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

$408,100

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 1,656 sqft

39862 Big Pine Trl, Leonardtown, MD 20650

Est. Refi. Payment $2,526/mo*
Refinance Your Home
Currently Off Market - Sold May 31, 2024 for $385,000

Home Value

Trulia Estimate
$408K
Since last month
Decreased$3K (-0.7%)
Since last year
Decreased$500 (-0.1%)
Since last sale
Increased$23K (+6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +70% in the last 10 years
MonthEstimated value
2026
September 2026$408K
August 2026$411K
July 2026$412K
June 2026$414K
May 2026$417K
April 2026$415K
March 2026$411K
February 2026$408K
January 2026$409K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
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
22281 Nomoni St, Leonardtown, MD
0.38
Single-Family Home
$340,000
07/31/26
3
2
1,152
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
22332 Cedar St, Leonardtown, MD
0.38
Single-Family Home
$325,000
08/14/26
2
1
1,000
39577 Potomac Ave, Leonardtown, MD
0.55
Single-Family Home
$824,900
06/29/26
4
2.5
3,412

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
39880 Lady Baltimore Ave, Leonardtown, MD 20650
0.06
$429,000
3
2
1,348
Off Market
39834 Big Pine Trl, Leonardtown, MD 20650
0.07
$364,100
3
2
1,344
Off Market
39843 Lady Baltimore Ave, Leonardtown, MD 20650
0.12
$377,100
4
2
1,224
Off Market
39790 Lady Baltimore Ave, Leonardtown, MD 20650
0.14
$350,700
4
2
1,344
Off Market
39944 Lady Baltimore Ave, Leonardtown, MD 20650
0.16
$400,000
5
2.5
2,169
Recently Sold
Zacks Way, Leonardtown, MD 20650
0.18
-
-
-
-
Off Market
39902 Long Leaf Ln, Leonardtown, MD 20650
0.22
-
3
2.5
2,472
Off Market
22301 Bayside Rd, Leonardtown, MD 20650
0.26
$575,400
4
2.5
2,368
Off Market
39922 Long Leaf Ln, Leonardtown, MD 20650
0.28
-
-
-
-
Off Market
39725 Lady Baltimore Ave, Leonardtown, MD 20650
0.27
$310,000
3
2
1,886
Recently Sold
22425 Archer St, Leonardtown, MD 20650
0.29
$805,700
3
2
1,876
Off Market

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

Single-Family Home
Built in 2002
1,656 sqft
$246/sqft
Open Parking

About this House

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). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $408,100, with a rent estimate of $2,729/month.
Last check for updates: about 22 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

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

Price and Tax history

DateEventPrice
May 31, 2024
Source: Bright MLS #MDSM2018342
Sold
$385,000
Apr 23, 2024
Source: Bright MLS #MDSM2018342
Pending
$375,000
Apr 21, 2024
Source: Bright MLS #MDSM2018342
Listed For Sale
$375,000
May 3, 2022
Source: N/A
Sold
$310,000
Nov 14, 2013
Source: N/A
Sold
$239,900

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
7MoM

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 "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag

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Frequently asked questions about 39862 Big Pine Trl

  • What is 39862 Big Pine Trl estimated to be worth?
    Trulia's estimated value for 39862 Big Pine Trl in Leonardtown, MD is $408,100.
  • What is the price history for 39862 Big Pine Trl?
    39862 Big Pine Trl in Leonardtown, MD last sold for $385,000 in May 2024.
  • Is Leonardtown a buyer's or seller's market?
    Leonardtown is currently a seller's market, based on recent for-sale activity.
  • 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 recently sold homes in Leonardtown, MD.
  • Does 39862 Big Pine Trl have air conditioning?
    Yes, 39862 Big Pine Trl in Leonardtown, MD has air conditioning.
  • Does 39862 Big Pine Trl have laundry facilities?
    Yes, 39862 Big Pine Trl in Leonardtown, MD has in-unit laundry.

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