20550 Chestnut Ridge Dr, Leonardtown, MD 20650 is a single family home that contains 2,742 sq ft and was built in 1996. It contains 2.5 bathrooms. This home last sold for $573,000 in April 2026.
The Zestimate for this house is $577,300. The Rent Zestimate for this home is $3,095/mo.
Sold for $573,000
Street View
$573,000
20550 Chestnut Ridge Dr, Leonardtown, MD 20650
--beds
2baths
2,742sqft
SingleFamily
Built in 1996
2.24 Acres Lot
$577,300 Zestimate®
$209/sqft
$3,095 Estimated rent
Home value
$577,300
$520,000 - $641,000
$3,095/mo
Zestimate® history
Owner options
List your home for rent
$3,095/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$3,095/mo
Rent Zestimate®
Refinance and save
$3,491/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$3,491/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Facts & features
Interior
Bedrooms & bathrooms
- Bathrooms: 2.5
Heating
- Heat pump
Features
- Has fireplace: Yes
Interior area
- Total interior livable area: 2,742 sqft
Property
Parking
- Parking features: Garage - Attached
Features
- Exterior features: Other
Lot
- Size: 2.24 Acres
Details
- Parcel number: 03053598
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Conventional
Materials
- Roof: Shake / Shingle
Condition
- Year built: 1996
Community & HOA
HOA
- Has HOA: Yes
- HOA fee: $9 monthly
Location
- Region: Leonardtown
Financial & listing details
- Price per square foot: $209/sqft
- Tax assessed value: $523,500
- Annual tax amount: $4,628
Price history
| Date | Event | Price |
|---|---|---|
| 4/21/2026 | Sold | $573,000$209/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,628 +1.6% | $523,500 +10.3% |
| 2024 | $4,556 +11.5% | $474,633 +11.5% |
| 2023 | $4,087 +13% | $425,767 +13% |
| 2022 | $3,617 +3.5% | $376,900 +3.5% |
| 2021 | $3,494 +3.7% | $364,033 +3.7% |
| 2020 | $3,371 +3.8% | $351,167 +3.8% |
| 2019 | $3,247 +0.6% | $338,300 +0.6% |
| 2018 | $3,227 -0.3% | $336,233 +0.6% |
| 2017 | $3,238 +2.1% | $334,167 +0.6% |
| 2016 | $3,170 | $332,100 |
| 2015 | $3,170 | $332,100 |
| 2014 | $3,170 | $332,100 -5.6% |
| 2013 | -- | $351,800 |
| 2012 | -- | $351,800 |
| 2011 | -- | $351,800 -11.8% |
| 2010 | -- | $399,030 +6.7% |
| 2009 | -- | $374,040 +7.2% |
| 2008 | -- | $349,050 +7.7% |
| 2007 | -- | $324,060 +13.2% |
| 2006 | -- | $286,280 +15.2% |
| 2005 | -- | $248,500 +17.9% |
| 2004 | -- | $210,720 |
| 2003 | -- | $210,720 |
| 2002 | -- | $210,720 -1.2% |
| 2001 | -- | $213,310 |
Find assessor info on the county website
Neighborhood: 20650
Nearby homes
- $627,7003 bd3 ba2.3k sqft20520 Chestnut Ridge Dr, Leonardtown, MD 20650Off Market
- $636,900-- bd3 ba2.6k sqft20565 Chestnut Ridge Dr, Leonardtown, MD 20650Off Market
- $626,9005 bd3 ba2.8k sqft20590 Chestnut Ridge Dr, Leonardtown, MD 20650Off Market
- $641,6005 bd4 ba3.9k sqft20535 Chestnut Ridge Dr, Leonardtown, MD 20650Off Market
- $601,000-- bd3 ba2k sqft20500 Chestnut Ridge Dr, Leonardtown, MD 20650Off Market
- $744,2005 bd2 ba4.4k sqft20572 Chestnut Ridge Dr, Leonardtown, MD 20650Off Market
- $625,7005 bd5 ba2.9k sqft20496 Chestnut Ridge Dr, Leonardtown, MD 20650Off Market
- $599,9005 bd4 ba3k sqft20591 Chestnut Ridge Dr, Leonardtown, MD 20650Sold
Nearby schools
GreatSchools rating
- 9/10Piney Point Elementary SchoolGrades: PK-5Distance: 5 mi
- 8/10Leonardtown Middle SchoolGrades: 6-8Distance: 3.4 mi
- 5/10Leonardtown High SchoolGrades: 9-12Distance: 3.1 mi
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$577,300
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$577,300
- Maryland
- Saint Marys County
- Leonardtown
- 20650
- 20550 Chestnut Ridge Dr
Nearby cities
Nearby zip codes
Other Leonardtown Topics
