St Michaels MD Real Estate & Homes for Sale

This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth of July fireworks and thirsty Thursday with your new neighbors. Less than 3 miles to downtown St. Michaels Fine Dining and Shopping. MORE PHOTOS TO COME.

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, and double vanity. Upstairs, enjoy a private balcony with elevated water views, while the rear composite deck provides the perfect setting for everyday living and entertaining, all overlooking the Miles River. The outdoor space is designed to impress, complete with hardscaped pavers, a gas-connected grill, pizza oven, and propane fire table. A private dock offers direct water access, ideal for boating, kayaking, or simply enjoying the waterfront lifestyle. Additional highlights include new LVP flooring, a new furnace, encapsulated crawlspace, and a newly installed irrigation system to maintain the home's mature landscaping and hydrangeas. A detached garage and access to a nearby community dock within walking distance further enhance the lifestyle this property offers. Tax record indicates wrong square footage, actual square footage of the home is 3,076 square feet of living space. *** Settlement cannot occur before September 10th, 2026***

Known as the William J. Wrightson House, this distinguished circa 1897 residence in the heart of St. Michaels beautifully blends timeless elegance and refined architectural detail with the comforts and conveniences of modern living. Lovingly restored from top to bottom, the home has undergone extensive renovations and improvements, including all new HVAC systems, tankless hot water system, updated wiring, crawlspace encapsulation, new roof and gutters, recessed lighting, high-end appliances, three fully renovated baths, a custom butler's pantry, complete interior and exterior painting, and new patio grading and drainage, among many others. A full list of improvements is available. Ideally situated just steps from the waterfront, marinas, boutique shops, waterfront dining, and renowned local restaurants, the property offers an exceptional in-town lifestyle in one of the Eastern Shore's most beloved waterfront communities. Filled with natural light throughout, the beautiful 3BR/3BA residence showcases heart pine and yellow pine flooring, custom millwork, and thoughtfully renovated living spaces designed for both everyday comfort and effortless entertaining. The welcoming living room, anchored by a new gas fireplace/stove, flows seamlessly into a gracious formal dining room ideal for gatherings with family and friends. The gourmet kitchen features quartz countertops, top-tier appliances, abundant cabinetry, and custom built-ins, effortlessly combining style and functionality. At the rear of the home, a stunning sunroom addition serves as a true focal point, featuring vaulted ceilings, a shiplap accent wall, wet bar and custom butler's pantry with beverage chiller and bar sink, custom built-ins, a renovated full bath, and French doors opening to the picturesque gardens and brick patio beyond. Upstairs, the comfortable primary suite offers a peaceful retreat, complemented by a luxurious bath with a clawfoot soaking tub, Carrara Bella marble flooring (in shower as well), custom antique vanity, and glass-enclosed walk-in shower. Two additional guest bedrooms and a beautifully renovated bath with marble tile flooring, granite-topped vanity, and Perrin & Rowe fixtures provide inviting accommodations for family and guests. The outdoor spaces are equally enchanting, highlighted by a stunning English garden filled with roses, crepe myrtles, and hydrangeas, all enclosed by a charming French Gothic lattice shadowbox fence, creating a private and storybook setting.

This exquisite in-town St. Michaels coastal-style waterfront is a designer's dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home's appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.

This well-maintained duplex 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.

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 enhances both flow and functionality. The kitchen now opens seamlessly to the living area - ideal for modern living and entertaining. The primary bath has been expanded and now includes a large vanity. The smart design choices resulted in the addition of a generous extra closet in the primary suite. Additional updates include a new roof (2025), providing peace of mind for years to come. Located in the desirable Martingham community, residents enjoy access to a waterfront park with beach which is only about a 15 minute walk away. All of this is just moments from St. Michaels' renowned shops, restaurants, and harbor.

