St. Michaels Real Estate

St. Michaels Real Estate

Welcome to St. Michaels, a picturesque waterfront community nestled in the heart of Talbot County, Maryland. Known for its charming small-town atmosphere and rich maritime heritage, St. Michaels is a hidden gem on the Eastern Shore that offers a unique blend of history, culture, and natural beauty.

As you stroll through the tree-lined streets, you’ll be captivated by the quaint boutiques, art galleries, and delightful eateries that line the historic downtown area. The town's vibrant arts scene and annual events, such as the St. Michaels Wine Festival and the Maritime Museum's summer concerts, draw both locals and visitors alike, fostering a tight-knit community spirit.

St. Michaels is also a haven for outdoor enthusiasts. With its stunning waterfront views, residents can enjoy sailing, kayaking, and fishing on the Chesapeake Bay. The nearby parks and nature preserves offer ample opportunities for hiking and birdwatching, making it easy to connect with the region's natural beauty.

For families, St. Michaels boasts top-rated schools and a safe, welcoming environment. The subdivision features a variety of housing options, from charming historic homes to modern waterfront properties, catering to diverse lifestyles and budgets.

Whether you're looking for a peaceful retreat or an active community, St. Michaels offers the perfect blend of tranquility and excitement. Experience the charm of this delightful town and discover why so many choose to call St. Michaels home. Come explore the possibilities and start your next chapter in this enchanting community!

Newest Listings in St. Michaels

Commercial Opportunity– Positioned along S. Talbot Street (Route 33) at the entrance to St. Michaels, this General Commercial (GC) property offers exceptional visibility, convenient access, ample parking, and a flexible three-unit configuration suitable for a variety of commercial uses. The property provides a strong location for an owner-user or investment opportunity with easy access to St. Michaels, Easton, and surrounding Talbot County communities. Previously recorded as a muli-unit commercial condominium regime, dissolved in 2019. Unit A– 248' of Road frontage / Showroom Approximately 4,044± SF One-story block construction with storage attic Large display windows Showroom space Office and planning areas Shop and storage areas Central air conditioning 2-zones 10'x8' door Unit B– Warehouse / Flex Space (Heated) Approximately 4,148± SF Metal building Warehouse/light industrial configuration Two 12' × 12' drive-in doors Flexible warehouse and storage space 2nd Floor storage space added Loading and service access Unit C– Workshop / Storage Additional detached commercial unit offering workshop and storage flexibility. Potential Uses– The property's General Commercial zoning and flexible layout make it well suited for a variety of commercial applications, including: Retail Professional office Showroom Automotive/service business Warehouse Marine Businesses Distribution Flex commercial Contractor headquarters Storage Light industrial Investment opportunity Owner-user occupancy

1007 S Talbot St, Saint Michaels

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

4 Beds ⋅ 3 Baths

Just 4 miles (five minutes) outside the historic town of St. Michaels, MD, this 15-acre property is located in an area of large, private waterfront estates. Over 400 ft. of protected shoreline. Westerly exposure provides Exceptional Sunset Views across the sparkling waters of Harris Creek! 120' x 6' pile-driven pier provides approximately 4' MLW. Sited near the water at the end of a long, tree-lined driveway, you will find an attractive Dutch Colonial-style home. Constructed in 1966, the house features 4 bedrooms (primary downstairs); 2.5 bathrooms; spacious kitchen/dining/family room w/fireplace; formal living room w/fireplace and a glassed waterside "River Room." The 2-zone HVAC system was replaced with new, efficient system(s) in 2024. The house is dated, but perfectly livable. Some new owners will decide to update. Others might decide to demolish and replace with a new home. The 15-acre site and prime location will support a very substantial home. This is a great boating/fishing/crabbing location. Tilghman Island, with its marinas and waterside restaurants, is just a short, scenic boat ride down Harris Creek from the substantial private dock. The open waters of the Choptank River and Chesapeake Bay are just beyond Tilghman Island.

9020 Bozman Neavitt Rd, Saint Michaels

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

2 Beds ⋅ 1 Baths

Priced to sell! The perfect weekend getaway does exist—and it's more attainable than you might think. Escape the city and discover the charm of St. Michaels, one of the Eastern Shore's most beloved waterfront towns. Known for its picturesque streets, waterfront dining, boutique shopping, wineries, marinas, and laid-back coastal lifestyle, St. Michaels offers the perfect place to relax, recharge, and enjoy a slower pace of life. Welcome to 204 E Marengo Street—an affordable opportunity to own a move-in ready home just outside of the Historic District and approximately 1.5 blocks from water access, including a marina and public boat ramp. Whether you're looking for a weekend retreat, second home, or a place to enjoy extended stays on the Shore, this charming cottage offers the ideal blend of comfort, convenience, and location. Inside, you'll find bright, inviting living spaces, easy main-level living, an updated bathroom, modern HVAC, and numerous recent improvements. Major updates include a new roof (2024), upgraded crawl space with French drain, insulation, and vapor barrier (2025), updated plumbing (2025), Thompson Creek windows, HVAC and water heater (2018), plus updated appliances and plantation shutters—allowing you to move in and start enjoying the St. Michaels lifestyle immediately. Outside, your private backyard oasis awaits. Enjoy summer days by the in-ground pool, entertain at the beach-inspired outdoor bar with cable TV, or unwind after a day on the water. The detached garage with electric provides additional storage, workspace, or future possibilities. Unlike many properties in town, this home is located outside the Historic District, offering greater flexibility for future updates and improvements without Historic District oversight. Leave the traffic and stress behind and spend your weekends where others vacation. Walk to restaurants, coffee shops, boutiques, museums, waterfront parks, and marinas while enjoying one of the Eastern Shore's most sought-after destinations.

