Is parking easy in Leonardtown, MD?

As of early 2026, 91% of users say parking is easy

Are yards well-kept in Leonardtown, MD?

As of early 2026, 91% of users say yards are well-kept

Would people walk alone at night in Leonardtown, MD?

As of early 2026, 86% of users say people would walk alone at night

Do kids play outside in Leonardtown, MD?

As of early 2026, 86% of users say kids play outside

Is a car needed in Leonardtown, MD?

As of early 2026, 86% of users say car is needed

Is Leonardtown, MD dog-friendly?

As of early 2026, 85% of users say it's dog friendly

Does Leonardtown, MD show holiday spirit?

As of early 2026, 76% of users say there's holiday spirit

Is Leonardtown, MD quiet?

As of early 2026, 72% of users say it's quiet

Does Leonardtown, MD have sidewalks?

As of early 2026, 62% of users say there are sidewalks

Are the streets well-lit in Leonardtown, MD?

As of early 2026, 61% of users say streets are well-lit

Do residents of Leonardtown, MD plan to stay at least 5 years?

As of early 2026, 60% of users say they plan to stay for at least 5 years

Is there wildlife in Leonardtown, MD?

As of early 2026, 58% of users say there's wildlife

Are neighbors friendly in Leonardtown, MD?

As of early 2026, 51% of users say neighbors are friendly

Is Leonardtown, MD walkable to restaurants?

As of early 2026, 43% of users say it's walkable to restaurants

Are there community events in Leonardtown, MD?

As of early 2026, 42% of users say there are community events

Is Leonardtown, MD walkable to grocery stores?

As of early 2026, 14% of users say it's walkable to grocery stores

FOR SALE

23.44 ACRES

Whirlwind Rd
Leonardtown, MD 20650

$288,900

Est. Mortgage $1,755/mo*

Get Pre-Qualified

$288,900

Est. Mortgage $1,755/mo*

Get Pre-Qualified

(on 23.44 acres)

Home Highlights

Listed

41 days ago

Local Information

Map ViewExplore the area around Whirlwind Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

About this House

Finding the perfect lot offering a tranquil, secluded setting yet within an easy drive of historic Leonardtown, NAS Pax River, schools, and amenities can be a real whirlwind of an experience! No worries, as this is the ideal opportunity to achieve just that. This 23-acre parcel of raw land offers many possibilities, whether establishing an enduring farmette, subdividing to reap the rewards, or creating the family compound you've all been dreaming of. This beautiful land is conveniently positioned just off Rt. 5, in a prime location between St. Mary's State Park and the charming St. Mary's County seat, Leonardtown. Note that the location is not actually ON Whirlwind Rd; it is best accessed at the end of Redgate Ln. Future potential to create access from both Rt. 5 and Redgate Ln. Call for more details!

Home Details for Whirlwind Rd

Interior Features
View No View

Exterior Features
Frontage Not on Waterfront
Water & Sewer Sewer: No Septic System

Days on Market
Days on Market: 41

Property Information
Property Type / Style Property Type: LandProperty Subtype: Unimproved Land
Building No Additional Parcels
Property Information Parcel Number: 1903017443

Price & Status
Price List Price: $288,900
Status Change & Dates Possession Timing: Close Of Escrow

Active Status
MLS Status: ACTIVE

Location
Direction & Address City: LEONARDTOWN
School Information Elementary School District: St. Mary's County Public SchoolsJr High / Middle School District: St. Mary's County Public SchoolsHigh School District: St. Mary's County Public Schools

Agent Information
Listing Agent Listing ID: MDSM2032048

HOA
No HOA

Lot Information
Lot Area: 23.44 Acres

Listing Info
Special Conditions: Standard

Offer
Listing Agreement Type: Exclusive Right To Sell

Business
Business Information Ownership: Fee Simple

Miscellaneous
Mls Number: MDSM2032048Municipality: Unincorporated

Additional Information
Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Last check for updates: about 3 hours ago

Listing courtesy of Brooke Matthews, (301) 904-5180

RE/MAX One, (443) 771-8009

Listing Team: Brooke Matthews Group

Source: Bright MLS, MLS#MDSM2032048

Also Listed on Bright MLS.

Market trends in Leonardtown

Last updated June 2026

Avg. sale price

$540K

$19.15KMoM

Sale-to-List Price

100.0%

Price per sq ft

$199

$3MoM

Available listings

10MoM

Price History for Whirlwind Rd

Date	Price	Event	Source
06/25/2026	$288,900	Listed For Sale	Bright MLS #MDSM2032048

06/15/2026	$435,000	ListingRemoved	Bright MLS #MDSM2031426

05/25/2026	$435,000	Listed For Sale	Bright MLS #MDSM2031426

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Comparable Sales for Whirlwind Rd

Address	Distance	Property Type	Sold Price	Sold Date	Bath	Sqft
19921 Tower Hill Rd, Leonardtown, MD	1.81	Lot/Land	$100,000	05/08/26	-	-
22020 Victorian Dr, California, MD	3.03	Lot/Land	$75,000	03/13/26	-	-
Na Millers Mill Road & Salem Cemetary Rd, Callaway, MD	3.58	Lot/Land	$145,000	01/01/26	-	-
40624 Breton Knolls Ct, Leonardtown, MD	4.57	Lot/Land	$1,240,037	09/05/25	-	-
45567 & 45571 Norris Rd, Great Mills, MD	5.15	Lot/Land	$1,484,200	10/03/25	-	-
41650 Miss Bessie Dr, Leonardtown, MD	4.90	Lot/Land	$120,000	08/06/25	-	-
Kiskadee Ln, Leonardtown, MD	5.49	Lot/Land	$175,000	02/02/26	-	-
40533 Breton Knolls Ct, Leonardtown, MD	5.48	Lot/Land	$185,000	04/08/26	-	-
Hollywood Rd, Hollywood, MD	5.73	Lot/Land	$11,500	04/20/26	-	-

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for Whirlwind Rd.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Leonardtown

At least 38 Trulia users voted on each feature.

