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2 Beds 2 Baths
Situated on a beautiful spacious corner lot only a block to downtown Historic St. Michaels, this house offers two bedrooms and one and a half baths, charm and comfort. Fenced rear yard with flagstone patio, rear deck storage shed and off-street parking. Beautiful wood flooring, open living / dining area, wood stove insert in fireplace, updated kitchen and main level laundry/mud room. Zoned Central Commercial, possible commercial on first floor and short-term rental second floor; renovations would need to be made. There is also room for expansion on this parcel. Property is not in a flood zone. Windows replaced 2009, Shed new 2009, Shingles replaced 2013, new HVAC and encapsulated crawl space w/french drain 2017.

305 Canton St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

4 Beds 4 Baths
This gorgeous St. Michael's waterfront home is located in the popular sought-after community of Bentley Hay only minutes to historic downtown St. Michael's. Sited on a double lot, this four bedroom custom built home offers broad views of the Miles River, a protected shoreline, pier with 20k lb boat lift, waterside deck and beautiful waterside screened porch with tile flooring and custom wood ceiling with fan. Inside offers incredible water views from almost all rooms, a spacious great room with cathedral ceiling, wet bar, large open kitchen with center island and waterside dining area. The waterside first floor owner's suite has a luxurious bathroom, WIC, custom built-ins and private office/bonus room. Main level laundry room with ample storage. The second floor has a sitting room, guest bedroom, full bathroom and tons of walk in attic storage. Oversized garage with additional storage space. Don't miss this gorgeous home! Jet ski lift and refrigerator go as-is.

705 Riverview Ter, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

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

7 Beds 6 Baths
Welcome to your dream waterfront retreat! ​This custom-built masterpiece is a true gem, ​boasting unparalleled elegance and ​luxurious features. With 7 bedrooms and 5.5 ​bathrooms, this residence offers the perfect ​blend of comfort and sophistication. As you step inside, you'll be greeted by ​ample natural light that floods through the ​large windows, creating a warm and inviting ​atmosphere throughout the home. The ​cathedral-ceiling dining and living rooms add ​an extra touch of grandeur, providing a ​spacious and airy feel that is perfect for ​both entertaining and everyday living. First floor primary suite with water views, custom walk-in closet, and a luxurious bath with heated floors, ​double vanities, relaxing jetted tub and beautifully tiled steam shower. The hardwood flooring adds a ​timeless and classic touch to the interior, complementing the high-end finishes and attention to detail that ​is evident in every corner of the home. The gourmet kitchen is a chef's delight, featuring stainless steel ​appliances and custom cabinetry. For those who appreciate the finer things in life, this property also includes a detached 3-car garage with ​a 2-bedroom guest apartment, offering versatility and additional space for hosting friends and family. ​Imagine the convenience and luxury of having a separate space for guests to enjoy their privacy. Step ​outside, and you'll discover the guest cottage, a charming retreat overlooking the serene waterfront. ​With its own unique character, this cottage provides an ideal spot for guests or even a private home ​office. The waterfront experience is taken to the next level with 250'+/- of rip-rapped shoreline, a private pier ​and boat lift. Whether you're an avid boater or simply enjoy the tranquil views of the water, this property ​offers the perfect setting to savor the beauty of waterfront living. Spend your days basking in the sun on ​your waterside deck, relaxing in your Swimspa, fishing off the pier, or taking a boat ride to explore the ​nearby waterways. Immerse yourself in the beauty of nature and create lasting memories in a home that ​truly reflects your discerning taste. Don't miss the opportunity to make this gorgeous waterfront property ​your own!

24756 Rays Point Rd, Saint Michaels

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

3 Beds 4 Baths
Slow down the pace and walk to shopping and restaurants in quaint , historic St. Michaels. This completely remodeled, one level exquisite home with guest cottage in historic St. Michaels exudes timeless sophistication. 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 !

