Chestertown, NY Homes for Sale

/51
$325,000
- 4 Beds
- 4 Baths
- 840 Sq Ft
5 Overlook Ln N Unit B & D, Chestertown, NY 12817

Rare, year-round double Condominium at 5 Overlook Lane, B/D in Warrensburg, NY—nestled in a peaceful, park-like setting with deeded lake rights to beautiful Tripp Lake. This spacious, renovated unit sleeps up to 16 and features two living areas with fireplaces, a custom kitchen, updated baths, and a large deck with seasonal lake views. Offering 4 en-suite bedrooms, sleeping loft, a wet bar,

Joseph Cardinale

Howard Hanna Capital, Inc. (Clifton Park)

(518) 656-8047

5 Overlook Ln N Unit B & D, Chestertown, NY 12817
/71
$359,000
- 3 Beds
- 2 Baths
- 1,080 Sq Ft
22 Shady Ln, Chestertown, NY 12817

Enjoy swimming, paddling and fishing at the perfect Adirondack getaway with complete privacy, cabin, large deck, shed, and 250' of frontage on the Schroon River. The driveway meanders through the woods and arrives at a nice clearing and the cabin overlooking the river. The backdrop of mature white pine and hemlock trees provide beauty and privacy for the 1,080 sq.' 3 bedroom, 1 and 3/4 bath

Michael Fudzinski WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

22 Shady Ln, Chestertown, NY 12817
/34
$295,000
- 2 Beds
- 1 Bath
- 1,080 Sq Ft
347 Landon Hill Rd, Chestertown, NY 12817

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

Carol Monroe Najer Realty

347 Landon Hill Rd, Chestertown, NY 12817
/26
$489,000
- 3 Beds
- 1 Bath
- 920 Sq Ft
18 Woodcliff Acres, Chestertown, NY 12817

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

18 Woodcliff Acres, Chestertown, NY 12817
/38
$339,000
- 3 Beds
- 1 Bath
- 1,152 Sq Ft
68 Elks Glade Rd, Chestertown, NY 12817

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

68 Elks Glade Rd, Chestertown, NY 12817
/48
$674,900
- 3 Beds
- 3 Baths
- 1,800 Sq Ft
209 Chester Shores Ridge, Chestertown, NY 12817

***OPEN HOUSE: SUNDAY JUNE 8th 1-4PM!*** 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

Nicholas Khachadourian KW Platform

209 Chester Shores Ridge, Chestertown, NY 12817
/17
$189,000
- 2 Beds
- 1.5 Baths
- 928 Sq Ft
11 Overlook Ln N, Chestertown, NY 12817

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

11 Overlook Ln N, Chestertown, NY 12817
/12
$90,000
- Land
- 4.65 Acres
- $19,355 per Acre
115 Atateka Dr, Chestertown, NY 12817

GREAT DEAL! Fantastic location by lakes, skiing and rivers . Lot has been excavated partially cleared of tall trees and perk test done for septic. Winchip engineering 2022- Two wells. One original and other drilled. The original dug well is lined with stone well. Second well drilled. Three stone walls and stone fireplace remain Original foundation Minutes to Friends Lake, Minutes to Hudson

Kyle Bryce Bryce Real Estate Inc

115 Atateka Dr, Chestertown, NY 12817
/53
$799,900
- 5 Beds
- 2 Baths
- 1,768 Sq Ft
5387-5391 New York 8, Chestertown, NY 12817

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

5387-5391 New York 8, Chestertown, NY 12817
/55
$349,900
- 3 Beds
- 1 Bath
- 1,651 Sq Ft
11 Mill St, Chestertown, NY 12817

This is the ideal getaway to relax and take in the sights and smells of the Adirondacks.This Circa 1900 Farmhouse and Barn sit on over one acre and has direct waterfront on Faxon Pond. Unbelievable sunsets! Launch your canoe or kayak for a morning/ evening of taking in the sights, or cast a line for some laid back fishing. Large back yard. Fantastic Views. 15 minutes to Gore Mountain. Minutes to

Valerie Erceg Davies-Davies & Assoc Real Est

11 Mill St, Chestertown, NY 12817
/20
$235,000
- 2 Beds
- 2.5 Baths
- 1,927 Sq Ft
6367 U S 9, Chestertown, NY 12817

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

6367 U S 9, Chestertown, NY 12817
/8
$199,000
- 1 Bed
- 1.5 Baths
- 3,222 Sq Ft
6378 U S 9, Chestertown, NY 12817

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

6378 U S 9, Chestertown, NY 12817
/14
$70,000
- Land
- 3.25 Acres
- $21,538 per Acre
64 Carriage Knolls Rd, Chestertown, NY 12817

Cleared and leveled lot 5-minutes outside of Chestertown. Private setting set-back in the woods. (though building lot is cleared) Perfect for a full-time home or getaway cabin. Electricity and cable available at the front of property. Large pile of rocks from excavation for property delineation or retaining areas. Must walk this property to appreciate the beauty and serenity. Adjacent 11+ acre

Walter Swartz Gallo Realty ADK Inc

64 Carriage Knolls Rd, Chestertown, NY 12817
/11
$105,000
- Land
- 10 Acres
- $10,500 per Acre
5127 New York 8, Chestertown, NY 12817

Escape to the heart of the Adirondack Mountains with this expansive 10-acre parcel — a perfect canvas for your dream home or vacation retreat. Just a short walk from the calm, clear waters of Loon Lake, this property offers peaceful seclusion alongside endless outdoor adventure. Enjoy 539 acres of pristine lake activities like swimming, boating, and fishing, plus nearby hiking trails, dining, and

