Is parking easy in Leonardtown, MD?

As of early 2026, 91% of users say parking is easy

Are yards well-kept in Leonardtown, MD?

As of early 2026, 91% of users say yards are well-kept

Would people walk alone at night in Leonardtown, MD?

As of early 2026, 86% of users say people would walk alone at night

Do kids play outside in Leonardtown, MD?

As of early 2026, 86% of users say kids play outside

Is a car needed in Leonardtown, MD?

As of early 2026, 86% of users say car is needed

Is Leonardtown, MD dog-friendly?

As of early 2026, 85% of users say it's dog friendly

Does Leonardtown, MD show holiday spirit?

As of early 2026, 76% of users say there's holiday spirit

Is Leonardtown, MD quiet?

As of early 2026, 72% of users say it's quiet

Does Leonardtown, MD have sidewalks?

As of early 2026, 62% of users say there are sidewalks

Are the streets well-lit in Leonardtown, MD?

As of early 2026, 61% of users say streets are well-lit

Do residents of Leonardtown, MD plan to stay at least 5 years?

As of early 2026, 60% of users say they plan to stay for at least 5 years

Is there wildlife in Leonardtown, MD?

As of early 2026, 58% of users say there's wildlife

Are neighbors friendly in Leonardtown, MD?

As of early 2026, 51% of users say neighbors are friendly

Is Leonardtown, MD walkable to restaurants?

As of early 2026, 43% of users say it's walkable to restaurants

Are there community events in Leonardtown, MD?

As of early 2026, 42% of users say there are community events

Is Leonardtown, MD walkable to grocery stores?

As of early 2026, 14% of users say it's walkable to grocery stores

What is 23970 Maypole Rd #E estimated to be worth?

Trulia's estimated value for 23970 Maypole Rd #E in Leonardtown, MD is $154,500 .

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 23970 Maypole Rd #E?

The closest schools to 23970 Maypole Rd #E 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).

Does 23970 Maypole Rd #E have air conditioning?

Yes, 23970 Maypole Rd #E in Leonardtown, MD has air conditioning.

OFF MARKET

$154,500

Trulia Estimate

1 Bed
1 Bath
500 sqft

23970 Maypole Rd #E, Leonardtown, MD 20650

Est. Refi. Payment $973/mo*

Refinance Your Home

Home Value

Trulia Estimate

$155K

Since last month

$2K (-1%)

Since last year

$2K (+1.6%)

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 decreased by -48% in the last 10 years

Month	Estimated value
2026
August 2026	$155K
July 2026	$156K
June 2026	$164K
May 2026	$157K
April 2026	$169K
March 2026	$146K
February 2026	$156K
January 2026	$150K
2025
December 2025	$146K
November 2025	$144K
October 2025	$144K
September 2025	$145K
August 2025	$152K
July 2025	$156K
June 2025	$159K
May 2025	$161K
April 2025	$150K
March 2025	$138K
February 2025	$138K
January 2025	$127K
2024
December 2024	$133K
November 2024	$135K
October 2024	$136K
September 2024	$132K
August 2024	$125K
July 2024	$131K
June 2024	$130K
May 2024	$132K
April 2024	$134K
March 2024	$129K
February 2024	$136K
January 2024	$125K
2023
December 2023	$142K
November 2023	$142K
October 2023	$133K
September 2023	$145K
August 2023	$150K
July 2023	$142K
June 2023	$159K
May 2023	$212K
April 2023	$203K
March 2023	$278K
February 2023	$278K
January 2023	$287K
2022
December 2022	$283K
November 2022	$294K
October 2022	$294K
September 2022	$275K
August 2022	$211K
July 2022	$212K
June 2022	$217K
May 2022	$216K
April 2022	$217K
March 2022	$211K
February 2022	$242K
January 2022	$256K
2021
December 2021	$245K
November 2021	$323K
October 2021	$323K
September 2021	$316K
August 2021	$318K
July 2021	$322K
June 2021	$336K
May 2021	$362K
2020
August 2020	$259K
July 2020	$240K
June 2020	$244K
May 2020	$260K
April 2020	$238K
March 2020	$262K
February 2020	$277K
January 2020	$281K
2019
December 2019	$278K
November 2019	$282K
October 2019	$276K
September 2019	$280K
August 2019	$288K
July 2019	$297K
June 2019	$299K
May 2019	$286K
April 2019	$291K
March 2019	$297K
February 2019	$288K
January 2019	$282K
2018
December 2018	$295K
November 2018	$286K
October 2018	$299K
September 2018	$287K
August 2018	$284K
July 2018	$272K
June 2018	$292K
May 2018	$279K
April 2018	$297K
March 2018	$256K
February 2018	$241K
January 2018	$227K
2017
December 2017	$252K
November 2017	$242K
October 2017	$249K
September 2017	$257K
August 2017	$250K
July 2017	$251K
June 2017	$237K
May 2017	$244K
April 2017	$243K
March 2017	$227K
February 2017	$228K
January 2017	$235K
2016
December 2016	$274K
November 2016	$273K
October 2016	$274K
September 2016	$284K
August 2016	$298K

