Last Sold Price
3 beds1,344 sqft$309/sqft
23745 Bayside Rd, Leonardtown, MD 20650

Description

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...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!
LISTING CLOSED: 10/24/2025 12:00 AM

  1. Listed by Delaney I Burgess • RE/MAX United Real Estate
    P: (301) 938-0100 delaney@delaneyburgessrealtor.com

Property Details for 23745 Bayside Road

Status
MLS #
MDSM2026368
Days on Market
5
Taxes
$2,036 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
MLS Type
Residential / Fee Simple
Year Built
1975
Lot Size
1.00 AC / 43,560 SF
Tax ID Number
1903026132
Ownership
Fee Simple
Condo Coop Association
No
HOA
No
Structure Type
Detached
Style
Ranch/Rambler
Levels/Stories
2
Waterfront
No
Views
Trees/Woods
Garage
Yes
Subdivision
NONE AVAILABLE
Subdivision
NONE AVAILABLE (SAINT MARYS MD)
Total Parking Spaces
1
Central Air
Yes
Basement
Yes
Above Grade Finished SQFT
1,344.00
Above Grade Fin SQFT Source
Assessor
Below Grade Finished SQFT
.00
Below Grade Fin SQFT Source
Assessor
Below Grade Unfinished SQFT
1,344.00
Below Grade Unfin SQFT Source
Assessor
Total Below Grade SQFT
1,344.00
Total Below Grade SQFT Source
Assessor
New Construction
No
Property Condition
Excellent, Very Good

