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Chester, NY Open Houses

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  • /48

    $1,100,000

    Open Sun 2PM - 4PM
    • 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

    (845) 328-2396

    53 Gibson Hill Rd, Chester, NY 10918
  • /49

    $1,399,777

    New Construction Open Sat 1PM - 3PM $50K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 4,508 Sq Ft

    145 Kings Highway Bypass, Chester, NY 10918

    Set gracefully on 3.8 private acres within the highly coveted Warwick School District, this exceptional custom home offers a rare blend of architectural elegance and refined living. Surrounded by a collection of equally distinguished residences, the property provides an expansive, park-like sanctuary while remaining nestled in the heart of one of the region’s most sought-after communities.

    Courtney Tablante Keller Williams Realty

    145 Kings Highway Bypass, Chester, NY 10918
  • /47

    $825,000

    Open Sun 11AM - 1PM
    • 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
  • /46

    $799,999

    Open Sun 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    58 Nancy Ln, Chester, NY 10918

    Brand new to the market! Perched atop the desirable Fieldcrest subdivision with sweeping panoramic views and unforgettable sunsets, this spectacular Colonial offers exceptional space, comfort, and versatility both inside and out. Set on 1.3 picturesque acres, this beautifully maintained home is designed for everyday living and effortless entertaining.A charming oversized front porch overlooks

    Gina Dudgeon Howard Hanna Rand Realty

    58 Nancy Ln, Chester, NY 10918
  • /21

    $590,000

    Open Sat 2:30PM - 4:30PM
    • 3 Beds
    • 2.5 Baths
    • 2,083 Sq Ft

    94 Booth Rd, Chester, NY 10918

    Finding a true three-bedroom, three-bathroom home in Chester for under $600k is a rare win—but finding one with over 2,000 square feet of thoughtful living space is the real jackpot. Welcome to 94 Booth Road. From the moment you pull up, this property feels like home. It’s the kind of place where the layout actually makes sense for real life. With three full baths, the morning rush becomes a

    Craig Watters Compass Greater NY, LLC

    94 Booth Rd, Chester, NY 10918
  • /28

    $579,999

    Open Sun 11AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,698 Sq Ft

    24 Walnut St, Chester, NY 10918

    Welcome to 24 Walnut Street, Flexibility, Space & Endless Possibility in the Heart of Chester, NYTucked on a generous half-acre lot in the charming Village of Chester, this versatile 4-bedroom, 2.5-bath home offers a rare mother-daughter layout that delivers the best of both worlds, income potential, or simply more space to grow. Set on a quiet, tree-lined street just minutes from the Orange

    Tara Roufanis Keller Williams Village Sq Rlt

    24 Walnut St, Chester, NY 10918
  • /33

    $549,000

    Open Sun 1PM - 3PM Coming Soon
    • 3 Beds
    • 2.5 Baths
    • 1,730 Sq Ft

    107 Pine Hill Rd, Chester, NY 10918

    Something Special! See It and Fall in Love! A pavered walkway welcomes you to this curb appealing 3 BR, 2 1/2 bath Stucco Cape that is privately set on 1.1 acres! Open and sun filled with lots of windows! So many updates! Large primary BR and luxurious bath are on the 1 st floor! Open LR and DR have sliders to private deck to enjoy pastoral views and views of Sugar Loaf Mountain! 2 large BRs with

    Linda Clark Hudson Valley Griffith

    107 Pine Hill Rd, Chester, NY 10918
  • /46

    $699,000

    Open Sun 1PM - 3PM $151K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,120 Sq Ft

    558 Pine Hill Rd, Chester, NY 10918

    Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

    Charnie Guttmann eRealty Advisors, Inc

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

    $299,000

    Open Sun 1AM - 3PM $51K PRICE DROP
    • Land
    • 5.7 Acres
    • $52,456 per Acre

    552 Pine Hill Rd, Chester, NY 10918

    Beautiful 5.7-acre residential parcel located in the Town of chester, offering an exceptional opportunity to build your custom dream home in a peaceful, private setting. With ample space for a spacious residence and outdoor living areas (subject to town approvals), this property combines natural surroundings with convenient access to nearby amenities, schools, and major roadways. Adjacent to 558

    Charnie Guttmann eRealty Advisors, Inc

    552 Pine Hill Rd, Chester, NY 10918

Home Trends in Chester, NY

Housing Trends

Median Sale Price
$500,750
Median Single Family Sale Price
$660,000
Median Townhouse Sale Price
$332,450
Median 2 Bedroom Sale Price
$305,000
Average Price Per Sq Ft
$275
Number of Homes for Sale
50
Last 12 months Home Sales
88
Months of Supply
6.80
Median List Price
$579,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-4%
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