Google street view image for 20787 Chestnut Ridge Dr, Leonardtown, MD 20650

Off market sep 1996 for $207K

$574,088

Est. refi paymentEst. refi $1,399/mo

—

•

2.5 ba

•

2,602

sq ft

20787 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

20787 Chestnut Ridge Dr is a 2,602 square foot house on a 2 acre lot with 2.5 bathrooms. - it last sold on September 04, 1996 for $207,500. Based on Redfin's Leonardtown data, we estimate the home's value is $574,088.

Single-familyProperty Type

1992Year Built

2 acresLot Size

$221Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$574,088

$367K since sold in September 1996$6,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 15.5% lower than the average sale price ($679K) of 5 comparable homes.

SOLD MAR 5, 2026
$560,000
A
4 beds2.5 baths2,594 sq ft
20753 Chestnut Ridge 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 AUG 31, 2026
$976,000
C
4 beds2.5 baths2,550 sq ft
41402 Philip Ln, Leonardtown, MD 20650
SOLD MAR 26, 2026
$554,000
D
4 beds2.5 baths2,655 sq ft
44180 Cross Bow Ln, California, MD 20619
SOLD MAY 14, 2026
$727,360
E
4 beds2.5 baths2,972 sq ft
43500 Deer Run Ct, Leonardtown, MD 20650

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Earn from this home

Sell

$539,051

Est. take-home

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Refinance

Est. cash available

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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

LISTED BY REDFIN
$489,900
3 beds2.5 baths1,976 sq ft
22301 White Oak Rd, Leonardtown, MD 20650
$79,900
— beds— baths1,542 sq ft
21944 Point Lookout Rd, Leonardtown, MD 20650
(443) 968-9595
COMING SOON
$467,000
3 beds2.5 baths1,568 sq ft
22630 Quiet Ln, Leonardtown, MD 20650
(301) 884-9493
COMING SOON
$2,200,000
4 beds3 baths4,395 sq ft
22395 Newtowne Neck Rd, Leonardtown, MD 20650
(443) 975-7555
$650,000
4 beds3.5 baths3,264 sq ft
41427 Osborne Ln, Leonardtown, MD 20650
(443) 771-8009
$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
See all

Provided by Redfin

Sale history for 20787 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$4,383 (+5.7%)

2024

$4,147 (+6.8%)

$125,000 + $356,100

$481,100

2023

$3,883 (+3.7%)

2022

$3,746 (+2.7%)

2021

$3,648 (+2.7%)

$125,000 + $227,800

$352,800

2020

$3,551 (+2.8%)

2019

$3,453 (+0.6%)

2018

$3,433 (+1.1%)

2017

$3,396 (+4.5%)

2015

$3,249 (−9.2%)

$120,000 + $199,200

$319,200

2014

$3,577 (+4.2%)

$120,000 + $244,400

$364,400

2013

$3,433 (+5.2%)

2012

$3,264 (+3.5%)

2011

$3,155

2010

$3,155 (+20.6%)

2009

$2,616

Tax history for 20787 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$4,383 (+5.7%)

2024

$4,147 (+6.8%)

$125,000 + $356,100

$481,100

2023

$3,883 (+3.7%)

2022

$3,746 (+2.7%)

2021

$3,648 (+2.7%)

$125,000 + $227,800

$352,800

2020

$3,551 (+2.8%)

2019

$3,453 (+0.6%)

2018

$3,433 (+1.1%)

2017

$3,396 (+4.5%)

2015

$3,249 (−9.2%)

$120,000 + $199,200

$319,200

2014

$3,577 (+4.2%)

$120,000 + $244,400

$364,400

2013

$3,433 (+5.2%)

2012

$3,264 (+3.5%)

2011

$3,155

2010

$3,155 (+20.6%)

2009

$2,616

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

Permits

Jun 1, 2007 • Final

Bldg new construction

Work on a sunroom and deck.

Addition

Feb 14, 2006 • Active

Residential addition

Construct a new sunroom and deck addition.

Addition

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 RIDGE
Living Sq. Ft: 2,602
Building Sq. Ft: 3,130
# of Stories: 2
Stories Type: 2
Legal Description: LOT 52 SECTION THREE PLAT 35/5 CHESTNUT RIDGE

Parking & Garage Information
Parking Type: Built-In Garage
Garage/Parking Sq. Ft: 528
Garage / Carport Type: Built In

Lot Information
# of Buildings: 1
Land Sq. Ft: 87,120
Legal Lot Number: 52
Acres: 2
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.: 2,602
Stories: 2.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 1992
Year Renovated: —
County: St. Mary's County
APN: 03 050904

Home facts updated by county records on Oct 16, 2026

Around this home

Schools

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 • 2.7mi

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

$546,000 – $661,000

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Nearby similar homes

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New listings for sale in 20650

LISTED BY REDFIN3D WALKTHROUGH

$489,900

3 beds2.5 baths1,976 sq ft

22301 White Oak Rd, Leonardtown, MD 20650

$79,900

— beds— baths1,542 sq ft

21944 Point Lookout Rd, Leonardtown, MD 20650

(443) 968-9595

COMING SOON

$467,000

3 beds2.5 baths1,568 sq ft

22630 Quiet Ln, Leonardtown, MD 20650

(301) 884-9493

COMING SOON

$2,200,000

4 beds3 baths4,395 sq ft

22395 Newtowne Neck Rd, Leonardtown, MD 20650

(443) 975-7555

$650,000

4 beds3.5 baths3,264 sq ft

41427 Osborne Ln, Leonardtown, MD 20650

(443) 771-8009

$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

Home values near 20787 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20829 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3.5 Baths \| 3683 Sq. Ft.	$568,741
20735 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3 Baths \| 2568 Sq. Ft.	$605,496

Address	Redfin Estimate
20784 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 3 Baths \| 2802 Sq. Ft.	$594,144
20753 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2594 Sq. Ft.	$600,369

Address	Redfin Estimate
20776 Chestnut Ridge Drive, Leonardtown, MD 4 Beds \| 2.5 Baths \| 2606 Sq. Ft.	$538,610
20800 Chestnut Ridge Drive, Leonardtown, MD - Beds \| 2.5 Baths \| 3320 Sq. Ft.	$663,739

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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 20787 Chestnut Ridge Dr

Tax history for 20787 Chestnut Ridge Dr

Permits

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 20787 Chestnut Ridge Dr

More real estate resources