
Residential Land with Home for Sale in Leonardtown, Maryland
20753 Chestnut Ridge Dr, Leonardtown, MD 20650
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
Location
- Street address
- 20753 Chestnut Ridge Dr
- County
- Saint Mary's County
- Community
- Chestnut Ridge
- School district
- St. Marys County Public Schools
- Elevation
- 110 feet
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
| Name | Level | District | Description |
|---|---|---|---|
| Leonardtown | Middle | St. Marys County Public Schools | — |
| Leonardtown | High | St. Marys County Public Schools | — |
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| Jan 13, 2026 | Price drop | $564,900 | $10,000 -1.7% | TREND |
| Nov 25, 2025 | New listing | $574,900 | — | TREND |












































