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Homes for Sale in 21663

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  • 24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
    /36

    $368,000

    $7K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft

    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663

    All resonable offers considered! Move in ready! Meticulously maintained 2 bedroom, 2.5 bath townhome offers comfort, privacy, and inviting living spaces throughout. The galley kitchen features a charming breakfast nook and flows into the dining and living area, highlighted by a wood-burning fireplace. Just beyond, a cozy sitting area opens to a brick patio overlooking a lovely backyard bordered

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    24362 Widgeon Place Unit 5, Saint Michaels, MD 21663
  • 204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    204 E Marengo St, Saint Michaels, MD 21663
    /72

    $549,999

    $25K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    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,

    Agent Photo

    Gretchen Wichlinski

    Compass

    204 E Marengo St, Saint Michaels, MD 21663
  • 803 New Ln, Saint Michaels, MD 21663
    803 New Ln, Saint Michaels, MD 21663
    803 New Ln, Saint Michaels, MD 21663
    /39

    $695,000

    $154K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    803 New Ln, Saint Michaels, MD 21663

    NEW PRICE!! Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design.A welcoming front porch with a classic porch swing sets the tone before stepping inside to

    Agent Photo

    Larry Brennan

    TTR Sotheby's International Realty

    803 New Ln, Saint Michaels, MD 21663
  • 1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    1211 Washington Dr, Saint Michaels, MD 21663
    /14

    $499,000

    $26K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1211 Washington Dr, Saint Michaels, MD 21663

    Desirable Rio Vista Duplex – Live in One Unit and Rent the Other! Rare opportunity to own a duplex in the sought-after Rio Vista community. Move into one unit and generate rental income from the other to help offset your mortgage payments. Properties like this seldom come on the market. Located in a water-access community, residents may enjoy dock access upon approval of the owner's application

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1211 Washington Dr, Saint Michaels, MD 21663
  • 9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
    /20

    $339,900

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663

    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

    Chuck Mangold Benson & Mangold, LLC

    9531 Quail Hollow Dr Unit 402, Saint Michaels, MD 21663
  • 1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    1215 Washington Dr, Saint Michaels, MD 21663
    /30

    $499,000

    $26K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    1215 Washington Dr, Saint Michaels, MD 21663

    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

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    1215 Washington Dr, Saint Michaels, MD 21663
  • 204 Lincoln Ave, Saint Michaels, MD 21663
    204 Lincoln Ave, Saint Michaels, MD 21663
    204 Lincoln Ave, Saint Michaels, MD 21663
    /27

    $598,000

    • 3 Beds
    • 2 Baths
    • 2,348 Sq Ft

    204 Lincoln Ave, Saint Michaels, MD 21663

    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

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    204 Lincoln Ave, Saint Michaels, MD 21663
  • 23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    /57

    $3,000,000

    Open Wed 4:30PM - 6:30PM
    • 4 Beds
    • 3 Baths
    • 2,815 Sq Ft

    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    Extraordinary waterfront living on 3.4 acres, just one mile from historic St. Michaels. Impeccably maintained and extensively renovated, this exceptional one-level home combines relaxed comfort with top-of-the-line luxury and lives like a private boutique resort. Offered completely turnkey—furnishings, linens, fully equipped kitchen and everything shown in the photographs conveys. Enjoy

    Carrie Mock Engel & Völkers Annapolis

    23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
  • 214 Madison Ave, Saint Michaels, MD 21663
    214 Madison Ave, Saint Michaels, MD 21663
    214 Madison Ave, Saint Michaels, MD 21663
    /23

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,743 Sq Ft

    214 Madison Ave, Saint Michaels, MD 21663

    Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout and plenty of potential for its next owner. The main level features beautiful hardwood floors, a galley kitchen, a separate dining room, and comfortable living spaces. Outside, you'll find a spacious yard with a storage shed, providing plenty of room for outdoor activities, gardening, or future

    Shelley Baden Berkshire Hathaway HomeServices PenFed Realty

    214 Madison Ave, Saint Michaels, MD 21663
  • 9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    9180 Saint Michaels Rd, Saint Michaels, MD 21663
    /66

    $1,685,000

    • 5 Beds
    • 5 Baths
    • 4,728 Sq Ft

    9180 Saint Michaels Rd, Saint Michaels, MD 21663

    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

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9180 Saint Michaels Rd, Saint Michaels, MD 21663
  • 111 Chesapeake Ave, Saint Michaels, MD 21663
    111 Chesapeake Ave, Saint Michaels, MD 21663
    /2

