21745 Pinehurst Ct, Leonardtown, MD 20650
Property image
Property image
SOLD
NOV 21, 2025

$626,900

Trulia Estimate
  • 4 Beds
  • 2.5 Baths
  • 2,860 sqft (on 0.58 acres)

21745 Pinehurst Ct, Leonardtown, MD 20650

Est. Refi. Payment $3,803/mo*
Refinance Your Home
Currently Off Market - Sold Nov 21, 2025 for $610,000 (1% above list price)

Home Value

Trulia Estimate
$627K
Since last month
$200 (0%)
Since last year
Increased$20K (+3.3%)
Since last sale
Increased$19K (+3.1%)
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 +62% in the last 10 years
MonthEstimated value
2026
September 2026$629K
August 2026$629K
July 2026$621K
June 2026$626K
May 2026$622K
April 2026$621K
March 2026$621K
February 2026$616K
January 2026$617K
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
21749 Pinehurst Ct, Leonardtown, MD
0.03
Single-Family Home
$595,000
04/14/26
4
3.5
3,410
21737 Pinehurst Ct, Leonardtown, MD
0.02
Single-Family Home
$540,000
07/16/26
3
2
3,014
21738 Pinehurst Ct, Leonardtown, MD
0.04
Single-Family Home
$487,000
02/27/26
4
2.5
1,952
21822 Riviera Ct, Leonardtown, MD
0.32
Single-Family Home
$615,000
07/13/26
5
3.5
3,384
40582 Port Pl, Leonardtown, MD
0.41
Single-Family Home
$461,000
08/20/26
3
2
2,196
40855 Spring House Ln, Leonardtown, MD
0.62
Single-Family Home
$540,000
06/04/26
5
3
3,464
21807 Potomac View Dr, Leonardtown, MD
0.69
Single-Family Home
$485,000
07/02/26
4
3
2,019
21767 Potomac View Dr, Leonardtown, MD
0.72
Single-Family Home
$565,000
06/01/26
4
3.5
4,384
40810 Meadow Dr, Leonardtown, MD
0.58
Single-Family Home
$459,900
06/17/26
3
2
1,368

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
21733 Pinehurst Ct, Leonardtown, MD 20650
0.04
$587,000
4
3.5
3,602
Off Market
21737 Pinehurst Ct, Leonardtown, MD 20650
0.02
$540,000
3
2
3,014
Recently Sold
21738 Pinehurst Ct, Leonardtown, MD 20650
0.04
$487,000
4
2.5
1,952
Recently Sold
21749 Pinehurst Ct, Leonardtown, MD 20650
0.03
$595,000
4
3.5
3,410
Recently Sold
40459 Breton View Dr, Leonardtown, MD 20650
0.10
$394,200
3
3.5
2,286
Off Market
40457 Breton View Dr, Leonardtown, MD 20650
0.11
$426,500
3
3.5
2,286
Off Market
40407 Breton View Dr, Leonardtown, MD 20650
0.09
$393,800
3
3
2,640
Off Market
40427 Breton View Dr, Leonardtown, MD 20650
0.11
$414,700
3
4.5
2,676
Off Market
40449 Breton View Dr, Leonardtown, MD 20650
0.13
$424,600
3
3.5
2,288
Off Market
40443 Breton View Dr, Leonardtown, MD 20650
0.14
$398,300
3
3.5
2,604
Off Market
21821 Rosebank Ct, Leonardtown, MD 20650
0.16
$936,900
5
4
4,200
Off Market

Local Information

  • Map ViewExplore the area around 21745 Pinehurst Ct.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1991
0.58 acre lot
2,860 sqft
$213/sqft
2 Car Garage
HOA $25/mo

