SOLD NOV 24, 2025

Off market nov 2025 for $359K

$414,157

Est. refi paymentEst. refi $2,703/mo

•

1,851

sq ft

221 Old Bridge Rd, Chestertown, MD 21620

About this home

Charming American Foursquare on a half-acre corner lot, just one block from the Chester River on the Queen Anne's County side of Historic Chestertown. The home features a welcoming front porch, 3 bedrooms, 2 full baths, an office on the main level, hardwood floors, and many original details. Recent updates include a new upstairs bathroom, new electric panel, and a 2-year-old roof. The walk-up attic and large shed/garage provide ample storage. Walk over the bridge to downtown and the Farmer's Market. Would make a great primary or second home.

Single-familyProperty Type

1924Year Built

0.51 acresLot Size

$224Est. Price/Sq.Ft.

5 spacesParking

Listed by Courtney Chipouras • TTR Sotheby's International Realty

•410-673-3344 (broker)

Bought with Terri Kulp • Coldwell Banker Chesapeake Real Estate Company

•410-778-0330 (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDQA2014888

Redfin Estimate

$414,157

$54K since sold in November 2025$9,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.9% higher than the average sale price ($377K) of 6 comparable homes.

SOLD JUL 22, 2026
$365,000
A
3 beds2 baths1,934 sq ft
521 N Kent St, Chestertown, MD 21620
SOLD AUG 14, 2026
$320,000
B
3 beds2 baths1,820 sq ft
640 Main St, Church Hill, MD 21623
SOLD SEP 22, 2026
$349,000
C
3 beds2 baths1,792 sq ft
123 Heath Rd, Chestertown, MD 21620
SOLD APR 17, 2026
$480,000
D
3 beds2 baths1,734 sq ft
104 Garland Ave, Chestertown, MD 21620
SOLD MAY 29, 2026
$430,000
E
3 beds2 baths1,588 sq ft
201 Birch Run Rd, Chestertown, MD 21620
SOLD AUG 14, 2026
$318,000
F
3 beds2 baths1,397 sq ft
109 Cedar St, Chestertown, MD 21620

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,604/mo

Redfin rental estimate

List your home for rent

Market trends in 21620, MD

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.4%

+0.3% MoM

Median sale price

$355K

$7K MoM

Avg. days on market

48d

0 days MoM

Recently sold homes

0 MoM

New listings for sale

OPEN SAT, 11AM TO 1PM
$489,000
2 beds2 baths1,098 sq ft
105 N Water St #3, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$499,999
4 beds3.5 baths3,506 sq ft
331 Devon Dr, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$495,000
3 beds2.5 baths1,656 sq ft
10 Cedar Chase Ct, Chestertown, MD 21620
(410) 778-3779
$2,895,000
5 beds3.5 baths5,938 sq ft
6324 Quaker Neck Rd, Chestertown, MD 21620
(410) 778-3779
3D WALKTHROUGH
$329,900
2 beds2 baths1,440 sq ft
22974 Bay Shore Rd, Chestertown, MD 21620
(410) 822-6665
See all

Provided by Redfin

Redfin agents who toured

Updated historic charmer located close the Chester River and downtown Chestertown. Beautiful flooring throughout; nice space in the 2nd level bedrooms and walk up attached; detached 2 car garage parking and deep, private backyard.
11 months ago• May not reflect the current state of the home
Barbara McCaffrey
Redfin Premier agent

