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Lot 16A Meadow, Saint Michaels
$799,000
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, Saint Michaels

Listing courtesy of Keller Williams Flagship. Contact:

7963 Pond Haven Ct, Saint Michaels
$630,000
3 Beds ⋅ 3 Baths
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 ceilings, a walk-in closet, and serene views of a backyard framed by mature crepe myrtles. Upstairs, you will find a massive bonus room equipped with a water hookup, two bright guest bedrooms, a shared full bath, and a large walk-in attic. Complete with a two-car garage, this home is the perfect Maryland Eastern Shore getaway.

7963 Pond Haven Ct, Saint Michaels

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

23820 Mount Pleasant Lndg, Saint Michaels
$2,800,000
4 Beds ⋅ 3 Baths
FALL IN LOVE WITH LIFE IN ST. MICHAELS! The Eastern Shore becomes even more captivating as the seasons change. Just one mile from vibrant downtown St. Michaels with on-going seasonal festivals, exceptional dining, charming boutiques and year-round waterfront activities. The meticulously renovated home provides comfortable & effortless one-level living, Thoughtful design in boutique resort-like setting. The westerly orientation provides expansive water views and truly spectacular sunsets. Offered completely turnkey EVERYTHING SHOWN INCLUDED THE OFFERING: all furnishings, linens, a fully equipped kitchen ... even the firewood! Notable features include a newly renovated saltwater pool with pool house, a three-car garage and a separate, fenced “tiny house” for the dogs! Enjoy the changing seasons, exceptional waterfront comfort & design, excellent dining & charming boutiques and year-round activities of Maryland's Eastern Shore. Whether for a weekend, an extended stay, or year-round enjoyment, everything is ready for your arrival.

23820 Mount Pleasant Lndg, Saint Michaels

Listing courtesy of Engel & Volkers Annapolis. Contact:

202 E Chestnut St, Saint Michaels
$1,250,000
3 Beds ⋅ 3 Baths
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 butler’s 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 naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler’s pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

202 E Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

111 Chesapeake Ave, Saint Michaels
$949,000
4 Beds ⋅ 3 Baths
Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated designer wallpaper accents throughout this stunning model home! Offering 4 bedrooms and 2.5 baths, the home includes a first‑floor primary suite with an ensuite spa bath, custom shower, and generous walk‑in closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1‑car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, you’ll enjoy easy access to charming shops, restaurants, waterfront activities, and year‑round festivals.

111 Chesapeake Ave, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact:

214 Madison Ave, Saint Michaels
$375,000
4 Beds ⋅ 2 Baths
Discover the potential of this 4-bedroom, 2-full-bath home in the desirable Rio Vista community of St. Michaels! Offering a spacious two-level layout, this property presents a fantastic opportunity for buyers looking to make a home their own or investors searching for their next project. Inside, you'll find hardwood floors, a separate dining room, a galley kitchen, and comfortable living spaces with plenty of possibilities. The flexible floor plan provides room to reimagine, update, and create a space that fits your needs. Step outside to enjoy a generously sized yard with plenty of space for entertaining, gardening, or simply relaxing outdoors. A storage shed adds convenience and additional storage. Located in the established Rio Vista community, residents enjoy access to wonderful neighborhood amenities, including a community boat ramp, kayak launch, and marina, making it easy to embrace the Eastern Shore lifestyle. Enjoy all the charm, shopping, and dining of historic St. Michaels while benefiting from a location outside the town limits. This home is ready for some TLC, but the opportunity is undeniable! Whether you're an investor, renovator, or buyer with a vision, this property offers the chance to create something special in a sought-after waterfront community. Bring your ideas and discover the possibilities!

214 Madison Ave, Saint Michaels

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

104 Mulberry St, Saint Michaels
$1,399,000
3 Beds ⋅ 3 Baths
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 1860-1870 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 offers the possibility to add onto the dwelling or a building a separate ADU or guest quarters. With many recent upgrades, this is a must see! Come by boat or by car. Buy in time to enjoy Saint Michaels wonderful holiday festivities. ACCESS BY APPT ONLY, surveillance cameras.

104 Mulberry St, Saint Michaels

Listing courtesy of RE/MAX One. Contact:

9020 Bozman Neavitt Rd, Saint Michaels
$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:

204 E Marengo St, Saint Michaels
$525,000
2 Beds ⋅ 1 Baths
Just reduced to $525,000—affordable, 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 investments—a new roof (2024), updated plumbing (2025), upgraded crawlspace with French drain (2025), and Thompson Creek windows—mean 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.

204 E Marengo St, Saint Michaels

Listing courtesy of Compass. Contact:

109 W Marengo St, Saint Michaels
$995,000
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:

204 Lincoln, Saint Michaels
$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:

7909 Church Nck, Saint Michaels
$2,000,000
4 Beds ⋅ 3 Baths
PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

7909 Church Nck, Saint Michaels

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

7149 Drum Pt, Saint Michaels
$2,149,000
3 Beds ⋅ 3 Baths
BACK ON THE MARKET WITH A NEW PRICE — DON’T MISS THIS EXCEPTIONAL WATERFRONT OPPORTUNITY! Tucked away in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront retreat offers a rare combination of privacy, comfort, and quintessential Eastern Shore charm—all just minutes from the heart of town. Formerly a successful vacation rental, this beautifully maintained three-bedroom brick home is designed for relaxed year-round living and effortless entertaining. The inviting open floor plan features rich wood flooring, double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views are part of everyday life here. Spend quiet mornings beneath the shade of mature trees along the shoreline, unwind in the hammock as the Chesapeake breezes drift by, or gather with friends and family for unforgettable outdoor entertaining. The expansive deck features a built-in outdoor kitchen and hot tub, while a charming stone-walled patio offers another inviting space to relax. An outdoor shower makes post-swim cleanup easy, and the private pool provides the perfect place to cool off on warm summer days. For boating enthusiasts, the property delivers exceptional waterfront amenities with a private dock offering approximately 3 feet MLW, a boat lift, and a boat launch, providing convenient access to the water. A separate two-room detached studio with a covered porch adds even more versatility—perfect for visiting guests, a home office, creative pursuits, or a private getaway—all while taking in beautiful water views. Additional features include an encapsulated crawl space and numerous thoughtful updates throughout the property. And when you're ready to explore beyond your own waterfront haven, you're just minutes from the best of St. Michaels, including acclaimed restaurants, boutique shopping, charming cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. Private, picturesque, and perfectly positioned—this is a rare opportunity to experience the very best of Eastern Shore waterfront living in one of St. Michaels' most sought-after neighborhoods.

7149 Drum Pt, Saint Michaels

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

101 Mulberry St, Saint Michaels
$997,000
4 Beds ⋅ 3 Baths
Beautifully restored Historic Victorian in the heart of Saint Michaels. 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. 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 floor. 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:

9180 Saint Michaels, Saint Michaels
$1,685,000
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:

8620 Bozman Neavitt, Saint Michaels
$8,495,000
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, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact:

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