Saint Michaels Real Estate

Saint Michaels Real Estate

Welcome to Saint Michaels, Maryland—a charming waterfront town nestled in the heart of Talbot County on the picturesque Eastern Shore. Known for its rich maritime heritage and stunning natural beauty, Saint Michaels offers a delightful blend of history, culture, and outdoor adventure.

As you stroll through the quaint streets lined with historic homes and boutiques, you’ll discover a vibrant community that celebrates its roots. Originally a shipbuilding hub, the town is now a haven for art enthusiasts and food lovers alike, boasting a variety of galleries, shops, and restaurants that highlight the region's freshest seafood and local produce.

One of the highlights of Saint Michaels is its stunning waterfront, where the Miles River meets the Chesapeake Bay. Whether you’re enjoying a leisurely boat ride, fishing off the docks, or simply soaking in the breathtaking views, the water is a central part of life here. Outdoor enthusiasts will appreciate the abundance of recreational activities available, including kayaking, paddleboarding, and biking along scenic trails.

Saint Michaels is also home to several annual events and festivals that bring the community together, such as the renowned Saint Michaels Wine Festival and the charming Christmas in Saint Michaels celebration. With its small-town charm and welcoming atmosphere, Saint Michaels is not just a destination; it’s a place to call home.

Explore the unique real estate opportunities in this idyllic town, where you can find everything from historic homes to modern waterfront properties, and experience the enchanting lifestyle that Saint Michaels has to offer. Your dream home awaits!

Newest Listings in Saint Michaels

$1,725,000
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
$600,000
4 Beds ⋅ 3 Baths
NEW PRICE — EXCEPTIONAL VALUE IN DESIRABLE MARTINGHAM! Welcome to 9206 Martingham Drive, a truly distinctive contemporary residence offering spacious living with 4 bedrooms, 2 full and one half bathrooms, abundant natural light, and timeless architectural character in one of Saint Michaels' most sought-after communities. Competitively priced and thoughtfully designed, this unique home features an open floor plan, soaring vaulted ceilings, exposed beams, and expansive east- and west-facing windows that fill the home with natural light while capturing stunning sunrises and sunsets throughout the year. A wood-burning fireplace with a high-efficiency insert and circulating fan creates a warm and inviting focal point, while three dedicated HVAC systems and energy-efficient double-pane windows provide year-round comfort and efficiency. This exceptional property is nestled within the desirable Martingham community, known for its scenic surroundings, golf course lifestyle, and proximity to everything Saint Michaels has to offer. Less than five minutes from downtown Saint Michaels, residents enjoy easy access to waterfront attractions, marinas, boutique shopping, dining, and the very best of Eastern Shore living. The generous living spaces are ideal for both everyday living and entertaining. A spacious two-car garage with built-in shelving provides excellent storage, while the expansive deck—accessible from the sunroom, kitchen, and garage—seamlessly extends the living space outdoors, creating the perfect setting for relaxing or hosting guests. The spacious primary suite on the main floor offers a private retreat, featuring dual walk-in closets and brand-new carpeting installed in 2024. Encapsulated crawlspace for improved moisture control and energy efficiency. Recent capital improvements completed in 2024 include a new roof and gutter system, totaling more than $90,000 in upgrades. Work with our preferred lender to get $2,500 lender credit towards your closing costs! Whether you're searching for a primary residence, a weekend retreat, or an investment opportunity, this one-of-a-kind property delivers exceptional value, space, and location. Don't miss your chance to own a special home in one of Saint Michaels' premier golf course communities.

9206 Martingham Dr, Saint Michaels

Listing courtesy of Samson Properties. Contact: 3017602136
$1,995,000
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
$1,795,000
3 Beds ⋅ 2 Baths
A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact: 4102515291
$549,999
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
$1,049,000
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
$3,495,000
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: 4108226665
$679,000
4 Beds ⋅ 3 Baths
This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth of July fireworks and thirsty Thursday with your new neighbors. Less than 3 miles to downtown St. Michaels Fine Dining and Shopping. MORE PHOTOS TO COME.

24555 Deepwater Point, Saint Michaels

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

$385,000
2 Beds ⋅ 3 Baths
Situated in the established community of Martingham, and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship, energy efficiency, and long-term durability. The redesigned open floor plan creates a seamless flow throughout the main living areas, complemented by updated cabinetry, granite countertops, and stainless steel appliances in the kitchen. All three bathrooms have been refreshed with new vanities, fixtures, and finishes, offering a clean and modern feel throughout the home. Beyond the cosmetic updates, extensive infrastructure improvements provide peace of mind, including a newer HVAC, upgraded electrical panel, full outlet and switch replacement and enhanced attic efficiency with resealing and R49 insulation installation. Interior finishes have been completely reimagined and updated throughout, including new luxury vinyl plank flooring on the upper level and premium Mohawk carpeting with upgraded padding in the lower bedrooms and on the stairwell (2024). Fresh interior paint throughout the home, along with meticulous restoration of original doors - stripped, primed, and repainted with all new hardware installed in 2024 - add to the home's character and detail. Additionally, the deck was also recently primed and painted. Additional improvements include a new washer and dryer (2024), new sliding glass doors in the bedrooms, and a 60-inch Hunter ceiling fan in the great room. A stand out feature of this unit is the expanded floor plan, offering a more open, functional, and spacious living area not commonly found in similar units. The HOA recently completed significant improvements, including a new roof, decking replacements, and new gutters in 2025. Completely turnkey and thoughtfully upgraded make this property ideal as a full-time residence, weekend retreat or investment property.

24700 Deepwater Point Unit #20, Saint Michaels

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

$359,000
2 Beds ⋅ 3 Baths
Escape to the sought-after Swan Road Villa Townhomes, where low-maintenance living meets comfort, convenience, and lifestyle. This bright and inviting reverse-living townhome offers 2 bedrooms, 2.5 baths, and a thoughtfully designed floor plan that appeals to both full-time residents and weekend retreat seekers alike. The upper level serves as the heart of the home, featuring an open-concept layout with a galley kitchen, dining area, and spacious living room. Sliding doors open to a balcony spanning the entire rear of the home, creating the perfect setting for indoor-outdoor living, entertaining, or simply enjoying the abundance of natural light. The main level offers two well-appointed bedrooms, two full baths, and a convenient laundry area. Whether you are seeking a primary residence, second home, first-time purchase, or investment property, this versatile townhome presents an exceptional opportunity. Residents enjoy convenient access to golf (membership available), scenic walking and biking trails, and a nearby waterfront park, all just moments from home. Numerous recent improvements enhance the property's value and appeal, including a new roof, updated bathrooms, new flooring, a new HVAC system, professional landscaping improvements, and fresh interior paint. In addition, the community association is currently completing exterior siding repairs and repainting throughout the community, further enhancing the property's appearance and long-term maintenance. Move-in ready and thoughtfully updated, this home offers the perfect combination of comfort, convenience, and low-maintenance living. Some photographs have been virtually staged.

24700 Deepwater Point Unit #23, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$799,900
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
$598,000
3 Beds ⋅ 2 Baths
Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised value—an outstanding opportunity!

204 Lincoln, Saint Michaels

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