6

Chester, NY Homes for Sale under $1,500,000

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  • /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
  • /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
  • /32

    $1,199,000

    $100K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 5,712 Sq Ft

    16 Sunset Ridge, Monroe, NY 10950

    NEW PRICE! Ready to sell! Highly motivated seller. Sold as-is. Recent updates include fresh paint in select areas and new pavers for enhanced curb appeal. Located approximately one hour from NYC with convenient access to major roadways.Welcome to this secluded Colonial in desirable Trout Brook Estates, set on nearly 6 private acres with over 5,700 sq ft of living space. This spacious

    Carmela Lopez Borrazas Serhant LLC

    16 Sunset Ridge, Monroe, NY 10950
  • /38

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 2,711 Sq Ft

    63 Whitetail Run, Chester, NY 10918

    This stunning 4 bedroom, 3 bathroom home with a beautifully updated kitchen is the perfect place to call home. With plenty of space to entertain and relax, you'll love the open layout and modern amenities that this home has to offer. Whether you're enjoying a meal in the spacious kitchen or unwinding in the cozy living room, you'll feel right at home in this charming and inviting space.

    Artan Kukaj SPIRAL NY Real Estate LLC

    63 Whitetail Run, Chester, NY 10918
  • /50

    $1,145,000

    $50K PRICE DROP
    • 9 Beds
    • 6.5 Baths
    • 4,965 Sq Ft

    19 High St, Chester, NY 10918

    Own One of America's Great Equestrian LandmarksSteeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of

    Beth Palma Keller Williams Realty

    19 High St, Chester, NY 10918
  • /50

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 4,281 Sq Ft

    22 Goshen Rd, Chester, NY 10918

    Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on

    Martha Randazzo Howard Hanna Rand Realty

    22 Goshen Rd, Chester, NY 10918

Home Price Trends

Median Sale Price
$500,000
Median Single Family Sale Price
$664,500
Median Townhouse Sale Price
$320,000
Median 2 Bedroom Sale Price
$310,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$273
Number of Homes for Sale
69
Last 12 months Home Sales
83
Months of Supply
10.00
Median List Price
$599,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-5%
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