    $949,000

    Coming Soon Sep 10
    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft

    111 Chesapeake Ave, Saint Michaels, MD 21663

    Beautifully upgraded and thoughtfully designed, this home showcases designer‑selected wallpapers, custom finishes, and every modern convenience. The gourmet kitchen features quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling.Offering 4 bedrooms and 2.5 baths,

    Jana Meredith Meredith Fine Properties

    111 Chesapeake Ave, Saint Michaels, MD 21663
  • Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    /25

    $799,000

    New Construction
    • 4 Beds
    • 2.5 Baths

    Lot 16A Meadow St, Saint Michaels, MD 21163

    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

    George Bailey Keller Williams Flagship

    Lot 16A Meadow St, Saint Michaels, MD 21163
  • 925 Riverview Terrace, Saint Michaels, MD 21663
    925 Riverview Terrace, Saint Michaels, MD 21663
    925 Riverview Terrace, Saint Michaels, MD 21663
    /61

    $1,190,000

    • 3 Beds
    • 2.5 Baths
    • 2,300 Sq Ft

    925 Riverview Terrace, Saint Michaels, MD 21663

    Presenting 925 Riverview Terrace, a move in ready, charming home ideally located in the sought after Bentley Hay neighborhood just minutes from historic downtown St. Michaels. This beautifully renovated & meticulously maintained home offers Miles River views, a saltwater pool, 1st floor primary bedroom, attached 2 car garage, screened in porch, hardwood floors, gardens, home office, fiber optic

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    925 Riverview Terrace, Saint Michaels, MD 21663
  • 912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    /11

    $219,000

    $10K PRICE DROP
    • Land
    • 10,890 Sq Ft
    • $876,000 per Acre

    912 Calvert Ave, Saint Michaels, MD 21663

    One of the few remaining building lots in the St. Michaels area. This is a prime building lot, 75' x 150', ready for someone to design and construct a new home. Public water/sewer and high-speed internet available for hookup. Calvert Avenue is a convenient address, near schools, banks, grocery stores, boat ramps and St. Michaels' many fine shops, museums and restaurants. A public waterfront park

    Tom Crouch Benson & Mangold, LLC

    912 Calvert Ave, Saint Michaels, MD 21663
  • 24700 Deepwater Unit 20, Saint Michaels, MD 21663
    24700 Deepwater Unit 20, Saint Michaels, MD 21663
    24700 Deepwater Unit 20, Saint Michaels, MD 21663
    /55

    $385,000

    $14K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,477 Sq Ft

    24700 Deepwater Unit 20, Saint Michaels, MD 21663

    Whether you are looking for a full-time residence, weekend retreat, or investment property, this unit is truly move-in ready. Situated in Martingham community just minutes from St. Michaels, shops, restaurants 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,

    Monica Penwell TTR Sotheby's International Realty

    24700 Deepwater Unit 20, Saint Michaels, MD 21663
  • 101 Seymour Ave, Saint Michaels, MD 21663
    101 Seymour Ave, Saint Michaels, MD 21663
    101 Seymour Ave, Saint Michaels, MD 21663
    /56

    $995,000

    • 3 Beds
    • 2.5 Baths
    • 2,091 Sq Ft

    101 Seymour Ave, Saint Michaels, MD 21663

    Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive

    Henry Gibbons-Neff Meredith Fine Properties

    101 Seymour Ave, Saint Michaels, MD 21663
  • 807 Radcliff Ave, Saint Michaels, MD 21663
    807 Radcliff Ave, Saint Michaels, MD 21663
    807 Radcliff Ave, Saint Michaels, MD 21663
    /41

    $799,900

    $60K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,027 Sq Ft

    807 Radcliff Ave, Saint Michaels, MD 21663

    ***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

    Adam Ellison Long & Foster Real Estate, Inc.

