19

Chestertown, NY Homes for Sale with Acreage

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  • /112

    $599,000

    Open Sun 1PM - 3PM $151K PRICE DROP
    • 6 Beds
    • 5.5 Baths
    • 3,372 Sq Ft

    10 Landon Hill Rd, Chestertown, NY 12817

    *****OPEN HOUSE SUNDAY August 2nd 1pm -3pm*****Now offered at $599,000. With its rare combination of space, privacy, and flexibility, this Adirondack retreat is now more attainable than ever. Tucked away on 2.67 private Adirondack acres just 7 minutes to Friends Lake and Loon Lake, 15 minutes to Lake George/Bolton Landing, and 20 minutes to Gore Mountain, this fully renovated 3,372 sq ft

    John LaRocca Davies-Davies & Assoc Real Est

    10 Landon Hill Rd, Chestertown, NY 12817
  • /30

    $799,000

    $74K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 651 Sq Ft

    773 Atateka Dr, Chestertown, NY 12817

    Rustic seasonal lakefront camp with 439 feet of frontage including your own cove on private Friends Lake on the East Shore. Lauch capability on your own frontage. Nestled among the pines on a rare 3.42 secluded acres with a dock, small boat house (for storage only), one car garage and lakeside patio. Owned by only one family for three generations. Step back to a simpler time at this charming

    Jill Brady Hunt Real Estate ERA

    773 Atateka Dr, Chestertown, NY 12817
  • /41

    $1,925,000

    • Land
    • 72.12 Acres
    • $26,692 per Acre

    203 Tripp Lake Rd, Chestertown, NY 12817

    Positioned in the heart of the Adirondacks' thriving tourism corridor, Green Mansions Golf Course presents a rare opportunity to acquire a 72+ acre turn-key recreational and hospitality property with immediate income and exceptional future development potential. Ideally located just 20 minutes from Lake George, Bolton Landing and 30 minutes to Gore Mountain and Saratoga Springs, this property is

    Ashley Nagy Davies-Davies & Assoc Real Est

    203 Tripp Lake Rd, Chestertown, NY 12817
  • /47

    $699,900

    • 4 Beds
    • 3 Baths
    • 3,977 Sq Ft

    342-346 Starbuck Hill Rd, Chestertown, NY 12817

    Tucked away on over 5 private, wooded acres yet minutes from I-87 and town, this meticulously maintained Adirondack retreat offers the perfect blend of serenity, convenience, and versatility. Whether you are seeking a primary home, a vacation escape, or a rental property with proven rental history, here is a rare opportunity to have it all. The main house is a 3 BR, 2 BA home with sweeping views

    Holly Dansbury Davies-Davies & Assoc Real Est

    342-346 Starbuck Hill Rd, Chestertown, NY 12817
  • /62

    $819,000

    • 3 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    26 Emily Ln, Chestertown, NY 12817

    Where Adirondack privacy meets the Loon Lake lifestyle, this custom-built year-round home offers deeded docking and sandy beach access, all while being privately set on 5+ acres. Thoughtfully designed for comfort, character, and four-season living, this 3-bedroom, 2.5-bath home features an impressive great room with cathedral ceilings, a stone wood-burning fireplace, and a dramatic window wall

    Walter Swartz Gallo Realty ADK Inc

    26 Emily Ln, Chestertown, NY 12817
  • /25

    $329,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft

    527 Potter Brook Rd, Chestertown, NY 12817

    This quaint ADK get away is looking for some TLC to make this your own special place. Set on 2.5+ private acres off a quiet country road at the southern gateway to the Adirondack Park. This home offers easy access to year-round outdoor activities. Gore Mountain Ski Resort and Lake George are both just 30 minutes away, while shopping, fine dining, and health care are only minutes away in historic

    Jennifer Sherry Sherwood Group, LLC

    527 Potter Brook Rd, Chestertown, NY 12817
  • /51

    $740,000

    New Construction $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    41 Moffitt Rd, Chestertown, NY 12817

    Chestertown, Truly a Spectacular Constructed Nearly new and quality 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

    Carol Monroe Najer Realty

    41 Moffitt Rd, Chestertown, NY 12817
  • /23

    $420,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    14 Vanderwalker Rd, Chestertown, NY 12817

    Opportunity awaits in the Adirondacks! Nestled on 3.33 private, wooded acres, this 3-bedroom, 2-bath home offers the perfect blend of privacy, comfort, and convenience. Enjoy the warmth and efficiency of radiant floor heat throughout, along with a spacious great room featuring soaring cathedral ceilings--ideal for gathering with family and friends. The generous primary suite includes a private

