Chestertown NY Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
3,300
Status:
Active
MLS#:
207577
Type:
Single Family
Lot size:
3.9 Acres
Year built:
2002
Courtesy: Gallo Realty ADK, Inc Angela Mead 518-810-5885
View additional info

ADDITIONAL INFORMATION

Exquisite Schroon River Family Compound! Nestled on 3.9 private acres with direct frontage on the Schroon River, this exceptional property offers the perfect blend of luxury, comfort, and Adirondack charm. The heart of the home is a stunning custom kitchen filled with natural light, featuring quality finishes and a convenient prep sink. The elegant dining area showcases a statement chandelier and provides the perfect setting for gatherings. The private primary suite serves as a true retreat, complete with a clawfoot soaking tub, spacious walk-in closets, and abundant storage. The inviting living room features a wood-burning fireplace, creating a warm and welcoming atmosphere for entertaining family and friends. Additional living space includes a versatile loft, ideal for a home office or overflow sleeping area. The home offers multiple bedrooms and bathrooms to accommodate family and guests, including a large upstairs bedroom with its own full bath, plus two generously sized first-floor bedrooms and an additional full bath. 20 beds total! The finished lower level provides even more functional space with a laundry room, craft room, and recreation area. Outside, enjoy the peaceful sounds of the river from the expansive deck or screened porch. Additional amenities include a heated two-car garage with workshop, a detached boat garage, barn (at the road) and multiple outbuildings providing endless storage for all your Adirondack toys and equipment. A rare opportunity to own a private waterfront compound offering space, serenity, and year-round enjoyment on the Schroon River! House is coming furnished minus a few items on an exclusion list!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,416
Status:
Active
MLS#:
207363
Type:
Single Family
Lot size:
0.26 Acres
Year built:
1977
Courtesy: Gallo Realty ADK, Inc Angela Mead 518-810-5885
View additional info

ADDITIONAL INFORMATION

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 making lasting Adirondack memories. Additional outdoor amenities include a shed, carport, and kayak/paddleboard rack. Thoughtfully updated with a new high-efficiency propane heating and cooling system (2025), the home offers 2 bedrooms and 1 full bath on the main level with an open-concept kitchen, dining, and living area designed to capture lake views. The finished lower level includes 2 additional bedrooms, a full bath, recreation space perfect for guests, game nights, and a home office or gym, along with a laundry/mechanical room. Additional highlights include a wood-burning fireplace and whole-house Generac propane generator. Added bonus: The property previously received Town of Chester approvals and architectural plans for a proposed custom 1,564 sq. ft. lakefront home with dramatic 13' ceilings, offering future owners a rare opportunity to expand or create a custom Adirondack retreat with valuable groundwork already completed. Your Adirondack lake lifestyle starts here!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,404
Status:
Active
MLS#:
207143
Type:
Condo
Lot size:
0.02 Acres
Year built:
1964
Courtesy: Howard Hanna Capital, Inc. (Clifton Park) Joseph Cardinale 518-755-2064
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ADDITIONAL INFORMATION

Discover Adirondack living at its finest at 4A High Pines Terrace in Warrensburg, NY. Nestled on a quiet cul-de-sac, this beautifully renovated, move-in-ready home offers the perfect balance of privacy and convenience in the heart of the Adirondacks. This spacious residence features 2 bedrooms and 2 full bathrooms, along with an expansive living room and dining area designed for comfort and entertaining. The open-concept layout is highlighted by a cozy fireplace, abundant natural light, and large windows showcasing serene wooded views. Completely redone in 2022, this home boasts modern upgrades throughout, including granite countertops, refinished hardwood floors, updated appliances, and two fully remodeled bathrooms with stylish ceramic tile flooring. Fresh paint and thoughtful finishes create a clean, contemporary feel. Step outside onto the generous deck--perfect for relaxing or enjoying the peaceful surroundings. The HOA includes heat, adding exceptional value and convenience. Ideally located near Lake George, scenic hiking trails, and Gore Mountain, this property is perfect as a year-round residence, vacation home, or investment opportunity. Don't miss your chance to own this stunning Adirondack retreat. Agent is owner.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,400
Status:
Active
MLS#:
207011
Type:
Single Family
Lot size:
6.69 Acres
Year built:
2025
Courtesy: Gallo Realty ADK, Inc Angela Mead 518-810-5885
View additional info

ADDITIONAL INFORMATION

Tucked away on 6.5+ wooded acres at the end of a quiet dead-end road, this brand new 3-bedroom, 2-bath home offers the perfect blend of privacy and simplicity. Just completed and never lived in, with a new well, septic, and freshly seeded lawn--everything is done for you. Move right in and start enjoying easy, low-maintenance living in Chestertown. A peaceful setting you'll fall in love with the moment you arrive.

Beds:
1
Baths:
1.50
Sq.Ft.:
3,222
Status:
Active
MLS#:
206926
Type:
Single Family
Lot size:
0.09 Acres
Year built:
1885
Courtesy: Gallo Realty ADK, Inc Angela Mead 518-810-5885
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ADDITIONAL INFORMATION

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!

