OFF MARKET

Off Market Sep 2019 for $675K

$1,124,523

Est. refi paymentEst. refi $3,964/mo

•

2,182

sq ft

244 River Rd, Chestertown, MD 21620

About this home

Enjoy the best of Chestertown waterfront living! This beautifully updated home nestles on the shoreline of the Chester River with breathtaking views across the bridge from historic Chestertown. Meticulously renovated in 2015, this property is open and airy with superior custom molding and craftsmanship to be seen in every room. Kitchen boasts stainless steel appliances with granite counters and ceramic tile floor. The Kitchen flows into the Dining Room with its custom built large wooden cabinet, hardwood floors, stunning decorative chandelier, and bay window. The Living Room offers soothing wood burning fireplace and hardwood floors. A large Sun Room stretching across the entire river side of the property with walls of Anderson sliding glass doors allows for abundant natural light and gorgeous water views. Perfect for entertaining! The side hallway leads to the main level master bedroom and offers custom shuttered windows, spacious closet, decorative ceiling fan, and hardwood floors leading into the luxurious private Owner's Bath. This custom ceramic tile oasis offers walk in shower surrounded by a glass enclosure, decorative mirror built into the wall overlooking large vanity, and wonderful storage. The other two spacious bedrooms on the main level boast hardwood floors, large closets along with custom built bookcases and plantation style shutters for the windows. The second main level full bath offers a custom ceramic tile walk in shower with bench and sliding glass enclosure. The steps ascending to the upper level lead to a Recreation Room/Office and another private suite complete with vaulted ceilings, large skylights and private full bathroom. The lower level has a full basement with a french drainage system, extra large cedar closet for storage, laundry area, and access to a deep one car garage that leads to the asphalt driveway. A BATS Septic installed in 2016, a nearly new deep water pier and private beach complete the offering. Don't miss out on this opportunity of a lifetime!

Single-familyProperty Type

1962Year Built

0.89 acresLot Size

$515Est. Price/Sq.Ft.

1 car garageParking

Listed by Angela Demattia • Berkshire Hathaway HomeServices PenFed Realty

•410-647-8000 (broker)

•severnapark@penfedrealty.com (broker)

Bought with Lish Gannon • Benson & Mangold, LLC

•410-770-9255 (broker)

•info@bensonandmangold.com (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDQA139824

Redfin Estimate

$1,124,523

$450K since sold in September 2019$102K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 73.5% higher than the average sale price ($648K) of 6 comparable homes.

SOLD AUG 14, 2026
$1,200,000
A
4 beds3 baths2,292 sq ft
202 Royston Shores Rd, Chestertown, MD 21620
SOLD JUL 14, 2026
$453,000
B
3 beds2.5 baths2,060 sq ft
704 Truslow Rd, Chestertown, MD 21620
SOLD APR 17, 2026
$495,000
C
4 beds2.5 baths2,220 sq ft
515 N Kent St, Chestertown, MD 21620
SOLD MAR 18, 2026
$325,000
D
3 beds2.5 baths2,034 sq ft
121 Primrose Rd, Chestertown, MD 21620
SOLD JUN 26, 2026
$1,050,000
E
5 beds3 baths2,956 sq ft
231 Richard Dr, Chestertown, MD 21620
SOLD JUL 22, 2026
$365,000
F
3 beds2 baths1,934 sq ft
521 N Kent St, Chestertown, MD 21620

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$593,891

Est. take-home

List your home with Redfin and save $11,245

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,882/mo

Redfin rental estimate

List your home for rent

Market trends in 21620, MD

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

98.0%

+0.0% MoM

Median sale price

$362K

$17K MoM

Avg. days on market

46d

14 days MoM

Recently sold homes

9 MoM

New listings for sale

OPEN SAT, 11AM TO 1PM
$225,000
4 beds1.5 baths1,800 sq ft
533 Round Top Rd, Chestertown, MD 21620
(833) 335-7433
$304,000
3 beds2 baths1,232 sq ft
7464 Shortall St, Chestertown, MD 21620
(410) 476-2201
COMING SOON
$675,000
5 beds3 baths2,838 sq ft
212 Washington Ave, Chestertown, MD 21620
(410) 778-0330
$38,200,000
4 beds2 baths2,330 sq ft
8184 Rock Hall Rd, Chestertown, MD 21620
(410) 778-3779
$1,195,000
2 beds1 bath806 sq ft
302 S Mill St, Chestertown, MD 21620
(410) 778-0330
COMING SOON
$345,000
3 beds1.5 baths1,398 sq ft
217 Edmore Rd, Chestertown, MD 21620
(410) 810-0010
$369,000
2 beds1.5 baths1,036 sq ft
101 S College Ave, Chestertown, MD 21620
(410) 810-0010
$649,000
4 beds3 baths2,864 sq ft
22400 Great Oak Landing Rd, Chestertown, MD 21620
(410) 778-0330
FOR SALE BY OWNER
$435,000
3 beds2 baths1,956 sq ft
233 Duke of Kent St, Chestertown, MD 21620
$524,900
3 beds2.5 baths2,076 sq ft
1003 Twin Ct, Chestertown, MD 21620
(410) 778-3779
See all

