OFF MARKET

Off market sep 2017 for $410K

$622,451

Est. refi paymentEst. refi $2,782/mo

•

2,945

sq ft

20496 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

4 story Colonial in quiet neighborhood features 5 bedrooms and 4 1/2 baths. This home features a fully finished basement with full bath, rec room and wet bar. Main level has formal dining and living rooms, family room and kitchen. 2nd level features 3 bedrooms with 2 full baths, 3rd level features 2 bedrooms and full bath. Additional features include oak hardwood, deck, patio and attached garage.

Single-familyProperty Type

1993Year Built

2.4 acresLot Size

$211Est. Price/Sq.Ft.

2 car garageParking

Listed by Jan Barnes • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Bought with Jennifer Goddard • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #1000191157

Redfin Estimate

$622,451

$212K since sold in September 2017$2,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.6% lower than the average sale price ($626K) of 6 comparable homes.

SOLD SEP 8, 2026
$674,000
A
4 beds3.5 baths3,381 sq ft
20750 Deer Wood Park Dr, Leonardtown, MD 20650
SOLD JUN 24, 2026
$600,000
B
5 beds3.5 baths3,090 sq ft
22055 Long Bow Dr, California, MD 20619
SOLD OCT 30, 2025
$599,900
C
5 beds3.5 baths3,061 sq ft
20591 Chestnut Ridge Dr, Leonardtown, MD 20650
SOLD MAY 14, 2026
$727,360
D
4 beds2.5 baths2,972 sq ft
43500 Deer Run Ct, Leonardtown, MD 20650
SOLD MAY 11, 2026
$579,900
E
4 beds2.5 baths3,428 sq ft
43552 Bayberry Ct, Leonardtown, MD 20650
SOLD MAR 5, 2026
$575,000
F
5 beds3.5 baths3,075 sq ft
21060 Woodmere Dr, Leonardtown, MD 20650

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Earn from this home

Sell

$318,638

Est. take-home

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Refinance

Est. cash available

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Rent

$2,903/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

100.7%

+0.6% MoM

Median sale price

$535K

$30K MoM

Avg. days on market

49d

5 days MoM

Recently sold homes

15 MoM

New listings for sale

OPEN SAT, 10AM TO 2PM
$475,000
3 beds2 baths1,462 sq ft
43705 Redmond Rd, Leonardtown, MD 20650
(301) 609-9000
OPEN SAT, 12PM TO 2PM
$515,000
4 beds3.5 baths2,764 sq ft
22538 Landing Way, Leonardtown, MD 20650
(443) 771-8009
$475,000
4 beds2.5 baths2,200 sq ft
43261 Cedarwood Ct, Leonardtown, MD 20650
(888) 860-7369
$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
$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
See all

Provided by Redfin

Sale history for 20496 Chestnut Ridge Dr

** Price available after signing in.

Year

Property tax

Land + Additions

Assessment*

2025

$4,549 (+5.4%)

2024

$4,315 (+6.6%)

$127,000 + $353,000

$480,000

2023

$4,047 (+6.7%)

2021

$3,793 (+3.0%)

$127,000 + $250,500

$377,500

2020

$3,682 (+3.0%)

2019

$3,573

2018

$3,572 (+0.5%)

$117,000 + $219,400

$336,400

2017

$3,553 (+1.1%)

$117,000 + $219,400

$336,400

2015

$3,515 (+7.1%)

$122,000 + $223,300

$345,300

2014

$3,282 (+4.2%)

$122,000 + $224,200

$346,200

2013

$3,150 (+5.2%)

2012

$2,994 (+4.0%)

2011

$2,878

2010

$2,878 (+20.9%)

2009

$2,380

Tax history for 20496 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$4,549 (+5.4%)

2024

$4,315 (+6.6%)

$127,000 + $353,000

$480,000

2023

$4,047 (+6.7%)

2021

$3,793 (+3.0%)

$127,000 + $250,500

$377,500

2020

$3,682 (+3.0%)

2019

$3,573

2018

$3,572 (+0.5%)

$117,000 + $219,400

$336,400

2017

$3,553 (+1.1%)

$117,000 + $219,400

$336,400

2015

$3,515 (+7.1%)

$122,000 + $223,300

$345,300

2014

$3,282 (+4.2%)

$122,000 + $224,200

$346,200

2013

$3,150 (+5.2%)

2012

$2,994 (+4.0%)

2011

$2,878

2010

$2,878 (+20.9%)

2009

$2,380

*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

4.5

Stories

2.5

Lot width

—

Lot depth

—

Lot size

2.4 Acres

Year renovated

—

Sq. Ft.

