55

Newest Homes for Sale in Saint Michaels, MD

Section Image Section Image
  • 9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /2

    $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 300 ft. of protected shoreline. Westerly exposure...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

    Tom Crouch Benson & Mangold, LLC

    9020 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 9206 Martingham Dr, Saint Michaels, MD 21663
    9206 Martingham Dr, Saint Michaels, MD 21663
    9206 Martingham Dr, Saint Michaels, MD 21663
    /43

    $630,000

    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft

    9206 Martingham Dr, Saint Michaels, MD 21663

    NEW PRICE — EXCEPTIONAL VALUE IN DESIRABLE MARTINGHAM!Welcome to 9206 Martingham Drive, a truly distinctive contemporary residence offering spacious living, 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,

    Salar Hakimi Samson Properties

    9206 Martingham Dr, 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

    $449,900

    • 4 Beds
    • 2.5 Baths
    • 1,876 Sq Ft

    9818 Tilghman Island Rd, McDaniel, MD 21647

    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: peaceful rural privacy, no HOA, and a

    Valerie Brown Coldwell Banker Realty

    9818 Tilghman Island Rd, McDaniel, MD 21647
  • 225 Tyler Ave, Saint Michaels, MD 21663
    225 Tyler Ave, Saint Michaels, MD 21663
    225 Tyler Ave, Saint Michaels, MD 21663
    /3

    $575,000

    Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,352 Sq Ft

    225 Tyler Ave, Saint Michaels, MD 21663

    Nestled beneath a cathedral of mature trees in sought-after Rio Vista, this beautifully updated home offers the perfect blend of privacy, convenience, and future potential. Extensively renovated between 2020 and 2024, the home features a well-appointed kitchen, spacious living areas, and a stunning screened porch that creates inviting spaces for everyday living and entertaining. The wooded

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    225 Tyler Ave, Saint Michaels, MD 21663
  • 344 Perry Cabin Dr, Saint Michaels, MD 21663
    344 Perry Cabin Dr, Saint Michaels, MD 21663
    344 Perry Cabin Dr, Saint Michaels, MD 21663
    /64

    $1,300,000

    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft

    344 Perry Cabin Dr, Saint Michaels, MD 21663

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    344 Perry Cabin Dr, 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

    $574,999

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    204 E Marengo St, Saint Michaels, MD 21663

    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

    Agent Photo

    Gretchen Wichlinski

    Compass

    (855) 695-6072

    204 E Marengo St, Saint Michaels, MD 21663
  • 23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
    /85

    $1,995,000

    • 3 Beds
    • 2 Baths
    • 2,160 Sq Ft

    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

    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

    Leslie Stevenson Shore Living Real Estate

    23776 Mount Pleasant Landing Cir, Saint Michaels, MD 21663
  • 107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    /77

    $1,165,000

    • 2 Beds
    • 2 Baths
    • 2,024 Sq Ft

    107 E Chestnut St, Saint Michaels, MD 21663

    Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living

    Monica Penwell TTR Sotheby's International Realty

    107 E Chestnut St, Saint Michaels, MD 21663
  • 934 Calvert Ave, Saint Michaels, MD 21663
    934 Calvert Ave, Saint Michaels, MD 21663
    934 Calvert Ave, Saint Michaels, MD 21663
    /29

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft

    934 Calvert Ave, Saint Michaels, MD 21663

    Welcome to this charming 3-bedroom, 2-bath home located on the edge of St. Michaels at the end of a quiet street. Thoughtfully maintained and updated, this property features a new roof, new downstairs HVAC system, updated appliances, and a spacious screened porch perfect for relaxing and entertaining.The main level includes a private office with its own exterior entrance, offering excellent

    Will Stone Benson & Mangold, LLC

    934 Calvert Ave, Saint Michaels, MD 21663
  • 8209 Tricefield Rd, Saint Michaels, MD 21663
    8209 Tricefield Rd, Saint Michaels, MD 21663
    8209 Tricefield Rd, Saint Michaels, MD 21663
    /63

