Saint Michaels Real Estate | Saint Michaels Properties for Sale

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

$399,900

2 Beds ⋅ 3 Baths

Nestled in the desirable Martingham community and backing to the scenic 2nd hole at the Links of Perry Cabin, this charming 2-bedroom, 2.5-bathroom condo offers a perfect retreat for low-maintenance living. The open living and dining area, featuring a cozy wood-burning fireplace, flows seamlessly into the inviting sunroom, creating the ideal space for relaxation. The primary bedroom boasts a private balcony overlooking serene views, while both bedrooms offer en-suite bathrooms for added comfort. A detached one-car garage provides convenience, and the property is just minutes from historic downtown St. Michaels, known for its quaint shops, restaurants, and marina. Whether you’re seeking a weekend getaway or year-round living, this condo is a peaceful escape with easy access to all the charm St. Michaels has to offer.

9539 Quail Hollow Unit #302, Saint Michaels

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

$425,000

Well established restaurant in the Busy Easton Marketplace Shopping Center. Strong track record with a well known location and product. All furniture fixtures and equipment convey.

1013 S Talbot St, Saint Michaels

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

$1,989,500

4 Beds ⋅ 4 Baths

Experience casual elegance in this newly renovated, single-level home, thoughtfully designed for family, friends, and entertainment. Situated on the largest corner lot in town, this home boasts 250 feet of water view frontage, offering breathtaking sunset views. Surrounded by mature trees and a rare second lot, the property ensures privacy and a connection to nature, and the potential for further subdivision. The split floorplan includes 4 bedrooms and 4 full baths, with three en-suite options for added comfort. The large four-season sanctuary room, equipped with a stand-alone HVAC system, provides a perfect retreat to enjoy outdoor living year-round. The eat-in kitchen features island bar seating, while the living room offers a cozy wood-burning fireplace. The dining and family room, with its vaulted ceiling, presents stunning water views from every angle. This fully furnished, renovated brick home embodies the owner's vision of maintenance-free living—transforming the dream of effortless ownership into a reality. Embrace the charm of Eastern Shore living with all the conveniences of being in-town on the harbor.

501 W Harbor Rd W, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$189,000

Ready to build your custom home in the beautiful town of St. Michaels! This is a larger lot, over 1/5 of an acre. Enjoy all the benefits of living in town, walk to the harbor, shops, restaurants, nature trail, library, ball park, community center and Chesapeake Bay Maritime Museum. There is existing water and sewer hook-up. Verified there are no hook-up fees. Lot offers garage in good condition. Buyer/Builder must conduct their own due diligence. Must confirm buildable square footage, setbacks, etc. See document section for more details and/or contact listing agent.

226 North St, Saint Michaels

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

$329,000

2 Beds ⋅ 2 Baths

There is a wonderful community lot with a Gazebo overlooking the Miles River for you and your invitees to take advantage of. This Bright and Airy single-story unit with wide Halls and no steps to enter from large parking area with rear views overlooking the Perry Cabin golf Corse #6. A Freshly painted interior using Bengerman Moor Ultra Paint. Spacious great room with gas fireplace wide halls to bedrooms each with an attached full bath. Prices to sell so make your appointment today. Start enjoying this one-story cottage and life on the eastern shore in the land of pleasant living with-out delay. Here the exterior has been restored interior has been painted and is a spacious unit. New storm doors on the main entrance and for the Kitchen entry.

24560 Deep Water Point Drive Unit #4 - GULLWING VILLAS, Saint Michaels

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

$524,900

3 Beds ⋅ 3 Baths

Welcome to this stunning 3-Bedroom, 2.5 Bath home nestled in a tranquil, private cul-de-sac in a charming St. Michaels neighborhood. Be dazzled by the 30 foot vaulted ceiling, loft overlook and wood burning Fireplace. This beautifully maintained residence boasts an inviting open floor plan, the perfect ambiance for relaxation. The modern kitchen has been expertly remodeled with upgrades and features a convenient breakfast bar. The first floor Primary Ensuite bedroom offers a private retreat, while the first-floor laundry adds practical convenience. The owners have beautifully and completely remodeled all the bathrooms. Step outside to enjoy the newly painted and updated Backyard Deck and Brick Entertainment Patio, ideal for hosting gatherings, or simply unwinding in your serene, fully fenced yard. The property is professionally landscaped with beautiful French Gardens and Walking Paths and overground irrigation, all enhancing its curb appeal, and includes and "almost new" attached garage for added storage and convenience and a cute Backyard Shed for storage. Last but certainly not least, the crawl space has been fully encapsulated. This home seamlessly combines style, comfort and functionality in a picturesque setting all just minutes from downtown St. Michaels. This is an opportunity not to be missed!

25070 Hurley Ln, Saint Michaels

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

$99,000

Nice buildable lot in an up & coming neighborhood in St. Michaels! Town services, public water & sewer hookup available. Walk to Rails & Trails, ballpark, library, town center, waterfront. Close to Community Center, daycare & schools. Build your custom home in this beautiful, waterfront, historic town! Builder must conduct their own due diligence, verification, research, and inspections of lot to verify land use. Open to offers.

Brooks Lane, Saint Michaels

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

$659,900

3 Beds ⋅ 3 Baths

OPEN HOUSE THIS SATURDAY, SEPTEMBER 14TH FROM 12 PM - 2 PM AND SUNDAY, SEPTEMBER 15TH FROM 12 PM - 2 PM! COME FOR LUNCH AND A DETAILED TOUR OF THIS GORGEOUS HOME! AS WELL, THE LATEST INFORMATION ON MORTGAGE RATES AS THEY ARE EXPECTED TO DROP AFTER SEPTEMBER 18TH. 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:

$435,000

3 Beds ⋅ 2 Baths

Welcome to this charming 3-bedroom, 1.5-bathroom rancher located in the heart of Historical St. Michaels, MD. This home is conveniently situated just minutes from local shops, dining, and attractions, with the added benefit of being in close proximity to the local school. This well-maintained residence offers a blend of comfort and convenience, perfect for families or investors. Recent updates include a gas water heater installed in May 2023, a new roof added in May 2019, gutters replaced in 2020, and an AC and heat panel updated in May 2020. Additionally, the home has had annual pest control and features a fenced-in backyard, ideal for outdoor activities and privacy. This home presents a great opportunity for rental income. Call to schedule your private tour today!

107 E Maple Ave, Saint Michaels

Listing courtesy of Keller Williams Select Realtors. Contact: (410) 972-4000

$399,000

2 Beds ⋅ 1 Baths

This low-maintenance two-bedroom cottage, located across from the Inn at Perry Cabin at the corner of Talbot and Lee Streets, has been fully renovated with luxury vinyl plank flooring, board & batten siding, updated fixtures, recessed lighting, crown molding, tile shower surround, and a front-loading washer/dryer. It's ideal for a weekend retreat or as an investment property. The landscaping has been recently refreshed with a white gravel driveway and a new underground downspout stormwater management system that draws water and moisture away from the house, along with a new shed. The brand-new roof was installed with F-WAVE REVIA Synthetic roofing shingles!

100 Lee St, Saint Michaels

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

$1,900,000

One of a kind beautifully maintained building in St. Michaels, Renovated and enlarged in 2002 . First floor offers 4 office suites, workroom, conference room, 2 bathrooms and kitchen/break room. ADA compliant Second floor has 2 separate outside entrances , multiple offices, conference area, and 2 bathrooms. There is paved parking for 30+cars. Designed by Christine Dayton and built by Peter Hanlon, CG zoning offers many possibilities like Healthcare, medical, dental, private offices , convenience store, food services, Day Care, Church, Government offices, etc. Buyers to confirm with Talbot County Planning & Zoning regarding the permitted uses.

1103 S Talbot St, Saint Michaels

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

$869,000

Fantastic TRAFFIC COUNT on this prime corner location at the entrance to Saint Michaels. This is NOT within the Town limits. See agent for list of permitted uses or contact Talbot Planning & Zoning. Building has a drive in facility or it can be enclosed for additional square footage. Tax records indicate the building is 1,566 sq. ft. with a finished 2nd floor. Plat available. Building was a bank for many years and at one time a convivence store. Currently unoccupied but in excellent condition with access to Talbot and Lincoln. Property has municipal sewer.

1101 S Talbot St, Saint Michaels

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

$4,500,000

5 Beds ⋅ 6 Baths

Inspired by the architecture of the French West Indies, this unique 9,334 +/- square foot waterfront retreat features five octagonal wings linked together, offering stunning panoramic views of the Miles River from nearly every room. Step into the luxurious interiors of Rivermark and you'll find yourself immersed in a world of exquisite craftsmanship and timeless elegance. Every detail has been meticulously crafted, from the hand-carved cabinets to the gleaming cherry hardwood floors. The focal point of this magnificent home is the distinguished living room, boasting soaring ceilings that create an atmosphere of grandeur. From the living room, step into the sunroom, where travertine floors and walls of windows wrap around the interconnected spaces of the sunroom, dining room, and kitchen, providing panoramic views of the serene Miles River. Entertaining guests is effortless in the well-appointed kitchen, featuring an Aga stove, granite countertops, and floor-to-ceiling cabinets. Off of the kitchen, the primary suite welcomes you with 18 ft ceilings and en-suite bathroom. For production, Rivermark offers two office spaces with floor to ceiling built-ins and hardwood flooring. On the opposite wing of the home, you'll discover two additional bedrooms adorned with intricate finishes and a shared bathroom. One of the unique features of Rivermark is the octagonal wing housing a hotel-style swimming pool, complete with a sauna room, full bath, and adjacent greenhouse. A separate guest wing provides privacy with its own entrance, offering two bedrooms, two bathrooms, a kitchen, and a comfortable living space. The grounds lends itself to a new level of respite that entails a serene koi pond with a fountain and extensive landscaping. Savor days on the Eastern Shore’s waterways with your private 150 ft dock and boat lift for ease of access to local restaurants or relaxing boat rides. With all of these amenities in mind, plus much more, Rivermark is the perfect home for public entertaining and private relaxation alike. Settlement not to occur before 9/30/2024.

9791 Pintail Pl, Saint Michaels

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

$475,000

4 Beds ⋅ 3 Baths

Welcome to this updated ranch-style home in the water-privileged community of Rio Vista. Nestled near downtown St. Michaels, this charming residence offers access to a community marina and boat ramp on Spencer Creek and park with picnic area on the scenic Miles River. Enjoy the convenience of local shops and waterfront dining just moments away. The home’s exterior boasts a covered front porch and new landscaping, creating a welcoming curb appeal. Step inside to find a spacious living room with beautiful laminate plank flooring and a neutral paint color that flows throughout the house. The kitchen features 42-inch beadboard cabinetry, granite counters, and stainless steel appliances, perfect for culinary enthusiasts. Designed with a split bedroom floor plan, the primary bedroom at the back of the home provides a private retreat with a renovated en-suite bath, showcasing a seamless entry floor-to-ceiling tiled shower with grab bars. On the opposite side of the home, another bedroom with an en-suite bath and two additional bedrooms sharing a full hall bath offer ample space for family and guests. Additional features include a crawl space encapsulated in 2016, a back half roof replacement in 2023, and a floored attic with pull-down stairs for extra storage. The resurfaced deck overlooks a serene backyard with mature trees and a storage shed, providing a peaceful outdoor escape. A ramp off the driveway connects to the deck, offering side door access into the home for added convenience. Experience stylish living in a vibrant community with this beautifully renovated home in Rio Vista. Property Updates: stove, dishwasher & microwave, interior paint, flooring, deck resurfaced, back half roof replacement, landscaping, full bath renovated, and crawl space encapsulated.

1110 Jefferson Ave, Saint Michaels

Listing courtesy of Northrop Realty. Contact: (410) 295-6579

$2,249,900

3 Beds ⋅ 4 Baths

Nestled among the serene loblolly pines, this exquisite 4+/- acre waterfront lot offers an unparalleled retreat overlooking the tranquil waters of Broad Creek. Take a front row seat to colorful sunsets year-round thanks to the south-westerly views. Former Church Neck Road adjacent neighbor, James Michener, undoubtedly drew inspiration from similar water views for his novel ‘Chesapeake’, enriching the legacy of this storied locale. Step inside to discover a sanctuary of serenity, where water views greet you from nearly every room on the main level. From the comfort of the primary suite to the warmth of the living room, complete with a wood-burning fireplace, and the inviting ambiance of the dining room, and the sun-drenched charm of the kitchen's sunroom, each space invites you to unwind and soak in the natural beauty that surrounds you. The living room boasts vaulted ceilings, drawing your gaze upward to accentuate the sense of space and airiness. Upstairs, two bedrooms and a library office offer a bird's-eye view of the main living area below. Meanwhile, above the garage, an additional bonus two room office/study space await, complete with a full bathroom, ready to adapt to your every need. Outside, a 2-car garage stands ready to accommodate your vehicles or storage, while a waterside stone patio provides the perfect spot to bask in the gentle rhythms of the rip-rapped shoreline. Experience the magic of waterfront living and prevailing southwesterly breeze in this idyllic retreat, where every moment is infused with the timeless beauty of the Chesapeake Bay.

7930 Church Neck Rd, Saint Michaels

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

$1,795,000

3 Beds ⋅ 3 Baths

This substantial brick home with gorgeous sunset views across Harris Creek is a private retreat just five miles from St. Michaels' shops and restaurants. Sited on 4.7 mostly-wooded acres, the home features a first floor primary suite with waterside sitting area, a family room with woodburning fireplace and a striking stone accent wall, dining room, spacious eat-in kitchen, den and screened porch. Upstairs are two bedrooms with a Jack and Jill bath. There is an attached, oversized two-car garage and a detached heated and air conditioned office with built-in bookshelves - the perfect office or studio. Built in 1998 with steel framing and oversized brick, this house feels solid. It is well elevated, in the preferred low flood risk "X-Zone." The panoramic views are exceptional! Substantial 5' x 150' dock. Over 200' of protected shoreline.

8288 Bozman Neavitt Rd, Saint Michaels

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

$750,000

3 Beds ⋅ 2 Baths

Tranquility meets beauty in this completely renovated historic property only steps to the waterfront park & a block into town! This beautiful home has been renovated from top to bottom & has been designed to offer style & coastal feel all while retaining it’s historic charm. Featuring a new, lifetime blue metal roof, gardens, patios, & relaxing, covered front porch to watch the world go by. An adorable garden/workshop/art studio shed, & fully fenced back yard with french storm drains complete the exterior amenities. Inside, admire durable new floors & carpets, custom cabinetry, designer colors & finishes throughout. The gorgeous kitchen features all new, modern appliances & granite countertops. The living room has front door opaque glass transoms that radiate light. The main level bedroom can also be used as a den, family room, playroom or office. There's a main level laundry room. 2 bedrooms upstairs share a luxurious, large bathroom & huge walk-in closet. Super low maintenance property! The waterfront park can be seen from the front yard & has kayak racks & floating kayak launch dock. Take a walk along the picturesque walking trail with covered bridge. Use the picnic area & playground all within the park. Then walk a block to the vibrant town of St. Michaels & it’s wonderful restaurants, shops, farmers market, music in the park & festivals. Enjoy watching the yachts rolling into the marina’s & world class sailboat racing. A perfect home away from the hustle & bustle of the rest of the world! High ground, certified lead free & just outside the historic district restrictions. Furnished option available & possible short term owner financing!

204 W Chew Ave, Saint Michaels

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

$950,000

4 Beds ⋅ 3 Baths

Charming home in the heart of Saint Michaels, 3 blocks from the harbor!! REDUCED to 950,000 !!!! This home was completely rebuilt from the ground up in 2021. 4 bedrooms, 3 bath 2400 square-foot home with Open floor plan, 1st floor Primary Suite, modern kitchen, private backyard with patio pavilion. Building Renovation: Interior: Home was stripped to the studs and rebuilt structurally from the foundation up. New kitchen addition and new second-floor added. Crawlspace is encapsulated with two sump pumps and two dehumidifiers. Hardwood hickory floors throughout first floor custom doors and trim package stone faced gas fireplace in great room Exterior: New custom color cement board siding 30 year architectural roof shingles. Anderson Vinyl Windows throughout Composite decking on front porch Bluestone paver patio overlooking back yard and pavilion patio custom landscape package and cedar privacy fence. Highly energy efficient construction including air seal, spray foam & batt insulation All New Systems in the home including: New 200 amp electric service run underground to grid. All new electrical wiring and devices. LED recessed lights throughout. CAT5 and coax Internet/cable wiring in all bedrooms and living rooms. New plumbing waste and waterlines with all new fixtures. High efficiency five zone central air/heat pump. Propane on demand hot water, cooking range, gas grill & fireplace.

109 E. Maple Ave, Saint Michaels

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

$189,500

Build your dream home in Saint Michaels! Only steps away from the YMCA and Saint Michaels school, this lot (approx 75 x 75 ft), situated on the corner of Parsonage and Radcliffe in Bentley Hay, is perfectly located for convenience. Within minutes by foot, you are in the heart of town enjoying the local cuisine and quaint shops. Or take a stroll down the road to enjoy the expansive views of the glorious Miles River. The water meter is set/public hook up available and the sewer lateral is in place/sewer hook up available on this lot. Buyer should confirm all hook ups with the county. There is NO TOWN TAX in this location!

Radcliffe Ave, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4107458060

$9,950,000

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: 4108226272

$9,950,000

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: info@wfp.com

$1,395,000

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 higher elevations in town. Beautifully landscaped, private back yard, with potential to add a swimming pool and/or carriage house (subject to Historic board approval). Private driveway/parking area will accommodate 3 cars. Premier location near St. Michaels Harbor, a variety of great restaurants, Chesapeake Bay Museum and downtown.

104 Mulberry St, Saint Michaels

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

$374,900

Indulge in the allure of Eastern Shore living with this exquisite premium building site, situated in the esteemed Estate area of Oakwood Park. Just a stone's throw from the historic charm of downtown St. Michaels, this parcel offers a serene escape surrounded by nature's beauty. Picture-perfect views of San Domingo Creek adorn this tranquil lot, dotted with mature trees. Anticipate the convenience of public sewer expected by 2024, elevating the appeal of your future dream home. Embrace the opportunity to curate your ideal Eastern Shore retreat in this idyllic setting. All the information you need to know is available on the Talbot County Public Works web site. . Property is marked with stakes.

Oakwood Park Rd E, Saint Michaels

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

$900,000

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:

$1,900,000

Prime and rare opportunity to locate your business on the main entrance to St. Michaels. High visibility, excellent access and plenty of parking. Zoned "General Commercial" with 3 separate buildings totaling over 9,678+/- sf. Possible expansion, no town taxes.

1007 S Talbot St, Saint Michaels

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

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