SOLD APR 10, 2026

Sold on Apr 2026

$332,000

•

1,628

sq ft

23055 Old Fairlee Rd, Chestertown, MD 21620

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About this home

OPEN HOUSE SATURDAY 3/7/26 FROM 11am-1pm HOPE TO SEE YOU THERE !!! Enjoy easy single-story living in this well-maintained 3-bedroom, 2-bath home situated on a ½-acre lot backing to peaceful farmland. Offering privacy and scenic views, this property blends comfort, space, and thoughtful upgrades throughout. Recent improvements include vinyl siding, a newer roof, and luxury vinyl plank flooring, with original hardwoods underneath for added value and charm. The spacious 12×27 eat-in kitchen is ideal for gatherings and features granite countertops and stainless steel appliances. Both bathrooms are generously sized, with the primary bath showcasing a classic cast iron tub with shower head. A newly added laundry/mudroom enhances everyday convenience and leads directly to a new 14×16 concrete patio and fenced rear yard, perfect for pets, play, or outdoor entertaining. Stay cozy during the colder months with a family room woodstove and warm forced-air heat. The detached two-car garage is topped with a durable 5-year-old metal roof, offering both storage and peace of mind. Town water and sewer add to the home’s practicality. Ideally located between the historic charm of Chestertown and the waterfront town of Rock Hall, this home offers access to quaint shops, fine waterfront dining, boating, hiking and biking trails, the YMCA, and the arts and cultural events of Washington College. A wonderful opportunity to enjoy a simpler lifestyle with a little something for everyone. Approximately 1.5 hour drive to Washington, DC and the Delaware beaches. If this lifestyle is for you, call me to schedule your personal showing.

Single-familyProperty Type

1948Year Built

0.5 acresLot Size

$204Price/Sq.Ft.

2 car garageParking

Listed by Debbie Callahan • Benson & Mangold, LLC

•443-988-0483 (broker)

•info@bensonandmangold.com (broker)

Bought with Kristina Hyland • Coldwell Banker Chesapeake Real Estate Company

•410-778-0330 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDKE2006062

Redfin Estimate

$363,179

$31K since sold in April 2026$2,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.6% higher than the average sale price ($325K) of 6 comparable homes.

SOLD SEP 1, 2026
$316,000
A
3 beds2 baths1,412 sq ft
10720 Foreston Rd, Chestertown, MD 21620
SOLD AUG 14, 2026
$318,000
B
3 beds2 baths1,397 sq ft
109 Cedar St, Chestertown, MD 21620
SOLD JUN 8, 2026
$293,000
C
3 beds2 baths1,152 sq ft
301 Lincoln Dr, Chestertown, MD 21620
SOLD JUL 16, 2026
$325,000
D
3 beds2 baths1,404 sq ft
10572 Watonga Rd, Chestertown, MD 21620
SOLD MAR 27, 2026
$350,000
E
3 beds2 baths1,942 sq ft
10751 Millbrook Dr, Chestertown, MD 21620
SOLD MAR 5, 2026
$350,000
F
3 beds2 baths1,680 sq ft
21111 Texas Ave, Chestertown, MD 21620

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Market trends in 21620, MD

Last updated August 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

COMING SOON
$489,000
2 beds2 baths1,098 sq ft
105 N Water St #3, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$659,999
3 beds3 baths2,716 sq ft
7712 Waterview Ln, Chestertown, MD 21620
(410) 778-0330
$315,000
3 beds1 bath1,008 sq ft
24775 Langford Rd, Chestertown, MD 21620
(410) 398-9200
$289,000
3 beds2 baths1,056 sq ft
8732 Elm Rd, Chestertown, MD 21620
(410) 778-0330
$1,295,000
4 beds3.5 baths3,383 sq ft
8276 Broad Neck Rd, Chestertown, MD 21620
(410) 810-3900
COMING SOON
$200,000
4 beds1 bath1,816 sq ft
223 Mount Vernon Ave, Chestertown, MD 21620
(443) 215-4663
$300,000
3 beds1 bath960 sq ft
104 Lincoln Dr, Chestertown, MD 21620
(443) 274-1900
COMING SOON
$568,900
4 beds2.5 baths2,464 sq ft
329 Union Church Rd, Chestertown, MD 21620
(443) 215-4663
$275,000
3 beds1 bath975 sq ft
7482 Poplar Ave, Chestertown, MD 21620
(301) 970-2447
$345,000
3 beds1.5 baths1,398 sq ft
217 Edmore Rd, Chestertown, MD 21620
(410) 810-0010
See all

