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$599,900
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Property Description
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
Full Property Details
Full Property Details for 20591 Chestnut Ridge Dr
General
- Sold For: $599,900
- HOA FEE: $8/month
- HOA FEE FREQ.: Annually
- Taxes: $3,880 (2020)
- Status: Closed
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDSM2025274
- Added to Site: 234 day(s) ago
Interior
- Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Sitting Room, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Kitchen, Basement, Foyer, Laundry, Primary Bathroom, Full Bath, Half Bath
- Interior Features: Upgraded Countertops, Wood Floors, Carpet, Bathroom - Tub Shower, Walk-in Closet(s), Bathroom - Soaking Tub, Bathroom - Stall Shower, Pantry, Ceiling Fan(s), Combination Kitchen/Dining, Dining Area, Kitchen - Gourmet, Primary Bath(s)
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Wood, Wood
- Appliances: Cooktop, Dishwasher, Dryer, Exhaust Fan, Icemaker, Oven - Wall, Refrigerator, Washer
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
- Upper 2 - Full Baths: 1
- Upper Floor Baths: 3
- Upper - Full Baths: 3
- Main Floor Baths: 1
- Main - 1/2 Baths: 1
- Primary Bathroom: Primary Bathroom - B, Upper 1
Bedrooms
- Total Bedrooms: 5
- Bedrooms Upper: 5
- Bedrooms-Up2: 2
- Primary Bedroom: Primary Bedroom - Flooring - Carpet, Ceiling Fan(s), Walk-In Closet(s), Upper 1
- Bedroom 1: Bedroom 4 - Flooring - Carpet, Ceiling Fan(s), Upper 2
- Bedroom 2: Bedroom 5 - Flooring - Carpet, Ceiling Fan(s), Upper 2
- Bedroom 3: Bedroom 2 - Flooring - Carpet, Ceiling Fan(s), Upper 1
- Bedroom 4: Bedroom 3 - Flooring - Carpet, Ceiling Fan(s), Upper 1
Other Rooms
- Foyer/Entry: Foyer, Main
- Living Room: Living Room - Flooring - Carpet, Ceiling Fan(s), Fireplace - Wood Burning, Main
- Sitting Room: Sitting Room - Flooring - Carpet, Upper 1
- Kitchen: Kitchen - Countertop(s) - Granite, Flooring - HardWood, Island, Kitchen - Propane Cooking, Pantry, Main
- Dining Room: Dining Room - Flooring - HardWood, Main
- Laundry: Dryer In Unit, Washer In Unit, Upper Floor, Hookup, Lower Floor, Upper 1
Additional Information
- Security/Safety: Main Entrance Lock, Smoke Detector
Exterior
- Exterior Features: Secure Storage
- Porch/Patio/Deck: Patio(s), Deck(s)
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 2
- Parking Features: Paved Driveway
- Parking Type: Driveway, Attached Garage
- Garage Description: Garage Door Opener, Garage - Side Entry, Inside Access
Location
- Municipality: Unincorporated
- County: Saint Marys
- Development Name: Chestnut Ridge
- Subdivision: Chestnut Ridge
- Driving Directions: GPS is correct
School Information
- School District: St. Mary's County Public Schools
- Elementary School: Piney Point
- Middle School: Leonardtown
- High School: Leonardtown
Community
- Association: Yes
- Assoc. Name: CHESTNUT RIDGE COMMUNITY ASSOCIATION
- Pets Allowed: Yes
- Pets: No Pet Restrictions
Heating & Cooling
- Central air: Yes
- Cooling Type: Ceiling Fan(s), Central A/C, Zoned
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s), Zoned
- Heating Fuel: Electric
- Water Heater: Propane
Utilities
- Sewer: Private Septic Tank
- Water: Well
- Utility Description: Cable TV Available
Structural Information
- Architectural Info: Colonial
- Architectural Style: Colonial
- Structure Type: Detached
- Construction: Brick Front, Vinyl Siding
- Basement: Yes
- Basement Entrance: Yes
- Basement Desc.: Full, Interior Access, Side Entrance, Unfinished, Walkout Level
- Foundation: Concrete Perimeter
- Roof: Shingle
- Walls/Ceilings: Dry Wall
- Windows: Bay/Bow, Screens, Skylights
- Stories/Levels: 0
- Stories Description: Main, Upper 1, Upper 2
- Square Feet: 3,337
- Sq. Ft. Source: Estimated
- Living Area: 3,061 Sq. Ft.
- Unfin. Above Grnd: 276 Sq. Ft.
- Year Built: 1995
- Year Built Source: Assessor
Additional Structures
- Other Structures: Shed
Lot Features
- Property View: Trees/Woods
- Lot Size (Acres): 2.11
- Lot Size (Sq. Ft.): 91,912
- Lot Size Source: Assessor
- Street/Road Desc.: Black Top
- Lot Features: Backs to Trees, Front Yard, Level, Rear Yard, SideYard(s), Trees/Wooded
- Zoning: RNC
- Lot Description: Backs to Trees, Front Yard, Level, Rear Yard, SideYard(s), Trees/Wooded
Financial Considerations
- Price Per Sq. Ft.: $195.98
- Association Fee: $100
- Assoc Fee Freq.: Annually
- Assessment Year: 2021
- City/TownTax Freq: Annually
- County Tax: $3,520
- County Tax Freq: Annually
- Tax w/Assessment: $396,900
- Tax Amount: $3,880
- Tax Year: 2020
- Terms: Standard Sale
- Tax Total Finished Sq. Ft.: 3061
Disclosures and Reports
- Ownership: Fee Simple
- Section: 4
- Lot Number: 92
Listed by EXP Realty, LLC, Lauren Coble Garner
Sold by Infinitas Realty Group, Matthew A Burgan
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Schools
Schools serving 20591 Chestnut Ridge Dr
School District:St. Marys County Public Schools
| Name | Grades | Distance |
|---|---|---|
Piney Point Elementary School 44550 Tall Timbers Road, Tall Timbers, MD 20690 | PK-5 | 5.1 mi |
Leonardtown Middle School 24015 Point Lookout Road, Leonardtown, MD 20650 | 6-8 | 3.4 mi |
Leonardtown High School 23995 Point Lookout Road, Leonardtown, MD 20650 | 9-12 | 3 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 20591 Chestnut Ridge Dr
Date
Details
Price
Change
Source
10/30/2025
Sold
$599,900
—
MLS
9/16/2025
Price Reduced
$599,900
-2.46%
MLS
6/28/2025
Listed
$615,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
20591 Chestnut Ridge Drive, Leonardtown, MD 20650 (MLS# MDSM2025274) is a Single Family property that was sold at $599,900 on October 30, 2025. Want to learn more about 20591 Chestnut Ridge Drive? Do you have questions about finding other Single Family real estate for sale in Leonardtown? You can browse all Leonardtown real estate or contact a Coldwell Banker agent to request more information.

