OFF MARKET

Off market sep 2012 for $355K

$548,475

Est. refi paymentEst. refi $2,836/mo

•

1,705

sq ft

20507 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Single-familyProperty Type

1994Year Built

4.19 acresLot Size

$322Est. Price/Sq.Ft.

2 car garageParking

Listed by Robin Poe Errington • 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: 6 minutes ago

•Source:BRIGHT MLS #1004085126

Redfin Estimate

$548,475

$193K since sold in September 2012$2,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10% lower than the average sale price ($609K) of 6 comparable homes.

SOLD SEP 18, 2026
$605,000
A
3 beds2.5 baths2,052 sq ft
20980 Aster Dr, Callaway, MD 20620
SOLD SEP 8, 2026
$674,000
B
4 beds3.5 baths3,381 sq ft
20750 Deer Wood Park Dr, 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 JAN 23, 2026
$465,000
D
3 beds2 baths1,732 sq ft
43543 Bayberry Ct, Leonardtown, MD 20650
SOLD NOV 26, 2025
$625,000
E
3 beds2.5 baths2,742 sq ft
43107 Gum Spring Dr, Leonardtown, MD 20650
SOLD MAR 5, 2026
$560,000
F
4 beds2.5 baths2,594 sq ft
20753 Chestnut Ridge Dr, Leonardtown, MD 20650

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Earn from this home

Sell

$323,908

Est. take-home

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Refinance

Est. cash available

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Rent

$2,697/mo

Redfin rental estimate

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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

LISTED BY REDFIN
$489,900
3 beds2.5 baths1,976 sq ft
22301 White Oak Rd, Leonardtown, MD 20650
$79,900
— beds— baths1,542 sq ft
21944 Point Lookout Rd, Leonardtown, MD 20650
(443) 968-9595
COMING SOON
$467,000
3 beds2.5 baths1,568 sq ft
22630 Quiet Ln, Leonardtown, MD 20650
(301) 884-9493
COMING SOON
$2,200,000
4 beds3 baths4,395 sq ft
22395 Newtowne Neck Rd, Leonardtown, MD 20650
(443) 975-7555
$650,000
4 beds3.5 baths3,264 sq ft
41427 Osborne Ln, Leonardtown, MD 20650
(443) 771-8009
$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
See all

Provided by Redfin

Sale history for 20507 Chestnut Ridge Dr

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$4,414 (+5.1%)

2024

$4,198 (+6.3%)

$135,900 + $288,600

$424,500

2023

$3,950 (+3.2%)

2022

$3,827 (+2.9%)

2021

$3,718 (+2.9%)

$135,900 + $226,100

$362,000

2020

$3,612 (+2.9%)

2019

$3,508

2018

$3,506 (+0.5%)

$125,900 + $204,100

$330,000

2017

$3,487 (+1.0%)

$125,900 + $204,100

$330,000

2015

$3,454 (−3.2%)

2014

$3,570 (+10.8%)

$130,900 + $208,000

$338,900

2013

$3,221 (+4.4%)

2012

$3,084 (+4.1%)

2011

$2,962

2010

$2,962 (+20.8%)

2009

$2,451

Tax history for 20507 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$4,414 (+5.1%)

2024

$4,198 (+6.3%)

$135,900 + $288,600

$424,500

2023

$3,950 (+3.2%)

2022

$3,827 (+2.9%)

2021

$3,718 (+2.9%)

$135,900 + $226,100

$362,000

2020

$3,612 (+2.9%)

2019

$3,508

2018

$3,506 (+0.5%)

$125,900 + $204,100

$330,000

2017

$3,487 (+1.0%)

$125,900 + $204,100

$330,000

2015

$3,454 (−3.2%)

2014

$3,570 (+10.8%)

$130,900 + $208,000

$338,900

2013

$3,221 (+4.4%)

2012

$3,084 (+4.1%)

2011

$2,962

2010

$2,962 (+20.8%)

2009

$2,451

*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

Stories

Lot width

—

Lot depth

—

Lot size

4.19 Acres

Year renovated

—

Sq. Ft.

