St Michaels MD Real Estate & Homes for Sale

Inviting townhouse in the St. Michaels Martingham community with views across the Links at Perry Cabin fairway, offering easy Eastern Shore living. From the upstairs living areas, enjoy lovely, elevated views, abundant natural light, and a sense of openness that enhances the homes warm, inviting feel. The upper-level living area features shining hardwood floors, and the home has been recently painted, professionally cleaned, and includes a new roof for added peace of mind, while a new Trex deck offers an ideal place to relax and enjoy the park-like, scenic setting. The home is turnkey, with the HOA maintaining the beautifully kept grounds, allowing for low-maintenance living. Ideally located just minutes from downtown St. Michaels, with shops, dining, and waterfront attractions nearby. An excellent opportunity as a primary residence, weekend retreat, or investment property. Check out the NEW Virtual Staging photography and video... to envision making this home your own!

Your picture-perfect St. Michaels Bungalow on the coveted W. Chestnut Street. The owners completed a full renovation in 2023. Designer finishes throughout. Attention to detail, light placement and thoughtful preservation of its original style. The screened front porch welcomes you in with it's beautiful woodwork and sets the pace for this Chic, move-in ready Shore Home. Situated on a double lot with room for a pool. Fenced rear yard for room to run. One block to the Community pier on San Domingo Creek, kayak racks and walking path. Full details on the whole renovation are in the documents file. Note...Heated square footage is 1914 sq. ft.

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 fresh interior painting, a deep cleaning and it is "move in ready" It is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2 car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the "Conservatory". It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for a master suite. Two sets of French doors open to either the front lawn or side yard for entertaining. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the sunrises and sunsets. With the lowest price per square foot for a Luxury, Waterview, in town home, it is also a comparatively excellent value.

Wonderful opportunity to live in the quaint, picturesque and historic town of St Michaels at a great price. New carpeting, and new paint. Move in ready. Well kept, light filled townhouse with 2 bedrooms, one bath and fenced back yard. Must be primary residence. 2 assigned parking spaces. Walkable to all St Michaels has to offer.

A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod-style 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, electric service, and fiber-optic internet-allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shores most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces that can be tailored to the buyers preferences while preserving privacy and connection to the natural setting. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and tucked away. Approximately three times the size of a typical in-town lot, the parcel allows generous room for outdoor living and thoughtful home placement, with driveway access possible from Miles Avenue, Canton Street, or both, depending on final design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet-allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shores most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

Located within 2 miles of historic St. Michaels this exceptional waterfront estate blends timeless elegance with a resort-style setting. This 4,200± sq. ft. custom, single-level all brick residence showcases soaring ceilings, an abundance of natural light, and panoramic views of Broad Creek from almost every room. A huge great room featuring a large brick fireplace and open living / dining options. There is a gorgeous gourmet kitchen complete with quartz counters, stainless steel appliances and walk in pantry, seamlessly flowing into a spacious family room with a timeless double sided brick fireplace and built-in bookcase. An architecturally stunning screened octagonal porch-perfect for relaxing or entertaining. A brick-floored sunroom with gas fireplace and pool bath leads to an expansive patio overlooking the waterside pool, framed by a rock waterfall, and custom gazebo. The luxurious primary suite features cathedral ceilings, French doors leading to the sunroom and a spa-inspired bath with walk in tile shower and soaking tub. Two additional en-suite bedrooms, a large den with custom built-ins perfect for library or additional bedroom, and a spacious butlers pantry with granite counters, extra refrigerator, stainless sink and additional cabinetry. A separate study and conditioned workshop offer versatile space. Set on five beautifully landscaped acres with southern exposure, the property boasts 370+/- feet of protected shoreline and a 350-foot private pier with 6 feet of deep water. Boating enthusiasts will appreciate the 15,000-lb and 8,000-lb lifts, two additional slips, and a floating dock. A gated 30' x 40' flower/vegetable garden with raised beds, an oversized 2-car garage and large garden shed complete this beautiful home. Septic is for 3 BR but office could be BR #4.

Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the â??Oakwood Associationâ? belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting todays residents to St. Michaels vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.

