528 properties for sale in Saint Michaels, St Michaels town District 2 St Michaels Talbot County Maryland

Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated designer wallpaper accents throughout this stunning model home! Offering 4 bedrooms and 2.5 baths, the home includes a firstfloor primary suite with an ensuite spa bath, custom shower, and generous walkin closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, youll enjoy easy access to charming shops, restaurants, waterfront activities, and yearround festivals

Just reduced to $525,000affordable, turn-key easy living near the water in St. Michaels. Located 1.5 blocks from public boat ramps and marina access, this updated coastal getaway delivers effortless weekend living without Historic District restrictions. Major recent capital investmentsa new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windowsmean zero weekend project lists. Spend your Saturdays lounging by your private in-ground pool, hosting at the beach bar with cable TV, or storing kayaks and gear in the detached garage. Convenient main-level living just steps from downtown dining, coffee shops, and harbor parks. Perfect as a low-maintenance weekend retreat or primary escape from Day 1

This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the'Keithley House, the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1- time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot

Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside'River Room. The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crab

This property has been gutted and the floor joists replaced, new Advantac subfloor installed, drywall removed, new interior framing, new roof, insulation, new electric and a new sewer line to the street. The hard work has been done. It's ready for you to make it your own. Off street parking and large rear yard. Please be careful showing as there is still building materials on the property

The charm of historic St Michaels comes to life in this 1890 home, completely updated for modern comfort and amenities. Each room is defined yet open, flowing into each other with ease. The dining room opens to the living space and sitting room with gas fireplace. Exposed beams and cathedral ceilings provide interest in design and skylights provide brightness and light. The beautiful, gourmet kitchen (updated recently) has quartz countertops and a breakfast nook overlooking the backyard patio and gardens. Both en suite full baths are updated and wait until you see the thoughtfully placed half bath tucked under the staircase in the foyer entry hall. Just one of the many details found throughout the home. There are multiple opportunities to take advantage of outdoor living with a light-filled sun room and screened porch leading to a spacious brick patio. The masterfully designed gardens surrounding the home provide privacy, peace and tranquility as well as a tapestry of color during the

Whether you are looking for a full-time residence, weekend retreat, or investment property, this unit is truly move-in ready. Situated in Martingham community just minutes from St. Michaels, shops, restaurants and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship, energy efficiency, and long-term durability. The redesigned open floor plan creates a seamless flow throughout the main living areas, complemented by updated cabinetry, granite countertops, and stainless steel appliances in the kitchen. All three bathrooms have been refreshed with new vanities, fixtures, and finishes, offering a clean and modern feel throughout the home. Beyond the cosmetic updates, extensive infrastructure improvements provide peace of mind, including a newer HVAC, upgraded electrical panel, full outlet and switch replacement and enhanced attic efficiency with resealing and R49 in

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 and well-appointed kitchen, featuring a gas stove and stainless steel appliances. Practical amenities include a mudroom with laundry just off the attached two-car garage, a Rinnai tankless water heater, and an efficient dual-zone heat pump system with separate upstairs and downstairs climate controls. The second floor offers additional flexibility with a bedroom, full bathroom, and a large family roomperfect for guests, a home office, media room, or recreation space. Just off the recreation room, a spacious attic provides abundant storage and offers potential for future expansion. Outside, enjoy

Big reduction. Great value do not miss out! Charming Coastal Retreat with Endless Potential in Backcreek LandingWelcome to this beautiful two-story home in the highly sought-after Backcreek Landing neighborhood, just minutes from historic St. Michaels. Blending coastal elegance with incredible value, this property features a brand-new roof with lifetime shingles and is attractively priced, leaving you budget flexibility to update the bathrooms to your taste. From the front porch, you can enjoy serene views of the pond right across the street and step directly onto the neighborhood walking trail. The main level offers a private front office, a formal dining room, and a grand living room with dramatic cathedral ceilings and French doors leading to a spacious deck. The casual dining area opens through separate French doors to a wonderful screened porch, creating a seamless flow for indoor-outdoor living. Your main-floor primary suite serves as a private sanctuary, complete with tray ceili

