501 High St, Chestertown, MD 21620
OFF MARKET

$343,200

Trulia Estimate
  • 1 Bed
  • 1 Bath
  • 809 sqft

501 High St, Chestertown, MD 21620

Est. Refi. Payment $2,036/mo*
Refinance Your Home
Currently Off Market - Sold Jun 2, 2023 for $300,000

Home Value

Trulia Estimate
$343K
Since last month
Decreased$8K (-2.3%)
Since last year
Increased$10K (+2.9%)
Since last sale
Increased$43K (+14.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +49% in the last 10 years
MonthEstimated value
2026
August 2026$343K
July 2026$351K
June 2026$348K
May 2026$348K
April 2026$339K
March 2026$336K
February 2026$336K
January 2026$344K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
118 Little Harbor Way #201, Chestertown, MD
0.88
Condo
$665,000
04/09/26
2
2.5
1,500
118 Little Harbor Way #202, Chestertown, MD
0.85
Condo
$660,000
06/05/26
3
2
1,600
118 Little Harbor Way #201, Chestertown, MD
0.85
Condo
$665,000
03/30/26
2
2.5
1,600
316 Landing Ln, Chestertown, MD
0.77
Condo
$820,000
06/17/26
-
-

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
425 High St, Chestertown, MD 21620
0.02
$633,200
7
-
3,114
Off Market
101 S Kent St, Chestertown, MD 21620
0.03
$404,700
2
2.5
1,356
Off Market
517 High St, Chestertown, MD 21620
0.03
$361,500
4
-
1,728
Recently Sold
420 Cannon St, Chestertown, MD 21620
0.08
$351,200
2
2
1,080
Off Market
110 S Mill St, Chestertown, MD 21620
0.11
$695,000
3
3.5
2,492
Recently Sold
508 Cannon St, Chestertown, MD 21620
0.07
$150,300
3
3
2,240
Off Market
112 S Mill St, Chestertown, MD 21620
0.11
$774,300
4
3.5
2,683
Off Market
410 Cannon St, Chestertown, MD 21620
0.11
$305,800
3
1.5
1,584
Off Market
529 Cannon St, Chestertown, MD 21620
0.09
$415,400
3
2
1,288
Off Market
349 & 351 High St, Chestertown, MD 21620
0.14
$355,000
6
-
3,664
Recently Sold
201 Radcliffe Dr, Chestertown, MD 21620
0.13
$795,000
4
2.5
2,736
Recently Sold
204 N Mill St, Chestertown, MD 21620
0.14
$423,300
5
3.5
2,890
Off Market

Local Information

  • Map ViewExplore the area around 501 High St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Condo
Year Built
1900
Living Area
809 sqft
Price/Sqft
$424

About this House

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.
501 High St, Chestertown, MD 21620 is a 1 bedroom, 1 bathroom, 809 sqft condo built in 1900. It last sold for $300,000 on Jun 2, 2023. More recently, it was listed as a rental in March 2020 with an asking price of $835 per month. That rental listing was removed on April 3, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $343,200, with a rent estimate of $1,303/month.

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 and Tax history

DateEventPrice
Jun 2, 2023
Source: N/A
Sold
$300,000
Apr 3, 2020
Source: Agent Provided
ListingRemoved
$835
Mar 25, 2020
Source: Agent Provided
Listed For Rent
$835
Jun 29, 2017
Source: Agent Provided
ListingRemoved
$775
Jun 6, 2017
Source: Agent Provided
Listed For Rent
$775

Market trends in Chestertown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
5MoM

Around this home

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
    "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
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "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.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "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
    "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
    "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.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "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
    "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

Frequently asked questions about 501 High St

  • What is 501 High St estimated to be worth?
    Trulia's estimated value for 501 High St in Chestertown, MD is $343,200.
  • What is the price history for 501 High St?
    501 High St in Chestertown, MD last sold for $300,000 in June 2023.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, MD as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.
  • Does 501 High St have laundry facilities?
    Yes, 501 High St in Chestertown, MD has in-unit laundry.

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