Whirlwind Rd, Leonardtown, MD 20650
Property image
Property image
FOR SALE
23.44 ACRES

$288,900

    Whirlwind Rd, Leonardtown, MD 20650

    Est. Mortgage $1,793/mo*
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    Home Highlights

    Lot/Land
    23.44 acre lot

    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!
    Last check for updates: about 7 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.

    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: 87

    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

    Around this home

    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
      "Don’t have one i’m a biz owner here. Many small businesses in town. Great for boaters and water enthusiasts "
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    • Mybeachjeweler
      "The dogs are very happy and normally quiet when being walked on the sidewalk in Clark’s Rest Community "
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    • Zddnpc8dsh
      "The downtown is a vibrant place, with piped in music and lots of community activities, like First Friday events every month."
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    • Mybeachjeweler
      "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. "
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    • Vmagostinelli
      "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!"
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    • Mybeachjeweler
      "Dog owners would like this neighborhood as many neighbors have dogs and walk them on leases daily. Dogs are friendly "
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    • Mybeachjeweler
      "I see people walking their dogs day and night. All dogs are on a lease and are most friendly to chi "
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    • Vmagostinelli
      "It’s an amazing small town with entertainment and great restaurants within walking distance. Located on Breton Bay with great boating and fishing options. "
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    • Keith H.
      "Great neighborhood with sidewalks and many families. Good schools and a library just outside the entrance. "
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    • Mybeachjeweler
      "I see many walking their dogs on a daily path around the neighborhood everybody has their dog on a leash and we wave"
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    • Keith H.
      "Good consistent drive. Traffic moves on major roads. About 15-20 min delay during morning and evening rush hours. "
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    • Stillask8in
      "This is a very small town. Most people commute 45 mins to the military base for work. Longest commute of my life. "
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    • Roy M.
      "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. "
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    • Roy M.
      "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 "
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    • Jennie C.
      "30 minutes from pax naval base, 40 min to Waldorf, 30-45 min from Calvert County. Some local buses available also."
      2
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    • Unspecified
      "Easy, multiple routes to the Naval Air Station. From Leonardtown it is easy to get to all restaurants, shopping and entertainment."
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    • Unspecified
      "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!"
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    • Destiny A. M.
      "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. "
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    • Destiny A. M.
      "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. "
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    • dtscls
      "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."
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    Market trends in Leonardtown

    Last updated August 2026
    Buyer'sMarketSeller'sMarket
    Avg. sale price
    —
    Sale-to-List Price
    —
    Price per sq ft
    —
    Available listings
    40
    7    MoM

    Home Value

    Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

    Comparable sales

    These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
    Address
    Distance
    Property Type
    Sold Price
    Sold Date
    Bed
    Bath
    Sqft
    19921 Tower Hill Rd, Leonardtown, MD
    1.81
    Lot/Land
    $100,000
    05/08/26
    -
    -
    Saint Andrews Church Rd, Leonardtown, MD
    2.86
    Lot/Land
    $70,000
    09/04/26
    -
    -
    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
    -
    -
    45567 & 45571 Norris Rd, Great Mills, MD
    5.15
    Lot/Land
    $1,484,200
    10/03/25
    -
    -
    24645 Springhill Ln, Leonardtown, MD
    5.46
    Lot/Land
    $175,000
    09/09/26
    -
    -
    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
    -
    -
    Flat Iron Rd, Valley Lee, MD
    6.12
    Lot/Land
    $200,000
    05/06/26
    -
    -

    Nearby home prices

    Get a sense of expected prices in the area by checking the value of nearby homes.
    Address
    Distance
    Price
    Bed
    Bath
    Sqft
    Status
    20959 Redgate Ln, Leonardtown, MD 20650
    0.13
    $150,000
    3
    1
    1,026
    Recently Sold
    22717 Point Lookout Rd, Leonardtown, MD 20650
    0.19
    $334,800
    3
    2
    1,243
    Off Market
    43164 Gum Spring Dr, Leonardtown, MD 20650
    0.29
    $777,900
    4
    2.5
    3,000
    Off Market
    43107 Gum Spring Dr, Leonardtown, MD 20650
    0.48
    $625,000
    3
    2.5
    2,742
    Recently Sold
    43225 Prince Pine Ct, Leonardtown, MD 20650
    0.54
    $664,900
    4
    3.5
    2,960
    Off Market
    22509 Point Lookout Rd, Leonardtown, MD 20650
    0.57
    $330,800
    3
    1
    1,296
    Off Market
    20753 Chestnut Ridge Dr, Leonardtown, MD 20650
    0.59
    $560,000
    4
    2.5
    2,594
    Recently Sold
    Point Lookout Rd, Leonardtown, MD 20650
    0.61
    -
    -
    -
    -
    Off Market
    20760 Chestnut Ridge Dr, Leonardtown, MD 20650
    0.67
    $622,800
    6
    3.5
    3,492
    Off Market
    20740 Chestnut Ridge Dr, Leonardtown, MD 20650
    0.68
    $640,200
    4
    3
    3,572
    Off Market
    42975 Baywood Pl, Leonardtown, MD 20650
    0.71
    $690,000
    4
    2.5
    3,372
    Recently Sold

    Price and Tax history

    DateEventPrice
    Jun 25, 2026
    Source: Bright MLS #MDSM2032048
    		Listed For Sale
    $288,900
    Jun 15, 2026
    Source: Bright MLS #MDSM2031426
    		ListingRemoved
    $435,000
    May 25, 2026
    Source: Bright MLS #MDSM2031426
    		Listed For Sale
    $435,000

    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

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    Frequently asked questions about Whirlwind Rd

    • How big is Whirlwind Rd?
      Whirlwind Rd in Leonardtown, MD is about 23.4 acres.
    • What is the price per acre for Whirlwind Rd?
      Whirlwind Rd in Leonardtown, MD is listed at $288,900, or about $10K per acre.
    • What do residents say about Leonardtown?
      Residents describe Leonardtown, MD as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See homes for sale in Leonardtown, MD.
    • What are the closest schools to Whirlwind Rd?
      The closest schools to Whirlwind Rd in Leonardtown, MD are Leonardtown High School (rated 8/10), Leonardtown Middle School (rated 9/10), Piney Point Elementary School (Pre-K, rated 7/10).
    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.