Chestertown NY FSBO Homes (52)

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We have homes for sale by owner in Chestertown, NY. The median list price in Chestertown, NY is $334,831 and the average price per square foot is $26,759.

Homes For Sale

$674,900

3 Bed
3 Bath
1,800 Sqft
0.49 Acre(Lot)

209 Chester Shores Ridge, Chestertown, NY

***open house: sunday june 8th 1-4pm!*** step within this adirondack 4-season home in the highly desired chester... Read More

Condo For Sale

$189,000

2 Bed
2 Bath
928 Sqft
0.01 Acre(Lot)

11K Overlook Lane Ln, Chestertown, NY

This condominium has deck with partial lake view and is a member of the green mansions tennis and swim club... Read More

Active Under Contract

Homes For Sale

$295,000

2 Bed
1 Bath
1,080 Sqft
9.18 Acres(Lot)

347 Landon Hill Road, Chestertown, NY

One of a kind setting, this well built beloved ranch home with 9+ acres, 3 bedrooms, large lr with stone... Read More

Active Under Contract

Condo For Sale

$140,000

1 Bed
2 Bath
1,100 Sqft
0.03 Acre(Lot)

1 High Pines Terrace #1C, Chestertown, NY

Best and final deadline 5/27 12:00 pm nestled in the heart of the adk, this beautiful turnkey condo offers... Read More

Pending

Condo For Sale

$199,000

1 Bed
1 Bath
480 Sqft
0.01 Acre(Lot)

1 Vista View Drive, Chestertown, NY

Seasonal adirondack cottage w/ dock + beach on motorized loon lake! this cottage is part of a 4+ acre direct... Read More

Homes For Sale

$799,900

5 Bed
2 Bath
1,768 Sqft
0.98 Acre(Lot)

53875391 State Route 8, Chestertown, NY

Experience rustic charm and modern comfort in this beautifully renovated farmhouse with 173 feet of direct... Read More

Vacant Land For Sale

$74,900

1.79 Acres(Lot)

L45 Marina Road, Chestertown, NY

This is two lots combined for better access and development and has beach rights to two beaches shown on map.... Read More

Active Under Contract

Condo For Sale

$135,000

1 Bed
1 Bath
900 Sqft
0.02 Acre(Lot)

112 Green Mansions Road #1A, Chestertown, NY

Don't miss this gorgeous condo in the heart of the adirondacks. the only unit with a stunning solarium, it fills... Read More

Vacant Land For Sale

$179,900

3.14 Acres(Lot)

2 Dixon Road, Chestertown, NY

Fish, paddle, build! your very own 509' of private frontage plus your own mini island on the schroon river! over... Read More

Homes For Sale

$369,900

3 Bed
1 Bath
1,651 Sqft
1.04 Acres(Lot)

11 Mill Street, Chestertown, NY

This is the ideal getaway to relax and take in the sights and smells of the adirondacks.this circa 1900... Read More

Vacant Land For Sale

$179,900

3.14 Acres(Lot)

2 Dixon Road, Chestertown, NY

Fish, paddle, build! your very own 509' of private frontage plus your own mini island on the schroon river! over... Read More

Pending

Homes For Sale

$1,025,000

4 Bed
3 Bath
2,289 Sqft
5.2 Acres(Lot)

170 Tripp Lake Road, Chestertown, NY

Private lakefront paradise! tucked away at the end of a long driveway on 5.2 acres, this meticulously maintained... Read More

Pending

Homes For Sale

$579,000

3 Bed
2 Bath
1,665 Sqft
6.47 Acres(Lot)

2754 Schroon River Road, Chestertown, NY

Cedar sided contemporary with 955' of direct frontage on the stocked schroon river! sprawling 6.5 acres with... Read More

Pending

Townhome For Sale

$275,000

3 Bed
2 Bath
1,248 Sqft
0.02 Acre(Lot)

16 B Evergreen Road, Chestertown, NY

This wonderful townhome has been loved by the same owner for 38 years. this community of 28 homes is located on... Read More

Vacant Land For Sale

$70,000

3.25 Acres(Lot)

64 Carriage Knolls Road, Chestertown, NY

Cleared and leveled lot 5-minutes outside of chestertown. private setting set-back in the woods. (though... Read More

