Chestertown, NY Homes for Sale

Tucked away on 2.67 private Adirondack acres, this fully renovated 6-bedroom, 5.5-bath retreat offers the perfect blend of adventure, flexibility, and modern mountain living. Whether you're searching for a year-round residence, luxury vacation home, or high-potential short-term rental investment, this property was designed for the way people want to live, gather, and escape today. Located near

John LaRocca Davies-Davies & Assoc Real Est

Charming and fully renovated, this private retreat sits on 3.43 serene acres and features a 3-bedroom, 3-bath main home with a finished basement, alongside a 2-bedroom, 1-bath guest house complete with a 3-car garage and a screened-in porch. The combined living space is approximately 4,000 square feet. Enjoy the tranquility of a secluded setting that's still close to amenities, making it ideal as

Sara Hillis Schermerhorn Realty Group LLC

Rustic seasonal lakefront camp with 439 feet of frontage including your own cove on private Friends Lake on the East Shore. Nestled among the pines on a rare 3.42 secluded acres with a dock, small boat house (for storage only), one car garage and lakeside patio. Owned by only one family for three generations. Step back to a simpler time at this charming retreat perched at the water's edge. Enjoy

Jill Brady Hunt ERA

Opportunity to own an Adirondack Town Home in the private Green Mansions development. A resort style HOA that includes tennis courts, nature walking trails, golf course, private swimming and paddle board lake. Near Gore Mountain Ski Complex, Dynamite Hill Sledding, Lake George and all the Adirondack Mountains have to offer. Ideal investment property with past solid rental history and completely

John Gollhofer CapMark Realty LLC

Tucked away on 6.5+ wooded acres at the end of a quiet dead-end road, this brand new 3-bedroom, 2-bath home offers the perfect blend of privacy and simplicity. Just completed and never lived in, with a new well, septic, and freshly seeded lawn--everything is done for you. Move right in and start enjoying easy, low-maintenance living in Chestertown. A peaceful setting you'll fall in love with the

Angie Mead Gallo Realty ADK Inc

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

Set on a .45-acre lot in the heart of Chestertown, this spacious Colonial presents a standout opportunity in the Lake George region, equally suited as a full-time home, seasonal escape, or high income-producing property. Offering 2,916 square feet, the home features 6 bedrooms and 3 full bathrooms, with a layout designed to comfortably host large groups with ease. Its size and setup make it

Robert Saumell Jr. KW Platform

Nestled along 100' of direct frontage on beautiful Loon Lake, this well-maintained year-round home offers breathtaking 180-degree lake and mountain views with the perfect setup for summer fun. Enjoy a sandy-bottom shoreline, two levels of usable waterfront with natural stone retaining walls, pressure-treated stairs, and a 40' x 6' permanent dock ideal for boating, swimming, fishing, kayaking, and

Angie Mead Gallo Realty ADK Inc

Set on 2.5+ private acres off a quiet country road at the southern gateway to the Adirondack Park, this home offers easy access to year-round outdoor activities. Gore Mountain Ski Resort and Lake George are both just 30 minutes away, while shopping, fine dining, and health care are only minutes away in historic Warrensburg. This spacious three-bedroom, two-bath home features a cozy bar area and

Jennifer Sherry Sherwood Group, LLC

Exquisite Schroon River Family Compound! Nestled on 3.9 private acres with direct frontage on the Schroon River, this exceptional property offers the perfect blend of luxury, comfort, and Adirondack charm. The heart of the home is a stunning custom kitchen filled with natural light, featuring quality finishes and a convenient prep sink. The elegant dining area showcases a statement chandelier and

Julia Pucciarelli Gallo Realty ADK Inc

Chestertown, Truly a Spectacular Constructed Nearly new and quality Built in 2023, custom-designed, gorgeous and meticulous home located on town maintained private dead-end road on 7.89 acres. Contemporary open-floor plan home with spacious rooms with quality construction from top to bottom. 3-4 bedrooms (including a large loft area). Kitchen quartz countertop. Huge master bedroom with walk-in

Carol Monroe Najer Realty

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

Welcome to this fully furnished 2-bedroom, 1.5-bath condo in the sought-after Green Mansions community. It features an open-concept living area with a gorgeous stone wood burning fireplace. Step outside to a private deck, perfect for relaxing or entertaining. A short walk along a wooded path leads to Tripp Lake, offering swimming, paddling, and fishing -or walk right out your door and play tennis

Barbara Kearney Hunt ERA

Beautiful setting with 3.45 cleared and mostly flat acres next to Crossroads store in Chestertown. Manufactured home (year-round) with added porches, 2-car garage, and several outbuildings. Drilled-well, septic system and 200-amp electric panel. 2-designated bedrooms with a 3rd flex room that could be a bedroom or overflow sleeping. less than a minute drive from exit 25 off I87 for easy access.

Walter Swartz Gallo Realty ADK Inc

Escape to your own Adirondack hideaway. Nestled on a private .46-acre lot, this charming 2-bed, 2-bath home offers the perfect balance of rustic character and modern comfort. Just steps from Loon Lake, the property features filtered lake views and deeded rights to the sandy beach, giving you effortless access to swimming, paddling, and the full lake lifestyle. Step inside to a warm,

Barbara Kearney Hunt ERA

Extraordinary Adirondack retreat situated on 10 private acres, ideally located between Forest Lake and Kelm Pond, offering the perfect blend of privacy, comfort, and versatility. Built in 2016, this unique property features a beautifully designed 3-bedroom, 2.5-bath main residence plus a separate 2-bedroom, 1-bath guest suite along with an oversized garage, making it ideal for extended family,

Angela Cugini-Girard eXp Realty

This is a Multi-family 3-unit rental in the heart of Chestertown! Walking distance to everything in town- shops, restaurants, etc. Main level is a commercial space (currently the Chiropractor office) 2nd level- 1 bed/1bath apartment. Basement level- studio apartment 1bed/1bath. New septic installed 5 years ago- building painted in 2021! All units currently rented- must have 24-48 hr notice for

Julia Pucciarelli Gallo Realty ADK Inc

Discover the perfect Adirondack retreat at 50 Kingsley Lane, where space, comfort, and four-season recreation come together. This beautifully maintained home offers 2,552 sq ft of finished living space plus an additional 1,032 sq ft unfinished walk-out basement, providing endless possibilities for a game room, home theater, gym, additional bedrooms, or expanded entertaining space.The

Brooke Clark Four Seasons Sotheby's International Realty