Chestertown, NY Homes for Sale

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

Welcome to your serene Adirondack retreat on the shores of Loon Lake, where the call of the loons will greet you. This charming 3-bedroom, 1-bath cottage boasts 37 feet of private lakefront with a dock—perfect for swimming, boating, or simply soaking in the serene views with family and friends. Inside, you'll be embraced by classic Adirondack ambiance, featuring a stunning stone fireplace, a cozy

Barbara Kearney Hunt ERA

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

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

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

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

Welcome to a serene and private Adirondack retreat where thoughtful design meets natural beauty. This unique offering includes two separate parcels: a charming 3-bedroom, 1.5-bath ranch on a 1-acre lot, and a spacious 5 plus acre vacant parcel located directly across the road—ideal for expansion, recreation or investment.Step inside to discover a stylishly updated Adirondack home with

Barbara Kearney Hunt ERA

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

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

James Nester Cork Nester's True North Prop

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

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

This is a Multi-family 2-unit rental in the heart of Chestertown! Walking distance to everything in town- shops, restaurants, etc. Main level is a commercial space w/ half bath (currently not rented) 2nd level- 1 bed/1bath apartment. New metal roof- must have 24-48 hr notice for ALL showings!

Julia Pucciarelli Gallo Realty ADK Inc

Here's your chance to affordably own a peaceful Adirondack retreat! Nestled off a dead-end road on a quiet 0.40-acre lot, this property presents an ideal opportunity for a rustic getaway or future vacation rental. The Amish-built cabin already includes rough-plumbing, gazebo, well, septic, and electric—waiting for your finishing touches. Perfect for glamping, an RV spot, or a cozy home base.

Alex Cooley Compass Greater NY, LLC