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.
For sale
Price cut: $146K (4/18)
$1,679,000
24390 Oakwood Park Rd, Saint Michaels, MD 21663
4beds
2,839sqft
Single Family Residence
Built in 1978
0.7 Acres Lot
$1,594,800 Zestimate®
$591/sqft
$50/mo HOA
What's special
Rustic wood-burning fireplaceWaterfront family roomCustom built-insModern appliancesLarge rear waterside deckHandsome cabinetryTwo-car detached garage
- 231 days |
- 1,190 |
- 50 |
Zillow last checked:
Listing updated:
Listed by:
Janet Larson 410-310-1797,
Benson & Mangold, LLC (410) 745-0415,
Co-Listing Agent: Henry S Hale 410-829-3777,
Benson & Mangold, LLC
Source: Bright MLS,MLS#: MDTA2012326
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
- Main level bathrooms: 4
- Main level bedrooms: 4
Rooms
- Room types: 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
Primary bedroom
- Features: Flooring - Wood, Cathedral/Vaulted Ceiling, Attached Bathroom, Walk-In Closet(s), Fireplace - Wood Burning
- Level: Main
- Area: 280 Square Feet
- Dimensions: 20 X 14
Bedroom 2
- Features: Flooring - Carpet, Cathedral/Vaulted Ceiling, Attached Bathroom, Walk-In Closet(s)
- Level: Main
- Area: 294 Square Feet
- Dimensions: 21 X 14
Bedroom 3
- Features: Flooring - Carpet, Ceiling Fan(s)
- Level: Main
- Area: 154 Square Feet
- Dimensions: 11 X 14
Bedroom 4
- Features: Flooring - Wood, Ceiling Fan(s)
- Level: Main
- Area: 132 Square Feet
- Dimensions: 11 X 12
Primary bathroom
- Features: Flooring - Ceramic Tile, Double Sink
- Level: Main
- Area: 130 Square Feet
- Dimensions: 13 X 10
Bathroom 2
- Features: Bathroom - Tub Shower, Double Sink
- Level: Main
Bathroom 3
- Features: Bathroom - Tub Shower, Flooring - Ceramic Tile
- Level: Main
- Area: 48 Square Feet
- Dimensions: 8 X 6
Dining room
- Features: Flooring - Carpet
- Level: Main
- Area: 168 Square Feet
- Dimensions: 14 X 12
Family room
- Features: Flooring - Carpet
- Level: Main
- Area: 324 Square Feet
- Dimensions: 27 X 12
Foyer
- Features: Flooring - Wood
- Level: Main
- Area: 108 Square Feet
- Dimensions: 12 X 9
Half bath
- Features: Flooring - Ceramic Tile
- Level: Main
- Area: 16 Square Feet
- Dimensions: 4 X 4
Kitchen
- Features: Flooring - Wood, Cathedral/Vaulted Ceiling, Pantry
- Level: Main
- Area: 266 Square Feet
- Dimensions: 19 X 14
Living room
- Features: Fireplace - Wood Burning, Flooring - Wood, Cathedral/Vaulted Ceiling, Built-in Features
- Level: Main
- Area: 392 Square Feet
- Dimensions: 28 X 14
Utility room
- Level: Main
- Area: 18 Square Feet
- Dimensions: 3 X 6
Heating
- Heat Pump, Electric
Cooling
- Other, Electric
Appliances
- Included: Built-In Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Electric Water Heater
- Laundry: Main Level
Features
- Bathroom - Walk-In Shower, Bathroom - Tub Shower, Built-in Features, Ceiling Fan(s), Entry Level Bedroom, Exposed Beams, Floor Plan - Traditional, Kitchen - Country, Primary Bath(s), Recessed Lighting, Walk-In Closet(s), 9'+ Ceilings, Dry Wall, Vaulted Ceiling(s)
- Flooring: Wood, Carpet, Tile/Brick
- Windows: Window Treatments
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Wood Burning
Interior area
- Total structure area: 2,839
- Total interior livable area: 2,839 sqft
- Finished area above ground: 2,839
Video & virtual tour
Property
Parking
- Total spaces: 8
- Parking features: Garage Faces Front, Oversized, Detached, Driveway
- Garage spaces: 2
- Uncovered spaces: 6
- Details: Garage Sqft: 5629
Accessibility
- Accessibility features: 2+ Access Exits, Accessible Entrance
Features
- Levels: One
- Stories: 1
- Exterior features: Extensive Hardscape, Rain Gutters