Provided by Redfin

Sale history for 244 River Rd

Year

Property tax

Land + Additions

Assessment*

2025

$8,747 (+10.5%)

2024

$7,917 (+11.7%)

$508,300 + $413,900

$922,200

2023

$7,086 (+13.3%)

2022

$6,256 (+5.1%)

2021

$5,952 (+7.5%)

$305,100 + $352,600

$657,700

2020

$5,536 (+8.1%)

2019

$5,120 (+2.7%)

2018

$4,984 (+2.8%)

$289,000 + $238,600

$527,600

2017

$4,847 (+2.9%)

2016

$4,710

$289,000 + $195,900

$484,900

2015

$4,710 (−14.7%)

$289,000 + $195,900

$484,900

2014

$5,522

$389,000 + $180,500

$569,500

2013

$5,522 (+0.5%)

2012

$5,492 (+4.5%)

2011

$5,257 (+3.6%)

2010

$5,075 (+6.3%)

2009

$4,772

Tax history for 244 River Rd

Year

Property tax

Land + Additions

Assessment*

2025

$8,747 (+10.5%)

2024

$7,917 (+11.7%)

$508,300 + $413,900

$922,200

2023

$7,086 (+13.3%)

2022

$6,256 (+5.1%)

2021

$5,952 (+7.5%)

$305,100 + $352,600

$657,700

2020

$5,536 (+8.1%)

2019

$5,120 (+2.7%)

2018

$4,984 (+2.8%)

$289,000 + $238,600

$527,600

2017

$4,847 (+2.9%)

2016

$4,710

$289,000 + $195,900

$484,900

2015

$4,710 (−14.7%)

$289,000 + $195,900

$484,900

2014

$5,522

$389,000 + $180,500

$569,500

2013

$5,522 (+0.5%)

2012

$5,492 (+4.5%)

2011

$5,257 (+3.6%)

2010

$5,075 (+6.3%)

2009

$4,772

*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

1.5

Lot width

—

Lot depth

—

Lot size

0.88 Acres

Year renovated

—

Sq. Ft.

2,182

Year built

1962

Style

Single Family Residential

County

Queen Anne's County

APN

02 014262

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 Attached Garage Spaces: 1
Garage Features: Garage Door Opener, Garage - Side Entry
# of Total Garage and Parking Spaces: 1
Has Garage
# of Garage Spaces: 1
Asphalt Driveway, Paved Driveway
Attached Garage, Off Street, On Street, Driveway

Interior

Virtual Tour

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

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Full): 3

Interior Information
Appliances: Built-In Microwave, Dishwasher, Disposal, Dryer, Exhaust Fan, Refrigerator, Stove, Stainless Steel Appliances, Washer, Water Conditioner - Owned, Water Heater - Tankless
Door Features: Sliding Glass, Storm
Flooring Type: Hardwood, Ceramic Tile, Carpet
Interior Features: Built-Ins, Carpet, Cedar Closet(s), CeilngFan(s), Chair Railings, Crown Moldings, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Gourmet, Master Bath(s), Recessed Lighting, Water Treat System, Wood Floors, Other
Living Area Sq.Ft. Source: Assessor

Room Information
Laundry Type: Basement, Lower Floor

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Flue for Stove, Mantel(s), Screen, Wood

Basement Information
Basement: Yes
Full, Garage Access, Heated, Outside Entrance, Interior Access, Sump Pump, Unfinished, Walkout Level

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Horse: No
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Assessor
Year Major Reno/Remodel: 2015

Building Information
Construction Materials: Brick
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Porch(es)
Roof: Architectural Shingle
Structure Type: Detached
Window Features: Double Pane, Insulated, Screens, Skylights
Other Structures: Shed

Exterior Information
Extensive Hardscape, Sidewalks, Other

Lot Information
Lot Features: Cleared, Landscaping, Premium
Lot Size Dimensions: 0.00 x 0.00
Navigable Water
Has Water View
Water Frontage In Feet: 130

Dock Information
Dock Type and Features: Private
Dock/Slip Conveyance: Physical Dock/Slip Conveys
# of Docks: 1
Dock/Slip Conveys: Yes

Above Grade Information
Finished Sq.Ft.: 2,182
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
Agricultural Tax Due: No
County Tax: $4,469
Tax Assessed Value: $527,600
Tax Year: 2018
Tax Annual Amount: $5,060

Assessments Information
Year Assessed: 2019

Lease Information
Lease Considered: No

Utilities

Utilities Information
Central Air
Cooling Type: Ceiling Fan(s), Central A/C, Air Purification System
Cooling Fuel: Electric
Forced Air
Heating Fuel: Propane - Owned
Hot Water: Tankless
Sewer Septic: Septic Exists, Septic = # of BR, Nitrogen Removal System
Propane
Water Source: Private/Community Water

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: 3rd Party
Middle School Source: 3rd Party
High School Source: 3rd Party
School District Source: 3rd Party

