SOLD OCT 24, 2025

Off Market Oct 2025 for $415K

$435,853

Est. refi paymentEst. refi $2,859/mo

•

1,344

sq ft

23745 Bayside Rd, Leonardtown, MD 20650

About this home

* Offer Deadline for Friday, September 12th, no later than 6PM. * Privacy, peace and pristine are all words that describe 23745 Bayside Road. This three bedroom, two bath rambler has been fully updated with today's modern finishes and custom features like wood pantry shelving & other great features, giving you style in every room. Nestled on one acre of extremely private land with a long winding driveway, this home welcomes you with an abundance of natural light, brand new LVP flooring throughout the main level and so much more. The kitchen shines as the centerpiece, complete with white cabinetry, stainless steel appliances, and granite countertops overlooking your large living room. Both bathrooms have been beautifully renovated with today’s trends in mind and the newer HVAC system ensures year-round comfort. A spacious unfinished basement with painted floors, and one-car garage provides plenty of storage and potential for customization. Fresh landscaping and professional power washing add to the properties excellent curb appeal. With no HOA you’ll have the freedom to enjoy YOUR property YOUR way. Located just minutes from Leonardtown shops, dining and waterfront experiences. This home offers privacy without sacrificing inconvenience. Don’t miss the opportunity to make this your next home, schedule a private tour today!

Single-familyProperty Type

1975Year Built

1 acresLot Size

$324Est. Price/Sq.Ft.

1 car garageParking

Listed by Delaney Clarke • RE/MAX United Real Estate

•301-702-4200 (broker)

Bought with Ruth Williams • CENTURY 21 New Millennium

•301-609-9000 (broker)

•courtney.murphy@c21nm.com (broker)

Redfin checked: 2 minutes ago

•Source:BRIGHT MLS #MDSM2026368

Redfin Estimate

$435,853

$21K since sold in October 2025$1,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.4% higher than the average sale price ($384K) of 5 comparable homes.

SOLD JUN 2, 2026
$530,000
A
3 beds2.5 baths1,926 sq ft
23207 Moakley St, Leonardtown, MD 20650
SOLD JUL 31, 2026
$340,000
B
3 beds2 baths1,152 sq ft
22281 Nomoni St, Leonardtown, MD 20650
SOLD JUL 7, 2026
$335,000
C
3 beds2 baths1,287 sq ft
22381 Cedar St, Leonardtown, MD 20650
SOLD OCT 31, 2025
$402,000
D
3 beds2 baths1,992 sq ft
23730 Hicks Dr, Leonardtown, MD 20650
SOLD MAY 28, 2026
$315,000
E
2 beds2 baths1,192 sq ft
22175 Bayside Rd, Leonardtown, MD 20650

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Earn from this home

Sell

$81,750

Est. take-home

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Refinance

Est. cash available

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Rent

$1,983/mo

Redfin rental estimate

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Market trends in 20650, MD

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.2%

+0.4% MoM

Median sale price

$566K

$126 MoM

Avg. days on market

43d

0 days MoM

Recently sold homes

6 MoM

New listings for sale

LISTED BY REDFIN 55 MINS AGO
$435,000
4 beds2.5 baths2,624 sq ft
40717 Lake And Breton View Dr, Leonardtown, MD 20650
$695,000
5 beds2.5 baths2,953 sq ft
44450 Schumann Way, Leonardtown, MD 20650
(301) 862-2169
$749,900
5 beds4 baths4,873 sq ft
41402 Omaha Ct, Leonardtown, MD 20650
(855) 450-0442
$550,000
4 beds3.5 baths2,562 sq ft
41888 Jenkins Ct, Leonardtown, MD 20650
(301) 884-9493
$780,000
5 beds4 baths5,484 sq ft
22601 Avenmar Dr, Leonardtown, MD 20650
(301) 862-2169
OPEN SAT, 10AM TO 12PM
$600,000
4 beds3 baths3,793 sq ft
41524 Fairwood Ct, Leonardtown, MD 20650
(301) 298-2892
$475,000
4 beds2.5 baths2,774 sq ft
40659 Klear Ct, Leonardtown, MD 20650
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EARLY ACCESS
$625,000
4 beds3.5 baths2,736 sq ft
23354 Lindsay Dr, Leonardtown, MD 20650
$714,900
5 beds4 baths4,744 sq ft
23760 Coventry Dr, Leonardtown, MD 20650
(301) 862-2169
See all

Provided by Redfin

Sale history for 23745 Bayside Rd

Date

Event

Price

BRIGHT MLS #MDSM2026368

Oct 24, 2025

Sold

$415,000

$309/sq ft

Sep 25, 2025

Pending

—

Sep 13, 2025

Contingent

—

Sep 9, 2025

Listed

$399,900

$298/sq ft

BRIGHT MLS #MDSM2016924

Mar 22, 2024

Sold

$389,900

$290/sq ft

Feb 14, 2024

Contingent

—

Feb 5, 2024

Listed

$399,900

$298/sq ft

Jan 21, 2024

Coming Soon

$399,900

$298/sq ft

+15

Welcome to 23745 Bayside Rd, Leonardtown, MD – where charm meets modernity in this impeccably renovated residence. This stunning home has undergone a total transformation, leaving no stone unturned in its quest for contemporary excellence. Boasting a brand-new roof, HVAC system, plumbing, electric wiring, and appliances, this property shines like a new penny, offering a turnkey experience for its fortunate new owners. Step inside to discover a seamless blend of classic elegance and cutting-edge design. The spacious living areas are adorned with high-quality finishes and fixtures, creating an inviting atmosphere for both relaxation and entertainment. The thoughtfully redesigned kitchen is a culinary enthusiast's dream, featuring state-of-the-art appliances that seamlessly integrate with the sleek, modern aesthetics. Situated on an expansive one-acre wooded lot, this home provides a serene and private escape. The lush green surroundings offer a picturesque backdrop, allowing residents to enjoy nature's beauty right at their doorstep. Whether you're sipping coffee on the deck or hosting gatherings in the backyard, this property provides the perfect setting for creating lasting memories. Convenience and comfort go hand-in-hand with the modern amenities throughout the home. With the new HVAC system in place, climate control is a breeze, ensuring year-round comfort. The meticulous attention to detail in the renovation ensures that this home not only meets but exceeds the expectations of modern living. Don't miss the opportunity to own a piece of Leonardtown's finest real estate, where classic charm meets contemporary luxury. 23745 Bayside Rd is more than a home; it's a statement of refined living, where every detail has been carefully curated to provide a lifestyle of comfort and sophistication. Schedule a viewing today and experience the allure of this completely renovated gem.

BRIGHT MLS #MDSM2014650

Aug 22, 2023

Sold

$136,000

$101/sq ft

Aug 11, 2023

Pending

—

Aug 8, 2023

Listed

$125,000

$93/sq ft

+17

BRIGHT MLS #MDSM2014652

Aug 11, 2023

Listing Removed

—

Aug 8, 2023

Listed

$125,000

$93/sq ft

Public Records

Dec 8, 1993

Sold

$112,500

$84/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$2,566 (+7.5%)

2024

$2,387 (+8.9%)

$114,000 + $110,500

$224,500

2023

$2,191 (+8.2%)

2021

$2,024 (+2.0%)

$115,000 + $72,300

$187,300

2020

$1,985 (+2.0%)

2019

$1,946

2018

$1,945 (+1.0%)

$110,000 + $66,400

$176,400

2017

$1,926 (+8.1%)

$110,000 + $66,400

$176,400

2015

$1,781 (−5.7%)

2014

$1,888 (+2.2%)

$105,000 + $68,700

$173,700

2013

$1,847 (+5.9%)

2012

$1,744 (+2.2%)

2011

$1,708

2010

$1,708 (+23.7%)

2009

$1,381

Tax history for 23745 Bayside Rd

Year

Property tax

Land + Additions

Assessment*

2025

$2,566 (+7.5%)

2024

$2,387 (+8.9%)

$114,000 + $110,500

$224,500

2023

$2,191 (+8.2%)

2021

$2,024 (+2.0%)

$115,000 + $72,300

$187,300

2020

$1,985 (+2.0%)

2019

$1,946

2018

$1,945 (+1.0%)

$110,000 + $66,400

$176,400

2017

$1,926 (+8.1%)

$110,000 + $66,400

$176,400

2015

$1,781 (−5.7%)

2014

$1,888 (+2.2%)

$105,000 + $68,700

$173,700

2013

$1,847 (+5.9%)

2012

$1,744 (+2.2%)

2011

$1,708

2010

$1,708 (+23.7%)

2009

$1,381

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

Public record

Public record
Permits

Beds

—

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1 Acre

Year renovated

—

Sq. Ft.

1,344

Year built

1975

Style

Single Family Residential

County

St. Mary's County

APN

03 026132

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 18, 2026.

