Chestertown MD FSBO Homes (23)

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We have 23 homes for sale by owner in Chestertown, MD. The median list price in Chestertown, MD is $73,257.

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

$485,000

3 Bed
2.5 Bath
1,648 Sqft
179467 Sqft(Lot)

123 Burchard Sawmill Road , Chestertown, MD

This is it! this is the one you and your horse have been dreaming about! absolutely darling 4+ acre farmette!... Read More

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

$449,000

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

Active Under Contract

Homes For Sale

$305,000

3 Bed
2.0 Bath
1,196 Sqft
19599 Sqft(Lot)

10640 Watonga Road , Chestertown, MD

Located in chesapeake landing, this property offers access to a community area with a boat launch and docks,... Read More

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

$349,900

3 Bed
2.0 Bath
20240 Sqft(Lot)

249 Duke Of Kent Street , Chestertown, MD

Lovely all one floor living in quiet neighborhood with updated features throughout! brand new gorgeous kitchen... Read More

Active Under Contract

Homes For Sale

$395,000

3 Bed
2.5 Bath
2,162 Sqft
21875 Sqft(Lot)

204 Pine Cove Lane , Chestertown, MD

Discover the perfect blend of modern design and rustic charm at 204 pine cove lane, a stunning 3-bedroom,... Read More

Pending

Homes For Sale

$310,000

3 Bed
1.0 Bath
1,188 Sqft
56628 Sqft(Lot)

10061 Flatland Road , Chestertown, MD

Charming, very well-maintained home located just outside historic chestertown. the side entrance has a spacious... Read More

Active Under Contract

Homes For Sale

$364,440

3 Bed
2.0 Bath
1,008 Sqft
39590 Sqft(Lot)

105 Justin Buch Drive , Chestertown, MD

Welcome to 105 justin buch drive, a delightful single-family home nestled in a quiet community on the queen... Read More

Coming Soon

Homes For Sale

$339,000

3 Bed
1.5 Bath
15000 Sqft(Lot)

109 Tamarack Road , Chestertown, MD

Charming 3-bed, 1.5 bath home with screened porch, fireplace, basement & 2-car garage! stay tuned!

Pending

Homes For Sale

$950,000

3 Bed
3.5 Bath
2,800 Sqft

225 S Water Street #6, Chestertown, MD

This end unit waterfront condo in scott's point has beautiful water views up and down the chester river! it is a... Read More

Homes For Sale

$350,000

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

$469,500

3 Bed
2.5 Bath
43560 Sqft(Lot)

220 Blakefield Drive , Chestertown, MD

Brand new gorgeous custom home completed & ready for a family to start their next adventure. fall in love with... 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

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

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

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

Chestertown - Statistics and Home Trends

Actives Activity Chart

Homes For Sale By Owner in CHESTERTOWN 62

	Average Price
1 Bed Homes For Sale in CHESTERTOWN (2)	$ 371,500
2 Bed Homes For Sale in CHESTERTOWN (3)	$ 432,333
3 Bed Homes For Sale in CHESTERTOWN (45)	$ 521,865
4 Bed Homes For Sale in CHESTERTOWN (7)	$ 539,386
5+ Bed Homes For Sale in CHESTERTOWN (5)	$ 1,154,125

AVERAGE PRICE

$ 603,842

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 398

Multifamily For Sale By Owner in CHESTERTOWN 2

	Average Price
1 Bed Multifamily For Sale in CHESTERTOWN (2)	$ 379,950

AVERAGE PRICE

$ 566,527

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 155

Land For Sale By Owner in CHESTERTOWN 41

	Average Price
Land For Sale in CHESTERTOWN (41)	$ 500,564

AVERAGE PRICE

$ 500,564

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

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Learn More About Chestertown, Maryland

Currently there are 62 homes for sale and 41 vacant land for sale in Chestertown

Currently Chestertown has 105 properties on the market for sale. The inventory was last updated 02/21/2025. Of these properties, 62 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 $603,842, the average condo price in Chestertown, is $566,527. The average price per square foot of the active inventory is $184. 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 02/21/2025

Chestertown MD FSBO Homes (23)

117 Court Street , Chestertown, MD

123 Burchard Sawmill Road , Chestertown, MD

23620 Lands End Road , Chestertown, MD

25740 Collins Avenue , Chestertown, MD

10640 Watonga Road , Chestertown, MD

149 Longfellow Drive , Chestertown, MD

10705 Millbrook Drive , Chestertown, MD

249 Duke Of Kent Street , Chestertown, MD

204 Pine Cove Lane , Chestertown, MD

10061 Flatland Road , Chestertown, MD

105 Justin Buch Drive , Chestertown, MD

109 Tamarack Road , Chestertown, MD

225 S Water Street #6, Chestertown, MD

107 Dutchess Road , Chestertown, MD

220 Blakefield Drive , Chestertown, MD

11040 Kylie Lane , Chestertown, MD

116 Island Lark Way , Chestertown, MD

23393 Cacaway Farm Lane , Chestertown, MD

117 N Water Street #1A, Chestertown, MD

103 Landing Lane , 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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