Vacant Land For Sale

$275,000

5.23 Acres(Lot)

51 Mountain Lane, Chestertown, NY

This 5.23-acre parcel with 249ft of lake frontage offers a rare opportunity to build your dream lakefront... Read More

Pending

Homes For Sale

$374,900

3 Bed
2 Bath
1,196 Sqft
3.76 Acres(Lot)

4785 Ny8, Chestertown, NY

Escape to your own hideaway with this charming 3bed, 2bath retreat nestled on nearly 4 acres. perfectly situated... Read More

Pending

Homes For Sale

$290,000

3 Bed
2 Bath
2,128 Sqft
14 Acres(Lot)

650 Landon Hill Road, Chestertown, NY

Lovely home with 3 bedrooms, 2 baths, bonus room, 3 season porch, deck, fireplace, 2800 square feet of great... Read More

Vacant Land For Sale

$105,000

10 Acres(Lot)

5127 State Route 8, Chestertown, NY

Escape to the heart of the adirondack mountains with this expansive 10-acre parcel — a perfect canvas for your... Read More

Pending

Homes For Sale

$245,900

1 Bed
2 Bath
1,500 Sqft
0.29 Acre(Lot)

6404 Route 9, Chestertown, NY

Currently being used as offices. could be converted to a single family. kitchen is upstairs - kitchenette... Read More

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Chestertown - Statistics and Home Trends

Actives Activity Chart

Homes For Sale By Owner in Chestertown 20

	Average Price
1 Bed Homes For Sale in Chestertown (1)	$ 245,900
2 Bed Homes For Sale in Chestertown (3)	$ 263,967
3 Bed Homes For Sale in Chestertown (14)	$ 386,986
5+ Bed Homes For Sale in Chestertown (2)	$ 399,000

AVERAGE PRICE

$ 323,963

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 231

Land For Sale By Owner in Chestertown 35

	Average Price
Land For Sale in Chestertown (35)	$ 283,385

AVERAGE PRICE

$ 283,385

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

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Learn More About Chestertown, New York

Currently there are 20 homes for sale and 35 vacant land for sale in Chestertown

Currently Chestertown has 55 properties on the market for sale. The inventory was last updated 06/11/2025. Of these properties, 20 single family homes are for sale by their owners in Chestertown, and 0 condos are for sale by their owners in Chestertown. The average price of the single family homes for sale in Chestertown, is $323,963, the average condo price in Chestertown, is $283,385. The average price per square foot of the active inventory is $116. This is based the living area square footage.

Over the last year, there have been 0 of properties sold in Chestertown. Of these properties, 0 single family homes have sold by their owners in Chestertown, and 0 condos have sold by their owners in Chestertown. The average sales price of the single family homes sold in Chestertown, is $. Single family homes have been selling for per square foot of living area. The average sales price of the condos for sale in Chestertown, is $. Condos have been selling for per square foot of living area.

The most active subdivisions with listings for sale in Chestertown, are:

If you are thinking of selling your Chestertown home, try our flat fee listing service, Our list fees start at $449, and may save you $15,000 in real estate commissions. Click here to start saving.

Disclaimer: Listing broker has attempted to offer accurate data, but buyers/lessees are advised to confirm all information IDX information is provided exclusively for consumers' personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or the MLS from liability.
This data up-to-date as of 06/11/2025

Chestertown NY FSBO Homes (52)

209 Chester Shores Ridge, Chestertown, NY

11K Overlook Lane Ln, Chestertown, NY

347 Landon Hill Road, Chestertown, NY

1 High Pines Terrace #1C, Chestertown, NY

1 Vista View Drive, Chestertown, NY

53875391 State Route 8, Chestertown, NY

L45 Marina Road, Chestertown, NY

112 Green Mansions Road #1A, Chestertown, NY

2 Dixon Road, Chestertown, NY

11 Mill Street, Chestertown, NY

2 Dixon Road, Chestertown, NY

170 Tripp Lake Road, Chestertown, NY

2754 Schroon River Road, Chestertown, NY

16 B Evergreen Road, Chestertown, NY

64 Carriage Knolls Road, Chestertown, NY

51 Mountain Lane, Chestertown, NY

4785 Ny8, Chestertown, NY

650 Landon Hill Road, Chestertown, NY

5127 State Route 8, Chestertown, NY

6404 Route 9, Chestertown, NY

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Chestertown - Statistics and Home Trends

Actives Activity Chart

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

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Learn More About Chestertown, New York

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