Sale history for 221 Old Bridge Rd

Date

Event

Price

BRIGHT MLS #MDQA2014888

Nov 24, 2025

Sold

$359,900

$194/sq ft

Nov 11, 2025

Pending

—

Oct 29, 2025

Contingent

—

Oct 3, 2025

Listed

$369,900

$200/sq ft

Sep 17, 2025

Coming Soon

$369,900

$200/sq ft

Public Records

Aug 8, 2014

Sold

$199,750

$108/sq ft

MRIS #QA8159743

Aug 6, 2014

Delisted

—

Aug 6, 2014

Sold

$199,750

$108/sq ft

May 13, 2014

Pending

—

Apr 14, 2014

Price Changed

$108/sq ft

Feb 14, 2014

Price Changed

$123/sq ft

Dec 2, 2013

Relisted

—

Nov 13, 2013

Pending

—

Aug 15, 2013

Listed

$128/sq ft

+20

BRIGHT MLS #1003681248

Aug 6, 2014

Sold

$199,750

$108/sq ft

May 7, 2014

Listing Removed

—

Aug 15, 2013

Listed

$199,900

$108/sq ft

+20

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$2,606 (+4.9%)

2024

$2,485 (+4.9%)

$81,700 + $203,000

$284,700

2023

$2,368 (+4.9%)

2022

$2,257 (+3.2%)

2021

$2,187 (+5.1%)

$81,700 + $162,600

$244,300

2020

$2,081 (+5.1%)

2019

$1,980

2018

$1,980

$71,700 + $128,500

$200,200

2017

$1,980 (−0.5%)

$71,700 + $128,500

$200,200

2016

$1,990 (+8.6%)

$72,900 + $128,400

$201,300

2015

$1,832 (+3.9%)

$72,900 + $128,400

$201,300

2014

$1,763 (+4.1%)

$97,800 + $107,600

$205,400

2013

$1,693 (+6.1%)

2012

$1,596 (+9.1%)

2011

$1,463 (+5.3%)

2010

$1,389 (+8.0%)

2009

$1,286

Tax history for 221 Old Bridge Rd

Year

Property tax

Land + Additions

Assessment*

2025

$2,606 (+4.9%)

2024

$2,485 (+4.9%)

$81,700 + $203,000

$284,700

2023

$2,368 (+4.9%)

2022

$2,257 (+3.2%)

2021

$2,187 (+5.1%)

$81,700 + $162,600

$244,300

2020

$2,081 (+5.1%)

2019

$1,980

2018

$1,980

$71,700 + $128,500

$200,200

2017

$1,980 (−0.5%)

$71,700 + $128,500

$200,200

2016

$1,990 (+8.6%)

$72,900 + $128,400

$201,300

2015

$1,832 (+3.9%)

$72,900 + $128,400

$201,300

2014

$1,763 (+4.1%)

$97,800 + $107,600

$205,400

2013

$1,693 (+6.1%)

2012

$1,596 (+9.1%)

2011

$1,463 (+5.3%)

2010

$1,389 (+8.0%)

2009

$1,286

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning
Permits

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.51 Acres

Year renovated

—

Sq. Ft.

1,513

Year built

1924

Style

Single Family Residential

County

Queen Anne's County

APN

02 006731

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 18, 2026.

NC-20

Neighborhood Conservation-20 District

There are several varieties of NC Districts. The NC Districts are intended to preserve the character, density, and scale of existing residential neighborhoods. The NC Districts allow existing neighborhoods to conform to this Chapter 18:1, and they allow for in-fill development to be compatible with the surrounding area. NC Districts are designated for existing residential developments as follows: NC-20: 20,000 sq ft average lot size.; All NC District regulations apply to NC Districts with a T designation on the Zoning Maps; except that single-wide manufactured homes are a permitted use within NC-T Districts.

Permitted uses

Include but are not limited to:

Equestrian facility
Housing-Single unit
Housing-Multiple units
Public service
Recreation
Housing-Mobile home park

Property details

Parking

Parking Information
# of Total Garage and Parking Spaces: 5
Driveway - # of Spaces: 5
Gravel Driveway
Driveway

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 3

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Full) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Full): 2

Interior Information
Interior Features: Attic, Stall Shower, Tub Shower, Built-Ins, CeilngFan(s), Floor Plan - Traditional, Formal/Separate Dining Room, Water Treat System, Wood Floors
Living Area Sq.Ft. Source: Assessor

Room Information
Living Room, Dining Room, Bedroom 2, Bedroom 3, Kitchen, Bedroom 1, Laundry, Office, Bathroom 1, Bathroom 2

