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Homes for Sale near St. Michaels Middle/High School

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  • 21424 Wharf Rd, Tilghman, MD 21671
    21424 Wharf Rd, Tilghman, MD 21671
    21424 Wharf Rd, Tilghman, MD 21671
    /47

    $399,000

    • 2 Beds
    • 1 Bath
    • 1,464 Sq Ft

    21424 Wharf Rd, Tilghman, MD 21671

    **WELCOME TO YOUR VERY OWN SLICE OF "MARYLAND EASTERN SHORE PARADISE”! **A RARE OFFERING! A TRUE STORYBOOK CHARMER! ABSOLUTELY ENCHANTING, UPDATED & EXPANDED CIRCA 1900 VICTORIAN FARMHOUSE LOCATED ON PREMIER STREET IN SOUGHT AFTER "HISTORIC TILGHMAN ISLAND"; A WATER & NATURE ENTHUSIASTS DELIGHT WHICH PROUDLY BOASTS THE LARGEST WORKING SKIPJACK FLEET! COZY & INVITING, YET ELEGANT &

    Agent Photo

    Angela Simonelli

    Compass

    (410) 200-0414

    21424 Wharf Rd, Tilghman, MD 21671
  • 205 E Chew Ave, Saint Michaels, MD 21663
    205 E Chew Ave, Saint Michaels, MD 21663
    205 E Chew Ave, Saint Michaels, MD 21663
    /28

    $1,275,000

    • 2 Beds
    • 1.5 Baths
    • 1,780 Sq Ft

    205 E Chew Ave, Saint Michaels, MD 21663

    The Arthur K. Easter House, St. Michaels, MarylandFrom the moment you arrive, it is clear: this is no ordinary house. Located on one of St. Michaels’ most sought-after streets, the circa 1889 Arthur K. Easter House seems to have stepped from the pages of a storybook—one filled with golden light, quiet elegance, and a sense of belonging. This stylish historic home was relocated to its current

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (866) 771-9340

    205 E Chew Ave, Saint Michaels, MD 21663
  • 8061 N Fork Blvd, Easton, MD 21601
    8061 N Fork Blvd, Easton, MD 21601
    8061 N Fork Blvd, Easton, MD 21601
    /34

    $899,000

    • 4 Beds
    • 2.5 Baths
    • 3,033 Sq Ft

    8061 N Fork Blvd, Easton, MD 21601

    Welcome to 8061 N Fork Boulevard in Easton’s sought-after waterfront community! This 4-bedroom 2.5 bath modern home offers over 3,000 sq.ft. of living with an open floor plan, gas burning fireplace and finished south-facing sunroom, as well as a south-facing living room and kitchen. The kitchen is equipped with stainless steel appliances. There is also a large first floor primary suite. Built

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 657-5564

    8061 N Fork Blvd, Easton, MD 21601
  • 222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    222 E Chestnut St, Saint Michaels, MD 21663
    /38

    $2,250,000 Open Sat 11AM - 3PM

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

    222 E Chestnut St, Saint Michaels, MD 21663

    A unique opportunity to own a completely renovated home in the heart of town featuring four deep-water, dedicated boat slips. Located at the end of one of the most coveted, tree-lined streets in St. Michaels, this home is surrounded by beautifully restored historic properties and offers incredible views of St. Michaels Harbor. The current owners have thoughtfully renovated this 3-bedroom,

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (844) 651-2546

    222 E Chestnut St, Saint Michaels, MD 21663
  • 21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    21472 Willey Rd, Tilghman, MD 21671
    /10

    $80,000

    • Land
    • 0.3 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
  • 0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    0 Sinclair Rd, Tilghman Island, MD 21671
    /12

    $75,000

    • Land
    • 0.3 Acre
    • $250,000 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
  • 0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
    0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
    0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
    /5

    $1,250,000

    • Land
    • 47.52 Acres
    • $26,305 per Acre

    0 Unionville Rd Unit MDTA2008824, Easton, MD 21601

    Presenting 47+ acres of stunning land just minutes from Easton, perfectly positioned at the intersectionof Unionville Road and Miles River Road, extending along Anchorage Road. This expansive property iscurrently leased for farming and hunting, offering both income potential and recreational opportunities.While it has not been perc tested, the property holds potential for multiple

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    (443) 205-7213

    0 Unionville Rd Unit MDTA2008824, Easton, MD 21601
  • 27460 Rest Cir, Easton, MD 21601
    27460 Rest Cir, Easton, MD 21601
    27460 Rest Cir, Easton, MD 21601
    /48