FABULOUS ONE STORY LIVING WITH PRIVATE BACKYARD WITH VIEW OF THE POND OF THE 4TH GREEN OF THE LINK AT PERRY CABIN . JUST MINUTES FROM HISTORIC ST MICHAELS CENTER THE COMMUNITY IS A FAVORITE WITH ITS BEAUTIFUL WATERSIDE PARK FOR RESIDENTS ONLY OVERLOOKING THE MILES RIVER. THE HOME IS IN IMMACULATE RENOVATED CONDITION, BATHROOMS , KITCHEN, PAINT , THE ROOF WAS REPLACED IN SEPTEMBER 2025; 30 YEAR SHOINGLES. THE MAIN HVAC WAS INSTALLED IN 2021 WITH A CURRENT SERVICE AGREEMENT . NEW HOT WATER HEATER WAS INSTALLED IN 2024, THE DISWASHER WAS REPLACED IN 2024. INCLUDED IN THE SALE IS AN ELECTRIC VEHICLE CHARGER IN THE GARAGE AND AN INVISIBLE FENCE IN THE YARD.

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 room, and fabulous sunroom. The main level owner's bedroom has a recently remodeled en-suite bath. The second floor is currently set up as a guest apartment with private entrance. This apartment offers a private bedroom, full bathroom, kitchen, living room, dining area and dedicated laundry. In the yard you will find a Williamsburg Garden shed plus separate workshop which includes attic, HVAC, and running water. Parking for several vehicles. Encapsulated crawl space. Thoughtfully designed and move-in ready. This home could easily be converted back into a 3-4 bedroom house. Waterfront park only steps away.great for watching the boating activity and fireworks. Prime location close to downtown amenities, shopping, restaurants, and public water access.

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 bedrooms, two full baths, and a laundry room. Convenient access to golfing(with membership), walking and biking paths, and a waterfront park. Ideal as a first home, second home, primary residence, or investment. Recent upgrades - roof, bathrooms, flooring, HVAC unit, and interior painting.

Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bath rancher features a light-filled, easy-flow floorplan with two ensuite bedrooms for added privacy and versatility. The home offers a garage and separate laundry room and opens to a charming backyard deck - ideal for morning coffee or evening gatherings. The spacious backyard provides ample room for a pool, enhancing the home's outdoor living potential. Comfortable, functional and perfectly suited for enjoying the Eastern Shore lifestyle.

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 CABINET KITCHEN WITH QUARTZ COUNTERTOP, TILES SUN ROOM WITH WOOD STOVE, 2 CAR GARAGE . THIS SOLID RANCHER IS A GRETA PLACE TO COME TO ON WEEKENDS OR FOR ALL YEAR ROUND LIVING. PRICED UNDER APPRAISED VALUE !

Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully reimagined through comprehensive renovations completed in 2023 and 2024. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms, this home offers an elevated blend of sophistication, comfort, and timeless Eastern Shore charm - located on East Chew Street, the property is walking distance to the harbor, boutiques, and celebrated dining of St. Michaels. From the moment you enter, the quality is unmistakable. Clean sightlines and an open, interconnected floor plan create an ideal setting for both everyday living and effortless entertaining. Throughout the home, curated lighting, custom millwork, elegant crown molding, custom doors, and redesigned fireplaces reflect a commitment to thoughtful design and enduring craftsmanship. The main level features a primary suite with beautifully updated finishes and refined details, including a fully renovated primary bath. There is a second primary suite on the second level as well with a renovated bath. The main residence offers four ensuite bedrooms; all baths have been renovated each providing privacy and comfort for family and guests alike. A standout feature of the property is the fully independent renovated permitted apartment above the two-car heated garage. Complete with a full kitchen, bath, washer and dryer, office area, and sleeping loft, this versatile space is ideal for extended family, guests, a private studio, home office or potential rental income. At the heart of the home, with secure access to the main house from a two garage, providing off street parking and easy kitchen access, is both functional and thoughtful. The kitchen showcases high-end appliances with gas, exquisite finishes, and custom lighting. The kitchen flows seamlessly into the living and dining areas, where fireplaces add warmth and ambiance. Upstairs, an additional media lounge area, a second upper-level primary suite offers a serene retreat with updated bathroom cabinetry and fixtures, a fireplace, and a beautifully designed custom walk-in closet. A third en-suite bedroom along with a spacious laundry room adjacent to the media room, enhance convenience. The fourth en-suite bedroom is on the third level with additional living space and a renovated bathroom. Outside, professionally newly designed landscaping and a full irrigation system provide year-round beauty, while the blue slate terrace - framed by expertly trained David Austin climbing roses - a grilling area creates a private outdoor sanctuary for entertaining or quiet reflection. Modern conveniences include Wi-Fi broadband, advanced home monitoring systems, and a Hikvision doorbell with remote access, updated HVAC, Renaldi tankless hot water systems both add comfort and peace of mind. A concrete crawlspace with a dehumidification unit is part of this well-built home. Perfectly positioned near the waterfront and within easy reach of Easton and Oxford, this turnkey home is ideal as a full-time residence or a sophisticated weekend retreat. With flawless finishes, flexible living spaces, and an unrivaled location, this property represents the pinnacle of Eastern Shore living. Schedule your private showing and experience its exceptional character firsthand. On a price per sq. ft. basis this property represents an excellent value and the new two-level apartment above the heated garage is an exceptional rental investment opportunity, guest quarters, studio or office.

