Google street view image for 20500 Chestnut Ridge Dr, Leonardtown, MD 20650

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Sold

$592,658

Est. refi paymentEst. refi $3,069/mo

—

•

3 ba

•

2,694

sq ft

20500 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

LOVELY CAPE COD IN DESIRABLE CHESTNUT RIDGE LOCATED ON 2.31 BEAUTIFULLY LANDSCAPED ACRES. CUSTOM STAIRWAY, FULL UNFINISHED WALKOUT BASEMENT. LIKE TO ENTERTAIN OUTSIDE THEN YOU WILL LOVE THE TWO TIERED DECK TOP LEVEL 44'X16'. DOG WILL BE IN GARAGE DON'T LET HIM IN THE HOUSE DON'T LET CAT IN FROM OUTSIDE. POWDER RM AMD MASTER BATH MEDICINE CABINETS DO NOT CONVEY.

Single-familyProperty Type

1995Year Built

2.31 acresLot Size

$220Est. Price/Sq.Ft.

2 spacesParking

Source:Public Records

Redfin Estimate

$592,658

$158K since sold in September 2007$9,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 0.9% higher than the average sale price ($587K) 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 MAR 5, 2026
$560,000
B
4 beds2.5 baths2,594 sq ft
20753 Chestnut Ridge Dr, Leonardtown, MD 20650
SOLD JAN 23, 2026
$465,000
C
3 beds2 baths1,732 sq ft
43543 Bayberry Ct, 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 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

$556,555

Est. take-home

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Refinance

Est. cash available

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Rent

$2,777/mo

Redfin rental estimate

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Market trends in 20650, MD

Last updated September 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

OPEN OCT 24, 1PM TO 3PM
$440,000
3 beds3.5 baths2,379 sq ft
41608 Briarwood Cir, Leonardtown, MD 20650
(301) 298-2892
COMING SOON
$685,000
5 beds3.5 baths4,271 sq ft
23603 Margrave Dr, Leonardtown, MD 20650
(888) 860-7369
$590,000
4 beds4 baths3,750 sq ft
22220 Bull Rd, Leonardtown, MD 20650
(301) 855-8600
$299,500
3 beds1.5 baths1,218 sq ft
42163 Blacksmith Shop Rd, Leonardtown, MD 20650
(301) 862-2169
VIDEO TOUR
$450,000
3 beds3.5 baths2,306 sq ft
23405 Marview Ct, Leonardtown, MD 20650
(410) 394-0990
$475,000
3 beds2 baths1,462 sq ft
43705 Redmond Rd, Leonardtown, MD 20650
(301) 609-9000
$515,000
4 beds3.5 baths2,764 sq ft
22538 Landing Way, Leonardtown, MD 20650
(443) 771-8009
See all

Provided by Redfin

Sale history for 20500 Chestnut Ridge Dr

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Year

Property tax

Land + Additions

Assessment*

2025

$4,802 (+5.2%)

2024

$4,565 (+6.4%)

$126,500 + $340,300

$466,800

2023

$4,292 (+3.3%)

2022

$4,155 (+1.7%)

2021

$4,084 (+1.8%)

$126,500 + $266,600

$393,100

2020

$4,013 (+1.8%)

2019

$3,941 (+0.6%)

2018

$3,917 (+1.1%)

2017

$3,875 (+5.7%)

2015

$3,665 (−2.4%)

2014

$3,755

$121,500 + $235,600

$357,100

2013

$3,755 (+0.8%)

2012

$3,725 (−6.5%)

2011

$3,982

2010

$3,982 (+19.3%)

2009

$3,338

Tax history for 20500 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$4,802 (+5.2%)

2024

$4,565 (+6.4%)

$126,500 + $340,300

$466,800

2023

$4,292 (+3.3%)

2022

$4,155 (+1.7%)

2021

$4,084 (+1.8%)

$126,500 + $266,600

$393,100

2020

$4,013 (+1.8%)

2019

$3,941 (+0.6%)

2018

$3,917 (+1.1%)

2017

$3,875 (+5.7%)

2015

$3,665 (−2.4%)

2014

$3,755

$121,500 + $235,600

$357,100

2013

$3,755 (+0.8%)

2012

$3,725 (−6.5%)

2011

$3,982

2010

$3,982 (+19.3%)

2009

$3,338

*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

1.5

Lot width

—

Lot depth

—

Lot size

2.31 Acres

Year renovated

—

Sq. Ft.

2,694

Year built

1995

Style

Single Family Residential

County

St. Mary's County

APN

03 053563

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 16, 2026.

Property details

Around this home

Schools

Piney Point Elementary School

Public PreK-5 • Assigned • 4.9mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.5mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 3.2mi

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 102° 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

$564,000 – $682,000

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Nearby similar homes

$929,900

4 beds3.5 baths4,248 sq ft

20945 Greenwell Way, Leonardtown, MD 20650

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3 beds3 baths1,691 sq ft

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NEW 17 HRS AGO

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4 beds4 baths2,666 sq ft

20270 Beauvue Ct, Leonardtown, MD 20650

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4 beds3 baths2,414 sq ft

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$475,000

3 beds2.5 baths1,668 sq ft

22435 Indian Bridge Rd, California, MD 20619

(443) 771-8009

$425,000

2 beds2 baths1,905 sq ft

23134 Marble Way, California, MD 20619

(443) 771-8009

New listings for sale in 20650

OPEN OCT 24, 1PM TO 3PM

$440,000

3 beds3.5 baths2,379 sq ft

41608 Briarwood Cir, Leonardtown, MD 20650

(301) 298-2892

COMING SOON

$685,000

5 beds3.5 baths4,271 sq ft

23603 Margrave Dr, Leonardtown, MD 20650

(888) 860-7369

$590,000

4 beds4 baths3,750 sq ft

22220 Bull Rd, Leonardtown, MD 20650

(301) 855-8600

$299,500

3 beds1.5 baths1,218 sq ft

42163 Blacksmith Shop Rd, Leonardtown, MD 20650

(301) 862-2169

VIDEO TOUR

$450,000

3 beds3.5 baths2,306 sq ft

23405 Marview Ct, Leonardtown, MD 20650

(410) 394-0990

$475,000

3 beds2 baths1,462 sq ft

43705 Redmond Rd, Leonardtown, MD 20650

(301) 609-9000

$515,000

4 beds3.5 baths2,764 sq ft

22538 Landing Way, Leonardtown, MD 20650

(443) 771-8009

Home values near 20500 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20482 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 3 Baths \| 2911 Sq. Ft.	$608,636
20525 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 3 Baths \| 3194 Sq. Ft.	$585,889

Address	Redfin Estimate
20479 Chestnut Ridge Drive, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2400 Sq. Ft.	$576,001
20520 Chestnut Ridge Drive, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2329 Sq. Ft.	$627,872

Address	Redfin Estimate
20507 Chestnut Ridge Drive, Leonardtown, MD 3 Beds \| 3 Baths \| 1705 Sq. Ft.	$547,893
20496 Chestnut Ridge Drive, Leonardtown, MD 5 Beds \| 4.5 Baths \| 2945 Sq. Ft.	$631,592

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GreatSchools Ratings provided by GreatSchools.org.

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20500 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Sale history for 20500 Chestnut Ridge Dr

Tax history for 20500 Chestnut Ridge Dr

Public record

Property details

Public facts

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 20650

Home values near 20500 Chestnut Ridge Dr

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