115

Homes for Sale near St. Michaels Middle/High School

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  • 5877 Tilghman Island Rd, Tilghman, MD 21671
    5877 Tilghman Island Rd, Tilghman, MD 21671
    5877 Tilghman Island Rd, Tilghman, MD 21671
    /33

    $550,000 Open Fri 11AM - 1PM

    • 2 Beds
    • 1.5 Baths
    • 2,107 Sq Ft

    5877 Tilghman Island Rd, Tilghman, MD 21671

    This unique property is nestled in a setting of mature trees and lush landscaping that gives it privacy from the main road. The original two-story, three room house’s first owner was probably a waterman and there are views of Dogwood Harbor from the rear of the property. The house dates from the early 1900’s and has undergone extensive renovations through the years, without compromising its

    Agent Photo

    Angela Simonelli

    Compass

    (410) 200-0414

    5877 Tilghman Island Rd, Tilghman, MD 21671
  • 7392 Back St, Newcomb, MD 21653
    7392 Back St, Newcomb, MD 21653
    7392 Back St, Newcomb, MD 21653
    /9

    $799,000 Open House 5/10

    • 5 Beds
    • 3.5 Baths
    • 2,254 Sq Ft

    7392 Back St, Newcomb, MD 21653

    Professional photos posting by May 11th.Coastal meets Victorian in this exquisitely renovated home in the quaint waterfront village of Newcomb! The open floor plan exudes a peaceful vibe in every room--airy, light color palette, incredible indoor-outdoor living spaces. This home is all about enjoying life on the Eastern Shore! Cozy up by the gas indoor fireplace in the cooler months. Or enjoy the

    Agent Photo

    Tiffany Cloud

    Meredith Fine Properties

    (410) 304-7796

    7392 Back St, Newcomb, MD 21653
  • 0 Holly Woods Rd, 5, Bay Hundred, MD 21665
    0 Holly Woods Rd, 5, Bay Hundred, MD 21665
    0 Holly Woods Rd, 5, Bay Hundred, MD 21665
    /24

    $189,000

    • Land
    • 2.49 Acres
    • $75,904 per Acre

    0 Holly Woods Rd, 5, Bay Hundred, MD 21665

    Deep Harbour Farm Sherwood 2.49. Acre Building Lot.This is one of the last remaining building lots available in this wonderful water privileged community.Located at the end of a cul-de-sac on Holly Woods Road just steps away from the community waterfront pier & boat dock. Great opportunity to build the home of your own design now or in the future.

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 222-5571

    0 Holly Woods Rd, 5, Bay Hundred, MD 21665
  • 21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    /10

    $80,000

    • Land
    • 0.30 Acre
    • $266,667 per Acre

    21472 Willey Rd, Tilghman, MD 21671

    Tilghman Island. Clear level building lot with public sewer available. The perfect spot for your new vacation / retirement home. Excellent opportunity to make your island dream come true.

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 382-8747

    21472 Willey Rd, Tilghman, MD 21671
  • 9191 Deepwater Point Rd, Saint Michaels, MD 21663
    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    9191 Deepwater Point Rd, Saint Michaels, MD 21663
    /103

    $3,300,000

    • 5 Beds
    • 4 Baths
    • 5,088 Sq Ft

    9191 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to 9191 Deepwater Point Road, a captivating waterfront estate set on over 12 acres nestled along the Miles River and Long-Haul Creek in St. Michaels, Maryland. Built in 1988, this 5,088 -square-foot home features 5 bedrooms and 4 full bathrooms, the convenient first-floor primary suite is spacious and includes a sauna, fireplace and sunroom with a vaulted ceiling, skylights and panoramic

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (866) 528-7062

    9191 Deepwater Point Rd, Saint Michaels, MD 21663
  • 0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    /12

    $89,000

    • Land
    • 0.30 Acre
    • $296,667 per Acre

    0 Sinclair Rd, Tilghman Island, MD 21671

    Sinclair Ave. Tilghman Island. Clear level building lot with public sewer. This lot is ready for you to make your dream of island life come true.Enjoy the best sunsets at the end of the street at Sinclair Community Park .

