$574,900
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20753 Chestnut Ridge Drive, Leonardtown, MD 20650

4 Beds
3 Baths
2,594 Sq Ft

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

  • 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 -

Financial Considerations

  • HOA Fee $100 Annually
  • Tax Amount $4,471
  • Terms Cash, Conventional, FHA, VA Loan

Nearby Schools

Source: School Digger

Sales & Tax History

Source: Public Records

Population & Environment

Source: Sperling's Best Places

Walkability in MD / 20650

Source: Walkscore

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

Property description updated with new details

Points of Interest near 20753 CHESTNUT RIDGE DRIVE, LEONARDTOWN, MD 20650

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