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 acresStep inside and 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 woodsUpstairs, 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 shedBonus! Encapsulated crawlspace w/ commercial grade dehumidifier, sprinkler system, heat pump 2024, new roof 2016
- MD
- Leonardtown
- 20650
- 20753 CHESTNUT RIDGE DRIVE
- MLS# MDSM2028218
- Date Listed11/19/2025
- Days on Realty 5 Days
- Bedrooms 4
- Bathrooms 2 Full baths, 1 Half baths
- Lot Size 2 acres (87,120 sq. ft)
- Sewer Septic Tank
- Subdivision CHESTNUT RIDGE
- Property Type Single Family
- County SAINT MARYS
- Year Built 1994
- Water Private
- Square Feet 2,594 sq. ft
- Price Per Sq. Ft $221.63
Interior Features
- Appliances Double Oven, Electric Range, Electric Oven, Electric Water Heater, Dishwasher, Dryer, Exhaust Fan, Microwave, Refrigerator, Washer
- Flooring Wood
- Cooling Central Air, Heat Pump, Ceiling Fan(s), Electric
- Heating Exhaust Fan, Electric, Heat Pump
Exterior / Lot Features
- Roof -
- Lot Size Acres 2.00
- Lot Size SQFT 87,120.00
- Lot Features -
Directions
Rt 5 To Chestnut Ridge Subdivision to property on right
Financial Considerations
- HOA Fee $100 Annually
- Tax Amount $4,471
- Terms Cash, Conventional, FHA, VA Loan
Nearby Schools
Source: School Digger
Linton Springs Elementary School
Public • PK - 5 • Serves this home
116.54 mi
Distance
Public • 6 - 8 • Serves this home
111.57 mi
Distance
Public • 9 - 12 • Serves this home
114.88 mi
Distance
Linton Springs Elementary School
Public • PK - 5 • Serves this home
116.54 mi
Distance
Parr's Ridge Elementary School
Public • PK - 2
116.65 mi
Distance
Public • PK - 5
120.73 mi
Distance
Public • 6 - 8 • Serves this home
111.57 mi
Distance
Public • 6 - 8
113.61 mi
Distance
Public • 6 - 8
116.65 mi
Distance
Public • 9 - 12 • Serves this home
114.88 mi
Distance
Public • 9 - 12
116.54 mi
Distance
Public • 9 - 12
119.39 mi
Distance
Public • 9 - 12
127.6 mi
Distance
Sales & Tax History
Source: Public Records
| Street Address | Beds | Baths | Sold Date | List Price | Valuation Date | Valuation Price |
|---|---|---|---|---|---|---|
| 23324 SUGAR PINE LN | 3 | 3 | Oct 22, 2025 | $378,380 | Nov 25, 2025 | - |
| 40552 BRETON KNOLLS CT | Listing | 4 | 5 | Sep 29, 2025 | $884,900 | Mar 12, 2021 | $399,200 |
| 24142 ALICE SPRING LANE | Listing | 4 | 3 | Oct 01, 2025 | $673,634 | Nov 25, 2025 | - |
| 19106 WINDSOR COURT | Listing | 4 | 4 | Oct 17, 2025 | $794,905 | Mar 12, 2021 | $97,920 |
| 24190 ALICE SPRING LANE | Listing | 4 | 3 | Oct 15, 2025 | $669,900 | Nov 25, 2025 | - |
| 45867 BROUN TERRACE | Listing | 6 | 3 | Nov 04, 2025 | $330,000 | Mar 21, 2024 | $409,126 |
| 19172 PORTO BELLO LN | Listing | 4 | 4 | Nov 04, 2025 | $717,583 | Dec 12, 2022 | $235,800 |
| 23348 LINDSAY DRIVE | 5 | 4 | Oct 16, 2025 | $599,900 | Nov 25, 2025 | - |
| 41505 KNIGHT ROAD | 5 | 8 | Oct 08, 2025 | $5,950,000 | Nov 25, 2025 | - |
| 44140 OUTRIGGER WAY | 1 | 2 | Nov 13, 2025 | $249,900 | Nov 25, 2025 | - |
Population & Environment
Source: Sperling's Best Places
| Zip | City | County | National | |
|---|---|---|---|---|