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 297-6839

    0 Sinclair Rd, Tilghman Island, MD 21671
  • 27753 Villa Rd, Easton, MD 21601
    27753 Villa Rd, Easton, MD 21601
    27753 Villa Rd, Easton, MD 21601
    /46

    $3,450,000 Open Sun 12PM - 3PM

    • 6 Beds
    • 4.5 Baths
    • 4,568 Sq Ft

    27753 Villa Rd, Easton, MD 21601

    Stunning Ilex-built modern farmhouse set on over 3 acres along scenic Glebe Creek. This thoughtfully designed home features open-concept living with seamless sight lines from the kitchen through the dining area to the living room, creating an ideal space for everyday living and entertaining. A spacious screened-in porch extends from the main living areas and leads out to a waterside pool with an

    Clifford Meredith Meredith Fine Properties

    27753 Villa Rd, Easton, MD 21601
  • 6508 Partridge Ln, Royal Oak, MD 21662
    6508 Partridge Ln, Royal Oak, MD 21662
    6508 Partridge Ln, Royal Oak, MD 21662
    /53

    $2,495,000

    • 3 Beds
    • 2.5 Baths
    • 3,765 Sq Ft

    6508 Partridge Ln, Royal Oak, MD 21662

    STUNNING WESTERLY SETTING WITH AMAZING VIEWS. THIS 3 BEDROOM HOME WITH 12 FOOT CEILINGS IS LIVING ON ONE FLOOR AT ITS BEST. OPEN FLOORPLAN ,HEATED FLOORS IN ALL ROOMS,SLIDING DOORS FROM DINING ROOM AND KITCHEN LEADING TO FABULOUS SCREENED PORCH, OUTDOOR KITCHEN, PATIO AND WALK WAYS TO THE INGOUND POOL AREA. ENDLESS UNOBSTRUCTED VIEWS ACROSS BRIDGE CREEK,THE MOUTH OF BROAD CREEK AND THE CHOPTANK

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    6508 Partridge Ln, Royal Oak, MD 21662
  • 6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    6020 Sunset Ln, Tilghman, MD 21671
    /50

    $2,795,000

    • 7 Beds
    • 7 Baths
    • 6,377 Sq Ft

    6020 Sunset Ln, Tilghman, MD 21671

    Welcome to Tilghman Landing on the Chesapeake Bay! This unique waterfront property offers an incredible opportunity, featuring three separate homes, two of which include garages, as well as a charming crab shack and private dock, all situated on .625 acres of Chesapeake Bay shoreline.Home #1: 6020 Sunset LaneThis spacious residence offers breathtaking, unobstructed views of the Bay. It includes 3

    Melissa Tippett TTR Sotheby's International Realty

    6020 Sunset Ln, Tilghman, MD 21671
  • 4768 Bar Neck Rd, Tilghman, MD 21671
    4768 Bar Neck Rd, Tilghman, MD 21671
    4768 Bar Neck Rd, Tilghman, MD 21671
    /88

    $1,995,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 2.5 Baths
    • 2,801 Sq Ft

    4768 Bar Neck Rd, Tilghman, MD 21671

    Welcome to your private waterfront retreat in charming Tilghman Island on over 5 acres of beautifully maintained property. The huge wraparound water views and broad open skies are equally inspiring. Uniquely situated at the base of the Island, this southern facing home looks across the mouth of the Choptank River and down the Chesapeake and for miles and miles. Find your tranquility in this

    Debra Crouch Benson & Mangold, LLC

    4768 Bar Neck Rd, Tilghman, MD 21671
  • 25686 Edgeview Rd, Royal Oak, MD 21662
    25686 Edgeview Rd, Royal Oak, MD 21662
    25686 Edgeview Rd, Royal Oak, MD 21662
    /64

    $1,495,000

    • 4 Beds
    • 3.5 Baths
    • 4,124 Sq Ft

    25686 Edgeview Rd, Royal Oak, MD 21662

    Lovely waterfront home between Easton and St. Michaels (Royal Oak). Fantastic waterfront views. Nestled along the peaceful shores of Edge Creek. Fantastic Winter and summer sunsets. This beautifully maintained waterfront property offers timeless charm and unmatched tranquility. Due west exposure with fantastic sunsets both winter an summer. Long private pier with boat lift. Home is

