dr, Chester, NY 10918

      Not Listed For Sale

      4120 Whispering Hills Dr, Chester, NY 10918

      • 2 Beds
      • 1.5 Baths
      • 1,282 Sq Ft
      • Built 1989
      4120 Whispering Hills Dr, Chester, NY 10918

      Last Sold Summary

      • 69 Days On Market

      Last Listing Agent Joseph Paoli Howard Hanna Rand Realty

  • /50

    $990,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,955 Sq Ft

    1 Oakland Ave, Chester, NY 10918

    Welcome to Brook Farm - Village of Chester, New York - Circa 1851 - 6.8 Acres. There's a moment, just after you turn onto Main Street and the house comes into view above the lawn, when you understand that this is not an ordinary property. The covered porch stretches wide across the front, the slate roof catches the afternoon light, and the whole thing sits there with the quiet confidence of

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    1 Oakland Ave, Chester, NY 10918
  • 44 Cedar Pond Ln, Chester, NY 10918

    $610,000

    Sold Mar 12, 2026

    44 Cedar Pond Ln, Chester, NY 10918

    • 3 Beds
    • 2 Baths
    • 1,876 Sq Ft
    • Built 1991

    Last Sold Summary

    • 2% Above List Price
    • $325/SF
    • 48 Days On Market

    Current Estimated Value $655,404

    Last Listing Agent Ammar Iqbal eXp Realty

    44 Cedar Pond Ln, Chester, NY 10918
    • 3111 Whispering Hills Dr, Chester, NY 10918

      Not Listed For Sale

      3111 Whispering Hills Dr, Chester, NY 10918

      • 3 Beds
      • 2 Baths
      • 1,316 Sq Ft
      • Built 1987
      3111 Whispering Hills Dr, Chester, NY 10918

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty

  • /18

    $399,000

    • Land
    • 46 Acres
    • $8,674 per Acre

    492 Black Meadow Rd, Chester, NY 10918

    Rare opportunity to own approximately 46 acres in the desirable Black Meadow Road area of Chester, New York. Tucked privately behind a subdivision entrance at the end of a cul-de-sac, this parcel offers a peaceful natural setting surrounded by mature woods, wetlands, scenic surroundings, and abundant wildlife. Ideal for recreational use including hiking, hunting, nature walks, bird watching,

    Agent Photo

    Ewa Kusmierek

    eXp Realty

    492 Black Meadow Rd, Chester, NY 10918
  • 2812 Whispering Hills Unit 577, Chester, NY 10918

    $320,000

    Sold Feb 13, 2026

    2812 Whispering Hills Unit 577, Chester, NY 10918

    • 2 Beds
    • 1 Bath
    • 1,084 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Above List Price
    • $295/SF
    • 22 Days On Market

    Current Estimated Value $316,294

    Last Listing Agent Kathy White Exit Realty Connections

    2812 Whispering Hills Unit 577, Chester, NY 10918
    • 397 Bellvale Rd, Chester, NY 10918

      Est $503,557

      Not Listed For Sale

      397 Bellvale Rd, Chester, NY 10918

      • 2 Beds
      • 2 Baths
      • 1,452 Sq Ft
      • Built 1983
      397 Bellvale Rd, Chester, NY 10918

      Last Sold Summary

      • 45 Days On Market

      Last Listing Agent Juan Bautista Serhant LLC

  • /48

    $899,000

    $86K PRICE DROP Pending
    • 5 Beds
    • 3.5 Baths
    • 3,764 Sq Ft

    86 Long Vista Ln, Chester, NY 10918

    Now offered at $899,000. Settle in before the new school year and start living your best life here. Privately set on over 5 scenic acres within the Warwick School District and just one hour from Manhattan, this beautifully maintained Colonial offers the lifestyle buyers are searching for. Privacy, acreage, breathtaking mountain views, resort-style outdoor living, flexible space, and a convenient

    Agent Photo

    Jennifer DiCostanzo

    RE/MAX Town & Country

    86 Long Vista Ln, Chester, NY 10918
  • 4703 Whispering Hills Dr, Chester, NY 10918

    $382,000

    Sold Jan 12, 2026

    4703 Whispering Hills Dr, Chester, NY 10918

    • 3 Beds
    • 2.5 Baths
    • 1,331 Sq Ft
    • Built 1991

    Last Sold Summary

    • 4% Above List Price
    • $287/SF
    • 61 Days On Market

    Current Estimated Value $372,671

    Last Listing Agent Erin Connolly-Frontino Artisan Realty

    4703 Whispering Hills Dr, Chester, NY 10918
    • 1110 Whispering Hills Dr, Chester, NY 10918

      Est $354,867

      Not Listed For Sale

      1110 Whispering Hills Dr, Chester, NY 10918

      • 3 Beds
      • 2.5 Baths
      • 1,331 Sq Ft
      • Built 1985
      1110 Whispering Hills Dr, Chester, NY 10918

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Yalitza Sepulveda Keller Williams Realty

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$498,500
Median Single Family Sale Price
$657,500
Median Townhouse Sale Price
$335,000
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$274
Number of Homes for Sale
65
Last 12 months Home Sales
84
Months of Supply
9.30
Median List Price
$587,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-5%
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