About this House

OPEN HOUSE CANCELED DUE TO ACCEPTED CONTRACT. Desirable Breton Bay Brick Colonial with a NEW ROOF! Enter the soaring two-story foyer of this 4-bedroom, 2.5 bath home, and take note of the refinished hardwood floors, wide staircase with wrought iron railings, and Palladian window that allows for lots of natural light. Head past the shiplap wall treatment into the eat-in kitchen that features tall white cabinets, newer appliances, beautiful Quartz counters, tile backsplash, updated flooring, and pantry closet. For elegant gatherings, a formal living room w/ crown molding, and dining room w/ bump out, make the perfect setting. The family room with a floor-to-ceiling stone hearth, and French doors out the paver patio are great for more informal entertaining. A home office space, powder room, and convenient mud room/laundry complete the main floor. Outside, a gorgeous hardscape patio and fire ring lead out to the flat, open backyard with trees and woods beyond. Upstairs, attractive, and easy care LVP flooring is found throughout. A spacious primary suite features upscale bath updates like the tiled shower with double heads and body jets, and a big walk-in closet with custom organizing system. Generous secondary bedrooms all have ceiling fans, double closets and one features another walk-in w/organizer. Updates in the hall bath, too! The side-load two-car garage, a built-in generator transfer switch, UV filtration, composite steps, and an "invisible fence" are other perks of owning this amazing home. The unfinished basement is great for storage, workout and games as-is, but is also a blank canvas for whatever you can dream up! Just a minute away you can head down down the hill to picnic, kayak and fish at the community beach & dock for a nominal annual fee, or head up the hill and look into joining the Breton Bay Country Club. It offers a public 18 hole golf course, a restaurant with stunning river and sunset views, and private pool/tennis memberships. Minutes from shopping, restaurants, main commuter routes, and charming & historic Leonardtown, this home is a "don't miss it" opportunity, request your showing today!
21745 Pinehurst Ct, Leonardtown, MD 20650 is a 4 bedroom, 3 bathroom, 2,860 sqft single-family home built in 1991. It last sold for $610,000 on Nov 21, 2025 (1% above the $605,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $626,900, with a rent estimate of $3,148/month.
Last check for updates: about 1 hour ago
Listed by Patrick Deighan, (410) 739-5277
CENTURY 21 New Millennium
Listing Team: The Stachelczyk Shemeta Deighan Team, Co-Listing Team: The Stachelczyk Shemeta Deighan Team,Co-Listing Agent: Andrew Shemeta, (717) 855-5659
CENTURY 21 New Millennium
Bought with: Chris Norris JR., (240) 925-9431, Topside Realty
Source: Bright MLS, MLS#MDSM2027072

Home Details for 21745 Pinehurst Ct

Interior Features

Interior Details
Basement: Sump Pump,UnfinishedNumber of Rooms: 11Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Primary Bathroom, Bathroom 2, Dining Room, Family Room, Kitchen, Living Room, Office
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: 2860 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Disposal, Exhaust Fan, Microwave, Water Heater, Refrigerator, Oven/Range - Electric, Electric Water HeaterDishwasherDisposalLaundry: Main LevelMicrowaveRefrigerator
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Ceiling Fan(s),Heat Pump,Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Stone, Mantel(s)Has a Fireplace
Windows, Doors, Floors & Walls
Window: Window TreatmentsFlooring: Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Wood
View
Has a ViewView: Trees/Woods

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: PatioFencing: InvisibleOther Structures: Above Grade, Below GradeExterior: Sidewalks, Extensive HardscapeFoundation: Block, SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Faces Side,Garage Door Opener,Inside Entrance,Oversized,Private,Attached,Driveway,Off Street,On Street
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 2860 Square Feet

Property Information

Year Built
Year Built: 1991
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Combination, Brick, Brick Front, Vinyl SidingNot a New Construction
Property Information
Parcel Number: 1903044971

Price & Status

Price
List Price: $605,000Price Per Sqft: $213/sqft
Status Change & Dates
Off Market Date: Fri Nov 21 2025Possession Timing: Delay Settlement, Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: LEONARDTOWNCommunity: Breton Bay Pud
School Information
Elementary School District: St. Marys County Public SchoolsJr High / Middle School: LeonardtownJr High / Middle School District: St. Marys County Public SchoolsHigh School: LeonardtownHigh School District: St. Marys County Public Schools

Building

Building Area
Building Area: 4140 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Common Area Maintenance, Snow RemovalHOA Name: BRETON BAY LANDINGSHas an HOAHOA Fee: $300/Annually

Lot Information

Lot Area: 0.58 acres

Listing Info

Special Conditions: Standard

Offer

Contingencies: Home Inspection, Appraisal, Financing ApprovalListing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDSM2027072Above Grade Unfinished Area: 2860

Additional Information

HOA Amenities: Beach Access,Pier/Dock,Picnic Area,Tot Lots/Playground,Pool Mem Avail

Price and Tax history

DateEventPrice
Nov 21, 2025
Source: Bright MLS #MDSM2027072
Sold
$610,000
Sep 20, 2025
Source: Bright MLS #MDSM2027072
Contingent
$605,000
Sep 16, 2025
Source: Bright MLS #MDSM2027072
Listed For Sale
$605,000
Apr 1, 2022
Source: Bright MLS #MDSM2004996
Sold
$580,000
Mar 12, 2022
Source: Bright MLS #MDSM2004996
Pending
$580,000

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
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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
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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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Frequently asked questions about 21745 Pinehurst Ct

  • What is 21745 Pinehurst Ct estimated to be worth?
    Trulia's estimated value for 21745 Pinehurst Ct in Leonardtown, MD is $626,900.
  • What is the price history for 21745 Pinehurst Ct?
    21745 Pinehurst Ct in Leonardtown, MD last sold for $610,000 in November 2025.
  • 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 21745 Pinehurst Ct have air conditioning?
    Yes, 21745 Pinehurst Ct in Leonardtown, MD has air conditioning.
  • Does 21745 Pinehurst Ct have a pool?
    Yes, 21745 Pinehurst Ct in Leonardtown, MD has a pool.

Explore by feature - Pet Friendly

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Off Market Homes Near 21745 Pinehurst Ct

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