    807 Radcliff Ave, Saint Michaels, MD 21663
  • 9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /32

    $1,995,000

    • 4 Beds
    • 2.5 Baths
    • 3,028 Sq Ft

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663

    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,

    Tom Crouch Benson & Mangold, LLC

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 104 Mulberry St, Saint Michaels, MD 21663
    104 Mulberry St, Saint Michaels, MD 21663
    104 Mulberry St, Saint Michaels, MD 21663
    /74

    $1,470,000

    • 3 Beds
    • 2.5 Baths
    • 1,938 Sq Ft

    104 Mulberry St, Saint Michaels, MD 21663

    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

    Barbara Best RE/MAX One

    104 Mulberry St, Saint Michaels, MD 21663
  • 7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    7149 Drum Point Rd, Saint Michaels, MD 21663
    /71

    $2,149,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,017 Sq Ft

    7149 Drum Point Rd, Saint Michaels, MD 21663

    NEW PRICE DO NOT MISS THIS ONENestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7149 Drum Point Rd, Saint Michaels, MD 21663
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /27

    $295,000

    • Land
    • 23,958 Sq Ft
    • $536,364 per Acre

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot,

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 109 W Marengo St, Saint Michaels, MD 21663
    109 W Marengo St, Saint Michaels, MD 21663
    109 W Marengo St, Saint Michaels, MD 21663
    /32

    $995,000

    $54K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,250 Sq Ft

    109 W Marengo St, Saint Michaels, MD 21663

    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

    Chuck Mangold Benson & Mangold, LLC

    109 W Marengo St, Saint Michaels, MD 21663
  • 9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
    /40

    $374,000

    $11K PRICE DROP
    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663

    REDUCED CLEAN UNIT ...CASUAL LIVING IN SOUTH AFTER "THE LINK AT PERRY CABIN " MARTINGHAM COMMUNITY Nestled within the prestigious Quail Hollow community in desirable Martingham, this exceptional residence enjoys a prime setting overlooking the renowned Links at Perry Cabin golf course. One of the few units featuring a screened porch, this home offers the perfect blend of elegance, comfort,

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 205, Saint Michaels, MD 21663
  • 114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    114 W Chestnut St, St. Michaels, MD 21663
    /51

    $1,195,000

    • 4 Beds
    • 4 Baths
    • 3,528 Sq Ft

    114 W Chestnut St, St. Michaels, MD 21663

    Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant

    Robert Lacaze TTR Sotheby's International Realty

    114 W Chestnut St, St. Michaels, MD 21663
  • 202 E Chestnut St, Saint Michaels, MD 21663
    202 E Chestnut St, Saint Michaels, MD 21663
    202 E Chestnut St, Saint Michaels, MD 21663
    /50

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 2,052 Sq Ft

    202 E Chestnut St, Saint Michaels, MD 21663

    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

    Wink Cowee Benson & Mangold, LLC

    202 E Chestnut St, Saint Michaels, MD 21663
  • 104 Madison Ave, Saint Michaels, MD 21663
    104 Madison Ave, Saint Michaels, MD 21663
    /2

    $459,900

    • 4 Beds
    • 4 Baths
    • 2,420 Sq Ft

    104 Madison Ave, Saint Michaels, MD 21663

    This well-maintained duplex with new roof in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units

    Chuck Mangold Benson & Mangold, LLC

    104 Madison Ave, Saint Michaels, MD 21663
  • 101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    101 Brooks Ln, Saint Michaels, MD 21663
    /28

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    101 Brooks Ln, Saint Michaels, MD 21663

    Seller will offer a 10K credit for a storage shed with full price offer! Welcome to this beautifully updated cottage in the heart of St. Michaels—where modern comfort meets Eastern Shore charm. Perfectly situated within walking distance to the town’s shops, restaurants, Rails to Trails, and the renowned Maritime Museum, this single‑level home offers both convenience and a peaceful, private

    Stacie Luhrman Benson & Mangold, LLC

    101 Brooks Ln, Saint Michaels, MD 21663
  • 101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    101 Mulberry St, Saint Michaels, MD 21663
    /38

    $1,129,000

    $155K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    101 Mulberry St, Saint Michaels, MD 21663

    Dramatic Price Drop!!! Seller ready to sell this 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

    Jana Meredith Meredith Fine Properties

    101 Mulberry St, Saint Michaels, MD 21663
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /25

    $779,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    A rare opportunity to pair a half-acre+ wooded in-town parcel with a thoughtfully designed single-level home concept in the heart of St. Michaels. This Concept A plan illustrates a 3-bedroom, 2-bath residence totaling approximately 1,710 square feet, featuring one-level living and an attached one-car garage. Designed to maximize functionality and flow, the concept offers flexible living spaces

