Saint Michaels, MD Homes for Sale with Pool

Welcome to Saint Micheals Retreat, an extraordinary 6+/- acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and Miles River. Just moments to downtown Saint Michaels, fine dining, shopping, and entertainment, this stunning makeover offers 4,100 +/- sq. ft. of single-story living designed for endless indoor/outdoor entertainment. This

Craig Linthicum Benson & Mangold, LLC

Just 4.9-miles outside historic St. Michaels, MD...Classic "Eastern Shore Waterfront Retreat," featuring a substantial 5,400+ sq. ft. home, thoughtfully designed to capture cooling SW summer breezes and spectacular sunset views across the sparkling waters of Harris Creek. Sited on 8.26 private acres w/over 300' of natural "living Shoreline," features of the brick home include high ceilings

Tom Crouch Benson & Mangold, LLC

Welcome to this exceptional waterfront retreat on 3.5 acres overlooking Solitude Creek in Royal Oak. From the moment you enter, expansive water views set the tone for gracious living. Renovated in 2023 and thoughtfully decorated by Bountiful Home in Easton, this 3,248 sq. ft. residence offers 4 bedrooms and 3.5 baths, including a main-level waterside primary suite with spa-like bath. The gourmet

Laura Carney TTR Sotheby's International Realty

Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

Robert G. Shannahan Shoreline Realty

NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green,

Doc Keane Washington Fine Properties, LLC

Coastal charm meets small-town living in this beautifully updated cottage, just one block from the Historic District and 1.5 blocks from water access, including a marina and boat ramp, and downtown Saint Michaels! This home exudes a true vacation vibe, offering main-level living with sun-filled spaces designed for relaxation. The completely remodeled full bathroom adds modern comfort, while the

Jennifer Chino Compass

***NEW PRICE IMPROVEMENT..... MUST SEE THIS Charming 4-Bedroom Home with Guest Cottage in Saint Michaels, MDHome was under contract with a lovely couple trying to move their family to St. Michaels. WE GET IT- It's a Great place to live. Unfortunately, after waiting, and waiting and giving multiple extensions because the seller understood they really loved this home-- They just could not

Cheri Bruce-Phipps TTR Sotheby's International Realty