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Residential Land with Home for Sale in Leonardtown, Maryland

20753 Chestnut Ridge Dr, Leonardtown, MD 20650

$564,900
2 acres
Active
$10k drop
Est $3,149/mo

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

2,594
Sq feet
4
Beds
2
Full baths
1
1/2 bath
1994
Built

Location

Street address
20753 Chestnut Ridge Dr
Community
Chestnut Ridge
School district
St. Marys County Public Schools
Elevation
110 feet
Coordinates
38.2383, -76.578

Property details

Acreage
2 acres
MLS #
TREND MDSM2028218
Posted

Property taxes

Recent
$4,471

Expenses

Home Owner Assessments Fee
$100 annually

Parcels

  • 1903048489

Details and features

Listing

Type
Residential
Franchise
Century 21 Real Estate

Exterior

Parking Spaces
2
Parking
Attached Garage

Structure

Style
Colonial
Heating
Heat Pump
Cooling
Ceiling Fan(s), Central Air
Materials
Vinyl Siding

Interior

Rooms
Bathroom x 3, Bedroom x 4
Appliances
Dishwasher, Double Oven, Dryer, Electric Oven/Range, Exhaust Fan, Microwave, Refrigerator, Washer
Features
Chair Railings, Crown Moldings, Island Kitchen, Pantry, Primary Bath(s), Upgraded Countertops, Walk-In Shower Bathroom, Wood Floors

Nearby schools

NameLevelDistrictDescription
LeonardtownMiddleSt. Marys County Public Schools
LeonardtownHighSt. Marys County Public Schools

Listing history

DateEventPriceChangeSource
Jan 13, 2026Price drop$564,900$10,000 -1.7%TREND
Nov 25, 2025New listing$574,900TREND
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This 2-acre property is located at 20753 Chestnut Ridge Dr in Leonardtown, MD 20650. The property is available for sale for $564,900. It has a 2,594 sq ft 4 bedroom, 2 bath house built in 1994.

Checked 7 hours ago — Updated

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