Location Information
Outside City Limits
Directions: MD-213 (Church Hill Rd) to Truslow Road. Right onto River Road. Property is on the right hand side. Look for the Berkshire Hathaway HomeServices PenFed Realty sign.
Location Type: River
Mean Low Water Feet: 3

Waterfrontage Information
Water Access Features: Private Access, Canoe/Kayak, Fishing Allowed, Boat - Powered, Sail, Personal Watercraft (PWC), Swimming Allowed, Waterski/Wakeboard
Water Access
Private Dock Site, Sandy Beach, Rip-Rap
On Waterfront
Water Oriented
Water Body Type: River
Water Body Name: Chester River

Public facts

Beds: —
Baths: 3.0
Sq. Ft.: 2,182
Stories: 1.5
Lot Size: 0.88 acres
Style: Single Family Residential
Year Built: 1962
Year Renovated: —
County: Queen Anne's County
APN: 02 014262

Home facts updated by county records on Jul 17, 2026

Around this home

Schools

Church Hill Elementary School

Public PreK-4 • Assigned • 5.5mi

5/10

Sudlersville Middle School

Public 5-8 • Assigned • 11.4mi

5/10

Queen Anne's County High School

Public 9-12 • Assigned • 10.8mi

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 104° expected this year, 15 days in 30 years

6/10 Wind Factor

59% 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

$1.07M – $1.29M

Reach more buyers when you sell with Redfin. Save up to $11,245 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

NEW CONSTRUCTION

$305,000

3 beds2 baths1,300 sq ft

11037 Bottom Rd, Worton, MD 21678

(410) 972-4000

$275,000

3 beds1 bath1,248 sq ft

956 Washington Ave, Chestertown, MD 21620

(410) 810-0010

$750,000

— beds1 bath2,045 sq ft

201 N Lynchburg St, Chestertown, MD 21620

(302) 234-3800

FOR SALE BY OWNER

$435,000

3 beds2 baths1,956 sq ft

233 Duke of Kent St, Chestertown, MD 21620

$395,000

2 beds1.5 baths1,440 sq ft

224 Ewingtown Rd, Church Hill, MD 21623

(410) 810-0010

$359,997

4 beds3 baths2,208 sq ft

25133 Smithville Rd, Worton, MD 21678

(443) 320-1344

New listings for sale in 21620

OPEN SAT, 11AM TO 1PM

$225,000

4 beds1.5 baths1,800 sq ft

533 Round Top Rd, Chestertown, MD 21620

(833) 335-7433

$304,000

3 beds2 baths1,232 sq ft

7464 Shortall St, Chestertown, MD 21620

(410) 476-2201

COMING SOON

$675,000

5 beds3 baths2,838 sq ft

212 Washington Ave, Chestertown, MD 21620

(410) 778-0330

$38,200,000

4 beds2 baths2,330 sq ft

8184 Rock Hall Rd, Chestertown, MD 21620

(410) 778-3779

$1,195,000

2 beds1 bath806 sq ft

302 S Mill St, Chestertown, MD 21620

(410) 778-0330

COMING SOON

$345,000

3 beds1.5 baths1,398 sq ft

217 Edmore Rd, Chestertown, MD 21620

(410) 810-0010

$369,000

2 beds1.5 baths1,036 sq ft

101 S College Ave, Chestertown, MD 21620

(410) 810-0010

$649,000

4 beds3 baths2,864 sq ft

22400 Great Oak Landing Rd, Chestertown, MD 21620

(410) 778-0330

FOR SALE BY OWNER

$435,000

3 beds2 baths1,956 sq ft

233 Duke of Kent St, Chestertown, MD 21620

Home values near 244 River Rd

Data from public records.

Address	Redfin Estimate
239 River Road, Chestertown, MD - Beds \| 2.5 Baths \| 2212 Sq. Ft.	$396,287
219 River Road, Chestertown, MD 3 Beds \| 2 Baths \| 1848 Sq. Ft.	—

Address	Redfin Estimate
217 River Road, Chestertown, MD 4 Beds \| 2.5 Baths \| 2754 Sq. Ft.	$279,174
305 River Road, Chestertown, MD - Beds \| 2 Baths \| 1369 Sq. Ft.	$380,215

Address	Redfin Estimate
313 River Road, Chestertown, MD 4 Beds \| 2.5 Baths \| 2080 Sq. Ft.	$426,939
238 River Road, Chestertown, MD 5 Beds \| 3.5 Baths \| 3100 Sq. Ft.	$1,082,875

Property information provided by BRIGHT MLS when last listed in 2019. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Houses for rent in Kingstown	Agents near me	Rockville, MD homes for sale	Kingstown Housing Market
Houses for sale near me	Baltimore, MD homes for sale	Frederick, MD homes for sale
Land for sale near me	Bethesda, MD homes for sale	Columbia, MD homes for sale
Open Houses near me	Silver Spring, MD homes for sale	Kingstown Property Records
Condos for sale near me	Bowie, MD homes for sale	MD New Listings

Chester homes for sale
Chestertown homes for sale
Stevensville homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 21620, MD

Sale history for 244 River Rd

Tax history for 244 River 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 244 River Rd

More real estate resources