    $599,999

    • 2 Beds
    • 2 Baths
    • 1,696 Sq Ft

    27460 Rest Cir, Easton, MD 21601

    Welcome to this beautifully updated solid-brick home on Rest Circle, set on a serene .86-acre lot with lush landscaping, a fenced yard, a paved driveway with carport and huge detached 3 car garage. Inside, you’ll find a thoughtfully designed one-level floor plan featuring a first-floor primary suite with a brand-new full ensuite bath, complete with a gorgeous walk-in shower. Originally a

    Agent Photo

    Penny Hollis

    Keller Williams Select Realtors of Annapolis

    (443) 516-9194

    27460 Rest Cir, Easton, MD 21601
  • 5440 Anchor Rd, Tilghman, MD 21671
    5440 Anchor Rd, Tilghman, MD 21671
    5440 Anchor Rd, Tilghman, MD 21671
    /32

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    5440 Anchor Rd, Tilghman, MD 21671

    TILGHMAN ISLAND: Discover your dream home in the charming, water-privileged community of Tilghman Beach. This stunning ranch-style home, built in 2018, offers modern conveniences and one-level living at its finest, perfect for those seeking a serene lifestyle by the water.Key Features:Spacious Open Floor Plan: Enjoy seamless living with a large combination living and dining area,

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 657-6713

    5440 Anchor Rd, Tilghman, MD 21671
  • 6827 Bellevue Rd, Royal Oak, MD 21662
    6827 Bellevue Rd, Royal Oak, MD 21662
    6827 Bellevue Rd, Royal Oak, MD 21662
    /32

    $385,000

    • 3 Beds
    • 1.5 Baths
    • 1,363 Sq Ft

    6827 Bellevue Rd, Royal Oak, MD 21662

    Charming One-Story Royal Oak Retreat – Minutes from St. MichaelsWelcome to this impeccably maintained 3-bedroom, 1.5-bath home in the heart of Royal Oak, just minutes from the shops, restaurants, and waterfront of historic St. Michaels. This charming one-story residence offers beautiful hardwood floors, an updated full bath, and a warm, inviting layout perfect for everyday living or

    Agent Photo

    Angela Simonelli

    Compass

    (410) 200-0414

    6827 Bellevue Rd, Royal Oak, MD 21662
  • 6135 Summit St, Tilghman, MD 21671
    6135 Summit St, Tilghman, MD 21671
    6135 Summit St, Tilghman, MD 21671
    /31

    $399,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    6135 Summit St, Tilghman, MD 21671

    Welcome to your Eastern Shore getaway, located at 6135 Summit Street, Tilghman, Maryland. This charming property is just a short walk from Tilghman Island's best waterfront attractions, including two marinas and three excellent dining options. This two-bedroom, one-bath home reflects pride of ownership and has been well maintained, making it ready for you to enjoy a slower pace of life on

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 593-3451

    6135 Summit St, Tilghman, MD 21671
  • 21749 Camper Cir, Tilghman, MD 21671
    21749 Camper Cir, Tilghman, MD 21671
    21749 Camper Cir, Tilghman, MD 21671
    /25

    $295,000

    • 3 Beds
    • 1 Bath
    • 1,224 Sq Ft

    21749 Camper Cir, Tilghman, MD 21671

    A fantastic opportunity awaits at 21749 Camper Circle in Tilghman, Maryland. This home is perfect for first-time buyers or investors looking for great value at an affordable price. It features central heating and air conditioning, three spacious bedrooms, and one full bathroom. Enjoy a large sunroom with tile flooring that is conveniently located next to the kitchen. The hardwood floors

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 498-8659

    21749 Camper Cir, Tilghman, MD 21671
  • 100 Mulberry St, St. Michaels, MD 21663
    100 Mulberry St, St. Michaels, MD 21663
    100 Mulberry St, St. Michaels, MD 21663
    /6

    $950,000

    • Studio
    • 4,172 Sq Ft

    100 Mulberry St, St. Michaels, MD 21663

    Exceptional location with ample off-street parking—this spacious and well-maintained triplex is an ideal investment in the highly desirable St. Michaels community. The first floor features a spacious 3-bedroom, 3.5-bath unit with a large kitchen, a formal dining room with a cozy wood-burning fireplace, a generous living room, and a private laundry room.Upstairs, the second floor features two

    Agent Photo

    Tracy Higgs-Wagner

    Meredith Fine Properties

    (877) 846-5106

    100 Mulberry St, St. Michaels, MD 21663
  • 5820 Tilghman Beach Dr, Tilghman, MD 21671
    5820 Tilghman Beach Dr, Tilghman, MD 21671
    5820 Tilghman Beach Dr, Tilghman, MD 21671
    /32

    $795,000

    • 2 Beds
    • 1 Bath
    • 1,776 Sq Ft

    5820 Tilghman Beach Dr, Tilghman, MD 21671

    Welcome to 5820 Tilghman Beach Drive. Come experience the most beautiful sunsets the Chesapeake Bay has to offer. Centrally located on Tilghman Island this little slice of paradise is ready for its new owners to make their dream of waterfront living come true.Home offers two bedrooms and one full bath, hardwood floors, recently remodeled kitchen, encapsuled crawl space, Central heat and air,

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 927-1165

    5820 Tilghman Beach Dr, Tilghman, MD 21671
  • 5379 Anchor Rd, Tilghman, MD 21671
    5379 Anchor Rd, Tilghman, MD 21671
    5379 Anchor Rd, Tilghman, MD 21671
    /56

    $560,000

    • 2 Beds
    • 2.5 Baths
    • 1,232 Sq Ft

    5379 Anchor Rd, Tilghman, MD 21671

    Bay Breezes & Beautiful Views: Your Tilghman Island HavenWaterview Living with Room to Breathe on Maryland's Eastern ShoreStep into the good life at 5379 Anchor Road, where Chesapeake Bay magic meets everydaycomfort. This charming home in Tilghman's friendly beach neighborhood sits just ashort stroll from the community beach where neighbors gather and memories are

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 206-6165

    5379 Anchor Rd, Tilghman, MD 21671
  • 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

    $174,900

    • Land
    • 2.49 Acres
    • $70,241 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
  • 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

    $1,695,000

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

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Micheals Retreat, an extraordinary 6+/- acre property overlooking the Links at Perry Cabin Golf Course with direct water access to 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
  • 28092 Glebe Rd, Easton, MD 21601
    28092 Glebe Rd, Easton, MD 21601
    28092 Glebe Rd, Easton, MD 21601
    /39

    $3,275,000

    • 7 Beds
    • 10 Baths
    • 7,077 Sq Ft

    28092 Glebe Rd, Easton, MD 21601

    Miles Away on Murphy’s Point – Discover an unparalleled waterfront retreat at 28092 Glebe Rd, Easton, MD, nestled on approximately ±2.7 picturesque acres. Thoughtfully designed for entertaining, relaxation, and convenient living, this luxurious estate offers expansive indoor and outdoor spaces, exceptional waterfront amenities, and easy access to nearby towns, beaches, and metropolitan

    Coard Benson Benson & Mangold, LLC

    28092 Glebe Rd, Easton, MD 21601
  • 408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    /82

    $775,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 1,957 Sq Ft

    408 Spinnaker Ln, Saint Michaels, MD 21663

    This immaculate 4 bedroom, 2.5 bath home was built in 2022 and has been thoughtfully enhanced with numerous upgrades. The owners added luxury vinyl plank flooring to the second level, Hunter Douglas plantation shutters with independent top and bottom operation, recessed lighting upstairs, and a high-end full-size Electrolux washer and dryer. Additional features include a smart home system with

    Christie Bishop Northrop Realty

    408 Spinnaker Ln, Saint Michaels, MD 21663
  • 7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    7421 Quaker Neck Rd, Bozman, MD 21612
    /85

    $2,750,000

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

    7421 Quaker Neck Rd, Bozman, MD 21612

    Mortgage savings may be available for buyers of this listing. 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

    Barbara McCaffrey Redfin Corp

    7421 Quaker Neck Rd, Bozman, MD 21612
  • 22769 Almost Neavitt Rd, Bozman, MD 21612
    22769 Almost Neavitt Rd, Bozman, MD 21612
    22769 Almost Neavitt Rd, Bozman, MD 21612
    /65

    $859,000

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

    22769 Almost Neavitt Rd, Bozman, MD 21612

    Mortgage savings may be available for buyers of this listing.PUBLIC SEWER COMING THIS YEAR! 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

    Barbara McCaffrey Redfin Corp

    22769 Almost Neavitt Rd, Bozman, MD 21612
  • 9361 Woodstock Ln, Easton, MD 21601
    9361 Woodstock Ln, Easton, MD 21601
    /2

    $995,000

    • Land
    • 5.48 Acres
    • $181,569 per Acre

    9361 Woodstock Ln, Easton, MD 21601

    Quiet country setting can be yours with this 5.5 +/- acre waterfront lot located in the Woodstock Farm community on Goldsborough Creek is perc approved for 6 bedrooms! Located just minutes to downtown Easton and all of the amenities Easton has to offer from shopping to dining, entertainment at the Avalon Theatre, and the convenience of Easton's Jetport.