    $2,500,000

    • 5 Beds
    • 2 Baths
    • 4,706 Sq Ft

    8209 Tricefield Rd, Saint Michaels, MD 21663

    Experience the best of Eastern Shore Living at this stunning waterfront retreat. Set on 8+ private acres, this solid brick Dutch Colonial offers timeless architecture, exceptional privacy and spectacular waterfrontage on San Domingo Creek. A long tree lined drive welcomes you to over 4400 square feet of thoughtfully designed living space. Additional highlights include a 2 car garage, paved

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    8209 Tricefield Rd, Saint Michaels, MD 21663
  • 24375 Widgeon Place Unit 37, Saint Michaels, MD 21663
    24375 Widgeon Place Unit 37, Saint Michaels, MD 21663
    24375 Widgeon Place Unit 37, Saint Michaels, MD 21663
    /50

    $499,999

    Open Sat 1:30PM - 3PM
    • 3 Beds
    • 3 Baths
    • 2,100 Sq Ft

    24375 Widgeon Place Unit 37, Saint Michaels, MD 21663

    Want to live close to Historic Saint Michaels in a beautiful and low maintenance setting offering ample first floor living? Welcome to 24375 Widgeon Place, Unit 37, nestled in the picturesque Martingham Community just outside Historic St. Michaels . This desirable END UNIT property is the epitome of style and comfort, encapsulating all the charms of eastern shore coastal living. Featuring 3

    Tiffany Cloud Meredith Fine Properties

    24375 Widgeon Place Unit 37, Saint Michaels, MD 21663
  • 8240 Tricefield Rd, Saint Michaels, MD 21663
    8240 Tricefield Rd, Saint Michaels, MD 21663
    8240 Tricefield Rd, Saint Michaels, MD 21663
    /61

    $2,445,000

    • 5 Beds
    • 6 Baths
    • 5,611 Sq Ft

    8240 Tricefield Rd, Saint Michaels, MD 21663

    Nestled on a gorgeous waterfront lot just minutes from St. Michaels, this exceptional property offers the perfect blend of privacy, comfort, and convenience. Enjoy an easy bike ride into town while coming home to a peaceful setting surrounded by mature, established trees and beautifully landscaped grounds.Built with quality and designed for comfortable living, the home features two spacious

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    8240 Tricefield Rd, 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

    $1,049,000

    • 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
  • 24678 New Post Rd, Saint Michaels, MD 21663
    24678 New Post Rd, Saint Michaels, MD 21663
    24678 New Post Rd, Saint Michaels, MD 21663
    /41

    $3,795,000

    • 4 Beds
    • 5 Baths
    • 6,404 Sq Ft

    24678 New Post Rd, Saint Michaels, MD 21663

    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

    Chuck Mangold Benson & Mangold, LLC

    24678 New Post Rd, 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
    /59

    $399,000

    • 2 Beds
    • 2.5 Baths
    • 1,477 Sq Ft

    24700 Deepwater Unit 20, Saint Michaels, MD 21663

    Situated in the established community of Martingham, and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship, energy efficiency, and long-term durability. The redesigned open floor plan creates a seamless flow throughout the main living areas, complemented by updated

    Monica Penwell TTR Sotheby's International Realty

    24700 Deepwater Unit 20, Saint Michaels, MD 21663
  • 9251 Mallard Point Ct, McDaniel, MD 21647
    9251 Mallard Point Ct, McDaniel, MD 21647
    9251 Mallard Point Ct, McDaniel, MD 21647
    /52

    $1,450,000

    • 3 Beds
    • 2.5 Baths
    • 1,816 Sq Ft

    9251 Mallard Point Ct, McDaniel, MD 21647

    Harris Creek Waterfront. This 3 bedroom, 2 bath well maintained brick one story house is the perfect getaway. Nestled on 1.63+/- acres it is the perfect blend of privacy and community. This home features a large kitchen with several entertaining areas including a cozy living room complete with a fireplace and a large living room that overlooks the huge screen porch and Harris Creek and a gracious

    Jim Corson Benson & Mangold, LLC

    9251 Mallard Point Ct, McDaniel, MD 21647
  • 203 Canton St, Saint Michaels, MD 21663
    203 Canton St, Saint Michaels, MD 21663
    203 Canton St, Saint Michaels, MD 21663
    /6

