Saint Michaels MD Real Estate & Homes for Sale

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 walking distance of downtown St. Michaels, you can easily leave the car behind and enjoy the town's wonderful restaurants, shops, waterfront, and attractions. Few properties offer this combination of privacy and convenient in-town living. Inside, the home offers spacious bedrooms, three bathrooms, hardwood floors, and the peace of mind that comes with a 2019 build. Whether you're looking for a full-time residence, weekend retreat, or Eastern Shore getaway, this home offers an exceptional opportunity to enjoy the St. Michaels lifestyle. Property Highlights Built in 2019 3 large bedrooms 2 full bathrooms + 1 half bath Beautiful hardwood flooring throughout Beautifully maintained and move-in ready Large deck designed for entertaining Private backyard backing to woods Outdoor tiki bar Fire pit Excellent indoor-outdoor entertaining space Walk to downtown St. Michaels Close to restaurants, shops, waterfront, and attractions Rare combination of in-town convenience and private wooded setting Come discover a home where entertaining comes naturally, privacy is preserved, and the best of St. Michaels is just a short walk away. This home is also for Rent on MLS MDTA2015258

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 summertime. Included amidst the gardens a pergola for outdoor dining and a babbling stone water fountain. The entire back yard is fenced and lovely mature trees provide comfortable shade on this corner lot. Walk to town for shopping, waterfront dining and local events or get some exercise on the nearby St. Michaels Nature Trail. For your parking needs, there is a detached one car garage and three additional off-street, private parking spaces. To truly appreciate this lovingly cared-for home, it must be felt in person!

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 day, foster a sense of connection with neighbors while maintaining your privacy. With two dedicated parking spaces and a well-maintained environment, this property is not just a home; it's a lifestyle choice. Experience the tranquility of this golf community living while enjoying the conveniences of one story living amenities. Embrace the opportunity to make this comfortable retreat your own.

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 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.

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.

With extensive updating done less than three years ago, this home in the popular Martingham community shows beautifully! The spacious, open living room with hardwood floors and fireplace overlooks a pavered patio and lots of greenspace beyond. The kitchen is up to date and well designed, and a pocket door separates it from the first floor bedroom suite, which could also be a den or office. Upstairs are two generous ensuite bedrooms with updated baths. A slider off the primary bedroom leads to a porch overlooking the landscaped grounds. A one-car garage is just outside the front door, and additional parking is available just steps away. All this within a mile of historic St. Michaels (but no town taxes!).

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, grocery stores, museums, and downtown shops. A wonderful place to settle in and enjoy the lifestyle that makes St. Michaels so special.

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 ceilings, a walk-in closet, and serene views of a backyard framed by mature crepe myrtles. Upstairs, you will find a massive bonus room equipped with a water hookup, two bright guest bedrooms, a shared full bath, and a large walk-in attic. Complete with a two-car garage, this home is the perfect Maryland Eastern Shore getaway.

FALL IN LOVE WITH LIFE IN ST. MICHAELS! As summer fades, the Eastern Shore becomes even more captivating. Just one mile from vibrant downtown St. Michaels, this meticulously renovated waterfront residence offers easy access to seasonal festivals, exceptional dining, charming boutiques and year-round waterfront activities. Designed for effortless one-level living, the home combines thoughtful design and relaxed comfort in a resort-like setting. Its westerly orientation provides expansive water views, spectacular sunsets and abundant wildlife. Offered completely turnkey - furnishings, linens, fully equipped kitchen and everything shown in the photographs convey. Additional features include a saltwater pool, pool house, three-car garage and a separate, fenced tiny house for the dogs!

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 butler's 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 naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler's pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

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 first-floor primary suite with an ensuite spa bath, custom shower, and generous walk-in closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1-car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, you'll enjoy easy access to charming shops, restaurants, waterfront activities, and year-round festivals.

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 1860-1870 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 offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! Come by boat or by car. ACCESS BY APPT ONLY, surveillance cameras.

This well-maintained duplex with new roof in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions - all while benefiting from no town taxes. With both units currently 100% leased, this property provides immediate, reliable income, making it a smart addition to any investment portfolio.

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.

