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Chestertown, NY Houses for Sale

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  • /71

    $359,000

    • 3 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    22 Shady Ln, Chestertown, NY 12817

    Enjoy swimming, paddling, and fishing at the perfect Adirondack getaway with complete privacy, a cabin, a large deck, a shed, and 250’ of frontage on the Schroon River. The driveway meanders through the woods and arrives at a nice clearing, and the cabin is overlooking the river. The backdrop of mature white pine and hemlock trees provides beauty and privacy for the 1,080 sq. ft 3-bedroom,

    Michael Fudzinski

    22 Shady Ln, Chestertown, NY 12817
  • /45

    $499,900

    • 4 Beds
    • 2 Baths
    • 2,136 Sq Ft

    278 Carl Turner Rd, Chestertown, NY 12817

    Multiple Offers Received - Highest & Best Due Monday at 6 PM. Escape the city and reconnect with nature in this spacious 2,100+ sq ft riverfront home that still feels like a cozy camp. Picture the kids jumping off the dock, fishing from the shore, or boating through the canal with direct access to Schroon Lake. After a day on the water, stop by the Crossroads Store just 1.5 miles away for

    Shannon McCarthy eXp Realty

    278 Carl Turner Rd, Chestertown, NY 12817
  • /26

    $489,000

    • 3 Beds
    • 1 Bath
    • 920 Sq Ft

    18 Woodcliff Acres, Chestertown, NY 12817

    Life is better at the Lake --- Friends Lake --- in Chestertown, NY. This year-round home has a new well and digital thermostats for remote control heat before arrival. A List of updates is available in documents. Features include an enclosed porch, three bedrooms, den/office, stone fireplace. a wrap-around deck, and outdoor firepit. As a member of the Woodcliff Acres Property Owners

    Carol Asiello KW Platform

    18 Woodcliff Acres, Chestertown, NY 12817
  • /38

    $339,000

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft

    68 Elks Glade Rd, Chestertown, NY 12817

    Charming Friends Lake Retreat with Lake Rights & Docking! Tucked away on a quiet street, this 3-bedroom, 1-bath home offers 1,152 sq ft of cozy living space on .57 acres with deeded lake rights and docking access to beautiful Friends Lake. Enjoy evenings by the fireplace or unwind on the screened-in back porch surrounded by nature. Located just minutes from Main Street Chestertown and a short

    Julia Pucciarelli Gallo Realty ADK Inc

    68 Elks Glade Rd, Chestertown, NY 12817
  • /48

    $674,900

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

    209 Chester Shores Ridge, Chestertown, NY 12817

    **OPEN HOUSE: 7/19 SATURDAY 1-4PM!** 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.

    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
  • /55

    $349,900

    • 3 Beds
    • 1 Bath
    • 1,651 Sq Ft

    11 Mill St, Chestertown, NY 12817

    This is the ideal getaway to relax and take in the sights and smells of the Adirondacks.This Circa 1900 Farmhouse and Barn sit on over one acre and has direct waterfront on Faxon Pond. Unbelievable sunsets! Launch your canoe or kayak for a morning/ evening of taking in the sights, or cast a line for some laid back fishing. Large back yard. Fantastic Views. 15 minutes to Gore Mountain. Minutes to

    Valerie Erceg Davies-Davies & Assoc Real Est

    11 Mill St, Chestertown, NY 12817

Why Live in Chestertown

Chestertown, NY, a small Adirondack town, is known for its strong community spirit and outdoor recreational opportunities. Celebrating its 225th anniversary in July 2024, the town hosts events like car shows and festivals, showcasing its vibrant local culture. Residents enjoy four seasons of activities, from swimming and fishing in natural lakes to skiing and snowmobiling at nearby mountain resorts. Main Street is a hub of activity, featuring eateries such as the Bullhouse Kitchen and Bar, which offers Latin American-influenced comfort food, and the Main Street Ice Cream Parlor, serving breakfast and lunch. Cultural attractions include the Carol Theater and Birds of a Feather Studio and Gallery. Chestertown's historic district is walkable and bikeable, with easy access to Interstate 87, connecting to Albany and New York City. The town is safer than the national average, providing peace of mind for families. Homes range from historic houses to newer builds, with many purchased as vacation homes, though year-round residency is growing. Flooding can affect properties along routes 8 and 9, particularly near Chester Creek. Outdoor enthusiasts can explore nearby Gore Mountain and Pharaoh Lake Wilderness Area, offering skiing, hiking, and water activities. The Chester Challenge encourages hiking on local trails, promoting physical fitness. Chestertown's community organizations and events, such as Woof Stock and the Krazy Downhill Derby, further enrich the town's appeal, making it a unique place to live or visit.

Home Trends in Chestertown, NY

Housing Trends

Median Sale Price
$320,000
Median Single Family Sale Price
$349,900
Median Townhouse Sale Price
$296,500
Median 2 Bedroom Sale Price
$214,000
Median 1 Bedroom Sale Price
$137,500
Average Price Per Sq Ft
$251
Number of Homes for Sale
13
Last 12 months Home Sales
44
Months of Supply
3.50
Median List Price
$339,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
0%
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