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Chestertown, NY Homes for Sale

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  • /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

    $369,900

    • 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
  • /41

    $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

    $55,000

    • Land
    • 1.57 Acres
    • $35,032 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

    $26,900

    • Land
    • 2.40 Acres
    • $11,208 per Acre

    L26 Potter Brook Rd, Chestertown, NY 12817

    Opportunity is knocking! This land is waiting for your dreams to be realized. Conveniently located between Gore Mountain, and the town of Warrensburg with accessibility to I-87. Right down the road from Circle B Ranch and friends Lake, this is prime location. This land could be the foundation of your Adirondack getaway!

    Bradley Laustrup Properly

    L26 Potter Brook Rd, Chestertown, NY 12817

Why Live in Chestertown

Celebrating its 225th anniversary in July 2024 with a car show, bounce house, food trucks and corn hole, Chestertown is a small Adirondacks town driven by community. “Events and local businesses separate this small town from larger cities,” says Julia Pucciarelli, local chamber of commerce member and Realtor with Gallow Realty ADK. “The community is driven by wonderful organizations, like the Chestertown Rotary, the Historical Society, Friends of the Library and the Tri-lakes Community Alliance.” Pucciarelli has lived in Chestertown for the pas ...

Frequently Asked Questions

What is the average home price in Chestertown, NY?
Homes for sale in Chestertown, NY have an average home price of $376,228.
Are home prices dropping in Chestertown?
Yes, home prices in Chestertown are down 10% 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 12845, 12817, 12853, 12883 and 12885.
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 6.84%, your estimated principal and interest payment would be $1,780 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $76K 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

Housing Trends

Median Sale Price
$335,000
Median Single Family Sale Price
$350,000
Median Townhouse Sale Price
$296,500
Median 2 Bedroom Sale Price
$189,000
Median 1 Bedroom Sale Price
$163,148
Average Price Per Sq Ft
$240
Number of Homes for Sale
8
Last 12 months Home Sales
41
Months of Supply
2.30
Median List Price
$339,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-1%
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