OFF MARKET

Off market jun 2022 for $550K

$618,705

Est. refi paymentEst. refi $3,718/mo

•

2,329

sq ft

20520 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Ahhhhh, this feels like home! Well-maintained Leonardtown home with a large, private yard, in the established neighborhood of Chestnut Ridge -- the kind of community where everyone waves hello. An open floor plan with traditional appeal, this comfortable home shows well inside and out. A nice paved drive, new front hardscape, lush trees, and level lawn welcome you to the 2+ acre property. Many updates and custom features inside! Front living room with cathedral ceiling, lots of natural light, and custom wood shutters. Beautiful kitchen is warm and inviting with hand-scraped cherry hardwood floors, quality cabinetry, granite countertops, instant hot water, stainless steel appliances, and pantry. Back family room features a wood burning fireplace, and opens to an addition, which serves as a den/flex space. The upstairs offers a huge primary bedroom suite, with luxury bath, and a pleasant sitting room with bamboo flooring, many windows, and skylights. All three bedrooms have good closets, with pleasant views of the yard and trees beyond. The backyard is a real retreat, with a spacious back deck for outdoor dining and entertainment, lots of room to garden or play outside, a stone fire pit, and a 12x20 shed outfitted with electric, plenty of storage, cabinets and workbench, perfect for DIY projects and hobbies. Roof replaced in 2020, Dual HVAC's 2021, water heater 2022. Easy commute to NAS PAX, Leonardtown, nearby amenities. St. Mary's River State Park is close by, a popular place to hike or mountain bike on the 7-mile loop trail. A great place to call home!

Single-familyProperty Type

1995Year Built

2.22 acresLot Size

$266Est. Price/Sq.Ft.

2 car garageParking

Listed by Brooke Matthews • RE/MAX 100

•301-863-5355 (broker)

Bought with Robin Poe Errington • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDSM2007222

Redfin Estimate

$618,705

$69K since sold in June 2022$1,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.3% higher than the average sale price ($587K) of 5 comparable homes.

SOLD MAR 5, 2026
$560,000
A
4 beds2.5 baths2,594 sq ft
20753 Chestnut Ridge Dr, Leonardtown, MD 20650
SOLD SEP 18, 2026
$605,000
B
3 beds2.5 baths2,052 sq ft
20980 Aster Dr, Callaway, MD 20620
SOLD MAY 14, 2026
$727,360
C
4 beds2.5 baths2,972 sq ft
43500 Deer Run Ct, Leonardtown, MD 20650
SOLD JAN 23, 2026
$465,000
D
3 beds2 baths1,732 sq ft
43543 Bayberry Ct, Leonardtown, MD 20650
SOLD MAY 11, 2026
$579,900
E
4 beds2.5 baths3,428 sq ft
43552 Bayberry Ct, Leonardtown, MD 20650

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Earn from this home

Sell

$177,107

Est. take-home

List your home with Redfin and save $6,187

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,583/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

100.7%

+0.6% MoM

Median sale price

$535K

$30K MoM

Avg. days on market

49d

5 days MoM

Recently sold homes

13 MoM

New listings for sale

$475,000
4 beds2.5 baths2,200 sq ft
43261 Cedarwood Ct, Leonardtown, MD 20650
(888) 860-7369
NEW 18 HRS AGO
$290,000
3 beds2 baths1,568 sq ft
43905 Lanedon Dr, Leonardtown, MD 20650
(301) 702-4200
COMING SOON
$590,000
4 beds4 baths3,750 sq ft
22220 Bull Rd, Leonardtown, MD 20650
(301) 855-8600
$620,000
5 beds2.5 baths4,836 sq ft
23636 Hansel Ct, Leonardtown, MD 20650
(301) 970-2447
$929,900
4 beds3.5 baths4,248 sq ft
20945 Greenwell Way, Leonardtown, MD 20650
(301) 863-2400
COMING SOON
$475,000
3 beds2 baths1,462 sq ft
43705 Redmond Rd, Leonardtown, MD 20650
(301) 609-9000
$474,900
3 beds2 baths1,710 sq ft
41495 Garrett Ct, Leonardtown, MD 20650
(301) 884-9493
$650,000
4 beds3.5 baths3,344 sq ft
23513 Sly Fox Way, Leonardtown, MD 20650
(443) 771-8009
COMING SOON
$549,000
4 beds3.5 baths3,006 sq ft
23208 Clarks Rest Rd, Leonardtown, MD 20650
(443) 771-8009
See all

Provided by Redfin

Sale history for 20520 Chestnut Ridge Dr

Date

Event

Price

BRIGHT MLS #MDSM2007222

Jun 21, 2022

Sold

$550,000

$236/sq ft

May 20, 2022

Pending

—

May 19, 2022

Listed

$550,000

$236/sq ft

Public Records

Aug 7, 2012

Sold

$360,000

$155/sq ft

MRIS #SM7865259

Jul 29, 2012

Sold

$359,900

$155/sq ft

Jun 23, 2012

Pending

—

Jun 20, 2012

Relisted

—

Jun 20, 2012

Pending

—

Jun 15, 2012

Listed

$155/sq ft

+18

BRIGHT MLS #1004035454

Jul 29, 2012

Sold

$359,900

$155/sq ft

Jun 27, 2012

Listing Removed

—

Jun 15, 2012

Listed

$359,900

$155/sq ft

+18

Public Records

Oct 26, 1993

Sold

$42,000

$18/sq ft

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$5,904 (+4.5%)

