Recently Sold Homes in Chestertown, NY

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SOLD DEC 18, 2025

ABOUT THIS HOME
Recently Sold Home 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

$370,000 Last sold price

3 beds1.5 baths1,344 sq ft

484 Rock Ave, Chestertown, NY 12817

Listing by Hunt ERA

SOLD NOV 3, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Chestertown, NY:
No maintenance, carefree living! Beautiful 3 story townhouse in the Green Mansions community with deeded rights to Tripp Lake. Swim, kayak, golf, tennis, ski and abundant trails for hiking. Quiet & peaceful haven close to Lake George, Lake Placid & Gore Mountain. One owner home meticulously maintained & loved through the years. Modern kitchen with granite countertops. Fireplace is currently electric but can easily be converted back to wood burning. Beautiful woodwork throughout. Full walkout basement currently used as a family/guest room. Screened porches off the living room and primary bedroom plus patio down below. Whether you're looking for a vacation home or year roun

$340,000 Last sold price

2 beds1.5 baths1,988 sq ft

28 Balsam Crest Ln Unit C, Chestertown, NY 12817

Listing by Howard Hanna Capital Inc

SOLD DEC 4, 2025

ABOUT THIS HOME
Recently Sold Home in Chestertown, NY:
Welcome to your Adirondack retreat! This charming 2-bedroom, 2-bath log home sits on 5 acres of privacy just minutes from Chestertown. Warm wood finishes, hardwood floors throughout, and a cozy wood stove create that true cabin feel! With central air to ensure year-round comfort. Finished basement w/ laundry room. Relax with friends and family on the wrap-around porch surrounded by nature. Shed for additional outdoor storage. Enjoy easy access to local lakes, restaurants, and Gore Mountain skiing. Whether you're searching for a full-time residence or a weekend getaway, this home offers the perfect balance of rustic charm and modern convenience in a peaceful setting.

$362,500 Last sold price

2 beds2 baths1,118 sq ft

30 Kingsley Lane Ext, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

SOLD OCT 2, 2025

ABOUT THIS HOME
Recently Sold Home in Chestertown, NY:
One of a kind setting, this well built beloved Ranch home with 9+ acres, 3 bedrooms, large LR with stone fireplace, 1 bathroom, full basement with laundry area and lots of storage shelves. Exterior with fenced in pet area, huge detached deck, front porch, perennial shrubs surround, paved driveway, 2 car garage with attached workshop. Privacy yet close to the town of Chestertown. With some updating interior, possibilities are endless.

$275,000 Last sold price

2 beds1 bath1,080 sq ft

347 Landon Hill Rd, Chestertown, NY 12817

Listing by Najer Realty

SOLD DEC 10, 2025

ABOUT THIS HOME
Recently Sold Home in Chestertown, NY:
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 sleeping loft, and spacious gathering areas designed for making lasting memories. The newly renovated country kitchen and updated bathroom offer a seamless blend of rustic charm and modern convenience, while the outdoor shower adds a refreshing touch of lakeside luxury. With insulated walls (

