Saint Michaels Homes for Sale

Saint Michaels Homes for Sale

Welcome to Saint Michaels, Maryland—a charming waterfront town nestled in Talbot County, known for its rich maritime history and picturesque scenery. This idyllic destination, often referred to as the "Heart of the Chesapeake," boasts a vibrant community, stunning views, and an array of outdoor activities that make it a true gem on the Eastern Shore.

Saint Michaels is famous for its historic architecture, quaint boutiques, and delightful eateries, all set against the backdrop of serene waters and lush landscapes. Whether you're exploring the charming streets lined with 19th-century homes or enjoying a leisurely stroll along the waterfront, you’ll find that every corner of this town exudes charm and character. The local marina offers boating and fishing opportunities, while nearby parks provide ample space for picnics, hiking, and birdwatching.

For those considering a move to this enchanting town, there are numerous homes for sale that cater to a variety of lifestyles and budgets. From cozy cottages with stunning bay views to elegant waterfront estates, Saint Michaels offers diverse real estate options that reflect the town's unique charm. Imagine waking up to the gentle sounds of the water and enjoying breathtaking sunsets from your own porch.

With its friendly community, vibrant arts scene, and a plethora of recreational activities, Saint Michaels is more than just a place to live—it's a lifestyle. Explore the available homes for sale and discover the perfect setting for your next chapter in this beautiful town. Embrace the opportunity to call Saint Michaels home, where every day feels like a vacation!

Newest Saint Michaels Homes for Sale

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. 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

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

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

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

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

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:

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 ⋅ 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

4 Beds ⋅ 3 Baths

Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles River—a treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electric vehicle charging station in the garage Invisible pet fence surrounding the yard The serene setting, spectacular views, and extensive updates create a rare opportunity to enjoy a low-maintenance lifestyle in a premier St. Michaels location. Whether relaxing on the patio overlooking the pond and golf course or enjoying the community's private waterfront park, this home offers the perfect blend of luxury, comfort, and convenience. A truly turnkey property where every detail has been thoughtfully updated and impeccably maintained.

9359 Martingham, Saint Michaels

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

3 Beds ⋅ 3 Baths

This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200 sf main level offers beautiful open large living room with fireplace and dining room for entertainment, which leads to fabulous sunroom overlooking the back yard garden. Modern kitchen off the dining room that leads to cozy breakfast room and back porch and patio. The Master suite has a completely remodeled bath with free standing soaker tub, walk in shower, his and hers vanities, as well as laundry. The key to this home is the second floor. This 800 SF space offers unimaginable flexibility. It can be various spaces based on your needs. A private space for your guests when visiting, a space for family and grandchildren, an in-law suite, or as a rental apartment with private entrance. Space is built to accommodate all the above with out any changes required. At present it has a living room, dining room, kitchen, bedroom and full bath with laundry, and under eave storage. The space, with the addition of one wall can add an additional bedroom making the property with all the aforementioned, a 3-bedroom home. In the backyard you will find self-contained workshop with HVAC, hot and cold running water, and attic, a Williamsburg garden shed, and parking for 3-4 cars. Home has encapsulated crawl space, and 2 zoned HVAC system.

504 Seymour Ave, Saint Michaels

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

4 Beds ⋅ 4 Baths

Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan delivers comfort and ease. High‑end finishes include Shaw luxury vinyl plank flooring, a gourmet kitchen with a 48" dual‑fuel range, custom tile backsplash, quartz countertops, stainless steel appliances, and a spacious walk‑in pantry. The inviting living area features a fireplace and seamless access to the covered front and rear porches. The primary suite offers a true retreat with a spa‑inspired ensuite bathroom, soaking tub, walk‑in shower, sitting area, and a large custom closet. Additional highlights include a dedicated laundry room, public sewer, and thoughtful craftsmanship throughout. This beautifully designed home is a must‑see for anyone seeking luxury living in one of Maryland’s most charming waterfront towns.

7865 Pea Neck, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

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