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$564,900 -$10,000 (-1.74%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,594 Sq. Ft.
  • 2 Car Garage
  • Updated 3 days ago
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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 windows 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

Full Property Details for 20753 Chestnut Ridge Dr

General

  • Price: $564,900
  • HOA FEE: $8/month
  • HOA FEE FREQ.: Annually
  • Taxes: $4,471 (2025)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDSM2028218
  • Updated: 1/13/2026
  • Added to Site: 53 day(s) ago

Interior

  • Interior Features: Bathroom - Walk-In Shower, Chair Railings, Crown Moldings, Kitchen - Island, Primary Bath(s), Pantry, Upgraded Countertops, Wood Floors
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Brick, Wood
  • Appliances: Dishwasher, Dryer, Exhaust Fan, Microwave, Oven - Double, Oven/Range - Electric, Refrigerator, Washer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - 1/2 Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 4

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Type: Attached Garage
  • Garage Description: Garage - Front Entry, Garage Door Opener, Inside Access, Oversized

Location

  • County: SAINT MARYS
  • Subdivision: CHESTNUT RIDGE
  • Driving Directions: Rt 5 To Chestnut Ridge Subdivision to property on right

School Information

  • School District: St. Marys County Public Schools
  • Middle School: Leonardtown
  • High School: Leonardtown

Community

  • Association: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s), Heat Pump(s)
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Septic Exists
  • Water: Private

Structural Information

  • Architectural Style: Colonial
  • Structure Type: Detached
  • Construction: Vinyl Siding
  • Foundation: Permanent
  • Stories Description: Main, Upper 1
  • Square Feet: 2,594
  • Sq. Ft. Source: Estimated
  • Living Area: 2,594 Sq. Ft.
  • Finished Above Grnd: 2,594 Sq. Ft.
  • Year Built: 1994
  • Year Built Source: Assessor
  • Property Condition: Excellent

Lot Features

  • Lot Size (Acres): 2
  • Lot Size (Sq. Ft.): 87,120
  • Lot Size Source: Assessor
  • Zoning: RNC

Financial Considerations

  • Price Per Sq. Ft.: $217.77
  • Association Fee: $100
  • Assoc Fee Freq.: Annually
  • Assessment Year: 2025
  • County Tax: $4,471
  • County Tax Freq: Annually
  • Tax w/Assessment: $465,800
  • Tax Amount: $4,471
  • Tax Year: 2025
  • Tax Total Finished Sq. Ft.: 2474

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: 2
  • Lot Number: 55

Listed by CENTURY 21 New Millennium, Tracey L Summers

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Listing agent

— 20753 Chestnut Ridge Dr —

  • Tracey L Summers

    CENTURY 21 New Millennium

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 20753 Chestnut Ridge Dr

School District:St. Marys County Public Schools
NameGradesDistance
Piney Point Elementary School
44550 Tall Timbers Road, Tall Timbers, MD 20690
PK-55.4 mi
Leonardtown Middle School
24015 Point Lookout Road, Leonardtown, MD 20650
6-83.1 mi
Leonardtown High School
23995 Point Lookout Road, Leonardtown, MD 20650
9-122.7 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 20753 Chestnut Ridge Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/13/2026
Price Reduced
$564,900
-1.74%
MLS
11/25/2025
Listed
$574,900
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 20753 Chestnut Ridge Dr

Year
Property Taxes
Change
Tax Assessment
Change
2023
$160
—
$465,800
10%
2023
$160
—
$424,867
11%
2023
$160
-95%
$383,933
12%
2022
$3,292
6%
$343,000
3%
2019
$3,104
1903%
$333,833
3%
2021
$155
1%
$324,667
3%
2020
$153
1%
$315,500
1%
2019
$151
14%
$313,833
1%
2018
$132
—
$312,167
1%
2017
$132
10%
$310,500
—
2016
$120
-96%
$310,500
—
2015
$3,161
21%
$310,500
-6%
2014
$2,612
—
$330,800
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 20753 Chestnut Ridge Dr

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by CENTURY 21 New Millennium, Tracey L Summers

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20753 Chestnut Ridge Drive, Leonardtown, MD 20650 (MLS# MDSM2028218) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 20753 Chestnut Ridge Drive is currently listed for $564,900 and was received on November 25, 2025. Want to learn more about 20753 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.

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