91 % Say parking is easy
91 % Say yards are well-kept
86 % Say people would walk alone at night
86 % Say kids play outside
86 % Say car is needed
85 % Say it's dog friendly
76 % Say there's holiday spirit
72 % Say it's quiet
62 % Say there are sidewalks
61 % Say streets are well-lit
60 % Say they plan to stay for at least 5 years
58 % Say there's wildlife
51 % Say neighbors are friendly
43 % Say it's walkable to restaurants
42 % Say there are community events
14 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Carrieibly
Resident
1mo ago
"Don’t have one i’m a biz owner here. Many small businesses in town. Great for boaters and water enthusiasts "
0
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Mybeachjeweler
Resident
6mo ago
"The dogs are very happy and normally quiet when being walked on the sidewalk in Clark’s Rest Community "
0
Flag
Zddnpc8dsh
Resident
10mo ago
"The downtown is a vibrant place, with piped in music and lots of community activities, like First Friday events every month."
0
Flag
Mybeachjeweler
Resident
1y ago
"You can walk your dogs on a lease in ease and children love to wave and pet the dogs if the owner allows. This is a great community for dogs as long as they are not barking all the time. "
0
Flag
Vmagostinelli
Resident
1y ago
"I love first Fridays! I love the town vibe! The wharf is amazing. Most people can’t walk to everything. I feel I’m fortunate!"
0
Flag
Mybeachjeweler
Resident
1y ago
"Dog owners would like this neighborhood as many neighbors have dogs and walk them on leases daily. Dogs are friendly "
0
Flag
Mybeachjeweler
Resident
2y ago
"I see people walking their dogs day and night. All dogs are on a lease and are most friendly to chi "
0
Flag
Vmagostinelli
Resident
2y ago
"It’s an amazing small town with entertainment and great restaurants within walking distance. Located on Breton Bay with great boating and fishing options. "
0
Flag
Keith H.
Resident
5y ago
"Great neighborhood with sidewalks and many families. Good schools and a library just outside the entrance. "
0
Flag
Mybeachjeweler
Resident
6y ago
"I see many walking their dogs on a daily path around the neighborhood everybody has their dog on a leash and we wave"
0
Flag
Keith H.
Resident
6y ago
"Good consistent drive. Traffic moves on major roads. About 15-20 min delay during morning and evening rush hours. "
1
Flag
Stillask8in
Resident
6y ago
"This is a very small town. Most people commute 45 mins to the military base for work. Longest commute of my life. "
0
Flag
Roy M.
Resident
6y ago
"Great schools in the Leonardtown area and lots of history as well. Many different food choices from Seafood Mexican AMERICAN Chinese and the olde town cafe. "
0
Flag
Roy M.
Resident
6y ago
"Local town events and close to water access. Great food lots of shopping and small businesses Everyone is polite and friendly Great schools and local parks Volunteer rescue squad and fire departments and local hospital Local beach communities Golfing "
0
Flag
Jennie C.
Resident
6y ago
"30 minutes from pax naval base, 40 min to Waldorf, 30-45 min from Calvert County. Some local buses available also."
2
Flag
Unspecified
Resident
7y ago
"Easy, multiple routes to the Naval Air Station. From Leonardtown it is easy to get to all restaurants, shopping and entertainment."
0
Flag
Unspecified
Resident
7y ago
"Perfect, close to the base and beautiful downtown Leonardtown. On the golf course with a few hundred yard walk to clubhouse (which has fantastic food and drinks), but most importantly, only a short walk to the Breton Bay Beach and playground which the children (and adults) love!"
4
Flag
Destiny A. M.
Resident
7y ago
"I have two dogs myself and walk them all the time. I like they have side walks for my dogs to walk on but I don’t like that there isn’t a dog park anywhere around here. I feel they should add dog parks around here to make it better for dogs to get the excerise they need and want. "
0
Flag
Destiny A. M.
Resident
7y ago
"Love leonardtown and love the area that I’m in. I love that everything is right here in the square and have so many nice people around me. Everyone in this area knows me and says hi even if they don’t know who you are. "
0
Flag
dtscls
14y ago
"The townhomes at Breton Bay Landing are all excellently maintained by HOA standards; including the grounds and road maintenance. The community is family friendly and welcoming. The waterfront is beautiful and the nature friendly environment includes eagles, swans, geese and numerous beautiful birds."
0
Flag

LGBTQ Local Legal Protections

Brooke Matthews, RE/MAX One, (443) 771-8009

Agent Phone: (301) 904-5180

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. 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. Copyright 2026 Bright MLS, Inc. Click here for more information

Whirlwind Rd, Leonardtown, MD 20650 is a lot/land. This property is currently available for sale and was listed by Bright MLS on Jun 25, 2026. The MLS # for this home is MLS# MDSM2032048.

Whirlwind Rd Leonardtown, MD 20650

$288,900

$288,900

Home Highlights

Local Information

About this House

Home Details for Whirlwind Rd

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Agent Information

HOA

Lot Information

Listing Info

Offer

Business

Miscellaneous

Additional Information

Market trends in Leonardtown

Price History for Whirlwind Rd

Similar Homes You May Like

New Listings near Whirlwind Rd

Comparable Sales for Whirlwind Rd

Nearby homes

Additional Cost

Assigned Schools

What Locals Say about Leonardtown

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

Whirlwind Rd
Leonardtown, MD 20650