204 E Marengo St, Saint Michaels

Listing courtesy of Compass. Contact: (410) 429-7425

4 Beds ⋅ 3 Baths

This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area and well-appointed kitchen, featuring a gas stove and stainless steel appliances. Practical amenities include a mudroom with laundry just off the attached two-car garage, a Rinnai tankless water heater, and an efficient dual-zone heat pump system with separate upstairs and downstairs climate controls. The second floor offers additional flexibility with a bedroom, full bathroom, and a large family room—perfect for guests, a home office, media room, or recreation space. Just off the recreation room, a spacious attic provides abundant storage and offers potential for future expansion. Outside, enjoy a beautifully landscaped backyard featuring a stone patio and ample garden space, creating the perfect setting for outdoor dining, gardening, or simply enjoying the peaceful surroundings. Ideally situated in the heart of St. Michaels, this home offers exceptional proximity to the area's most beloved destinations. Located less than 200 feet from the St. Michaels Nature Trail, just 0.2 miles from Chew Street Park, and only 0.2 miles from historic downtown St. Michaels, you'll enjoy convenient access to shopping, dining, waterfront attractions, and community events. Adding to the appeal, plans are underway for the future San Domingo Creek Park at the end of W Marengo Street—a proposed 7.6-acre waterfront park focused on recreation, environmental restoration, and trail connectivity that is anticipated to become the largest waterfront park in St. Michaels. Exceptional proximity to downtown St. Michaels, future recreational amenities, modern comforts, and versatile living spaces make this home a rare opportunity in one of the Eastern Shore's most sought-after communities.

109 W Marengo St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

3 Beds ⋅ 3 Baths

***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze accessories, artisan wood range hood, spacious center island w/breakfast bar, high end d'oro quartz countertops and herringbone tile backsplash. The living room includes a gas fireplace w/shiplap surround, custom coffered ceiling, large picture windows and a four panel Pella slider door which allows abundance of natural light and direct access to the backyard. Rounding out the main level is a flexible multi-purpose space - perfect for a formal dining room, office or a sitting room. On the upper level enjoy 3 bedrooms and two baths, including an owner's suite with walk-in closet and a luxurious spa-like bath with dual vanities, rich blue cabinetry and walk-in shower with dual shower heads and floor-to-ceiling attache calacatta tile. Additional amenities include LVP flooring throughout main level, ceramic or porcelain tile in all baths, custom light fixtures, public water and sewer, 30 year architectural singles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, covered front porch and much more. All of this in a convenient location adjacent to all historic Saint Michaels has to offer. Loaded with amenities and unbound by an HOA or restrictive covenants, this one of a kind property will not last long! Schedule your private tour today!

807 Radcliff Ave, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010

3 Beds ⋅ 3 Baths

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

303 Manor, Saint Michaels

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

4 Beds ⋅ 3 Baths

Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

101 Mulberry St, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

5 Beds ⋅ 5 Baths

UNIQUE PROPERTY RIGHT OUTSIDE OF HISTORIC ST MICHAELS TOWN LIMITS ACROSS THE LINK AT PERRY CABIN. THIS FABULOUS HOME OFFERS SPACE FOR GATHERINGS WITH FAMILY OR FRIENDS BUT ALSO FEELS COZY FOR EMPTY NESTERS THAT LOVE TO ENTERTAIN. THERE ARE NO RESTRICTIONS THAT PROHIBIT VACATION RENTAL, THERE SHOULD BE SPACE FOR AN INGROUND POOL . ORIGINALLY BUILD IN 1973 THE CURRENT OWNER GUTTED THE HOME, ALL SYSTEMS, ELECTRICAL, WINDOWS, FLOORS ETC ARE NEW- JUST MOVE IN AND ENJOY. FROM NATURAL OAK FLOORS TO MARBLE BATHROOMS, WHITE SPACIOUS KITCHEN WITH GLEAMING GRANITE AND SOAP STONE COUNTERTOPS. EXTENSIVE OUTDOOR LIGHTENING , SPEAKERS, LIGHTENING UNDER THE EVES TURN THIS INTO A MAGICAL PLACE IN THE EVENING. GATHER BY THE HUGE FIREPIT AND ENJOY OUTDOOR LIVING , COOKING AND DINING ON THE VARIOUS PATIOS OR WRAP AROUND DECK. MAINTENANCE EASY MATERIALS HAVE BEEN USED FOR THE DECKING, SIDING AND ROOFING, ATTENTION WAS PAID TO GUTTER SYSTEMS AND GRADING. THE DRIVEWAY IS FRAMED BY BELGIAN COBBLESTONE, STONE COLUMNS GREET YOU WHEN YOU ENTER THE PROPERTY. THIS IS A RARE OPPORTUNITY FOR A TURN KEY PROPERTY IN ST MICHAELS WITHOUT THE TOWN PROPERTY TAXES AND RESTRICTIONS.

9180 Saint Michaels, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

3 Beds ⋅ 3 Baths

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 Shore’s 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.

108 Miles Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

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, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com

4 Beds ⋅ 3 Baths

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.

Lot 16A Meadow St, Saint Michaels

Listing courtesy of Keller Williams Flagship. Contact:

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