Chestertown MD FSBO Homes - Page 3 (66)

Sort By

List
Map

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

Homes For Sale

$220,000

3 Bed
2.5 Bath
1,200 Sqft
3015 Sqft(Lot)

300 Hilltop Lane , Chestertown, MD

Welcome to this beautifully updated end-unit townhouse in the heart of chestertown! featuring 3 bedrooms and 2.5... Read More

Homes For Sale

$1,395,500

5 Bed
4.5 Bath
3,243 Sqft
2688 Sqft(Lot)

105 High Street , Chestertown, MD

This is your chance to own one of the most prominent homes in chestertown's historic district already completely... Read More

Homes For Sale

$199,900

2 Bed
1 Bath
896 Sqft
11375 Sqft(Lot)

110 Philosophers Terrace , Chestertown, MD

Two bedroom/one bath dwelling located within the town limits of chestertown zoned rb offers great investment... Read More

Homes For Sale

$569,000

2 Bed
2.5 Bath

103 Landing Lane , Chestertown, MD

Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable chester... Read More

Homes For Sale

$425,000

4 Bed
2.0 Bath
2,184 Sqft
15000 Sqft(Lot)

128 Edmore Road , Chestertown, MD

Your dream eastern shore retreat awaits! welcome to this meticulously maintained home, where charm and comfort... Read More

Active Under Contract

Homes For Sale

$319,000

4 Bed
2.0 Bath
1,404 Sqft
19000 Sqft(Lot)

306 Cedar Street , Chestertown, MD

Lovely 4 bedroom, 2 bath cape cod located in college heights. the house has been freshly painted inside and out... Read More

Active Under Contract

Homes For Sale

$499,900

4 Bed
3.5 Bath
2,280 Sqft
10327 Sqft(Lot)

314 Devon Drive , Chestertown, MD

Welcome to 314 devon drive in chestertown—a beautifully designed 4-bedroom, 3.5-bath home where comfort meets... Read More

Homes For Sale

$998,000

3 Bed
3.5 Bath
3782 Sqft(Lot)

226 S Water Street , Chestertown, MD

Newly finished 3 bedroom townhouses with nearly all the desired attributes of town living, with harbor and... Read More

Homes For Sale

$232,000

2 Bed
1.0 Bath
912 Sqft
16000 Sqft(Lot)

21217 Texas Avenue , Chestertown, MD

Move in ready!! adorable, affordable, move in ready & two blocks from the chesapeake bay! appliances, roof,... Read More

Homes For Sale

$845,000

3 Bed
2.5 Bath
4,023 Sqft
217800 Sqft(Lot)

24576 Langford Road , Chestertown, MD

Sellers are meeting the market with substantial price reduction. highfield was designed and built by michael... Read More

Homes For Sale

$349,900

3 Bed
2.5 Bath
1,856 Sqft
4000 Sqft(Lot)

110 Flying Cloud Court , Chestertown, MD

Single family home (tax record is incorrect) in picturesque town surrounding washington college. nearly new,... Read More

Active Under Contract

Homes For Sale

$329,900

3 Bed
2.5 Bath
15400 Sqft(Lot)

10578 Tonopah Road , Chestertown, MD

Imagine waking up to gentle breezes and the promise of waterfront living. that's what awaits you in this... Read More

Pending

Homes For Sale

$5,500,000

5 Bed
6.5 Bath
9,852 Sqft
3507016 Sqft(Lot)

23620 Lands End Road , Chestertown, MD

Beautifully situated on the east fork of langford creek, this light filled custom built home and property... Read More

Homes For Sale

$299,000

3 Bed
2.0 Bath
9054 Sqft(Lot)

866 Washington Avenue , Chestertown, MD

Prime investment opportunity in chestertown with leases in place!!! this duplex property offers versatility,... Read More

Homes For Sale

$759,000

3 Bed
3.5 Bath

212 Landing Lane , Chestertown, MD

Nestled along the tranquil western shore of the chester river, this beautiful townhome in chester river landing... Read More

Homes For Sale

$349,900

3 Bed
2.0 Bath
1,392 Sqft
33300 Sqft(Lot)

109 Wilton Road , Chestertown, MD

Welcome to this charming 3-bedroom, 2-bathroom rancher, offering the perfect blend of comfort and convenience... Read More

