20753 Chestnut Ridge Dr

Leonardtown, MD 20650

$574,900
Price
4
Beds
2,594 Sq. Ft.
$222 / Sq. Ft.
2,594
Sq. Ft.
$222
per Sq. Ft.
a front view of a house with a yard
a front view of a house with a yard and garage
a front view of a house with garden
a front view of a house with garden
a living room with furniture and a chair
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture and wooden floor
a view of a dining room with furniture and wooden floor
a kitchen with stainless steel appliances granite countertop a sink a microwave counter space and cabinets
a kitchen with stainless steel appliances granite countertop a kitchen island a stove a refrigerator a sink and a microwave
a view of empty room with a fireplace
a living room with furniture and a large window
a living room with furniture and a large window
a living room with furniture and a large window
a view of an empty room with wooden floor and a bathroom
a bedroom with a bed and dresser with mirror
a bedroom with a bed and a lamp on dresser
a bedroom with a bed and dresser with mirror
a white toilet sitting next to a bath tub
a bathroom with a double vanity sink and a mirror
a bathroom with a granite countertop sink and a mirror
a bedroom with a bed and a chair
a bathroom with a sink and toilet
a bed sitting in a bedroom next to a window
a large bed sitting in a bedroom next to a window
a front view of a house with a yard
a front view of a house with a yard
a front view of a house with a yard

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
Step 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...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
Step 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 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
  1. Listed by Tracey L Summers • CENTURY 21 New Millennium
    P: (240)-298-8917 tracey.summers@c21nm.com

Property Details for 20753 Chestnut Ridge Drive

Tax ID Number
1903048489
Ownership
Fee Simple
Condo Coop Association
No
HOA
Yes
Structure Type
Detached
Style
Colonial
Levels/Stories
2
Waterfront
No
LISTING UPDATED: 11/25/2025 05:08 PM

Property Details for 20753 Chestnut Ridge Drive

StatusActive
MLS #MDSM2028218
Days on Market33
Taxes$4,471 / year
HOA Fees$100 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Fee Simple
Year Built1994
Lot Size2.00 AC / 87,120 SF
CountySt. Mary's County

Location

Listing Courtesy of CENTURY 21 New Millennium
Add your commute

Building Information for 20753 Chestnut Ridge Drive

Stories2Year Built1994Building Size-Lot Size2.00 AC / 87,120 SF

Payment Calculator

$3,222 per month

30 year fixed, 6.28% Interest

Principal and Interest

$2,841

Property Taxes

$373

HOA Dues

$8

The Payment Calculator is for illustrative purposes only.

Property Information for 20753 Chestnut Ridge Drive

Location
Location
  • In City Limits: No
  • School District Name: ST. MARYS COUNTY PUBLIC SCHOOLS
  • School District County ID: 803197649142
  • SchoolDistrictSource: 3rd Party
  • Middle Or Junior School: LEONARDTOWN (SAINT MARYS MD)
  • MiddleSchoolSource: 3rd Party
  • High School: LEONARDTOWN (SAINT MARYS MD)
  • HighSchoolSource: 3rd Party
  • County: SAINT MARYS
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: No
  • Water Oriented: No
  • Navigable Water: No
  • Tidal Water: No
  • Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
  • Senior Community: No
  • Type of Condo: Home Owner Association
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2025
  • Tax Assessed Value: $465,800
  • Year Assessed: 2025
  • County Tax: $4,471
  • Improvement Assessed Value: $340,800
  • Land Assessed Value: $125,000
  • Clean Green Assessed: No
  • Land Use Code: E
  • Section: 2
  • Zoning: RNC
  • Tax Lot: 55
  • School Tax: $0
  • Tax Page Number: 118
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 0
  • # Bathrooms Count Main Level: 1
  • # Bathrooms Full Main Level: 0
  • # Bathrooms Half Main Level: 1
All Upper Levels
  • # Bedrooms Count All Upper Levels: 4
  • # Bathrooms Count All Upper Levels: 2
  • # Bathrooms Full All Upper Levels: 2
Upper Level 1
  • # Bedrooms Count Upper Level: 4
  • # Bathrooms Count Upper Level: 2
  • # Bathrooms Full Upper Level: 2
Rooms
  • Stories: Main, Upper 1
Building Info
Building Info
  • Total Finished SQFT: 2,594.00
  • Total Finished SQFT Source: Estimated
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Parcel ID: 14990558
Parking
Parking
  • Type Of Parking: Attached Garage
  • Num of Attached Garage Spaces: 2
  • Total Garage Spaces: 2
  • Garage Features: Garage - Front Entry, Garage Door Opener, Inside Access, Oversized
Interior Features
Interior Features
  • Interior Features: Bathroom - Walk-In Shower, Chair Railings, Crown Moldings, Kitchen - Island, Primary Bath(s), Pantry, Upgraded Countertops, Wood Floors
  • Fireplace: Yes
  • Fireplaces Count: 1
  • Fireplace Features: Brick, Wood
  • Appliances: Dishwasher, Dryer, Exhaust Fan, Microwave, Oven - Double, Oven/Range - Electric, Refrigerator, Washer
  • Accessibility Features: None
Exterior Features
Exterior Features
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s), Heat Pump(s)
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s)
  • Heating Fuel: Electric
  • Hot Water: Electric
  • Water Source: Private
  • Sewer Septic: Septic Exists
Confidential Data
Listing Office
  • List Agent AOR: Southern Maryland Association of REALTORS

Property History for 20753 Chestnut Ridge Drive

DateEvent & SourcePriceAppreciation
Nov 25, 2025

Listed (Active)

BRIGHT #MDSM2028218

$574,900—
DateEvent & SourcePrice
11/25/2025

Listed (Active)

BRIGHT #MDSM2028218

$574,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 20753 Chestnut Ridge Drive

Taxable ValueLand$125,000Additions$340,800Total$465,800
Tax Record2023$160 ($13 / month)
Home Facts
Beds0Baths2.5Total Finished SqFt2,474 SqFtAbove Grade Finished SqFt2,474 SqFtStories2Lot Size87,120 SqFtStyleSingle Family ResidenceYear Built1994ZoningRNCCountyST. MARY'SAPN03-048489Fireplace TypeHas Fireplace

Schools near 20753 Chestnut Ridge Drive

This home is within St. Mary's County Public Schools.
Rating
School
Type
Grades
Distance
Piney Point Elementary School
Public - PK to 5
Leonardtown Middle School
Public - 6 to 8
Leonardtown High School
Public - 9 to 12
Chesapeake Charter School
Charter - K to 8
Rating
School
Distance
Piney Point Elementary School
PublicPK to 5

Leonardtown Middle School
Public6 to 8

Leonardtown High School
Public9 to 12

Chesapeake Charter School
CharterK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 20753 Chestnut Ridge Drive, Leonardtown, MD 20650

20753 Chestnut Ridge Drive is a single family home for sale in Leonardtown, MD 20650. This property was listed for sale on November 25, 2025 by CENTURY 21 New Millennium, it's currently listed at $574,900. This listing's school district is St. Mary's County Public Schools. Nearby schools include Piney Point Elementary School, Leonardtown Middle School and Leonardtown High School. 20753 Chestnut Ridge Drive is a 4-bed, 3-bath, 2,594 sqft single family home built in 1994.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of CENTURY 21 New Millennium

© 2025 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 11/25/2025 05:08 PM