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Rental estimate

Est. $2,793 per month, based on comparable rentals

Sale and tax history for 23055 Old Fairlee Rd

Sale History
Tax History

Date

Event

Price

BRIGHT MLS #MDKE2006062

Apr 10, 2026

Sold

$332,000

$204/sq ft

Mar 9, 2026

Pending

—

Mar 4, 2026

Listed

$330,000

$203/sq ft

Jan 17, 2026

Coming Soon

$330,000

$203/sq ft

BRIGHT MLS #MDKE114918

Jun 13, 2019

Sold

$199,000

$122/sq ft

May 8, 2019

Contingent

—

Apr 25, 2019

Price Changed

$199,000

$122/sq ft

Apr 15, 2019

Listed

$209,000

$128/sq ft

+17

MRIS #KE8113845

Jul 13, 2013

Delisted

—

Jun 20, 2013

Listed

Public Records

Jul 24, 2006

Sold

$150,000

$92/sq ft

MRIS #KE6100315

Jul 15, 2006

Delisted

—

Jun 23, 2006

Listed

$104/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2026

$2,428 (+37.1%)

2025

$1,770 (+5.6%)

2024

$1,677 (+5.5%)

2023

$1,589 (+6.4%)

$64,200 + $129,400

$193,600

2022

$1,493 (+5.5%)

2021

$1,415 (−0.1%)

2020

$1,417 (+0.8%)

$64,200 + $61,700

$125,900

2019

$1,406 (+0.8%)

2018

$1,395

$64,200 + $58,800

$123,000

2017

$1,395 (−0.9%)

$64,200 + $58,800

$123,000

2015

$1,407 (+100.0%)

$64,200 + $59,900

$124,100

2014

$704 (−53.3%)

2013

$1,507 (+4.5%)

2012

$1,443 (−4.7%)

2011

$1,514 (+141.0%)

2010

$628 (−47.2%)

2009

$1,191

Public record

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.5 Acres

Year renovated

—

Sq. Ft.

1,628

Year built

1948

Style

Single Family Residential

County

Kent County

APN

06 019226

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 3, 2026.

Property details

Parking

Parking Information
# of Detached Garage Spaces: 2
Garage Features: Garage - Front Entry
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Detached Garage, Driveway

Interior

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2

Interior Information
Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer, Exhaust Fan, Icemaker, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Washer, Water Heater
Interior Features: Attic, Tub Shower, Breakfast Area, Family Room Off Kitchen, Floor Plan - Traditional, Kitchen - Eat-In, Master Bath(s), Recessed Lighting, Wood Stove
Living Area Sq.Ft. Source: Assessor

Room Information
Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Laundry, Bathroom 2, Master Bathroom

Fireplace Information
Has Fireplace
# of Fireplaces: 1

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $160,100
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Vinyl Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Structure Type: Detached

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $64,200

Above Grade Information
Finished Sq.Ft.: 1,628
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
County Tax: $2,311
Tax Assessed Value: $203,833
Tax Year: 2025
Tax Annual Amount: $2,311

Assessments Information
Year Assessed: 2025

Utilities

Utilities Information
Cooling Type: Ceiling Fan(s), Ductless/Mini-Split, Window Unit(s)
Cooling Fuel: Electric
90% Forced Air, Forced Air, Wood Burn Stove
Heating Fuel: Propane - Leased, Wood
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public

Location

School Information
School District Name: KENT COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: Rt. 213 to Chestertown, Turn Left on Spring Ave and then Right on High St. Follow to traffic circle and take the 2nd exit onto Rt. 20 (towards Rock Hall). Continue approximately 5 miles to Right on Old Fairlee Rd. Go approximately 1/2 mile and property will be on the Left.

