39862 Big Pine Trl, Leonardtown, MD 20650
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Property image
OFF MARKET

39862 Big Pine Trl
Leonardtown, MD 20650

  • 4 Beds
  • 2.5 Baths
  • 1,656 sqft

$412,300

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $2,165/mo*
Refinance Your Home

$412,300

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $2,165/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,656 sqft

Local Information

  • Map ViewExplore the area around 39862 Big Pine Trl.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2002
Living Area
1,656 sqft
Price/Sqft
$249
Parking
Open Parking

Description

ADORABLE CAPE COD on CORNER LOT in Historic Leonardtown, MD! This 4 Bed, 2.5 Bath home features a 1-Car Detached Shed/Workshop/Garage, Paved Driveway, Architectural Shingles, Fenced-in Back Yard, Deck, Main Floor Primary Bedroom w/ walk-in closet along with Primary Bathroom, Laundry on Upper Level, Beautiful Updated Kitchen w/ Pantry, SS Appliances, Dining Area, Combination Dining & Livingroom, Tub/Shower Combinations, and Built-ins, NO HOA! This home is located in the St. Clements Shores Water Oriented Community and offers access to the community beach, pier and pavilion as well as access to the community boat ramp with an optional and minimal annual community recreation paid fee. Enjoy the convenience of being close to the Water, Golf Course/Country Club, Nightlife, Grocery Stores, Shopping, Boutique Shops, Gas Stations, Banks, Hospital, Restaurants, Post Office, Downtown Leonardtown, Leonardtown Wharf, College, Parks, Winery, and SO MUCH MORE! Come fall in love with The Woods at Bayside and live your HAPPILY EVER AFTER!
39862 Big Pine Trl, Leonardtown, MD 20650 is a 4 bedroom, 3 bathroom, 1,656 sqft single-family home built in 2002. It last sold for $385,000 on May 31, 2024 (3% above the $375,000 asking price). It is currently off market. The Trulia Estimate is $412,300, with a rent estimate of $2,642/month.

Home Details for 39862 Big Pine Trl

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 3
Dimensions and Layout
Living Area: 1656 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Underground UtilitiesAppliances: Microwave, Dryer, Exhaust Fan, Oven/Range - Electric, Refrigerator, Stainless Steel Appliance(s), Washer, Water Heater, Electric Water HeaterDryerLaundry: Has Laundry,Upper LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Ceiling Fan(s),Heat Pump,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
No Fireplace
Gas & Electric
Electric: Underground
Windows, Doors, Floors & Walls
Window: Insulated Windows, Double Pane Windows, Vinyl Clad, Double Hung, Window TreatmentsDoor: Storm Door(s), Insulated, Six PanelFlooring: Carpet, Vinyl, Luxury Vinyl
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Carpet, Vinyl, Luxury Vinyl
View
No View
Security
Security: Smoke Detector(s), Main Entrance Lock, Carbon Monoxide Detector(s)

Exterior Features

Exterior Home Features
Roof: Architectural Shingle PitchedPatio / Porch: Deck, PatioFencing: Vinyl, PrivacyOther Structures: Above Grade, Below Grade, OutbuildingExterior: Lighting, Rain GuttersFoundation: Crawl SpaceNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Private,Asphalt,Driveway
Pool
Pool: None
Frontage
Waterfront: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Swimming Allowed, BayNot on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: St. Clements Bay
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1656 Square Feet

Property Information

Year Built
Year Built: 2002
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Cape Cod
Building
Construction Materials: Batts Insulation, Frame, Stick Built, Vinyl SidingNot a New ConstructionNo Additional Parcels
Property Information
Condition: GoodIncluded in Sale: Wishing Well, Treadmill, L-shaped Desk, Blackstone Grill, Patio Furniture W / Cushions, Shed / Garage W / Cabinets. Items Can Be Removed From Property If Buyer Does Not Want Them To Be Included.Parcel Number: 1903057070

Price & Status

Price
List Price: $375,000
Status Change & Dates
Off Market Date: Mon Jun 03 2024Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: LEONARDTOWNCommunity: The Woods At Bayside
School Information
Elementary School: Benjamin BannekerElementary School District: St. Mary's County Public SchoolsJr High / Middle School: LeonardtownJr High / Middle School District: St. Mary's County Public SchoolsHigh School: ChopticonHigh School District: St. Mary's County Public Schools

