$1,042,630Average Value$419Average Price per Sq Ft45Homes 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
Tracy Higgs-Wagner,
an experienced agent in this area.
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On average, homes in Saint Michaels, MD sell after 79 days on the market compared to the national average of 58 days. The median sale price for homes in Saint Michaels, MD over the last 12 months is $757,500, up 2% from the median home sale price over the previous 12 months.
PUBLIC OPEN HOUSE: SUNDAY, JUNE 7 from 10AM-12:30PM. 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
Charming yet completely reimagined, this beautifully remodeled home offers refined Eastern Shore living at its best. Set on beautifully landscaped grounds featuring lovely water views and a partially fenced rear yard with paver patio. Thoughtfully designed and updated the main level features a modern kitchen with newer appliances, cozy breakfast room, living room with fireplace, formal dining
Situated on a corner lot just minutes from downtown St. Michaels, this 3-bedroom, 2-bath home offers easy access to local shops, restaurants, and the Maritime Museum. Inside, the living room is filled with natural light from a large bay window and features LVP flooring, recessed lighting, and updated fixtures throughout. The kitchen and dining area provide an open, functional layout with direct
Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub,
Escape to Swan Road Villa Townhomes — a bright, low-maintenance retreat. This reverse-living 2‐bedroom, 2.5‐bath townhome features an open floor plan on the second level with a galley kitchen, dining area, and a combined living room that opens to a balcony spanning the entire back of the second floor — perfect for indoor/outdoor living and filled with natural light. The main level includes two
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
The perfect weekend getaway does exist — and it’s affordable. Escape the city / suburbs and spend your weekends in the quintessential Eastern Shore town of St. Michaels, known for its picturesque streets, quaint shops, vibrant dining scene, wineries, and distilleries. This charming waterfront community has everything you need to relax, recharge, and truly enjoy life on Maryland’s Eastern Shore -
New Price! Transformative renovation in Martingham! This beautifully updated 2-bedroom, 2-bath single-level Gull Wing Villa overlooks the 6th fairway at Links at Perry Cabin, offering a serene golf course setting just minutes from the heart of St. Michaels. Thoughtfully redesigned, the home features new flooring throughout, a fully renovated kitchen and baths, and a reimagined layout that
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
JUST REDUCED - DONT WAIT TO LOOK AT THIS 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
Cornelia HeckenbachLong & Foster Real Estate, Inc.
REDUCED - REDUCED - DO NOT WAIT TO SEE THIS 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
Cornelia HeckenbachLong & Foster Real Estate, Inc.
RIO VISTA COMMUNITY - NO TOWN TAX - WATER FRONT PARK AT THE MILES RIVER FOR RESIDENTS ONLY.GREAT NEIGHBORHOOD RIGHT OUTSIDE OF THE BUZZING HISTORIC ST MICHAELS , GROCERY STORE , HARDWARE STORE, RESTAURANTS, BEAUTY SALON, PILATES ,YMCA , GARDEN CENTER - ALL IS JUST AROUND THE CORNER PRACTICALLY.THE HOME IS CURRENTLY RENTED, 24 HOURS SHOWING APPOINTMENT IS NEEDED.HARDWOOD FLOORS, WOOD
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
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.
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.
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
Neat and tidy, tiny cottage that's perfect for one person located a short walk to the Claiborne Public Landing.The owner will share the use of the yard and tenant is welcome to bring a lawn chair.Owner pays for water, sewer, trash pickup and lawn maintenance.Located a short walk from Claiborne Beach and Public Landing.There is a rental application fee. The applicant should have a
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