OFF MARKET

Off Market Apr 2024 for $327K

$397,917

Est. refi paymentEst. refi $2,591/mo

•

1,584

sq ft

23255 Hollywood Rd, Leonardtown, MD 20650

About this home

Back to Active. Buyer home sale contingency fell through. Cape Cod Cutie in Leonardtown! This charming home has tons of character. Located just minutes from downtown Leonardtown. The screened porch is perfect for relaxing and enjoying a cup of coffee in the morning or cocktails in the evening. This home includes 3 Bedrooms and 1 1/2 bathrooms. Country kitchen w/ updated cabinets, flooring and appliances. Plenty of space for a breakfast table and chairs. Freshly painted and updated HVAC system. Large circular driveway and plenty of parking. Detached garage and carport allow for storage and other equipment. Close to area restaurants, amenities, hospital, library, wharf, schools and much more. Schedule your showing appointment today.

Single-familyProperty Type

1930Year Built

0.7 acresLot Size

$251Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Kelly Padgett • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Listed by Mike Tennity • CENTURY 21 New Millennium

•301-862-2169 (broker)

•tommy.higgins@c21nm.com (broker)

Bought with Boyd Grainger • Exit Landmark Realty

•301-934-2022 (broker)

•exitlandmarkmd@gmail.com (broker)

Redfin checked: a minute ago

•Source:BRIGHT MLS #MDSM2016352

Redfin Estimate

$397,917

$71K since sold in April 2024$3,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 10.1% lower than the average sale price ($442K) of 6 comparable homes.

SOLD JUN 26, 2026
$434,000
A
3 beds2 baths1,910 sq ft
41600 Miss Bessie Dr, Leonardtown, MD 20650
SOLD JUN 2, 2026
$530,000
B
3 beds2.5 baths1,926 sq ft
23207 Moakley St, Leonardtown, MD 20650
SOLD SEP 16, 2025
$330,000
C
3 beds1 bath1,402 sq ft
23280 Hollywood Rd, Leonardtown, MD 20650
SOLD JUN 17, 2026
$459,900
D
3 beds2 baths1,368 sq ft
40810 Meadow Dr, Leonardtown, MD 20650
SOLD JUN 1, 2026
$440,000
E
3 beds2.5 baths1,314 sq ft
24415 Morgan Rd, Hollywood, MD 20636
SOLD AUG 20, 2026
$461,000
F
3 beds2 baths2,196 sq ft
40582 Port Pl, Leonardtown, MD 20650

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Earn from this home

Sell

$122,992

Est. take-home

List your home with Redfin and save $3,979

Refinance

Est. cash available

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Rent

$1,696/mo

Redfin rental estimate

List your home for rent

Market trends in 20650, MD

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.7%

+0.6% MoM

Median sale price

$535K

$30K MoM

Avg. days on market

49d

5 days MoM

Recently sold homes

13 MoM

New listings for sale

$450,000
4 beds3 baths2,604 sq ft
20410 Chingville Rd, Leonardtown, MD 20650
(301) 298-2892
$649,900
4 beds2.5 baths3,314 sq ft
22157 Monterey Pl, Leonardtown, MD 20650
(301) 862-2169
$319,000
3 beds1 bath2,068 sq ft
43146 N Megan Ln, Leonardtown, MD 20650
(410) 394-0990
COMING SOON
$424,900
4 beds3.5 baths2,306 sq ft
41517 Margrove Cir, Leonardtown, MD 20650
(240) 925-2224
$639,900
4 beds3.5 baths3,340 sq ft
23444 Lindsay Dr, Leonardtown, MD 20650
(443) 771-8009
REDFIN OPEN SEP 26, 2PM TO 4PM
$609,900
4 beds3.5 baths2,736 sq ft
23354 Lindsay Dr, Leonardtown, MD 20650
See all