    Mark Lappen Meredith Fine Properties

    25686 Edgeview Rd, Royal Oak, MD 21662
  • 1026 Riverview Terrace, Saint Michaels, MD 21663
    1026 Riverview Terrace, Saint Michaels, MD 21663
    1026 Riverview Terrace, Saint Michaels, MD 21663
    /70

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 2,535 Sq Ft

    1026 Riverview Terrace, Saint Michaels, MD 21663

    Experience luxury living in this newly renovated coastal-style home in St. Michaels. Situated on a double lot, this is an exceptional and rare offering, combining water views and water access with a high quality home, redone with incredible attention to detail and livability. The exterior is tastefully appointed with painted brick and shingle-style siding, and an inviting covered front porch

    Carolina Barksdale Benson & Mangold, LLC

    1026 Riverview Terrace, Saint Michaels, MD 21663
  • 22769 Almost Neavitt Rd, Bozman, MD 21612
    22769 Almost Neavitt Rd, Bozman, MD 21612
    22769 Almost Neavitt Rd, Bozman, MD 21612
    /65

    $995,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,724 Sq Ft

    22769 Almost Neavitt Rd, Bozman, MD 21612

    Immerse yourself in luxurious Eastern Shore living at this breathtaking waterfront retreat! Expertly designed by renowned local architect Pam Gardener, this four-bedroom, two-bath sanctuary rests at the end of a private road on a .92-acre lot, perfectly balancing tranquil seclusion with panoramic beauty. Showcasing 78 feet of riprap-protected shoreline along picturesque Balls Creek (flowing into

    Barbara McCaffrey Redfin Corp

    22769 Almost Neavitt Rd, Bozman, MD 21612
  • 6379 Cedar Cove Rd, Royal Oak, MD 21662
    6379 Cedar Cove Rd, Royal Oak, MD 21662
    6379 Cedar Cove Rd, Royal Oak, MD 21662
    /32

    $1,249,000

    • 3 Beds
    • 3 Baths
    • 2,586 Sq Ft

    6379 Cedar Cove Rd, Royal Oak, MD 21662

    Chuck Mangold Benson & Mangold, LLC

    6379 Cedar Cove Rd, Royal Oak, MD 21662
  • 25832 Turner Ave, Royal Oak, MD 21662
    25832 Turner Ave, Royal Oak, MD 21662
    25832 Turner Ave, Royal Oak, MD 21662
    /11

    $1,235,000 New Construction

    • 4 Beds
    • 2.5 Baths

    25832 Turner Ave, Royal Oak, MD 21662

    Centrally located between Easton and St Michaels and just a stone’s throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County’s premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Just minutes to Talbot County's favorite waterfront towns by car,

    Chuck Mangold Benson & Mangold, LLC

    25832 Turner Ave, Royal Oak, MD 21662
  • 25842 Bellevue School Rd, Royal Oak, MD 21662
    25842 Bellevue School Rd, Royal Oak, MD 21662
    25842 Bellevue School Rd, Royal Oak, MD 21662
    /8

    $1,235,000 New Construction

    • 4 Beds
    • 2.5 Baths

    25842 Bellevue School Rd, Royal Oak, MD 21662

    Centrally located between Easton and St Michaels and just a stone’s throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County’s premier waterfront communities with 13 half acre to 1.5 acre home sites. The community features its own private beach and kayak launch with nearby public park with playground and marina. Just minutes to Talbot County's favorite waterfront towns by car,

    Chuck Mangold Benson & Mangold, LLC

    25842 Bellevue School Rd, Royal Oak, MD 21662
  • 25831 Turner Ave, Royal Oak, MD 21662
    25831 Turner Ave, Royal Oak, MD 21662
    25831 Turner Ave, Royal Oak, MD 21662
    /13

    $979,900 New Construction

    • 4 Beds
    • 2.5 Baths

    25831 Turner Ave, Royal Oak, MD 21662

    Centrally located between Easton and St Michaels and just a stone’s throw from the Oxford Bellevue Ferry on the Tred Avon, one of Talbot County’s premier waterfront communities with 13 half acre to 1.5 acre home sites, nine lots with water views and four waterfront lots to choose from. The community features its own private beach and kayak launch with nearby public park with playground and

    Chuck Mangold Benson & Mangold, LLC

    25831 Turner Ave, Royal Oak, MD 21662
  • 9190 Pennywhistle Dr, McDaniel, MD 21647
    9190 Pennywhistle Dr, McDaniel, MD 21647
    /2

    $1,300,000 Coming Soon

    • 4 Beds
    • 3 Baths
    • 3,315 Sq Ft

    9190 Pennywhistle Dr, McDaniel, MD 21647

    George Howard George Howard Real Estate Inc.

