Skip to main content
Homes for sale in Chestertown, Maryland
Maryland

Homes for Sale in Chestertown

“63 active listings in Chestertown, Maryland · Average list price $1,052,248”

63 listings
Avg $1,052,248
227 days avg
Search All 63 Homes
Explore
Market Overview

Chestertown Real Estate at a Glance

Current market statistics for Chestertown, MD

63

Active Listings

$1.1M

Avg Price

$839

Price/Sqft

227

Avg Days

Price Range

From

$5,000

To

$38,200,000

Property Types

Other

52

Single Family

7

Commercial

1

Townhouse

1

Nearby Cities

Explore homes for sale in cities near Chestertown, Maryland

Baltimore, MD
343 homes for sale
Within 25 mi
Havre DE Grace, MD
84 homes for sale
Within 25 mi
Pasadena, MD
83 homes for sale
Within 25 mi
Bel Air, MD
82 homes for sale
Within 25 mi
Aberdeen, MD
79 homes for sale
Within 25 mi
Middle River, MD
73 homes for sale
Within 25 mi
Chester, MD
56 homes for sale
Within 25 mi
Dundalk, MD
53 homes for sale
Within 25 mi
Listing selection

Homes to Explore

Active listings from the chestertown collection

104 ACORN Drive, Chestertown, MD - $275K

$275K

104 ACORN Drive

Chestertown, MD

234 N COLLEGE Avenue - Single Family for sale in Chestertown, MD

$79K

234 N COLLEGE Avenue

Chestertown, MD

6746 QUAKER NECK Road - Single Family for sale in Chestertown, MD

$339K

6746 QUAKER NECK Road

Chestertown, MD

123 TRAFFORD Drive - Single Family for sale in Chestertown, MD

$370K

123 TRAFFORD Drive

106 HARLAN Loop - Single Family for sale in Chestertown, MD

$425K

106 HARLAN Loop

More listings

More from Chestertown

More active listings from across the Chestertown market

104 ACORN Drive, Chestertown, MD
Townhouse

$275K

104 ACORN Drive

Chestertown, MD

3 bd3 ba1,900
234 N COLLEGE Avenue, Chestertown, MD
Single Family

$79K

234 N COLLEGE Avenue

Chestertown, MD

2 bd1 ba1,296
6746 QUAKER NECK Road, Chestertown, MD
Single Family

$339K

6746 QUAKER NECK Road

Chestertown, MD

5 bd3 ba3,371
123 TRAFFORD Drive, Chestertown, MD
Single Family

$370K

123 TRAFFORD Drive

Chestertown, MD

4 bd3 ba2,504
106 HARLAN Loop, Chestertown, MD
Single Family

$425K

106 HARLAN Loop

Chestertown, MD

4 bd3 ba3,165
23043 BAY SHORE Spur, Chestertown, MD
Single Family

$385K

23043 BAY SHORE Spur

Chestertown, MD

4 bd3 ba2,630
105 HIGH Street, Chestertown, MD
Single Family

$1.2M

105 HIGH Street

Chestertown, MD

5 bd5 ba3,243
212 WASHINGTON Avenue, Chestertown, MD
Single Family

$675K

212 WASHINGTON Avenue

Chestertown, MD

5 bd3 ba2,838
Browse

Homes for Sale in Chestertown

Every active listing in Chestertown, browsable page by page.

24607 CHESTERTOWN Road - Single Family for sale in Chestertown, MD
Single Family

$365K

24607 CHESTERTOWN Road

Chestertown, MD

3 bd3 ba2,294
8901 S BAYVIEW Drive - Single Family for sale in Chestertown, MD
Single Family

$525K

8901 S BAYVIEW Drive

Chestertown, MD

3 bd3 ba1,833
21338 VIRGINIA Avenue - Single Family for sale in Chestertown, MD
Single Family

$400K

21338 VIRGINIA Avenue

Chestertown, MD

2 bd2 ba1,000
10 CEDAR CHASE Court - Single Family for sale in Chestertown, MD
Single Family

$495K

10 CEDAR CHASE Court

Chestertown, MD

3 bd3 ba1,656
106 HARLAN Loop - Single Family for sale in Chestertown, MD
Single Family

$425K

106 HARLAN Loop

Chestertown, MD

4 bd3 ba3,165
212 WASHINGTON Avenue - Single Family for sale in Chestertown, MD
Single Family

$675K

212 WASHINGTON Avenue

Chestertown, MD

5 bd3 ba2,838
8820 CUMBERLAND Street - Single Family for sale in Chestertown, MD
Single Family

$313K

8820 CUMBERLAND Street

Chestertown, MD

3 bd2 ba1,080
896 WASHINGTON Avenue - Commercial for sale in Chestertown, MD
Commercial