Provided by Redfin

Sale history for 23255 Hollywood Rd

Date

Event

Price

BRIGHT MLS #MDSM2016352

Apr 17, 2024

Sold

$327,000

$206/sq ft

Feb 25, 2024

Contingent

—

Feb 19, 2024

Relisted

—

Feb 14, 2024

Listing Removed

—

Feb 8, 2024

Relisted

—

Feb 2, 2024

Contingent

—

Jan 27, 2024

Price Changed

$314,900

$199/sq ft

Jan 20, 2024

Price Changed

$324,900

$205/sq ft

Jan 5, 2024

Price Changed

$329,900

$208/sq ft

Dec 18, 2023

Relisted

—

Dec 12, 2023

Pending

—

Dec 6, 2023

Listed

$335,000

$211/sq ft

RENT. #1

Nov 7, 2022

Rental Removed

—

BRIGHT MLS #MDSM2006378

Oct 1, 2022

Listing Removed

—

Sep 6, 2022

Relisted

—

Jul 26, 2022

Listing Removed

—

Jul 1, 2022

Relisted

—

Jun 30, 2022

Listing Removed

—

Jun 17, 2022

Price Changed

$305,000

$193/sq ft

May 29, 2022

Price Changed

$325,000

$205/sq ft

May 18, 2022

Price Changed

$338,000

$213/sq ft

May 4, 2022

Listed

$345,000

$218/sq ft

Public Records

Oct 26, 2020

Sold

$245,000

$155/sq ft

BRIGHT MLS #MDSM165482

May 27, 2020

Sold

$245,000

$155/sq ft

Apr 6, 2020

Pending

—

Dec 4, 2019

Price Changed

$250,000

$158/sq ft

Oct 16, 2019

Listed

$265,000

$167/sq ft

Want to live in Leonardtown? Well here's your chance! Public and private schools, MedStar St. Mary s Hospital, St. Mary s Nursing Home, College of Southern Maryland, County Sheriff and State Police, Local Library, Governmental Center, and shopping within a 4 mile radius. Recent utility upgrades include; new oil tank, water heater and lines, furnace and newly sealed driveway, New flight fixtures. The Generac Generator conveys.

Year

Property tax

Land + Additions

Assessment*

2025

$3,023 (+8.5%)

2024

$2,786 (+10.0%)

$110,400 + $134,800

$245,200

2023

$2,532 (+7.1%)

2022

$2,364 (+13.9%)

2021

$2,074 (+1.9%)

$110,400 + $87,700

$198,100

2020

$2,036 (+1.9%)

2019

$1,997

2018

$1,995 (+1.0%)

$105,400 + $81,900

$187,300

2017

$1,976 (−2.3%)

$105,400 + $81,900

$187,300

2015

$2,022 (+16.4%)

$120,400 + $78,300

$198,700

2014

$1,737 (+4.1%)

$120,400 + $92,700

$213,100

2013

$1,669 (+5.1%)

2012

$1,588 (+5.5%)

2011

$1,506

2010

$1,506 (+3.2%)

2009

$1,459

Tax history for 23255 Hollywood Rd

Year

Property tax

Land + Additions

Assessment*

2025

$3,023 (+8.5%)

2024

$2,786 (+10.0%)

$110,400 + $134,800

$245,200

2023

$2,532 (+7.1%)

2022

$2,364 (+13.9%)

2021

$2,074 (+1.9%)

$110,400 + $87,700

$198,100

2020

$2,036 (+1.9%)

2019

$1,997

2018

$1,995 (+1.0%)

$105,400 + $81,900

$187,300

2017

$1,976 (−2.3%)

$105,400 + $81,900

$187,300

2015

$2,022 (+16.4%)

$120,400 + $78,300

$198,700

2014

$1,737 (+4.1%)

$120,400 + $92,700

$213,100

2013

$1,669 (+5.1%)

2012

$1,588 (+5.5%)

2011

$1,506

2010

$1,506 (+3.2%)

2009

$1,459

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

—

Baths

1.5

Stories

1.5

Lot width

—

Lot depth

—

Lot size

0.7 Acres

Year renovated

—

Sq. Ft.

1,584

Year built

1930

Style

Single Family Residential

County

St. Mary's County

APN

03 009394

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 21, 2026.

