Chestertown MD FSBO Homes (24)

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We have 24 homes for sale by owner in Chestertown, MD. The median list price in Chestertown, MD is $228,744 and the average price per square foot is $135,496.

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Homes For Sale

$440,000

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

128 Edmore Road , Chestertown, MD

Wait until you see the 2nd floor suite! don't miss your opportunity to own in chester harbor! this property has... Read More

Homes For Sale

$274,000

3 Bed
1 Bath
1,056 Sqft
15000 Sqft(Lot)

118 Tuxedo Road , Chestertown, MD

Three bedroom/one bath rancher located in a water-oriented community just minutes from chestertown. there is a... Read More

Homes For Sale

$267,500

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

$339,000

3 Bed
2.0 Bath
15000 Sqft(Lot)

109 Tamarack Road , Chestertown, MD

Welcome to this beautiful 3-level colonial in the sought-after chester harbor community on the queen anne’s... Read More

Homes For Sale

$345,000

3 Bed
2.0 Bath
1,402 Sqft
15000 Sqft(Lot)

505 N Kent Street , Chestertown, MD

Charming rancher in sought-after byford development! nestled in the desirable byford development of chestertown,... Read More

Homes For Sale

$885,000

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

24576 Langford Road , Chestertown, MD

Highfield, has been home to the renown architectural historian michael bourne and his family for almost... Read More

Homes For Sale

$236,000

3 Bed
2.0 Bath
1,140 Sqft
3762 Sqft(Lot)

107 Chester Arms Drive , Chestertown, MD

This inviting one-level home offers easy one-level living. featuring luxury vinyl plank flooring , a stylish... Read More

Homes For Sale

$395,000

1 Bed
1.0 Bath
744 Sqft
1025 Sqft(Lot)

117 Court Street , Chestertown, MD

Truly fine example of italianate architecture nestled among lawyer's row in historic district of chestertown,... Read More

Homes For Sale

$399,900

5 Bed
3.0 Bath
3,389 Sqft
33000 Sqft(Lot)

25740 Collins Avenue , Chestertown, MD

Large home with private pool & separate apartment! nestled in a prime location, this solid, well-maintained... Read More

Pending

Homes For Sale

$399,000

3 Bed
2.0 Bath
1,811 Sqft
15000 Sqft(Lot)

149 Longfellow Drive , Chestertown, MD

Welcome to your dream home in the charming sought after community of chester harbor! this delightful property... Read More

Homes For Sale

$345,000

4 Bed
3.0 Bath
2,106 Sqft
41400 Sqft(Lot)

10705 Millbrook Drive , Chestertown, MD

Welcome to 10705 millbrook drive, a charming cape cod-style home located in the desirable chesapeake landing... Read More

Homes For Sale

$779,000

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

Pending

Homes For Sale

$549,900

4 Bed
2 Bath
3659 Sqft(Lot)

209 Queen Street N N, Chestertown, MD

Welcome to the historic fannie stuart home, c 1885 - a delightful victorian home, with the perfect blend of... Read More

Homes For Sale

$335,000

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

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

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

$725,000

3 Bed
3.0 Bath

117 N Water Street #1A, Chestertown, MD

Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch -... Read More

Homes For Sale

$579,000

2 Bed
2.5 Bath
1307 Sqft(Lot)

103 Landing Lane , Chestertown, MD

Discover this exquisite townhome nestled within the prestigious water-oriented community of chester river... Read More

Homes For Sale

$395,000

7 Bed
3.5 Bath
3,664 Sqft
5737 Sqft(Lot)

349 High Street , Chestertown, MD

Looking for something truly special? don't miss this unique offering, located in the vibrant heart of... Read More

Chestertown - Statistics and Home Trends

Actives Activity Chart

Homes For Sale By Owner in CHESTERTOWN 70

	Average Price
1 Bed Homes For Sale in CHESTERTOWN (2)	$ 371,500
2 Bed Homes For Sale in CHESTERTOWN (4)	$ 391,125
3 Bed Homes For Sale in CHESTERTOWN (51)	$ 503,783
4 Bed Homes For Sale in CHESTERTOWN (8)	$ 526,963
5+ Bed Homes For Sale in CHESTERTOWN (5)	$ 1,132,988

AVERAGE PRICE

$ 585,272

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 379

Multifamily For Sale By Owner in CHESTERTOWN 2

	Average Price
1 Bed Multifamily For Sale in CHESTERTOWN (2)	$ 364,950

AVERAGE PRICE

$ 548,551

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 149

Land For Sale By Owner in CHESTERTOWN 41

	Average Price
Land For Sale in CHESTERTOWN (41)	$ 485,139

AVERAGE PRICE

$ 485,139

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

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Learn More About Chestertown, Maryland

Currently there are 70 homes for sale and 41 vacant land for sale in Chestertown

Currently Chestertown has 113 properties on the market for sale. The inventory was last updated 03/13/2025. Of these properties, 70 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 $585,272, the average condo price in Chestertown, is $548,551. The average price per square foot of the active inventory is $176. 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 03/13/2025

Chestertown MD FSBO Homes (24)

128 Edmore Road , Chestertown, MD

118 Tuxedo Road , Chestertown, MD

21217 Texas Avenue , Chestertown, MD

109 Tamarack Road , Chestertown, MD

505 N Kent Street , Chestertown, MD

24576 Langford Road , Chestertown, MD

107 Chester Arms Drive , Chestertown, MD

117 Court Street , Chestertown, MD

25740 Collins Avenue , Chestertown, MD

149 Longfellow Drive , Chestertown, MD

10705 Millbrook Drive , Chestertown, MD

212 Landing Lane , Chestertown, MD

209 Queen Street N N, Chestertown, MD

107 Dutchess Road , Chestertown, MD

116 Island Lark Way , Chestertown, MD

23110 Old Fairlee Road , Chestertown, MD

409 Riverview Road , Chestertown, MD

117 N Water Street #1A, Chestertown, MD

103 Landing Lane , Chestertown, MD

349 High Street , Chestertown, MD

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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

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

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Learn More About Chestertown, Maryland

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