    9190 Pennywhistle Dr, McDaniel, MD 21647
  • 106 Boundary Ln, Saint Michaels, MD 21663
    106 Boundary Ln, Saint Michaels, MD 21663
    106 Boundary Ln, Saint Michaels, MD 21663
    /58

    $595,000

    • 3 Beds
    • 2 Baths
    • 1,490 Sq Ft

    106 Boundary Ln, Saint Michaels, MD 21663

    Nestled in the heart of St. Michaels, this beautifully maintained one-level home offers 2–3 bedrooms and 2 full bathrooms. A welcoming stone front porch leads to a foyer that opens into a bright, airy interior filled with natural light and wide plank wood floors throughout. The updated kitchen features quartz countertops, a farmhouse sink, tile backsplash and stainless steel appliances. Just off

    Kim Crouch Ozman Benson & Mangold, LLC

    106 Boundary Ln, Saint Michaels, MD 21663
  • 9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
    /60

    $480,000

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663

    This stunning three-bedroom, three-bath home is, without question, the nicest townhome in the very desirable Martingham Quail Hollow community. The home has been extensively upgraded with exquisite finishes, and it enjoys a beautiful, landscaped setting that backs onto the Links at Perry Cabin Golf Course. The spacious great room opens to the charming, landscaped patio with an automatic awning

    Eugene Smith TTR Sotheby's International Realty

    9529 Quail Hollow Dr Unit 503, Saint Michaels, MD 21663
  • 7896 Hart Glen Ct, Saint Michaels, MD 21663
    7896 Hart Glen Ct, Saint Michaels, MD 21663
    7896 Hart Glen Ct, Saint Michaels, MD 21663
    /70

    $795,000 Open Sat 12PM - 2PM

    • 4 Beds
    • 2.5 Baths
    • 3,038 Sq Ft

    7896 Hart Glen Ct, Saint Michaels, MD 21663

    Located at the end of a quiet cul-de-sac in the desirable Back Creek Landing neighborhood of St. Michaels, Maryland, this beautifully maintained home offers privacy, quality upgrades, and a fantastic Eastern Shore lifestyle. The large, inviting front porch sets the tone as you arrive. Step inside and you are welcomed by a warm, light-filled interior that immediately feels like home. The floor

    Kathleen Coale Benson & Mangold, LLC

    7896 Hart Glen Ct, Saint Michaels, MD 21663
  • 8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
    /60

    $8,495,000

    • 6 Beds
    • 11 Baths
    • 17,402 Sq Ft

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663

    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,

    Doc Keane Washington Fine Properties, LLC

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • 27791 Villa Rd, Easton, MD 21601
    27791 Villa Rd, Easton, MD 21601
    27791 Villa Rd, Easton, MD 21601
    /8

    $3,500,000

    • 5 Beds
    • 5.5 Baths
    • 4,848 Sq Ft

    27791 Villa Rd, Easton, MD 21601

    PROFESSIONAL PICTURES COMING SOON! This stunning 5-bedroom, 5.5-bath coastal retreat is set on over 5 acres along the serene shores of Glebe Creek. A shared, tree-lined driveway leads to a beautifully landscaped yard featuring paver walkways, a detached two-car garage with guest quarters above—conveniently connected to the main house by a covered walkway—and a separate cottage with full bath and

    Clifford Meredith Meredith Fine Properties

    27791 Villa Rd, Easton, MD 21601
  • 6815 Bellevue Rd, Royal Oak, MD 21662
    6815 Bellevue Rd, Royal Oak, MD 21662
    6815 Bellevue Rd, Royal Oak, MD 21662
    /24

    $349,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft

    6815 Bellevue Rd, Royal Oak, MD 21662

    RENOVATED HOME JUST 3 MILES FROM HISTORIC ST MICHAELS This newly renovated 3 bedroom, 2 bathroom residence is conveniently located in the charming village of Royal Oak - only a few minutes to St Michaels and just 6 miles from the city of Easton. Built in 1900, this 1,238 square foot dwelling has been tastefully remodeled to offer both comfort and quality.When you step inside, you will instantly

