Chestertown MD FSBO Homes (143)

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Homes For Sale

$459,000

2 Bed
2.0 Bath
1,496 Sqft
36225 Sqft(Lot)

114 Ryan Court , Chestertown, MD

Perched above the peaceful waters of rosin creek, this charming waterfront cottage offers a rare opportunity to... Read More

Homes For Sale

$649,000

3 Bed
2.5 Bath
2,296 Sqft
2968 Sqft(Lot)

129 N Queen Street N N, Chestertown, MD

Welcome to 129 n. queen street situated in one of historic chestertown's most desirable and sought after... Read More

Coming Soon

Homes For Sale

$865,000

2 Bed
2.0 Bath
1,966 Sqft
399881 Sqft(Lot)

26889 Morgnec Road , Chestertown, MD

This waterfront farmette is a rare find just a few minutes from downtown chestertown and features extensive... Read More

Homes For Sale

$795,000

4 Bed
4.0 Bath
4,401 Sqft
22194 Sqft(Lot)

211 David Drive , Chestertown, MD

Big, bold, and beautiful! this wonderfully updated 2 story brick colonial in chestertown is just minutes walking... Read More

Homes For Sale

$579,900

1 Bath
1,148 Sqft
140350 Sqft(Lot)

5179 Quaker Neck Road , Chestertown, MD

A one-of-a-kind historic treasure reimagined for modern living step into history with this extraordinary greek... Read More

Homes For Sale

$1,200,000

5 Bed
4.5 Bath
3,078 Sqft
83200 Sqft(Lot)

22153 1st Point Road , Chestertown, MD

Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly... Read More

Homes For Sale

$364,900

3 Bed
2.5 Bath
1,724 Sqft
4864 Sqft(Lot)

216 Silver Heel Road , Chestertown, MD

Welcome to this move-in ready home, situated on a premium corner lot in the village at chestertown! this... Read More

Homes For Sale

$289,000

3 Bed
1.5 Bath
1,248 Sqft
87120 Sqft(Lot)

1106 Round Top Road , Chestertown, MD

Opportunity knocks! this 3-bedroom, 1.5-bath rancher sits on a spacious 2-acre lot in queen anne’s county. enjoy... Read More

Coming Soon

Homes For Sale

$749,900

5 Bed
3.0 Bath
3,394 Sqft
43560 Sqft(Lot)

7988 Aldan Drive , Chestertown, MD

This is a stunning property! it combines elegance and functionality with its spacious layout, beautiful... Read More

Pending

Vacant Land For Sale

$135,000

586,318 Sqft
586317.6 Sqft(Lot)

None , Chestertown, MD

13.5 wooded acres with very limited access on north side of chestertown. should be excellent deer hunting. 16'... Read More

Homes For Sale

$485,000

2 Bed
2.5 Bath
1,476 Sqft
3450 Sqft(Lot)

101 S Mill Street , Chestertown, MD

Historic charm with a modern floor plan. live just around the corner walking to the shops, galleries, and... Read More

Pending

Homes For Sale

$285,000

3 Bed
2.0 Bath
1,232 Sqft
15000 Sqft(Lot)

7483 Shortall Street , Chestertown, MD

Discover this delightful, move-in-ready ranch-style home in a peaceful chestertown setting. featuring three... Read More

Active Under Contract

Homes For Sale

$385,000

3 Bed
2.0 Bath
1,296 Sqft
21780 Sqft(Lot)

8605 Camp Road , Chestertown, MD

Your home sweet home retreat - a gorgeous 3 bedroom 2 full bathroom rancher with attached carport and unfinished... Read More

Homes For Sale

$1,459,000

3 Bed
2.5 Bath

Little Harbor Way #1, Chestertown, MD

Do your investments offer these dividends? a premier waterfront location in a premier condominium community... Read More

Coming Soon

Homes For Sale

$334,000

3 Bed
1.0 Bath
1,104 Sqft
20000 Sqft(Lot)

24095 Chestertown Road , Chestertown, MD

This gem just outside of chestertown will be active mid-april. new hvac, new roof, new flooring and other... Read More

Homes For Sale

$314,900

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

114 Darden Road , Chestertown, MD

All one floor living on quiet street with large fenced yard and mature trees close to the bay! lovely... Read More

Homes For Sale

$235,000

3 Bed
2.5 Bath
1,200 Sqft
3015 Sqft(Lot)

300 Hilltop Lane , Chestertown, MD

Welcome to this beautifully updated end-unit townhouse in the heart of chestertown! featuring 3 bedrooms and 2.5... Read More

Homes For Sale

$1,395,000

5 Bed
4.5 Bath
3,243 Sqft
2688 Sqft(Lot)

105 High Street , Chestertown, MD

This is your chance to own one of the most prominent homes in chestertown's historic district already completely... Read More

Vacant Land For Sale

$35,000

15,000 Sqft
15000 Sqft(Lot)

Cogar Road , Chestertown, MD

Welcome to your serene retreat on cogar road in charming chestertown, md! nestled on a generous 15,000 square... Read More

Active Under Contract

Homes For Sale

$434,500

4 Bed
2.0 Bath
1,766 Sqft
51836 Sqft(Lot)

130 Sheaffer Road , Chestertown, MD

Welcome to the grove in chestertown, a picturesque location in queen anne's county, located just a short drive... Read More

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Chestertown - Statistics and Home Trends

Actives Activity Chart

Homes For Sale By Owner in CHESTERTOWN 78

	Average Price
1 Bed Homes For Sale in CHESTERTOWN (2)	$ 371,500
2 Bed Homes For Sale in CHESTERTOWN (5)	$ 368,800
3 Bed Homes For Sale in CHESTERTOWN (55)	$ 511,453
4 Bed Homes For Sale in CHESTERTOWN (11)	$ 502,655
5+ Bed Homes For Sale in CHESTERTOWN (5)	$ 1,132,988

AVERAGE PRICE

$ 577,479

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 375

Multifamily For Sale By Owner in CHESTERTOWN 2

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

AVERAGE PRICE

$ 542,058

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 149

Land For Sale By Owner in CHESTERTOWN 43

	Average Price
Land For Sale in CHESTERTOWN (43)	$ 478,537

AVERAGE PRICE

$ 478,537

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

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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 04/14/2025. 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 04/14/2025

Chestertown MD FSBO Homes (143)

114 Ryan Court , Chestertown, MD

129 N Queen Street N N, Chestertown, MD

26889 Morgnec Road , Chestertown, MD

211 David Drive , Chestertown, MD

5179 Quaker Neck Road , Chestertown, MD

22153 1st Point Road , Chestertown, MD

216 Silver Heel Road , Chestertown, MD

1106 Round Top Road , Chestertown, MD

7988 Aldan Drive , Chestertown, MD

None , Chestertown, MD

101 S Mill Street , Chestertown, MD

7483 Shortall Street , Chestertown, MD

8605 Camp Road , Chestertown, MD

Little Harbor Way #1, Chestertown, MD

24095 Chestertown Road , Chestertown, MD

114 Darden Road , Chestertown, MD

300 Hilltop Lane , Chestertown, MD

105 High Street , Chestertown, MD

Cogar Road , Chestertown, MD

130 Sheaffer 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

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