Property details

Parking

Parking Information
# of Detached Garage Spaces: 1
Garage Features: Additional Storage Area, Garage - Front Entry
# of Total Garage and Parking Spaces: 5
Has Garage
# of Garage Spaces: 1
Driveway - # of Spaces: 4
Driveway, Detached Garage

Interior

Bedroom Information
# of Bedrooms On 1st Upper Level: 2
# of Bedrooms On Main Level: 1

Bathroom Information
# of Bathrooms (Full) On 1st Upper Level: 1
# of Bathrooms (Half) On Main Level: 1
# of Bathrooms (Full) On All Upper Levels: 1
# of Bathrooms (Half): 1
# of Bathrooms (Full): 1

Interior Information
Appliances: Dishwasher, Dryer, Exhaust Fan, Microwave, Refrigerator, Stove, Washer
Living Area Sq.Ft. Source: Assessor

Basement Information
Basement: No

Exterior

Property Information
Total Below Grade Sq. Ft.: 0
Improvement Assessed Value: $87,700
Ownership Interest: Fee Simple
Year Built Source: Assessor

Building Information
Construction Materials: Frame
Foundation Details: Crawl Space
Other Structures: Above Grade, Below Grade
Structure Type: Detached

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $110,400

Above Grade Information
Finished Sq.Ft.: 1,584
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
City/Town Tax: $257
County Tax: $2,052
Tax Assessed Value: $213,800
Tax Year: 2023
Tax Annual Amount: $2,309

Assessments Information
Year Assessed: 2023

Utilities

Utilities Information
Central Air
Cooling Type: Ceiling Fan(s), Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Public

Location

School Information
School District Name: ST. MARY'S COUNTY PUBLIC SCHOOLS
School District Source: Listing Agent

Location Information
In City Limits
Directions: Route 245 Holly/Leonardtown Road. Directly across from Old Library. See sign.
Municipality: Leonardtown

Public facts

Beds: —
Baths: 1.5
Sq. Ft.: 1,584
Stories: 1.5
Lot Size: 0.7 acres
Style: Single Family Residential
Year Built: 1930
Year Renovated: —
County: St. Mary's County
APN: 03 009394

Home facts updated by county records on Aug 21, 2026

Other

Listing Information
Automatically Close on Close Date

Around this home

Schools

Captain Walter Francis Duke Elementary

Public PreK-5 • Assigned • 0.6mi

9/10

Leonardtown Middle School

Public 6-8 • Assigned • 2.5mi

9/10

Leonardtown High School

Public 9-12 • Assigned • 2.9mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

9/10 Heat Factor

7 days above 102° expected this year, 18 days in 30 years

6/10 Wind Factor

49% chance of strong winds in next 30 years

2/10 Air Factor

2 unhealthy days expected this year, 2 days in 30 years

Provided by First Street

Historical weather

Leonardtown, MD • 20650

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9.5 hours in June and 4.9 hours in December, which is comparable to the U.S. average for solar exposure.

9.5 hrs

4.9 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$379,000 – $458,000

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Home values near 23255 Hollywood Rd

Data from public records.

Address	Redfin Estimate
23275 Hollywood Rd, Leonardtown, MD 3 Beds \| 1 Baths \| 1056 Sq. Ft.	$316,028
23225 Hollywood Rd, Leonardtown, MD - Beds \| 1.5 Baths \| 1608 Sq. Ft.	$463,794

Address	Redfin Estimate
23205 Hollywood Rd, Leonardtown, MD 3 Beds \| 2 Baths \| 1835 Sq. Ft.	$474,678
23270 Hollywood Rd, Leonardtown, MD - Beds \| 1.5 Baths \| 1512 Sq. Ft.	$329,388

Address	Redfin Estimate
23215 Hollywood Rd, Leonardtown, MD - Beds \| 1.5 Baths \| 1408 Sq. Ft.	$320,803
23310 Hollywood Rd, Leonardtown, MD - Beds \| 2 Baths \| 1712 Sq. Ft.	$345,488

Property information provided by undefined .

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About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Sale history for 23255 Hollywood Rd

Tax history for 23255 Hollywood Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 20650

Home values near 23255 Hollywood Rd

More real estate resources