$1,041,634Average Value$410Average Price per Sq Ft39Homes 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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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.
1/2
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
Larry Brennan,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
On average, homes in Saint Michaels, MD sell after 78 days on the market compared to the national average of 56 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $785,000, up 14% from the median home sale price over the previous 12 months.
Priced to sell! The perfect weekend getaway does exist—and it's more attainable than you might think. Escape the city and discover the charm of St. Michaels, one of the Eastern Shore's most beloved waterfront towns. Known for its picturesque streets, waterfront dining, boutique shopping, wineries, marinas, and laid-back coastal lifestyle, St. Michaels offers the perfect place to relax, recharge,
Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‐glass entry door and
Want to live close to Historic Saint Michaels in a beautiful and low maintenance setting offering ample first floor living? Welcome to 24375 Widgeon Place, Unit 37, nestled in the picturesque Martingham Community just outside Historic St. Michaels . This desirable END UNIT property is the epitome of style and comfort, encapsulating all the charms of eastern shore coastal living. Featuring 3
PRICE REDUCED: 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
Priced to sell! The perfect weekend getaway does exist—and it's more attainable than you might think. Escape the city and discover the charm of St. Michaels, one of the Eastern Shore's most beloved waterfront towns. Known for its picturesque streets, waterfront dining, boutique shopping, wineries, marinas, and laid-back coastal lifestyle, St. Michaels offers the perfect place to relax, recharge,
Escape to the sought-after Swan Road Villa Townhomes, where low-maintenance living meets comfort, convenience, and lifestyle. This bright and inviting reverse-living townhome offers 2 bedrooms, 2.5 baths, and a thoughtfully designed floor plan that appeals to both full-time residents and weekend retreat seekers alike. The upper level serves as the heart of the home, featuring an open-concept
Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled
Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring
Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached
This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area
Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application
Cornelia HeckenbachLong & Foster Real Estate, Inc.
RDesirable Rio Vista Duplex – Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with
Cornelia HeckenbachLong & Foster Real Estate, Inc.
Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style
Cornelia HeckenbachLong & Foster Real Estate, Inc.
Tucked into the heart of Back Creek Landing, this home offers the kind of layout and setting that just works—comfortable, well thought out, and connected to both nature and town. The main living space is designed around how people actually live. The kitchen is open and inviting, with a bright eat-in area and an elevated counter with seating—perfect for morning coffee, casual meals, or simply
Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides
GREAT RENTAL OPPORTUNITY !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
Cornelia HeckenbachLong & Foster Real Estate, Inc.
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.
Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‐level home offers both convenience and a peaceful, private setting. Sitting on nearly a quarter acre, the property features a fully fenced
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.
Beautiful modern 2 bedroom townhouse in Martingham completely renovated with bedrooms on the first floor with incredible tile bath. Open floor plan is bathed in natural light. Pets are case by case.
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