    Chuck Jr. Benson and Mangold

    9361 Woodstock Ln, Easton, MD 21601
  • 22540 Hardcastle Ln, Bozman, MD 21612
    22540 Hardcastle Ln, Bozman, MD 21612
    22540 Hardcastle Ln, Bozman, MD 21612
    /86

    $2,998,000

    • 5 Beds
    • 6.5 Baths
    • 4,711 Sq Ft

    22540 Hardcastle Ln, Bozman, MD 21612

    The Ultimate Harris Creek Retreat—Unrivaled Views. Room to Spread Out. Sunsets You’ll Never Forget. Welcome to your family’s forever getaway: a fully renovated waterfront estate on 2.4 acres with 240+ feet of direct water frontage. Perfectly positioned for stunning western views over Harris Creek, this exceptional property includes a reimagined main residence, newly constructed three-bay

    Mark Meyerdirk Urban Brokers, LLC

    22540 Hardcastle Ln, Bozman, MD 21612
  • 8534 Northbend Rd, Easton, MD 21601
    8534 Northbend Rd, Easton, MD 21601
    8534 Northbend Rd, Easton, MD 21601
    /6

    $989,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,394 Sq Ft

    8534 Northbend Rd, Easton, MD 21601

    Pictures will be taken end of week of 10/6-10/11. Discover timeless charm and modern luxury in this beautifully appointed 4-bedroom, 2.5-bathroom Colonial nestled on 2.2 acres between the coveted towns of St. Michaels and Easton. This farmhouse-style gem features a seamless blend of hardwood and luxury vinyl flooring, creating a warm and inviting atmosphere throughout.The heart of the

    Jana Meredith Meredith Fine Properties

    8534 Northbend Rd, 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
    /40

    $1,635,000

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

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Michaels Retreat—an extraordinary 6-acre property overlooking the Links at Perry Cabin Golf Course with direct water access to Long Haul Creek and the Miles River. Just minutes from downtown Saint Michaels, this stunningly renovated residence offers over 4,100 sq. ft. of one-level living, thoughtfully designed for effortless indoor and outdoor entertaining. Inside, expansive

    Laura Carney TTR Sotheby's International Realty

    9171 Deepwater Point Rd, Saint Michaels, MD 21663
  • 6060 Elston Shore Rd, Neavitt, MD 21652
    6060 Elston Shore Rd, Neavitt, MD 21652
    6060 Elston Shore Rd, Neavitt, MD 21652
    /43

    $2,695,000

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    6060 Elston Shore Rd, Neavitt, MD 21652

    Discover an extraordinary Eastern Shore escape where privacy meets luxury. This 10.6± acre property is improved by a custom home that has been completely renovated down to the frame, essentially making this a new home. The completely private lot boasts 1,500± feet of waterfrontage with a private pier,with unparallelled southwest views over Harris creek to the Choptank and beyond. Nearly

    Chuck Mangold Benson & Mangold, LLC

    6060 Elston Shore Rd, Neavitt, MD 21652
  • 23869 New Land Dr, St. Michaels, MD 21663
    23869 New Land Dr, St. Michaels, MD 21663
    23869 New Land Dr, St. Michaels, MD 21663
    /69

    $1,950,000

    • 3 Beds
    • 2 Baths
    • 2,717 Sq Ft

    23869 New Land Dr, St. Michaels, MD 21663

    Welcome to Heron Cove Farm, a beautiful waterfront paradise situated on the banks of Broad Creek, just outside of Historic Saint Michaels, MD. This masterfully renovated home offers the convenience of one level living in a private setting of over 15 acres creating the feel of a peaceful escape, yet only two miles from the restaurants, shops and social network of town. Whether you enjoy relaxing

    Keith Hensley Meredith Fine Properties

    23869 New Land Dr, St. Michaels, MD 21663
  • 21368 Fairbank Cir, Tilghman, MD 21671
    21368 Fairbank Cir, Tilghman, MD 21671
    21368 Fairbank Cir, Tilghman, MD 21671
    /66

