$525,000
PENDING

20755 Deer Wood Park Dr Leonardtown, MD 20650

Estimated payment $3,221/month

Total Views 8,703
4 Beds
2.5 Baths
2,538 Sq Ft
$207 Price per Sq Ft

Highlights

  • Private Pool
  • Colonial Architecture
  • 2 Car Attached Garage
  • Leonardtown Middle School Rated A-
  • 1 Fireplace
  • Heat Pump System

About This Home

Welcome to your dream home in the desirable Chestnut Hills community of Leonardtown, Maryland! This charming 4-bedroom, 2.5-bathroom single-family home offers a perfect blend of space, comfort, and privacy, all set on an impressive 4.24 acres. With 2,538 square feet of living space, this residence features beautiful hardwood floors throughout, adding a warm and inviting touch.

The heart of the home is the spacious eat-in kitchen, perfect for gatherings and culinary adventures. Cozy up on chilly evenings by the gas fireplace, creating a welcoming atmosphere for family and friends. Step outside to enjoy your own private oasis, complete with a refreshing pool, ideal for summer fun and relaxation.

Conveniently located just minutes from downtown Leonardtown, Patuxent River Naval Air Station, and the scenic Solomon’s Island, you'll have easy access to dining, shopping, and recreational activities. The property also includes a generous 2-car garage, providing ample storage and parking options.

While this home shows well, it does require some TLC to transform it into your perfect oasis. Don’t miss out on this incredible opportunity to create lasting memories in a beautiful setting! Schedule your private showing today!

Listing Agent

Ebon Jackson

EbonAries Realty Group, LLC. License #580937 Listed on: 06/27/2025

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $4,058

Year Built

  • Built in 1996

Lot Details

  • 4.24 Acre Lot
  • Property is zoned RNC

HOA Fees

  • $22 Monthly HOA Fees

Parking

  • 2 Car Attached Garage
  • Side Facing Garage

Home Design

  • Colonial Architecture
  • Slab Foundation
  • Vinyl Siding

Interior Spaces

  • 2,538 Sq Ft Home
  • Property has 2 Levels
  • 1 Fireplace

Bedrooms and Bathrooms

  • 4 Bedrooms

Pool

  • Private Pool

Utilities

  • Heat Pump System
  • Heating System Powered By Leased Propane
  • Well
  • Electric Water Heater
  • Septic Tank

Community Details

  • Chestnut Hills Subdivision

Listing and Financial Details

  • Tax Lot 17
  • Assessor Parcel Number 1902033577

Home Details

Home Type

Single Family

Est. Annual Taxes

$4,058

Year Built

Built in 1996

Lot Details

0

HOA Fees

$22 per month

Parking

2

Listing Details

  • Property Type: Residential
  • Structure Type: Detached
  • Architectural Style: Colonial
  • Ownership: Fee Simple
  • New Construction: No
  • Story List: Main, Upper 1
  • Year Built: 1996
  • Automatically Close On Close Date: No
  • Remarks Public: Welcome to your dream home in the desirable Chestnut Hills community of Leonardtown, Maryland! This charming 4-bedroom, 2.5-bathroom single-family home offers a perfect blend of space, comfort, and privacy, all set on an impressive 4.24 acres. With 2,538 square feet of living space, this residence features beautiful hardwood floors throughout, adding a warm and inviting touch. The heart of the home is the spacious eat-in kitchen, perfect for gatherings and culinary adventures. Cozy up on chilly evenings by the gas fireplace, creating a welcoming atmosphere for family and friends. Step outside to enjoy your own private oasis, complete with a refreshing pool, ideal for summer fun and relaxation. Conveniently located just minutes from downtown Leonardtown, Patuxent River Naval Air Station, and the scenic Solomon’s Island, you'll have easy access to dining, shopping, and recreational activities. The property also includes a generous 2-car garage, providing ample storage and parking options. While this home shows well, it does require some TLC to transform it into your perfect oasis. Don’t miss out on this incredible opportunity to create lasting memories in a beautiful setting! Schedule your private showing today!
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Fireplaces Count: 1
  • Fireplace: Yes
  • Foundation Details: Slab
  • Levels Count: 2
  • Basement: No
  • Total Sq Ft: 2538
  • Living Area Sq Ft: 2538
  • Price Per Sq Ft: 206.86
  • Above Grade Finished Sq Ft: 2538
  • Above Grade Finished Area Units: Square Feet
  • Street Number Modifier: 20755

Beds/Baths

  • Bedrooms: 4
  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Main Level Bathrooms: 1.00
  • Upper Level Bathrooms: 2
  • Upper Level Bathrooms: 2.00
  • Upper Level Full Bathrooms: 2
  • Main Level Half Bathrooms: 1

Exterior Features

  • Other Structures: Above Grade, Below Grade
  • Construction Materials: Vinyl Siding
  • Water Access: No
  • Waterfront: No
  • Water Oriented: No
  • Pool: Yes - Personal
  • Tidal Water: No
  • Water View: No

Garage/Parking

  • Garage Spaces: 2.00
  • Garage: Yes
  • Garage Features: Garage - Side Entry
  • Attached Garage Spaces: 2
  • Total Garage And Parking Spaces: 2
  • Type Of Parking: Attached Garage

Utilities

  • Central Air Conditioning: No
  • Cooling Fuel: Electric
  • Cooling Type: Heat Pump(s)
  • Heating Fuel: Electric, Propane - Leased
  • Heating Type: Heat Pump(s)
  • Heating: Yes
  • Hot Water: Electric
  • Sewer/Septic System: Private Septic Tank
  • Water Source: Well

Condo/Co-op/Association

  • HOA Fees: 259.00
  • HOA Fee Frequency: Annually
  • Condo Co-Op Association: No
  • HOA: Yes
  • Senior Community: No

Schools

  • School District: ST. MARY'S COUNTY PUBLIC SCHOOLS
  • School District Key: 121138839208
  • School District Source: Listing Agent

Lot Info

  • Land Use Code: E
  • Lot Size Acres: 4.24
  • Lot Size Units: Square Feet
  • Lot Sq Ft: 184694.00
  • Year Assessed: 2025
  • Zoning: RNC
  • In City Limits: No

Rental Info

  • Vacation Rental: No

Tax Info

  • Tax Annual Amount: 4058.00
  • Assessor Parcel Number: 1902033577
  • Tax Lot: 17
  • Tax Total Finished Sq Ft: 2538
  • County Tax Payment Frequency: Annually
  • Tax Year: 2024

MLS Schools

  • School District Name: ST. MARY'S COUNTY PUBLIC SCHOOLS

Map

Range of Values:

Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

Not Available

Collateral Analytics does not have data for the current month. Please view the chart for historical values.

ICE

ICE Mortgage Technology ICE Mortgage Technology’s AVM (Automated Valuation Model) is a state-of-the-art online residential property valuation tool that provides a quick and accurate estimate of the value of almost any home in the U.S.

Not Available

ICE Mortgage Technology does not have data for the current month. Please view the chart for historical values.

First American

First American First American Data & Analytics’ next-generation AVM combines unrivaled data assets with a blended ensemble of valuation models to produce highly accurate, reliable valuations you can trust.

Not Available

First American does not have data for the current month. Please view the chart for historical values.

Quantarium

Quantarium Quantarium’s valuation service, repeatedly proven the industry’s most accurate and comprehensive, is supercharged with a self-learning and auto-tuning AI engine that continually becomes smarter and more accurate as it processes daily inputs from the industry’s leading RE data lake.

Not Available

Quantarium does not have data for the current month. Please view the chart for historical values.

Average Value
Not Available
List Price
Sold Price
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $162 $445,100 $136,200 $308,900
2024 $162 $422,767 $0 $0
2023 $160 $400,433 $0 $0
2022 $158 $378,100 $136,200 $241,900
2021 $157 $372,300 $0 $0
2020 $155 $366,500 $0 $0
2019 $153 $360,700 $136,200 $224,500
2018 $151 $360,700 $136,200 $224,500
2017 $132 $360,700 $0 $0
2016 -- $369,600 $0 $0
2015 -- $369,600 $0 $0
2014 $90 $369,600 $0 $0
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/07/2025 07/07/25 Pending -- -- --
06/27/2025 06/27/25 For Sale $525,000 -- $207 / Sq Ft
Source: Bright MLS

Purchase History

Date Type Sale Price Title Company
Deed $48,900 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Closed $39,120 No Value Available
Source: Public Records

Similar Homes in Leonardtown, MD

  • 20798 Waterside Dr, Leonardtown, MD 20650

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,018 Sq Ft
    • 20798 Waterside Dr
    • Leonardtown, MD

    Investor Alert! Stunning Waterfront Opportunity on the Potomac River. Discover the perfect waterfront retreat with breathtaking views of the Potomac River! Currently operating as a successful Airbnb, this property offers a unique opportunity to build your dream home while residing in the charming existing cottage. Step into your backyard and immerse yourself in waterfront living—whether it’s

    Connie Fitzgerald RE/MAX Closers

    Section Image
  • 40534 Miss Ettas Way, Leonardtown, MD 20650

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 1,770 Sq Ft
    • 40534 Miss Ettas Way
    • Leonardtown, MD

    Welcome home to this beautifully maintained Cape Cod built by Hallmark Homes in 2016, situated on a peaceful 1.98-acre lot! Relax on the inviting front porch and take in the tranquil surroundings. Inside, you'll find a spacious living and dining room combo, perfect for entertaining. The kitchen features granite countertops, stainless steel appliances, and a walk-in pantry—ideal for any home

