Date
Details
Price
Change
Source
11/16/2025
Listed
$1,900,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$1,900,000
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Property Description
Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the "Oakwood Association" belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting today's residents to St. Michaels' vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.
Full Property Details
Full Property Details for 24390 Oakwood Park Rd
General
- Price: $1,900,000
- HOA FEE: $50/month
- HOA FEE FREQ.: Annually
- Taxes: $7,046 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDTA2012326
- Updated: 12/17/2025
- Added to Site: 63 day(s) ago
Interior
- Number of Rooms: 14
- Rooms/Areas: Living Room, Dining Room, Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Family Room, Foyer, Utility Room, Bathroom 2, Bathroom 3, Primary Bathroom, Half Bath
- Interior Features: Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-Ins, Carpet, Ceiling Fan(s), Entry Level Bedroom, Exposed Beams, Floor Plan - Traditional, Kitchen - Country, Primary Bath(s), Recessed Lighting, Walk-in Closet(s), Window Treatments, Wood Floors
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Wood
- Appliances: Built-In Range, Built-In Microwave, Dishwasher, Refrigerator, Washer, Dryer
- Flooring: Wood, Carpet, Tile/Brick
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
- Main Floor Baths: 4
- Main - Full Baths: 3
- Main - 1/2 Baths: 1
Bedrooms
- Total Bedrooms: 4
- Bedrooms Main & Up: 4
Other Rooms
- Laundry: Main Floor
Additional Information
- Shared Amenities: Boat Dock/Slip, Pier/Dock, Common Grounds
- Security/Safety: Security System
Exterior
- Exterior Features: Extensive Hardscape, Gutter System
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 8
- Parking Type: Detached Garage, Driveway
- Garage Description: Garage - Front Entry, Oversized
Location
- County: TALBOT
- Subdivision: OAKWOOD PARK
- Driving Directions: From Easton to St. Michaels, left on Railroad, left on Church Neck, left on Oakwood Park Rd to end.
- Direction Faces: West
- Location Details: River
School Information
- School District: Talbot County Public Schools
- Elementary School: St. Michaels
- Middle School: St. Michaels
- High School: St. Michaels
Community
- Association: Yes
- Assoc. Name: OAKWOOD ASSOCIATION OF ST MICHAELS
- Assoc. Fees Include: Pier/Dock Maintenance, Other
- Pets Allowed: Yes
- Pets: No Pet Restrictions
Heating & Cooling
- Cooling Type: Other
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Water Heater: Electric
Utilities
- Sewer: On Site Septic
- Water: Well
Structural Information
- Architectural Style: Traditional, Ranch/Rambler
- Structure Type: Detached
- Construction: Mixed
- Foundation: Crawl Space, Slab
- Roof: Architectural Shingle
- Walls/Ceilings: 9'+ Ceilings, Dry Wall, Vaulted Ceilings
- Stories/Levels: 1
- Stories Description: Main
- Square Feet: 2,839
- Sq. Ft. Source: Estimated
- Living Area: 2,839 Sq. Ft.
- Finished Above Grnd: 2,839 Sq. Ft.
- Year Built: 1978
- Year Built Source: Estimated
- Property Condition: Excellent
Lot Features
- Property View: Water, River, Scenic Vista
- Lot Size (Acres): 0.7
- Lot Size (Sq. Ft.): 30,492
- Lot Size Source: Estimated
- Lot Dimensions: rectangular
- Street/Road Desc.: Black Top
- Zoning: RC
- Lot Description: Cul-de-sac, No Thru Street, Premium, Rip-Rapped, Stream/Creek
Water Features
- Water Front: Yes
- Water View: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Front Type: River
- Water Front Name: San Domingo Creek
Financial Considerations
- Price Per Sq. Ft.: $669.25
- Association Fee: $600
- Assoc Fee Freq.: Annually
- Assessment Year: 2025
- County Tax: $7,046
- County Tax Freq: Annually
- Tax w/Assessment: $769,900
- Tax Amount: $7,046
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 2839
Disclosures and Reports
- Ownership: Fee Simple
- Exclusions: Tori Lantern Statue in backyard
- Inclusions: All appliances and mechanicals currently on site. Safe.
- Lot Number: 3
Listed by Benson & Mangold, LLC, Janet R Larson and Benson & Mangold, LLC, Henry S Hale
We Value Your Privacy
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We Value Your Privacy
Listing agents
— 24390 Oakwood Park Rd —
Janet R Larson
Benson & Mangold, LLC
Henry S Hale
Benson & Mangold, LLC
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 24390 Oakwood Park Rd
School District:Talbot County Public Schools
| Name | Grades | Distance |
|---|---|---|
St. Michaels Elementary School 100 Seymour Avenue, Saint Michaels, MD 21663 | PK-6 | 1.1 mi |
St. Michaels Middle/High School 200 Seymour Avenue, Saint Michaels, MD 21663 | 7-12 | 1 mi |
Easton High School 723 Mecklenburg Avenue, Easton, MD 21601 | 9-12 | 9 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 24390 Oakwood Park Rd
Tax History
Tax History for 24390 Oakwood Park Rd
Year
Property Taxes
Change
Tax Assessment
Change
2023
$3,311
—
$769,900
5%
2023
$3,311
—
$732,067
5%
2023
$3,311
-36%
$694,233
6%
2022
$5,212
78%
$656,400
2%
2020
$2,935
1%
$642,233
2%
2021
$2,913
1%
$628,067
2%
2020
$2,897
3%
$613,900
—
2019
$2,813
4%
$613,900
—
2018
$2,693
2%
$613,900
-4%
2017
$2,639
1%
$637,600
—
2016
$2,601
1%
$637,600
—
2015
$2,570
-2%
$637,600
-13%
2014
$2,623
—
$730,300
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 24390 Oakwood Park Rd
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- Single Family
- Active
- Updated 5 days ago
- 6Beds
- 4Total Baths
- 1,454Sq. Ft.
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- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,321Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 2Total Baths
- 1,976Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 6Total Baths
- 6,184Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 3Beds
- 3Total Baths
- 2,660Sq. Ft.
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- Single Family
- Active
- Updated 5 days ago
- 6Beds
- 4Total Baths
- 1,454Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 1Bed
- 1Total Bath
- 832Sq. Ft.
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,834Sq. Ft.
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 3Total Baths
- 2,288Sq. Ft.
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24390 Oakwood Park Road, Saint Michaels, MD 21663 (MLS# MDTA2012326) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 24390 Oakwood Park Road is currently listed for $1,900,000 and was received on November 16, 2025. Want to learn more about 24390 Oakwood Park Road? Do you have questions about finding other Single Family real estate for sale in Saint Michaels? You can browse all Saint Michaels real estate or contact a Coldwell Banker agent to request more information.