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/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

Just reduced to $525,000 - affordable, 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 investments - a new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windows - mean 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 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 room - perfect 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 a beautifully landscaped backyard featuring a stone patio and ample garden space, creating the perfect setting for outdoor dining, gardening, or simply enjoying the peaceful surroundings. Ideally situated in the heart of St. Michaels, this home offers exceptional proximity to the area's most beloved destinations. Located less than 200 feet from the St. Michaels Nature Trail, just 0.2 miles from Chew Street Park, and only 0.2 miles from historic downtown St. Michaels, you'll enjoy convenient access to shopping, dining, waterfront attractions, and community events. Adding to the appeal, plans are underway for the future San Domingo Creek Park at the end of W Marengo Street - a proposed 7.6-acre waterfront park focused on recreation, environmental restoration, and trail connectivity that is anticipated to become the largest waterfront park in St. Michaels. Exceptional proximity to downtown St. Michaels, future recreational amenities, modern comforts, and versatile living spaces make this home a rare opportunity in one of the Eastern Shore's most sought-after communities.

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 insulation installation. Interior finishes have been completely reimagined and updated throughout, including new luxury vinyl plank flooring on the upper level and premium Mohawk carpeting with upgraded padding in the lower bedrooms and on the stairwell (2024). Fresh interior paint throughout the home, along with meticulous restoration of original doors - stripped, primed, and repainted with all new hardware installed in 2024 - add to the home's character and detail. Additionally, the deck was also recently primed and painted. Additional improvements include a new washer and dryer (2024), new sliding glass doors in the bedrooms, and a 60-inch Hunter ceiling fan in the great room. A stand out feature of this unit is the expanded floor plan, offering a more open, functional, and spacious living area not commonly found in similar units. The HOA recently completed significant improvements, including a new roof, decking replacements, and new gutters in 2025. Completely turnkey and thoughtfully upgraded make this property ideal as a full-time residence, weekend retreat or investment property. Come and enjoy the St. Michaels lifestyle today.

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 value - an outstanding opportunity!

Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan delivers comfort and ease. High-end finishes include Shaw luxury vinyl plank flooring, a gourmet kitchen with a 48" dual-fuel range, custom tile backsplash, quartz countertops, stainless steel appliances, and a spacious walk-in pantry. The inviting living area features a fireplace and seamless access to the covered front and rear porches. The primary suite offers a true retreat with a spa-inspired ensuite bathroom, soaking tub, walk-in shower, sitting area, and a large custom closet. Additional highlights include a dedicated laundry room, public sewer, and thoughtful craftsmanship throughout. This beautifully designed home is a must-see for anyone seeking luxury living in one of Maryland's most charming waterfront towns.

PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

BACK ON THE MARKET WITH A NEW PRICE - DON'T MISS THIS EXCEPTIONAL WATERFRONT OPPORTUNITY! Tucked away in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront retreat offers a rare combination of privacy, comfort, and quintessential Eastern Shore charm - all just minutes from the heart of town. Formerly a successful vacation rental, this beautifully maintained three-bedroom brick home is designed for relaxed year-round living and effortless entertaining. The inviting open floor plan features rich wood flooring, double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views are part of everyday life here. Spend quiet mornings beneath the shade of mature trees along the shoreline, unwind in the hammock as the Chesapeake breezes drift by, or gather with friends and family for unforgettable outdoor entertaining. The expansive deck features a built-in outdoor kitchen and hot tub, while a charming stone-walled patio offers another inviting space to relax. An outdoor shower makes post-swim cleanup easy, and the private pool provides the perfect place to cool off on warm summer days. For boating enthusiasts, the property delivers exceptional waterfront amenities with a private dock offering approximately 3 feet MLW, a boat lift, and a boat launch, providing convenient access to the water. A separate two-room detached studio with a covered porch adds even more versatility - perfect for visiting guests, a home office, creative pursuits, or a private getaway - all while taking in beautiful water views. Additional features include an encapsulated crawl space and numerous thoughtful updates throughout the property. And when you're ready to explore beyond your own waterfront haven, you're just minutes from the best of St. Michaels, including acclaimed restaurants, boutique shopping, charming caf s, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. Private, picturesque, and perfectly positioned - this is a rare opportunity to experience the very best of Eastern Shore waterfront living in one of St. Michaels' most sought-after neighborhoods.

Beautifully restored Historic Victorian in the heart of Saint Michaels. 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 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 marble-tile full bath. The private third-floor primary suite offers a peaceful retreat with its own en-suite 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 floor. Just one block from the water - with water views from the street - this home captures the best of small-town living. Enjoy walking access to Saint Michaels' restaurants, quaint shops, kayaking, swimming, boating, and biking. It's a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

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 #MDTA2012942).EDUCED - REDUCED - DO NOT WAIT TO SEE THIS DESIREABLE RIO VISTA LIVING -MOVE IN ONE