2,555

Year built

1994

Style

Single Family Residential

County

St. Mary's County

APN

03 053458

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 Door Opener, Garage - Side Entry
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Garage
Attached Garage

Interior

Bedroom Information
# of Bedrooms On Main Level: 3

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

Interior Information
Appliances: Washer/Dryer Hookups Only
Interior Features: Attic, Combination Kitchen/Dining, Kitchen - Island, Upgraded Countertops, Window Treatments, Entry Level Bedroom, Master Bath(s), Wet/Dry Bar, Wood Floors

Room Information
Living Room, Dining Room, Master Bedroom, Bedroom 2, Kitchen, Game Room, Den, Bedroom 1, Utility Room

Fireplace Information
Has Fireplace
# of Fireplaces: 1

Basement Information
Basement: Yes
Connecting Stairway, Rear Entrance, Fully Finished, Walkout Level

Exterior

Property Information
Irrigation Water Rights
Improvement Assessed Value: $208,000
Ownership Interest: Fee Simple
Year Built Source: Estimated

Building Information
Construction Materials: Combination, Brick
Outdoor Living Structures: Deck(s), Porch(es)
Structure Type: Detached
Other Structures: Shed

Lot Information
Lot Features: Backs to Trees, Landscaping, No Thru Street
Tidal Water: No

Land Information
Land Assessed Value: $130,900

Financial

Tax Information
County Tax: $3,477.74
Tax Assessed Value: $338,900
Tax Year: 2011
Tax Annual Amount: $3,653.60

Assessments Information
Special Assessment Payment: Annually
Year Assessed: 2012

Utilities

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

Location

Homeowners Association Information
HOA Fee: $110
HOA Fee Frequency: Annually

Location Information
Directions: Rt 5 to Chestnut Ridge Dr, continue straight toward end of cul-de-sac, house on right. Sign in yard

Public facts

Beds: —
Baths: 3.0
Sq. Ft.: 2,555
Stories: 1.0
Lot Size: 4.19 acres
Style: Single Family Residential
Year Built: 1994
Year Renovated: —
County: St. Mary's County
APN: 03 053458

Home facts updated by county records on Oct 16, 2026

Around this home

Schools

Piney Point Elementary School

Public PreK-5 • Assigned • 4.9mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.6mi

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

$522,000 – $631,000

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New listings for sale in 20650

LISTED BY REDFIN3D WALKTHROUGH

$489,900

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— beds— baths1,542 sq ft

21944 Point Lookout Rd, Leonardtown, MD 20650

(443) 968-9595

COMING SOON

$467,000

3 beds2.5 baths1,568 sq ft

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(301) 884-9493

COMING SOON

$2,200,000

4 beds3 baths4,395 sq ft

22395 Newtowne Neck Rd, Leonardtown, MD 20650

(443) 975-7555

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4 beds3.5 baths3,264 sq ft

41427 Osborne Ln, Leonardtown, MD 20650

(443) 771-8009

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3 beds3.5 baths2,379 sq ft

41608 Briarwood Cir, Leonardtown, MD 20650

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COMING SOON

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5 beds3.5 baths4,271 sq ft

23603 Margrave Dr, Leonardtown, MD 20650

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4 beds4 baths3,750 sq ft

22220 Bull Rd, Leonardtown, MD 20650

(301) 855-8600

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3 beds1.5 baths1,218 sq ft

42163 Blacksmith Shop Rd, Leonardtown, MD 20650

(301) 862-2169

Home values near 20507 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20482 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2911 Sq. Ft.	$608,844
20520 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2329 Sq. Ft.	$628,963

Address	Redfin Estimate
20479 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2400 Sq. Ft.	$576,111
20500 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2694 Sq. Ft.	$588,037

Address	Redfin Estimate
20525 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3194 Sq. Ft.	$586,677
20496 Chestnut Ridge Dr, Leonardtown, MD 5 Beds \| 4.5 Baths \| 2945 Sq. Ft.	$630,594

Property information provided by BRIGHT MLS when last listed in 2012. 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 20507 Chestnut Ridge Dr

Tax history for 20507 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 20507 Chestnut Ridge Dr

More real estate resources