SOLD OCT 30, 2025

Off market oct 2025 for $599K

$630,901

Est. refi paymentEst. refi $4,729/mo

•

3,061

sq ft

20591 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Welcome to this well-built colonial on a corner lot in the picturesque corner Chestnut Ridge neighborhood! With over 3,000 finished square feet, 5 bedrooms, and 3.5 bathrooms, this home is full of charm, character, and thoughtful craftsmanship. Situated on 2.11 acres, the home features a classic brick exterior, a welcoming front porch, and a spacious two-car garage. Inside on the main level, you'll find two comfortable living areas, a dedicated dining space, and a kitchen with granite countertops, stainless steel appliances, and plenty of room to make it your own. Step right out onto the back deck to enjoy the peaceful, private outdoor setting. All five bedrooms are located on the second and third floors, offering privacy and space for everyone. The rooms are generously sized, including a spacious primary suite and a versatile bonus room above the garage—perfect for a home office, playroom, or guest retreat. The unfinished basement adds even more flexibility, offering excellent storage or future expansion potential. New Roof in 2018. New Sump Pump 2025. Enjoy the quiet setting, timeless design, and endless potential Chestnut Ridge gem offers—ready for its next chapter. Don’t miss your chance to own a home with this much space, land, and value—schedule your private showing today! Back on the market, due to buyer not meeting home sale contingency

Single-familyProperty Type

1995Year Built

2.11 acresLot Size

$206Est. Price/Sq.Ft.

2 car garageParking

Listed by Lauren Garner • EXP Realty, LLC

•888-860-7369 (broker)

•md.broker@exprealty.net (broker)

Bought with Matt Burgan • Infinitas Realty Group

•240-925-2224 (broker)

•matt@infinitasrealty.com (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDSM2025274

Redfin Estimate

$630,901

$31K since sold in October 2025$8,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 7.7% 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 MAR 5, 2026
$575,000
C
5 beds3.5 baths3,075 sq ft
21060 Woodmere Dr, Leonardtown, MD 20650
SOLD SEP 16, 2026
$499,000
D
5 beds3.5 baths3,257 sq ft
44905 Widgeon Pl, Callaway, MD 20620
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

$120,603

Est. take-home

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Refinance

Est. cash available

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Rent

$3,113/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

NEW 3 HRS AGO
$299,500
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42163 Blacksmith Shop Rd, Leonardtown, MD 20650
(301) 862-2169
$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
$475,000
4 beds2.5 baths2,200 sq ft
43261 Cedarwood Ct, Leonardtown, MD 20650
(888) 860-7369
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 20591 Chestnut Ridge Dr

Date

Event

Price

BRIGHT MLS #MDSM2025274

Oct 30, 2025

Sold

$599,900

$196/sq ft

Sep 30, 2025

Contingent

—

Sep 16, 2025

Price Changed

$599,900

$196/sq ft

Aug 22, 2025

Relisted

—

Jul 10, 2025

Contingent

—

Jun 28, 2025

Listed

$615,000

$201/sq ft

Jun 3, 2025

Coming Soon

$615,000

$201/sq ft

BRIGHT MLS #MDSM2000808

Aug 3, 2021

Sold

$535,000

$175/sq ft

Jul 21, 2021

Pending

—

Jul 21, 2021

Listed

$535,000

$175/sq ft

BRIGHT MLS #1005212638

Jun 12, 2009

Sold

$425,000

$139/sq ft

May 15, 2009

Listing Removed

—

Mar 13, 2009

Listed

$439,000

$143/sq ft

+25

Public Records

Oct 21, 1992

Sold

$42,000

$14/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$5,807 (+10.9%)

2024

$5,238 (+12.9%)

$125,500 + $401,900

$527,400

2023

$4,638 (+10.6%)

2022

$4,194 (+5.9%)

2021

$3,960 (+3.0%)

$125,500 + $271,400

$396,900

2020

$3,843 (+3.1%)

2019

$3,729

2018

$3,727 (+0.5%)

$115,500 + $236,200

$351,700

2017

$3,708 (+1.0%)

$115,500 + $236,200

$351,700

2015

$3,673 (−5.1%)

$120,500 + $240,400

$360,900

2014

$3,872

$120,500 + $248,100

$368,600

2013

$3,872 (+0.8%)

2012

$3,842 (−11.3%)

2011

$4,332

2010

$4,332 (+15.6%)

2009

$3,747

Tax history for 20591 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$5,807 (+10.9%)

2024

$5,238 (+12.9%)

$125,500 + $401,900

$527,400

2023

$4,638 (+10.6%)

2022

$4,194 (+5.9%)

2021

$3,960 (+3.0%)

$125,500 + $271,400

$396,900

2020

$3,843 (+3.1%)

2019

$3,729

2018

$3,727 (+0.5%)

$115,500 + $236,200

$351,700

2017

$3,708 (+1.0%)

$115,500 + $236,200

$351,700

2015

$3,673 (−5.1%)

$120,500 + $240,400

$360,900

2014

$3,872

$120,500 + $248,100

$368,600

2013

$3,872 (+0.8%)

2012

$3,842 (−11.3%)

2011

$4,332

2010

$4,332 (+15.6%)

2009

$3,747

*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

3.5

Stories

2.5

Lot width

—

Lot depth

—

Lot size

2.11 Acres

Year renovated

—

Sq. Ft.