| Population | 16,602 | 4,342 | 117,169 | 335,858,263 |
| Population Density | 270 | 1,054 | 328 | 95 |
| People per Household | 2.7 | 2.5 | 2.7 | 2.6 |
| Median Age | 41.5 | 38.6 | 38.5 | 39.1 |
| Median Income | $105,327 | $91,807 | $94,048 | $66,222 |
| Average Income | $47,970 | $43,731 | $40,662 | $35,475 |
| Cost of Living Index | 115 | 104 | 114 | 100 |
| Zip | City | County | National | |
|---|---|---|---|---|
| January Avg. High Temp | 26.3°F | 27.31°F | 27.31°F | 22.6°F |
| July Avg. High Temp | 86.1°F | 86.1°F | 86.1°F | 86.2°F |
| Annual Precipitation | 47.52" | 45.58" | 45.58" | 38" |
22/100
Bikable
Bike Score ®
Overview
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.Walkability averages in the surrounding area
The average walkability score in the surrounding area is Walk Score: 2/100, Transit Score: 0/100, Bike Score: 22/100.
Property Change History
Points of Interest near 20753 CHESTNUT RIDGE DRIVE, LEONARDTOWN, MD 20650
1.47 mi
Distance
1.62 mi
Distance
1.75 mi
Distance
1.81 mi
Distance
1.83 mi
Distance
1.98 mi
Distance
2.01 mi
Distance
2.12 mi
Distance
7.25 milepost, St. Mary's County, MD, USA
Government
2.26 mi
Distance
Saint Mary's Lake, St. Mary's County, MD, USA
Natural • Recreation
2.2 mi
Distance
Blake Creek, St. Mary's County, MD, USA
Natural • Recreation
2.35 mi
Distance
Flood Creek, St. Mary's County, MD, USA
Natural • Recreation
2.37 mi
Distance
Saint Mary's Lake, St. Mary's County, MD, USA
Natural • Recreation
2.2 mi
Distance
Blake Creek, St. Mary's County, MD, USA
Natural • Recreation
2.35 mi
Distance
Flood Creek, St. Mary's County, MD, USA
Natural • Recreation
2.37 mi
Distance
2.6 mi
Distance
1.03 mi
Distance
1.63 mi
Distance
0.53 mi
Distance
1.49 mi
Distance
1.59 mi
Distance
1.63 mi
Distance
2.62 mi
Distance
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Frequently Asked Questions for 20753 CHESTNUT RIDGE DRIVE
Source: Realty.com
20753 CHESTNUT RIDGE DRIVE, LEONARDTOWN, MD 20650 is a Single Family 2,594 sq. ft. home listed for sale. Realty.com has 0 photos available of this 4 bed, 3 bath house, listed at $574,900. View sales and tax history, use our mortgage calculator and more on Realty.com
Our records indicate that 20753 CHESTNUT RIDGE DRIVE was built in 1994.
The full address for this home is 20753 CHESTNUT RIDGE DRIVE, LEONARDTOWN, MD 20650.
20753 CHESTNUT RIDGE DRIVE has been listed on Realty.com since Wed November 19, 2025
Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.
The average walkability score in the surrounding area is Walk Score: 2/100, Transit Score: 0/100, Bike Score: 22/100.
There are 3 schools assigned to this home. Check out the schools near 20753 CHESTNUT RIDGE DRIVE. Linton Springs Elementary School (Grades: PK - 5), Sykesville Middle School (Grades: 6 - 8), Liberty High School (Grades: 9 - 12)
Listing provided courtesy of:
Century 21 New Millennium
(tel: 301-862-2169)
Listing agent:
Tracey Summers
(tel: 240-298-8917)
(#149739)
This content last refreshed on 2025-11-25 00:57:28. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.
Export listing data of 20753 CHESTNUT RIDGE DRIVE, LEONARDTOWN, MD 20650 : MLS# MDSM2028218