Chestertown MD FSBO Homes (104)

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We have 104 homes for sale by owner in Chestertown, MD. The median list price in Chestertown, MD is $175,450.

Vacant Land For Sale

$449,000

87,991 Sqft
87991.2 Sqft(Lot)

Walnut Point Road , Chestertown, MD

Extremely rare offering! 2 acre recorded waterfront parcel in quaker neck on walnut point road with 211 feet of... Read More

Vacant Land For Sale

$10,000

15,000 Sqft
15000 Sqft(Lot)

Towhee Road , Chestertown, MD

Online auction: bidding begins 02/28/2025 @ 10:00 am. bidding ends 03/04/2025 @ 12:05 pm. list price is... 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

$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

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

Coming Soon

Homes For Sale

$360,000

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

110 Flying Cloud Court , Chestertown, MD

Beautifully kept home with laminate plank flooring, white kitchen complete with stainless appliances and side... 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

Homes For Sale

$334,900

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

Active Under Contract

Vacant Land For Sale

$29,000

87,120 Sqft
87120 Sqft(Lot)

Melitota Road , Chestertown, MD

2-acre wooded parcel on l road. short distance to chestertown and amenities. see documents for additional... Read More

Multifamily For Sale

$334,900

1,224 Sqft
9054 Sqft(Lot)

866 Washington Avenue , Chestertown, MD

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

Coming Soon

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

Vacant Land For Sale

$8,000

18,150 Sqft
18150 Sqft(Lot)

Lot 24 & 25 Buck Neck Road , Chestertown, MD

Chesapeake landing offers a voluntary home owners association. at $40 annually, community members have access... 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

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

Active Under Contract

Homes For Sale

$685,000

4 Bed
3.5 Bath
2,512 Sqft
44867 Sqft(Lot)

317 Union Church Road , Chestertown, MD

Welcome to 317 union church rd, stunning custom built farmhouse with all the bells and whistles perfectly sited... 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

Active Under Contract

Homes For Sale

$337,000

3 Bed
2.0 Bath
1,872 Sqft
15000 Sqft(Lot)

10724 Foreston Road , Chestertown, MD

Your dream home is waiting! this remodeled home is waiting for you in the serene water-privileged community of... Read More

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Chestertown - Statistics and Home Trends

Actives Activity Chart

Homes For Sale By Owner in CHESTERTOWN 61

	Average Price
1 Bed Homes For Sale in CHESTERTOWN (1)	$ 348,000
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

$ 599,142

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 397

Multifamily For Sale By Owner in CHESTERTOWN 2

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

AVERAGE PRICE

$ 562,610

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)	$ 497,587

AVERAGE PRICE

$ 497,587

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

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Learn More About Chestertown, Maryland

Currently there are 61 homes for sale and 41 vacant land for sale in Chestertown

Currently Chestertown has 104 properties on the market for sale. The inventory was last updated 02/21/2025. Of these properties, 61 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 $599,142, the average condo price in Chestertown, is $562,610. 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

For Sale By Owner South Carolina

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For Sale By Owner Illinois

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Chestertown MD FSBO Homes (104)

Walnut Point Road , Chestertown, MD

Towhee Road , Chestertown, MD

10640 Watonga Road , Chestertown, MD

23620 Lands End Road , Chestertown, MD

25740 Collins Avenue , Chestertown, MD

149 Longfellow Drive , Chestertown, MD

110 Flying Cloud Court , Chestertown, MD

10705 Millbrook Drive , Chestertown, MD

249 Duke Of Kent Street , Chestertown, MD

866 Washington Avenue , Chestertown, MD

Melitota Road , Chestertown, MD

866 Washington Avenue , Chestertown, MD

123 Burchard Sawmill Road , Chestertown, MD

Lot 24 & 25 Buck Neck Road , Chestertown, MD

212 Landing Lane , Chestertown, MD

204 Pine Cove Lane , Chestertown, MD

317 Union Church Road , Chestertown, MD

10061 Flatland Road , Chestertown, MD

105 Justin Buch Drive , Chestertown, MD

10724 Foreston Road , 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

For Sale By Owner South Carolina

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