Beautifully restored Historic Victorian in the heart of Saint Michaels. From the wide, welcoming front porch to the gated, manicured yardcomplete with a hammock ideal for long afternoon napsevery space is designed for comfort and relaxation. A brick walkway leads to the custom beveledglass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marbletile full bath. The private thirdfloor primary suite offers a peaceful retreat with its own ensuite bath. Seller raised the home 3 feet and the lot 2 feet to help will water run-off and has a dry encapsulated crawl space with cement f

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 chef-inspired gourmet kitchen designed for elevated entertaining and showcases premium appliances, including a 60-inch extra-large refrigerator/freezer, Wolf propane cooktop, and integrated refrigerated and freezer beverage drawers thoughtfully integrated into the cabinetry. The first-floor primary suite provides effortless main-level living with a private enclosed porch and spa-like bath retreat. This combined property conveys two deep-water boat slips (6' MLW) with water and electricity, each able to accommodate a 40-foot vessel. Community amenities include kayak launch; tennis courts lined for pickle

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 a cozy eating area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath Whether you're looking for an owner-occupied investment property or a fully leased income-producing asset, this duplex presents excellent potential. These units have a strong rental history and are consistently in demand. Both units are currently tenant-occupied. THIS IS WHY WE DO NOT HAVE INTERIOR PICTURES For investors seeking additional opportunities, the neighboring building at 1211 Rio Vista is also available for purchase (MLS #MDTA2012-). Educed. Reduced. Do not wai

Nestled in the serene enclave of Gull Wing Villas, this exquisite bungalow-style townhouse offers a harmonious blend of comfort and relaxation. Step inside to discover an inviting open floor plan that seamlessly combines the dining and living areas, perfect for both relaxation and entertaining. The warmth of wood floors and the charm of a brick gas fireplace create an ambiance that feels like home. This residence features two spacious bedrooms, including a primary suite with a luxurious walk-in shower and ample closet space. Recessed lighting and ceiling fans enhance the inviting atmosphere, while the eat-in kitchen beckons culinary creativity. An attic provides additional storage, ensuring that every inch of this home is utilized efficiently. Outside, indulge in the exclusive lifestyle that comes with private for residents only access to the Miles River. Enjoy leisurely afternoons at the waterfront park or embark on adventures with your canoe or kayak, enjoy the picnic area to end the

Located in Bentley Hay and within walking distance of Historic St. Michaels, this charming cottage would make an exceptional pied-terre. Enjoy two bedrooms and two bathrooms on separate levels, with tremendous privacy and rear alley access. Easy access to nearby parks is perfect for leisurely strolls. Convenient public services and amenities are just a stone's throw away, making daily errands a breeze. Whether you're exploring local shops or enjoying a meal nearby, you'll find everything you need within reach

Enjoy the charm of St. Michaels from this end-unit townhome in Martingham. Offering three bedrooms and two full baths, the home features a flexible layout with a first-floor bedroom and full bathwell suited for guests, a home office, or convenient main-level living. The renovated kitchen has white cabinetry and stone countertops, with a glass door opening to a bright, tile-floored sunroom. A fireplace and large picture frame window make the living room a welcoming place to unwind. Upstairs, the primary bedroom opens to a private deck with a small water view and peaceful views of landscaped grounds. An attached one-car garage adds everyday convenience. Martingham is home to the Links at Perry Cabin, a scenic 18-hole championship course designed by Pete Dye, while the nearby town of St. Michaels offers the historic character, local shops, waterfront outings, and dining that make it such a special place to spend time

Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butlers pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows natur

Embrace the Eastern Shore lifestyle in this private mini retreat, located just minutes outside of historic St. Michaels. Tucked away behind a natural buffer of mature trees and surrounded by beautiful waterfront estates, this property offers peace and privacy. For the outdoor or hobby enthusiast, the property features a versatile 4-stall barn with ample space to store cars, mowers, or your boat. The acreage currently showcases a lush, natural landscape, but offers the perfect canvas to easily revive the past pastures for equestrian or agricultural use. Inside, the home features classic hardwood floors throughout the first level, while the upstairs bedrooms and hallway are finished with carpeting. Ready for your personal touch, the home is being sold as-is and includes an existing flueperfect for hooking up a cozy wood or gas stove. Outside, a private vinyl pool (last serviced and fully operational when closed in October 2023) awaits summer refreshment. Rest easy knowing the core compon