107 W Maple Ave, Saint Michaels

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

4 Beds 3 Baths
Discover the allure of Historic St Michaels, a captivating town nestled on Maryland's Eastern Shore, boasting a harmonious blend of vibrant marinas, delectable dining, and unique boutiques. Seize the extraordinary chance to make this exquisite home yours. Nestled on a tranquil street adorned with distinctive cottages and friendly neighbors, this residence, meticulously maintained by its original owners, emanates a timeless charm that feels as fresh as the day it was built. Approach the property and appreciate the hand-selected pavers forming a 2-car wide driveway leading to a spacious garage, ensuring ample parking space. Inside, revel in the open ambiance created by 9-foot ceilings and walls of windows that bathe the space in natural light. The main level showcases three bedrooms and two full baths, complemented by a delightful English courtyard at the rear of the home. Immerse yourself in the warmth of rich hardwood flooring that graces every level. The heart of the home, a gourmet kitchen, beckons with stainless steel appliances, granite countertops, and a charming farm sink, providing an ideal setting for culinary creations. Elegant dining room where timeless sophistication meets modern comfort. Bathed in soft, ambient lighting, the space exudes a warm and inviting atmosphere, creating the perfect setting for memorable gatherings. The large family room, complete with a cozy gas fireplace, offers a perfect retreat for relaxation. The primary suite beckons with a generous walk-in closet featuring custom built-ins and a spa-inspired bath. Each bedroom is generously sized with ample closet space, ensuring comfort for all. The highly convenient mudroom, where practicality meets style to create an efficient space that effortlessly handles the transition from the outdoors to the indoors. Ascend to the second level, where a spacious lounging room, a private bedroom, and another full bath await—a true haven for tranquility and privacy. Embark on a brief stroll along the street to reach Chew Street Park. You'll be delighted by its offerings! Explore a fantastic walking trail and discover a convenient boat ramp. Launch your kayaks directly into San Domingo Creek, savor a picnic, and relish the refreshing outdoor experience. Embrace the enchantment of St Michaels just in time for cherished holiday dreams and memories. Convenient in town location where you can walk to everything you need! Don't miss this rare opportunity to call this meticulously crafted residence your home in the heart of a town brimming with history and charm.

109 W Marengo St, Saint Michaels

Listing courtesy of Coldwell Banker Realty. Contact: (410) 263-8686

4 Beds 5 Baths
Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring a spa-like bath with heated floors, a large soaking tub and separate shower, and two walk-in closets. The kitchen is a chef’s dream, featuring high-end stainless-steel appliances, a wine cooler, a warming drawer, and a massive island. There are also formal living and dining rooms, two office spaces, a recreation room, and a river room that enjoys views of Eastern Bay and beyond. The park-like lot has 220+/- feet of rip-rapped shoreline, a private pier with 3’ of MLW, lush landscaping, and a waterside deck with an outdoor kitchen.

24678 New Post Rd, Saint Michaels

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

4 Beds 2 Baths
Nestled in the heart of historic downtown St. Michaels, this versatile property is a rare find. Originally designed as a duplex with separately metered electric, this unique property is zoned central commercial offering an array of possibilities. Whether you desire a single family residence, a short-term rental, a commercial space, or a unique combination of both, this property can adapt to your needs. Sitting on a double lot, there's the potential for further expansion. You can explore options of a lot line revision, the sale of the additional lot, or the construction of a second residence. The first floor boasts a spacious living room, a kitchen with a dining area and french doors that lead to a welcoming deck, a fenced rear yard and a storage shed/studio. Additionally, a mud/laundry room provides convenient side door access to the blacktop driveway. Two bedrooms and an updated bathroom complete the first floor. The second floor you'll find two to three bedrooms. The primary suite can easily be converted back into a living room and kitchen, transforming it back into a second-floor apartment. With its central location and adaptability, this property is a canvas for your imagination and a unique opportunity in the heart of St. Michaels.

112 Conner St, Saint Michaels

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

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

6 Beds 11 Baths
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 sq.ft. 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. Set within the pine grove is a putting green w/ chipping area & e

8620 Bozman Neavitt Rd, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact:

4 Beds 3 Baths
Priced to sell! Be the first to move into this attractive new construction in the desirable community St. Michaels Pointe at Perry Cabin. This Coastal style 2 story home is the last one available. The beautiful front elevation features an upper and lower deck, the rear is fenced with a patio for outdoor living. With 9ft ceilings and an open floor plan concept, the home sparkles with a light and airy feeling. The integrated gourmet kitchen includes granite counters, an island with sink and breakfast bar and stainless-steel appliances. Living and dining areas are clearly defined but flow seamlessly into each other. The floor plan of this home has been redesigned to include a full bath and bedroom on the first floor and the corner lot location allowed for an increase in square footage over similar homes. The spacious owner’s suite is located on the second floor with access to the upper deck overlooking the grounds of the Inn at Perry Cabin, and features a well-appointed bath with soaking tub, double vanity and walk in shower, as well as a large walk-in closet. Two additional bedrooms with full bath complete the upper level. This community of only 14 new homes is directly adjacent to St. Michaels’ Historic District, across from the Maritime Museum and Inn at Perry Cabin properties, and close to the Miles River Yacht Club. The location allows for easy access to all of St. Michaels restaurants, stores and events. Don't miss out on this opportunity to own a brand-new high quality home in St. Michaels just at the edge of the Historic District! The upper deck is accessed from the primary suite and overlooks the grounds of the Inn at Perry Cabin.

312 N Talbot St, Saint Michaels

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