Features & Amenities

Interior

  • Other Interior Features

    Ceiling Fan(s), Kitchen Island, Soaking Tub, Walk-In Closet(s)

  • Total Bedrooms

    5

  • Bathrooms

    3

  • 1/2 Bathrooms

    1

  • Above Grade Finished Area

    2475.0

  • Basement YN

    NO

  • Cooling YN

    YES

  • Cooling

    Central Air, Ceiling Fan(s)

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Exhaust Fan, Electric

  • Main Level Bedrooms

    1

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Vinyl Siding

  • Parking

    Asphalt, Private, Attached

  • Pool

    No

  • Waterfront YN

    NO

  • View

    Trees/Woods

Area & Lot

  • Lot Features

    Cleared, Front Yard, Level, Private

  • Lot Size(acres)

    2.26

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Colonial

Price

  • Sales Price

    $559,000

  • Tax Amount

    3606.0

  • Sq. Footage

    2, 475

  • Price/SqFt

    $225

HOA

  • Association

    NO

School District

  • Elementary School

    LEONARDTOWN

  • Middle School

    LEONARDTOWN

  • High School

    LEONARDTOWN

Property Features

  • Senior Community YN

    NO

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

SAINT MARYS

Elementary School

LEONARDTOWN

Middle School

LEONARDTOWN

High School

LEONARDTOWN

Listing Courtesy of Bill Oosterink , CENTURY 21 New Millennium

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent MarylandSandbox

FOUNDER

MarylandSandbox

Call Maryland today to schedule a private showing.


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
PRICE IMPROVEMENT!  Introducing a stunning FIVE-bedroom, three and a half-bath colonial home located in the highly sought-after Leonardtown school district. Nestled on a sprawling 2.26-acre lot, this residence offers an unparalleled level of comfort and serenity. Boasting a recently replaced roof in April 2023, the HVAC units updated in June 2022, and a brand-new water heater and water softener installed in January 2023, this home is not only beautifully designed but also meticulously maintained.

What sets this property apart is its exceptional attention to detail and recent renovations, making it truly "turn-key" for its fortunate new owners. The entire home showcases fresh paint and new flooring, creating a modern and inviting atmosphere. The kitchen has been elegantly upgraded with new countertops, updated cabinets, and stainless steel appliances, providing a stylish and functional space for culinary endeavors.

Enjoy the convenience of a main floor master bedroom, two cozy gas fireplaces, and a spacious family room upstairs, ideal for quality family time or entertaining guests. Step outside to discover a picturesque setting, complete with a concrete pad and gazebo installed in March 2023, perfect for outdoor gatherings and relaxation.

One of the unique features of this property is its location in an area with no homeowners association (HOA), offering you the freedom and flexibility to make this home truly your own. With all these exceptional features and the attractive Leonardtown school district, this home is sure to captivate discerning buyers.

Don't miss out on the opportunity to make this beautiful property your own – act quickly, as homes of this caliber in Leonardtown rarely stay on the market for long. Your dream home awaits!

22030 CARTWRIGHT ROAD

Message successfully sent.

What would you like to know?

Related Properties

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 crabbing, fishing, kayaking, or canoeing, this location is an outdoor enthusiast’s paradise. Enjoy the sights and sounds of ospreys, fish, and abundant wildlife right from your doorstep. Key features include:
✔ Approximate water depth: 2.5 ft at low tide, 4.5 ft at high tide
✔ Seawall refurbished in 2020 for added shoreline protection
✔ Private pier with an electric boat lift—perfect for boating adventures
Don’t miss this rare chance to own a piece of paradise with endless potential. Whether you’re looking for an investment, vacation retreat, or future dream home, this waterfront gem is a must-see!
#MDSM2022922

LEONARDTOWN

20798 WATERSIDE DRIVE

2 Beds

1 Baths

1,018 Sq.Ft.

$450,000

MLS#: MDSM2022922

Warm, charming with style on CHELSEY FAYE. The Chelsey Model Home  is a modestly sized one story design that is loaded with all the necessities. Beautiful white siding and stained timber accents are perfect material choices for the farmhouse style. Offering an open main level  with one large space for living and dining. The family room has a high ceiling.  Enjoy the cozy ambiance of this home with a warming fireplace. The owner's suite is private & separate from the other bedrooms. Perfect for relaxation & tranquility.  The owner's bath features a large shower and ample closet space. Bedroom three is a flexible space that doubles as a work space. The optional upper level adds another sleeping space and a large bonus room. The bonus room can be utilized as simple storage or finished for a recreation or exercise room; the choice is yours! Graham & Co Custom Builder.

Board and Batten is optional. 
Custom Build- floor plan can be modified.
New Construction Home to Be Built. 
Custom Builder. 
Second story is optional
#MDSM2016780

LEONARDTOWN

41815 CHELSEY FAYE

3 Beds

2 Baths

1,627 Sq.Ft.

