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
Pending
Price cut: $10K (1/13)
$564,900
20753 Chestnut Ridge Dr, Leonardtown, MD 20650
4beds
2,594sqft
Est.:
Single Family Residence
Built in 1994
2 Acres Lot
$563,000 Zestimate®
$218/sqft
$8/mo HOA
What's special
Beautifully updated kitchenSpacious walk-in closetSeparate showerStainless steel appliancesCenter islandSpacious separate dining roomCorian countertops
- 82 days |
- 293 |
- 13 |
Zillow last checked: 8 hours ago
Listing updated: January 21, 2026 at 03:33am
Listed by:
Tracey Summers 240-298-8917,
CENTURY 21 New Millennium (301) 862-2169
Source: Bright MLS,MLS#: MDSM2028218
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Basement
- Area: 0
Heating
- Heat Pump, Electric
Cooling
- Central Air, Ceiling Fan(s), Heat Pump, Electric
Appliances
- Included: Dishwasher, Dryer, Exhaust Fan, Microwave, Double Oven, Oven/Range - Electric, Refrigerator, Washer, Electric Water Heater
Features
- Bathroom - Walk-In Shower, Chair Railings, Crown Molding, Kitchen Island, Primary Bath(s), Pantry, Upgraded Countertops
- Flooring: Wood
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Brick, Wood Burning
Interior area
- Total structure area: 2,594
- Total interior livable area: 2,594 sqft
- Finished area above ground: 2,594
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Garage Door Opener, Inside Entrance, Oversized, Attached
- Attached garage spaces: 2
Accessibility
- Accessibility features: None
Features
- Levels: Two
- Stories: 2
- Pool features: None
Lot
- Size: 2 Acres
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1903048489
- Zoning: RNC
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Permanent
Condition
- Excellent
- New construction: No
- Year built: 1994
Utilities & green energy
- Sewer: Septic Exists
- Water: Private
Community & HOA
Community
- Subdivision: Chestnut Ridge
HOA
- Has HOA: Yes
- HOA fee: $100 annually
Location
- Region: Leonardtown
Financial & listing details
- Price per square foot: $218/sqft
- Tax assessed value: $465,800
- Annual tax amount: $4,471
- Date on market: 11/25/2025
- Listing agreement: Exclusive Right To Sell
- Ownership: Fee Simple
Estimated market value
$563,000
$535,000 - $591,000
$3,182/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/21/2026 | Pending sale | $564,900$218/sqft |
Source:  Bright MLS #MDSM2028218 Report a problem | ||
| 1/13/2026 | Price change | $564,900-1.7%$218/sqft |
Source: Bright MLS #MDSM2028218 Report a problem | ||
| 11/25/2025 | Listed for sale | $574,900+206%$222/sqft |
Source: Bright MLS #MDSM2028218 Report a problem | ||
| 1/31/1995 | Sold | $187,900$72/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $166 -95.9% | $465,800 +9.6% |
| 2024 | $4,078 +10.7% | $424,867 +10.7% |
| 2023 | $3,685 +11.9% | $383,933 +11.9% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$3,238/mo
Principal & interest
$2655
Property taxes
$377
Other costs
$206
Climate risks
Neighborhood: 20650
Nearby schools
GreatSchools rating
- 9/10Piney Point Elementary SchoolGrades: PK-5Distance: 5.4 mi
- 8/10Leonardtown Middle SchoolGrades: 6-8Distance: 3.1 mi
- 5/10Leonardtown High SchoolGrades: 9-12Distance: 2.7 mi
Schools provided by the listing agent
- Middle: Leonardtown
- High: Leonardtown
- District: St. Marys County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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