    Connie Fitzgerald RE/MAX Closers

    Section Image
  • 20814 Deer Wood Park Dr, Leonardtown, MD 20650

    $589,000

    • 4 Beds
    • 2.5 Baths
    • 3,412 Sq Ft
    • 20814 Deer Wood Park Dr
    • Leonardtown, MD

    This spacious 4-bedroom Colonial offers the perfect blend of charm, comfort, and privacy on a beautifully treed 4 acre lot. The first floor features a private office/den, formal living room, and elegant dining room. The large kitchen includes a cozy breakfast nook and opens to a step-down family room with a slider leading to a screened-in porch—ideal for indoor-outdoor living.Upstairs,

    Cynthia Crispell CENTURY 21 New Millennium

    Section Image
  • 43571 Bayberry Ct, Leonardtown, MD 20650

    $612,000

    • 4 Beds
    • 2.5 Baths
    • 2,946 Sq Ft
    • 43571 Bayberry Ct
    • Leonardtown, MD

    Gorgeous Colonial on a Beautifully Landscaped 4.26 Acre Premium Lot in the Sought After, Well-Established Neighborhood of Chestnut Ridge. A Welcoming Covered Front Porch leads to an Open Floor Plan with 9 Foot Ceilings and New Luxury Vinyl Plank (LVP) Flooring. Stylish Large Living Room with a Wood Burning Fireplace. Bright Kitchen with 48” Cabinetry, Gleaming Granite, and a Large Pantry. The

    Jenny Norris EXP Realty, LLC

    Section Image
  • 20919 Ridge Path Way, Leonardtown, MD 20650

    $574,900

    • 4 Beds
    • 3.5 Baths
    • 3,465 Sq Ft
    • 20919 Ridge Path Way
    • Leonardtown, MD

    Nestled on a serene and private 3.29-acre lot—plus an additional 0.5-acre parcel—20919 Ridge Path Way offers the perfect balance of seclusion and convenience in the heart of Leonardtown. This professionally upgraded 4-bedroom, 3.5-bath home delivers both peace of mind and high-end comfort with all major systems and appliances less than 5 years old.Step inside and experience a beautifully

    Matthew Burgan Infinitas Realty Group

    Section Image
  • 20591 Chestnut Ridge Dr, Leonardtown, MD 20650

    $615,000

    • 5 Beds
    • 3.5 Baths
    • 3,061 Sq Ft
    • 20591 Chestnut Ridge Dr
    • Leonardtown, MD

    Welcome to this well-built colonial in the picturesque Chestnut Ridge neighborhood!With over 3,000 finished square feet, 5 bedrooms, and 3.5 bathrooms, this home is full of charm, character, and thoughtful craftsmanship.Situated on 2.11 acres, the home features a classic brick exterior, a welcoming front porch, and a spacious two-car garage. Inside on the main level, you'll find two

    Lauren Garner EXP Realty, LLC

    Section Image
  • 21056 Woodmere Dr, Leonardtown, MD 20650

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,205 Sq Ft
    • 21056 Woodmere Dr
    • Leonardtown, MD

    Nice Colonial with Covered Front Porch with concrete, Brick paver sidewalk and step, front load two car garage with exterior door to back yard. Storm Front Door with Side lights, Formal Living Room with Crown Molding, Dining Room Crown and Chair Molding, Hardwood Flooring in Foyer, Hall and Powder Room. Nice Kitchen with Center Island granite countertops, ceramic backsplash, Ceiling Light, New

    Kathryn Mausen Coldwell Banker Jay Lilly Real Estate

    Section Image
  • 19137 Lake Dr, Leonardtown, MD 20650

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,308 Sq Ft
    • 19137 Lake Dr
    • Leonardtown, MD

    If moody modern colors, classy, and close to the water is your vibe, this is the one. Tucked just steps from the shores of the majestic Potomac River, this updated coastal retreat features 3 bedrooms, 2.5 baths, and two fireplaces...one stone fireplace in the cozy living room and another in the owner’s suite. Inside, the home has been freshly painted in a warm, modern palette with deep blues,

    Sarah Mulford-Martin EXP Realty, LLC

    Section Image
  • 21158 Marigold St, Leonardtown, MD 20650

    $500,000

    • 4 Beds
    • 2.5 Baths
    • 2,649 Sq Ft
    • 21158 Marigold St
    • Leonardtown, MD

    Welcome to 21158 Marigold St, a beautifully maintained Colonial in the sought-after Kingston Estates community. This spacious home offers over 2,600 sq ft of living space on more than an acre, blending comfort, functionality, and privacy. It features 4 generously sized bedrooms, 2.5 bathrooms, a finished basement, and an updated kitchen with stainless steel appliances. Step outside to a peaceful,

    Jarred Green Real Broker, LLC

    Section Image

Source: Bright MLS

MLS Number: MDSM2025788

Bright MLS

APN: 02-033577