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.

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 access to the backyard through sliding glass doors. Both bathrooms have been remodeled, and additional updates include new electrical outlets and switches, a 2024 electric panel, HVAC (2025), and a 2026 hot water heater. Outside, the fenced yard includes a patio, sodded lawn, professional landscaping, and an irrigation system. A 14'x20' insulated shed with electric and heating/air offers flexible use as a workshop or studio. The home also features a newer roof, siding, gutters, and downspouts (2 years), plus a 5-year-old encapsulated crawlspace with sump pump and dehumidifier. Complete with a private driveway and well-maintained exterior, this property combines convenience, updates, and location.

Set on 19.5 private acres just minutes from historic waterfront Saint Michaels, this exceptional 4,492 sq ft residence offers the perfect blend of space, privacy, and convenience. The home features four bedrooms and two and a half baths, with expansive living areas ideal for both everyday living and entertaining, including a well-appointed chef's kitchen. The thoughtfully designed layout includes a designated space for a future elevator, adding flexibility and long-term convenience. A separate car barn provides ample storage for vehicles, hobbies, or workshop space. Enjoy the nicely fenced rear patio area, perfect for outdoor relaxation or entertaining. Surrounded by peaceful countryside yet close to the charm, dining, and waterfront attractions of downtown Saint Michaels, this property presents a rare opportunity to enjoy Eastern Shore living at its finest. **Note the forest area behind the house has been put into the DNR's Forest Stewardship Plan which allows the home owner to keep the AG tax discount without having to grow crops and/or livestock.

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 - the perfect escape and recharge from your weekly routine. Welcome to 204 E Marengo Street, St. Michaels, MD - where coastal charm meets small-town living. Just two blocks from the Historic District and 1.5 blocks from water access, including a marina and boat ramp, this fully modernized cottage perfectly captures the laid-back Eastern Shore vibe. Carefully designed for minimum maintenance and effortless living, it offers main-level living, sun-filled rooms, modern appliances and HVAC and a beautifully updated full bathroom to optimize lifestyle comfort and minimize effort. Step outside and discover your own backyard retreat - an entertainer's dream with an in-ground pool, detached garage, with electric, refrigerator, and large workbench, and a beach-inspired outdoor bar (with cable TV) that's perfect for hosting friends or unwinding after a day on the water. The home has been thoughtfully maintained with key updates, including a new roof (2024), water heater (2018), HVAC (2018), washer/dryer (2022), and stove and refrigerator (2023), beautiful plantation shutters, and Thompson Creek Windows (2018) and updated crawl space (2025 - new French drain, insulation and vapor barrier) - making it completely move-in ready. And being outside the Historic District provides freedom of home and grounds changes without Historic District oversight. With coffee shops, boutique shopping, dining, and the waterfront all within easy reach, this home is ideally situated to enjoy everything St. Michaels and the Eastern Shore has to offer. Don't miss your chance to own a slice of paradise - a true weekend getaway that's closer, cozier, and more affordable than you ever imagined.

