OFF MARKET

Off market feb 2024 for $550K

$662,916

Est. refi paymentEst. refi $4,469/mo

•

3,492

sq ft

20760 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Welcome to 20760 Chestnut Ridge Drive in sought after Leonardtown school district - a captivating 6-bedroom, 3.5-bathroom colonial on over 2 acres of wooded beauty! Nestled within a welcoming community, this property offers more than just a beautiful home—it provides a lifestyle enriched by the surrounding neighborhood. Picture yourself strolling through the scenic walking paths that wind through the community, where residents can be seen enjoying the great outdoors, socializing, and embracing a healthy, active lifestyle. This home is move in ready and features new carpet and paint that seamlessly complement the original kitchens and baths. Dual HVAC ensures year-round comfort and a newer propane water heater adds to the efficiency of this residence. The roof was replaced in 2015 with architectural shingles to ensure longevity. Wood floors on the mail level, interior storage in the basement and two full bedrooms as well as family room in the basement make this home highly functional for large families or those seeking a basement apartment with dedicated entrance or mother in law suite. Book your showing today!

Single-familyProperty Type

1993Year Built

2.32 acresLot Size

$190Est. Price/Sq.Ft.

2 car garageParking

Listed by Charlotte Long • EXP Realty, LLC

•888-860-7369 (broker)

•md.broker@exprealty.net (broker)

Bought with Sam Wentworth • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Redfin checked: 6 minutes ago

•Source:BRIGHT MLS #MDSM2016498

Redfin Estimate

$662,916

$113K since sold in February 2024$1,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.1% higher than the average sale price ($586K) of 5 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 MAY 11, 2026
$579,900
C
4 beds2.5 baths3,428 sq ft
43552 Bayberry Ct, Leonardtown, MD 20650
SOLD APR 14, 2026
$578,000
D
5 beds3.5 baths3,526 sq ft
21117 Catnip Ct, Leonardtown, MD 20650
SOLD SEP 16, 2026
$499,000
E
5 beds3.5 baths3,257 sq ft
44905 Widgeon Pl, Callaway, MD 20620

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

Earn from this home

Sell

$204,780

Est. take-home

List your home with Redfin and save $6,629

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,903/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 20760 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$5,249 (+7.5%)

2024

$4,884 (+9.0%)

$126,600 + $348,700

$475,300

2023

$4,482 (+6.1%)

2022

$4,225 (+3.9%)

2021

$4,068 (+4.0%)

$126,600 + $273,300

$399,900

2020

$3,910 (+4.2%)

2019

$3,753

2018

$3,751 (+0.5%)

$116,600 + $237,500

$354,100

2017

$3,732 (+0.9%)

$116,600 + $237,500

$354,100

2015

$3,698 (−7.1%)

$121,600 + $241,700

$363,300

2014

$3,982 (+3.6%)

$121,600 + $257,800

$379,400

2013

$3,844 (+5.1%)

2012

$3,657 (+2.7%)

2011

$3,561

2010

$3,561 (+19.8%)

2009

$2,971

Tax history for 20760 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$5,249 (+7.5%)

2024

$4,884 (+9.0%)

$126,600 + $348,700

$475,300

2023

$4,482 (+6.1%)

2022

$4,225 (+3.9%)

2021

$4,068 (+4.0%)

$126,600 + $273,300

$399,900

2020

$3,910 (+4.2%)

2019

$3,753

2018

$3,751 (+0.5%)

$116,600 + $237,500

$354,100

2017

$3,732 (+0.9%)

$116,600 + $237,500

$354,100

2015

$3,698 (−7.1%)

$121,600 + $241,700

$363,300

2014

$3,982 (+3.6%)

$121,600 + $257,800

$379,400

2013

$3,844 (+5.1%)

2012

$3,657 (+2.7%)

2011

$3,561

2010

$3,561 (+19.8%)

2009

$2,971

*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

Stories

Lot width

—

Lot depth

—

Lot size

2.32 Acres

Year renovated

—

Sq. Ft.

3,658

Year built

1993

Style

Single Family Residential

County

St. Mary's County

APN

03 048586

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
# 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
# of Bedrooms On 1st Lower Level: 2

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

Interior Information
Appliances: Dishwasher, Oven/Range - Gas, Oven - Wall, Refrigerator
Interior Features: Breakfast Area, Dining Area, Built-Ins, Upgraded Countertops, Master Bath(s), Wood Floors, WhirlPool/HotTub, Floor Plan - Traditional
Living Area Sq.Ft. Source: Assessor
Wall & Ceiling Types: Cathedral Ceilings

Room Information
Living Room, Dining Room, Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Game Room, Family Room, Den, Foyer, Breakfast Room, Study

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Mantel(s)

Basement Information
Basement: Yes
Other, Connecting Stairway, Daylight, Partial, Full, Heated, Interior Access, Rear Entrance, Walkout Level, Windows

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 1192
Improvement Assessed Value: $273,300
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Builder Name: GODWIN CONST.
Construction Materials: Vinyl Siding
Foundation Details: Slab
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Deck(s), Porch(es), Wrap Around
Roof: Asphalt
Structure Type: Detached

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

Land Information
Land Assessed Value: $126,600

Above Grade Information
Finished Sq.Ft.: 2,466
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft.: 166
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft.: 1,026
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
Agricultural Tax Due: No
County Tax: $4,079
Tax Assessed Value: $425,033
Tax Year: 2023
Tax Annual Amount: $4,079

Assessments Information
Special Assessment Payment: Annually
Year Assessed: 2023

Utilities

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

Location

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

Location Information
Outside City Limits
Directions: Route 5 South to right Chestnut Ridge
Municipality: LEONARDTOWN
Road Responsibility: City/County

Public facts

Beds: —
Baths: 3.0
Sq. Ft.: 3,658
Stories: 2.0
Lot Size: 2.32 acres
Style: Single Family Residential
Year Built: 1993
Year Renovated: —
County: St. Mary's County
APN: 03 048586

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 • 5.4mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.1mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 2.8mi

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

$630,000 – $763,000

Reach more buyers when you sell with Redfin. Save up to $6,629 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

Horse barn • Fruit trees • Raised garden

(301) 863-2400

$525,000

4 beds3.5 baths3,019 sq ft

22999 Ringtail Dr, California, MD 20619

Open floor plan • Hardwood floors • Formal dining room

(301) 862-2169

$1,050,000

3 beds2.5 baths5,939 sq ft

20098 Piney Point Rd, Callaway, MD 20620

1.49 acre backyard • True primary suite • Two walk-in closets

(240) 724-6550

$675,000

3 beds2 baths1,834 sq ft

18937 Hodges Ln, Leonardtown, MD 20650

Waterfront living • Open-concept kitchen • Stunning backyard

(301) 609-9000

$444,500

4 beds4 baths2,666 sq ft

20270 Beauvue Ct, Leonardtown, MD 20650

Level one-acre lot • Outdoor entertaining • Large family room

(301) 645-1700

$449,900

3 beds3 baths1,691 sq ft

43954 Main Way Rd, Leonardtown, MD 20650

Blacktop driveway • Oversized garage • Hardwood flooring

(410) 729-7700

New listings for sale in 20650

$369,000

3 beds2.5 baths1,092 sq ft

22231 Bayside Rd, Leonardtown, MD 20650

Brand new kitchen • New flooring • New hvac system

(855) 885-4663

$467,000

3 beds2.5 baths1,568 sq ft

22630 Quiet Ln, Leonardtown, MD 20650

1.27-acre lot • Attached garage • Paved spot for rv

(301) 884-9493

$399,999

2 beds1.5 baths1,056 sq ft

21784 Potomac View Dr, Leonardtown, MD 20650

Breton bay community • Community beach • New roof

(301) 862-2169

COMING SOON

$589,900

5 beds2.5 baths2,652 sq ft

21747 Potomac View Dr, Leonardtown, MD 20650

Large level backyard • Ceramic tile kitchen • Formal dining room

(301) 208-2288

$495,000

5 beds2.5 baths2,601 sq ft

40751 Merlin Way, Leonardtown, MD 20650

Brick front retreat • Private acres • New roof

(240) 993-9888

$585,000

5 beds3 baths2,666 sq ft

23591 Gunnell Dr, Leonardtown, MD 20650

Leonardtown location • Office flex room • Formal dining room

(410) 286-9632

$575,000

3 beds3.5 baths3,422 sq ft

22503 Sparrow Ct, Leonardtown, MD 20650

0.9 acre lot • 2 garage spots • Built 1990

(888) 860-7369

$2,200,000

4 beds3 baths4,395 sq ft

22395 Newtowne Neck Rd, Leonardtown, MD 20650

12807 acre farm • Charming rambler • 128.07 acre lot

(443) 975-7555

$549,000

4 beds3.5 baths3,006 sq ft

23208 Clarks Rest Rd, Leonardtown, MD 20650

7,150 sq ft lot • 2 garage spots • Community pool

(443) 771-8009

Home values near 20760 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20829 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3.5 Baths \| 3683 Sq. Ft.	$572,873
20735 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3 Baths \| 2568 Sq. Ft.	$598,433
20804 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3582 Sq. Ft.	$647,191
20820 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2416 Sq. Ft.	$504,690
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
43310 Gum Spring Dr, Leonardtown, MD 5 Beds \| 4 Baths \| 4636 Sq. Ft.	$732,733

Address	Redfin Estimate
20784 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3 Baths \| 2802 Sq. Ft.	$590,835
20753 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2594 Sq. Ft.	$599,648
20854 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3 Baths \| 2498 Sq. Ft.	$589,124
20787 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2602 Sq. Ft.	$555,039
20644 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 5104 Sq. Ft.	$610,618
20740 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3 Baths \| 3572 Sq. Ft.	$655,172
43330 Gum Spring Dr, Leonardtown, MD 3 Beds \| 2 Baths \| 2300 Sq. Ft.	$528,107

Address	Redfin Estimate
20776 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2606 Sq. Ft.	$547,073
20800 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 3320 Sq. Ft.	$662,601
20815 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2 Baths \| 1620 Sq. Ft.	$513,620
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
43290 Gum Spring Dr, Leonardtown, MD 5 Beds \| 3.5 Baths \| 3016 Sq. Ft.	$523,101
43285 Gum Spring Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2146 Sq. Ft.	$492,714

Property information provided by BRIGHT MLS when last listed in 2024. 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.

Redfin Brokerage Licenses

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	Frederick, MD homes for sale	Leonardtown Housing Market
Houses for sale near me	Baltimore, MD homes for sale	Rockville, 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
Mechanicsville homes for sale
Colonial Beach homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Sale history for 20760 Chestnut Ridge Dr

Tax history for 20760 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 20760 Chestnut Ridge Dr

More real estate resources