3,205

Year built

1993

Style

Single Family Residential

County

St. Mary's County

APN

03 053555

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 18, 2026.

Property details

Parking

Parking Information
# of Attached Garage Spaces: 2
Garage Features: Garage Door Opener
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Garage
Attached Garage

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 3
# of Bedrooms On 2nd Upper Level: 2

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 2
# of Bathrooms (Full) On 2nd Upper Level: 1
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On 1st Lower Level: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 4

Interior Information
Appliances: Microwave, Dryer, Washer, Cooktop, Dishwasher, Exhaust Fan, Disposal, Refrigerator, Oven - Wall
Interior Features: Dining Area, Window Treatments
Living Area Sq.Ft. Source: Estimated

Fireplace Information
Has Fireplace
# of Fireplaces: 1

Basement Information
Basement: Yes
Outside Entrance, Connecting Stairway, Fully Finished

Exterior

Property Information
Total Below Grade Sq. Ft.: 500
Improvement Assessed Value: $219,400
Ownership Interest: Fee Simple
Year Built Source: Estimated

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

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $117,000

Above Grade Information
Finished Sq.Ft.: 2,445
Finished Sq.Ft. Source: Estimated

Below Grade Information
Finished Sq.Ft.: 500
Finished Sq.Ft. Source: Estimated

Financial

Tax Information
County Tax: $3,329.73
Tax Assessed Value: $336,400
Tax Year: 2016
Tax Annual Amount: $3,526.55

Assessments Information
Special Assessment Payment: Annually
Year Assessed: 2017

Utilities

Utilities Information
Cooling Type: Heat Pump(s)
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric, Bottled Gas/Propane
Hot Water: Electric
Sewer Septic: Septic Exists
Water Source: Well

Location

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

School Information
Elementary School: PINEY POINT
Middle Or Junior School: LEONARDTOWN
High School: LEONARDTOWN
School District Name: ST. MARY'S COUNTY PUBLIC SCHOOLS

Location Information
Directions: RT 235 N, Left onto St Andrews Church Rd, Left onto Point Lookout Rd, Right onto Chestnut Ridge Dr. House is on the left.

Public facts

Beds: —
Baths: 4.5
Sq. Ft.: 3,205
Stories: 2.5
Lot Size: 2.4 acres
Style: Single Family Residential
Year Built: 1993
Year Renovated: —
County: St. Mary's County
APN: 03 053555

Home facts updated by county records on Jul 18, 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

$592,000 – $716,000

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Nearby similar homes

$929,900

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OPEN SUN, 11AM TO 1PM

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3 beds2.5 baths1,668 sq ft

22435 Indian Bridge Rd, California, MD 20619

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New listings for sale in 20650

OPEN SAT, 10AM TO 2PM

$475,000

3 beds2 baths1,462 sq ft

43705 Redmond Rd, Leonardtown, MD 20650

(301) 609-9000

OPEN SAT, 12PM TO 2PM

$515,000

4 beds3.5 baths2,764 sq ft

22538 Landing Way, Leonardtown, MD 20650

(443) 771-8009

$475,000

4 beds2.5 baths2,200 sq ft

43261 Cedarwood Ct, Leonardtown, MD 20650

(888) 860-7369

$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

$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

Home values near 20496 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
20520 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2329 Sq. Ft.	$618,705

Address	Redfin Estimate
20507 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 3 Baths \| 1705 Sq. Ft.	$546,949
20500 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2694 Sq. Ft.	$583,890

Property information provided by BRIGHT MLS when last listed in 2017. 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 20496 Chestnut Ridge Dr

Tax history for 20496 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 20496 Chestnut Ridge Dr

More real estate resources