Chestertown MD FSBO Homes - Page 3 (106)

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We have 106 homes for sale by owner in Chestertown, MD. The median list price in Chestertown, MD is $645,866.

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

$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

$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

Active Under Contract

Homes For Sale

$324,900

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

Active Under Contract

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

Active Under Contract

Homes For Sale

$236,000

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

107 Chester Arms Drive , Chestertown, MD

Why rent when you can own for less?!?! three beds, 2 baths!! this inviting one-level home offers easy one-level... 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

$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 quaint little spot in chestertown. nearly new, beautiful home... Read More

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

Active Under Contract

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

$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

$5,000

15,000 Sqft
15000 Sqft(Lot)

Towhee Road , Chestertown, MD

Online auction: bidding begins 4/22/2025 @ 10:00 am. bidding ends 4/23/2025 @ 12:40 pm. list price is suggested... Read More

Active Under Contract

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

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

$327,750

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

$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

Multifamily For Sale

$299,000

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

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

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

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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 04/25/2025. 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 04/25/2025

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Chestertown MD FSBO Homes - Page 3 (106)

226 S Water Street , Chestertown, MD

21217 Texas Avenue , Chestertown, MD

118 Tuxedo Road , Chestertown, MD

109 Tamarack Road , Chestertown, MD

505 N Kent Street , Chestertown, MD

107 Chester Arms Drive , Chestertown, MD

24576 Langford Road , Chestertown, MD

110 Flying Cloud Court , Chestertown, MD

10578 Tonopah Road , Chestertown, MD

123 Burchard Sawmill Road , Chestertown, MD

Walnut Point Road , Chestertown, MD

Towhee Road , Chestertown, MD

23620 Lands End Road , Chestertown, MD

149 Longfellow Drive , Chestertown, MD

10705 Millbrook Drive , Chestertown, MD

866 Washington Avenue , Chestertown, MD

866 Washington Avenue , Chestertown, MD

Melitota Road , Chestertown, MD

Lot 24 & 25 Buck Neck Road , Chestertown, MD

212 Landing Lane , Chestertown, MD

Learn More About Chestertown, Maryland

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