OFF MARKET

Off market aug 2024 for $599K

$655,172

Est. refi paymentEst. refi $4,165/mo

•

3,572

sq ft

20740 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Welcome to your dream home in a highly sought-after Chestnut Ridge subdivision! This wonderful colonial boasts of 4 bedrooms and 2 full baths with additional powder room, perfectly situated on over 2 acres of meticulously manicured grounds with a charming garden area, spacious shed , sheltered wood storage, and a serene wooded backdrop. Spanning over 3500 square feet, this home offers ample space and comfort. Step inside to discover a newly painted interior with fresh carpet throughout, creating a bright and inviting atmosphere. The open floor plan seamlessly connects the living areas, highlighted by a cozy fireplace in the family room, ideal for gatherings and relaxation. Upstairs, three spacious bedrooms feature custom closets, another full bathroom, plus the primary suite recently updated bath with a new shower and a generous custom closet. The lower level offers flexible space for a recreation room, home office, or workout area, accommodating various lifestyle needs. Bonus! The unfinished room located above the garage allows you the freedom to design and finish the space according to your preferences and lifestyle or will give you an abundance of storage. Whole home water filtration system plus advanced Rain Bird irragation system! Priced competitively- Don't miss out!!

Single-familyProperty Type

1991Year Built

2.27 acresLot Size

$183Est. Price/Sq.Ft.

2 car garageParking

Listed by Tracey Summers • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Bought with Amy Scott • OE Realty

•240-484-8887 (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDSM2019776

Redfin Estimate

$655,172

$55K since sold in August 2024$7,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.9% lower than the average sale price ($703K) 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 MAY 11, 2026
$579,900
B
4 beds2.5 baths3,428 sq ft
43552 Bayberry Ct, 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 AUG 31, 2026
$976,000
E
4 beds2.5 baths2,550 sq ft
41402 Philip Ln, Leonardtown, MD 20650

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Earn from this home

Sell

$154,480

Est. take-home

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Refinance

Est. cash available

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Rent

$2,801/mo

Redfin rental estimate

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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 20740 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$5,245 (+15.8%)

2024

$4,528 (+6.5%)

$126,300 + $348,600

$474,900

2023

$4,253 (+3.4%)

2022

$4,114 (+2.2%)

2021

$4,024 (+2.3%)

$126,300 + $262,700

$389,000

2020

$3,934 (+2.3%)

2019

$3,845

2018

$3,843 (+0.5%)

$116,300 + $246,800

$363,100

2017

$3,824 (+0.8%)

$116,300 + $246,800

$363,100

2015

$3,794 (−4.8%)

$121,300 + $251,400

$372,700

2014

$3,984

$121,300 + $258,300

$379,600

2013

$3,984 (+0.8%)

2012

$3,954 (+2.2%)

2011

$3,870

2010

$3,870 (+18.9%)

2009

$3,256

Tax history for 20740 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$5,245 (+15.8%)

2024

$4,528 (+6.5%)

$126,300 + $348,600

$474,900

2023

$4,253 (+3.4%)

2022

$4,114 (+2.2%)

2021

$4,024 (+2.3%)

$126,300 + $262,700

$389,000

2020

$3,934 (+2.3%)

2019

$3,845

2018

$3,843 (+0.5%)

$116,300 + $246,800

$363,100

2017

$3,824 (+0.8%)

$116,300 + $246,800

$363,100

2015

$3,794 (−4.8%)

$121,300 + $251,400

$372,700

2014

$3,984

$121,300 + $258,300

$379,600

2013

$3,984 (+0.8%)

2012

$3,954 (+2.2%)

2011

$3,870

2010

$3,870 (+18.9%)

2009

$3,256

*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

2.27 Acres

Year renovated

—

Sq. Ft.

3,917

Year built

1991

Style

Single Family Residential

County

St. Mary's County

APN

03 048594

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

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 4

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

Interior Information
Living Area Sq.Ft. Source: Assessor

Fireplace Information
Has Fireplace
# of Fireplaces: 1

Basement Information
Basement: Yes
Full, Partially Finished

Exterior

Property Information
Total Below Grade Sq. Ft.: 1170
Improvement Assessed Value: $348,600
Ownership Interest: Fee Simple
Year Built Source: Assessor

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

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $126,300

Above Grade Information
Finished Sq.Ft.: 2,922
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft.: 520
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft.: 650
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $4,008
Tax Assessed Value: $446,267
Tax Year: 2024
Tax Annual Amount: $4,008

Assessments Information
Year Assessed: 2024

Utilities

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

Location

Homeowners Association Information
HOA Fee: $359
HOA Fee Frequency: Annually

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

Location Information
Outside City Limits
Directions: Route 5 to Chestnut Ridge Home on Left

Public facts

Beds: —
Baths: 3.0
Sq. Ft.: 3,917
Stories: 2.0
Lot Size: 2.27 acres
Style: Single Family Residential
Year Built: 1991
Year Renovated: —
County: St. Mary's County
APN: 03 048594

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 • 5.3mi

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

$623,000 – $754,000

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New listings for sale in 20650

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Home values near 20740 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20829 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3.5 Baths \| 3683 Sq. Ft.	$572,873
20735 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3 Baths \| 2568 Sq. Ft.	$598,433
20804 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 3 Baths \| 3582 Sq. Ft.	$647,191
20820 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 2416 Sq. Ft.	$504,690
20708 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 2580 Sq. Ft.	$613,344
20714 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 2768 Sq. Ft.	$531,432
43310 Gum Spring Drive, Leonardtown, MD 5 Beds \| 4 Baths \| 4636 Sq. Ft.	$732,733

Address	Redfin Estimate
20784 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3 Baths \| 2802 Sq. Ft.	$590,835
20753 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2594 Sq. Ft.	$599,648
20854 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3 Baths \| 2498 Sq. Ft.	$589,124
20787 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 2602 Sq. Ft.	$555,039
20644 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 5104 Sq. Ft.	$610,618
20760 Chestnut Ridge Drive, Leonardtown, MD 6 Beds \| 3.5 Baths \| 3492 Sq. Ft.	$662,916
43330 Gum Spring Drive, Leonardtown, MD 3 Beds \| 2 Baths \| 2300 Sq. Ft.	$528,107

Address	Redfin Estimate
20776 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2606 Sq. Ft.	$547,073
20800 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 3320 Sq. Ft.	$662,601
20815 Chestnut Ridge Drive, Leonardtown, MD 3 Beds \| 2 Baths \| 1620 Sq. Ft.	$513,620
20676 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 1792 Sq. Ft.	$513,757
20704 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3.5 Baths \| 3642 Sq. Ft.	$445,311
43290 Gum Spring Drive, Leonardtown, MD 5 Beds \| 3.5 Baths \| 3016 Sq. Ft.	$523,101
43285 Gum Spring Drive, 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.

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About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Sale history for 20740 Chestnut Ridge Dr

Tax history for 20740 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 20740 Chestnut Ridge Dr

More real estate resources