MLS Listings for Sale in Chestertown, NY

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NEW 33 HRS AGO

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, NY
A truly rare opportunity to secure over two acres of prime land in the highly desirable and rapidly appreciating town of Chester. This charming property isn't just a home; it's a foundation for your future and a strategic long-term investment. Set on a sprawling 2.1+ acre lot, this property offers the space and privacy that is simply unmatched in today's market. The current single-level structure is neat, practical, and immediately livable, boasting a recently refreshed interior and a key functional update with a new roof installed in 2001. More importantly, the property is inherently designed for growth. With ample acreage, the home presents an easy and exciting opportunity for expansion,

$345,000

3 beds1 bath1,120 sq ft

65 Hudson St, Chester, NY 10918

Over two acres • New roof • 2.3 acre lot

Listing by Keller Williams Realty

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, NY
Welcome to one of the most breathtaking properties on Loon Lake — a true Adirondack retreat where serenity, beauty, and nature come together in perfect harmony. Nestled on a private peninsula surrounded on three sides by sparkling water, this stunning log-style home boasts an incredible * * 412 feet of direct lakefront * * and some of the * * best panoramic views on all of Loon Lake * * . As you walk down the short wooded pathway, anticipation builds until you arrive at your dream destination — a warm, inviting lakefront escape featuring a * * double-sided stone fireplace * * that anchors the heart of the home. Enjoy the glow of the fire from both the cozy living area

$1,250,000

3 beds2 baths2,160 sq ft

161 E Shore Dr, Chestertown, NY 12817

Loft attic • 3-car garage • Private dock

Listing by KW Platform

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, NY
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. Must see this property to appreciate.

$225,000

2 beds1 bath1,160 sq ft

60 Dixon Rd, Chestertown, NY 12817

Drilled-well • Added porches • 2-car garage

Listing by Gallo Realty ADK Inc

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, NY
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 timeless characters - featuring newer appliances and a cozy wood stove. The inviting three-season room (fitted with diffuser screens - bright yet comfortably shaded) and outdoor decks are perfect for entertaining or quiet evenings under the stars. Perennial gardens, fire pit and a small pondle (smaller

$374,000

3 beds1.5 baths1,344 sq ft

484 Rock Ave, Chestertown, NY 12817

Two separate parcels • Three-season room • Perennial gardens

Listing by Hunt ERA

ABOUT THIS HOME
MLS Listings for Sale in Chestertown, NY
Adorable 2-Bedroom Cottage on the Schroon River! Enjoy life on the water in this charming 2-bed, 1-bath getaway located above the dam, offering boat access directly into Schroon Lake! Cozy living room area with views of the river. Plenty of kitchen space. A dining room w/ fireplace to enjoy with friends & family! Short drive to downtown Chestertown & Schroon Lake! Close proximity to surrounding lakes, hiking trails & restaurants. Your Adirondack adventure awaits!

$299,000

2 beds1 bath877 sq ft

73 Carl Turner Rd, Chestertown, NY 12817

Surrounding lakes • Boat access • Dining room

Listing by Gallo Realty ADK Inc

Property at 367 Potter Brook Rd, Chestertown, NY 12817, 3 beds, 1.5 baths

$589,900

3 beds1.5 baths2,752 sq ft

367 Potter Brook Rd, Chestertown, NY 12817

Listing by Howard Hanna

Property at 46 Fiddlehead Bay Rd, Chestertown, NY 12817, 8 beds, 9.5 baths

$5,300,000

8 beds9.5 baths8,019 sq ft

46 Fiddlehead Bay Rd, Chestertown, NY 12817

Listing by Davies-Davies & Assoc Real Est

Property at 18 Woodcliff Acres, Chestertown, NY 12817, 3 beds, 1 bath

$399,000

3 beds1 bath920 sq ft

18 Woodcliff Acres, Chestertown, NY 12817

Listing by KW Platform

Property at 4A High Pines Ter, Warrensburg, NY 12817, 2 beds, 2 baths

$225,000

2 beds2 baths1,404 sq ft

4A High Pines Ter, Warrensburg, NY 12817

Listing by Howard Hanna Capital Inc

Property at 24 Balsam Crest Path Unit B, Chestertown, NY 12817, 2 beds, 1.5 baths

$360,000

2 beds1.5 baths1,320 sq ft

24 Balsam Crest Path Unit B, Chestertown, NY 12817

Listing by CapMark Realty LLC

Property at 68 Elks Glade Rd, Chestertown, NY 12817, 3 beds, 1 bath

$319,000

3 beds1 bath1,152 sq ft

68 Elks Glade Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 11K Overlook Ln, Chestertown, NY 12817, 2 beds, 1.5 baths

$189,000

2 beds1.5 baths928 sq ft

11K Overlook Ln, Chestertown, NY 12817

Listing by John R. Palermo

Property at L7 Macglashan Ln, Chestertown, NY 12817

$69,000

— beds— baths— sq ft

L7 Macglashan Ln, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at L31 Clarkson Rd, Chester, NY 12817

$144,900

— beds— baths— sq ft

L31 Clarkson Rd, Chester, NY 12817

Listing by Four Seasons Sotheby's International Realty

Property at 14 Granite Ridge Rd, Chestertown, NY 12817

$49,000

— beds— baths— sq ft

14 Granite Ridge Rd, Chestertown, NY 12817

Listing by Big Hat Realty

Property at L 30.1 Pucker St, Warrensburg, NY 12885

$599,900

— beds— baths— sq ft

L 30.1 Pucker St, Warrensburg, NY 12885

Listing by eXp Realty

Property at L34 Mountain Ln, Warrensburg, NY 12817

$229,000

— beds— baths— sq ft

L34 Mountain Ln, Warrensburg, NY 12817

Listing by John R. Palermo

Property at 38 Granite Ridge Rd, Chestertown, NY 12817

$83,500

— beds— baths— sq ft

38 Granite Ridge Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 61 Snowshoe Rdg, Warrensburg, NY 12885

$74,000

— beds— baths— sq ft

61 Snowshoe Rdg, Warrensburg, NY 12885

Listing by Luxe Key Realty

Property at L9 Atateka Rd, Chestertown, NY 12817

$299,900

— beds— baths— sq ft

L9 Atateka Rd, Chestertown, NY 12817

Listing by Timberland Realty

Property at L4-5 Marina Rd, Chestertown, NY 12817

$74,900

— beds— baths— sq ft

L4-5 Marina Rd, Chestertown, NY 12817

Listing by John R. Palermo

Property at L2 Friends Lake Rd, Chester, NY 12817

$169,500

— beds— baths— sq ft

L2 Friends Lake Rd, Chester, NY 12817

Listing by Gallo Realty ADK Inc

Property at 115 Atateka Dr, Chestertown, NY 12817

$85,000

— beds— baths— sq ft

115 Atateka Dr, Chestertown, NY 12817

Listing by Bryce Real Estate Inc

Property at 3-4 Adirondack Heights Rd, Chestertown, NY 12817

$89,500

— beds— baths— sq ft

3-4 Adirondack Heights Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at Landon Hill Rd, Chestertown, NY

$76,900

— beds— baths— sq ft

Landon Hill Rd, Chestertown, NY

Listing by William Raveis-New York LLC

Property at L37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chester, NY 12817

$57,500

— beds— baths— sq ft

L37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chester, NY 12817

Listing by John R. Palermo

Property at 00 Adirondack Heights Rd Lot 8, Chestertown, NY 12817

$46,000

— beds— baths— sq ft

00 Adirondack Heights Rd Lot 8, Chestertown, NY 12817

Listing by KW Platform

Property at L 13.2 Friends Lake Rd, Chester, NY 12817

$699,900

— beds— baths— sq ft

L 13.2 Friends Lake Rd, Chester, NY 12817

Listing by Timberland Realty

Property at 64 Carriage Knolls Rd, Chestertown, NY 12817

$69,000

— beds— baths— sq ft

64 Carriage Knolls Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 102 Carriage Knoll Rd, Chestertown, NY 12817

$74,900

— beds— baths— sq ft

102 Carriage Knoll Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 62 Carriage Rd, Chester, NY 12817

$62,000

— beds— baths— sq ft

62 Carriage Rd, Chester, NY 12817

Listing by Gallo Realty ADK Inc

Property at 112 Carriage Knoll Rd, Chestertown, NY 12817

$76,900

— beds— baths— sq ft

112 Carriage Knoll Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 77 Carriage Knoll Rd, Chestertown, NY 12817

$74,900

— beds— baths— sq ft

77 Carriage Knoll Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 86 Carriage Knoll Rd, Chestertown, NY 12817

$68,900

— beds— baths— sq ft

86 Carriage Knoll Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 72 Carriage Knoll Rd, Chestertown, NY 12817

$68,900

— beds— baths— sq ft

72 Carriage Knoll Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 13 Carriage Rd, Chester, NY 12817

$37,500

— beds— baths— sq ft

13 Carriage Rd, Chester, NY 12817

Listing by Gallo Realty ADK Inc

Property at 20 Carriage Rd, Chester, NY 12817

$49,500

— beds— baths— sq ft

20 Carriage Rd, Chester, NY 12817

Listing by Gallo Realty ADK Inc

Property at 37 Carriage Rd, Chester, NY 12817

$39,000

— beds— baths— sq ft

37 Carriage Rd, Chester, NY 12817

Listing by Gallo Realty ADK Inc

Property at 22 Carriage Rd, Chester, NY 12817

$39,500

— beds— baths— sq ft

22 Carriage Rd, Chester, NY 12817

Listing by Gallo Realty ADK Inc

Property at 60 Carriage Rd, Chester, NY 12817

$37,500

— beds— baths— sq ft

60 Carriage Rd, Chester, NY 12817

Listing by Gallo Realty ADK Inc

Property at 34 Carriage Rd, Chester, NY 12817

$39,500

— beds— baths— sq ft

34 Carriage Rd, Chester, NY 12817

Listing by Gallo Realty ADK Inc

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Based on information submitted to the MLS GRID as of Wed Nov 12 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

MLS Listings for Sale in Chestertown

There are currently 46 mls listings for sale in Chestertown at a median listing price of $199K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chestertown stay on the market for 105 days. This map is refreshed with the newest listings in Chestertown every 15 minutes.

In the past month, 4 homes have been sold in Chestertown. In addition to houses in Chestertown, there was also 1 condo, 1 townhouse, and 2 multi-family units for sale in Chestertown last month. Find your dream home in Chestertown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chestertown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chestertown. Our Chestertown real estate stats and trends will give you more information about home buying and selling trends in Chestertown. If you're looking to sell your home in the Chestertown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chestertown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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