Welcome to "Mostly Porches" an exceptional coastal retreat with captivating views of the harbor, perfectly situated on a spacious .41 acre corner lot just around the corner from the shops and restaurants of St. Michaels. Built in 2018 with virtually maintenance-free construction, this beautifully designed home offers the ideal blend of comfort, style, and convenience in a rare St. Michaels setting. Inside the floor plan is filled with an abundance of natural light and enhanced by soaring cathedral ceilings, creating an airy and inviting atmosphere ideal for both every day living and perfect for entertaining. The main living area incorporates the living, dining and kitchen and offers easy access to the extensive porches the home features, including the screened-in porch with a gas fireplace and views of the harbor. In the great room there is also a "hidden" pantry along the dining area wall with plenty of shelving and storage. Custom built-in bookcases line the living area wall to the left of the propane fireplace which incorporates a built-in 90 lb per day nugget ice-maker. The gourmet kitchen is centered around a large island and features SS Thermador appliances including a duel fuel range with a six burner gas cooktop and electric oven, and an under counter wine fridge and under counter beverage fridge in the island. The contemporary design features the primary suite, 2nd bedroom, office/den, full bath and utility closet all on the main level. A standout out feature of this property is the 2nd level private guest suite, which is a licensed income-producing vacation rental, offering flexibility for guest or the opportunity for supplemental income. This private enclave includes a small sitting area, private bath and kitchenette with under counter refrigerator drawer, under counter freezer drawer, Keurig coffee maker, counter top microwave, and free standing shelves. The property also includes an attached 2 car garage, fire pit, raised garden beds with drip irrigation, and full irrigation system in the yard plus an oversized attached 2 car garage. With its desirable location close to all St. Michaels has to offer, exceptional amenities, and low-maintenance design, this is a rare opportunity to own one of the town's newer build homes with water views and income producing opportunity.

Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come By Chance's, design team. Across living spaces, you'll enjoy quiet refinement of the original 1996 construction as hand-scraped hardwoods, tailored millwork, crisp coastal hues, and light-filled windows frame seasonal harbor moments. Host visiting guests near your wood-burning hearth where built-ins hold favorite reads, collected shells, and travel mementos. Here, both curated and comfortably lived-in personality mirror mornings with coffee and dinner aromas from your breezy kitchen of high-end appliances, stone surfaces, and a central island. While everything from simple breakfasts to generous crab feasts overlook nautical views from your sunlit sitting room, you're sure to linger long after meals from either of the double balconies. Here, let casual conversation entertain, then settle within either of your three serene bedrooms letting two full and one half baths refresh. Outside, toss yard toys for a four legged friend, cast off kayaks towards quiet coves, or set sail into the open expanse of the Chesapeake Bay. Closer to home, afternoons unfold, just a stroll's-distance away toward daily discoveries within nearby St. Michaels shops, caf s, museums, and the yacht club.

ST MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE BUZZLING TOWN OF ST MICHAELS AND ITS MANY RESTAURANTS, SHOPS , CAFES, THE MOTOR MUSEUM AND THE CHESAPEAKE BAY MARITIME MUSEUM. WHERE EVER YOU TURN YOU SEE WATER. FEEL THE BREEZES , LOUNGE BY THE POOL OR NAP IN YOUR HAMMOCK UNDER THE SHADY TREES BY THE SHORELINE. THIS THREE BEDROOM SOLID BRICK HOME WITH OPEN FLOORPLAN , DOUBLE SIDED FIREPLACE , WOOD FLOORS , RENOVATED BATHROOMS AND KITCHEN , GEOTHERMAL HVAC IS ALL ABOUT EASY LIVING AND TAKING ADVANTAGE OF THE OUTDOORS. CHARMING PATIO WITH STONE WALLS , DECK WITH OUTDOOR KITCHEN, HOT TUB . STEPPING DOWN TO THE OUTDOOR SHOWER AND SWIMMING LAPS IN THE POOL. THE DOCK OFFERS 3 MLW, A BOATLIFT AND BOAT LAUNCH . THERE IS A 2 ROOM STUDIO WITH COVERED PORCH TO ENJOY THE WATER VIEWS. ENCAPSULATED CRAWLSPACE AND MANY UPGRADES. EASTERN SHORE LIVING AT ITS BEST.