$325K

896 WASHINGTON Avenue

Chestertown, MD

0 bd0 ba0
105 N WATER Street - Condo for sale in Chestertown, MD
Condo

$459K

105 N WATER Street

Chestertown, MD

2 bd2 ba1,098
329 UNION CHURCH Road - Single Family for sale in Chestertown, MD
Single Family

$550K

329 UNION CHURCH Road

Chestertown, MD

4 bd3 ba2,464
6324 QUAKER NECK Road - Single Family for sale in Chestertown, MD
Single Family

$2.9M

6324 QUAKER NECK Road

Chestertown, MD

5 bd4 ba5,938
8732 ELM Road - Single Family for sale in Chestertown, MD
Single Family

$289K

8732 ELM Road

Chestertown, MD

3 bd2 ba1,056
104 LINCOLN Drive - Single Family for sale in Chestertown, MD
Single Family

$275K

104 LINCOLN Drive

Chestertown, MD

3 bd1 ba960
TOWHEE Road - Land for sale in Chestertown, MD
Land

$40K

TOWHEE Road

Chestertown, MD

0 bd0 ba0
7415 WILKINS Lane - Single Family for sale in Chestertown, MD
Single Family

$222K

7415 WILKINS Lane

Chestertown, MD

3 bd1 ba936
300 and 302 S MILL Street - Land for sale in Chestertown, MD
Land

$1.2M

300 and 302 S MILL Street

Chestertown, MD

0 bd0 ba0
300 and 302 S MILL Street - Single Family for sale in Chestertown, MD
Single Family

$1.2M

300 and 302 S MILL Street

Chestertown, MD

2 bd1 ba806
8184 ROCK HALL Road - Land for sale in Chestertown, MD
Land

$38.2M

8184 ROCK HALL Road

Chestertown, MD

4 bd2 ba2,330
101 S COLLEGE Avenue - Single Family for sale in Chestertown, MD
Single Family

$359K

101 S COLLEGE Avenue

Chestertown, MD

2 bd2 ba1,036
124 WILTON Road - Single Family for sale in Chestertown, MD
Single Family

$295K

124 WILTON Road

Chestertown, MD

3 bd1 ba1,056
123 TRAFFORD Drive - Single Family for sale in Chestertown, MD
Single Family

$370K

123 TRAFFORD Drive

Chestertown, MD

4 bd3 ba2,504
10540 TONOPAH Road - Mobile Home for sale in Chestertown, MD
Mobile Home

$267K

10540 TONOPAH Road

Chestertown, MD

3 bd2 ba1,404
8630 ELM Road - Single Family for sale in Chestertown, MD
Single Family

$400K

8630 ELM Road

Chestertown, MD

5 bd3 ba1,936
CANNON Street - Land for sale in Chestertown, MD
Land

$196K

CANNON Street

Chestertown, MD

0 bd0 ba0
CANNON Street - Land for sale in Chestertown, MD
Land

$281K

CANNON Street

Chestertown, MD

0 bd0 ba0
620 CANNON Street - Land for sale in Chestertown, MD
Land

$85K

620 CANNON Street

Chestertown, MD

0 bd0 ba0
201 N LYNCHBURG Street - Other for sale in Chestertown, MD
Other

$500K

201 N LYNCHBURG Street

Chestertown, MD

0 bd0 ba0
201 N LYNCHBURG Street lot: 4, 5, 6 & 7 - Land for sale in Chestertown, MD
Land

$300K

201 N LYNCHBURG Street lot: 4, 5, 6 & 7

Chestertown, MD

0 bd0 ba0
233 MERGANSER DR - Single Family for sale in Chestertown, MD
Single Family

$60K

233 MERGANSER DR

Chestertown, MD

0 bd0 ba0
305 ROOSEVELT Drive - Land for sale in Chestertown, MD
Land

$45K

305 ROOSEVELT Drive

Chestertown, MD

0 bd0 ba0
896 WASHINGTON Avenue - Single Family for sale in Chestertown, MD
Single Family

$325K

896 WASHINGTON Avenue

Chestertown, MD

3 bd1 ba1,000
234 N COLLEGE Avenue - Single Family for sale in Chestertown, MD
Single Family

$79K

234 N COLLEGE Avenue

Chestertown, MD

2 bd1 ba1,296
104 ACORN Drive - Townhouse for sale in Chestertown, MD
Townhouse

$275K

104 ACORN Drive

Chestertown, MD

3 bd3 ba1,900
25416 COMMERCE Lane - Other for sale in Chestertown, MD
Other

$1.1M

25416 COMMERCE Lane

Chestertown, MD

0 bd0 ba0
8796 MARYLAND Parkway - Single Family for sale in Chestertown, MD
Single Family