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 1,628
Stories: 1.0
Lot Size: 0.5 acres
Style: Single Family Residential
Year Built: 1948
Year Renovated: —
County: Kent County
APN: 06 019226

Home facts updated by county records on Aug 3, 2026

Around this home

Schools

Rock Hall Elementary School

Public PreK-5 • Assigned • 6.9mi

8/10

Kent County Middle School

Public 6-8 • Assigned • 5.9mi

3/10

Kent County High School

Public 9-12 • Assigned • 6.2mi

5/10

Provided by GreatSchools

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 104° expected this year, 15 days in 30 years

7/10 Wind Factor

79% 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 9.3 hours in June and 4.6 hours in December, which is comparable to the U.S. average for solar exposure.

9.3 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$346,000 – $418,000

Sell confidently with a local market expert in Chestertown.

Nearby similar homes

$289,000

3 beds2 baths1,056 sq ft

8732 Elm Rd, Chestertown, MD 21620

(410) 778-0330

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(410) 810-0010

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NEW CONSTRUCTION

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New listings for sale in 21620

COMING SOON

$489,000

2 beds2 baths1,098 sq ft

105 N Water St #3, Chestertown, MD 21620

(410) 778-0330

COMING SOON

$659,999

3 beds3 baths2,716 sq ft

7712 Waterview Ln, Chestertown, MD 21620

(410) 778-0330

$315,000

3 beds1 bath1,008 sq ft

24775 Langford Rd, Chestertown, MD 21620

(410) 398-9200

$289,000

3 beds2 baths1,056 sq ft

8732 Elm Rd, Chestertown, MD 21620

(410) 778-0330

$1,295,000

4 beds3.5 baths3,383 sq ft

8276 Broad Neck Rd, Chestertown, MD 21620

(410) 810-3900

COMING SOON

$200,000

4 beds1 bath1,816 sq ft

223 Mount Vernon Ave, Chestertown, MD 21620

(443) 215-4663

$300,000

3 beds1 bath960 sq ft

104 Lincoln Dr, Chestertown, MD 21620

(443) 274-1900

COMING SOON

$568,900

4 beds2.5 baths2,464 sq ft

329 Union Church Rd, Chestertown, MD 21620

(443) 215-4663

$275,000

3 beds1 bath975 sq ft

7482 Poplar Ave, Chestertown, MD 21620

(301) 970-2447

Home values near 23055 Old Fairlee Rd

Data from public records.

Address	Redfin Estimate
23077 Old Fairlee Road, Chestertown, MD 3 Beds \| 2.5 Baths \| 2222 Sq. Ft.	$361,059
23032 Old Fairlee Road, Chestertown, MD - Beds \| 1 Baths \| 1113 Sq. Ft.	$238,825

Address	Redfin Estimate
23051 Old Fairlee Road, Chestertown, MD 3 Beds \| 2 Baths \| 1675 Sq. Ft.	$345,521
23031 Old Fairlee Road, Chestertown, MD 2 Beds \| 1 Baths \| 1039 Sq. Ft.	$183,875

Address	Redfin Estimate
23045 Old Fairlee Road, Chestertown, MD - Beds \| 1 Baths \| 892 Sq. Ft.	$185,581
23025 Old Fairlee Road, Chestertown, MD - Beds \| 1 Baths \| 1640 Sq. Ft.	$231,536

Property information provided by BRIGHT MLS when last listed in 2026. This data may not match . Learn more.

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About this home

Redfin Estimate

Market trends in 21620, MD

Homeowner tools

Sale and tax history for 23055 Old Fairlee Rd

Public record

Property details

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 21620

Home values near 23055 Old Fairlee Rd

More real estate resources