24390 Oakwood Park Road, ST MICHAELS, MD 21663 (MLS # MDTA2012326)
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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.
Property Type(s):
Single Family
| Last Updated | 11/16/2025 | Tract | OAKWOOD PARK |
|---|---|---|---|
| Year Built | 1978 | Garage Spaces | 2.0 |
| County | TALBOT |
SCHOOLS
| School District | TALBOT COUNTY PUBLIC SCHOOLS |
|---|---|
| Elementary School | ST. MICHAELS |
| Jr. High School | ST. MICHAELS |
| High School | ST. MICHAELS |
Additional Details
| AIR | Ceiling Fan(s), Electric, Other |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Built-In Range, Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer |
| BASEMENT | Crawl Space |
| EXTERIOR | Rain Gutters |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Electric, Heat Pump |
| HOA DUES | 600|Annually |
| INTERIOR | Beamed Ceilings, Built-in Features, Ceiling Fan(s), High Ceilings, Recessed Lighting, Vaulted Ceiling(s), Walk-in Closet(s) |
| LOT | 0.7 acre(s) |
| LOT DESCRIPTION | Cul-de-sac, Waterfront |
| LOT DIMENSIONS | rectangular |
| PARKING | Oversized, Garage, Driveway, Detached |
| POOL DESCRIPTION | None |
| SEWER | Septic Tank |
| STORIES | 1 |
| STYLE | Ranch/Rambler, Traditional |
| SUBDIVISION | OAKWOOD PARK |
| TAXES | 7046 |
| UTILITIES | Cable Available |
| VIEW | Yes |
| VIEW DESCRIPTION | Water, River, Scenic |
| WATER | Well |
| WATER ACCESS | San Domingo Creek |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | River Front, Stream |
| ZONING | Rural Conservation |
Location
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Listing provided by Benson & Mangold, LLC
The multiple listing data appearing on this website, or contained in reports produced therefrom, comes in part from Metropolitan Regional Information Systems ("MRIS"). The information provided is for the viewer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. All real estate listings include detailed information about them that includes the name of the listing brokers and therefore may reference real estate listing(s) held by a brokerage other than the broker and/or agent who owns this web site.
All listing data, including, but not limited to, square footage and lot size is believed to be accurate, but the listing agent, listing broker and respective Multiple Listing Services and their affiliates do not warrant or guarantee such accuracy. Therefore, all data should be personally verified through personal inspection by and/or with the appropriate professionals. Listing data last updated 11/18/25 6:08 PM PST.
The listing information on this web site is from various brokers who participate in IDX.
Copyright 2025 MRIS. All rights reserved.
All listing data, including, but not limited to, square footage and lot size is believed to be accurate, but the listing agent, listing broker and respective Multiple Listing Services and their affiliates do not warrant or guarantee such accuracy. Therefore, all data should be personally verified through personal inspection by and/or with the appropriate professionals. Listing data last updated 11/18/25 6:08 PM PST.
The listing information on this web site is from various brokers who participate in IDX.
Copyright 2025 MRIS. All rights reserved.
This IDX solution is (c) Diverse Solutions 2025.