Chestertown MD FSBO Homes - Page 5 (140)

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We have 140 homes for sale by owner in Chestertown, MD. The median list price in Chestertown, MD is $265,633.

Vacant Land For Sale

$250,000

40,497 Sqft
40497 Sqft(Lot)

Scheeler Road Lot 2 , Chestertown, MD

This prime commercial lot offers an exceptional opportunity for your next business venture. situated at the... Read More

Pending

Homes For Sale

$399,000

3 Bed
2 Bath
1,560 Sqft
15000 Sqft(Lot)

109 Secor Road , Chestertown, MD

Charming home in chester harbor with water access! welcome to 109 secor rd, chestertown, md 21620, nestled on a... Read More

Pending

Homes For Sale

$299,900

3 Bed
2 Bath
1,288 Sqft
16720 Sqft(Lot)

7500 Shortall Street , Chestertown, MD

This charming 3-bedroom, 2-bath rancher nestled in a serene setting of quaker estates is a gem you won't want to... Read More

Vacant Land For Sale

$79,900

95,832 Sqft
95832 Sqft(Lot)

Fairlee Road , Chestertown, MD

Desirable wooded country 2.2 acre building parcel located near public boat landings between chestertown and rock... Read More

Homes For Sale

$698,000

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

$585,000

5 Bed
3.5 Bath
2,408 Sqft
35000 Sqft(Lot)

7938 Radcliffe Road , Chestertown, MD

This impeccably maintained home is a true standout and has it all! with 5 spacious bedrooms - with both main... Read More

Vacant Land For Sale

$80,000

102,802 Sqft
102801.6 Sqft(Lot)

9020 Georgetown Road , Chestertown, MD

Pretty wooded parcel recently surveyed with stakes clearly showing property boundaries. see documents for plat... Read More

Homes For Sale

$999,000

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

Active Under Contract

Homes For Sale

$322,000

3 Bed
2 Bath
1,470 Sqft
34804 Sqft(Lot)

305 Longfellow Drive , Chestertown, MD

Adorable and affordable in chester harbor community! this 4-bedroom 2 bath home is ready for you! situated on a... Read More

Vacant Land For Sale

$10,000

4,000 Sqft
4000 Sqft(Lot)

Texas Avenue , Chestertown, MD

Post auction: make an offer! lot of land in tolchester beach, maryland located within kent county. nearby... Read More

Pending

Homes For Sale

$289,000

3 Bed
3.5 Bath
1,840 Sqft
2160 Sqft(Lot)

104 Oak Leaf Drive , Chestertown, MD

Welcome to your new home in the vibrant community of chestertown! this beautiful 3-bedroom, 3.5-bath townhome... Read More

Active Under Contract

Homes For Sale

$286,900

3 Bed
2.5 Bath
1,420 Sqft
2480 Sqft(Lot)

116 Island Lark Way , Chestertown, MD

Welcome home to this beautiful end unit townhome in the newer community of the village at chestertown. this 3... Read More

Pending

Homes For Sale

$159,900

3 Bed
1 Bath
1,805 Sqft
8167 Sqft(Lot)

23110 Old Fairlee Road , Chestertown, MD

Welcome to this lovely home with a detached garage in the community of woods edge in kent county! the home... Read More

Homes For Sale

$165,000

3 Bed
1.0 Bath
1,152 Sqft
1980 Sqft(Lot)

240 N College Avenue , Chestertown, MD

Great investment property, currently rented with long term tenants. located in town with schools nearby. being... Read More

Homes For Sale

$1,450,000

3 Bed
3.5 Bath
4,446 Sqft

23393 Cacaway Farm Lane , Chestertown, MD

**exclusive waterfront craftsman home with sandy beach – a rare opportunity** nestled on the serene east fork of... Read More

Pending

Homes For Sale

$385,000

3 Bed
2.0 Bath
2,460 Sqft
15028 Sqft(Lot)

117 Primrose Road Primrose Road Road , Chestert...

Ranch home located in primrose point neighborhood( queen anne's county with chestertown address), only ten... Read More

Pending

Homes For Sale

$387,500

3 Bed
2.0 Bath
13373 Sqft(Lot)

409 Riverview Road , Chestertown, MD

Exceptional value-this charming cape cod home offers exceptional value with a recent $10,000 price reduction and... Read More

Homes For Sale

$515,000

3 Bed
1.5 Bath
1,076 Sqft
19910 Sqft(Lot)

116 Pine Chip Road , Chestertown, MD

Don’t let the outside fool you—this beautifully renovated 3-bedroom, 1.5-bathroom home offers three levels of... Read More

Pending

Homes For Sale

$649,900

4 Bed
3.0 Bath
2,672 Sqft
15980 Sqft(Lot)

110 Birch Run Road , Chestertown, MD

Custom - built 4 bedroom/3 bath custom built contemporary on a corner .37acre lot in the desirable neighborhood... Read More

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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 04/06/2025. 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 04/06/2025

Chestertown MD FSBO Homes - Page 5 (140)

Scheeler Road Lot 2 , Chestertown, MD

109 Secor Road , Chestertown, MD

7500 Shortall Street , Chestertown, MD

Fairlee Road , Chestertown, MD

11040 Kylie Lane , Chestertown, MD

24543 Chestertown Road , Chestertown, MD

7938 Radcliffe Road , Chestertown, MD

9020 Georgetown Road , Chestertown, MD

26865 Mallard Road , Chestertown, MD

305 Longfellow Drive , Chestertown, MD

Texas Avenue , Chestertown, MD

104 Oak Leaf Drive , Chestertown, MD

116 Island Lark Way , Chestertown, MD

23110 Old Fairlee Road , Chestertown, MD

240 N College Avenue , Chestertown, MD

23393 Cacaway Farm Lane , Chestertown, MD

117 Primrose Road Primrose Road Road , Chestert...

409 Riverview Road , Chestertown, MD

116 Pine Chip Road , Chestertown, MD

110 Birch Run Road , Chestertown, MD

For Sale By Owner New York

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For Sale By Owner West Virginia

Chestertown MD FSBO Homes - Page 5 (140)

Scheeler Road Lot 2 , Chestertown, MD

109 Secor Road , Chestertown, MD

7500 Shortall Street , Chestertown, MD

Fairlee Road , Chestertown, MD

11040 Kylie Lane , Chestertown, MD

24543 Chestertown Road , Chestertown, MD

7938 Radcliffe Road , Chestertown, MD

9020 Georgetown Road , Chestertown, MD

26865 Mallard Road , Chestertown, MD

305 Longfellow Drive , Chestertown, MD

Texas Avenue , Chestertown, MD

104 Oak Leaf Drive , Chestertown, MD

116 Island Lark Way , Chestertown, MD

23110 Old Fairlee Road , Chestertown, MD

240 N College Avenue , Chestertown, MD

23393 Cacaway Farm Lane , Chestertown, MD

117 Primrose Road Primrose Road Road , Chestert...

409 Riverview Road , Chestertown, MD

116 Pine Chip Road , Chestertown, MD

110 Birch Run Road , Chestertown, MD

Learn More About Chestertown, Maryland

For Sale By Owner New York

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For Sale By Owner Connecticut

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For Sale By Owner West Virginia

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