Improved pricing on this beautiful four-bedroom contemporary home, now offered at $725,000. Privately situated on a on a one + acre lot overlooking the 12th fairway of the Links at Perry Cabin golf course, this light-filled interior residence features a vaulted living room with fireplace, and wood-burning insert for added warmth and comfort, spacious family room and dining room, and a bright sunroom that opens to a relaxing private deck. The main level primary ensuite includes two walk-in closets and new carpeting installed in 2024, creating a comfortable retreat for everyday living. Significant 2024 improvements include a new roof and gutters, representing approximately $90,000+ in recent upgrades. Double-pane windows throughout enhance energy efficiency and create a peaceful interior environment. Home is supported by three HVAC systems professionally serviced and maintained by Shaw's along with two water heaters for enhanced comfort and efficiency. Nestled in a wooded setting that provides both privacy and scenic golf course vistas. The two-car garage offers abundant space for hobbies, storage, or workshop use, while the expansive driveway can comfortably accommodate 7+ vehicles. A wonderful opportunity to enjoy quiet golf course living just minutes from historic St. Michaels, restaurants, shops and the waterfront.

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 easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home's historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland's most desirable waterfront communities.

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 staying part of the conversation while cooking. Just off the kitchen, the screened porch becomes a natural extension of the space, making it easy to move outside for dinner, relax or a quiet evening overlooking the gardens. The first floor also includes a separate dining room for more traditional gatherings, along with a front sitting room or library that works equally well as a home office or quiet retreat. The primary suite is located on the main level, offering everyday convenience with a spacious walk-in closet and private bath. Upstairs, two additional bedrooms are paired with a large second living area - ideal for guests, a media room, or a flexible space that can adapt over time. Outside is where this property really sets itself apart. The owner, a horticulturalist, has created layered, mature landscaping that feels intentional and established - not something you can easily replicate. Backing to trees, the lot offers privacy and a sense of calm that carries through every season. Back Creek Landing itself is a favorite for a reason. With roughly 40 homes, it offers a close-knit feel, walking trails through the woods and around ponds, and a picnic area with a large gazebo. One of the trails even connects directly to St. Michaels Market - an easy walk for everyday errands. There's also community access to San Domingo Creek, with a dock and kayak storage for those who want to get out on the water. And when you're ready for town, it's just a short bike or golf cart ride to restaurants, shops, and the harbor - close enough to enjoy, yet far enough to come home to quiet. With a two-car garage, main-level primary suite, and flexible living spaces throughout, this is a home that offers both practicality and a setting that's hard to duplicate.

This home allows for a 3.12% FHA Assumable Loan! Welcome to easy Eastern Shore living in the charming waterfront town of St. Michaels! This 3-bedroom, 2 bath, 1,232 sq. ft. home is located in the desirable community of Rio Vista offering direct access to the Miles River, complete with a community dock, boat slips, and boat ramp - perfect for boating, crabbing, paddleboarding, or sunset cruises. Enjoy the relaxed coastal lifestyle just minutes from shops, restaurants, marinas, and everything that makes St. Michaels so special. Residents also enjoy access to a community pool for summer fun. Whether you're looking for a full-time residence, weekend getaway, or investment opportunity, this home offers the ideal blend of comfort, location, and waterfront amenities.

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 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. 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.

The George E. Shockley House (c. 1890) is a rare historic gem in the heart of St. Michaels, just moments from the harbor, fine dining, unique shops, walking trails, and the renowned Chesapeake Bay Maritime Museum. Beautifully preserved and enhanced with significant structural improvements by Victor MacSorley, this distinguished residence blends period charm with modern comfort and is notably not subject to St. Michaels Historic District regulations. The home features an exceptional main-level primary suite with vaulted ceiling, three walk-in closets, en suite bath, and serene views of the private yard; an updated kitchen with large center island, granite countertops, stainless steel appliances, abundant storage, and casual dining overlooking the gardens; three main-level living spaces including a bright sunroom/library, spacious family room with brick fireplace, and the original welcoming living room; along with a formal dining room and powder room. Upstairs are two additional bedrooms and a full bath. The fenced backyard offers a patio beneath a magnificent magnolia, and a detached structure with a half bath provides the perfect space for a private office, studio, or creative retreat, complemented by a potting shed and additional storage. Off-street parking from both New Lane and E. Chew completes this exceptional in-town offering.