SOLD MAR 5, 2026

Off market mar 2026 for $560K

$599,070

Est. refi paymentEst. refi $4,328/mo

•

2,594

sq ft

20753 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Nestled within one of the most desirable subdivisions, this classic two-story Colonial welcomes you home with charm and a sense of privacy on two wooded acres. Quality construction throughout from the sunroom to the kitchen remodel you will see the workmanship! Once inside you will feel the warmth of meticulously cared-for details : gleaming hardwood floors through the main level, a spacious separate dining room into a beautifully updated kitchen. Corian countertops, stainless steel appliances, and center island make it a joy to cook and gather Kitchen opens into a cozy family room anchored by a wood-burning fireplace and a light-filled sunroom with lots of windows inviting the outside in. Connecting deck overlooking your own peaceful woods Upstairs, four generous bedrooms offer restful retreats, including a primary suite with an en-suite bath featuring dual vanities, a soothing soaking tub, a separate shower, and a spacious walk-in closet. Practical touches complete the picture: an oversized two-car garage for all your toys and storage, plus a charming large Amish-built shed Bonus! Encapsulated crawlspace w/ commercial grade dehumidifier, sprinkler system, heat pump 2024, new roof 2016

Single-familyProperty Type

1994Year Built

2 acresLot Size

$231Est. Price/Sq.Ft.

2 car garageParking

Listed by Tracey Summers • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Bought with Cindy Ballard • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDSM2028218

Redfin Estimate

$599,070

$39K since sold in March 2026$6,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.4% lower than the average sale price ($668K) of 5 comparable homes.

SOLD AUG 31, 2026
$976,000
A
4 beds2.5 baths2,550 sq ft
41402 Philip Ln, Leonardtown, MD 20650
SOLD MAY 11, 2026
$579,900
B
4 beds2.5 baths3,428 sq ft
43552 Bayberry Ct, Leonardtown, MD 20650
SOLD MAY 14, 2026
$727,360
C
4 beds2.5 baths2,972 sq ft
43500 Deer Run Ct, Leonardtown, MD 20650
SOLD MAR 26, 2026
$554,000
D
4 beds2.5 baths2,655 sq ft
44180 Cross Bow Ln, California, MD 20619
SOLD MAY 15, 2026
$505,000
E
4 beds2.5 baths2,368 sq ft
21027 Hunting Quarter Dr, Callaway, MD 20620

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

Earn from this home

Sell

$119,599

Est. take-home

List your home with Redfin and save $5,991

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,692/mo

Redfin rental estimate

List your home for rent

Market trends in 20650, MD

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.2%

+0.5% MoM

Median sale price

$480K

$55K MoM

Avg. days on market

39d

10 days MoM

Recently sold homes

16 MoM

New listings for sale

$650,000
4 beds3.5 baths3,264 sq ft
41427 Osborne Ln, Leonardtown, MD 20650
(443) 771-8009
OPEN SAT, 1PM TO 3PM
$440,000
3 beds3.5 baths2,379 sq ft
41608 Briarwood Cir, Leonardtown, MD 20650
(301) 298-2892
COMING SOON
$685,000
5 beds3.5 baths4,271 sq ft
23603 Margrave Dr, Leonardtown, MD 20650
(888) 860-7369
$590,000
4 beds4 baths3,750 sq ft
22220 Bull Rd, Leonardtown, MD 20650
(301) 855-8600
$299,500
3 beds1.5 baths1,218 sq ft
42163 Blacksmith Shop Rd, Leonardtown, MD 20650
(301) 862-2169
VIDEO TOUR
$450,000
3 beds3.5 baths2,306 sq ft
23405 Marview Ct, Leonardtown, MD 20650
(410) 394-0990
$450,000
3 beds2 baths1,462 sq ft
43705 Redmond Rd, Leonardtown, MD 20650
(301) 609-9000
$515,000
4 beds3.5 baths2,764 sq ft
22538 Landing Way, Leonardtown, MD 20650
(443) 771-8009
See all

Provided by Redfin

Sale history for 20753 Chestnut Ridge Dr

Tax history for 20753 Chestnut Ridge Dr

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

Public record

Beds

—

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

2 Acres

Year renovated

—

Sq. Ft.

2,980

Year built

1994

Style

Single Family Residential

County

St. Mary's County

APN

03 048489

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 16, 2026.

