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5 Beds 3 Baths
Recently updated Kitchen, flooring in Foyer, Powder Room, Mud Room ,and Kitchen. All New Stainless Steel appliances and New light fixtures. A Short Stroll from Downtown St Michaels and The Harbor. A Very Spacious Home for Family and Friends. Enjoy your formal Living and Dining Rooms off of foyer with access to Large Kitchen and Family Room. Step through 1 of 3 Sliding Doors onto your 47x 11 Deck off of Dining Room, Kitchen and Family Room. A Great Entertaining Home. Almost a half acre of privacy to watch the Nature around You. A nice walk or Bike Ride to all that this Historic Village has to offer, yet No Town Taxes.... The Community Pier and Picnic Area is just a short walk away. What's Not To Love !

220 Tyler Ave, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 221-8000

5 Beds 6 Baths
New Construction Waterfront in St. Michaels. Nantucket-Style Manor Home with everything on your “Wish List”. Main house with 5 Bedrooms (First Floor Primary Suite), separate study, first floor guest room (en suite); open floor plan with high ceiling, Family/Dining Combo, gourmet kitchen with quartz tops, Stainless Steel Appliances, mud room and a full bathroom to service the pool. Second Floor features Game Room, laundry room, two additional bedrooms (both en suite) and a second floor Primary Bedroom suite with private balcony. High-end materials and craftsmanship throughout. Additional features include a poolside porch with fireplace, patio with outdoor fireplace, covered front and waterside porches. A separate guest house (unfinished) on the water’s edge, in-ground pool, boat house with 7’+/- MLW, detached 3-car garage. Majestic Oak trees, breathtaking western exposure of San Domingo Creek.

974 San Domingo Ct, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

3 Beds 2 Baths
Welcome to your fully renovated dream home at 1104 Harrison Ave! This charming residence has undergone a top-to-bottom transformation, leaving no detail overlooked. From the moment you step inside, you'll be greeted by the impeccable craftsmanship and attention to detail evident in every corner of this property. Featuring three spacious bedrooms and two full baths, this home offers ample space for comfortable living. The addition of a sunroom with central air provides the perfect retreat for relaxation or entertaining guests year-round. The heart of the home, the kitchen, is a true chef's delight with its modern amenities and open layout, ideal for hosting gatherings and creating culinary masterpieces with a gorgeous island adding not only additional counter space but storage as well.. Situated on a generous corner lot, this property boasts a U-shaped driveway, providing ample parking space for residents and visitors alike. The one-car garage offers convenient storage options, while the expansive backyard presents endless opportunities for outdoor enjoyment and customization to suit your lifestyle. With a new roof, HVAC system, water heater, and updated flooring and drywall throughout, this home offers not only stunning aesthetics but also peace of mind knowing that everything has been meticulously upgraded for your comfort and convenience. Don't miss your chance to make this meticulously renovated home yours. Schedule a showing today and experience the perfect blend of modern luxury and timeless charm at 1104 Harrison Ave!

1104 Harrison Ave, Saint Michaels

Listing courtesy of Keller Williams Flagship of Maryland. Contact:

3 Beds 3 Baths
An historic gem, centrally located in the heart of St. Michaels, close to the harbor and many amenities that our town has to offer - fine dining, unique shops, walking trails and the popular Chesapeake Bay Maritime Museum. Rarely do you find a property that can offer a sumptuous main level primary suite with 3 walk-in closets, en suite bath and vaulted ceiling overlooking the private yard. The updated kitchen is a cook's oasis - large center island, abundant counter and storage space, SS appliances, granite countertops and a delightful casual dining area that also overlooks the gardens. 3 main level living areas include a bright and airy sunroom/library, large family room with brick fireplace and the original living room that welcomes you as you enter the home. A formal dining room and powder room complete the main level. Upstairs are two additional bedrooms and a full bath. The private backyard is fenced with a patio under the magnificent magnolia. A bonus is the detached studio/office with half bath, garden shed and storage area. Off-street parking on both New Lane and E. Chew. This house is known as the George E. Shockley House c. 1890 but is not subject to the St. Michaels Historic District regulations.

