$574,900

beds

baths

half bath

2,594

square ft

20753 Chestnut Ridge Drive

Leonardtown, Maryland 20650

Active / MLS #MDSM2028218 / Single Family / Leonardtown

Listing information updated 11/25/2025 at 4:21pm

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 Step inside and 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 Features

Architecture Style:

Colonial

Beds Above Grade:

Cooling System:

Central A/C, Ceiling Fan(s), Heat Pump(s)

Heating System:

Heat Pump(s)

Appliances:

Dishwasher, Dryer, Exhaust Fan, Microwave, Oven - Double, Oven/Range - Electric, Refrigerator, Washer

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

31 Years

Parking Spaces:

Garage:

Garage

Water Front:

Square Feet:

2,594

Lot Size:

87120.00 Square Feet

Acreage:

2.00

Internal Features:

Bathroom - Walk-In Shower, Chair Railings, Crown Moldings, Kitchen - Island, Primary Bath(s), Pantry, Upgraded Countertops, Wood Floors

Taxes & Assessments

Tax Amount:

$4,471

Tax Year:

2025

Assessments:

$100 / year

Location

Zip Code:

20650

City:

Leonardtown

County:

Saint Marys

Schools

School District(s):

ST. MARYS COUNTY PUBLIC SCHOOLS

Elementary School:

N/A

Middle School:

Leonardtown

High School:

Leonardtown

Architecture Style:

Colonial

Beds Above Grade:

Cooling System:

Central A/C, Ceiling Fan(s), Heat Pump(s)

Heating System:

Heat Pump(s)

Appliances:

Dishwasher, Dryer, Exhaust Fan, Microwave, Oven - Double, Oven/Range - Electric, Refrigerator, Washer

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

31 Years

Parking Spaces:

Garage:

Garage

Water Front:

Square Feet:

2,594

Lot Size:

87120.00 Square Feet

Acreage:

2.00

Internal Features:

Bathroom - Walk-In Shower, Chair Railings, Crown Moldings, Kitchen - Island, Primary Bath(s), Pantry, Upgraded Countertops, Wood Floors

Tax Amount:

$4,471

Tax Year:

2025

Assessments:

$100 / year

Zip Code:

20650

City:

Leonardtown

County:

Saint Marys

School District(s):

ST. MARYS COUNTY PUBLIC SCHOOLS

Elementary School:

N/A

Middle School:

Leonardtown

High School:

Leonardtown

Listing Office: CENTURY 21 New Millennium

Listing Office Phone: 301.862.2169

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