    Peter Frevel Benson & Mangold, LLC

    6815 Bellevue Rd, Royal Oak, MD 21662
  • 103 W Marengo St, Saint Michaels, MD 21663
    103 W Marengo St, Saint Michaels, MD 21663
    103 W Marengo St, Saint Michaels, MD 21663
    /10

    $600,000

    • 2 Beds
    • 1.5 Baths
    • 1,209 Sq Ft

    103 W Marengo St, Saint Michaels, MD 21663

    Quintessential St. Michaels Charm! Nestled in the heart of this historic and picturesque waterfront town, this adorable cedar shake home is straight out of Nantucket! With two bedrooms, one and a half baths, and classic coastal curb appeal, this home sits on a generous fenced lot backing up to alley way—perfect for outdoor entertaining, gardening, or simply soaking in the Chesapeake breeze.

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    103 W Marengo St, Saint Michaels, MD 21663
  • 27564 Saint Michaels Rd, Easton, MD 21601
    27564 Saint Michaels Rd, Easton, MD 21601
    27564 Saint Michaels Rd, Easton, MD 21601
    /28

    $540,000

    • 3 Beds
    • 2 Baths
    • 1,456 Sq Ft

    27564 Saint Michaels Rd, Easton, MD 21601

    Just Listed | 27564 Saint Michaels Road, Easton, MDWelcome to this beautifully updated three bedroom, two full bathrooms Eastern Shore gem, perfectly nestled on a serene TWO acres just minutes from both downtown Easton and St. Michaels. This home blends timeless charm with modern upgrades, including brand new stainless steel appliances (with manufacturer warranties), a brand new HVAC system,

    Erene Katris Benson & Mangold, LLC

    27564 Saint Michaels Rd, Easton, MD 21601
  • 5793 Tilghman Island Rd, Tilghman, MD 21671
    5793 Tilghman Island Rd, Tilghman, MD 21671
    5793 Tilghman Island Rd, Tilghman, MD 21671
    /11

    $289,000

    • 3 Beds
    • 1 Bath
    • 810 Sq Ft

    5793 Tilghman Island Rd, Tilghman, MD 21671

    Local Skipjack Captain Bart Murphy and wife Florence raised their family in this sweet Island home. Conveinently located close to Dogwood Harbor and fine restaurants. Cozy oil heat was perfect after a cold day on the Bay. This house had many seafood dinners and is waiting for the next owners to enjoy Island life. There is a small attached lot that is included.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    5793 Tilghman Island Rd, Tilghman, MD 21671
  • 6375 Bozman Neavitt Rd, Neavitt, MD 21652
    6375 Bozman Neavitt Rd, Neavitt, MD 21652
    6375 Bozman Neavitt Rd, Neavitt, MD 21652
    /31

    $350,000

    • 1 Bed
    • 2 Baths
    • 1,100 Sq Ft

    6375 Bozman Neavitt Rd, Neavitt, MD 21652

    Enjoy peaceful water views and classic Eastern Shore charm in this well-maintained home in the village of Neavitt, just minutes from St. Michaels. Step into the open-concept great room, where hardwood floors, soaring ceilings, and a pellet stove create a warm and inviting living space. Floor-to-ceiling windows capture stunning views of Duck Cove and lead directly to a large deck—ideal for

    Wink Cowee Benson & Mangold, LLC

    6375 Bozman Neavitt Rd, Neavitt, MD 21652
  • 7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    /85

    $3,250,000

    • 6 Beds
    • 4.5 Baths
    • 4,352 Sq Ft

    7421 Quaker Neck Rd, Bozman, MD 21612

    For the first time in over half a century, an extraordinary opportunity presents itself—a chance to claim a piece of history that has remained in the loving stewardship of one family for generations. Nestled on over 13 private acres, this breathtaking 6-bedroom, 4.5-bath waterfront estate offers an unparalleled living experience with 4,352 square feet of main living space plus an additional 1,500

    Barbara McCaffrey Redfin Corp

    7421 Quaker Neck Rd, Bozman, MD 21612
  • 400 Railroad Ave, Saint Michaels, MD 21663
    400 Railroad Ave, Saint Michaels, MD 21663
    400 Railroad Ave, Saint Michaels, MD 21663
    /35