Homes For Sale

$325,000

3 Bed
2 Bath
15276 Sqft(Lot)

107 Dutchess Road , Chestertown, MD

Welcome to chester harbor - a family oriented place to live! the chester harbor community has a voluntary hoa... Read More

Homes For Sale

$679,000

4 Bed
3.5 Bath
3,684 Sqft
114127 Sqft(Lot)

11040 Kylie Lane , Chestertown, MD

Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on urieville lake! this stunning... Read More

Pending

Homes For Sale

$475,000

3 Bed
2.0 Bath
3,280 Sqft
436036 Sqft(Lot)

24543 Chestertown Road , Chestertown, MD

Nestled on 10 scenic acres just outside of chestertown, this spacious 3,280 sq ft home offers incredible... Read More

Active Under Contract

Homes For Sale

$950,000

4 Bed
3.0 Bath
3,355 Sqft
39537 Sqft(Lot)

26865 Mallard Road , Chestertown, MD

A highly coveted chester river waterfront just minutes from historic downtown chestertown. this large home has... Read More

First
1
2
3
4
Last

Learn More About Chestertown, Maryland

Currently there are 78 homes for sale and 43 vacant land for sale in Chestertown

Currently Chestertown has 123 properties on the market for sale. The inventory was last updated 06/11/2025. Of these properties, 78 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 $577,479, the average condo price in Chestertown, is $542,058. The average price per square foot of the active inventory is $175. This is based the living area square footage.

Over the last year, there have been 337 of properties sold in Chestertown. Of these properties, 302 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 $372,324. Single family homes have been selling for 260 per square foot of living area. The average sales price of the condos for sale in Chestertown, is $363,253. Condos have been selling for 173 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 MD FSBO Homes - Page 3 (66)

300 Hilltop Lane , Chestertown, MD

105 High Street , Chestertown, MD

110 Philosophers Terrace , Chestertown, MD

103 Landing Lane , Chestertown, MD

128 Edmore Road , Chestertown, MD

306 Cedar Street , Chestertown, MD

314 Devon Drive , Chestertown, MD

226 S Water Street , Chestertown, MD

21217 Texas Avenue , Chestertown, MD

24576 Langford Road , Chestertown, MD

110 Flying Cloud Court , Chestertown, MD

10578 Tonopah Road , Chestertown, MD

23620 Lands End Road , Chestertown, MD

866 Washington Avenue , Chestertown, MD

212 Landing Lane , Chestertown, MD

109 Wilton Road , Chestertown, MD

107 Dutchess Road , Chestertown, MD

11040 Kylie Lane , Chestertown, MD

24543 Chestertown Road , Chestertown, MD

26865 Mallard Road , Chestertown, MD

For Sale By Owner Pennsylvania

Statistics Bottom Ads 2

For Sale By Owner North Carolina

Statistics Bottom Ads 3

For Sale By Owner New Mexico

Chestertown MD FSBO Homes - Page 3 (66)

300 Hilltop Lane , Chestertown, MD

105 High Street , Chestertown, MD

110 Philosophers Terrace , Chestertown, MD

103 Landing Lane , Chestertown, MD

128 Edmore Road , Chestertown, MD

306 Cedar Street , Chestertown, MD

314 Devon Drive , Chestertown, MD

226 S Water Street , Chestertown, MD

21217 Texas Avenue , Chestertown, MD

24576 Langford Road , Chestertown, MD

110 Flying Cloud Court , Chestertown, MD

10578 Tonopah Road , Chestertown, MD

23620 Lands End Road , Chestertown, MD

866 Washington Avenue , Chestertown, MD

212 Landing Lane , Chestertown, MD

109 Wilton Road , Chestertown, MD

107 Dutchess Road , Chestertown, MD

11040 Kylie Lane , Chestertown, MD

24543 Chestertown Road , Chestertown, MD

26865 Mallard Road , Chestertown, MD

Learn More About Chestertown, Maryland

For Sale By Owner Pennsylvania

Statistics Bottom Ads 2

For Sale By Owner North Carolina

Statistics Bottom Ads 3

For Sale By Owner New Mexico

Statistics Bottom Ads 4

YouTube Video