Is a car needed in Chestertown, MD?

As of early 2026, 85% of users say car is needed

Does Chestertown, MD show holiday spirit?

As of early 2026, 84% of users say there's holiday spirit

Is Chestertown, MD dog-friendly?

As of early 2026, 83% of users say it's dog friendly

Would people walk alone at night in Chestertown, MD?

As of early 2026, 77% of users say people would walk alone at night

Is parking easy in Chestertown, MD?

As of early 2026, 77% of users say parking is easy

Are yards well-kept in Chestertown, MD?

As of early 2026, 76% of users say yards are well-kept

Is Chestertown, MD quiet?

As of early 2026, 74% of users say it's quiet

Are neighbors friendly in Chestertown, MD?

As of early 2026, 61% of users say neighbors are friendly

Is there wildlife in Chestertown, MD?

As of early 2026, 57% of users say there's wildlife

Is Chestertown, MD walkable to restaurants?

As of early 2026, 56% of users say it's walkable to restaurants

Does Chestertown, MD have sidewalks?

As of early 2026, 54% of users say there are sidewalks

Do kids play outside in Chestertown, MD?

As of early 2026, 49% of users say kids play outside

Is Chestertown, MD walkable to grocery stores?

As of early 2026, 46% of users say it's walkable to grocery stores

Are the streets well-lit in Chestertown, MD?

As of early 2026, 44% of users say streets are well-lit

Are there community events in Chestertown, MD?

As of early 2026, 41% of users say there are community events

Do residents of Chestertown, MD plan to stay at least 5 years?

As of early 2026, 38% of users say they plan to stay for at least 5 years

OFF MARKET

501 High St
Chestertown, MD 21620

1 Bed
1 Bath
809 sqft

$347,600

Trulia Estimate

as of Jun 6, 2026

Est. Refi. Payment $2,029/mo*

Refinance Your Home

$347,600

Trulia Estimate

as of Jun 6, 2026

Est. Refi. Payment $2,029/mo*

Refinance Your Home

1 Bed

1 Bath

809 sqft

Local Information

-- mins to

Commute Destination

Description

This condo is located at 501 High St, Chestertown, MD. 501 High St is in Chestertown, MD and in ZIP code 21620. This property has 1 bedroom, 1 bathroom and approximately 809 sqft of floor space. This property has a lot size of 1481 sqft and was built in 1900.

This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking

No Info

Outdoor

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 501 High St

Interior Features
Heating & Cooling Heating: Baseboard, ElectricAir ConditioningHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 2Floors: Other
Interior Details Types of Rooms: Breakfast Nook
Appliances & Utilities DryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: OtherExterior: Vinyl

Property Information
Year Built Year Built: 1900
Property Type / Style Property Type: CondoArchitecture: Colonial

Community
Units in Building: 1

Lot Information
Lot Area: 1481 sqft

Price History for 501 High St

Date	Price	Event	Source
06/02/2023	$300,000	Sold	N/A
Recording Date 06/02/2023 Contract Date 05/24/2023 County Transfer Tax $15 Total Transfer Tax $30
04/03/2020	$835	ListingRemoved	Agent Provided

03/25/2020	$835	Listed For Rent	Agent Provided

06/29/2017	$775	ListingRemoved	Agent Provided

06/06/2017	$775	Listed For Rent	Agent Provided

08/11/2016	$230,000	Sold	N/A
Recording Date 08/11/2016 Contract Date 08/11/2016 County Transfer Tax $1,150 Total Transfer Tax N/A
04/20/2016	$239,000	Listed For Sale	Agent Provided

01/01/2015	$220,000	Sold	Long & Foster Broker Feed #MDKE100352_100
Recording Date 01/01/2015 County Transfer Tax N/A Total Transfer Tax N/A
05/30/2014	$700	ListingRemoved	Agent Provided

10/25/2013	$700	PriceChange	Agent Provided
Price Change $50 (-7%)
10/11/2013	$750	Listed For Rent	Agent Provided

04/28/2012	$700	ListingRemoved	Agent Provided

04/16/2012	$700	Listed For Rent	Agent Provided

08/31/2007	$220,000	Sold	N/A
Recording Date 08/31/2007 County Transfer Tax N/A Total Transfer Tax N/A
05/01/2001	$144,000	Sold	N/A
Recording Date 05/01/2001 County Transfer Tax N/A Total Transfer Tax N/A
01/23/1998	$37,500	Sold	N/A
Recording Date 01/23/1998 County Transfer Tax N/A Total Transfer Tax N/A
01/20/1995	$28,000	Sold	N/A
Recording Date 01/20/1995 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Chestertown

Last updated April 2026

Avg. sale price

—

Sale-to-List Price

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Price per sq ft

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Available listings

11MoM

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Property Tax and Assessment

Year	2025
Tax
Assessment	$279,133

Home facts updated by county records

Comparable Sales for 501 High St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
117 N Water St #3B, Chestertown, MD	0.46	Condo	$285,000	08/08/25	1	1	652
118 Little Harbor Way #201, Chestertown, MD	0.88	Condo	$665,000	04/09/26	2	2.5	1,500
118 Little Harbor Way #201, Chestertown, MD	0.85	Condo	$665,000	03/30/26	2	2.5	1,600
308A Landing Ln, Chestertown, MD	0.83	Condo	$782,500	06/18/25		-	2,204

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $642,900
7 bd
3,114 sqft
425 High St,
Chestertown, MD 21620
Select Land & Homes, LLC
OFF MARKET
Est. $411,200
2 bd
2.5 ba
1,356 sqft
101 S Kent St,
Chestertown, MD 21620
Washington Fine Properties
FOR SALE
$798,000
3 bd
4.5 ba
3,047 sqft
407 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
DEC 19, 2025
$361,500
4 bd
1,728 sqft
517 High St,
Chestertown, MD 21620
L. C. Parker Real Estate
OFF MARKET
Est. $353,800
2 bd
2 ba
1,080 sqft
420 Cannon St,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
OFF MARKET
Est. $451,500
2 bd
2.5 ba
1,464 sqft
502 Cannon St,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
NOV 5, 2025
$695,000
3 bd
3.5 ba
2,492 sqft
110 S Mill St,
Chestertown, MD 21620
Gunther-McClary Real Estate
OFF MARKET
Est. $151,300
3 bd
3 ba
2,240 sqft
508 Cannon St,
Chestertown, MD 21620
Coldwell Banker Realty
OFF MARKET
Est. $783,100
4 bd
3.5 ba
2,683 sqft
112 S Mill St,
Chestertown, MD 21620
Gunther-McClary Real Estate
OFF MARKET
Est. $304,300
3 bd
1.5 ba
1,584 sqft
410 Cannon St,
Chestertown, MD 21620
Cross Street Realtors LLC
FOR SALE
$450,000
2 bd
3 ba
1,518 sqft
522 High St,
Chestertown, MD 21620
Benson & Mangold, LLC
OFF MARKET
Est. $494,000
2 bd
2.5 ba
1,476 sqft
101 S Mill St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company

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Additional Cost

Assigned Schools

These are the assigned schools for 501 High St.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chestertown

At least 34 Trulia users voted on each feature.

85 % Say car is needed
84 % Say there's holiday spirit
83 % Say it's dog friendly
77 % Say people would walk alone at night
77 % Say parking is easy
76 % Say yards are well-kept
74 % Say it's quiet
61 % Say neighbors are friendly
57 % Say there's wildlife
56 % Say it's walkable to restaurants
54 % Say there are sidewalks
49 % Say kids play outside
46 % Say it's walkable to grocery stores
44 % Say streets are well-lit
41 % Say there are community events
38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.

Trulia User
Visitor
3y ago
"Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
1
Flag
Trulia User
Visitor
5y ago
"Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
1
Flag
Trulia User
Prev. Resident
5y ago
"I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
0
Flag
Kesha C.
Resident
6y ago
"Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
0
Flag
Tracy W.
Resident
6y ago
"The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
0
Flag
Rancraw
Resident
7y ago
"This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
9
Flag
Acaldwell1297
Resident
7y ago
"I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
1
Flag
Guillermo A.
11y ago
"Good Community, friendly people, good services. "
0
Flag
Nancy M.
12y ago
"People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
5
Flag
asso
12y ago
"Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
0
Flag
Dafoster
12y ago
"Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
5
Flag

LGBTQ Local Legal Protections

Apartments for Rent

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Contact for price
1-2 bd
1-2 ba
501 E Campus Ave #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
150 Flatland Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
415 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
101 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
200 Morgnec Rd #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
103 Hawkins Dr #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
200 Clipper Way #776f18ccb,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
160 Flatland Rd #f320a52c6,
Chestertown, MD 21620
Contact for price
1-2 bd
1-2 ba
402 Morgnec Rd #f320a52c6,
Chestertown, MD 21620
APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
331 Calvert St #321,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
104 Maple Ave #6,
Chestertown, MD 21620
See more homes for rent in
Chestertown
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Explore by feature

APPLY INSTANTLY
PET FRIENDLY
$1,500/mo
1 bd
1 ba
500 sqft
331 Calvert St #321,
Chestertown, MD 21620
NEW - 2 DAYS AGO
$2,500/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$1,700/mo
2 bd
1 ba
1,100 sqft
27318 Morgnec Rd #B,
Chestertown, MD 21620
$2,600/mo
3 bd
2.5 ba
2,612 sqft
104 Cedar St,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620

Homes for sale near 501 High St

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$350,000
1 bd
1 ba
850 sqft
117 N Water St #2B,
Chestertown, MD 21620
TTR Sotheby's International Realty
$200,000
1 bd
1 ba
700 sqft
117 N Water St #1B,
Chestertown, MD 21620
TTR Sotheby's International Realty
$375,000
2 bd
1 ba
787 sqft
117 N Water St #2A,
Chestertown, MD 21620
TTR Sotheby's International Realty
$685,000
3 bd
3 ba
3,000 sqft
117 N Water St #1A,
Chestertown, MD 21620
TTR Sotheby's International Realty
$1,600,000
7 bd
5 ba
5,400 sqft
117 N Water St #1A-1B-2B,
Chestertown, MD 21620
TTR Sotheby's International Realty
NEW CONSTRUCTION
$765,900
3 bd
2.5 ba
1,964 sqft
37 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
NEW CONSTRUCTION
$753,500
3 bd
2.5 ba
1,964 sqft
36 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
NEW CONSTRUCTION
$786,900
3 bd
2.5 ba
1,964 sqft
35 Landing Ln,
Chestertown, MD 21620
Gunther-McClary Real Estate
NEW CONSTRUCTION
$839,500
3 bd
2.5 ba
1,964 sqft
102 Little Harbor Way,
Chestertown, MD 21620
Gunther-McClary Real Estate
NEW CONSTRUCTION
$849,900
3 bd
2.5 ba
1,980 sqft
104 Little Harbor Way,
Chestertown, MD 21620
Gunther-McClary Real Estate
See more homes for sale in
Chestertown
Take a look

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Off Market Homes Near 501 High St

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SOLD
JUN 5, 2026
$175,000
3 bd
1 ba
1,296 sqft
113 Pear Tree Point Rd,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
JUN 4, 2026
$290,000
2 bd
2.5 ba
1,864 sqft
115 Acorn Dr,
Chestertown, MD 21620
Chesapeake Real Estate Associates, LLC
SOLD
MAY 29, 2026
$430,000
3 bd
2 ba
1,588 sqft
201 Birch Run Rd,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
MAY 27, 2026
$300,000
3 bd
1 ba
1,408 sqft
154 Longfellow Dr,
Chestertown, MD 21620
Cross Street Realtors LLC
SOLD
MAY 26, 2026
$355,000
6 bd
3,664 sqft
349 & 351 High St,
Chestertown, MD 21620
Coldwell Banker Chesapeake Real Estate Company
SOLD
MAY 26, 2026
$264,900
3 bd
1.5 ba
1,280 sqft
109 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
SOLD
MAY 22, 2026
$296,500
2 bd
2.5 ba
1,867 sqft
108 Oak Leaf Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
SOLD
MAY 19, 2026
$376,000
3 bd
2 ba
1,432 sqft
136 Hilltop Dr,
Chestertown, MD 21620
Northrop Realty
SOLD
MAY 18, 2026
$259,900
3 bd
1.5 ba
1,200 sqft
107 Metcalf Rd,
Chestertown, MD 21620
Real Broker, LLC
SOLD
MAY 14, 2026
$278,500
3 bd
1 ba
107 Longfellow Dr,
Chestertown, MD 21620
Doug Ashley Realtors, LLC
See more homes for sale in
Chestertown
Take a look

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Homes for rent near 501 High St

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NEW - 2 DAYS AGO
$2,500/mo
Total price
4 bd
2 ba
1,500 sqft
1010 Twin Ct,
Chestertown, MD 21620
$2,600/mo
3 bd
2.5 ba
2,612 sqft
104 Cedar St,
Chestertown, MD 21620
PET FRIENDLY
$2,050/mo
2 bd
2 ba
900 sqft
104 Maple Ave #6,
Chestertown, MD 21620
See more homes for rent in
Chestertown
Take a look

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501 High St, Chestertown, MD 21620 is a 1 bedroom, 1 bathroom, 809 sqft condo built in 1900. This property is not currently available for sale. 501 High St was last sold on Jun 2, 2023 for $300,000. The current Trulia Estimate for 501 High St is $347,600.

501 High St
Chestertown, MD 21620

$347,600

$347,600

Local Information