20753 Chestnut Ridge Drive, Leonardtown, MD 20650 - Photo 1

1/1

$560,000

Sold
Closed
Single Family
4 Beds
2 Full Baths
1 Partial Bath
2,594 Sq. Ft.
2 Car Garage

1/1

Property Description

Nestled within one of the most desirable subdivisions, this classic two-story Colonial welcomes you home with charm and a sense of privacy on two wooded acres. Quality construction throughout from the sunroom to the kitchen remodel you will see the workmanship! Once inside you will feel the warmth of meticulously cared-for details : gleaming hardwood floors through the main level, a spacious separate dining room into a beautifully updated kitchen. Corian countertops, stainless steel appliances, and center island make it a joy to cook and gather Kitchen opens into a cozy family room anchored by a wood-burning fireplace and a light-filled sunroom with lots of windows inviting the outside in. Connecting deck overlooking your own peaceful woods Upstairs, four generous bedrooms offer restful retreats, including a primary suite with an en-suite bath featuring dual vanities, a soothing soaking tub, a separate shower, and a spacious walk-in closet. Practical touches complete the picture: an oversized two-car garage for all your toys and storage, plus a charming large Amish-built shed Bonus! Encapsulated crawlspace w/ commercial grade dehumidifier, sprinkler system, heat pump 2024, new roof 2016

Full Property Details

Full Property Details for 20753 Chestnut Ridge Dr

General

Sold For: $560,000
HOA FEE: $8/month
HOA FEE FREQ.: Annually
Taxes: $4,471 (2025)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDSM2028218
Added to Site: 128 day(s) ago

Interior

Interior Features: Bathroom - Walk-In Shower, Chair Railings, Crown Moldings, Kitchen - Island, Primary Bath(s), Pantry, Upgraded Countertops, Wood Floors
Fireplace: Yes
Number of Fireplaces: 1
Fireplace(s): Brick, Wood
Appliances: Dishwasher, Dryer, Exhaust Fan, Microwave, Oven - Double, Oven/Range - Electric, Refrigerator, Washer

Rooms

Bathrooms

Total Bathrooms: 3
Full Bathrooms: 2
Half Bathrooms: 1
Upper Floor Baths: 2
Upper - Full Baths: 2
Main Floor Baths: 1
Main - 1/2 Baths: 1

Bedrooms

Total Bedrooms: 4
Bedrooms Upper: 4

Parking

Garage: Yes
Garage Spaces: 2
Total Spaces: 2
Parking Type: Attached Garage
Garage Description: Garage - Front Entry, Garage Door Opener, Inside Access, Oversized

Location

County: SAINT MARYS
Subdivision: CHESTNUT RIDGE
Driving Directions: Rt 5 To Chestnut Ridge Subdivision to property on right

School Information

School District: St. Marys County Public Schools
Middle School: Leonardtown
High School: Leonardtown

Community

Association: Yes

Heating & Cooling

Central air: Yes
Cooling Type: Central A/C, Ceiling Fan(s), Heat Pump(s)
Cooling Fuel: Electric
Heating Type: Heat Pump(s)
Heating Fuel: Electric
Water Heater: Electric

Utilities

Sewer: Septic Exists
Water: Private

Structural Information

Architectural Style: Colonial
Structure Type: Detached
Construction: Vinyl Siding
Foundation: Permanent
Stories Description: Main, Upper 1
Square Feet: 2,594
Sq. Ft. Source: Estimated
Living Area: 2,594 Sq. Ft.
Finished Above Grnd: 2,594 Sq. Ft.
Year Built: 1994
Year Built Source: Assessor
Property Condition: Excellent

Lot Features

Lot Size (Acres): 2
Lot Size (Sq. Ft.): 87,120
Lot Size Source: Assessor
Zoning: RNC

Financial Considerations

Price Per Sq. Ft.: $217.77
Association Fee: $100
Assoc Fee Freq.: Annually
Assessment Year: 2025
County Tax: $4,471
County Tax Freq: Annually
Tax w/Assessment: $465,800
Tax Amount: $4,471
Tax Year: 2025
Terms: Standard Sale
Tax Total Finished Sq. Ft.: 2474

Disclosures and Reports

Ownership: Fee Simple
Section: 2
Lot Number: 55

Listed by CENTURY 21 New Millennium, Tracey L Summers
Sold by CENTURY 21 New Millennium, Cynthia J Ballard

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Listing agent

— 20753 Chestnut Ridge Dr —

Tracey L Summers

CENTURY 21 New Millennium

Listing Office Email: tommy.higgins@c21nm.com

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NMLS#: 1598647

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Schools

Schools serving 20753 Chestnut Ridge Dr

School District:St. Marys County Public Schools

Name	Grades	Distance
Piney Point Elementary School 44550 Tall Timbers Road, Tall Timbers, MD 20690	PK-5	5.4 mi
Leonardtown Middle School 24015 Point Lookout Road, Leonardtown, MD 20650	6-8	3.1 mi
Leonardtown High School 23995 Point Lookout Road, Leonardtown, MD 20650	9-12	2.7 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 20753 Chestnut Ridge Dr

Date

Details

Price

Change

Source

3/05/2026

Sold

$560,000

-0.87%

MLS

1/13/2026

Price Reduced

$564,900

-1.74%

MLS

11/25/2025

Listed

$574,900

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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2
Beds
2
Total Baths
1,431
Sq. Ft.

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Closed

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Beds
4
Total Baths
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Total Baths
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Sq. Ft.

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Beds
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Total Baths
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20753 Chestnut Ridge Drive, Leonardtown, MD 20650 (MLS# MDSM2028218) is a Single Family property that was sold at $560,000 on March 05, 2026. Want to learn more about 20753 Chestnut Ridge Drive? Do you have questions about finding other Single Family real estate for sale in Leonardtown? You can browse all Leonardtown real estate or contact a Coldwell Banker agent to request more information.

20753 Chestnut Ridge Dr Leonardtown, MD 20650