$1,058,821Average Value$413Average Price per Sq Ft28Homes 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
Nicole Schreibstein Abbott,
an experienced agent in this area.
GreatSchools:
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On average, homes in Saint Michaels, MD sell after 70 days on the market compared to the national average of 54 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $795,000, up 16% from the median home sale price over the previous 12 months.
OPEN HOUSE Sat 2/28 1-3pm. 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
Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and
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
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
Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a
Welcome to 24345 Widgeon Place #25, a premier end-unit townhome in the waterfront community of Martingham, located just a mile from historic St. Michaels and adjacent to the Inn at Perry Cabin Links golf course. This light-filled home features three bedrooms and three full baths, including a rare first-floor bedroom with an ensuite. The open-concept main level offers hardwood floors, a
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
OPEN HOUSE Sat 2/28 1-3pm. 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
DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HELP PAYING FOR YOUR MORTGAGE. THESE DUPLEXES RARELY BECOME AVAILABLE.The duplex is located in a water access community with dock access through the owner's approved application and payment.The building consists of two units with mirrored floor plans. They offer a kitchen with small eating area, an open
Cornelia HeckenbachLong & Foster Real Estate, Inc.
DESIREABLE RIO VISTA LIVING -MOVE IN ONE SIDE OF THIS DUPLEX AND RENT THE OTHER ONE TO HELP PAYING FOR YOUR MORTGAGE. THESE DUPLEXES RARELY BECOME AVAILABLE. The duplex is located in a water access community with dock access through the owner's approved application and payment. The building consists of two units with mirrored floor plans. They offer a kitchen with small eating area, an open
Cornelia HeckenbachLong & Foster Real Estate, Inc.
UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL .ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL
Cornelia HeckenbachLong & Foster Real Estate, Inc.
Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe.Time to make your personal selections. Make this home your personal statement.Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more.Make this
Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and
The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not
One of the few remaining building lots in the St. Michaels area. This is a prime building lot, 75' x 150', ready for someone to design and construct a new home. Public water/sewer and high-speed internet available for hookup. Calvert Avenue is a convenient address, near schools, banks, grocery stores, boat ramps and St. Michaels' many fine shops, museums and restaurants. A public waterfront park
Great Martingham 2 bedroom townhouse available immediately. Great outdoor spaces with generous open floor plan. Some furniture included if wanted. Two en-suite bedrooms. Pets case by case.
WATERFRONT YEARLY RENTAL – Historic St. Michaels Maryland. This Harbor Front Home is within walking or biking distance to all that St. Michaels has to offer. WATERFRONT VIEWS for most rooms including the HUGE GLASSED EASTERN SHORE ROOM - Single Floor living . $ 3,500 per month/1year lease min., INCLUDES BOAT SLIP with 4 ft. mlw., grass cutting, water and sewer. Take the next step and secure a
This home is just around the corner from all the best of St. Michaels. Situated on a corner lot offering a small fenced-in back yard, this historic home features all the amenities of modern living. With 2 bedrooms, 2 baths and a loft style space on the 2nd floor and an open living/dining room area on the first level, plus a eat-in kitchen an half bath, this home offers plenty of room for all. The
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.
Golf Course Town House in beautiful St. Michaels. Enjoy watching golfers just out your back slider. Renovated unit 2 bedroom, 2.5 bath unit, gas fireplace, balcony, and 1-car garage. Located in the beautiful Martingham Circle, with community pool, golf, tennis, restaurants, and a beautiful waterfront community.
RARE Chesapeake Bay beach side rental with 2 BDR, 2BTH guest house on 2+ Acres. You can enjoy the salt air and fabulous sunsets in any season! Furnished and ready for occupancy.
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