3,061

Year built

1995

Style

Single Family Residential

County

St. Mary's County

APN

03 052974

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, Garage - Side Entry, Inside Access
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Paved Driveway
Driveway, 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 All Upper Levels: 3
# of Bathrooms (Half): 1
# of Bathrooms (Full): 3

Interior Information
Appliances: Cooktop, Dishwasher, Dryer, Exhaust Fan, Icemaker, Oven - Wall, Refrigerator, Washer
Interior Features: Upgraded Countertops, Wood Floors, Carpet, Tub Shower, Walk-in Closet(s), Soaking Tub, Stall Shower, Pantry, CeilngFan(s), Combination Kitchen/Dining, Dining Area, Kitchen - Gourmet, Master Bath(s)
Living Area Sq.Ft. Source: Assessor
Wall & Ceiling Types: Dry Wall

Room Information
Living Room, Dining Room, Master Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Basement, Foyer, Laundry, Master Bathroom, Full Bath, Half Bath
Laundry Type: Dryer In Unit, Washer In Unit, Upper Floor, Hookup, Lower Floor

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Wood

Basement Information
Basement: Yes
Full, Interior Access, Side Entrance, Unfinished, Walkout Level

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $271,400
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Brick Front, Vinyl Siding
Foundation Details: Concrete Perimeter
Other Structures: Above Grade, Below Grade
Outdoor Living Structures: Patio(s), Deck(s)
Pets Allowed: Yes
Pet Restrictions: No Pet Restrictions
Roof: Shingle
Structure Type: Detached
Window Features: Bay/Bow, Screens, Skylights
Other Structures: Shed

Exterior Information
Secure Storage

Lot Information
Lot Features: Backs to Trees, Front Yard, Level, Rear Yard, SideYard(s), Trees/Wooded
Tidal Water: No

Land Information
Land Assessed Value: $125,500

Above Grade Information
Unfinished Sq.Ft.: 276
Unfinished Sq.Ft. Source: Estimated
Finished Sq.Ft.: 3,061
Finished Sq.Ft. Source: Assessor

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

Financial

Tax Information
Agricultural Tax Due: No
County Tax: $3,520
Tax Assessed Value: $396,900
Tax Year: 2020
Tax Annual Amount: $3,880

Assessments Information
Special Assessment Payment: Annually
Year Assessed: 2021

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: Propane
Sewer Septic: Private Septic Tank
Cable TV Available
Water Source: Well

Location

Homeowners Association Information
HOA Fee: $100
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: Listing Agent
Middle School Source: Listing Agent
High School Source: Listing Agent
School District Source: Listing Agent

Location Information
Outside City Limits
Directions: GPS is correct
Municipality: Unincorporated
Road Surface Type: Black Top

Public facts

Beds: —
Baths: 3.5
Sq. Ft.: 3,061
Stories: 2.5
Lot Size: 2.11 acres
Style: Single Family Residential
Year Built: 1995
Year Renovated: —
County: St. Mary's County
APN: 03 052974

Home facts updated by county records on Jul 18, 2026

Around this home

Schools

Piney Point Elementary School

Public PreK-5 • Assigned • 5.1mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.3mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 3.0mi

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

$600,000 – $726,000

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New listings for sale in 20650

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42163 Blacksmith Shop Rd, Leonardtown, MD 20650

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COMING SOON

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COMING SOON

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Home values near 20591 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20525 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 3 Baths \| 3194 Sq. Ft.	$582,926
20550 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 2742 Sq. Ft.	$605,367

Address	Redfin Estimate
20520 Chestnut Ridge Drive, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2329 Sq. Ft.	$618,705
20511 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 3.5 Baths \| 4448 Sq. Ft.	$668,587

Address	Redfin Estimate
20500 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 3 Baths \| 2694 Sq. Ft.	$583,890
20535 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 3 Baths \| 3165 Sq. Ft.	$567,872

Property information provided by BRIGHT MLS when last listed in 2025. 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 20591 Chestnut Ridge Dr

Tax history for 20591 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 20591 Chestnut Ridge Dr

More real estate resources