114 E Chew Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

3 Beds 2 Baths
Welcome to 1109 Jefferson Avenue, a meticulously renovated home in Saint Michaels, Maryland's charming Rio Vista neighborhood. This beautifully residence offers the perfect blend of modern comfort and coastal charm, boasting an ideal location near downtown Saint Michaels and the scenic Miles River waterfront. Inside you will discover a thoughtfully designed interior featuring an open-concept layout, where natural light illuminates the spacious living areas. The gourmet kitchen is a chef's delight, with sleek countertops, stainless steel appliances, and ample cabinet space. Retreat to the inviting bedrooms, including a luxurious primary suite with a private ensuite bathroom for added convenience. Additional home highlights include updated flooring, elegant fixtures, and a screened-in porch, perfect for evening entertainment. Outside, enjoy the tranquility of the Rio Vista neighborhood. Take advantage of the nearby waterfront amenities, including access to the Miles River and a public boat launch for all your aquatic adventures.

1109 Jefferson Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

5 Beds 7 Baths
Travel down a mature, holly tree-lined drive and One Beverly reveals itself with understated Eastern Shore elegance. Situated on the 9 acre original farmstead of the 1867 Beverly Manor, this Georgian home provides a southwestern view overlooking San Domingo and Broad Creeks. The 5-bedroom main house, first occupied in 2003, is a traditional Georgian design meticulously built according to exacting standards to include handmade brick applications, historical window selections, exotic hardwood flooring, limestone fireplaces, custom architectural elements, and an elevator. Craft woodworking is displayed throughout the home's spiral staircase, large kitchen, pantry, and morning room, bathrooms, powder rooms, library, sunset room, fireplace mantles, snooker room, mudroom, map room, ceiling and baseboard trims, and exterior cornices. The central River Room 19ft ceiling provides expansive views of the creek waters and overlooks the terrace which is accessible through triple hung windows. The kitchen and pantry are outfitted with high-end Viking, Miele and Sub-Zero appliances. The large mudroom includes a laundry station, shower, sauna, powder room, refrigerator drawers, a custom farm sink, and an abundance of storage. This homesite includes a guest cottage nestled close to the water, the original carriage house now converted into an office with direct high-speed broadband service, a large pool, an outdoor Viking grill, a Morton barn, a freshwater pond, a greenhouse, and raised brick cutting garden. Established landscaping and majestic trees provide a lush environment to enjoy your Eastern Shore lifestyle.

24629 Beverly Rd, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: (410) 822-6272

3 Beds 3 Baths
Welcome to your dream home in the charming town of Historic St. Michaels! This stunning single-family residence, crafted by the reputable Beracah builder, offers over 2000 square feet of luxury living space, featuring three bedrooms, two and a half baths, and a one-car garage with plenty of room for storage. Epitomizing modern comfort and convenience, this home boasts a thoughtful layout spread across two levels, adorned with high-end finishes throughout. Its unbeatable location further enhances its appeal, offering the perfect blend of comfort and style. With newer construction ensuring modern amenities and a fresh aesthetic, you'll find the heart of the home in its gourmet kitchen, complete with exquisite white cabinets, sleek quartz countertops, and top-of-the-line stainless steel appliances. The spacious breakfast bar and cozy eat-in area provide the perfect setting for dining and entertaining guests. Retreat to the elegant master suite, complete with beautiful barn doors leading to the ensuite bathroom featuring granite countertops, Carrara tile in the large walk-in shower, and a spacious walk-in closet. Upper level features include two large bedrooms, a full bath, a large loft and sitting area, and the possibility of converting a large walk-in attic into an office or fourth bedroom. Step outside to enjoy the outdoor oasis, where privacy and serenity await in the fully-fenced backyard with landscaping and a stone patio, ideal for outdoor dining and relaxation. Nestled in a peaceful cul-de-sac, this home offers tranquility while being just a short walk away from shops, restaurants, the nature trail, and scenic St. Michaels harbor. Convenience and accessibility to amenities, schools, and transportation further enhance its appeal. Additional features include a dual-zone HVAC system, luxury vinyl flooring on the main level, main level walk-in laundry room, powder room with pedestal sink, whole house fan for energy efficiency, fully encapsulated crawl space, and ample sunlight and closet space throughout. Ask for further information. Don't miss the opportunity to experience the epitome of coastal living in Historic St. Michaels. Schedule a viewing today!

