21738 Pinehurst Ct, Leonardtown, MD 20650
Property image
Property image
SOLD
FEB 27, 2026

21738 Pinehurst Ct
Leonardtown, MD 20650

  • 4 Beds
  • 2.5 Baths
  • 1,952 sqft (on 0.37 acres)

$487,000

Last Sold: Feb 27, 2026
2% below list $495K
$249/sqft
Est. Refi. Payment $2,845/mo*
Refinance Your Home

$487,000

Last Sold: Feb 27, 2026
2% below list $495K
$249/sqft
Est. Refi. Payment $2,845/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,952 sqft
(on 0.37 acres)

Local Information

  • Map ViewExplore the area around 21738 Pinehurst Ct.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

A rare opportunity for golf course living! Welcome home to this beautifully appointed colonial, perfectly situated on the 6th hole of the Breton Bay Golf Course. Featuring granite countertops, some new appliances, fresh paint, and more, this home is move-in ready. The upper level offers three spacious bedrooms, with a fourth bedroom located in the finished basement—ideal for guests or a home office. Enjoy breathtaking views of the 5th and 6th holes from the screened-in porch, expansive deck, and private hot tub. Just steps from the neighborhood beach, public golf course and clubhouse, and a private marina with rental slips available, this home delivers the best of the Breton Bay lifestyle. Seller is offering a flooring credit for the first floor with Clarke's Flooring.
21738 Pinehurst Ct, Leonardtown, MD 20650 is a 4 bedroom, 3 bathroom, 1,952 sqft single-family home built in 1992. It last sold for $487,000 on Feb 27, 2026 (2% below the $495,000 asking price). It is currently off market. The Trulia Estimate is $493,400, with a rent estimate of $2,801/month.

Home Highlights

Parking
2 Car Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
$5/Monthly
Price/Sqft
$249/sqft
Listed
180+ days ago

Home Details for 21738 Pinehurst Ct

Interior Features

Interior Details
Basement: OtherNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1952 Square Feet
Appliances & Utilities
Appliances: Electric Water HeaterLaundry: In Basement,Washer In Unit,Dryer In Unit
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Other,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Spa: Hot TubHas a FireplaceNo Spa
Levels, Entrance, & Accessibility
Stories: 1.5Levels: One and One HalfAccessibility: None
View
Has a ViewView: Golf Course

Exterior Features

Exterior Home Features
Roof: CompositionOther Structures: Above Grade, Below GradeFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Faces Front,Attached
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Septic
Farm & Range
Not Allowed to Raise Horses
Finished Area
Finished Area (above surface): 1952 Square Feet

Property Information

Year Built
Year Built: 1992
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New ConstructionNo Additional Parcels
Property Information
Condition: Very GoodParcel Number: 1903044904

Price & Status

Price
List Price: $495,000Price Per Sqft: $249/sqft
Status Change & Dates
Off Market Date: Fri Feb 27 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: LEONARDTOWNCommunity: Breton Bay Pud
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

Building

Building Area
Building Area: 3090 Square Feet

Community

Not Senior Community

HOA

Has an HOAHOA Fee: $15/Quarterly

Lot Information

Lot Area: 0.37 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDSM2028668Above Grade Unfinished Area: 1952
Last check for updates: about 3 hours ago
Listed by Steve Carroll, (301) 904-6126
Berkshire Hathaway HomeServices PenFed Realty
Bought with: Alice Flerlage, (240) 299-9359, Real Broker, LLC
Source: Bright MLS, MLS#MDSM2028668

Price History for 21738 Pinehurst Ct

DatePriceEventSource
02/27/2026$487,000Sold
Bright MLS #MDSM2028668
01/07/2026$495,000PendingBright MLS #MDSM2028668
01/02/2026$495,000Listed For SaleBright MLS #MDSM2028668
07/29/2024$2,800Sold
BHHS PenFed solds #ecbb28f651905a4bfffb6b6ba6349032
07/18/2023$509,000ListingRemovedBright MLS #MDSM2011922
05/06/2023$509,000PriceChange
Bright MLS #MDSM2011922
03/08/2023$519,000Listed For SaleBright MLS #MDSM2011922
05/16/2022$519,900ListingRemovedBright MLS #MDSM2004718
03/15/2022$519,900Listed For SaleBright MLS #MDSM2004718
03/06/2022$509,000ListingRemovedBright MLS #MDSM2004718
03/06/2022$519,900PriceChange
Bright MLS #MDSM2004718
02/03/2022$509,000Listed For SaleBright MLS #MDSM2004718
05/05/1995$179,000Sold
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$4,188
Assessment$379,000
Home facts updated by county records

Comparable Sales for 21738 Pinehurst Ct

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
21745 Pinehurst Ct, Leonardtown, MD
0.04
Single-Family Home
$610,000
11/21/25
4
2.5
2,860
21749 Pinehurst Ct, Leonardtown, MD
0.07
Single-Family Home
$595,000
04/14/26
4
3.5
3,410
21807 Potomac View Dr, Leonardtown, MD
0.67
Single-Family Home
$485,000
07/02/26
4
3
2,019
40810 Meadow Dr, Leonardtown, MD
0.55
Single-Family Home
$459,900
06/17/26
3
2
1,368
40855 Spring House Ln, Leonardtown, MD
0.59
Single-Family Home
$540,000
06/04/26
5
3
3,464
21767 Potomac View Dr, Leonardtown, MD
0.69
Single-Family Home
$565,000
06/01/26
4
3.5
4,384
22224 Monterey Pl, Leonardtown, MD
1.08
Single-Family Home
$440,000
04/24/26
4
3
2,176
22186 Monterey Pl, Leonardtown, MD
1.00
Single-Family Home
$510,000
09/19/25
4
2
2,935

Nearby homes

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Assigned Schools

These are the assigned schools for 21738 Pinehurst Ct.
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
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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. "
    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
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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 "
    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
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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. "
    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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Homes for sale near 21738 Pinehurst Ct

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Off Market Homes Near 21738 Pinehurst Ct

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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