Welcome to this well-built colonial on a corner lot in the picturesque corner Chestnut Ridge neighborhood! With over 3,000 finished square feet, 5 bedrooms, and 3.5 bathrooms, this home is full of charm, character, and thoughtful craftsmanship. Situated on 2.11 acres, the home features a classic brick exterior, a welcoming front porch, and a spacious two-car garage. Inside on the main level, you'll find two comfortable living areas, a dedicated dining space, and a kitchen with granite countertops, stainless steel appliances, and plenty of room to make it your own. Step right out onto the back deck to enjoy the peaceful, private outdoor setting. All five bedrooms are located on the second and third floors, offering privacy and space for everyone. The rooms are generously sized, including a spacious primary suite and a versatile bonus room above the garage—perfect for a home office, playroom, or guest retreat. The unfinished basement adds even more flexibility, offering excellent storage or future expansion potential. New Roof in 2018. New Sump Pump 2025. Enjoy the quiet setting, timeless design, and endless potential Chestnut Ridge gem offers—ready for its next chapter. Don’t miss your chance to own a home with this much space, land, and value—schedule your private showing today! Back on the market, due to buyer not meeting home sale contingency
Sold for $599,900
$599,900
20591 Chestnut Ridge Dr, Leonardtown, MD 20650
5beds
3,061sqft
Single Family Residence
Built in 1995
2.11 Acres Lot
$608,100 Zestimate®
$196/sqft
$3,394 Estimated rent
Home value
$608,100
$553,000 - $669,000
$3,394/mo
Zestimate® history
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Owner options
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What's special
Zillow last checked: 8 hours ago
Listing updated: November 03, 2025 at 03:44pm
Listed by:
Lauren Garner 240-925-5158,
EXP Realty, LLC
Bought with:
Matt Burgan, 663374
Infinitas Realty Group
Source: Bright MLS,MLS#: MDSM2025274
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 1
Primary bedroom
- Features: Flooring - Carpet, Ceiling Fan(s), Walk-In Closet(s)
- Level: Upper
Bedroom 2
- Features: Flooring - Carpet, Ceiling Fan(s)
- Level: Upper
Bedroom 3
- Features: Flooring - Carpet, Ceiling Fan(s)
- Level: Upper
Bedroom 4
- Features: Flooring - Carpet, Ceiling Fan(s)
- Level: Upper
Bedroom 5
- Features: Flooring - Carpet, Ceiling Fan(s)
- Level: Upper
Primary bathroom
- Features: Soaking Tub, Double Sink
- Level: Upper
Basement
- Features: Basement - Unfinished
- Level: Lower
Dining room
- Features: Flooring - HardWood
- Level: Main
Foyer
- Level: Main
Other
- Level: Upper
Other
- Features: Bathroom - Tub Shower
- Level: Upper
Half bath
- Level: Main
Kitchen
- Features: Granite Counters, Flooring - HardWood, Kitchen Island, Kitchen - Propane Cooking, Pantry
- Level: Main
Laundry
- Level: Upper
Living room
- Features: Flooring - Carpet, Ceiling Fan(s), Fireplace - Wood Burning
- Level: Main
Sitting room
- Features: Flooring - Carpet
- Level: Upper
Sitting room
- Features: Flooring - Carpet
- Level: Main
Heating
- Heat Pump, Zoned, Electric
Cooling
- Ceiling Fan(s), Central Air, Zoned, Electric
Appliances
- Included: Cooktop, Dishwasher, Dryer, Exhaust Fan, Ice Maker, Oven, Refrigerator, Washer, Water Heater
- Laundry: Dryer In Unit, Washer In Unit, Upper Level, Hookup, Lower Level, Laundry Room
Features
- Upgraded Countertops, Bathroom - Tub Shower, Walk-In Closet(s), Soaking Tub, Bathroom - Stall Shower, Pantry, Ceiling Fan(s), Combination Kitchen/Dining, Dining Area, Kitchen - Gourmet, Primary Bath(s), Dry Wall
- Flooring: Wood, Carpet
- Windows: Bay/Bow, Screens, Skylight(s)
- Basement: Full,Interior Entry,Side Entrance,Unfinished,Walk-Out Access
- Number of fireplaces: 1
- Fireplace features: Wood Burning
Interior area
- Total structure area: 3,337
- Total interior livable area: 3,061 sqft
- Finished area above ground: 3,061
- Finished area below ground: 0
Property
Parking
- Total spaces: 2
- Parking features: Garage Door Opener, Garage Faces Side, Inside Entrance, Driveway, Attached
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: None
Features
- Levels: Four
- Stories: 4
- Patio & porch: Patio, Deck
- Exterior features: Storage
- Pool features: None
- Has view: Yes
- View description: Trees/Woods
Lot
- Size: 2.11 Acres
- Features: Backs to Trees, Front Yard, Level, Rear Yard, SideYard(s), Wooded
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1903052974
- Zoning: RNC
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Brick Front, Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- New construction: No
- Year built: 1995
Utilities & green energy
- Sewer: Private Septic Tank
- Water: Well
- Utilities for property: Cable Available
Community & neighborhood
Security
- Security features: Main Entrance Lock, Smoke Detector(s)
Location
- Region: Leonardtown
- Subdivision: Chestnut Ridge
- Municipality: Unincorporated
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $100 annually
- Association name: CHESTNUT RIDGE COMMUNITY ASSOCIATION
Other
Other facts
- Listing agreement: Exclusive Agency
- Listing terms: Cash,Conventional,FHA,USDA Loan,VA Loan
- Ownership: Fee Simple
- Road surface type: Black Top
Price history
| Date | Event | Price |
|---|---|---|
| 10/30/2025 | Sold | $599,900$196/sqft |
Source:  Bright MLS #MDSM2025274 Report a problem | ||
| 9/30/2025 | Contingent | $599,900$196/sqft |
Source: Bright MLS #MDSM2025274 Report a problem | ||
| 9/16/2025 | Price change | $599,900-2.5%$196/sqft |
Source: Bright MLS #MDSM2025274 Report a problem | ||
| 8/23/2025 | Listed for sale | $615,000$201/sqft |
Source: Bright MLS #MDSM2025274 Report a problem | ||
| 7/10/2025 | Contingent | $615,000$201/sqft |
Source: Bright MLS #MDSM2025274 Report a problem | ||
Public tax history
Tax history is unavailable.
Find assessor info on the county website
Neighborhood: 20650
Nearby schools
GreatSchools rating
- 9/10Piney Point Elementary SchoolGrades: PK-5Distance: 5.1 mi
- 8/10Leonardtown Middle SchoolGrades: 6-8Distance: 3.4 mi
- 5/10Leonardtown High SchoolGrades: 9-12Distance: 3 mi
Schools provided by the listing agent
- Elementary: Piney Point
- Middle: Leonardtown
- High: Leonardtown
- District: St. Mary's 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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