$570,000 Last sold price

3 beds1 bath1,156 sq ft

22 Memory Ln, Chestertown, NY 12817

Listing by Hunt ERA

Property at 3K High Pines Ter, Chestertown, NY 12817, 1 bed, 1.5 baths

$137,000 Last sold price

1 bed1.5 baths848 sq ft

3K High Pines Ter, Chestertown, NY 12817

Listing by Hunt ERA

Property at 177 Forest Lake Rd, Chestertown, NY 12817, 5 beds, 3 baths

$495,000 Last sold price

5 beds3 baths2,025 sq ft

177 Forest Lake Rd, Chestertown, NY 12817

Listing by Hunt ERA

Property at 180 E Kelm Pond Rd, Chestertown, NY 12817, 2 beds, 2 baths

$565,000 Last sold price

2 beds2 baths864 sq ft

180 E Kelm Pond Rd, Chestertown, NY 12817

Listing by Davies-Davies & Assoc Real Est

Property at 251 Stock Farm Rd, Chestertown, NY 12817, 2 beds, 1 bath

$285,000 Last sold price

2 beds1 bath1,320 sq ft

251 Stock Farm Rd, Chestertown, NY 12817

Listing by KW Platform

Property at 90 Dixon Rd, Chestertown, NY 12817, 3 beds, 2 baths

$184,370 Last sold price

3 beds2 baths1,312 sq ft

90 Dixon Rd, Chestertown, NY 12817

Listing by Hunt ERA

Property at 123 Stock Farm Rd, Chestertown, NY 12817, 3 beds, 2.5 baths

$605,000 Last sold price

3 beds2.5 baths2,528 sq ft

123 Stock Farm Rd, Chestertown, NY 12817

Listing by Davies-Davies & Assoc Real Est

Property at 972 Friends Lake Rd, Chestertown, NY 12817, 4 beds, 2 baths

$1,213,000 Last sold price

4 beds2 baths2,300 sq ft

972 Friends Lake Rd, Chestertown, NY 12817

Listing by Bonafide Realty Group

Property at 97 Riverside Dr, Chestertown, NY 12817, 2 beds, 2 baths

$145,000 Last sold price

2 beds2 baths2,016 sq ft

97 Riverside Dr, Chestertown, NY 12817

Listing by Howard Hanna

Property at 11 Mill St, Chestertown, NY 12817, 3 beds, 1 bath

$339,500 Last sold price

3 beds1 bath1,651 sq ft

11 Mill St, Chestertown, NY 12817

Listing by Davies-Davies & Assoc Real Est

Property at 20 Marina Rd, Chestertown, NY 12817, 3 beds, 2 baths

$549,900 Last sold price

3 beds2 baths968 sq ft

20 Marina Rd, Chestertown, NY 12817

Listing by Hunt ERA

Property at 11 N Overlook Ln Unit L, Chestertown, NY 12817, 3 beds, 2 baths

$192,000 Last sold price

3 beds2 baths840 sq ft

11 N Overlook Ln Unit L, Chestertown, NY 12817

Listing by Howard Hanna Capital Inc

Property at 23 Theriot Ave, Chestertown, NY 12817, 2 beds, 1 bath

$220,000 Last sold price

2 beds1 bath1,200 sq ft

23 Theriot Ave, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 25 Schroon River Frst, Chestertown, NY 12817, 3 beds, 1 bath

$215,000 Last sold price

3 beds1 bath920 sq ft

25 Schroon River Frst, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 4888 Route 8, Chestertown, NY 12817, 3 beds, 1 bath

$85,000 Last sold price

3 beds1 bath1,440 sq ft

4888 Route 8, Chestertown, NY 12817

Listing by DeMarsh Real Estate

Property at 11 S Overlook Ln Unit A, Chestertown, NY 12817, 2 beds, 1.5 baths

$225,000 Last sold price

2 beds1.5 baths1,020 sq ft

11 S Overlook Ln Unit A, Chestertown, NY 12817

Listing by Hunt ERA

$225,000

2 beds1.5 baths1,020 sq ft

11 Lane Dr Unit A, Warrensburg, NY 12885

$200,000

5 beds1 bath1,554 sq ft

83 McPhillips Dr, Chestertown, NY 12817

$340,000

3 beds2 baths1,080 sq ft

22 Shady Ln, Chestertown, NY 12817

$75,000

— beds— baths— sq ft

6 E Shore Dr, Adirondack, NY 12808

$375,000

2 beds1 bath768 sq ft

543 Valley Farm Rd, Pottersville, NY 12860

Property at William Hill Rd, Chester, NY

$125,000 Last sold price

— beds— baths— sq ft

William Hill Rd, Chester, NY

Listing by William Raveis-New York LLC

Property at L1.1 Elk Glade Rd, Chestertown, NY 12817

$110,000 Last sold price

— beds— baths— sq ft

L1.1 Elk Glade Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at L27 Carriage Knolls Rd, Chestertown, NY 12817

$29,000 Last sold price

— beds— baths— sq ft

L27 Carriage Knolls Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 51 Mountain Ln, Chestertown, NY 12885

$215,000 Last sold price

— beds— baths— sq ft

51 Mountain Ln, Chestertown, NY 12885

Listing by Davies-Davies & Assoc Real Est

Property at L12 Adirondack Heights Rd Lot 6, Chester, NY 12817

$79,500 Last sold price

— beds— baths— sq ft

L12 Adirondack Heights Rd Lot 6, Chester, NY 12817

Listing by Gallo Realty ADK Inc

Property at L17 Off Vanderwalker Rd, Chester, NY 12817

$43,000 Last sold price

— beds— baths— sq ft

L17 Off Vanderwalker Rd, Chester, NY 12817

Listing by Four Seasons Sotheby's International Realty

Property at L14 Potter Brook Rd, Chestertown, NY 12817

$32,000 Last sold price

— beds— baths— sq ft

L14 Potter Brook Rd, Chestertown, NY 12817

Listing by Gallo Realty ADK Inc

Property at 6 E Shore Dr, Chestertown, NY 12817

$75,000 Last sold price

— beds— baths— sq ft

6 E Shore Dr, Chestertown, NY 12817

Listing by KW Platform

$32,000

— beds— baths— sq ft

Potter Brook Rd, Chestertown, NY 12817

$115,000

— beds— baths— sq ft

71 Snowshoe Rdg, Warrensburg, NY 12885

$29,000

— beds— baths— sq ft

56 Carriage Knolls Rd, Chestertown, NY 12817

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Based on information submitted to the MLS GRID as of Sun Dec 28 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.

Recently Sold Homes in Chestertown

There are currently 36 recently sold homes for sale in Chestertown at a median listing price of $299K. 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 161 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 1 multi-family unit 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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