OFF MARKET

Off market nov 2020 for $510K

$678,294

Est. refi paymentEst. refi $3,344/mo

•

2,785

sq ft

20576 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Stunning, large custom-built rambler on 5.7 acres in the desirable Chestnut Ridge subdivision. Enjoy the serenity of a nice-size yard with lots of privacy on a wooded lot. This nearly 2,800 square-foot home features three bedrooms and 2.5 bathrooms. House has a great layout. From your elegant foyer, the study/office is on your left with built-in bookcases. On your right, the formal living room and dining room have lots of natural light and beautiful hardwood floors. The kitchen is very functional with a huge breakfast nook and lots of counter space. Kitchen opens to an inviting family room with a stone-faced wood burning fireplace. Master bedroom suite has its own sunroom/sitting area with walk-out French doors and two large walk-in closets. Luxurious master bathroom with double sinks, deep jacuzzi tub, separate shower and a bidet. The other two spacious bedrooms both have nice-sized closets with double doors. You will fall in love with the outdoors. There is a large composite deck (two tiers) off the master BR and an elevated brick paver patio coming off the kitchen side door, plus another brick paver area for grilling. Property comes with two out-buildings, both 12x20. One building is a storage shed with a concrete floor and the other is insulated and finished with paneling, painted ceiling, and electric power with a dual-purpose heating/cooling unit to use as a workshop, exercise or craft room. The attached two-car garage is finished and insulated with epoxy painted floors, gladiator mounting channels and a deep sink. This very well kept house also features a geothermal HVAC system installed in 2016 with a wi-fi thermostat. House is wired for emergency back-up power with a portable 7500 watt generator that conveys. Roof was re-shingled in 2011. All Andersen windows (except Living room and sky-lights). A house like this doesn?t come on the market very often, schedule your showing today!

Single-familyProperty Type

1994Year Built

5.77 acresLot Size

$244Est. Price/Sq.Ft.

2 car garageParking

Listed by Gabriela Montgomery • RE/MAX 100

•301-863-5355 (broker)

Bought with Nancy Immel • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Redfin checked: 3 minutes ago

•Source:BRIGHT MLS #MDSM172196

Redfin Estimate

$678,294

$168K since sold in November 2020$3,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.5% higher than the average sale price ($619K) of 5 comparable homes.

SOLD SEP 18, 2026
$605,000
A
3 beds2.5 baths2,052 sq ft
20980 Aster Dr, Callaway, MD 20620
SOLD NOV 26, 2025
$625,000
B
3 beds2.5 baths2,742 sq ft
43107 Gum Spring 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 MAR 5, 2026
$560,000
D
4 beds2.5 baths2,594 sq ft
20753 Chestnut Ridge Dr, 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

$277,275

Est. take-home

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Refinance

Est. cash available

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Rent

$2,602/mo

Redfin rental estimate

List your home for rent

Market trends in 20650, MD

Last updated October 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

$369,000
3 beds2.5 baths1,092 sq ft
22231 Bayside Rd, Leonardtown, MD 20650
(855) 885-4663
$467,000
3 beds2.5 baths1,568 sq ft
22630 Quiet Ln, Leonardtown, MD 20650
(301) 884-9493
$399,999
2 beds1.5 baths1,056 sq ft
21784 Potomac View Dr, Leonardtown, MD 20650
(301) 862-2169
COMING SOON
$589,900
5 beds2.5 baths2,652 sq ft
21747 Potomac View Dr, Leonardtown, MD 20650
(301) 208-2288
$495,000
5 beds2.5 baths2,601 sq ft
40751 Merlin Way, Leonardtown, MD 20650
(240) 993-9888
$585,000
5 beds3 baths2,666 sq ft
23591 Gunnell Dr, Leonardtown, MD 20650
(410) 286-9632
$575,000
3 beds3.5 baths3,422 sq ft
22503 Sparrow Ct, Leonardtown, MD 20650
(888) 860-7369
$2,200,000
4 beds3 baths4,395 sq ft
22395 Newtowne Neck Rd, Leonardtown, MD 20650
(443) 975-7555
$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 20576 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$5,599 (+12.1%)

2024

$4,997 (+14.4%)

$141,900 + $366,100

$508,000

2023

$4,369 (+12.4%)

2022

$3,888

2021

$3,886

$141,900 + $224,900

$366,800

2020

$3,884

$141,900 + $224,900

$366,800

2019

$3,888 (+0.5%)

$141,900 + $224,900

$366,800

2018

$3,866 (+1.0%)

2017

$3,828 (+12.0%)

2015

$3,418 (+100.7%)

2014

$1,703 (−48.3%)

$136,900 + $186,000

$322,900

2013

$3,294 (+5.2%)

2012

$3,130 (+2.5%)

2011

$3,053

2010

$3,053 (+20.6%)

2009

$2,532

Tax history for 20576 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$5,599 (+12.1%)

2024

$4,997 (+14.4%)

$141,900 + $366,100

$508,000

2023

$4,369 (+12.4%)

2022

$3,888

2021

$3,886

$141,900 + $224,900

$366,800

2020

$3,884

$141,900 + $224,900

$366,800

2019

$3,888 (+0.5%)

$141,900 + $224,900

$366,800

2018

$3,866 (+1.0%)

2017

$3,828 (+12.0%)

2015

$3,418 (+100.7%)

2014

$1,703 (−48.3%)

$136,900 + $186,000

$322,900

2013

$3,294 (+5.2%)

2012

$3,130 (+2.5%)

2011

$3,053

2010

$3,053 (+20.6%)

2009

$2,532

*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

5.77 Acres

Year renovated

—

Sq. Ft.

2,688

Year built

1994

Style

Single Family Residential

County

St. Mary's County

APN

03 053008

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 16, 2026.

Jun 7, 2008 • Final

Bldg new construction

Amend the existing permit to include the construction of an additional deck.

Addition

Remodel

Jun 8, 2007 • Active

Residential addition

Expand the master bedroom, family room, and decks.

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
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Asphalt Driveway
Attached Garage, Driveway

Interior

Virtual Tour

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Half): 1
# of Bathrooms (Full): 2

Interior Information
Appliances: Dishwasher, Cooktop, Oven - Double, Refrigerator, Washer/Dryer Hookups Only
Not Furnished
Interior Features: Breakfast Area, Dining Area, Entry Level Bedroom, Formal/Separate Dining Room, Carpet, Soaking Tub, Store/Office, Walk-in Closet(s), Built-Ins, CeilngFan(s), Family Room Off Kitchen, Kitchen - Eat-In, Skylight(s), Wood Floors
Living Area Sq.Ft. Source: Estimated

Room Information
Laundry Type: Main Floor

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Wood

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $235,400
Ownership Interest: Fee Simple
Property Condition: Excellent
Year Built Source: Assessor

Building Information
Construction Materials: Aluminum Siding
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Patio(s)
Roof: Composite, Shingle
Structure Type: Detached
Other Structures: Shed, Shed Shop

Exterior Information
Outbuilding(s), Water Fountains, Other

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

Land Information
Land Assessed Value: $131,900

Above Grade Information
Finished Sq.Ft.: 2,785
Finished Sq.Ft. Source: Estimated

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

Financial

Tax Information
County Tax: $3,520
Tax Assessed Value: $366,800
Tax Year: 2020
Tax Annual Amount: $3,880

Assessments Information
Year Assessed: 2020

Utilities

Utilities Information
Cooling Type: Geothermal, Heat Pump(s)
Cooling Fuel: Electric, Geothermal
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Septic Exists
Water Source: Well
Municipal Trash: No

Location

Homeowners Association Information
HOA Fee: $112
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
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: From 235/Three Notch Rd, drive onto Route 4; From Route 4, turn left onto Route 5; From Route 5, turn right onto Chestnut Ridge Dr

Public facts

Beds: —
Baths: 2.5
Sq. Ft.: 2,688
Stories: 1.0
Lot Size: 5.77 acres
Style: Single Family Residential
Year Built: 1994
Year Renovated: —
County: St. Mary's County
APN: 03 053008

Home facts updated by county records on Oct 16, 2026

Around this home

Schools

K - 12
Preschool & daycare

Piney Point Elementary School

Public PreK-5 • Assigned • 5.1mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.4mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 3.1mi

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

$645,000 – $781,000

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Home values near 20576 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20525 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3194 Sq. Ft.	$598,704
20496 Chestnut Ridge Dr, Leonardtown, MD 5 Beds \| 4.5 Baths \| 2945 Sq. Ft.	$643,011
20484 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 1744 Sq. Ft.	$480,676
20590 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2846 Sq. Ft.	$601,688
20591 Chestnut Ridge Dr, Leonardtown, MD 5 Beds \| 3.5 Baths \| 3061 Sq. Ft.	$632,515
20708 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2580 Sq. Ft.	$613,344
20714 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2768 Sq. Ft.	$531,432

Address	Redfin Estimate
20520 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2329 Sq. Ft.	$625,118
20490 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3.5 Baths \| 2536 Sq. Ft.	$594,288
20511 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3.5 Baths \| 4448 Sq. Ft.	$682,336
20572 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3.5 Baths \| 3840 Sq. Ft.	$683,535
20610 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 2.5 Baths \| 3021 Sq. Ft.	$685,017
20644 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 5104 Sq. Ft.	$610,618
43298 Oakway Ct, Leonardtown, MD - Beds \| 2.5 Baths \| 1950 Sq. Ft.	$512,094

Address	Redfin Estimate
20500 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2694 Sq. Ft.	$581,955
20550 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2742 Sq. Ft.	$611,547
20535 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3165 Sq. Ft.	$584,988
20565 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3406 Sq. Ft.	$609,354
20676 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 1792 Sq. Ft.	$513,757
20704 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3.5 Baths \| 3642 Sq. Ft.	$445,311
43261 Oakway Ct, Leonardtown, MD - Beds \| 3 Baths \| 3288 Sq. Ft.	$645,486

Property information provided by BRIGHT MLS when last listed in 2020. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Sale history for 20576 Chestnut Ridge Dr

Tax history for 20576 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 20576 Chestnut Ridge Dr

More real estate resources