$530,000

MLS#: MDSM2016780

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 reimagined interior where thoughtful updates have brought fresh life to the kitchen and bathrooms. Whether you're preparing meals in the upgraded kitchen or relaxing in one of the spacious living areas, you'll appreciate the quality finishes, abundant natural light, and seamless flow throughout.

The expansive lot provides ample space for outdoor enjoyment, gardening, recreation, or even future additions. With a combined total of 3.79 acres of usable land, you’ll have room to roam, entertain, or simply relax in nature’s embrace.

Located just minutes from NAS Patuxent River, as well as Leonardtown's best shopping, dining, waterfront parks, and entertainment, this home is ideally situated for those seeking privacy without sacrificing convenience.

Key Features:

4 spacious bedrooms and 3.5 modernized bathrooms

Professionally updated kitchen and baths

All major systems and appliances less than 5 years old

3.29-acre primary lot plus additional 0.5-acre parcel

Private, usable land ideal for recreation or relaxation

Prime location near NAS Pax River, shopping, restaurants, and parks

Whether you're commuting to work, entertaining friends, or enjoying quiet evenings under the stars, 20919 Ridge Path Way is the home that truly has it all.
#MDSM2025994

LEONARDTOWN

20919 RIDGE PATH WAY

4 Beds

3 Baths

3,465 Sq.Ft.

$574,900

MLS#: MDSM2025994

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, the expansive primary suite includes a full en suite bathroom, accompanied by three additional generously sized bedrooms and another full bath.

Full basement to finish as you would like. New paint and carpet thru out.  Roof replaced in 2018, geothermal replaced in 2012 and windows replaced in 2022,

A long driveway leads to a 2-car garage, and the property includes two storage sheds—perfect for hobbies or extra space.

Don't miss the opportunity to own this serene retreat in one of the area's most desirable neighborhoods!
#MDSM2024842

LEONARDTOWN

20814 DEER WOOD PARK DRIVE

4 Beds

2 Baths

3,576 Sq.Ft.

$589,000

MLS#: MDSM2024842

Escape the stresses of everyday life and enjoy your breezy coastal retreat with the luxuries of Leonard's Grant community that has it all from a spacious pool, basketball court, tennis court, playground, or feel free to frolic in the wide open green field.   Designed to bring that beachy tranquility to your everyday life with a coastal design reminiscent of cool breezes and sandy beaches.  Freshly painted with Sherwin Williams exuding coastal ambiance with creamy accents.  Gorgeous new carpet throughout.  The premium deep ocean blue fiber cement  exterior greets you as you walk into your oasis. Fenced backyard complete with two large garden beds and endless possibilities.  Enjoy your massive deck with so many options whether grilling, gazing at the stars, or enjoying the evening breeze with family and friends overlooking the twinkling yard lights. As an added bonus, put your feet up while your automatic sprinklers do the work for you.  Walk to your elementary school and library.  Don’t miss out on paradise!  Check out this hidden gem you won’t be disappointed!
#MDSM2026396

LEONARDTOWN

41402 SILVER CHARM COURT

5 Beds

3 Baths

4,782 Sq.Ft.

$635,000

MLS#: MDSM2026396

Welcome to 22626 Chickadee Lane—an exceptional 4-bedroom, 3.5-bath home nestled on a serene 2-acre lot in the highly sought-after Avenmar neighborhood of Leonardtown. This elegant property offers the perfect blend of privacy, space, and convenience with an open-concept layout that is flooded with natural light and designed for comfortable living and entertaining.

Inside, you'll find generously sized rooms, a flowing floor plan, and thoughtful finishes throughout. The main living spaces are bright and airy, creating a warm and inviting atmosphere ideal for gatherings or quiet evenings at home.

Outside, enjoy your large and private TWO ACRE lot. The hardscaping and wooded back yard are perfect for  relaxing or entertaining while the large flat side and front yard are perfect for ALL the outside activities. 

Enjoy a lifestyle of ease and recreation with Avenmar’s impressive amenities, including a community pool, tennis courts, equestrian center, clubhouse, and more. Golf enthusiasts will love being within such close proximity to Breton Bay Golf Club. Plus, you're just a short drive from NAS Patuxent River, waterfront areas, parks, dining, shopping, and all that Southern Maryland has to offer.

Don't miss this rare opportunity to own a beautiful home in one of Leonardtown’s premier communities. Schedule your private tour today!
#MDSM2025998

LEONARDTOWN

22626 CHICKADEE LANE

4 Beds

3 Baths

4,682 Sq.Ft.