Timeless Waterfront Luxury in San Domingo Cove. Set along the tranquil waters of San Domingo Creek, this exceptional custom waterfront residence delivers a refined coastal lifestyle defined by striking architecture, exceptional craftsmanship, and effortless indoor-outdoor living. From the moment you enter, soaring two-story ceilings, a dramatic family room with gas fireplace, walls of glass, and a beautifully detailed open staircase with stainless-steel cable railings create an impressive sense of volume and light. A second-story catwalk and loft overlook the main living spaces, while expansive windows draw the eye beyond the pool to serene broad water views with amazing sunsets. Designed with both sophisticated entertaining and comfortable everyday living in mind, the chef's kitchen is beautifully appointed with quartz countertops, stainless-steel appliances, extensive soft-close cabinetry, a pot filler over the commercial range, a built Keurig in the refrigerator, and an oversized is

Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light and offers an open floor plan with a comfortable living room, dining area and brand new beautifully updated kitchen featuring white cabinetry and new appliances. Beautiful wood floors throughout. The home offers four bedrooms and three and a half baths, with the added convenience of stacked washer and dryer setups on both levels. Large family room overlooking rear yard with wood burning brick fireplace with outside access to pool. First and second floor primary suites with custom tile bathrooms. Off street parking with no rental restrictions and no town taxes. Close to YMCA, school, restaurants

A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Codstyle home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual needs, all while maintaining privacy and a connection to the surrounding natural landscape. Restaurants, shops, seasonal events, waterfront parks, and the charm of the historic district are all close at hand, yet the property feels quietly removed. Approximately three times the size of a typical in-town lot, the parcel allows for thoughtful home placement, outdoor living areas, and driveway access from Miles Avenue, Canton Street, or both, depending on the final plan. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer

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 home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised valuean outstanding opportunity!

Charming Cape Cod in the Heart of St. Michaels Welcome to this beautifully maintained Cape Cod in the heart of St. Michaels, where newer construction, timeless charm, and exceptional indoor-outdoor living come together in a truly special property. Built in 2019, this inviting home features three generously sized bedrooms, two full bathrooms, and one half bath, with beautiful hardwood flooring throughout. Meticulously maintained and move-in ready, the home offers the comfort and quality of a newer home with the character and warmth of a classic Cape Cod. The outdoor living space is truly exceptional. Step onto the large deck, perfect for entertaining family and friends, and enjoy a private backyard that backs to peaceful woods. Gather around the fire pit, relax with a drink at your own tiki bar, or simply enjoy the tranquility of the wooded setting. It's an ideal space for summer entertaining, weekend gatherings, or quiet evenings at home. And then there's the location. Situated within

Come see a true Eastern Shore gem, set on 20 peaceful waterfront acres along Edge Creek. This beautifully renovated 4-bedroom, 4-bathroom home features all the hallmarks of a coastal getaway while providing modern, functional conveniences. Walk through the front door, and youre met with direct water views that can be seen from virtually every room in the home. Youll also find natural light that fills every space due to the ample window and sliding glass door installations, coupled with southwestern exposure off the back of the home. Make your way over to the well-appointed, fully renovated kitchen featuring Miele appliances. Around the corner is a first-floor primary suite with direct waterfront views, his-and-hers sink vanities, a spacious walk-in closet system with built-ins, and one of the homes three fireplaces. Upstairs, youll find plenty of space for guests, including a bedroom featuring built-in bunks. On the third floor is a bonus loft area with twin walkout balconies. Across t

Discover a prime investment opportunity in the desirable St. Michaels community. This 3-bedroom, 2-bathroom ranch-style home, built in 1960, boasts a spacious 1,340 sq. Ft. of potential. With its classic vinyl siding, this property is ready for some TLA and future enhancements. The roof is less than 5 years old and layout offers flexibility, making it easy to adapt the space. The 0.17-acre lot provides ample outdoor space for potential landscaping or recreational activities, enhancing the property's appeal. Homeowners or Investors will appreciate the potential to transform this property into your personal residence or investment property. Being sold As Is condition

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 one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank