532 High St, Chestertown, MD 21620
Property image
Property image
OFF MARKET

$327,800

Trulia Estimate
  • Studio
  • 2 Baths
  • 1,186 sqft

532 High St, Chestertown, MD 21620

Est. Refi. Payment $1,954/mo*
Refinance Your Home
Currently Off Market - Sold Jun 15, 2023 for $295,000

Home Value

Trulia Estimate
$328K
Since last month
Decreased$1K (-0.4%)
Since last year
Increased$3K (+0.9%)
Since last sale
Increased$33K (+11.1%)
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 +90% in the last 10 years
MonthEstimated value
2026
August 2026$328K
August 2026$327K
July 2026$329K
June 2026$333K
May 2026$327K
April 2026$325K
March 2026$321K
February 2026$318K
January 2026$321K
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
141 Prospect St, Chestertown, MD
0.17
Single-Family Home
$120,000
02/27/26
4
1.5
1,156
139 Prospect St, Chestertown, MD
0.17
Single-Family Home
$195,000
07/31/26
3
1
1,200
109 S College Ave, Chestertown, MD
0.07
Single-Family Home
$410,000
06/26/26
3
2.5
1,216
524 Cannon St, Chestertown, MD
0.12
Single-Family Home
$230,000
02/02/26
2
1
928
217 Philosophers Ter, Chestertown, MD
0.40
Single-Family Home
$370,000
05/01/26
3
1.5
1,404
144 Prospect St, Chestertown, MD
0.20
Single-Family Home
$165,000
07/07/26
2
1.5
1,082
100 Prospect St, Chestertown, MD
0.13
Single-Family Home
$215,000
07/21/26
3
1
1,373
349 High St, Chestertown, MD
0.24
Single-Family Home
$355,000
06/03/26
3
3,664
101 S Mill St, Chestertown, MD
0.22
Single-Family Home
$500,000
09/01/26
2
2.5
1,476
405 Cannon St, Chestertown, MD
0.18
Single-Family Home
$325,000
05/05/26
2
1
462

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
409 Calvert St, Chestertown, MD 21620
0.05
$145,000
3
1.5
1,192
For Sale
614 High St, Chestertown, MD 21620
0.07
$241,300
2
1.5
1,064
Off Market
423 Calvert St, Chestertown, MD 21620
0.08
$190,000
3
1.5
1,136
Recently Sold
612 High St, Chestertown, MD 21620
0.07
$230,400
2
1.5
1,064
Off Market
234 N College Ave, Chestertown, MD 21620
0.10
$85,000
2
1
1,296
For Sale
545 High St #545, Chestertown, MD 21620
0.05
$263,800
2
1.5
929
Off Market
101 S College Ave, Chestertown, MD 21620
0.05
$369,000
2
1.5
1,036
For Sale
201 N Lynchburg St, Chestertown, MD 21620
0.11
$750,000
-
-
-
For Sale
201 N Lynchburg St #&-7, Chestertown, MD 21620
0.11
$300,000
-
-
-
For Sale
211 N Lynchburg St, Chestertown, MD 21620
0.12
-
-
-
-
Off Market
517 High St, Chestertown, MD 21620
0.07
$361,500
4
-
1,728
Recently Sold
109 S College Ave, Chestertown, MD 21620
0.07
$410,000
3
2.5
1,216
Recently Sold

Local Information

  • Map ViewExplore the area around 532 High St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1960
Living Area
1,186 sqft
Price/Sqft
$276
Parking
Garage

About this House

This single-family home is located at 532 High St, Chestertown, MD. 532 High St is in Chestertown, MD and in ZIP code 21620. This property has 2 bathrooms and approximately 1,186 sqft of floor space. This property has a lot size of 7530 sqft and was built in 1960.
532 High St, Chestertown, MD 21620 is a studio, 2 bathroom, 1,186 sqft single-family home built in 1960. It last sold for $295,000 on Jun 15, 2023. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $327,800, with a rent estimate of $2,112/month.

Home Details for 532 High St

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: BaseboardHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1.5
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1960
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 7530 sqft

Price and Tax history

DateEventPrice
Jun 15, 2023
Source: Bright MLS #MDKE2002670
Sold
$295,000
May 18, 2023
Source: Bright MLS #MDKE2002670
Pending
$327,900
May 10, 2023
Source: Bright MLS #MDKE2002670
Listed For Sale
$327,900

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 532 High St

  • What is 532 High St estimated to be worth?
    Trulia's estimated value for 532 High St in Chestertown, MD is $327,800.
  • What is the price history for 532 High St?
    532 High St in Chestertown, MD last sold for $295,000 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.
  • How big is the lot at 532 High St?
    The lot at 532 High St in Chestertown, MD is about 0.17 acres (7,530 sq ft).
  • Does 532 High St have a garage?
    Yes, 532 High St in Chestertown, MD has a garage.

Apartments for Rent

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Off Market Homes Near 532 High St

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