Location

Nearby schools

School ratings (A+ to F) from HJN community data.

Little Seedlings Christian Preschool & Kindergarden
PK-KG · Early Childhood Program/Child Care Center
7 students · 7.8:1 student–teacher
1.1 mi
Captain Walter Francis Duke Elementary School
PK-5 · Regular · St. Marys County Public Schools
516 students · 14.9:1 student–teacher
Captain Walter Francis Duke Elementary School school rating: A 1.3 mi
Leonardtown Elementary School
PK-5 · Regular · St. Marys County Public Schools
509 students · 16.5:1 student–teacher
Leonardtown Elementary School school rating: B

Nearby places

Within 2 miles of this home: 26 restaurants and cafés, 2 grocery stores, 8 parks and green spaces, and 1 transit stop.

Place data from OpenStreetMap.

Food & drink

McDonald's
Merchants Lane
0.1 mi
KFC
0.2 mi
Subway
Merchants Lane
0.2 mi
Happy Dragon Restaurant
Chinese restaurant
0.2 mi
Pizza Hut
0.2 mi
Crab Knockers
0.2 mi
Arby's
Merchants Lane
0.3 mi

The 20650 market

Homes for sale: 44
Median list price: $549,000

Similar homes nearby

See all in 20650

Price Reduced32Active
$430,000
3 bd · 4 ba · 2,379 sqft
41608 Briarwood Cir, Leonardtown, MD

Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

No listing photos

23295 MAYPOLE ROAD, LEONARDTOWN MD 20650

—

Beds

2

Baths

1,947

Sqft

1968

Year built

Estimated value: $365,023

Range $342,634 – $387,412 · as of August 30, 2026

How this estimate has moved

ATTOM automated valuation model · 53 published estimates over 6.7 years · shaded band is the model's own published low-to-high range

$302,579 January 2020$365,023 August 2026

Highest reading $441,497 in December 2025; lowest $278,712 in May 2025. The vertical scale starts at the series' own low, not at zero — it is drawn to show movement, not absolute size.

Public records

— beds
2 baths
1,947 sqft
108,464 sqft lot
Built 1968
Stories: 1
Use: RESIDENTIAL
APN 03-003159

Estimate your monthly payment

Home price

Down payment (20%)

$73,005

Loan term

Interest rate (%)

Property tax (%/yr)

Home insurance ($/yr)

HOA ($/mo)

Estimated monthly payment

$2,441/mo

Principal & interest$1,990

Property tax$335

Home insurance$117

Loan amount $292,018. Estimate only — your actual rate and payment depend on credit, location, and lender.

Tax history

2026 roll

Land: $121,800
Structure: $239,700
Assessed total: $361,500
County market value: $361,500
Property tax billed: $4,043.62

Sale & deed history

December 15, 2023Arm's-length$280,000

Similar homes nearby

See all in 20650

Price Reduced32Active
$430,000
3 bd · 4 ba · 2,379 sqft
41608 Briarwood Cir, Leonardtown, MD

William Rabbitt · The Southside Group Real Estate

4Active

$290,000

3 bd · 2 ba · 1,568 sqft

43905 Lanedon Dr, Leonardtown, MD

Rose A Taylor · RE/MAX United Real Estate

3Active

$454,900

4 bd · 4 ba · 0 sqft

Lot 143 - 23641 Dragonfly Ln, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

28Active

$450,000

4 bd · 3 ba · 2,604 sqft

20410 Chingville Rd, Leonardtown, MD

William Rabbitt · The Southside Group Real Estate

Price Reduced33Active

$424,900

5 bd · 2 ba · 2,056 sqft

23899 McIntosh Rd, Leonardtown, MD

Jeremy G Browne · EXP Realty, LLC

33Active

$454,900

4 bd · 4 ba · 2,554 sqft

Lot 156 - 23634 Dragonfly Ln, Leonardtown, MD

Laura Lee Hefley · RE/MAX One

Nearby schools

School ratings (A+ to F) from HJN community data.

Nearby places

Within 2 miles of this home: 26 restaurants and cafés, 2 grocery stores, 8 parks and green spaces, and 1 transit stop.

Place data from OpenStreetMap.

Food & drink

McDonald's
Merchants Lane
0.1 mi
KFC
0.2 mi
Subway
Merchants Lane
0.2 mi
Happy Dragon Restaurant
Chinese restaurant
0.2 mi
Pizza Hut
0.2 mi
Crab Knockers
0.2 mi
Arby's
Merchants Lane
0.3 mi

The 20650 market

Homes for sale: 44
Median list price: $549,000

1.3 mi

Father Andrew White Sj School

PK-8 · Regular

213 students · 14.6:1 student–teacher

1.5 mi

Leonard Hall Jr Naval Academy

6-12 · Regular

38 students · 6.0:1 student–teacher

1.5 mi

Benjamin Banneker Elementary School

PK-5 · Regular · St. Marys County Public Schools

543 students · 13.8:1 student–teacher

B 1.8 mi

St Mary S Ryken High School

9-12 · Regular

639 students · 11.2:1 student–teacher

2.4 mi

Loveville Mennonite School

1-8 · Regular

39 students · 19.5:1 student–teacher

3.1 mi

Papa John's

Merchants Lane

0.3 mi

Groceries

Food Lion
0.2 mi
The Good Earth
1.8 mi

Parks & recreation

Leonard's Grant Recreation Area
0.9 mi
Leonard's Grant Common Area
1.1 mi
Leonard's Grant Community Area
1.1 mi
Leonardtown Park
1.3 mi
Miedzinski Playground
1.5 mi
Miedzinski Park
1.5 mi
Hurry Family Parkette
1.7 mi
Former Rowland Property
1.9 mi

Transit

Governmental Center (Transfer Stop)
1.6 mi

Location

Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

Sources for the nearby listings shown on this page

Bright MLS: 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 in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and 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 this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-11-01 18:26:37 UTC