    Barbara Kearney Hunt Real Estate ERA

    14 Vanderwalker Rd, Chestertown, NY 12817
  • /52

    $989,000

    $111K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,482 Sq Ft

    190 Kingsley Lane Extension, Chestertown, NY 12817

    **Offered completely turnkey--including furnishings--Top of the Rock is ready for you to simply arrive, unpack, and start enjoying the Adirondack lifestyle from day one.** Nestled among towering pines in a peaceful setting, this exceptional home offers the perfect balance of privacy, comfort, and coveted deeded access to beautiful Loon Lake. Wake up to birdsong and coffee on the patio before

    Brooke Clark Four Seasons Sotheby's International Realty

    190 Kingsley Lane Extension, 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
  • /37

    $765,000

    • 3 Beds
    • 1 Bath
    • 1,220 Sq Ft

    7278 U S 9, Chestertown, NY 12817

    Rich in Adirondack history and surrounded by nature, Calamity Cove is a one-of-a-kind year-round retreat offering over 3 acres across two separately deeded parcels with direct boating access to beautiful Loon Lake. Originally home to a campground and later a popular local gathering place, the property has evolved into the peaceful waterfront escape it is today while preserving pieces of its

    Angie Mead Gallo Realty ADK, Inc

    7278 U S 9, Chestertown, NY 12817
  • /25

    $59,000

    $11K PRICE DROP
    • Land
    • 3.25 Acres
    • $18,154 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
  • /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
  • /36

    $699,900

    • Land
    • 337 Acres
    • $2,077 per Acre

    0 Friends Lake Rd Unit 11555363, Chestertown, NY 12817

    With nearly 2,200 feet of frontage along the Upper Hudson River, a wild, whitewater backcountry river, and immediate access to nearly 1,600 acres of State Forest Preserve, the Hudson River Woods & Wildwater property is the "complete package" of Adirondack property. With over 4,500 feet of road frontage (with electric) on Friends Lake Road, it's an ideal location for a camp, first or

    John O'Donnell Timberland Realty

    0 Friends Lake Rd Unit 11555363, Chestertown, NY 12817
  • /37

    $765,000

    • 3 Beds
    • 1 Bath
    • 1,220 Sq Ft

    7278 State Route 9, Chestertown, NY 12817

    Rich in Adirondack history and surrounded by nature, Calamity Cove is a one-of-a-kind year-round retreat offering over 3 acres across two separately deeded parcels with direct boating access to beautiful Loon Lake. Originally home to a campground and later a popular local gathering place, the property has evolved into the peaceful waterfront escape it is today while preserving pieces of its

    Angie Mead Gallo Realty ADK Inc

    7278 State Route 9, Chestertown, NY 12817
  • /52

    $874,900

    • 5 Beds
    • 3.5 Baths
    • 2,750 Sq Ft

    18 E Kelm Pond Rd, Chestertown, NY 12817

    Extraordinary Adirondack retreat situated on 10 private acres, ideally located between Forest Lake and Kelm Pond, offering the perfect blend of privacy, comfort, and versatility. Built in 2016, this unique property features a beautifully designed 3-bedroom, 2.5-bath main residence plus a separate 2-bedroom, 1-bath guest suite along with an oversized garage, making it ideal for extended family,

    Angela Cugini-Girard eXp Realty

    18 E Kelm Pond Rd, Chestertown, NY 12817
  • /102

    $4,497,000

    • 7 Beds
    • 11 Baths
    • 11,038 Sq Ft

    46 Fiddlehead Bay Rd, Chestertown, NY 12817

    Set along the pristine shores of private Friends Lake in the southeastern Adirondacks, this extraordinary year-round Camp is a rare legacy estate where timeless Adirondack architecture meets refined luxury.Thoughtfully designed and built by its current owners, the 10,000 plus square-foot residence showcases exceptional craftsmanship and authentic Adirondack character. Antique doors reclaimed

    Lisa Paschke Engel & Volkers Lake Placid Real Estate

    46 Fiddlehead Bay Rd, 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
  • /39

    $499,000

    $40K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,552 Sq Ft

    50 Kingsley Ln, Chestertown, NY 12817

    Welcome to **50 Kingsley Lane**, where Adirondack charm, modern comfort, and four-season adventure come together. Nestled among the trees just minutes from Loon Lake, Gore Mountain, and endless hiking, boating, and snowmobiling, this home is the perfect year-round retreat or vacation getaway .Offering **2,552 sq. ft.** of finished living space plus an additional **1,032 sq. ft. walk-out

    Brooke Clark Four Seasons Sotheby's International Realty

    50 Kingsley Ln, Chestertown, NY 12817

Home Price Trends

Median Sale Price
$310,000
Median Single Family Sale Price
$310,000
Median Townhouse Sale Price
$342,000
Median 2 Bedroom Sale Price
$225,000
Median 1 Bedroom Sale Price
$205,500
Average Price Per Sq Ft
$229
Number of Homes for Sale
12
Last 12 months Home Sales
11
Months of Supply
13.10
Median List Price
$239,900
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
22%
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