Property details

Parking

Parking Information
# of Attached Garage Spaces: 2
Garage Features: Garage - Front Entry, Garage Door Opener, Inside Access, Oversized
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Attached Garage

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 4

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

Interior Information
Appliances: Dishwasher, Dryer, Exhaust Fan, Microwave, Oven - Double, Oven/Range - Electric, Refrigerator, Washer
Interior Features: Bathroom - Walk-In Shower, Chair Railings, Crown Moldings, Kitchen - Island, Master Bath(s), Pantry, Upgraded Countertops, Wood Floors
Living Area Sq.Ft. Source: Estimated

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Brick, Wood

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $340,800
Ownership Interest: Fee Simple
Property Condition: Excellent
Year Built Source: Assessor

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

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $125,000

Above Grade Information
Finished Sq.Ft.: 2,594
Finished Sq.Ft. Source: Estimated

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

Financial

Tax Information
County Tax: $4,471
Tax Assessed Value: $465,800
Tax Year: 2025
Tax Annual Amount: $4,471

Assessments Information
Year Assessed: 2025

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C, Ceiling Fan(s), Heat Pump(s)
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Septic Exists
Water Source: Private

Location

Homeowners Association Information
HOA Fee: $100
HOA Fee Frequency: Annually

School Information
Middle Or Junior School: LEONARDTOWN
High School: LEONARDTOWN
School District Name: ST. MARYS COUNTY PUBLIC SCHOOLS
Middle School Source: 3rd Party
High School Source: 3rd Party
School District Source: 3rd Party

Location Information
Outside City Limits
Directions: Rt 5 To Chestnut Ridge Subdivision to property on right

Public facts

Beds: —
Baths: 2.5
Sq. Ft.: 2,980
Stories: 2.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 1994
Year Renovated: —
County: St. Mary's County
APN: 03 048489

Home facts updated by county records on Oct 16, 2026

Around this home

Schools

Piney Point Elementary School

Public PreK-5 • Assigned • 5.4mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.1mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 2.7mi

8/10

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

9/10 Heat Factor

7 days above 101° expected this year, 17 days in 30 years

6/10 Wind Factor

41% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Leonardtown, MD • 20650

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 9.5 hours in June and 4.9 hours in December, which is comparable to the U.S. average for solar exposure.

9.5 hrs

4.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$570,000 – $689,000

Reach more buyers when you sell with Redfin. Save up to $5,991 in fees. 3 minutes to get started.

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

Nearby similar homes

$929,900

4 beds3.5 baths4,248 sq ft

20945 Greenwell Way, Leonardtown, MD 20650

(301) 863-2400

$525,000

4 beds3.5 baths3,019 sq ft

22999 Ringtail Dr, California, MD 20619

(301) 862-2169

$475,000

3 beds2.5 baths1,668 sq ft

22435 Indian Bridge Rd, California, MD 20619

(443) 771-8009

$449,900

4 beds3 baths2,414 sq ft

20893 Dry Mill St, Great Mills, MD 20634

(301) 863-2400

$444,500

4 beds4 baths2,666 sq ft

20270 Beauvue Ct, Leonardtown, MD 20650

(301) 645-1700

$425,000

4 beds2 baths2,022 sq ft

22712 Parkview Dr, California, MD 20619

(301) 862-2169

New listings for sale in 20650

$650,000

4 beds3.5 baths3,264 sq ft

41427 Osborne Ln, Leonardtown, MD 20650

(443) 771-8009

OPEN SAT, 1PM TO 3PM

$440,000

3 beds3.5 baths2,379 sq ft

41608 Briarwood Cir, Leonardtown, MD 20650

(301) 298-2892

COMING SOON

$685,000

5 beds3.5 baths4,271 sq ft

23603 Margrave Dr, Leonardtown, MD 20650

(888) 860-7369

$590,000

4 beds4 baths3,750 sq ft

22220 Bull Rd, Leonardtown, MD 20650

(301) 855-8600

$299,500

3 beds1.5 baths1,218 sq ft

42163 Blacksmith Shop Rd, Leonardtown, MD 20650

(301) 862-2169

VIDEO TOUR

$450,000

3 beds3.5 baths2,306 sq ft

23405 Marview Ct, Leonardtown, MD 20650

(410) 394-0990

$450,000

3 beds2 baths1,462 sq ft

43705 Redmond Rd, Leonardtown, MD 20650

(301) 609-9000

$515,000

4 beds3.5 baths2,764 sq ft

22538 Landing Way, Leonardtown, MD 20650

(443) 771-8009

Home values near 20753 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20829 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3.5 Baths \| 3683 Sq. Ft.	$568,011
20735 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3 Baths \| 2568 Sq. Ft.	$605,379

Address	Redfin Estimate
20784 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3 Baths \| 2802 Sq. Ft.	$594,056
20854 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3 Baths \| 2498 Sq. Ft.	$589,069

Address	Redfin Estimate
20776 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2606 Sq. Ft.	$539,256
20815 Chestnut Ridge Drive, Leonardtown, MD 3 Beds \| 2 Baths \| 1620 Sq. Ft.	$516,023

Property information provided by BRIGHT MLS when last listed in 2025. 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 Leonardtown	Agents near me	Rockville, MD homes for sale	Leonardtown 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	Bowie, MD homes for sale	Leonardtown Property Records
Condos for sale near me	Silver Spring, MD homes for sale	MD New Listings

20650 homes for sale
20627 homes for sale
20636 homes for sale

Lusby homes for sale
Colonial Beach homes for sale
Mechanicsville homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Sale history for 20753 Chestnut Ridge Dr

Tax history for 20753 Chestnut Ridge Dr

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 20650

Home values near 20753 Chestnut Ridge Dr

More real estate resources