$649,000

MLS#: MDSM2025998

Welcome home to this beautifully updated Colonial located in a charming and quiet Leonardtown neighborhood—just minutes from local restaurants, shopping, and all the conveniences of town living.
Freshly painted throughout and featuring brand-new carpet, this 4-bedroom, 2.5-bath gem is move-in ready and full of modern upgrades. The heart of the home is a gourmet kitchen with upgraded stainless steel appliances, granite countertops, and ample cabinet space—perfect for both everyday living and entertaining.
Upstairs, you’ll find a HUGE primary suite complete with a  en-suite bath and 2  closets, along with three additional spacious bedrooms and bathroom.
The basement is unfinished but already roughed in!  Finish, or not, to your liking!
Step outside to enjoy a large, beautiful deck overlooking a fully fenced backyard.
Added Bonus...Home has Hardwire Ethernet lines in every room of the house!! 
Don’t miss your chance to own this well-maintained home in a sought-after location in Leonardtown. 
Schedule your private showing today!
#MDSM2024680

LEONARDTOWN

23674 JM GOUGH COURT

4 Beds

2 Baths

3,857 Sq.Ft.

$537,500

MLS#: MDSM2024680

Price Improvement!!!!  This home is a MUST SEE!!!!

Spacious 5-Bedroom Colonial with Coveted First-Floor Suite & Finished Basement 

Welcome to this beautifully maintained 5-bedroom 3.5-bath Colonial home, ideally situated in one of the area's most sought-after communities. With classic curb appeal, generous living space, and thoughtful updates throughout, this home is perfect for growing families, multi-generational living, or anyone seeking flexible, functional space.

Step inside to find a warm, welcoming layout , a spacious eat-in kitchen, and a cozy family room ideal for relaxing or entertaining. One of the standout features is the highly desirable first-floor large primary suite with an en-suite bath and ample closet space.

Upstairs, you’ll find three large additional bedrooms with ample closet space and a full bath.

The fully finished basement is a true bonus, offering even more living space with a fifth bedroom, full bathroom, and a custom theatre room—perfect for movie nights, game days, or casual entertaining.

Additional highlights include:

3.5 well-appointed bathrooms

First-floor laundry

Two-car garage with additional driveway parking

Spacious backyard with room to relax, play, or entertain

Located in a friendly, established neighborhood with top-rated schools, parks, and easy access to shopping, dining, and Pax River Naval Base

Captain Walter Francis Duke Elementary School

This home checks all the boxes—space, location, and versatile living options. Don’t miss your opportunity to make it yours!
#MDSM2026418

LEONARDTOWN

41430 WHIMSICAL COURT

5 Beds

3 Baths

4,963 Sq.Ft.

$619,999

MLS#: MDSM2026418

Welcome to the Academy Hills of Leonardtown.  The main level features a traditional floor plan, recent upgrades including new carpet August 2025, stainless steel kitchen appliances, plenty of cabinet space, a formal dining room, and a convenient powder room. Major system updates include a brand-new Roof and a new HVAC system for added peace of mind.
Upstairs, newly installed banisters, the high-ceiling primary suite offers a relaxing retreat with dual walk-in closets and a luxurious en-suite bath featuring a corner soaking tub, separate shower, and double vanity. Three additional bedrooms share a beautiful full bath with a tub located in the hallway. 
The fully fenced backyard boasts an expansive deck with fresh stain and railings 2025—ideal for entertaining or relaxing outdoors. Additional improvements include attic insulation, fresh paint, and refreshed landscaping.
With a two-car garage, spacious layout, and proximity to Leonardtown’s waterfront, restaurants, shops, and community events, this home offers the perfect balance of comfort, style, and convenience.
#MDSM2025890

LEONARDTOWN

41900 NAZARETH COURT

4 Beds

2 Baths

3,622 Sq.Ft.

$475,000

MLS#: MDSM2025890

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 comfortable living areas, a dedicated dining space, and a kitchen with granite countertops, stainless steel appliances, and plenty of room to make it your own. Step right out onto the back deck to enjoy the peaceful outdoor setting.

All five bedrooms are located on the second and third floors, offering privacy and space for everyone. The rooms are generously sized, including a spacious primary suite and a versatile bonus room above the garage—perfect for a home office, playroom, or guest retreat.
The unfinished basement adds even more flexibility, offering excellent storage or future expansion potential. New Roof in 2018.

Enjoy the quiet setting, timeless design, and endless potential this Chestnut Ridge gem offers—ready for its next chapter.

Don’t miss your chance to own a home with this much space, land, and value—schedule your private showing today!
#MDSM2025274

LEONARDTOWN

20591 CHESTNUT RIDGE DRIVE

5 Beds

3 Baths

3,337 Sq.Ft.

$615,000

MLS#: MDSM2025274

 - property

Send a message

Message successfully sent.

Your message

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to receive some additional information on this specific property or similar properties?

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here