2024

$5,648 (+5.7%)

$126,100 + $410,400

$536,500

2023

$5,342 (+2.7%)

2022

$5,204 (+3,223.6%)

2021

$157 (+1.2%)

$126,100 + $226,100

$352,200

2020

$155 (+1.2%)

2019

$153 (−95.4%)

2018

$3,350 (+1.1%)

2017

$3,314 (+4.6%)

2015

$3,169 (−9.9%)

$121,100 + $190,200

$311,300

2014

$3,519 (+117.1%)

$121,100 + $212,800

$333,900

2013

$1,621 (−47.4%)

2012

$3,081 (+3.1%)

2011

$2,989

2010

$2,989 (+20.8%)

2009

$2,475

Tax history for 20520 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$5,904 (+4.5%)

2024

$5,648 (+5.7%)

$126,100 + $410,400

$536,500

2023

$5,342 (+2.7%)

2022

$5,204 (+3,223.6%)

2021

$157 (+1.2%)

$126,100 + $226,100

$352,200

2020

$155 (+1.2%)

2019

$153 (−95.4%)

2018

$3,350 (+1.1%)

2017

$3,314 (+4.6%)

2015

$3,169 (−9.9%)

$121,100 + $190,200

$311,300

2014

$3,519 (+117.1%)

$121,100 + $212,800

$333,900

2013

$1,621 (−47.4%)

2012

$3,081 (+3.1%)

2011

$2,989

2010

$2,989 (+20.8%)

2009

$2,475

*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
Permits

Beds

—

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

2.22 Acres

Year renovated

—

Sq. Ft.

2,325

Year built

1995

Style

Single Family Residential

County

St. Mary's County

APN

03 053571

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 18, 2026.

May 28, 2010 • Final

Bldg new construction

Construct an addition to the living area of a residential building.

Addition

May 28, 2009 • Active

Residential addition

Construct an addition to the living area of a residential building.

Addition

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Property details

Parking

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

Interior

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

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: Cooktop, Dishwasher, Dryer, Exhaust Fan, Icemaker, Oven - Wall, Refrigerator, Stainless Steel Appliances, Washer, Instant Hot Water
Flooring Type: Carpet, Hardwood
Not Furnished
Interior Features: Carpet, CeilngFan(s), Pantry, Upgraded Countertops, Wood Floors, Floor Plan - Open, Walk-in Closet(s), Skylight(s), Master Bath(s), Breakfast Area, Combination Kitchen/Living, Dining Area, Family Room Off Kitchen, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Table Space, Tub Shower, Store/Office
Living Area Sq.Ft. Source: Estimated
Wall & Ceiling Types: Cathedral Ceilings

Room Information
Living Room, Dining Room, Master Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Kitchen, Family Room, Office, Utility Room, Master Bathroom, Full Bath, Half Bath

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Wood

Basement Information
Basement: No

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Vinyl Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s)
Roof: Asphalt
Structure Type: Detached
Window Features: Screens
Other Structures: Shed

Lot Information
Lot Features: Backs to Trees, Level
Tidal Water: No

Land Information
Land Assessed Value: $126,100

Above Grade Information
Finished Sq.Ft.: 2,329
Finished Sq.Ft. Source: Estimated

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

Financial

Tax Information
Agricultural Tax Due: No
Tax Assessed Value: $35,200
Tax Year: 2022
Tax Annual Amount: $3,459

Assessments Information
Year Assessed: 2022

Lease Information
Lease Considered: No

Utilities

Utilities Information
Central Air
Cooling Type: Ceiling Fan(s), Central A/C, Zoned
Cooling Fuel: Electric
Heat Pump(s), Zoned
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Private Septic Tank
Water Source: Well
Municipal Trash: No

Location

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

School Information
High School: LEONARDTOWN
School District Name: ST. MARY'S COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: Three Notch to Great Mills Rd. Turn Right onto Pt Lookout Rd/MD-5. Turn left onto Chestnut Ridge Dr. Home on Left
Municipality: Unincorporated

Public facts

Beds: —
Baths: 2.5
Sq. Ft.: 2,325
Stories: 2.0
Lot Size: 2.22 acres
Style: Single Family Residential
Year Built: 1995
Year Renovated: —
County: St. Mary's County
APN: 03 053571

Home facts updated by county records on Jul 18, 2026

Around this home

Schools

Piney Point Elementary School

Public PreK-5 • Assigned • 5.0mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.5mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 3.2mi

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 102° 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

$588,000 – $712,000

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Nearby similar homes

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New listings for sale in 20650

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(888) 860-7369

NEW 18 HRS AGO

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COMING SOON

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COMING SOON

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COMING SOON

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Home values near 20520 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20482 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2911 Sq. Ft.	$606,354
20525 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3194 Sq. Ft.	$582,926

Address	Redfin Estimate
20479 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2400 Sq. Ft.	$568,721
20500 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2694 Sq. Ft.	$583,890

Address	Redfin Estimate
20507 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 3 Baths \| 1705 Sq. Ft.	$546,949
20496 Chestnut Ridge Dr, Leonardtown, MD 5 Beds \| 4.5 Baths \| 2945 Sq. Ft.	$622,451

Property information provided by BRIGHT MLS when last listed in 2022. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Sale history for 20520 Chestnut Ridge Dr

Tax history for 20520 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 20520 Chestnut Ridge Dr

More real estate resources