$1.5M

8796 MARYLAND Parkway

Chestertown, MD

9 bd7 ba4,776
8796 MARYLAND Parkway - Other for sale in Chestertown, MD
Other

$1.5M

8796 MARYLAND Parkway

Chestertown, MD

0 bd0 ba0
8886 GEORGETOWN Road - Land for sale in Chestertown, MD
Land

$70K

8886 GEORGETOWN Road

Chestertown, MD

0 bd0 ba0
956 WASHINGTON Avenue - Single Family for sale in Chestertown, MD
Single Family

$275K

956 WASHINGTON Avenue

Chestertown, MD

3 bd1 ba1,248
MAP 36 PARCEL 80 WATERTOWER Road - Land for sale in Chestertown, MD
Land

$55K

MAP 36 PARCEL 80 WATERTOWER Road

Chestertown, MD

0 bd0 ba0
SANDY BOTTOM Road - Land for sale in Chestertown, MD
Land

$49K

SANDY BOTTOM Road

Chestertown, MD

0 bd0 ba0
109 2ND Street - Land for sale in Chestertown, MD
Land

$125K

109 2ND Street

Chestertown, MD

0 bd0 ba0
106 QUEEN Street S - Single Family for sale in Chestertown, MD
Single Family

$829K

106 QUEEN Street S

Chestertown, MD

3 bd4 ba2,472
ROUND TOP ROAD - Land for sale in Chestertown, MD
Land

$200K

ROUND TOP ROAD

Chestertown, MD

0 bd0 ba0
201 N LYNCHBURG Street - Land for sale in Chestertown, MD
Land

$750K

201 N LYNCHBURG Street

Chestertown, MD

0 bd0 ba0
201 N LYNCHBURG Street - Single Family for sale in Chestertown, MD
Single Family

$750K

201 N LYNCHBURG Street

Chestertown, MD

0 bd2 ba2,045
201 N LYNCHBURG Street - Other for sale in Chestertown, MD
Other

$750K

201 N LYNCHBURG Street

Chestertown, MD

0 bd0 ba0
22681 WOOD YARD Lane - Land for sale in Chestertown, MD
Land

$15K

22681 WOOD YARD Lane

Chestertown, MD

0 bd0 ba0
6746 QUAKER Road - Other for sale in Chestertown, MD
Other

$339K

6746 QUAKER Road

Chestertown, MD

0 bd0 ba0
6746 QUAKER NECK Road - Single Family for sale in Chestertown, MD
Single Family

$339K

6746 QUAKER NECK Road

Chestertown, MD

5 bd3 ba3,371
GEORGETOWN Road - Land for sale in Chestertown, MD
Land

$90K

GEORGETOWN Road

Chestertown, MD

0 bd0 ba0

Showing 1–50 of 63 · Page 1 of 2

Beyond the listings

Continue exploring Chestertown

Turn the listings into a short list with a clearer read on the Chestertown market, its neighborhoods, and the home features that matter to you.

Refine Chestertown searchAll Maryland homes
Local market guide

Chestertown Housing Market

Browse 63 active listings in Chestertown, Maryland. The average list price for this active inventory is $1,052,248. Compare the price and property details reported in each listing.

Average list price $1,052,248 · Range $5,000–$38,200,000 · 63 active listings

Buyer questions

Frequently Asked Questions

How many active listings are available in Chestertown, Maryland?

The current inventory contains 63 active listings in Chestertown, MD.

What is the average list price in Chestertown, Maryland?

The average list price among current active listings in Chestertown, MD is $1,052,248. Current list prices range from $5,000 to $38,200,000.

What is the average days on market for active listings in Chestertown?

Current active listings in Chestertown, MD report an average of 227 days on market.

What is the average list price per square foot in Chestertown?

The average list price per square foot among current active listings in Chestertown, MD is $839.

Shape your search

Browse Chestertown by home feature

Homes with Solar FeaturesHomes with EV ChargersHomes with PoolsWaterfront HomesHomes with ViewsHomes with Recorded Price ReductionsListings Added to PropertySimple in the Past 7 DaysHomes Built Since 2024

Nationwide collections

Explore by listing details

Waterfront ListingsListings Marked WaterfrontListings in Mountain StatesSix-State CollectionMulti-Family & Commercial ListingsListings by Property TypeListings with 3+ BedroomsThree or More BedroomsListings Priced at $1.5M+Listings by Asking PriceListings Built Since 2015Listings by Year Built

Ready to make the list yours?

Use the full search to set your price, beds, property type, and must-have features for Chestertown.

Search Chestertown homes