    $342,900

    $7K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,364 Sq Ft

    203 Canton St, Saint Michaels, MD 21663

    Discover this ranch-style home located 1 block to the center of downtown, perfect for those seeking convenience to everything St Michaels has to offer. This 3-bedroom, 2-bathroom residence offers 1,364 sq. ft. of potential, set on a generous 0.17-acre lot. The rails to trails is located right at the end of the street. With a little creativity and vision, this property can be transformed into your

    Melanie Hopkins Coldwell Banker Chesapeake Real Estate Company

    203 Canton St, Saint Michaels, MD 21663
  • 24555 Deepwater Point Dr, Saint Michaels, MD 21663
    24555 Deepwater Point Dr, Saint Michaels, MD 21663
    24555 Deepwater Point Dr, Saint Michaels, MD 21663
    /24

    $779,000

    $10K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 2,072 Sq Ft

    24555 Deepwater Point Dr, Saint Michaels, MD 21663

    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

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    24555 Deepwater Point Dr, Saint Michaels, MD 21663
  • 10554 Miracle House Cir, Claiborne, MD 21624
    10554 Miracle House Cir, Claiborne, MD 21624
    10554 Miracle House Cir, Claiborne, MD 21624
    /56

    $790,000

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,170 Sq Ft

    10554 Miracle House Cir, Claiborne, MD 21624

    Quality construction throughout. This Custom Coastal Home has all the bells and whistles ..... hardwood cherry floors, masonry fireplace, 1st floor primary suite, double porches to enjoy the sunsets over Eastern Bay. Gourmet kitchen with stainless steel appliances. Two screened in porches for dining or sleeping. Very private with professional landscaping. Easy walk to Claiborne boat ramp, beach

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    10554 Miracle House Cir, Claiborne, MD 21624
  • 962 San Domingo Ct, Saint Michaels, MD 21663
    962 San Domingo Ct, Saint Michaels, MD 21663
    962 San Domingo Ct, Saint Michaels, MD 21663
    /103

    $2,449,000

    • 4 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    962 San Domingo Ct, Saint Michaels, MD 21663

    This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering

    Eugene Smith TTR Sotheby's International Realty

    962 San Domingo Ct, Saint Michaels, MD 21663
  • 8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    8090 Bozman Neavitt Rd, Bozman, MD 21612
    /33

    $993,000

    • 3 Beds
    • 2 Baths
    • 1,362 Sq Ft

    8090 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled in the serene enclave of Bozman, this exquisite 1940s bungalow seamlessly blends coastal charm with modern luxury, offering an unparalleled lifestyle for discerning buyers. Spanning 1,362+/- square feet, this detached residence boasts three spacious bedrooms and two elegantly appointed bathrooms, each designed with high-end finishes that elevate everyday living. The country-style kitchen

    Bill Wieland Benson & Mangold, LLC

    8090 Bozman Neavitt Rd, Bozman, MD 21612
  • 602 Landing Rd, Saint Michaels, MD 21663
    602 Landing Rd, Saint Michaels, MD 21663
    602 Landing Rd, Saint Michaels, MD 21663
    /57

    $1,650,000

    $75K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 3,078 Sq Ft

    602 Landing Rd, Saint Michaels, MD 21663

    Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (866) 970-6336

    602 Landing Rd, 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
    /46

    $825,000

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,027 Sq Ft

    807 Radcliff Ave, Saint Michaels, MD 21663

    PUBLIC OPEN HOUSE SAT 6/20 FROM 12-3PM ***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

    Adam Ellison Long & Foster Real Estate, Inc.