Beds:
6
Baths:
3.00
Sq.Ft.:
2,916
Status:
Active
MLS#:
202614239
Type:
Single Family
Lot size:
0.45 Acres
Year built:
1850
Courtesy: KW Platform Robert Saumell Jr. 518-926-8282
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ADDITIONAL INFORMATION

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 especially attractive for short-term rental use, with strong potential for consistent income. Inside, you'll find hardwood and tile flooring, a cozy living room with craftsman detail, and newer windows that fill the home with natural light. The layout offers multiple spaces to gather, relax, or spread out, while the enclosed porch adds even more versatility for entertaining or quiet downtime. Out back, the heated in-ground pool creates a private setting to unwind and enjoy the warmer months, adding to the property's appeal for both personal use and guests. Positioned right on Main Street, the home is close proximity to local shops, restaurants, and year-round recreation. With Loon Lake just minutes away and Lake George and Gore Mountain a short drive, this location makes it easy to enjoy everything the Adirondacks have to offer in every season. With its combination of space, location, and flexibility, this property offers a rare chance to own something that works just as well for personal use as it does as a high-performing investment!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,024
Status:
Active
MLS#:
202613847
Type:
Condo
Subdivision:
Green Mansions
Lot size:
0.01 Acres
Year built:
1980
Courtesy: Hunt ERA Barbara Kearney 215-219-6769
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ADDITIONAL INFORMATION

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 or pickleball. On-site storage provides convenient space for recreational gear and seasonal items. Ideal for weekend getaways or full-time living, this peaceful property is close to trails, lakes, and local attractions. HOA amenities include heat, exterior maintenance, snow removal, and more.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,700
Status:
Active
MLS#:
202613188
Type:
Single Family
Lot size:
7.89 Acres
Year built:
2023
Courtesy: Najer Realty Carol Monroe 518-494-2012
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ADDITIONAL INFORMATION

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 closet and full bath. 21/2 bathrooms, hardwood floors, gas fireplace, basement with a few rooms ready to be painted. High ceilings throughout. Landscaped with stone walls, full-house generator, central A/C, 2-car extra large attached garage. Wi-Fi, gas FP and heat connection to phone. Within 3 miles to Loon Lake Marina and Loon Lake. Within 15 miles to Gore Mountain Ski Area, hiking trails and many opportunities for outdoor recreation.Priced at $775,000.00

Beds:
2
Baths:
2.00
Sq.Ft.:
1,320
Status:
Active
MLS#:
202526662
Type:
Townhouse
Lot size:
0.03 Acres
Year built:
2003
Courtesy: CapMark Realty LLC John Gollhofer 518-586-2578
View additional info

ADDITIONAL INFORMATION

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 furnished in ADK decor. Schedule your preview today!

Beds:
2
Baths:
2.00
Sq.Ft.:
928
Status:
Active
MLS#:
202518188
Type:
Condo
Subdivision:
Green Mansions
Lot size:
0.01 Acres
Year built:
1976
Courtesy: John R. Palermo John Palermo 518-744-0271
View additional info

ADDITIONAL INFORMATION

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.

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Based on information from the Adirondack-Champlain Valley MLS as of the date posted below. The information provided by the Adirondack-Champlain Valley MLS is deemed reliable but not guaranteed. Information is provided for consumers’ personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2026 Adirondack-Champlain Valley MLS. All Rights Reserved.
Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

© 2026 Greater Capital Association of REALTORS (CRMLSNY). All rights reserved. The data relating to real estate for sale on this website have been downloaded from CRMLS. The IDX logo indicates listings of other real estate firms that are identified in the detailed listing information. Information herein is deemed reliable but not guaranteed, representations are approximate, individual verification's recommended. Per New York legal requirement, click here for the Standard Operating Procedures.



Chestertown Real Estate

Chestertown is located in New York. Chestertown, New York has a population of 587. Chestertown is more family-centric than the surrounding county with 25.9% of the households containing married families with children. The county average for households married with children is 24.15%.

The median household income in Chestertown, New York is $60,893. The median household income for the surrounding county is $68,765 compared to the national median of $69,021. The median age of people living in Chestertown is 48.3 years.

Chestertown Weather

The average high temperature in July is 80.5 degrees, with an average low temperature in January of 7.4 degrees. The average rainfall is approximately 45 inches per year, with 74.1 inches of snow per year.

Chestertown Map

Chestertown Real Estate Market Conditions

  • Median sales price

    $171,900
    13.4%
    change since last quarter
  • # Active listings

    31
    30-day change

Chestertown Schools and Demographics

Education near Chestertown, NY

City County
High School Graduates 75.61 91.51
College Degree - 2 year 20.4 12.28
College Degree - 4 year 23.95 33.05
Graduate Degree 8.65 12.98
Expenditures per Student 27,283 27,283
Students per Teacher 11.2 11.2

Elementary Schools near Chestertown, NY

Grades Students P/T Ratio ZIP
Warrensburg Elementary School PK - 06 400 11.7 12885

High Schools near Chestertown, NY

Grades Students P/T Ratio ZIP
Warrensburg Junior-Senior High School 07 - 12 369 10.9 12885

Ungraded Schools near Chestertown, NY

Grades Students P/T Ratio ZIP
Bolton Central School PK - 12 196 8.2 12814
Johnsburg Central School PK - 12 349 10.3 12853
Minerva Central School PK - 12 122 6.2 12857
North Warren Central School PK - 12 555 9.9 12817

Demographics near Chestertown, NY

City County
Neighborhood Type Small town
Population 587 65,692
Population Density 153 76
Median Age 48.3 46.8
People per Household 2.2 2.2
Median Household Income 60,893 68,765
Average Income per Capita 31,881 41,247

Real estate near Chestertown