Building

Building Area
Building Area: 1656 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 9025 sqft

Listing Info

Special Conditions: Standard

Offer

Contingencies: Appraisal, Financing Approval, Home InspectionListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, USDA Loan, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDSM2018342Above Grade Unfinished Area: 1656
Last check for updates: about 2 hours ago
Listed by Danny Bell, (301) 904-7034
NOVA Brokers, LLC.
Bought with: Billy Rabbitt, (240) 249-7870, Home Towne Real Estate
Source: Bright MLS, MLS#MDSM2018342

Price History for 39862 Big Pine Trl

DatePriceEventSource
05/31/2024$385,000Sold
Bright MLS #MDSM2018342
04/23/2024$375,000PendingBright MLS #MDSM2018342
04/21/2024$375,000Listed For SaleBright MLS #MDSM2018342
05/03/2022$310,000Sold
N/A
11/14/2013$239,900Sold
N/A
09/20/2013$239,900PendingAgent Provided
09/07/2013$239,900Listed For SaleAgent Provided
03/02/2005$259,500Sold
N/A
08/20/2002$149,900Sold
N/A

Market trends in Leonardtown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$540K
$19.15KMoM
Sale-to-List Price
100.0%
Price per sq ft
$199
$3MoM
Available listings
23
10MoM
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Property Tax and Assessment

Year2025
Tax$3,277
Assessment$294,400
Home facts updated by county records

Comparable Sales for 39862 Big Pine Trl

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
39944 Lady Baltimore Ave, Leonardtown, MD
0.16
Single-Family Home
$400,000
06/15/26
5
2.5
2,169
22381 Cedar St, Leonardtown, MD
0.38
Single-Family Home
$335,000
07/07/26
3
2
1,287
22204 Nomoni St, Leonardtown, MD
0.45
Single-Family Home
$315,000
04/10/26
2
2
1,008
22175 Bayside Rd, Leonardtown, MD
0.32
Single-Family Home
$315,000
05/28/26
2
2
1,192
39577 Potomac Ave, Leonardtown, MD
0.55
Single-Family Home
$824,900
06/29/26
4
2.5
3,412
21920 Newtowne Neck Rd, Leonardtown, MD
0.66
Single-Family Home
$520,000
01/30/26
4
2.5
2,291

Nearby homes

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Assigned Schools

These are the assigned schools for 39862 Big Pine Trl.
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

  • 75 % Say there's holiday spirit

  • 72 % Say it's quiet

  • 62 % Say there are sidewalks

  • 61 % Say streets are well-lit

  • 61 % 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 "
    0
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  • Mybeachjeweler
    "The dogs are very happy and normally quiet when being walked on the sidewalk in Clark’s Rest Community "
    0
    Flag
  • Zddnpc8dsh
    "The downtown is a vibrant place, with piped in music and lots of community activities, like First Friday events every month."
    0
    Flag
  • 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. "
    0
    Flag
  • 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!"
    0
    Flag
  • Mybeachjeweler
    "Dog owners would like this neighborhood as many neighbors have dogs and walk them on leases daily. Dogs are friendly "
    0
    Flag
  • Mybeachjeweler
    "I see people walking their dogs day and night. All dogs are on a lease and are most friendly to chi "
    0
    Flag
  • 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. "
    0
    Flag
  • Keith H.
    "Great neighborhood with sidewalks and many families. Good schools and a library just outside the entrance. "
    0
    Flag
  • Mybeachjeweler
    "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.
    "Good consistent drive. Traffic moves on major roads. About 15-20 min delay during morning and evening rush hours. "
    1
    Flag
  • Stillask8in
    "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.
    "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.
    "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
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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
    Flag
  • Unspecified
    "Easy, multiple routes to the Naval Air Station. From Leonardtown it is easy to get to all restaurants, shopping and entertainment."
    0
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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!"
    4
    Flag
  • 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. "
    0
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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. "
    0
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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."
    0
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8 rentals with air conditioning in Leonardtown, MD

Homes for sale near 39862 Big Pine Trl

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Off Market Homes Near 39862 Big Pine Trl

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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