28

Chestertown, NY Homes for Sale with Parking

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  • /31

    $1,899,000

    • 4 Beds
    • 2.5 Baths
    • 1,782 Sq Ft

    68 Birchwood Dr, Chestertown, NY 12817

    Experience the very best of Adirondack lakefront living in this private, completely renovated 4-bedroom, 2.5-bath Loon Lake retreat, complete with a RARE adjacent APA APPROVED buildable lakefront lot. Set along a sandy shoreline with a private dock, this beautifully maintained home offers spectacular lake views, classic Adirondack charm, and modern comfort.Expansive windows fill the home with

    Barbara Kearney Hunt Real Estate ERA

    68 Birchwood Dr, Chestertown, NY 12817
  • /13

    $200,000

    $25K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 704 Sq Ft

    12 Theriot Ave, Chestertown, NY 12817

    Cute as a button, recently renovated, single level living and conveniently located in Chestertown! Originally a two-bedroom home, it's currently configured as a spacious one-bedroom, with the option to easily restore it back to a two-bedroom to fit your needs. Living room and bedroom are virtually staged with furniture. The home features a new kitchen, open concept and scenic views of Panther

    Jill Brady Hunt Real Estate ERA

    12 Theriot Ave, 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
  • /16

    $185,000

    $14K PRICE DROP
    • 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- freshly painted and EASY TO SHOW- VACANT!

    Julia Pucciarelli Gallo Realty ADK Inc

    6378 U S 9, 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 outdoor activities year-round. The main house is a 3 BR, 2 BA home with sweeping views of the High Peaks. The updated kitchen features new appliances and hickory wood cabinets. The bright, airy dining/sunroom is wrapped

    Holly Dansbury Davies Davies & Associates Real Estate LLC

    342-346 Starbuck Hill Rd, Chestertown, NY 12817
  • /38

    $399,900

    $50K PRICE DROP
    • 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

    Robert Saumell Jr. KW Platform

    6324 State Route 9, Chestertown, NY 12817
  • /62

    $795,000

    $24K PRICE DROP
    • 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
  • /52

    $365,500

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    36 Ferris Rd, Chestertown, NY 12817

    If you've been looking for an updated and affordable home in Chestertown, you've just met your match. From the bright living room, to the galley kitchen equipped with stainless steel appliances and dining room with sliders to your private 1.44 acre oasis, there is so much to love about this home. The first floor primary bedroom has not only a walk-in closet but an additional closet as well,

    Jenna Frasier Selling ADK

    36 Ferris Rd, Chestertown, NY 12817
  • /36

    $475,500

    $22K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,369 Sq Ft

    7189 State Route 9, Chestertown, NY 12817

    Seasonal Adirondack Cottage with DOCK & BEACH on LOON LAKE! Beautiful 4-bedroom, 2-bath home on picturesque Loon Lake, located in the well-established Vista View Association with just eight other homeowners. This inviting Adirondack retreat features a spacious three-season porch with panoramic lake views-perfect for morning coffee, evening cocktails, or simply taking in the peaceful surroundings.

    Julia Pucciarelli Gallo Realty ADK Inc

    7189 State Route 9, 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
  • /35

    $639,000

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

    84 Marina Rd, Chestertown, NY 12817

    Enjoy Adirondack living in this beautiful Loon Lake home. This residence offers 3 bedrooms, 2 bathrooms with numerous upgrades and custom finishes including hardwood floors throughout, new windows and doors, granite countertops and brand new forced hot air heating system with dehumidifier and plumbing to add central air. The first floor offers the primary bedroom and bathroom, living room, open

    Sandra Engle-pratt Gore Mountain Real Estate Company

    84 Marina Rd, Chestertown, NY 12817
  • /57

    $740,000

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

    41 Moffitt Rd, Chestertown, NY 12817

    Chestertown Reduced Price, NEW Driveway, Loon Lake Area, 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

    Carol Monroe Najer Realty

    41 Moffitt Rd, Chestertown, NY 12817
  • /38

    $585,000

    • 4 Beds
    • 2 Baths
    • 1,948 Sq Ft

    548 White Schoolhouse Rd, Chestertown, NY 12817

    This charming 4 bedroom, 2 bath home is in a private setting, yet conveniently located to Loon Lake town, lakes, rivers and hiking/snowmobile trails. 2-car garage with storage and a separate car port., workshop, laundry area, HUGE living room/great room, cozy bedrooms, all-season porch with electric heat facing the sunsets at night. Full house generator, drilled well, septic, lovely landscaped

    Carol Monroe Najer Realty

    548 White Schoolhouse Rd, Chestertown, NY 12817
  • /28

    $320,000

    $75K PRICE DROP
    • 5 Beds
    • 1.5 Baths
    • 1,286 Sq Ft

    20 Vetter Ave, Chestertown, NY 12817

    Spacious 5-bedroom, 1.5-bath home situated on approximately 0.74 acres on a quiet street in the heart of Chestertown. The main level features a welcoming living room with a gas fireplace, creating a warm and inviting gathering space. Generously sized bedrooms provide ample living space, with several offering built-in shelving for added character and storage. An attached heated one-car garage

