Pending
Sale Pending at 20753 Chestnut Ridge Dr, Leonardtown, MD 20650 | MLS# MDSM2028218 | Listing updated on 2026-02-24
Photo 1 of Sale Pending at 20753 Chestnut Ridge Dr, Leonardtown, MD 20650 | MLS# MDSM2028218 | Listing updated on 2026-02-24
Photo 2 of Sale Pending at 20753 Chestnut Ridge Dr, Leonardtown, MD 20650 | MLS# MDSM2028218 | Listing updated on 2026-02-24
Photo 3 of Sale Pending at 20753 Chestnut Ridge Dr, Leonardtown, MD 20650 | MLS# MDSM2028218 | Listing updated on 2026-02-24
Photo 4 of Sale Pending at 20753 Chestnut Ridge Dr, Leonardtown, MD 20650 | MLS# MDSM2028218 | Listing updated on 2026-02-24
41+
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Street View

$564,900

Monthly Est:$2,812

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,594sqft

20753 Chestnut Ridge Dr, Leonardtown, MD 20650

$2,812/moEst:

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  • Single Family Residence

  • Built in 1994

  • $8.33/mo HOA

  • 2 acres lot

  • $218/sq.ft

Description

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 acres. Quality construction throughout from the sunroom to the kitchen remodel you will see the workmanship!
Once inside you will 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 window
s inviting the outside in. Connecting deck overlooking your own peaceful woods

Upstairs, 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 shed

Bonus! Encapsulated crawlspace w/ commercial grade dehumidifier, sprinkler system, heat pump 2024, new roof 2016

  • Houzeo last checked: 13 minutes ago
  • Listing updated: February 24, 2026 at 11:45 pm
  • Listing Provided by: Tracey L Summers (240) 298-8917 | CENTURY 21 New Millennium (301) 862-2169
  • Source: Bright MLS-NJ | MLS#: MDSM2028218 Bright MLS-NJ

Property Details

  • Status

    Pending

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Saint Marys Md County

  • City

    Leonardtown

  • Neighborhood

    --

  • Year Built

    1994

  • HOA Fees

    $8.33/mo

  • Finished Area

    2,594 sqft

  • Lot Size

    2 acres lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDSM2028218

  • MLS Status

    PENDING-BRIGHT

  • Days on Market

    58

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Location

HOA Management

N/A

HOA Fees

$100/ Annually

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 3

Interior

  • Appliances

    Dishwasher, Dryer, Exhaust Fan, Microwave, Oven Double, Oven/range Electric, Refrigerator, Washer

  • Interior Features

    Bathroom Walk In Shower, Chair Railings, Crown Moldings, Kitchen Island, Primary Bath(s), Pantry, Upgraded Countertops, Wood Floors

  • Heating

    Heat Pump(s)

  • Sewer

    Septic Exists

  • Cooling

    Central A/c, Ceiling Fan(s), Heat Pump(s)

Construction

  • Year Built

    Year Built: 1994

  • Home type

    Single Family Residence

  • Construction Materials

    Vinyl Siding

  • Architectural Style

    Colonial

  • Property Condition

    Excellent

  • Foundation Details

    Permanent

Utilities & Energy

  • Fireplace Features

    Brick, Wood

  • Water Source

    Private

Other Features

  • Subdivision Name

    Chestnut Ridge

Price History

DateEventPrice

01/21/2026

Source: mls_logoBright MLS-NJ #MDSM2028218

Pending

$564,900

$218/sqft

01/13/2026

Source: mls_logoBright MLS-NJ #MDSM2028218

Price Decreased

$564,900 -1.74%

$218/sqft

11/25/2025

Source: mls_logoBright MLS-NJ #MDSM2028218

Listed for Sale

$574,900

$222/sqft

Nearby Homes

Based on information from Bright MLS through Nov 04, 2026, 12:30AM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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