    $575,000

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft

    400 Railroad Ave, Saint Michaels, MD 21663

    Nestled on a desirable corner lot in the historic waterfront town of St. Michaels, this 1930 bungalow blends classic architecture with modern comforts. Ideally located just a short distance from the Chesapeake Bay Maritime Museum, shops, restaurants, and the harbor, this home offers the best of in-town living. A spacious front porch welcomes you - perfect for morning coffee or casual

    Monica Penwell TTR Sotheby's International Realty

    400 Railroad Ave, Saint Michaels, MD 21663
  • 901 S Talbot St, Saint Michaels, MD 21663
    901 S Talbot St, Saint Michaels, MD 21663
    901 S Talbot St, Saint Michaels, MD 21663
    /51

    $659,000

    • 3 Beds
    • 2 Baths
    • 1,660 Sq Ft

    901 S Talbot St, Saint Michaels, MD 21663

    St. Michaels English style Cottage – This Adorable 3-bedroom 2 bath home offers a first-floor primary bedroom, updated kitchen and baths, formal dining room, rear sunroom, and a fenced side and rear patio thoughtfully landscaped. The yard is irrigated. Long sweeping gables and roof peaks, prominent front facing chimney and entrance vestibule standout as architectural features of this 1930’s

    Barbara Watkins Benson & Mangold, LLC

    901 S Talbot St, Saint Michaels, MD 21663
  • 10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    /91

    $8,875,000

    • 7 Beds
    • 7.5 Baths
    • 10,240 Sq Ft

    10770 Rich Neck Rd, Claiborne, MD 21624

    Incredible 300+ acre landmark estate located 5 miles beyond St. Michaels. Over FOUR MILES OF SHORELINE on Eastern Bay, the Miles River and Tilghman Creek. Deep protected anchorage. High land. Sandy beaches. Very livable 10,000+ sq ft home that underwent two-year renovation 2005/2006. 13 ft ceilings on first story and almost10 ft on second story. Formal and informal living areas. Chef's kitchen

    Robert G. Shannahan Shoreline Realty

    10770 Rich Neck Rd, Claiborne, MD 21624
  • 6976 Travelers Rest Cir, Easton, MD 21601
    6976 Travelers Rest Cir, Easton, MD 21601
    6976 Travelers Rest Cir, Easton, MD 21601
    /52

    $2,700,000

    • 3 Beds
    • 3 Baths
    • 7,949 Sq Ft

    6976 Travelers Rest Cir, Easton, MD 21601

    Welcome to Soleil on the Bay! Nestled on nearly 7 acres along the scenic Maxmore Creek—just off the Tred Avon River—this exceptional west-facing waterfront property offers the most gorgeous sunsets providing the perfect blend of privacy, natural beauty, and endless potential. Ideally located between Easton and St. Michaels, it provides easy access to the best of Maryland’s Eastern Shore.Enter

    Clifford Meredith Meredith Fine Properties

    6976 Travelers Rest Cir, Easton, MD 21601
  • 9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    9171 Deepwater Point Rd, Saint Michaels, MD 21663
    /41

    $1,795,000

    • 4 Beds
    • 3.5 Baths
    • 4,102 Sq Ft

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Deepwater Retreat, an extraordinary 6+/- acre waterfront property overlooking the Links at Perry Cabin Golf Course with direct access to the Long Haul Creek and Miles River. Just moments to downtown Saint Michaels, fine dining, shopping, and entertainment, this stunning makeover offers 4,100 +/- sq. ft. of single-story living designed for endless indoor/outdoor entertainment. This

    Craig Linthicum Benson & Mangold, LLC

    9171 Deepwater Point Rd, Saint Michaels, MD 21663
  • 9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
    /41

    $439,000

    • 3 Beds
    • 2 Baths
    • 1,752 Sq Ft

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663

    DESIRABLE END UNIT TOWNHOME WITH 1ST FLOOR BEDROOM AND BATH, VERY PRIVATE VIEW OF THE GOLF COURSE PLANTINGS AND A SMALL WATER VIEW FROM THE 2ND FLOOR DECK OFF THE PRIMARY BEDROOM.THE KITCHEN HAS BEEN RENOVATED, WHITE CABINETS WITH STONE COUNTERTOPS, A LARGE GLASS DOOR OPENS TO THE TILE FLOORED SUN ROOM FROM THE KITCHEN AND FROM THE DINING ROOM, LETTING THE LIGHT FILL THE UNIT. THE SECOND