- Pool features: None
- Has view: Yes
- View description: Water, River, Scenic Vista
- Has water view: Yes
- Water view: Water,River
- Waterfront features: Rip-Rap, Shared, Private Dock Site, River
- Body of water: San Domingo Creek
- Frontage length: Water Frontage Ft: 155
Lot
- Size: 0.7 Acres
- Features: Cul-De-Sac, No Thru Street, Premium, Rip-Rapped, Stream/Creek
Details
- Additional structures: Above Grade
- Parcel number: 2102101998
- Zoning: RC
- Zoning description: Rural Conservation
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional,Ranch/Rambler
- Property subtype: Single Family Residence
Materials
- Mixed
- Foundation: Crawl Space, Slab
- Roof: Architectural Shingle
Condition
- Excellent
- New construction: No
- Year built: 1978
Utilities & green energy
- Sewer: On Site Septic
- Water: Well
- Utilities for property: Cable
Community & HOA
Community
- Security: Security System
- Subdivision: Oakwood Park
HOA
- Has HOA: Yes
- Amenities included: Boat Dock/Slip, Pier/Dock, Common Grounds
- Services included: Pier/Dock Maintenance, Other
- HOA fee: $600 annually
- HOA name: OAKWOOD ASSOCIATION OF ST MICHAELS
Location
- Region: Saint Michaels
Financial & listing details
- Price per square foot: $591/sqft
- Tax assessed value: $769,900
- Annual tax amount: $7,046
- Date on market: 11/16/2025
- Listing agreement: Exclusive Right To Sell
- Inclusions: All Appliances And Mechanicals Currently On Site. Safe.
- Exclusions: Tori Lantern Statue In Backyard
- Ownership: Fee Simple
- Road surface type: Black Top
Estimated market value
$1,594,800
$1.52M - $1.67M
$3,784/mo
Price history
| Date | Event | Price |
|---|---|---|
| 4/18/2026 | Price change | $1,679,000-8%$591/sqft |
Source:  Bright MLS #MDTA2012326 Report a problem | ||
| 2/22/2026 | Price change | $1,825,000-3.9%$643/sqft |
Source: Bright MLS #MDTA2012326 Report a problem | ||
| 11/17/2025 | Listed for sale | $1,900,000$669/sqft |
Source: Bright MLS #MDTA2012326 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $769,900 +5.2% |
| 2024 | $6,611 +11.3% | $732,067 +5.4% |
| 2023 | $5,938 +13.9% | $694,233 +5.8% |
| 2022 | $5,212 +8.3% | $656,400 +2.2% |
| 2021 | $4,812 +2.3% | $642,233 +2.3% |
| 2020 | $4,705 +2.3% | $628,067 +2.3% |
| 2019 | $4,599 +4.3% | $613,900 |
| 2018 | $4,408 +5.2% | $613,900 |
| 2017 | $4,192 +62.3% | $613,900 -3.7% |
| 2016 | $2,583 | $637,600 |
| 2015 | $2,583 +9.5% | $637,600 |
| 2014 | $2,359 | $637,600 -12.7% |
| 2013 | -- | $730,300 |
| 2012 | -- | $730,300 |
| 2011 | -- | $730,300 -13.3% |
| 2010 | -- | $842,360 +7.9% |
| 2009 | -- | $780,486 +8.6% |
| 2008 | -- | $718,613 +9.4% |
| 2007 | -- | $656,740 +8.9% |
| 2006 | -- | $603,192 +9.7% |
| 2005 | -- | $549,646 +10.8% |
| 2004 | -- | $496,100 +11% |
| 2003 | -- | $446,966 +12.4% |
| 2002 | -- | $397,833 +14.1% |
| 2001 | -- | $348,700 |
Find assessor info on the county website
Monthly payment
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Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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Climate risks
Neighborhood: 21663
Nearby schools
GreatSchools rating
- 5/10St. Michaels Elementary SchoolGrades: PK-5Distance: 1.1 mi
- 5/10St. Michaels Middle/High SchoolGrades: 6-12Distance: 1 mi
Schools provided by the listing agent
- Elementary: St. Michaels
- Middle: St. Michaels
- High: St. Michaels
- District: Talbot County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Maryland
- Talbot County
- Saint Michaels
- 21663
- 24390 Oakwood Park Rd
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