OFF MARKET

Off market oct 2017 for $345K

$566,682

Est. refi paymentEst. refi $2,276/mo

•

2,700

sq ft

20499 Chestnut Ridge Dr, Leonardtown, MD 20650

About this home

Single-familyProperty Type

1994Year Built

2.31 acresLot Size

$210Est. Price/Sq.Ft.

2 car garageParking

Listed by Cindy Ballard • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Bought with Cindy Ballard • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #1000073817

Redfin Estimate

$566,682

$222K since sold in October 2017$6,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.9% lower than the average sale price ($629K) 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 MAR 5, 2026
$560,000
B
4 beds2.5 baths2,594 sq ft
20753 Chestnut Ridge Dr, Leonardtown, MD 20650
SOLD SEP 18, 2026
$605,000
C
3 beds2.5 baths2,052 sq ft
20980 Aster Dr, Callaway, MD 20620
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

$308,070

Est. take-home

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Refinance

Est. cash available

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Rent

$2,604/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 20499 Chestnut Ridge Dr

** Price available after signing in.

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2025

$4,749 (+7.2%)

2024

$4,428 (+8.7%)

$126,500 + $302,000

$428,500

2023

$4,074 (+5.8%)

2022

$3,850 (+1.3%)

2021

$3,800 (+1.4%)

$126,500 + $236,600

$363,100

2020

$3,749 (+1.4%)

2019

$3,698 (+0.6%)

2018

$3,678 (+1.0%)

2017

$3,640 (+4.2%)

2015

$3,492 (−1.5%)

$121,500 + $221,600

$343,100

2014

$3,546 (+4.3%)

$121,500 + $222,000

$343,500

2013

$3,401 (+5.2%)

2012

$3,233 (+2.8%)

2011

$3,147

2010

$3,147 (+20.6%)

2009

$2,609

Tax history for 20499 Chestnut Ridge Dr

Year

Property tax

Land + Additions

Assessment*

2025

$4,749 (+7.2%)

2024

$4,428 (+8.7%)

$126,500 + $302,000

$428,500

2023

$4,074 (+5.8%)

2022

$3,850 (+1.3%)

2021

$3,800 (+1.4%)

$126,500 + $236,600

$363,100

2020

$3,749 (+1.4%)

2019

$3,698 (+0.6%)

2018

$3,678 (+1.0%)

2017

$3,640 (+4.2%)

2015

$3,492 (−1.5%)

$121,500 + $221,600

$343,100

2014

$3,546 (+4.3%)

$121,500 + $222,000

$343,500

2013

$3,401 (+5.2%)

2012

$3,233 (+2.8%)

2011

$3,147

2010

$3,147 (+20.6%)

2009

$2,609

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

Public record

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

2.31 Acres

Year renovated

—

Sq. Ft.

2,700

Year built

1994

Style

Single Family Residential

County

St. Mary's County

APN

03 053474

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 Door Opener, Garage - Front Entry
# of Total Garage and Parking Spaces: 2
Has Garage
# of Garage Spaces: 2
Garage
Attached Garage

Interior

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full) On 1st Lower Level: 1
# of Bathrooms (Full): 3

Interior Information
Appliances: Dryer, Dishwasher, Exhaust Fan, Extra Refrigerator/Freezer, Icemaker, Microwave, Refrigerator, Oven/Range - Electric, Washer, Water Heater
Entry Location: Foyer
Interior Features: Kitchen - Island, Combination Kitchen/Dining, Combination Kitchen/Living, Entry Level Bedroom, Window Treatments, Master Bath(s), Wood Floors
Living Area Sq.Ft. Source: Estimated

Fireplace Information
Has Fireplace
# of Fireplaces: 1

Basement Information
Basement: Yes
Connecting Stairway, Rear Entrance, Sump Pump, Fully Finished, Walkout Level

Exterior

Property Information
Total Below Grade Sq. Ft.: 900
Improvement Assessed Value: $232,200
Ownership Interest: Fee Simple
Property Condition: Very Good
Year Built Source: Estimated

Building Information
Construction Materials: Combination, Brick
Other Structures: Above Grade, Below Grade, Shed
Outdoor Living Structures: Deck(s)
Structure Type: Detached
Other Structures: Shed

Exterior Information
Satellite Dish

Lot Information
Lot Features: Backs to Trees
Tidal Water: No

Land Information
Land Assessed Value: $116,500

Above Grade Information
Finished Sq.Ft.: 1,800
Finished Sq.Ft. Source: Estimated

Below Grade Information
Finished Sq.Ft.: 900
Finished Sq.Ft. Source: Estimated

Financial

Tax Information
County Tax: $3,308.51
Tax Assessed Value: $348,700
Tax Year: 2016
Tax Annual Amount: $3,504.08

Assessments Information
Special Assessment Payment: Annually
Year Assessed: 2017

Utilities

Utilities Information
Cooling Type: Heat Pump(s)
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Bottled Gas/Propane, Electric
Hot Water: Bottled Gas
Sewer Septic: Septic Exists
Water Source: Well

Location

Homeowners Association Information
HOA Fee: $110
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

Location Information
Directions: Rt 5 to Chestnut Ridge Drive. Home near end of road on the right.

Public facts

Beds: —
Baths: 3.0
Sq. Ft.: 2,700
Stories: 1.0
Lot Size: 2.31 acres
Style: Single Family Residential
Year Built: 1994
Year Renovated: —
County: St. Mary's County
APN: 03 053474

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 • 4.9mi

7/10

Leonardtown Middle School

Public 6-8 • Assigned • 3.6mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 3.3mi

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

$539,000 – $652,000

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Home values near 20499 Chestnut Ridge Dr

Data from public records.

Address	Redfin Estimate
20482 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2911 Sq. Ft.	$616,902
20525 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3194 Sq. Ft.	$598,704
20496 Chestnut Ridge Dr, Leonardtown, MD 5 Beds \| 4.5 Baths \| 2945 Sq. Ft.	$643,011
20484 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 1744 Sq. Ft.	$480,676
20535 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 3165 Sq. Ft.	$584,988
20503 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 1848 Sq. Ft.	$505,850
20572 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3.5 Baths \| 3840 Sq. Ft.	$683,535

Address	Redfin Estimate
20479 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2400 Sq. Ft.	$577,825
20520 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 2.5 Baths \| 2329 Sq. Ft.	$625,118
20490 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3.5 Baths \| 2536 Sq. Ft.	$594,288
20480 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 4.5 Baths \| 4452 Sq. Ft.	$747,275
20483 Chestnut Ridge Dr, Leonardtown, MD 5 Beds \| 2.5 Baths \| 2908 Sq. Ft.	$638,696
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

Address	Redfin Estimate
20507 Chestnut Ridge Dr, Leonardtown, MD 3 Beds \| 3 Baths \| 1705 Sq. Ft.	$559,540
20500 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2694 Sq. Ft.	$581,955
20550 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 2.5 Baths \| 2742 Sq. Ft.	$611,547
20511 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3.5 Baths \| 4448 Sq. Ft.	$682,336
20485 Chestnut Ridge Dr, Leonardtown, MD - Beds \| 3 Baths \| 2574 Sq. Ft.	$582,146
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

Property information provided by BRIGHT MLS when last listed in 2017. This data may not match . Learn more.

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