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
41810 Eastwick Ln #2301, Leonardtown, MD	2.90	Condo	$302,000	05/12/26	2	2	1,101

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	0.08	$702,700	4	2.5	2,788	Off Market
23749 Coventry Dr, Leonardtown, MD 20650	0.73	$772,300	5	3.5	6,015	Off Market
23760 Coventry Dr, Leonardtown, MD 20650	0.74	$714,900	5	3.5	4,744	For Sale
23754 Coventry Dr, Leonardtown, MD 20650	0.75	$726,200	5	3.5	4,794	Off Market
41400 Real Quiet Dr, Leonardtown, MD 20650	0.75	$799,000	6	4	5,569	Recently Sold
41411 Real Quiet Dr, Leonardtown, MD 20650	0.77	$734,700	5	3.5	5,296	Off Market
40744 Fawns Rest Way, Leonardtown, MD 20650	0.82	$731,084	4	3	3,313	Recently Sold
41480 Whimsical Ct, Leonardtown, MD 20650	0.82	$697,200	5	4	3,825	Off Market
41402 Omaha Ct, Leonardtown, MD 20650	0.83	$749,900	5	4	4,873	For Sale
41413 Omaha Ct, Leonardtown, MD 20650	0.83	$720,600	5	4	5,164	Off Market
41432 Silver Charm Ct, Leonardtown, MD 20650	0.86	$748,400	5	4	5,074	Off Market
41438 Silver Charm Ct, Leonardtown, MD 20650	0.87	$690,000	5	3.5	4,180	Recently Sold

Local Information

Map ViewExplore the area around 23970 Maypole Rd #E.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Condo

Year Built

1986

Living Area

500 sqft

Price/Sqft

$309

Parking

None

About this House

This condo is located at 23970 Maypole Rd #E, Leonardtown, MD. 23970 Maypole Rd #E is in Leonardtown, MD and in ZIP code 20650. This property has 1 bedroom, 1 bathroom and approximately 500 sqft of floor space. This property was built in 1986.

23970 Maypole Rd #E, Leonardtown, MD 20650 is a 1 bedroom, 1 bathroom, 500 sqft condo built in 1986. More recently, it was listed as a rental in October 2020 with an asking price of $700 per month. That rental listing was removed on November 11, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $154,500, with a rent estimate of $1,472/month.

Home Details for 23970 Maypole Rd #E

Interior Features
Heating & Cooling Heating: WallAir ConditioningCooling System: WallHeating Fuel: Wall
Appliances & Utilities MicrowaveRefrigerator

Property Information
Year Built Year Built: 1986
Property Type / Style Property Type: CondoArchitecture: Colonial

Exterior Features
Exterior Home Features Exterior: Vinyl
Parking & Garage Parking: None

Price and Tax history

Date	Event	Price
Nov 11, 2020 Source: Agent Provided	ListingRemoved	$700
Oct 30, 2020 Source: Agent Provided	Listed For Rent	$700
Apr 11, 2018 Source: Agent Provided	ListingRemoved	$650
Mar 27, 2018 Source: Agent Provided	Listed For Rent	$650

Additional Cost

Market trends in Leonardtown

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

10MoM

Around this home

Benjamin Banneker Elementary School
PK-5
Public
564 Students
St. Mary's County Public Schools
8/10
GreatSchools Rating
Parent Rating Average
Both of my children have attended Banneker, currently in 2nd and 4th grade. They both love going to school and I can't say enough good things about the teachers! They all have been wonderful! We have been very pleased with our experience at Banneker over the years!
Parent Review
1y ago
3 Reviews

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
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
Resident
2mo ago
"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
Resident
7mo ago
"The dogs are very happy and normally quiet when being walked on the sidewalk in Clark’s Rest Community "
0
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Zddnpc8dsh
Resident
11mo ago
"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
Resident
1y ago
"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
Resident
1y ago
"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
Resident
1y ago
"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
Resident
2y ago
"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
Resident
2y ago
"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
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Keith H.
Resident
5y ago
"Great neighborhood with sidewalks and many families. Good schools and a library just outside the entrance. "
0
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Mybeachjeweler
Resident
6y ago
"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.
Resident
6y ago
"Good consistent drive. Traffic moves on major roads. About 15-20 min delay during morning and evening rush hours. "
1
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Stillask8in
Resident
6y ago
"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.
Resident
6y ago
"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.
Resident
6y ago
"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.
Resident
6y ago
"30 minutes from pax naval base, 40 min to Waldorf, 30-45 min from Calvert County. Some local buses available also."
2
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Unspecified
Resident
7y ago
"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
Resident
7y ago
"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.
Resident
7y ago
"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.
Resident
8y ago
"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
14y ago
"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 23970 Maypole Rd #E

What is 23970 Maypole Rd #E estimated to be worth?
Trulia's estimated value for 23970 Maypole Rd #E in Leonardtown, MD is $154,500.
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 23970 Maypole Rd #E?
The closest schools to 23970 Maypole Rd #E 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).
Does 23970 Maypole Rd #E have air conditioning?
Yes, 23970 Maypole Rd #E in Leonardtown, MD has air conditioning.