    Julia Pucciarelli Gallo Realty ADK Inc

    20 Vetter Ave, 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

    $899,000

    $201K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,482 Sq Ft

    190 Kingsley Lane Extension, Chestertown, NY 12817

    Loon Lake summers. Gore Mountain winters. Adirondack living year-round. Set on approximately two private acres, this furnished five-bedroom, three-bath retreat offers the rare combination of lake access, privacy, space and four-season recreation--all in one exceptional Adirondack property.Enjoy deeded rights to the private Loon Lake Heights sandy beach and an assigned boat slip, making

    Brooke Clark Four Seasons Sothebys International Realty

    190 Kingsley Lane Extension, Chestertown, NY 12817
  • /37

    $650,000

    $115K PRICE DROP
    • 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
  • /60

    $225,000

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    11 Overlook Ln S, Chestertown, NY 12817

    Escape to your Adirondack retreat in the private Green Mansions community! This affordable condo blends rustic charm with low-maintenance living, making it ideal as a cozy getaway or full-time residence. Enjoy three floors of living space, an in-unit washer and dryer, and a front deck with filtered views of Tripp Lake. Being sold mostly furnished, it's ready for you to move in and start enjoying

    Tammy Sutphin Hunt ERA

    11 Overlook Ln S, Chestertown, NY 12817
  • /36

    $290,000

    $10K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,021 Sq Ft

    22 Spring St, Chestertown, NY 12817

    Looking for that peaceful easy living? This is the home for you! Located at the end of a dead-end road, tucked away at the base of panther mountain, yet still within walking distance to Main Street with many accessible features. Sit on the expansive deck and enjoy the nice weather or cozy up indoors in any of the sitting areas with the ambiance of an electric fireplace. The home includes several

    Jenna Frasier Selling ADK

    22 Spring St, Chestertown, NY 12817
  • /31

    $224,000

    • 2 Beds
    • 1.5 Baths
    • 1,078 Sq Ft

    1 High Pines Terrace Unit E, Chestertown, NY 12817

    Welcome to East High Pines Terrace | Green MansionsCute as a button and ready for easy Adirondack living! Welcome to 1 East High Pines Terrace, a charming condo in the desirable Green Mansions community, where you can spend less time on maintenance and more time enjoying everything the Adirondacks have to offer.Whether you're looking for a year-round home, weekend escape, or

    Brooke Clark Four Seasons Sothebys International Realty

    1 High Pines Terrace Unit E, Chestertown, NY 12817
  • /12

    $110,000

    Unlisted Address

    A rare opportunity to create something special in the Lake George region. This 4.65-acre parcel offers an exceptional setting near Friends Lake, the Hudson River, skiing, hiking and other Adirondack recreation. Much of the groundwork is already in place, including excavation, an existing foundation footprint, beautiful original stonework and stone fireplace, and a newer foundation designed for

    Kyle Bryce Bryce Real Estate Inc

    Unlisted Address
  • /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 Palermo John R

    11 Overlook Ln N, Chestertown, NY 12817
  • /28

    $599,000

    $51K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 752 Sq Ft

    24 Memory Ln, Chestertown, NY 12817

    71 FT OF LAKEFRONT WITH SANDY SWIMMING, BEACH, DOCK & RARE LAKESIDE CABANA ON LOON LAKE! At the end of appropriately named Memory Lane, the lake has been the backdrop to generations of summer days--the kind filled with sandy feet, swims before breakfast, boat rides, and nights spent talking long after the sun disappears across the water. The seasonal cottage is charming and simple, exactly as a

    Ashley Nagy Davies Davies & Associates Real Estate LLC

    24 Memory Ln, 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 Real Estate ERA

    11 Overlook Ln S Unit B, Chestertown, NY 12817
  • /39

    $924,900

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,416 Sq Ft

    185 Chester Shores Dr, Chestertown, NY 12817

    Nestled along 100' of direct frontage on beautiful Loon Lake, this well-maintained year-round home offers breathtaking 180-degree lake and mountain views with the perfect setup for summer fun. Enjoy a sandy-bottom shoreline, two levels of usable waterfront with natural stone retaining walls, pressure-treated stairs, and a 40' x 6' permanent dock ideal for boating, swimming, fishing, kayaking, and

    Angie Mead Gallo Realty ADK, Inc

    185 Chester Shores Dr, Chestertown, NY 12817
  • /32

    $395,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,086 Sq Ft

    81 Clarkson Rd, Chestertown, NY 12817

    Escape to your own Adirondack hideaway. Nestled on a private .46-acre lot, this charming 2-bed, 2-bath home offers the perfect balance of rustic character and modern comfort. Just steps from Loon Lake, the property features filtered lake views and deeded rights to the sandy beach, giving you effortless access to swimming, paddling, and the full lake lifestyle. Step inside to a warm,

    Barbara Kearney Hunt Real Estate ERA

    81 Clarkson Rd, Chestertown, NY 12817
  • /37

    $650,000

    $115K PRICE DROP
    • 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

Home Price Trends

Median Sale Price
$310,000
Median Single Family Sale Price
$310,000
Median Townhouse Sale Price
$340,000
Median 2 Bedroom Sale Price
$224,000
Median 1 Bedroom Sale Price
$192,500
Average Price Per Sq Ft
$238
Number of Homes for Sale
10
Last 12 months Home Sales
11
Months of Supply
10.90
Median List Price
$269,500
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
20%
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