39115 Windward Ln, Leonardtown, MD 20650
OFF MARKET

39115 Windward Ln
Leonardtown, MD 20650

  • 2 Baths
2 Baths
(on 6.91 acres)

Local Information

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Description

39115 Windward Ln is in Leonardtown, MD and in ZIP code 20650. This property has 2 bathrooms. This property has a lot size of 6.91 acres and was built in 2001.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 39115 Windward Ln

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: Unknown

Lot Information

Lot Area: 6.91 acres

Price History for 39115 Windward Ln

DatePriceEventSource
06/12/2019$180,000Sold
N/A
10/15/2014$250,000Sold
N/A

Market trends in Leonardtown

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
41
10MoM
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Property Tax and Assessment

Year2025
Tax$1,281
Assessment$119,700
Home facts updated by county records

Homeowner tools

Estimated monthly rent$1,896/mo
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Comparable Sales for 39115 Windward Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
40534 Miss Ettas Way, Leonardtown, MD
0.36
Single-Family Home
$480,000
11/24/25
3
2.5
1,770
40744 Fawns Rest Way, Leonardtown, MD
0.34
Single-Family Home
$731,084
12/04/25
4
3
3,313
23674 J M Gough Ct, Leonardtown, MD
0.36
Single-Family Home
$537,500
09/30/25
4
2.5
2,697
21925 Budds Creek Rd, Leonardtown, MD
0.66
Single-Family Home
$465,000
02/11/26
3
2
2,527
23650 Rocky Ridge Ct, Leonardtown, MD
0.50
Single-Family Home
$599,000
09/18/25
4
3.5
3,914
23730 Hicks Dr, Leonardtown, MD
0.90
Single-Family Home
$402,000
01/06/26
3
2
1,992
23593 Mitchell Dr, Leonardtown, MD
0.57
Single-Family Home
$580,000
03/23/26
5
3.5
2,940
23745 Hicks Dr, Leonardtown, MD
0.96
Single-Family Home
$406,000
07/25/25
3
2
984
24101 R G Way, Leonardtown, MD
1.12
Single-Family Home
$100,000
11/20/25
3
2,486
40626 Rudys Ln, Leonardtown, MD
1.16
Single-Family Home
$300,000
05/27/26
3
2
1,330

Nearby homes

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Assigned Schools

These are the assigned schools for 39115 Windward Ln.
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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.
  • 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
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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!"
    0
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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 "
    0
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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 "
    0
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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. "
    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
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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. "
    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
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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. "
    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
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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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Off Market Homes Near 39115 Windward Ln

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39115 Windward Ln, Leonardtown, MD 20650 is a 2 bathroom unknown built in 2001. This property is not currently available for sale. 39115 Windward Ln was last sold on Jun 12, 2019 for $180,000.