Dappled in shade along the tranquil shores of San Domingo Creek, this picturesque Oakwood Park cottage is a serene waters-edge haven blending refined renewal with carefree charm. Originally constructed in 1952 and reimagined from its frame in 2024, the home's tailored Eastern Shore character boasts 836 square feet of soft hues, wide-planked floors, and finishes of delightful simplicity. Within, waters-edge views inspire slow mornings and quiet evenings while your kitchen keeps favorite local wines and preps crab feasts, picnics, and oysters gathered from your private pier. Under the trees, .31 acres of curated low-maintenance landscaping provides an atmosphere of ease as stone lined paths, hydrangeas, mature trees, and greenspace gently slopes into protected rip-rapped shore. Here, launch morning kayak floats, share evening stories 'round the firepit, or doze in the hammock. Two bedrooms and a sophisticated bath refresh after a day on the Bay, while the powered ADU extends the home's potential for a creative studio, workshop, or staging spot for adventure gear. Fully furnished and income producing, the property is a successful turn-key vacation rental with added potential due to the arrival of public sewer and rare opportunity to purchase the adjoining cottage for an exclusive waterfront enclave. From this adorable home base, slow coastal rhythms continue just a bike-ride's-distance from historic St. Michaels; where dining, boutique shops, and the magic of Chesapeake life awaits.