Google satellite image for 20644 Chestnut Ridge Dr, Leonardtown, MD 20650

Off market

$610,618

—

•

2.5 ba

•

5,104

sq ft

20644 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

20644 Chestnut Ridge Dr is a 5,104 square foot house on a 2.19 acre lot with 2.5 bathrooms. Based on Redfin's Leonardtown data, we estimate the home's value is $610,618.

Single-familyProperty Type

1991Year Built

2.19 acresLot Size

$120Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$610,618

$24K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 2.2% lower than the average sale price ($624K) of 5 comparable homes.

SOLD MAY 11, 2026
$579,900
A
4 beds2.5 baths3,428 sq ft
43552 Bayberry Ct, Leonardtown, MD 20650
SOLD MAR 5, 2026
$560,000
B
4 beds2.5 baths2,594 sq ft
20753 Chestnut Ridge Dr, Leonardtown, MD 20650
SOLD SEP 8, 2026
$674,000
C
4 beds3.5 baths3,381 sq ft
20750 Deer Wood Park 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 JAN 8, 2026
$580,000
E
5 beds2.5 baths4,112 sq ft
21039 Woodmere Dr, Leonardtown, MD 20650

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

Earn from this home

Sell

$573,484

Est. take-home

List your home with Redfin and save $6,106

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 20644 Chestnut Ridge Dr

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2025

$6,398 (+7.9%)

2024

$5,928 (+9.5%)

$125,900 + $456,800

$582,700

2023

$5,415 (+6.6%)

2022

$5,078 (+1.1%)

2021

$5,023 (+1.1%)

$125,900 + $357,900

$483,800

2020

$4,969 (+1.1%)

2019

$4,915 (+0.9%)

2018

$4,870 (+1.3%)

2017

$4,809 (+3.6%)

2015

$4,640 (−10.7%)

$120,900 + $334,900

$455,800

2014

$5,195

$120,900 + $377,700

$498,600

2013

$5,196 (+0.6%)

2012

$5,166 (−9.8%)

2011

$5,727

2010

$5,727 (+17.3%)

2009

$4,881

Tax history for 20644 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$6,398 (+7.9%)

2024

$5,928 (+9.5%)

$125,900 + $456,800

$582,700

2023

$5,415 (+6.6%)

2022

$5,078 (+1.1%)

2021

$5,023 (+1.1%)

$125,900 + $357,900

$483,800

2020

$4,969 (+1.1%)

2019

$4,915 (+0.9%)

2018

$4,870 (+1.3%)

2017

$4,809 (+3.6%)

2015

$4,640 (−10.7%)

$120,900 + $334,900

$455,800

2014

$5,195

$120,900 + $377,700

$498,600

2013

$5,196 (+0.6%)

2012

$5,166 (−9.8%)

2011

$5,727

2010

$5,727 (+17.3%)

2009

$4,881

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Permits

Nov 25, 2014 • Final

Bldg detach acc

Construct a detached shed and workshop.

ADU

Jun 24, 2013 • Active

Residential accessory structure

Work on a shed and workshop.

ADU

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

Interior

Bathroom Information
# of Full Baths: 2
# of 1/2 Baths: 1

Heating & Cooling
Air Conditioning Type: Split System
Heating Type: Heat Pump

Fireplace Information
# of Fireplaces: 1
Fireplace Type: 2 Story Frame
Has Fireplace

Exterior

Exterior Information
Building Construction Quality: Good
Exterior Wall: Aluminum/Vinyl
Building Type: Single Family

Property Information
Subdivision Name: CHESTNUT RDG SEC 02
Living Sq. Ft: 5,104
Building Sq. Ft: 5,604
# of Stories: 2
Stories Type: 2
Legal Description: CHESTNUT RIDGE

Parking & Garage Information
Parking Type: Built-In Garage
Garage/Parking Sq. Ft: 500
Garage / Carport Type: Built In

Lot Information
# of Buildings: 1
Land Sq. Ft: 95,396
Legal Lot Number: 76
Acres: 2.19
Zoning Code: RNC
State Use Description: RESIDENTIAL

Utility Information
Sewer Type: Private
Water Service Type: Private

Financial

Assessor Information
Assessment Year: 2026
Tax District County: 03

Public facts

Beds: —
Baths: 2.5
Sq. Ft.: 5,104
Stories: 2.0
Lot Size: 2.19 acres
Style: Single Family Residential
Year Built: 1991
Year Renovated: —
County: St. Mary's County
APN: 03 048640

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 • 5.2mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.3mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 2.9mi

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

$581,000 – $703,000

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Home values near 20644 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20550 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2742 Sq. Ft.	$611,547
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
20753 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2594 Sq. Ft.	$599,648
20704 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3.5 Baths \| 3642 Sq. Ft.	$445,311
20760 Chestnut Ridge Dr, Leonardtown, MD 6 Beds \| 3.5 Baths \| 3492 Sq. Ft.	$662,916
43268 Oakway Ct, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2886 Sq. Ft.	$586,890

Address	Redfin Estimate
20590 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2846 Sq. Ft.	$601,688
20565 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3406 Sq. Ft.	$609,354
20776 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2606 Sq. Ft.	$547,073
20676 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 1792 Sq. Ft.	$513,757
20714 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2768 Sq. Ft.	$531,432
43298 Oakway Ct, Leonardtown, MD - Beds \| 2.5 Baths \| 1950 Sq. Ft.	$512,094
43280 Oakway Ct, Leonardtown, MD - Beds \| 2.5 Baths \| 2294 Sq. Ft.	$493,542

Address	Redfin Estimate
20576 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2785 Sq. Ft.	$678,294
20591 Chestnut Ridge Dr, Leonardtown, MD 5 Beds \| 3.5 Baths \| 3061 Sq. Ft.	$632,515
20735 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3 Baths \| 2568 Sq. Ft.	$598,433
20708 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2580 Sq. Ft.	$613,344
20740 Chestnut Ridge Dr, Leonardtown, MD 4 Beds \| 3 Baths \| 3572 Sq. Ft.	$655,172
43261 Oakway Ct, Leonardtown, MD - Beds \| 3 Baths \| 3288 Sq. Ft.	$645,486
43250 Prince Pine Ct, Leonardtown, MD - Beds \| 3.5 Baths \| 3500 Sq. Ft.	$736,797

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