Maypole Rd, Leonardtown, MD 20650
OFF MARKET

Maypole Rd
Leonardtown, MD 20650

  • Studio

$285,300

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $1,715/mo*
Refinance Your Home

$285,300

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $1,715/mo*
Refinance Your Home
Studio
(on 12.56 acres)

Home Value

Trulia Estimate
$285K
Since last month
Increased$42K (+17.2%)
Since last year
Decreased$7K (-2.3%)
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 decreased by -2% in the last 10 years
MonthEstimated value
2026
August 2026$285K
July 2026$243K
June 2026$303K
May 2026$262K
April 2026$274K
March 2026$285K
February 2026$235K
2025

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
24101 R G Way, Leonardtown, MD
0.04
Single-Family Home
$100,000
11/20/25
3
2,486
24249 McIntosh Rd, Hollywood, MD
0.92
Single-Family Home
$900,000
08/12/26
4
3.5
2,934
41400 Real Quiet Dr, Leonardtown, MD
0.63
Single-Family Home
$799,000
08/14/26
6
4
5,569
41480 Whimsical Ct, Leonardtown, MD
0.68
Single-Family Home
$680,000
10/24/25
5
4
3,825
41438 Silver Charm Ct, Leonardtown, MD
0.75
Single-Family Home
$690,000
03/31/26
5
3.5
4,180
41430 Whimsical Ct, Leonardtown, MD
0.80
Single-Family Home
$645,000
10/15/25
5
3.5
3,907
41395 Omaha Ct, Leonardtown, MD
0.81
Single-Family Home
$720,000
06/26/26
5
3.5
4,367
41402 Silver Charm Ct, Leonardtown, MD
0.81
Single-Family Home
$625,000
12/10/25
5
3.5
4,046
41389 Holiday Ct, Leonardtown, MD
0.84
Single-Family Home
$728,000
05/22/26
5
3.5
4,385
23647 Hansel Ct, Leonardtown, MD
0.86
Single-Family Home
$660,000
09/29/25
5
3.5
3,194

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
23960 R G Way, Leonardtown, MD 20650
0.25
$704,300
4
2.5
2,788
Off Market
41400 Real Quiet Dr, Leonardtown, MD 20650
0.63
$799,000
6
4
5,569
Recently Sold
23760 Coventry Dr, Leonardtown, MD 20650
0.65
$714,900
5
3.5
4,744
For Sale
41411 Real Quiet Dr, Leonardtown, MD 20650
0.67
$734,700
5
3.5
5,296
Off Market
23749 Coventry Dr, Leonardtown, MD 20650
0.67
$768,000
5
3.5
6,015
Off Market
23754 Coventry Dr, Leonardtown, MD 20650
0.67
$729,000
5
3.5
4,794
Off Market
41557 Burnt Mill Dr, Hollywood, MD 20636
0.67
$681,900
3
3
1,922
Off Market
41480 Whimsical Ct, Leonardtown, MD 20650
0.68
$680,000
5
4
3,825
Recently Sold
41432 Silver Charm Ct, Leonardtown, MD 20650
0.75
$752,800
5
4
5,074
Off Market
41438 Silver Charm Ct, Leonardtown, MD 20650
0.75
$690,000
5
3.5
4,180
Recently Sold
41413 Omaha Ct, Leonardtown, MD 20650
0.76
$720,600
5
4
5,164
Off Market
41402 Omaha Ct, Leonardtown, MD 20650
0.76
$749,900
5
4
4,873
For Sale

Local Information

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

Home Highlights

Property Type
Single-Family Home
Lot Size
12.56 acres

About this House

This single-family home is located at Maypole Rd, Leonardtown, MD. Maypole Rd is in Leonardtown, MD and in ZIP code 20650. This property has a lot size of 12.56 acres.
Maypole Rd, Leonardtown, MD 20650 is a studio single-family home. It is currently off market. The Trulia Estimate is $285,300, with a rent estimate of $2,463/month.

Home Details for Maypole Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 12.56 acres

Price and Tax history

DateEventPrice
Dec 17, 2024
Source: Bright MLS #MDSM2011446
ListingRemoved
$125,000
Jul 3, 2023
Source: Bright MLS #MDSM2011446
PriceChange
$125,000
Price decreased by 17%
Jan 24, 2023
Source: Bright MLS #MDSM2011446
Listed For Sale
$150,000

Market trends in Leonardtown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
33
10MoM

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
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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
    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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LGBTQ Local Legal Protections

Frequently asked questions about Maypole Rd

  • What is Maypole Rd estimated to be worth?
    Trulia's estimated value for Maypole Rd in Leonardtown, MD is $285,300.
  • 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.
  • What are the closest schools to Maypole Rd?
    The closest schools to Maypole Rd in Leonardtown, MD are Benjamin Banneker Elementary School (Pre-K, rated 8/10), Chopticon High School (rated 6/10), Leonardtown Middle School (rated 9/10).
  • How big is the lot at Maypole Rd?
    The lot at Maypole Rd in Leonardtown, MD is about 12.6 acres.

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