Back Creek Landing home for sale in St. Michaels, MD - located in one of the towns most desirable neighborhoods, known for its peaceful setting, friendly community, and proximity to downtown St. Michaels. This home is just minutes away by bike or golf cart, offering easy access to shops, restaurants, the harbor, and waterfront activities while still feeling private and serene. This beautifully maintained single-family home features a covered front porch, ideal for relaxing, entertaining, or enjoying quiet mornings. Inside, the flexible floor plan includes a main-level living room or home office with pocket doors, a formal dining room, and an open-concept kitchen and great room - a layout highly sought after by todays buyers. The kitchen offers ample cabinetry, generous counter space, and a large center island with seating, making it perfect for everyday living and entertaining. The great room opens to a covered rear porch overlooking community ponds, with western exposure and sunset views. A private patio and pollinator garden enhance the outdoor living space. The first-floor primary suite is a standout feature, offering a walk-in closet with custom built-ins and an updated en-suite bath. Additional main-level highlights include a powder room, laundry room, and continuous flooring throughout, creating a seamless flow. Upstairs, youll find two spacious bedrooms with large closets, a full bath, and a large bonus room ideal for guests, a media room, home gym, or second family room. A walk-in attic provides excellent storage, a rare and valuable feature. Back Creek Landing is a planned residential community offering walking trails, scenic ponds, picnic areas, and water access to San Domingo Creek, complete with a community dock and kayak storage - perfect for buyers seeking the Eastern Shore lifestyle with kayaking, nature, and outdoor recreation. Freshly painted and move-in ready, this St. Michaels home combines main-level living, outdoor spaces, water access, and proximity to town - a highly desirable combination that is rarely available. ð?? St. Michaels, MD 21663 ð??² $795,000 ð?? 3 Bedrooms ð?? 2.5 Bathrooms ð?? 3,166 sq ft Dont miss your opportunity to tour this exceptional Back Creek Landing home. Schedule your private showing today.

This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhanced with numerous upgrades. The owners added luxury vinyl plank flooring to the second level, Hunter Douglas plantation shutters with independent top and bottom operation, recessed lighting upstairs, and a high-end full-size Electrolux washer and dryer. Additional features include a smart home system with Nest locks, thermostats, doorbell camera, and smoke detectors, as well as an inground lawn irrigation system. Outdoors, the private backyard has been beautifully finished with professional landscaping, privacy fencing, and a Techno-Bloc custom paver patio. A welcoming front porch with flower boxes and rocking chairs sets the tone. Inside, the main level offers a cozy front foyer/den that opens to a spacious great room with living, dining, and kitchen areas. The gourmet kitchen boasts quartz countertops, a large island, gas range, pantry, and pendant lighting, with sliding doors that lead directly to the rear yard retreat. Upstairs, youll find four bedrooms and two full baths, including a primary suite with its own private bath. Set at the end of a non-through street just one block from the heart of St. Michaels, the location is ideal. Enjoy quiet evenings on the porch, gatherings in the backyard, or a few short blocks into town and the waterfront. From here, you can access shops, dining, the Chesapeake Bay Maritime Museum, and seasonal events. Even the town ice cream shop is only a few blocks away. Whether relaxing at home or exploring everything St. Michaels has to offer, this property provides the perfect blend of comfort, convenience, and small-town charm. Move-in ready and truly immaculate!

This handsome home is nestled in the trees on a quiet cul de sac in Rio Vista. This popular neighborhood is five minutes from historic St. Michaels and offers public sewer and water with no town taxes. Rio Vista has a waterfront picnic area and boat slips for rent to residents for $225 per slip. This home has been very nicely maintained by the original owner. It offers one-level living, with a primary suite and laundry on the first floor. The kitchen overlooks the breakfast area and family room, which features a vaulted ceiling and gas fireplace. Upstairs are two additional bedrooms plus an office that could be a fourth bedroom (no closet). An attached garage adds to the convenience.

Discover a beautifully crafted custom home tucked within the peaceful St. Michaels community, where refined design meets everyday comfort. This exceptional residence offers 4 generously sized bedrooms and 3.5 thoughtfully designed bathrooms, filled with premium details throughout. The versatile gas fireplace anchors the inviting main living space, complemented by custom built-ins that add both character and functionality. The expansive primary suite is a true retreat, featuring an oversized walk-in closet and a spa-inspired bathroom with a large custom shower and new fixtures. A second-floor en suite bedroom provides an ideal option for guests or multigenerational living. Outdoor living shines on the sprawling Trex deck, complete with a Sunsetter awning and a fully fenced backyard-perfect for entertaining or unwinding in privacy. Additional highlights include a large walk-in storage attic with the potential to convert into a fifth bedroom, office, or media room. Recent upgrades such as a newer first-floor HVAC system, a brand-new second-floor HVAC, an updated 80-gallon hot water heater, and a freshly painted interior ensure comfort, efficiency, and move-in readiness. Set within a tranquil 40-acre enclave featuring walking trails, ponds, and waterfront access along scenic San Domingo Creek, this home offers a rare blend of natural beauty and convenience. Enjoy easy access to downtown St. Michaels while benefiting from no town taxes. A truly special home that delivers relaxed luxury, space to grow, and an exceptional Eastern Shore lifestyle.

This is a rare chance to secure meaningful savings and a beautiful home in one of the Eastern Shores most desirable communities. Welcome to Martingham-home to the newly redesigned Pete Dye course, The Links at Perry Cabin, and just minutes from the heart of historic St. Michaels. Enjoy world-class dining, boutique shopping, and waterfront charm, all right at your fingertips. Set on 1.13 open acres with a tree-lined backdrop for privacy, this 3BR/2.5BA Colonial offers the space, setting, and lifestyle buyers are searching for. Inside, youll find a bright and spacious floor plan, an updated island kitchen, and a large family room featuring a wood-burning fireplace and beautiful beam ceiling. Upstairs, the generously sized primary suite includes a private balcony overlooking the backyard-a perfect retreat. Two additional oversized bedrooms offer flexibility for guests, office space, or hobbies. Outdoor living shines here: a large deck flows to the fire pit and expansive, level backyard-ideal for gatherings, relaxing, or simply enjoying nature. With its incredible location, valuable seller credit, and inviting living spaces, this home is an exceptional opportunity. Dont miss your chance to tour it and experience the Martingham lifestyle for yourself.

