$1,066,873Average Value$406Average Price per Sq Ft16Homes For Sale
Saint Michaels is a lively Eastern Shore waterfront community
Saint Michaels retains much of its historic charm from its origins as a 17th-century Eastern Shore seaport and still draws visitors from around the region to its landmarks and cruises on Miles River. Buyers can search for historic homes that are steps away from public marinas and local establishments on Talbot Street serving drinks, dinner or groceries. “It’s similar to Tilghman Island, but the price point for homes is higher in Saint Michaels,” says John McGlannan, a Talbot County resident and Realtor with Meredith Fine Properties. “It’s also better known and more established as a tourist destination, with more commercial businesses.” Popular nearby commuter areas include Easton and Salisbury, while Washington, D.C. is about two hours from town.
The Saint Michaels shoreline features marinas and quiet residential streets.
Waterfront homes in Saint Michaels offer private docks and sweeping views of the Miles River.
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Trails, boating and the Chesapeake Bay Maritime Museum
Saint Michaels Nature Trail is a paved mile-long path through San Domingo Tidal Creek, popular for a walk or bike ride. Clint S. Bradley Park is connected to the trail and features a playground, gazebo and picnic tables. Boating is popular around the area, and residents can dock their vessels at Saint Michaels Public Boat Ramp in the harbor. The Chesapeake Bay Maritime Museum hosts exhibits and artifacts detailing the community’s history in fishing and crabbing.
Bill Shook Memorial Bridge offers a scenic crossing for walkers and cyclists in town.
The harbor in Saint Michaels is a popular spot for boating and water recreation.
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Historic single-family homes and waterfront options
Buyers can find Cape Cods, ramblers, Colonial Revivals and coastal cottages along quiet village streets. Some properties in the historic downtown district date back to the 18th and 19th centuries, when the town was a prominent shipbuilding hub in the region. Single-family homes are priced between $500,000 and $2.5 million, varying by location, square footage and age; waterfront homes typically fetch the highest prices and start around $1 million. Potential homebuyers should be advised that the community has a major flood risk due to storm surges, and many residents opt to buy flood insurance.
Saint Michaels features stately Colonial homes set among tall pines and quiet streets.
A Craftsman-inspired waterfront home offers sweeping views of the Miles River in Saint Michaels.
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Saint Michaels history and landmarks
Due to its unique history and ornate, centuries-old architecture, the town has become a popular destination for visitors around the region. During the War of 1812, British ships sought to attack the town’s shipyards during a nighttime raid. The attack did minimal damage to the community, as locals had dimmed their lights and set lanterns in the trees away from town, giving Saint Michaels the nickname “the town that fooled the British.” History buffs can take walking tours downtown to see landmarks like the Cannonball House, a Federal-style home that was hit with British cannon fire. The Maritime Museum offers Patriot Cruises, a historical tour along the Miles River.
Talbot Street hosts markets and eateries
Talbot Street is the main commercial strip in Saint Michaels. Locals can grab groceries from the Village Shoppe or order pub grub and draft beer from the Talbot Street Tavern. There are also several spots to sample local vintages , from St. Michaels Winery and Bordeleau Winery to Ava’s Pizzeria & Wine Bar, a regional chain. Patrons can also enjoy a seafood dinner with waterfront views at establishments like The Crab Claw in the harbor. Over in Easton are retailers like Walmart and Lowe’s, as well as chain grocery stores like Giant and Weis Markets.
The Crab Claw serves seafood with waterfront views in Saint Michaels harbor.
Nearby Easton features big-box stores such as Walmart and chain grocery markets.
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After school programs with Saint Michaels Middle High
Talbot County Public Schools is the main district serving Saint Michaels. Students can attend Saint Michaels Elementary School and Saint Michaels Middle High School, which both have B-ratings from Niche and are both on the same campus. The Maritime Museum collaborates with Saint Michaels Middle High School with Rising Tide, an after-school program that teaches kids woodworking skills and educates them about the ecology of the Chesapeake Bay Watershed.
Saint Michaels Middle High is one of two public high schools in Talbot County, along with Easton High.
Saint Michaels Middle High’s Saints compete in MPSSAA baseball and in 2025 made it to the 1A Championship game.
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Commuters can reach Easton, Salisbury or D.C.
Easton is a 10-mile drive east of Saint Michaels along Talbot Street, which takes around twenty minutes. “It gets more from tourism than from fishing and crabbing, but there are workboats out of Saint Michaels,” McGlannan says of the local economy. “As far as commuting, there’s more jobs in Easton, especially because it’s a bigger town.” Easton is also home to Memorial Hospital, the nearest medical center. Salisbury is a 57-mile drive east, which takes a little over an hour, and the city is the site of Salisbury Regional Airport. The nation’s capital is 80 miles away, or about a two-hour drive, depending on traffic.
Easton offers more job opportunities and sits just 10 miles east of Saint Michaels.
The nation’s capital sits 80 miles west of Saint Michaels, about two hours by car.
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Written By
Maxwell Olarinde
Photography Contributed By
Jesse Son
Video By
Tyler Newbold
Interested in learning more about homes in this area?
Reach out to
Charlotte Savoy,
an experienced agent in this area.
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On average, homes in Saint Michaels, MD sell after 69 days on the market compared to the national average of 53 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $795,000, up 21% from the median home sale price over the previous 12 months.
This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhanced with numerous upgrades. The owners added luxury vinyl plank flooring to the second level, Hunter Douglas plantation shutters with independent top and bottom operation, recessed lighting upstairs, and a high-end full-size Electrolux washer and dryer. Additional features include a smart home system with
Back Creek Landing home for sale in St. Michaels, MD — located in one of the town’s most desirable neighborhoods, known for its peaceful setting, friendly community, and proximity to downtown St. Michaels. This home is just minutes away by bike or golf cart, offering easy access to shops, restaurants, the harbor, and waterfront activities while still feeling private and serene. This beautifully
Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining
Wonderful opportunity to live in the quaint, picturesque and historic town of St Michaels at a great price. New carpeting, and new paint. Move in ready. Well kept, light filled townhouse with 2 bedrooms, one bath and fenced back yard. Must be primary residence. 2 assigned parking spaces. Walkable to all St Michaels has to offer.
Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a
Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the home’s warm, inviting feel. The upper-level living area features shining hardwood floors, and the home has been recently
Custom-built in 2019, this home masterfully blends the charm of a historic replica with today’s modern conveniences. Ideally located just a short walk from shops, restaurants, the historic St. Michaels Harbor, and the Chesapeake Bay Maritime Museum, it offers the perfect balance of comfort and lifestyle. Inside, the home features an inviting open-concept living, family, and dining area enhanced
Great location!! First floor primary bedroom! Plus 3 additional bedrooms and a full bath upstairs. Walk to town, trail, schools and pool! Breezy front porch and rear deck, large family room with fireplace for cozy nights. Lawn maintenance included !! pets on case by case. Credit report and references required.
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