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Chestertown, NY Homes for Sale with Garage

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  • /54

    $499,900

    • 5 Beds
    • 3 Baths
    • 2,915 Sq Ft

    177 Forest Lake Rd, Chestertown, NY 12817

    A rare chance to own your own Adirondack haven on 8.6 private acres with a serene pond! This 5-bedroom, 3-bath home offers a spacious, flexible layout with multiple gathering spaces, perfect for hosting or relaxing. Featuring a spacious kitchen with island and eating nook, a large formal dining room, and bright living room with wall of windows to soak up the sunlight and scenic views of the

    Tess Baker Hunt ERA

    177 Forest Lake Rd, Chestertown, NY 12817
  • /79

    $5,300,000

    • 8 Beds
    • 11 Baths
    • 8,019 Sq Ft

    46 Fiddlehead Bay Rd, Chestertown, NY 12817

    This magnificent Adirondack lakefront compound on private Friends Lake is your opportunity to own over 12,000 sq ft of resort-style luxury designed for unforgettable memories. The main home offers 5 bed, 8 bath, while the in-law wing adds 4 bed, and 3 bath—plenty of room for everyone. Gather in the grand great room with soaring ceilings and a large stone fireplace, or retreat to one of several

    Ashley Nagy Davies-Davies & Assoc Real Est

    46 Fiddlehead Bay Rd, Chestertown, NY 12817
  • /48

    $659,900

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    209 Chester Shores Ridge, Chestertown, NY 12817

    Step within this Adirondack 4-Season home in the highly desired Chester Shores Community on Loon Lake, with available dock slip at the West Beach as of now. Enjoy the ambiance with a recently updated kitchen and great room with knotty pine cathedral ceilings. Spiral staircase leads to loft with private bath or down to the finished basement with garage access. Easily entertain with screened in

    Nicholas Khachadourian KW Platform

    209 Chester Shores Ridge, Chestertown, NY 12817
  • /53

    $799,900

    • 5 Beds
    • 2 Baths
    • 1,768 Sq Ft

    5387-5391 New York 8, Chestertown, NY 12817

    Experience rustic charm and modern comfort in this beautifully renovated farmhouse with 173 feet of direct lakefront and a private beach. Ideal as a year-round home, seasonal retreat, or income-generating rental, it features 5 spacious bedrooms and 2 full baths. The large backyard includes a versatile two-season outbuilding—great for parties or intimate weddings. Enjoy paddle boards, kayaks, a

    Philomena Prinzo Howard Hanna Capital Inc

    5387-5391 New York 8, Chestertown, NY 12817

Home Trends in Chestertown, NY

Housing Trends

Median Sale Price
$232,500
Median Single Family Sale Price
$255,000
Median Townhouse Sale Price
$335,000
Median 2 Bedroom Sale Price
$184,500
Median 1 Bedroom Sale Price
$135,000
Average Price Per Sq Ft
$200
Number of Homes for Sale
6
Last 12 months Home Sales
22
Months of Supply
3.30
Median List Price
$267,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-8%
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