20591 Chestnut Ridge Dr Leonardtown, MD 20650
Estimated payment $3,499/month
Highlights
- Gourmet Kitchen
- View of Trees or Woods
- Colonial Architecture
- Piney Point Elementary School Rated 9+
- 2.11 Acre Lot
- Deck
About This Home
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
Open House Schedule
-
Sunday, September 21, 202512:00 to 2:00 pm9/21/2025 12:00:00 PM +00:009/21/2025 2:00:00 PM +00:00Add to Calendar
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $3,880
Year Built
- Built in 1995
Lot Details
- 2.11 Acre Lot
- Level Lot
- Wooded Lot
- Backs to Trees or Woods
- Back, Front, and Side Yard
- Property is zoned RNC
HOA Fees
- $8 Monthly HOA Fees
Parking
- 2 Car Direct Access Garage
- Side Facing Garage
- Garage Door Opener
- Driveway
Home Design
- Colonial Architecture
- Shingle Roof
- Vinyl Siding
- Brick Front
- Concrete Perimeter Foundation
Interior Spaces
- Property has 4 Levels
- Ceiling Fan
- Skylights
- Wood Burning Fireplace
- Bay Window
- Window Screens
- Entrance Foyer
- Sitting Room
- Living Room
- Combination Kitchen and Dining Room
- Views of Woods
- Fire and Smoke Detector
Kitchen
- Gourmet Kitchen
- Built-In Oven
- Cooktop
- Ice Maker
- Dishwasher
- Upgraded Countertops
Flooring
- Wood
- Carpet
Bedrooms and Bathrooms
- 5 Bedrooms
- En-Suite Primary Bedroom
- En-Suite Bathroom
- Walk-In Closet
- Soaking Tub
- Bathtub with Shower
- Walk-in Shower
Laundry
- Laundry Room
- Laundry on lower level
- Dryer
- Washer
Unfinished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
- Interior and Side Basement Entry
Outdoor Features
- Deck
- Patio
- Shed
Schools
- Piney Point Elementary School
- Leonardtown Middle School
- Leonardtown High School
Utilities
- Forced Air Zoned Heating and Cooling System
- Heat Pump System
- Vented Exhaust Fan
- Well
- Propane Water Heater
- Septic Tank
- Cable TV Available
Community Details
- Chestnut Ridge Community Association
- Chestnut Ridge Subdivision
Listing and Financial Details
- Tax Lot 92
- Assessor Parcel Number 1903052974
Map
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $5,238 | $527,400 | $125,500 | $401,900 |
| 2024 | $5,238 | $483,900 | $0 | $0 |
| 2023 | $4,638 | $440,400 | $0 | $0 |
| 2022 | $4,194 | $396,900 | $125,500 | $271,400 |
| 2021 | $3,960 | $381,833 | $0 | $0 |
| 2020 | $3,843 | $366,767 | $0 | $0 |
| 2019 | $3,729 | $351,700 | $115,500 | $236,200 |
| 2018 | $3,727 | $351,700 | $115,500 | $236,200 |
| 2017 | $3,708 | $351,700 | $0 | $0 |
| 2016 | -- | $360,900 | $0 | $0 |
| 2015 | $3,842 | $360,900 | $0 | $0 |
| 2014 | $3,842 | $360,900 | $0 | $0 |
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 09/16/2025 09/16/25 | Price Changed | $599,900 | -2.5% | $196 / Sq Ft |
| 06/28/2025 06/28/25 | For Sale | $615,000 | 0.0% | $201 / Sq Ft |
| 07/09/2022 07/09/22 | Rented | $3,000 | -6.3% | -- |
| 06/06/2022 06/06/22 | For Rent | $3,200 | 0.0% | -- |
| 08/03/2021 08/03/21 | Sold | $535,000 | 0.0% | $175 / Sq Ft |
| 07/21/2021 07/21/21 | Pending | -- | -- | -- |
| 07/21/2021 07/21/21 | For Sale | $535,000 | -- | $175 / Sq Ft |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $535,000 | Southern Maryland Title | |
| Interfamily Deed Transfer | -- | National Title Network | |
| Deed | $425,000 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $362,416 | VA | |
| Previous Owner | $442,015 | VA | |
| Previous Owner | $433,630 | VA | |
| Previous Owner | $436,950 | VA | |
| Previous Owner | $50,000 | Stand Alone Second | |
| Closed | -- | No Value Available |
Source: Bright MLS
MLS Number: MDSM2025274
APN: 03-052974
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