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Gas/Propane

Basement Information
Basement: Yes
Unfinished

Exterior

Property Information
Total Below Grade Sq. Ft.: 676
Improvement Assessed Value: $203,000
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Foundation Details: Block
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Porch(es), Screened
Structure Type: Detached

Exterior Information
Outbuilding(s), Other

Lot Information
Lot Features: Backs to Trees, Corner, Rear Yard, SideYard(s)
Has Water View
Tidal Water: No

Land Information
Land Assessed Value: $81,700

Above Grade Information
Finished Sq.Ft.: 1,851
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft.: 676
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $2,555
Tax Assessed Value: $284,700
Tax Year: 2024
Tax Annual Amount: $2,555

Assessments Information
Year Assessed: 2025

Utilities

Utilities Information
Cooling Type: Ceiling Fan(s), Window Unit(s)
Cooling Fuel: Electric
Forced Air
Heating Fuel: Oil
Hot Water: Electric
Sewer Septic: Private Septic Tank
Water Source: Well
Municipal Trash: No

Location

School Information
Elementary School: CHURCH HILL
Middle Or Junior School: SUDLERSVILLE
High School: QUEEN ANNE'S COUNTY
School District Name: QUEEN ANNE'S COUNTY PUBLIC SCHOOLS
Elementary School Source: Listing Agent
Middle School Source: Listing Agent
High School Source: Listing Agent
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: 213 to Riverview. House is on the corner of 213 and Riverview.

Waterfrontage Information
Water Oriented
Water Body Type: River

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 1,513
Stories: 2.0
Lot Size: 0.51 acres
Style: Single Family Residential
Year Built: 1924
Year Renovated: —
County: Queen Anne's County
APN: 02 006731

Home facts updated by county records on Jul 17, 2026

Around this home

Schools

Church Hill Elementary School

Public PreK-4 • Assigned • 5.7mi

5/10

Sudlersville Middle School

Public 5-8 • Assigned • 11.0mi

5/10

Queen Anne's County High School

Public 9-12 • Assigned • 11.6mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

8/10 Heat Factor

7 days above 105° expected this year, 15 days in 30 years

6/10 Wind Factor

64% chance of strong winds in next 30 years

6/10 Air Factor

9 unhealthy days expected this year, 13 days in 30 years

Provided by First Street

Historical weather

Chestertown, MD • 21620

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.2 hours in June and 4.7 hours in December, which is comparable to the U.S. average for solar exposure.

9.2 hrs

4.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$394,000 – $477,000

Sell confidently with a local market expert in Chestertown. 3 minutes to get started.

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New listings for sale in 21620

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COMING SOON

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(410) 778-0330

COMING SOON

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3D WALKTHROUGH

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Home values near 221 Old Bridge Rd

Data from public records.

Address	Redfin Estimate
213 Old Bridge Road, Chestertown, MD 3 Beds \| 2.5 Baths \| 1440 Sq. Ft.	$407,822
217 Old Bridge Road, Chestertown, MD 3 Beds \| 2 Baths \| 1872 Sq. Ft.	$372,536

Address	Redfin Estimate
301 Old Bridge Road, Chestertown, MD 3 Beds \| 2 Baths \| 1416 Sq. Ft.	$349,945
209 Old Bridge Road, Chestertown, MD - Beds \| 1 Baths \| 1592 Sq. Ft.	$288,023

Address	Redfin Estimate
309 Old Bridge Road, Chestertown, MD - Beds \| 1 Baths \| 944 Sq. Ft.	$271,968
305 Old Bridge Road, Chestertown, MD - Beds \| 2.5 Baths \| 1584 Sq. Ft.	$380,432

Property information provided by BRIGHT MLS when last listed in 2025. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 21620, MD

Redfin agents who toured

Sale history for 221 Old Bridge Rd

Tax history for 221 Old Bridge Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21620

Home values near 221 Old Bridge Rd

More real estate resources