Chestertown, NY homes for sale & real estate

Chestertown, NY Homes for Sale

Outstanding opportunity to own this spacious home on main street in the heart of Chestertown! This property is an absolute cash cow making an impressive amount year after year as a short term rental. (Inquire for rental projection. ) With 6 bedrooms & 3 full baths this home sleeps up to 20 people! Loon Lake is a quick 2 minute drive, Lake George & Gore Mountain is a 20 minute drive. Features include gleaming HW floors throughout, updated kitchen, new windows, enclosed porch perfect for entertaining & great sized heated in ground pool. Walking distance to the supermarket, restaurants, biking & snowshoe trails! This home has so much charm, character & history. Le

Chestertown, NY Homes for Sale

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 or entertaining. A short walk along a wooded path leads to Tripp Lake, offering swimming, paddling, & fishing or walk out your door and play pickleball. On-site storage for recreational gear & seasonal items. Ideal for weekend getaways or full-time living, this peaceful property

Chestertown, NY Homes for Sale

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 Association, common roads are maintained and plowed in winter and there is a shared sandy beach area with picnic tables. One deeded dock space is sold with this home. Don't miss this perfect Get-Away Home or Permanent Residence. * * Note: Showings start 7/7/25 by appointment only - all buyers must be prequali

Chestertown, NY Homes for Sale

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, in-unit laundry, and more. Enjoy beach access and HOA amenities on a non-motorized lake. Optional golf and tennis memberships available. Centrally located—just minutes to Lake George, 20 minutes to Gore Mountain, and 40 minutes to Saratoga Springs for shopping, dining, and track season!Agent