Recent comparable sales

Median sold price

$375,000

Avg days on market

42

Sale-to-list ratio

97.8%

Leonardtown, MD

9 comparable properties found

a view of swimming pool with outdoor seating
1/28
1

$375,000

Sold 03/07/25

3
Bedrooms
1,456
Square Feet
0.23
Acres
a view of a house with a yard
1/28
2

$335,000

Sold 07/07/26

3
Bedrooms
1,287
Square Feet
0.17
Acres
a view of a yard in front of a house with a large tree
1/52
3

$415,000

Sold 06/09/25

3
Bedrooms
1,348
Square Feet
0.46
Acres
$340,000 | 22281 Nomoni Street, Leonardtown, MD 20650
1/43
4

$340,000

Sold 07/31/26

3
Bedrooms
1,152
Square Feet
0.28
Acres
$335,000 | 39834 Big Pine Trail, Leonardtown, MD 20650
1/13
5

$335,000

Sold 11/12/24

3
Bedrooms
1,344
Square Feet
0.22
Acres
a front view of a house with a garden and yard
1/51
6

$406,000

Sold 07/25/25

3
Bedrooms
984
Square Feet
0.6
Acres
a kitchen with stainless steel appliances a stove microwave and sink
1/26
7

$402,000

Sold 10/31/25

3
Bedrooms
1,992
Square Feet
0.6
Acres
a front view of a house with a yard and garage
1/3
8

$400,000

Sold 08/18/25

3
Bedrooms
1,380
Square Feet
0.71
Acres
a front view of a house with a yard
1/2
9

$366,000

Sold 07/02/25

3
Bedrooms
1,856
Square Feet
1.26
Acres

Location

Listing Courtesy of RE/MAX United Real Estate

Sold By CENTURY 21 New Millennium

Add your commute

Building Information for 23745 Bayside Road

Stories2Year Built1975Building Size-Lot Size1.00 AC / 43,560 SF

Payment Calculator

Get preapproved with
OriginPoint Mortgage or Rocket Mortgage1

$2,279 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,109

Property Taxes

$170

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 23745 Bayside Road

Location
Location
  • In City Limits: No
  • School District Name: ST. MARYS COUNTY PUBLIC SCHOOLS
  • School District County ID: 803197649142
  • SchoolDistrictSource: 3rd Party
  • Middle Or Junior School: LEONARDTOWN (SAINT MARYS MD)
  • MiddleSchoolSource: 3rd Party
  • High School: CHOPTICON (SAINT MARYS MD)
  • HighSchoolSource: 3rd Party
  • County: SAINT MARYS
Waterfront / Water Access
Waterfront / Water Access
  • Water View: No
  • Water Access: No
  • Water Oriented: No
  • Navigable Water: No
  • Tidal Water: No
  • Riparian Rights Y/N: No
Association / Community Info
Association / Community Info
  • Senior Community: No
  • Association Recreation Fee Y/N: No
Taxes and Assessment
Taxes and Assessment
  • Tax Year: 2024
  • Tax Assessed Value: $224,500
  • Year Assessed: 2025
  • County Tax: $2,036
  • Improvement Assessed Value: $110,500
  • Land Assessed Value: $114,000
  • Clean Green Assessed: No
  • Land Use Code: R
  • Zoning: RPD
  • School Tax: $0
  • Automatically Update Tax Values Y/N: Yes
Rooms
Main
  • # Bedrooms Count Main Level: 3
  • # Bathrooms Count Main Level: 2
  • # Bathrooms Full Main Level: 2
Rooms
  • Room List: Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Kitchen, Family Room, Bathroom 2, Primary Bathroom
  • Stories: Main
Rooms Information
Room 1
  • Room Type: Family Room
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Luxury Vinyl Plank
Room 2
  • Room Type: Kitchen
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Luxury Vinyl Plank
Room 3
  • Room Type: Primary Bedroom
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Carpet
Room 4
  • Room Type: Bedroom 2
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Carpet
Room 5
  • Room Type: Bedroom 3
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Carpet
Room 6
  • Room Type: Primary Bathroom
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Luxury Vinyl Plank
Room 7
  • Room Type: Bathroom 2
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Luxury Vinyl Plank
Room 8
  • Room Type: Dining Room
  • Room Level: Main
  • Room Exists: Yes
  • Room Features: Flooring - Luxury Vinyl Plank
Building Info
Building Info
  • Year Major Reno Remodel: 2024
  • Total Finished SQFT: 1,344.00
  • Total Finished SQFT Source: Assessor
  • Tax Total Finished SQFT: 1,344.00
  • Total SQFT: 2,688.00
  • Total SQFT Source: Assessor
  • Construction Materials: Frame
  • Basement Type: Unfinished, Walkout Level, Space For Rooms, Side Entrance, Outside Entrance, Interior Access
  • Foundation Details: Slab
  • Room and Floor: Bedrooms-Main Level-1, Bedrooms-Main Level-2, Bedrooms-Main Level-3, Bathrooms Full-Main Level-1, Bathrooms Full-Main Level-2
  • # Bathrooms Full: 2
  • Other Structure: Above Grade, Below Grade
Lot / Land Information
Lot / Land Information
  • Lot Size Source: Assessor
  • Parcel ID: 14988901
  • Additional Parcels: No
Parking
Parking
  • Type Of Parking: Attached Garage, Driveway
  • Num of Attached Garage Spaces: 1
  • Total Garage Spaces: 1
  • Parking Features: Gravel Driveway
  • Garage Features: Garage - Rear Entry, Basement Garage, Garage - Side Entry
Interior Features
Interior Features
  • Interior Features: Attic, Ceiling Fan(s), Dining Area, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Country, Primary Bath(s), Recessed Lighting, Upgraded Countertops
  • Fireplace: Yes
  • Fireplaces Count: 1
  • Fireplace Features: Brick, Other
  • Appliances: Built-In Microwave, Dishwasher, Exhaust Fan, Icemaker, Oven/Range - Electric, Refrigerator, Stainless Steel Appliances, Water Heater
  • Accessibility Features: None
  • Laundry Type: Basement, Hookup
Exterior Features
Exterior Features
  • Pool: No Pool
Utilities
Utilities
  • Heating: Yes
  • Cooling Type: Central A/C, Heat Pump(s)
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump - Electric BackUp
  • Heating Fuel: Electric
  • Hot Water: Electric
  • Water Source: Well
  • Sewer Septic: Private Septic Tank
Confidential Data
Listing Office
  • List Agent AOR: Southern Maryland Association of REALTORS
  • List Agent URL: delaneyburgessrealtor.com

Property History for 23745 Bayside Road

DateEvent & SourcePriceAppreciation
Oct 24, 2025

Closed (Public Record)

Public Record #1920931383

$415,000

+4.0% / yr

Oct 24, 2025

Closed

BRIGHT #MDSM2026368

$415,000
Sep 13, 2025

Pending

BRIGHT #MDSM2026368

DateEvent & SourcePrice
10/24/2025

Closed (Public Record)

Public Record #1920931383

$415,000

+4.0% / yr

10/24/2025

Closed

BRIGHT #MDSM2026368

$415,000
09/13/2025

Pending

BRIGHT #MDSM2026368

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 23745 Bayside Road

Taxable ValueLand-Additions-Total-
Tax Record2025$2,566 ($214 / month)
Home Facts
Beds0Baths2.5Total Finished SqFt1,344 SqFtAbove Grade Finished SqFt1,344 SqFtStories1Lot Size43,560 SqFtStyleSingle Family ResidenceYear Built1975Year Renovated1975ZoningRPDCountyST. MARY'SAPN03-026132

Schools near 23745 Bayside Road

This home is within St. Mary's County Public Schools.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Public - 9 to 12
Rating
School
Distance
Benjamin Banneker Elementary School
PublicPK to 5

Leonardtown Middle School
Public6 to 8

Chopticon High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 20650

$750,000 | 40579 Port Place, Leonardtown, MD 20650
1/73
New

$750,000

3
Bedrooms
2,304
Square Feet
0.8
Acres
$714,900 | 23760 Coventry Drive, Leonardtown, MD 20650
Coming Soon

$714,900

5
Bedrooms
4,744
Square Feet
0.32
Acres
$470,000 | 41614 Briarwood Circle, Leonardtown, MD 20650
Active Under Contract

$470,000

4
Bedrooms
2,816
Square Feet
0.11
Acres
$650,000 | 40751 Merlin Way, Leonardtown, MD 20650
1/43

$650,000

5
Bedrooms
2,601
Square Feet
3.21
Acres
$600,000 | 41524 Fairwood Court, Leonardtown, MD 20650
Coming Soon

$600,000

4
Bedrooms
3,793
Square Feet
0.16
Acres
$624,990 | 40611 Merion Court, Leonardtown, MD 20650
1/58

$624,990

4
Bedrooms
2,562
Square Feet
0.43
Acres
$749,900 | 41402 Omaha Court, Leonardtown, MD 20650
1/4
Coming Soon

$749,900

5
Bedrooms
4,873
Square Feet
0.64
Acres
$449,900 | 139-23665 Dragonfly Lane, Leonardtown, MD 20650
1/42
Open: 8/21 11:00AM - 04:00PMNew Construction

$449,900

4
Bedrooms
Unavailable
Square Feet
0.05
Acres
$449,900 | 143-23641 Dragonfly Lane, Leonardtown, MD 20650
1/42
New Construction

$449,900

4
Bedrooms
Unavailable
Square Feet
0.05
Acres

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 23745 Bayside Road, Leonardtown, MD 20650
$415,000
3
1,344
43,560
2.5
2,328
12,314,413
2
1,752
137,650
2
728
64,033
2
1,568
96,703
2
1,784
193,842

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of RE/MAX United Real Estate

© 2026 Bright MLS. All rights reserved. All information is deemed reliable, but accuracy is not guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated on 10/28/2025 04:45 PM