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Chestertown, NY Condos for Sale

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  • /51

    $325,000

    • 4 Beds
    • 4 Baths
    • 840 Sq Ft

    5 Overlook Ln N Unit B & D, Chestertown, NY 12817

    Rare, year-round double Condominium at 5 Overlook Lane, B/D in Warrensburg, NY—nestled in a peaceful, park-like setting with deeded lake rights to beautiful Tripp Lake. This spacious, renovated unit sleeps up to 16 and features two living areas with fireplaces, a custom kitchen, updated baths, and a large deck with seasonal lake views. Offering 4 en-suite bedrooms, sleeping loft, a wet bar,

    Agent Photo

    Joseph Cardinale

    Howard Hanna Capital, Inc. (Clifton Park)

    (518) 656-8047

    5 Overlook Ln N Unit B & D, Chestertown, NY 12817
  • /20

    $239,000

    • 2 Beds
    • 1.5 Baths
    • 1,020 Sq Ft

    11 Overlook Ln S Unit A, Chestertown, NY 12817

    Welcome to this fully furnished, Adirondack-style end unit condo w/ 2-bedroom, 1.5-baths which offers a seamless blend of Adk/retro charm & modern updates. Newly updated throughout, it features a stylish kitchen w/ new appliances, a cozy wood-burning fireplace, & an open-concept living area. Step outside to an expansive wraparound deck bordered by vibrant perennial gardens, perfect for relaxing

    Barbara Kearney Hunt ERA

    11 Overlook Ln S Unit A, Chestertown, NY 12817
  • /17

    $189,000

    • 2 Beds
    • 1.5 Baths
    • 928 Sq Ft

    11 Overlook Ln N, Chestertown, NY 12817

    This condominium has deck with partial lake view and is a member of the Green Mansions Tennis and Swim Club which includes use of Tennis, beach and boats for an annual membership fee of $389.76. Very nice furnishings included in sale. There is an outside storage unit on unit deck.

    John Palermo John R. Palermo

    11 Overlook Ln N, 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
$327,500
Median Single Family Sale Price
$349,950
Median Townhouse Sale Price
$296,500
Median 2 Bedroom Sale Price
$189,000
Median 1 Bedroom Sale Price
$135,000
Average Price Per Sq Ft
$253
Number of Homes for Sale
12
Last 12 months Home Sales
42
Months of Supply
3.40
Median List Price
$344,500
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
0%
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