Property details

Parking

Parking Information
# of Attached Garage Spaces: 1
Garage Features: Garage - Rear Entry, Basement Garage, Garage - Side Entry
# of Total Garage and Parking Spaces: 1
Has Garage
# of Garage Spaces: 1
Gravel Driveway
Attached Garage, Driveway

Interior

Bedroom Information
# of Bedrooms On Main Level: 3

Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2

Interior Information
Appliances: Built-In Microwave, Dishwasher, Exhaust Fan, Icemaker, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Water Heater
Interior Features: Attic, CeilngFan(s), Dining Area, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Country, Master Bath(s), Recessed Lighting, Upgraded Countertops
Living Area Sq.Ft. Source: Assessor

Room Information
Dining Room, Master Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Bathroom 2, Master Bathroom
Laundry Type: Basement, Hookup

Fireplace Information
Has Fireplace
# of Fireplaces: 1
Brick, Other

Basement Information
Basement: Yes
Unfinished, Walkout Level, Space For Rooms, Side Entrance, Outside Entrance, Interior Access

Exterior

Property Information
Not Federal Flood Zone
Total Below Grade Sq. Ft.: 1344
Improvement Assessed Value: $110,500
Ownership Interest: Fee Simple
Property Condition: Excellent, Very Good
Year Built Source: Assessor
Year Major Reno/Remodel: 2024

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

Lot Information
Tidal Water: No

Land Information
Land Assessed Value: $114,000

Above Grade Information
Finished Sq.Ft.: 1,344
Finished Sq.Ft. Source: Assessor

Below Grade Information
Unfinished Sq.Ft.: 1,344
Unfinished Sq.Ft. Source: Assessor
Finished Sq.Ft. Source: Assessor

Financial

Tax Information
County Tax: $2,036
Tax Assessed Value: $224,500
Tax Year: 2024
Tax Annual Amount: $2,036

Assessments Information
Year Assessed: 2025

Lease Information
Lease Considered: No

Utilities

Utilities Information
Central Air
Cooling Type: Central A/C, Heat Pump(s)
Cooling Fuel: Electric
Heat Pump - Electric BackUp
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Private Septic Tank
Water Source: Well

Location

School Information
Middle Or Junior School: LEONARDTOWN
High School: CHOPTICON
School District Name: ST. MARYS COUNTY PUBLIC SCHOOLS
Middle School Source: 3rd Party
High School Source: 3rd Party
School District Source: 3rd Party

Location Information
Outside City Limits
Directions: AGENTS: Please read!! From Budd's Creek Road (MD-234), and turning onto Bayside Road, your GPS is going to want to take you down Montpelier Lane - DO NOT TURN DOWN THIS ROAD, YOU HAVE GONE TOO FAR. The driveway is hidden and will be on your right. The entrance to the driveway is almost right across the little rambler house on your left. It will be a gravel driveway. Look for the signs and please follow instructions.

Public facts

Beds: —
Baths: 2.0
Sq. Ft.: 1,344
Stories: 1.0
Lot Size: 1 acres
Style: Single Family Residential
Year Built: 1975
Year Renovated: —
County: St. Mary's County
APN: 03 026132

Home facts updated by county records on Jul 18, 2026

Around this home

Schools

Benjamin Banneker Elementary School

Public PreK-5 • Assigned • 2.2mi

8/10

Leonardtown Middle School

Public 6-8 • Assigned • 6.2mi

9/10

Chopticon High School

Public 9-12 • Assigned • 2.9mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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 9.6 hours in June and 4.8 hours in December, which is comparable to the U.S. average for solar exposure.

9.6 hrs

4.8 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$415,000 – $502,000

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Home values near 23745 Bayside Rd

Data from public records.

Address	Redfin Estimate
23430 Bayside Road, Leonardtown, MD - Beds \| 2.5 Baths \| 2076 Sq. Ft.	$444,273
23614 Bayside Road, Leonardtown, MD - Beds \| 2 Baths \| 728 Sq. Ft.	$289,786

Address	Redfin Estimate
23364 Bayside Road, Leonardtown, MD 3 Beds \| 2 Baths \| 1152 Sq. Ft.	$394,420
23610 Bayside Road, Leonardtown, MD - Beds \| 2 Baths \| 1752 Sq. Ft.	$400,257

Address	Redfin Estimate
23267 Bayside Road, Leonardtown, MD - Beds \| 2 Baths \| 1664 Sq. Ft.	$473,479
23408 Bayside Road, Leonardtown, MD - Beds \| 1 Baths \| 1456 Sq. Ft.	$396,488

Property information provided by BRIGHT MLS when last listed in 2025. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 20650, MD

Sale history for 23745 Bayside Rd

Tax history for 23745 Bayside Rd

Public record

Property details

Around this home

Schools

Lifestyle

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 20650

Home values near 23745 Bayside Rd

More real estate resources