NEW PRICE! Located minutes from downtown St. Michaels, â??Aqua Vitaeâ? the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400 of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & â??party barnâ? all highlighted by a waterside pool, pier w/ 4 MLW, pine grove, putting green, extensive landscaping & incomparable craftmanship. The 12,000 SF main residence, positioned to prioritize water views, welcomes you via prominent double lead-glass doors & a grand 3-story foyer w/ dual-staircase. The â??river roomâ? w/ 2-story octagon copula offers 270â?¦ views of the property & creek. The TV room w/ 3 exposures & gas-burning fireplace offers double French doors on two sides leading to the wrap-around flagstone patio. The stunning gourmet kitchen is a true chefs dream. Offering oversized island, built-in media/storage cabinet, coffered ceiling, fireplace, 3 sinks, double Subzero fridges w/ freezer drawers, 2 beverage drawers, 3 dishwashers, Wolf microwave & a stainless-steel Lacanche range with 6-burners, pot warmer, warming oven, & 2 ovens. Complimenting the kitchen is a large walk-in pantry w/ dishwasher, sink & extra freezer in hall. Off the kitchen is a covered porch w/ gas fireplace & â??ghost screens, a perfect spot to enjoy evenings. A large open dining room has 2 custom built-in display cases. The grand salon w/ bay window, gas-fireplace & intricate mantel is reminiscent of Paris. Adjoining the salon is the handsome 2-story curly cherrywood library w/ custom display cases & leaded-glass pocket doors. The adjoining climate-controlled wine room has a wet bar & storage for 750+ bottles. Wood floors flow throughout the entire main level. The main level is completed by an office, powder room & laundry to service the pool, 2 additional powder rooms, elevator to all 4 levels, mud/dog room, rear spiral staircase, guest suite w/ ensuite bathroom, & 2-car attached garage. The 2nd level offers a generous primary suite w/ fireplace & full length terrace overlooking the water. Her wing features dressing room w/ custom built-ins, separate sitting room, & a luxurious bathroom w/ marble tile, separate shower, jetted tub, & vanity. His wing offers an office w/ fireplace, paneled closet leading to separate bathroom w/ shower, travertine stone, & vanity. From his office access the 2nd level of library, open to below. Just off of the primary suite is a bar area/kitchen. 3 additional bedrooms, each w/ ensuite bathroom, and a laundry room complete the 2nd level. The 3rd level offers theater/rec room, play area, bedroom w/ ensuite bathroom, powder room, & ample storage. The lower-level houses utilities, storage, & enough room for an exercise area. The charming guest cottage sits amongst extensive landscaping. The main level offers a full kitchen, dining area, living room, sunroom, large family room, 2 bedrooms w/ shared bathroom, additional guest bathroom, & large entertaining room. Upstairs is a full bedroom w/ ensuite bathroom. The unfinished lower level offers storage. The party barn originally built for boat storage was designed to look like an old Pennsylvania barn w/ 4 of stone around the base. Flanked by 2 garage wings allowing for 4+ cars & capped w/ a cupola, the shingled-style barn has two large doors on either side of the building that allow for a trailered boat or 4+ more cars. The 2nd level is a loft w/ sleeping/living area w/ full bathroom, plumbed for potential kitchenette, front & rear terraces, & a spiral staircase to a crows nest w/ amazing views. There is a full property generator & a dog run w/ kennel just off the rear. Outside enjoy the benefits of beautiful shore living amongst the verdant grounds, mature landscaping & exceptional views. The pier offers 4 MLW & the shoreline is fully rip-rapped w/ natural plantings.

Fabulous St. Michaels location near Miles River, St. Michaels Marina, Inn & Spa, St, Michaels Winery, area schools and so much more! Enjoy all the benefits of a coastal lifestyle in this charming & scenic historic town. Build your dream home on a attractive homesite minutes from everything and everywhere you want to be. The Pointe offers an impressive open kitchen with island, pantry and large dining area perfect for all those gatherings and get-togethers. A very spacious great room is adjacent to the cooking and dining area. The main level also offers a welcoming foyer and 2-car garage. Upstairs youll find a tranquil owners suite with a large walk-in closet and bath featuring dual sinks, soaking tub and walk-in shower. Three additional bedrooms, hall bath and laundry room complete the second floor. An optional full basement provides ample living and storage space including an opt. rec room, opt. media room, opt. fifth and sixth bedrooms, and a third or fourth full bath!

Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe. Time to make your personal selections. Make this home your personal statement. Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more. Make this your dream home.