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    9545 Quail Hollow Dr Unit 206, Saint Michaels, MD 21663
  • 9501 Unionville Rd, Easton, MD 21601
    9501 Unionville Rd, Easton, MD 21601
    9501 Unionville Rd, Easton, MD 21601
    /31

    $225,000

    • 2 Beds
    • 1 Bath
    • 640 Sq Ft

    9501 Unionville Rd, Easton, MD 21601

    Nestled in a serene country setting, this charming 2 bedroom /1 bathroom rancher offers the perfect blend of privacy and comfort. A beautifully stoned, long driveway leads you to the home, surrounded by a sprawling yard that offers plenty of space to enjoy the outdoors. The private driveway ensures seclusion, creating an intimate retreat from the hustle and bustle of daily life. A delightful

    Dana Miller Worthington Realty Group, LLC

    9501 Unionville Rd, Easton, MD 21601
  • 4957 Bar Neck Rd, Tilghman, MD 21671
    4957 Bar Neck Rd, Tilghman, MD 21671
    4957 Bar Neck Rd, Tilghman, MD 21671
    /45

    $895,000 Open Sun 11AM - 1PM

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft

    4957 Bar Neck Rd, Tilghman, MD 21671

    Don't miss out on this beautifully landscaped yard with a deck and pool, perfect for entertaining and enjoying the serene water views. This gorgeous two-story traditional home features three bedrooms and three baths, offering the perfect location to enjoy the picturesque views of Black Walnut Creek and the Chesapeake Bay.The current owners have meticulously maintained the property and spent a

    Lori Neske Coldwell Banker Realty

    4957 Bar Neck Rd, Tilghman, MD 21671
  • 108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    108 Miles, Saint Michaels, MD 21663
    /18

    $594,000

    • Land
    • 0.55 Acre
    • $1,080,000 per Acre

    108 Miles, Saint Michaels, MD 21663

    Build your dream home on this one-of-a- kind, half+ acre (24,082 sf) wooded lot in the heart ofSaint Michaels. Offering a tranquil, park-like setting, this rare property provides both privacy andconvenience, a five-minute walk to the town’s charming restaurants, coffeeshops, events and shopping. Located just outside the historic district line, this unusuallylarge lot (3 times the

    Jana Meredith Meredith Fine Properties

    108 Miles, Saint Michaels, MD 21663
  • 8858 Howeth Rd, Wittman, MD 21676
    8858 Howeth Rd, Wittman, MD 21676
    8858 Howeth Rd, Wittman, MD 21676
    /43

    $374,000

    • 2 Beds
    • 2 Baths
    • 1,222 Sq Ft

    8858 Howeth Rd, Wittman, MD 21676

    Welcome to this delightful cottage nestled in the historic village of Wittman. Situated on a charming corner lot, this home has been thoughtfully updated while preserving its historic character. The second level boasts a private en-suite primary bedroom, complete with a cozy nook ideal for a home office. On the main level, you’ll find a second bedroom, a versatile den or craft room with built-in

    Monica Penwell TTR Sotheby's International Realty

    8858 Howeth Rd, Wittman, MD 21676
  • 27047 Presquile Rd, Easton, MD 21601
    27047 Presquile Rd, Easton, MD 21601
    27047 Presquile Rd, Easton, MD 21601
    /74

    $3,690,000

    • 4 Beds
    • 4 Baths
    • 6,374 Sq Ft

    27047 Presquile Rd, Easton, MD 21601

    Originally constructed in 1970 and extensively renovated in 2018, the main residence embodies refined sophistication and modern comfort. The open-concept floor plan seamlessly connects living, dining, and kitchen spaces, highlighted by high-quality hardwood floors, custom built-ins, and shiplap detailing that harmonize timeless charm with contemporary luxury. A chef’s kitchen with premium custom

    Coard Benson Benson & Mangold, LLC

    27047 Presquile Rd, Easton, MD 21601

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