    807 Radcliff Ave, Saint Michaels, MD 21663
  • 24700 Deepwater Unit 23, Saint Michaels, MD 21663
    24700 Deepwater Unit 23, Saint Michaels, MD 21663
    24700 Deepwater Unit 23, Saint Michaels, MD 21663
    /29

    $365,000

    $10K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,487 Sq Ft

    24700 Deepwater Unit 23, Saint Michaels, MD 21663

    Escape to the sought-after Swan Road Villa Townhomes, where low-maintenance living meets comfort, convenience, and lifestyle. This bright and inviting reverse-living townhome offers 2 bedrooms, 2.5 baths, and a thoughtfully designed floor plan that appeals to both full-time residents and weekend retreat seekers alike. The upper level serves as the heart of the home, featuring an open-concept

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    (844) 569-6559

    24700 Deepwater Unit 23, Saint Michaels, MD 21663
  • 24561 Deepwater Point Dr, Saint Michaels, MD 21663
    24561 Deepwater Point Dr, Saint Michaels, MD 21663
    24561 Deepwater Point Dr, Saint Michaels, MD 21663
    /57

    $649,000

    $50K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,144 Sq Ft

    24561 Deepwater Point Dr, Saint Michaels, MD 21663

    Select photos have been virtually staged to help visualize room layout and design possibilities. Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bath rancher features a light-filled, easy-flow floorplan with two ensuite bedrooms for added privacy and versatility. The home offers a garage and separate laundry room and opens to a charming backyard deck - ideal

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    24561 Deepwater Point 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
  • 504 Seymour Ave, Saint Michaels, MD 21663
    504 Seymour Ave, Saint Michaels, MD 21663
    504 Seymour Ave, Saint Michaels, MD 21663
    /89

    $1,049,000

    $151K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    504 Seymour Ave, Saint Michaels, MD 21663

    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

    Barbara Watkins Benson & Mangold, LLC

    504 Seymour Ave, Saint Michaels, MD 21663
  • 203 E Chew Ave, Saint Michaels, MD 21663
    203 E Chew Ave, Saint Michaels, MD 21663
    203 E Chew Ave, Saint Michaels, MD 21663
    /93

    $2,195,000

    $343K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 4,673 Sq Ft

    203 E Chew Ave, Saint Michaels, MD 21663

    Significant Price Improvement!!! Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully re-imagined through comprehensive renovations completed in 2023 and 2024. See virtual tours above. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms and 5 and a half baths, this home offers

    Richard Minchik Benson & Mangold, LLC

    203 E Chew Ave, 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

    $2,249,000

    • 3 Beds
    • 3 Baths
    • 3,017 Sq Ft

    7149 Drum Point Rd, Saint Michaels, MD 21663

    SNestled 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 Museum.A former successful

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7149 Drum Point Rd, 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

    $2,100,000

    $500K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    Set on 19.5 private acres just minutes from historic waterfront Saint Michaels, this exceptional 4,492 sq ft residence offers the perfect blend of space, privacy, and convenience. The home features four bedrooms and two and a half baths, with expansive living areas ideal for both everyday living and entertaining, including a well-appointed chef's kitchen. The thoughtfully designed layout includes

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, 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
    /60

    $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
  • 0 Deepwater Point Dr, Saint Michaels, MD 21663
    0 Deepwater Point Dr, Saint Michaels, MD 21663
    0 Deepwater Point Dr, Saint Michaels, MD 21663
    /41

    $249,000

    • Land
    • 1.12 Acres
    • $222,321 per Acre

    0 Deepwater Point Dr, Saint Michaels, MD 21663

    ONE OF THE LAST LOTS IN MARTINGHAM ON DEEP WATER POINT DRIVE. LOCATED VERY CLOSE TO THE COMMUNITY WATERFRONT PARK WITH GAZEBO AND CHAIRS FOR PICKNICKS OR JUST RELAXING IN THE BREEZE WATCHING THE BOATS GO BY ; DROP YOUR KAYAK OR ENJOY THE SUNSETS, WALK OR BIKE THERE. THIS LOT IS CLEANED, HAS A BEAUTIFUL ENTRANCE , WATER METER, AND IS READY FOR YOU TO BUILT YOUR MAIN RESIDENCE OR WEEKEND GET AWAY.