107 Chesapeake Ave, Saint Michaels

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

3 Beds 2 Baths
Welcome to your dream home in an adorable small town! This newly built rancher comes with elegance and comfort. Featuring a well-designed Open floor plan, this home offers spacious living areas ideal for both relaxation and entertaining. As you step inside, you'll be greeted by the warm ambiance of the inviting living room, perfect for cozy gatherings with loved ones. The adjoining kitchen is a culinary haven, featuring gorgeous Quartz countertops, Stainless Steel appliances, and Tastefully selected cabinetry, catering to your every culinary need. The rancher comprises three generously sized bedrooms, providing ample space for rest and rejuvenation. The master suite is a serene retreat, complete with a luxurious ensuite bathroom, offering a tranquil escape after a long day. Located in the cute town known as St Michaels, this property offers the perfect blend of tranquility and convenience. Enjoy easy access to local amenities, some of the finest shops, and dining establishments, while also relishing in the serene ambiance of small-town living. Don't miss the opportunity to make this newly built rancher your forever home. Schedule a showing today!

110 Lee St, Saint Michaels

Listing courtesy of EXP Realty, LLC. Contact: (888) 860-7369

6 Beds 11 Baths
NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” 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, & “party barn” 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 “river room” w/ 2-story octagon copula offers 270◦ 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 & “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 crow’s 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.

8620 Bozman Neavitt Rd, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact:

3 Beds 2 Baths
Beautifully renovated 3- bedroom, 2- bathroom cottage located in Stunning St. Michaels. Large spacious lot with room for a pool (buyer to confirm size and location with talbot county), located on a water street within walking distance to the waterside park, restaurants, shops and the YMCA. This home features refinished hardwood floors, gas fireplace, large family room, gourmet kitchen, 2 guest rooms, primary bedroom with ensuite bathroom, guest bath, designated laundry room, and Florida room, first floor living at its best! Enjoy the amenities of public sewer and water without in town taxes. Because of this homes location it could be an air B&B, as long as the county approves. Call today to be the first to see this perfect cottage.

402 Seymour Ave, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: (410) 822-6272

This business currently known as Subway 62461 is being sold and includes all the equipment, including the walk-in freezer and walk-in refrigerator, sinks, ovens, proofer, hot well, cold serving unit for veggies and another one for meat; cold drink dispenser; refrigerated beverage container; Everything was newly purchased in 2015 and is according to code. Subway 62461 is a franchise and can be purchased from Subway. The building is leased. Dream come true owning a business you can own and enjoy the many lovely customers that live around the area as well as the ones that return year after year for the crabbing, fishing, boating, and just the relaxing ambiance of the water. Contact agent for more information. Income/expenditure records will be provided once a "contract" is obtained. Buy now and enjoy the lovely customers that frequent this Subway -- business starts picking up now until end of October. Make your offer today!

1216 S Talbot Street Unit #A AND B, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

3 Beds 3 Baths
Located in the heart of St. Michaels' Historic District, the "Keithley House," circa 1786, is one of the town's historic treasures. Records indicate the house was renovated and expanded between 1860 and 1870, when Victorian elements were incorporated, including a wonderful front porch. The house was extensively restored and updated in 2008, with care to preserve the 18th and 19th century charm. Most of the heart-pine floors, center hall stairs, sawn balusters, newel post and banister are believed to be original. This is a very livable house. The downstairs plan includes a comfortable living room w/fireplace; sitting room w/fireplace; dining room; modern kitchen; powder room and laundry area. Upstairs features three bedrooms (one w/fireplace) and two full baths. The house is sited on one of the larger lots and highest elevations in town. Beautifully landscaped, private back yard, with potential to add a swimming pool and/or carriage house (subject to Historic Commission approval). Premier location, near fine dining, Chesapeake Bay Museum and the Harbor.

104 Mulberry St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

8 Beds 9 Baths
Spectacular and Successful 7 Bedroom/7.5 bath waterfront residence located on one of St. Michael's most desirable locations. The renovations, design and craftsmanship leave no stone unturned. Recent renovations and improvements include roof, windows, electric and plumbing, wood siding, main sewer line, commercial grade appliances, kitchen cabinets, 3 propane commercial water on demand units and insulation. Each bedroom has its own marble bathroom. Conveniently located in the heart of St. Michaels allows one to enjoy all of the historic town's attractions, restaurants , marinas and shops. Additional features include dock , patio, and decks. There appears to be plenty of room for a waterside in-ground pool. * This magnificent property is currently being operated as a licensed Bed and Breakfast but can easily be converted back into a beautiful single - family residence.

202 Cherry St, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 673-3344

3 Beds 4 Baths
Back on the market, this is your opportunity! Contract fell through because of previous buyers construction plans .This completely remodeled, one level exquisite home with guest cottage in historic St. Michaels exudes timeless sophistication. The main house has 2 bedrooms and 2 1/2 baths, the detached guest cottage has one bedroom upstairs and an open floorplan with a full bath downstairs. With park like landscaping this property is 2 houses from the St. Michaels Nature Trail and the new site for a waterfront town park on San Domingo Creek. Walk to your kayak at Chew St. Park. Relax on your front porch swing because there is nothing that needs to be done! Tongue and groove southern yellow pine wood floors throughout , vaulted exposed beam ceilings, gourmet kitchen with leathered granite counters and custom oak cabinetry, eat-in bar, SS appliances, gas stove and much more! This home has plenty of natural light, with numerous skylights and windows in the living room looking out to the front porch. The generously sized primary bedroom has 2 walk in closets and a beautifully updated full bath as well as sliding doors to a private deck. This property also has a driveway that leads to a 1 car garage attached to the guest cottage. The guest cottage/studio has the same wood flooring, vaulted ceilings and a beautiful full bath. The upstairs carpeted loft has room for a king size bed as well as office space . Both dwellings have on demand hot water heating systems. Start your new year with this unique opportunity to step back in time and live the good life on Maryland's eastern shore ! Slow down the pace and walk to shopping and restaurants in quaint , historic St. Michaels.

107 W Maple Ave, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

3 Beds 3 Baths
Located in Martingham, home of the newly redesigned Pete Dye golf course, The Links at Perry Cabin. This 3BR/2.5BA Colonial style home is situated on an open 1.13ac lot with a tree lined backyard for privacy. Inside you will enjoy a spacious floor plan, and updated island kitchen, and a large family room highlighted by a wood burning fireplace and a beam ceiling. Upstairs you will find the generously sized primary bedroom with a private balcony overlooking the backyard, and the two additional oversized bedrooms. Entertaining will be a breeze with a sizeable deck, leading to the fire pit and expansive level backyard. Don't miss this opportunity to live minutes from historic St. Michaels with all of its wonderful restaurants and shops.

24749 Swan Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

4 Beds 3 Baths
Charming 4-Bedroom Home with Guest Cottage in Saint Michaels, MD Nestled in the picturesque town of Saint Michaels, this enchanting property offers a unique blend of classic charm and modern comfort. The main residence features four bedrooms, providing ample space for families or those seeking room to grow. With meticulous attention to detail, the interior boasts tasteful design elements, creating a warm and inviting atmosphere. The property's allure is further enhanced by a separate guest cottage, offering versatility for accommodating visitors, creating a home office, or exploring rental potential. The guest cottage provides an additional layer of privacy and convenience. Set against the backdrop of Saint Michaels' scenic surroundings, this residence is a haven for those who appreciate both tranquility and community. Whether enjoying the spacious interiors, the charm of the guest cottage, or the vibrant local amenities, this property epitomizes the Eastern Shore lifestyle. Immerse yourself in the historic allure of Saint Michaels while relishing the comfort and space provided by this thoughtfully designed 4-bedroom home with a guest cottage – a true gem in this coveted Maryland town.

602 S Talbot St, Saint Michaels

Listing courtesy of TTR Sotheby's International Realty. Contact: