15

Chestertown, NY Homes for Sale

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  • /54

    $659,000

    • 5 Beds
    • 4 Baths
    • 2,594 Sq Ft

    123 Forest Lake Rd, Chestertown, NY 12817

    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

    123 Forest Lake Rd, Chestertown, NY 12817
  • /50

    $350,000

    • 2 Beds
    • 1.5 Baths
    • 1,320 Sq Ft

    24 Balsam Crest Path Unit B, Chestertown, NY 12817

    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

    24 Balsam Crest Path Unit B, Chestertown, NY 12817
  • /38

    $449,900 Open Sat 12PM - 2PM

    • 6 Beds
    • 3 Baths
    • 2,916 Sq Ft

    6324 State Route 9, Chestertown, NY 12817

    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

    6324 State Route 9, Chestertown, NY 12817
  • /46

    $775,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    41 Moffitt Rd, Chestertown, NY 12817

    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 closet and full bath.21/2 bathrooms, hardwood floors, gas

    Carol Monroe Najer Realty

    41 Moffitt Rd, Chestertown, NY 12817
  • /6

    $46,000

    • Land
    • 1.57 Acres
    • $29,299 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 Mountain Ski area. Thearea offers numerous lakes and endless hiking trails. Located between the charming villages

    Norman Benjamin KW Platform

    8 Adirondack Heights Rd, Chestertown, NY 12817
  • /2

    $57,500

    • Land
    • 1.73 Acres
    • $33,237 per Acre

    37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chestertown, NY 12817

    This property has beach rights to two separate beaches. HOA Fee includes maintenance of beaches and road.Blue Bay Road is a Private Road.

    John Palermo John R. Palermo

    37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chestertown, NY 12817
  • /48

    $359,500 New Construction

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    71 Ferris Rd, Chestertown, NY 12817

    BRAND NEW 3bd/2bath manufactured home on a dead end road in Chestertown situated on a wooded 6.5+ acres. New well, septic, and lawn was just put in! Just completed and never lived in! Own a sparkling new year round home and don't worry about maintenance on anything for a very long time! Easy to show & even easier to fall in love with! Please remove shoes.

    Angie Mead Gallo Realty ADK Inc

    71 Ferris Rd, Chestertown, NY 12817
  • /53

    $850,000

    • 2 Beds
    • 1 Bath
    • 1,632 Sq Ft

    5537 State Route 8, Chestertown, NY 12817

    The Pine Tree Motel & Cabins is a well-maintained, family-owned hospitality property nestled among towering pines in the heart of the Adirondack Mountains. Located just minutes from Loon Lake with it's beach and boat launch, trails, and the charming hamlet of Chestertown, this established lodging destination offers a rare opportunity to own a turnkey, income-producing investment in one of Upstate

    Glenn T. Harris eXp Realty

    5537 State Route 8, Chestertown, NY 12817
  • /23

    $64,000

    • Land
    • 3.25 Acres
    • $19,692 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
  • /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
  • /26

    $195,000

    • 2 Beds
    • 1.5 Baths
    • 1,024 Sq Ft

    11 Overlook Ln S Unit B, Chestertown, NY 12817

    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

    11 Overlook Ln S Unit B, Chestertown, NY 12817
  • /34

    $225,000

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft

    60 Dixon Rd, Chestertown, NY 12817

    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

    60 Dixon Rd, Chestertown, NY 12817
  • /25

    $39,000

    • Land
    • 2.48 Acres
    • $15,726 per Acre

    37 Carriage Knolls Rd, Chestertown, NY 12817

    Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

    Walter Swartz Gallo Realty ADK Inc

    37 Carriage Knolls Rd, Chestertown, NY 12817
  • /60

    $589,900

    • 3 Beds
    • 2.5 Baths
    • 1,806 Sq Ft

    5107 New York 8, Chestertown, NY 12817

    Beautiful contemporary home offering 3 bedrooms, 2.5 bathrooms, and 2,742 sq ft of living space. This well-maintained property features a fully finished basement with exterior entry, providing great additional space for recreation, guests, or a home office. Ideally located directly across from Loon Lake, this home is also just minutes from the marina and public boat launch, and a 15-minute drive

    Angela Cugini-Girard eXp Realty

    5107 New York 8, Chestertown, NY 12817
  • /6

    $49,000

    • Land
    • 1.32 Acres
    • $37,121 per Acre

    14 Granite Ridge Rd, Chestertown, NY 12817

    Good price for your private Adirondack retreat. Small very private and wooded APA approved Subdivision of Adirondack Heights. Proposed home location is cleared - can still be changed. Green is all you can see. It is only a 10 minute drive to the Beach on Loon Lake or downtown Chestertown. On the way to the half hour trip to Gore Mountain for skiing - you pass the access to the Hudson River for

    Heidemarie Lane Big Hat Realty

    14 Granite Ridge Rd, Chestertown, NY 12817

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.

Frequently Asked Questions

What is the average home price in Chestertown, NY?
Homes for sale in Chestertown, NY have an average home price of $349,685.
How many homes have sold over the last 12 months in Chestertown, NY?
15 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, 12814, 12885 and 12853.
How much do you need to make to afford a house in Chestertown?
The median home price in Chestertown is $325,000. If you put a 20% down payment of $65,000 and had a 30-year fixed mortgage with an interest rate of 6.46%, your estimated principal and interest payment would be $1,640 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $70K a year to afford the median home price in Chestertown. Learn how much home you can afford with our Home Affordability Calculator.
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

Housing Trends

Median Sale Price
$310,000
Median Single Family Sale Price
$344,750
Median Townhouse Sale Price
$340,000
Median 2 Bedroom Sale Price
$195,000
Median 1 Bedroom Sale Price
$137,500
Average Price Per Sq Ft
$256
Number of Homes for Sale
5
Last 12 months Home Sales
15
Months of Supply
4.00
Median List Price
$325,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
35%
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