$1,071,505Average Value$434Average Price per Sq Ft36Homes 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
Christopher Clinton,
an experienced agent in this area.
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On average, homes in Saint Michaels, MD sell after 82 days on the market compared to the national average of 55 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $785,000, down 1% from the median home sale price over the previous 12 months.
Extraordinary waterfront living on 3.4 acres, just one mile from historic St. Michaels. Impeccably maintained and extensively renovated, this exceptional one-level home combines relaxed comfort with top-of-the-line luxury and lives like a private boutique resort. Offered completely turnkey—furnishings, linens, fully equipped kitchen and everything shown in the photographs conveys. Enjoy
Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive
Nestled in the serene enclave of Bozman, on Harris Creek this exquisite 1940s style bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers along with fantastic sunset views and a sheltered cove. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed
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,
NEW PRICE!! 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
All resonable offers considered! Move in ready! Meticulously maintained 2 bedroom, 2.5 bath townhome offers comfort, privacy, and inviting living spaces throughout. The galley kitchen features a charming breakfast nook and flows into the dining and living area, highlighted by a wood-burning fireplace. Just beyond, a cozy sitting area opens to a brick patio overlooking a lovely backyard bordered
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.
Extraordinary waterfront living on 3.4 acres, just one mile from historic St. Michaels. Impeccably maintained and extensively renovated, this exceptional one-level home combines relaxed comfort with top-of-the-line luxury and lives like a private boutique resort. Offered completely turnkey—furnishings, linens, fully equipped kitchen and everything shown in the photographs conveys. Enjoy
Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout and plenty of potential for its next owner. The main level features beautiful hardwood floors, a galley kitchen, a separate dining room, and comfortable living spaces. Outside, you'll find a spacious yard with a storage shed, providing plenty of room for outdoor activities, gardening, or future
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.
Beautifully upgraded and thoughtfully designed, this home showcases designer‑selected wallpapers, custom finishes, and every modern convenience. The gourmet kitchen features quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling.Offering 4 bedrooms and 2.5 baths,
Embrace the quintessential Saint Michaels lifestyle in this beautifully renovated Classic Tidewater Cottage, ideally positioned in the heart of one of Maryland’s most beloved waterfront towns. Stroll to local restaurants, boutique shops, galleries, marinas, and the scenic harbor, then return home to relax on the porch or gather in the rear garden for effortless outdoor
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.
St. Michaels Cape. First floor offers living room with fireplace, dining area/kitchen combo, 2 bedrooms and bath. 2nd floor features 2 bedrooms and bath. Rear deck overlooking private backyard. Storage shed. Walking distance to downtown amenities, shopping and restaurants. Rented unfurnished. No pets. Non-smokers. Credit check and references required. One year + lease. Immediate occupancy.
***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze
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.
For rent is the upper floor apartment in a 2-apartment building in the Historic District of St. Michaels. Apartment is bright with high ceilings, wood flooring, 2 bedrooms, 1 bath, spacious modern kitchen and an attractive upper deck oriented to the back yard. Off street parking. Pets are strictly case by case. 12 months lease. Good credit and references required.
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
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.
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