49 properties for sale in Mount Pleasant, District 2 St Michaels Talbot County Maryland

Enjoy the best of St. Michaels with convenient access to recreation, waterfront activities, schools and downtown. The newly renovated split-foyer home is truly move-in ready. The nicely landscaped grounds feature a fenced rear yard with mature trees, large patio and an in-ground swimming pool, creating a wonderful setting for outdoor enjoyment. Inside, the main level is filled with natural light and offers an open floor plan with a comfortable living room, dining area and brand new beautifully updated kitchen featuring white cabinetry and new appliances. Beautiful wood floors throughout. The home offers four bedrooms and three and a half baths, with the added convenience of stacked washer and dryer setups on both levels. Large family room overlooking rear yard with wood burning brick fireplace with outside access to pool. First and second floor primary suites with custom tile bathrooms. Off street parking with no rental restrictions and no town taxes. Close to YMCA, school, restaurants

Big reduction. Great value do not miss out! Charming Coastal Retreat with Endless Potential in Backcreek LandingWelcome to this beautiful two-story home in the highly sought-after Backcreek Landing neighborhood, just minutes from historic St. Michaels. Blending coastal elegance with incredible value, this property features a brand-new roof with lifetime shingles and is attractively priced, leaving you budget flexibility to update the bathrooms to your taste. From the front porch, you can enjoy serene views of the pond right across the street and step directly onto the neighborhood walking trail. The main level offers a private front office, a formal dining room, and a grand living room with dramatic cathedral ceilings and French doors leading to a spacious deck. The casual dining area opens through separate French doors to a wonderful screened porch, creating a seamless flow for indoor-outdoor living. Your main-floor primary suite serves as a private sanctuary, complete with tray ceili

Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butlers pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows natur

This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the'Keithley House, the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1- time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovely home, the lot is one of the larger ones in the area, at a higher elevation with beautiful landscaping, just redone, w/ gardens, fruit trees, patios, antique productive grape arbor, large shed, paths, fencing & rear gate, forming a lovely backyard oasis. Off street parking for 3 vehicles, lined w/ knock out roses & pencil Hollies. This lot

With huge sunset views across Eastern Bay, this stylishly-updated property is the perfect retreat! The main house with three en-suite bedrooms overlooks a large waterside deck, saltwater pool and screened pool house. A wisteria-covered pergola leads the the 1920's two-bedroom guest house with wrap-around porch at the water's edge. The one-bedroom carriage house completes the compound. Great elevation, substantial dock with 4' MLW and heavy-duty rip rap, newer septic. And all just five miles from historic St. Michaels

A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Codstyle 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

Beautifully restored Historic Victorian in the heart of Saint Michaels. From the wide, welcoming front porch to the gated, manicured yardcomplete with a hammock ideal for long afternoon napsevery space is designed for comfort and relaxation. A brick walkway leads to the custom beveledglass 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 marbletile full bath. The private thirdfloor primary suite offers a peaceful retreat with its own ensuite bath. Seller raised the home 3 feet and the lot 2 feet to help will water run-off and has a dry encapsulated crawl space with cement f

Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin. A rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. Adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a chef-inspired gourmet kitchen designed for elevated entertaining and showcases premium appliances, including a 60-inch extra-large refrigerator/freezer, Wolf propane cooktop, and integrated refrigerated and freezer beverage drawers thoughtfully integrated into the cabinetry. The first-floor primary suite provides effortless main-level living with a private enclosed porch and spa-like bath retreat. This combined property conveys two deep-water boat slips (6' MLW) with water and electricity, each able to accommodate a 40-foot vessel. Community amenities include kayak launch; tennis courts lined for pickle

Welcome to Ingleton, a waterfront community ideally situated along the Miles River and Hunting Creek. Set on 2.7 acres with a Miles River water view, this traditional two-story home offers 4 bedrooms, 2.5 baths, an attached one-car garage, and a 16' x 24' pole barn with lean-to. Major renovations and improvements were completed in late 2021/2022, including a new 50-year roof, new HVAC system, new water heater, and a completely renovated kitchen and breakfast area featuring granite countertops, a center island/breakfast bar, stainless steel appliances, updated cabinetry and flooring, recessed lighting, and an under-sink reverse osmosis system. Hardwood floors extend throughout the principal living areas, and the spacious living room features a wood-burning fireplace and mantel. A sunroom opens to the expansive backyard, bordered by mature trees and tall pines. Additional improvements include a renovated first-floor powder room, semi-conditioned crawlspace with vapor barrier and new sump

Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living

Just reduced to $525,000affordable, turn-key easy living near the water in St. Michaels. Located 1.5 blocks from public boat ramps and marina access, this updated coastal getaway delivers effortless weekend living without Historic District restrictions. Major recent capital investmentsa new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windowsmean zero weekend project lists. Spend your Saturdays lounging by your private in-ground pool, hosting at the beach bar with cable TV, or storing kayaks and gear in the detached garage. Convenient main-level living just steps from downtown dining, coffee shops, and harbor parks. Perfect as a low-maintenance weekend retreat or primary escape from Day 1

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 roomperfect 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

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 valuean outstanding opportunity!

RDesirable Rio Vista Duplex Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with a cozy eating area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath Whether you're looking for an owner-occupied investment property or a fully leased income-producing asset, this duplex presents excellent potential. These units have a strong rental history and are consistently in demand. Both units are currently tenant-occupied. THIS IS WHY WE DO NOT HAVE INTERIOR PICTURES For investors seeking additional opportunities, the neighboring building at 1211 Rio Vista is also available for purchase (MLS #MDTA2012-). Educed. Reduced. Do not wai

Grafton Manour EstateA Rare Chesapeake Waterfront Legacy. Embrace the quiet grandeur of Grafton Manour Estate, an 86-acre peninsula wrapped by approximately 1.5 miles of shoreline with panoramic water views in every direction. Bordered by Briary Cove to the east, Harris Creek to the southeast, and Waterhole Cove to the west, this extraordinary property blends pastoral elegance with true Chesapeake Bay access. Property Highlights: 86 acres with sweeping water vistas, open fields, and meticulously manicured lawns. Varied shoreline: riprap, sandy beaches, and natural grasses. Deep-water pier with 7' MLW, suitable for larger boats and sailboats; direct access to the Chesapeake Bay. Two subdivided, waterfront lots included: Lot 2: 6 acres on Briary Cove (east side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Lot 3: 5.5 acres is located on Waterhole Cove (west side), with prior SDA approval for a 4-bedroom home (re-evaluation required). Historic Lowes Family Cemet

A Charming Eastern Shore Retreat located between Easton and Saint Michaels with Water Access & Endless Possibilities! Welcome to 5735 Irish Creek Road, a beautifully updated property offering a wonderful blend of Eastern Shore charm, modern improvements, water access, and incredible potential. Set in the peaceful countryside of Royal Oak, this distinctive property is ready for its next owner to bring their vision to life. Inside the main residence, a renovated gourmet kitchen provides a stylish and functional centerpiece for everyday living and entertaining. The inviting sunroom features a vaulted ceiling, creating a bright and airy space to relax and enjoy the surrounding setting. Recent improvements include a new hot water heater, new air conditioning system, new septic system, and updated flooring throughout. A newly added front brick porch enhances the home's curb appeal and creates a welcoming spot to enjoy the peaceful surroundings. The property also offers exceptional flexibilit

Brand new & move-in ready*. This spacious ranch home offers easy one level living and features high end finishes throughout, including a gourmet kitchen with stylish white and timber cabinetry, satin bronze hardware, quartz countertops, subway tile backsplash, and stainless steels appliances including a double oven, gas cooktop and range hood. The living room features a gas fireplace and large picture windows, providing an abundance of natural light. The owner's suite is equipped with a walk-in closet and luxurious bath with dual vanity, spacious shower w/dual shower heads and tile surround. Rounding out the main level is two additional bedrooms and a full bath with ceramic tile flooring and surround. Additional amenities include 9' ceilings, two car side load garage, LVP flooring, ceramic tile in all baths and laundry room, public sewer (no private septic), 30 year architectural shingles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation

This beautifully maintained 3-bedroom, 3-bathroom home is special the second you pull into the driveway. Situated on nearly an acre in a private and peaceful setting. When you enter the front door, you will be drawn to the large screen porch ion the rear of the home and you are also greeted by a generous living room with two fireplaces. The kitchen is large and functional with plenty of space for a large table with an office/den directly off the kitchen. Upstairs you will find 3 ensuite bedrooms with a stunning primary with a beautiful walk in shower. The outside space is stunning with a large screen porch and separate patio to enjoy the very private and parklike back yard. Other features include a conditioned crawlspace, tankless hot water heater and high speed internet provided by Easton Utilities. The ferry to Oxford, and public boat ramp are right down the road and this area is renowned for its biking and beauty. Being 10 minutes from Easton and Saint Michaels this is the ideal set

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by man