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 965 San Domingo Ct, Saint Michaels, MD 21663
    965 San Domingo Ct, Saint Michaels, MD 21663
    965 San Domingo Ct, Saint Michaels, MD 21663
    /68

    $2,395,000

    Coming Soon Sep 4
    • 4 Beds
    • 4.5 Baths
    • 4,116 Sq Ft

    965 San Domingo Ct, Saint Michaels, MD 21663

    Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main

    Kathy Christensen TTR Sotheby's International Realty

    965 San Domingo Ct, Saint Michaels, MD 21663
  • 104 Cherry St, Saint Michaels, MD 21663
    104 Cherry St, Saint Michaels, MD 21663
    /2

    $795,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,718 Sq Ft

    104 Cherry St, Saint Michaels, MD 21663

    Historic St. Michaels Opportunity! Priced to Sell Quickly! Property sold strictly "as-is", inspections for informational purposes only. Built circa 1860, this spacious 4-bedroom, 3-full-bath historic home offers 2,718 square feet and an exceptional in-town location just half a block from the harbor, restaurants, shops, the Chesapeake Bay Maritime Museum, and all that makes St. Michaels such a

    Jennifer Pogoda Redfin Corp

    104 Cherry St, Saint Michaels, MD 21663
  • 228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
    /119

    $1,945,000

    $50K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 4,089 Sq Ft

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663

    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

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
  • 7865 Pea Neck Rd, Saint Michaels, MD 21663
    7865 Pea Neck Rd, Saint Michaels, MD 21663
    7865 Pea Neck Rd, Saint Michaels, MD 21663
    /61

    $1,379,800

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,332 Sq Ft

    7865 Pea Neck Rd, Saint Michaels, MD 21663

    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

    Jana Meredith Meredith Fine Properties

    7865 Pea Neck Rd, Saint Michaels, MD 21663
  • 9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
    /36

    $455,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663

    Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • 303 Manor St, Saint Michaels, MD 21663
    303 Manor St, Saint Michaels, MD 21663
    303 Manor St, Saint Michaels, MD 21663
    /50

    $1,985,000

    • 3 Beds
    • 3 Baths
    • 2,622 Sq Ft

    303 Manor St, Saint Michaels, MD 21663

    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

    Monica Penwell TTR Sotheby's International Realty

    303 Manor St, Saint Michaels, MD 21663
  • 7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    7909 Church Neck Rd, Saint Michaels, MD 21663
    /50

    $2,000,000

    $600K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    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

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, Saint Michaels, MD 21663
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /25

    $999,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    108 Miles, Saint Michaels, MD 21663

    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

    Chuck Mangold Benson & Mangold, LLC

    108 Miles, Saint Michaels, MD 21663
  • 9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    9818 Tilghman Island Rd, McDaniel, MD 21647
    /38

    $430,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    9818 Tilghman Island Rd, McDaniel, MD 21647

    Improved Price!! Don't miss out ! The Perfect Blend of Space & Proximity. Loved by one family, this 4 bedroom 2 1/2 bath home is ready for the next owner. Situated on a beautiful1-acre parcel, this property is framed by magnificent, beautifully spaced mature trees and a cool gazebo to enjoy the park-like setting. Located in desirable McDaniel, you enjoy the ultimate Eastern Shore lifestyle:

    Valerie Brown Coldwell Banker Realty

    9818 Tilghman Island Rd, McDaniel, MD 21647
  • 9745 Tilghman Island Rd, McDaniel, MD 21647
    9745 Tilghman Island Rd, McDaniel, MD 21647
    9745 Tilghman Island Rd, McDaniel, MD 21647
    /15

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,496 Sq Ft

    9745 Tilghman Island Rd, McDaniel, MD 21647

    Mc Daniel Rancher - This 3 Bedroom and 2 Bathroom rancher in the community of Mc Daniel, is conveniently located approximately 5 miles to St. Michaels. Close to half an acre of land, this property offers plenty of space for gardening and relaxing or grilling on the back deck. Just over 1400 square feet of living space, the dining room opens to the living room creating a generous space for

    Marla Baines Meredith Fine Properties

    9745 Tilghman Island Rd, McDaniel, MD 21647
Maryland Talbot County Saint Michaels

Real Estate & Homes for Sale in 21663

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