Jaclyn Scott Crystal Coleman Realty LLC

5127 New York 8, Chestertown, NY 12817
/51
$225,000
- 3 Beds
- 1 Bath
- 920 Sq Ft
25 Schroon River Forest, Chestertown, NY 12817

Classic 3 season camp on the scenic Schroon River. This camp has been the seasonal get-a-way from the same family since1976. The camp lies within minutes to several lakes in the area. It's a mobile home w/ a full length addition, full foundation & attic. The camp offers a generous amount of space w/ a family room & a nice sized screened in porch, 3bd/1bath, eat-in kitchen & front room. It also

Angie Mead Gallo Realty ADK Inc

25 Schroon River Forest, Chestertown, NY 12817
/6
$49,000
- Land
- 1.57 Acres
- $31,210 per Acre
8 Adirondack Heights Rd, Chestertown, NY 12817

Situated in the heart of the Adirondack Park, this building lot is ideal for your year round homeor seasonal get-a way. Enjoy all the park has to offer, a few short miles to the Hudson river forcanoeing, kayaking, tubing and fishing and a quick 20 minute ride to Gore Mtn Ski area. Thearea offers numerous lakes and endless hiking trails. Located between the charming villages ofWarrensburg and

Norman Benjamin KW Platform

8 Adirondack Heights Rd, Chestertown, NY 12817
/9
$199,000
- Land
- 4.00 Acres
- $49,750 per Acre
L10 New York 8, Chestertown, NY

4-acre undeveloped commercial land parcel in the hamlet of Chestertown. Between Dollar General, North Warren Central School, and North Warren Emergency Squad. Mix of cleared areas and wooded areas with a rolling slope. With approvals this property would be ideal for a business, apartments, offices, storage facility, and so much more. With frontage on Route 8 as well as Cougar Lane the access to

Walter Swartz Gallo Realty ADK Inc

L10 New York 8, Chestertown, NY
/2
$76,900
- Land
- 5 Acres
- $14,874 per Acre
0 Landon Hill Rd Unit KEY880970, Chestertown, NY 12817

Lovely lot on Landon hill road, more pics to come.

Jason Minch William Raveis-New York LLC

0 Landon Hill Rd Unit KEY880970, Chestertown, NY 12817
/2
$70,900
- Land
- 3.72 Acres
- $19,059 per Acre
0 Landon Hill Rd Unit KEY880968, Chestertown, NY 12817

Lovely lot on Landon Hill road, more photos to come.

Jason Minch William Raveis-New York LLC

0 Landon Hill Rd Unit KEY880968, Chestertown, NY 12817

New York Chestertown

Why Live in Chestertown

Chestertown, NY, a small Adirondack town, is known for its strong community spirit and outdoor recreational opportunities. Celebrating its 225th anniversary in July 2024, the town hosts events like car shows and festivals, showcasing its vibrant local culture. Residents enjoy four seasons of activities, from swimming and fishing in natural lakes to skiing and snowmobiling at nearby mountain resorts. Main Street is a hub of activity, featuring eateries such as the Bullhouse Kitchen and Bar, which offers Latin American-influenced comfort food, and the Main Street Ice Cream Parlor, serving breakfast and lunch. Cultural attractions include the Carol Theater and Birds of a Feather Studio and Gallery. Chestertown's historic district is walkable and bikeable, with easy access to Interstate 87, connecting to Albany and New York City. The town is safer than the national average, providing peace of mind for families. Homes range from historic houses to newer builds, with many purchased as vacation homes, though year-round residency is growing. Flooding can affect properties along routes 8 and 9, particularly near Chester Creek. Outdoor enthusiasts can explore nearby Gore Mountain and Pharaoh Lake Wilderness Area, offering skiing, hiking, and water activities. The Chester Challenge encourages hiking on local trails, promoting physical fitness. Chestertown's community organizations and events, such as Woof Stock and the Krazy Downhill Derby, further enrich the town's appeal, making it a unique place to live or visit.

Learn more about living in Chestertown

Frequently Asked Questions

What is the average home price in Chestertown, NY?

Homes for sale in Chestertown, NY have an average home price of $375,585.

Are home prices dropping in Chestertown?

Yes, home prices in Chestertown are down 4% in the last 12 months.

How many homes have sold over the last 12 months in Chestertown, NY?

41 homes have sold in Chestertown, NY over the last 12 months.

What are the most popular zip codes in Chestertown, NY?

The most popular zip codes in Chestertown, NY include 12817, 12815, 12885, 12860 and 12814.

How much do you need to make to afford a house in Chestertown?

The median home price in Chestertown is $339,000. If you put a 20% down payment of $67,800 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $1,750 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $75K a year to afford the median home price in Chestertown.

How are the schools in Chestertown, NY?

Chestertown, NY has highly rated public and private schools. The best school in Chestertown based on Niche Grade is North Warren Central School. Browse all the schools in Chestertown, NY to learn more.

Home Trends in Chestertown, NY

On average, homes in Chestertown, NY sell after 38 days on the market compared to the national average of 50 days. The median sale price for homes in Chestertown, NY over the last 12 months is $335,000, consistent with the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$335,000

Median Single Family Sale Price

$349,900

Median Townhouse Sale Price

$296,500

Median 2 Bedroom Sale Price

$189,000

Median 1 Bedroom Sale Price

$135,000

Average Price Per Sq Ft

$254

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.50

Median List Price

$339,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

How to Buy a Home How to Finance a Home How to Sell a Home

Chestertown Types of Homes for Sale

More About Living in Chestertown

Homes in Nearby Neighborhoods

Bolton Homes for Sale

Homes in Nearby Cities

Homes in Nearby Counties

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