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    0 Deepwater Point Dr, Saint Michaels, MD 21663
  • 24965 Back Creek Dr, Saint Michaels, MD 21663
    24965 Back Creek Dr, Saint Michaels, MD 21663
    24965 Back Creek Dr, Saint Michaels, MD 21663
    /64

    $739,000

    • 4 Beds
    • 2.5 Baths
    • 2,798 Sq Ft

    24965 Back Creek Dr, Saint Michaels, MD 21663

    Tucked into the heart of Back Creek Landing, this home offers the kind of layout and setting that just works—comfortable, well thought out, and connected to both nature and town. The main living space is designed around how people actually live. The kitchen is open and inviting, with a bright eat-in area and an elevated counter with seating—perfect for morning coffee, casual meals, or simply

    Kathleen Coale Benson & Mangold, LLC

    24965 Back Creek Dr, 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
    /91

    $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
  • 222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    /59

    $1,885,000

    • 3 Beds
    • 2.5 Baths
    • 2,284 Sq Ft

    222 E Chestnut St, Saint Michaels, MD 21663

    Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    222 E Chestnut St, 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
    /75

    $1,195,000

    $155K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,528 Sq Ft

    114 W Chestnut St, St. Michaels, MD 21663

    Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides

    Wink Cowee Benson & Mangold, LLC

    114 W Chestnut St, St. Michaels, MD 21663
  • 24645 Long Haul Rd, Saint Michaels, MD 21663
    24645 Long Haul Rd, Saint Michaels, MD 21663
    24645 Long Haul Rd, Saint Michaels, MD 21663
    /112

    $2,550,000

    $350K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 3,677 Sq Ft

    24645 Long Haul Rd, Saint Michaels, MD 21663

    Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for

    Donna Dickinson Coldwell Banker Realty

    24645 Long Haul Rd, Saint Michaels, MD 21663
  • 100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    100 Bush Terrace, Saint Michaels, MD 21663
    /40

    $470,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    100 Bush Terrace, Saint Michaels, MD 21663

    This home allows for a 3.12% FHA Assumable Loan! Welcome to easy Eastern Shore living in the charming waterfront town of St. Michaels! This 3-bedroom, 2 bath, 1,232 sq. ft. home is located in the desirable community of Rio Vista offering direct access to the Miles River, complete with a community dock, boat slips, and boat ramp — perfect for boating, crabbing, paddleboarding, or sunset cruises.

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    100 Bush Terrace, 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
  • 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

    $480,000

    • 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

Showing Results 1 - 40, Page 1 of 2

Maryland Talbot County Saint Michaels

Newest Listings for Sale in Saint Michaels, MD

Frequently Asked Questions

What is the average home price in Saint Michaels, MD?
Homes for sale in Saint Michaels, MD have an average home price of $1,181,106.
Are home prices dropping in Saint Michaels?
Yes, home prices in Saint Michaels are down 11% in the last 12 months.
How many homes have sold over the last 12 months in Saint Michaels, MD?
78 homes have sold in Saint Michaels, MD over the last 12 months.
What is the average household income in Saint Michaels, MD?
The average household income in Saint Michaels, MD is $97K.
What are the most popular zip codes in Saint Michaels, MD?
The most popular zip codes in Saint Michaels, MD include 21663, 21612, 21601, 21676 and 21662.
How much do you need to make to afford a house in Saint Michaels?
The median home price in Saint Michaels is $799,999. If you put a 20% down payment of $160,000 and had a 30-year fixed mortgage with an interest rate of 6.47%, your estimated principal and interest payment would be $4,030 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $173K a year to afford the median home price in Saint Michaels. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Saint Michaels is $97K.
How are the schools in Saint Michaels, MD?
Saint Michaels, MD has highly rated public and private schools. Some of the best schools in Saint Michaels based on Niche Grades are Easton High School, St. Michaels Elementary School and St. Michaels Middle/High School. Browse all the schools in Saint Michaels, MD to learn more.

Home Prices in Saint Michaels, MD

The median home sale price in Saint Michaels, MD is $770,000, up 4% year-over-year. Homes in Saint Michaels sell in 76 days on average, compared to the national average of 58 days.

Home Price Trends

Median Sale Price
$770,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$470,000
Median 2 Bedroom Sale Price
$545,000
Average Price Per Sq Ft
$416
Number of Homes for Sale
47
Last 12 months Home Sales
78
Months of Supply
7.20
Median List Price
$799,999
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group