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Chestertown Real Estate in the Adirondacks

Chestertown is a charming community located in the Southern Adirondacks, an easy drive to Lake George NY and Gore Mountain in North Creek. Founded in 1799, the historic district here was added to the National Register of Historic Places in 1977. There are many new builds in addition to colonial and victorian homes.

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Chestertown, NY 12817

4 Bed , 2 full Bath ... Experience the very best of Adirondack lakefront living in this private, completely renovated 4-bedroom, 2.5-bath Loon Lake retreat, complete with a RARE... Listing Details

$1,799,000

Active
4 Bed
2 full Bath
1,782 sq. ft.
1.31 Acres

Listing by:
Chestertown, NY 12817

0 Bed , Bath ... Exceptional development opportunity at Exit 25 of the Adirondack Northway (I-87). Approximately 30 acres with frontage on NY Route 8, positioned immediately... Listing Details

$1,600,000

Active
0 Bed
30.00 Acres

Listing by:
Chestertown, NY 12817

5 Bed , 3 full Bath ... Extraordinary Adirondack retreat situated on 10 private acres, ideally located between Forest Lake and Kelm Pond, offering the perfect blend of privacy,... Listing Details

$799,900

Active
5 Bed
3 full Bath
2,750 sq. ft.
10.00 Acres

Listing by:
Chestertown, NY 12817

3 Bed , 2 full Bath ... Where Adirondack privacy meets the Loon Lake lifestyle, this custom-built year-round home offers deeded docking and sandy beach access, all while being... Listing Details

$789,000

Active
3 Bed
2 full Bath
1,476 sq. ft.
5.53 Acres

Listing by:
Chestertown, NY 12817

5 Bed , 3 full Bath ... **NEW PRICE!** As autumn gives way to winter, there's no better time to discover your Adirondack basecamp! Welcome to 190 Kingsley Lane... Listing Details

$779,000

Active
5 Bed
3 full Bath
2,482 sq. ft.
2.03 Acres

Listing by:
Chestertown, NY 12817

3 Bed , 2 full Bath ... Chestertown Reduced Price, NEW Driveway, Loon Lake Area, Truly a Spectacular Constructed Nearly new and quality Built in 2023, custom-designed, gorgeous and... Listing Details

$740,000

Active
3 Bed
2 full Bath
2,700 sq. ft.
7.89 Acres

Listing by:
Chestertown, NY 12817

4 Bed , 3 full Bath ... Live where adventure begins. Set on 5+ wooded acres of total privacy, this Adirondack escape puts you minutes from lakes, hiking, skiing,... Listing Details

$699,900

Pending
4 Bed
3 full Bath
3,977 sq. ft.
5.13 Acres

Listing by:
Chestertown, NY 12817

0 Bed , Bath ... 2,200 feet of frontage along the Upper Hudson River, a wild, whitewater backcountry river, and immediate access to nearly 1,600 acres of... Listing Details

$699,900

Active
0 Bed
337.00 Acres

Listing by:
Chestertown, NY 12817

3 Bed , 1 full Bath ... Rich in Adirondack history and surrounded by nature, Calamity Cove is a one-of-a-kind year-round retreat offering over 3 acres across two separately... Listing Details

$650,000

Active
3 Bed
1 full Bath
1,220 sq. ft.
3.04 Acres

Listing by:
Chestertown, NY 12817

3 Bed , 2 full Bath ... Enjoy Adirondack living in this beautiful Loon Lake home. This residence offers 3 bedrooms, 2 bathrooms with numerous upgrades and custom finishes... Listing Details

$639,000

Active
3 Bed
2 full Bath
1,806 sq. ft.
1.02 Acres

Listing by:
Chestertown, NY 12860

5 Bed , 3 full Bath ... Classic Adirondack character meets over $200,000 in recent renovations at this inviting four-season log home. The warmth of natural wood and a... Listing Details

$619,000

Active
5 Bed
3 full Bath
2,069 sq. ft.
5.71 Acres

Listing by:
Chestertown, NY 12817

4 Bed , 2 full Bath ... This charming 4 bedroom, 2 bath home is in a private setting, yet conveniently located to Loon Lake town, lakes, rivers and... Listing Details

$585,000

Active
4 Bed
2 full Bath
1,948 sq. ft.
2.54 Acres

Listing by:
Chestertown, NY 12817

4 Bed , 2 full Bath ... Experience the charm of Loon Lake Adirondack lake living with this inviting year-round home set on 2.5 acres and offering deeded beach... Listing Details

$575,000

Active
4 Bed
2 full Bath
2,144 sq. ft.
2.50 Acres

Listing by:
Chestertown, NY 12817

4 Bed , 3 full Bath ... Contemporary 4-bedroom, 3-bath home set on over 17 acres, featuring 572 feet of direct frontage on the Schroon River. This property offers... Listing Details

$539,000

Active
4 Bed
3 full Bath
2,584 sq. ft.
17.90 Acres

Listing by:
Chestertown, NY 12817

2 Bed , 1 full Bath ... 71 FT OF LAKEFRONT WITH SANDY SWIMMING, BEACH, DOCK & RARE LAKESIDE CABANA ON LOON LAKE! At the end of appropriately named... Listing Details

$525,000

Active
2 Bed
1 full Bath
752 sq. ft.
0.35 Acres

Listing by:
Chestertown, NY 12817

5 Bed , 2 full Bath ... This is a historic gem in the Friends Lake area. Not only does the home have deeded rights to Friends Lake, It... Listing Details

$499,900

Active
5 Bed
2 full Bath
1,646 sq. ft.
1.13 Acres

Listing by:
Chestertown, NY 12817

2 Bed , 2 full Bath ... BELOW APPRAISED VALUE! ADIRONDACK LIVE-WORK RETREAT! Completely remodeled mixed-use property ideal as a primary residence, vacation getaway, investment, or live-work space. Nestled... Listing Details

$486,000

Active
2 Bed
2 full Bath
3,444 sq. ft.
0.52 Acres

Listing by:
Chestertown, NY 12817

0 Bed , Bath ... BELOW APPRAISED VALUE! EXCEPTIONAL ADIRONDACK OWNER-OPERATOR OPPORTUNITY! Live upstairs, run your business downstairs, and enjoy the convenience of having it all under... Listing Details

$486,000

Active
0 Bed
3,444 sq. ft.
0.52 Acres

Listing by:
Chestertown, NY 12885

4 Bed , 2 full Bath ... This extensively updated, 1,990 sq. ft., 4-bedroom home features a new roof, new furnace, new well pump, newly repainted exterior, updated flooring... Listing Details

$439,900

Active
4 Bed
2 full Bath
1,990 sq. ft.
1.60 Acres

Listing by:
Chestertown, NY 12817

5 Bed , 1 full Bath ... An exceptional opportunity awaits in the heart of Chestertown! Set on approximately 1.12 acres, this distinctive property has a rich history as... Listing Details

$410,000

Active
5 Bed
1 full Bath
4,800 sq. ft.
1.12 Acres

Listing by:
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