Change Real Estate Presents:

24390 Oakwood Park Road
Saint Michaels MD 21663

For Sale: $1,679,000.00 Active

List Date: 2025-11-16

Saint Michaels
4 bedrooms
4 bathrooms
2,839 build ft2
30,492 land ft2

About This Property

OPEN HOUSE SUNDAY 5/17 11am to 1pm! Significant price improvement! 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.

Listing Agent: Janet R Larson. Benson & Mangold, LLC 410-310-1797 jlarson@bensonandmangold.com

Virtual Tours / Videos

https://thru-the-lens-ivuf.view.property/2353581?idx=1

Property Features

Location Information
County:
Subdivision: OAKWOOD PARK
click to open map in a new window
Interior Features
Appliances: Built-In Range, Built-In Microwave, Dishwasher, Refrigerator, Washer, Dryer
Interior: 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
Laundry:
Furnished: None
Flooring: Wood, Carpet, Tile/Brick
Water: Well
Cooling: Other
Heating: Heat Pump(s)
Fireplaces: 1
Windows:
Utilities:
Sewer: On Site Septic
Rooms
Room Type: Living Room
Features: Fireplace - Wood Burning, Flooring - Wood, Cathedral/Vaulted Ceiling, Built-Ins
Level: Main
Room Type: Family Room
Features: Flooring - Carpet
Level: Main
Room Type: Dining Room
Features: Flooring - Carpet
Level: Main
Room Type: Kitchen
Features: Flooring - Wood, Cathedral/Vaulted Ceiling, Pantry
Level: Main
Room Type: Primary Bedroom
Features: Flooring - Wood, Cathedral/Vaulted Ceiling, Attached Bathroom, Walk-In Closet(s), Fireplace - Wood Burning
Level: Main
Room Type: Primary Bathroom
Features: Flooring - Ceramic Tile, Double Sink
Level: Main
Room Type: Bedroom 2
Features: Flooring - Carpet, Cathedral/Vaulted Ceiling, Attached Bathroom, Walk-In Closet(s)
Level: Main
Room Type: Bathroom 2
Features: Bathroom - Tub Shower, Double Sink
Level: Main
Room Type: Bedroom 3
Features: Flooring - Carpet, Ceiling Fan(s)
Level: Main
Room Type: Bedroom 4
Features: Flooring - Wood, Ceiling Fan(s)
Level: Main
Room Type: Bathroom 3
Features: Bathroom - Tub Shower, Flooring - Ceramic Tile
Level: Main
Room Type: Half Bath
Features: Flooring - Ceramic Tile
Level: Main
Room Type: Utility Room
Level: Main
Room Type: Foyer
Features: Flooring - Wood
Level: Main
Exterior Features
Year Built: 1978
Legal Subdivision: 21020094
Subdivision Name: Oakwood Park
Exterior Features: Extensive Hardscape, Gutter System
Garage Spaces: 2.0
Association Fee: $600.00 (Annually)
Association Amenities: Boat Dock/Slip, Pier/Dock, Common Grounds
Schools
Elementary School: St. Michaels
Junior High School: St. Michaels
High School: St. Michaels

IDXListing Courtesy of Janet R Larson. Benson & Mangold, LLC 410-310-1797 jlarson@bensonandmangold.com

Property Photos [Click to enlarge]

Bright © 2026 Bright, All Rights Reserved.

The data related to real estate for sale on this website comes in part from the INTERNET DATA EXCHANGE (IDX) program of the Bright MLS. Real estate listings held by brokerage firms other than this site owner are marked with the IDX logo.

IDX information is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation or other purposes. All listing information is deemed reliable but not guaranteed.

This content was last refreshed on 2026-06-04 08:46 AM. Some properties which appear for sale on this website may subsequently have sold or may no longer be available.

DMCA Notice