    $1,150,000

    • 4 Beds
    • 3 Baths
    • 3,552 Sq Ft

    21368 Fairbank Cir, Tilghman, MD 21671

    Experience waterfront living in the historic community of Fairbank on Tilghman Island. This home offers timeless character and sweeping views of Black Walnut Cove. Built in 1900 with later additions, you'll find multiple decks, porches, and patios, along with a unique circular staircase leading to the second-floor porch, enhancing its architectural charm. Inside, the gourmet kitchen and family

    Alicia Gannon Dulin Benson & Mangold, LLC

    21368 Fairbank Cir, Tilghman, MD 21671
  • 5837 Irish Creek Rd, Royal Oak, MD 21662
    5837 Irish Creek Rd, Royal Oak, MD 21662
    5837 Irish Creek Rd, Royal Oak, MD 21662
    /70

    $3,095,000

    • 4 Beds
    • 3.5 Baths
    • 3,088 Sq Ft

    5837 Irish Creek Rd, Royal Oak, MD 21662

    Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation

    Robert Lacaze TTR Sotheby's International Realty

    5837 Irish Creek Rd, Royal Oak, MD 21662
  • 8453 Ingleton Rd, Easton, MD 21601
    8453 Ingleton Rd, Easton, MD 21601
    8453 Ingleton Rd, Easton, MD 21601
    /87

    $925,000

    • 4 Beds
    • 3.5 Baths
    • 4,052 Sq Ft

    8453 Ingleton Rd, Easton, MD 21601

    Nestled on a beautiful 2 + acre lot, this exquisite contemporary residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. This is an artists and art lovers dream house. Built in 2004, the home showcases stunning stone and stucco construction, exuding timeless elegance while providing modern amenities. Step inside to discover an expansive open

    Carolina Barksdale Benson & Mangold, LLC

    8453 Ingleton Rd, Easton, MD 21601
  • 107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    107 E Chestnut St, Saint Michaels, MD 21663
    /65

    $1,295,000

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

    107 E Chestnut St, Saint Michaels, MD 21663

    St. Michaels charm in this Circa 1870 Certified Plaque home, although historical data reflects original construction between 1805-1820.Updates include plumbing ,wiring, New upstairs HVAC, encapsulated crawl space, kitchen ,upgraded light fixtures, motorized window shades and many architectural details, freshly painted in 2024 . Recently upgraded Primary bedroom window seats with cushions,

    Robert Fitton Meredith Fine Properties

    107 E Chestnut St, Saint Michaels, MD 21663
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /99

    $1,249,000

    • 3 Beds
    • 3 Baths
    • 1,612 Sq Ft

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    St Michaels is just 2 miles away... Oakwood park known to be a slice of Eastern Shore heaven. This one story cottage with a dreamy porch and carriage house serves as the owners get away and vacation rental. Features are riprap shoreline and a boat ramp, the Carriage house with second floor guest and a balcony overlooking San Domingo Creek, a 2 car garage with workshop, laundry space and

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
  • 6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    6670 Tilghman Island Rd, Sherwood, MD 21665
    /64

    $1,299,000

    • 3 Beds
    • 3 Baths
    • 3,853 Sq Ft

    6670 Tilghman Island Rd, Sherwood, MD 21665

    Waterfront home situated on Back Creek in Sherwood, offering direct access to the Chesapeake Bay and Choptank Rivers. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting.

    Larry Brennan TTR Sotheby's International Realty

    6670 Tilghman Island Rd, Sherwood, MD 21665
  • 21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    21477 Island Club Rd, Tilghman, MD 21671
    /50

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 3,040 Sq Ft

    21477 Island Club Rd, Tilghman, MD 21671

    Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    21477 Island Club Rd, Tilghman, MD 21671
  • 6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    6050 Sunset Ln, Tilghman, MD 21671
    /74

    $1,275,000

    • 3 Beds
    • 3 Baths
    • 3,232 Sq Ft

    6050 Sunset Ln, Tilghman, MD 21671

    Exquisitely designed renovation incorporating high end finishes makes this waterfront 3BR, 3B cottage the perfect retreat! Large great room w/dining area, fireplace & multiple seating areas gives you ample spaces to enjoy the broad, westerly views of the bay. The gourmet kitchen & pantry is a chef's dream. Screen room, private pier, separate garage w/ guest house.

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    6050 Sunset Ln, Tilghman, MD 21671
  • 22860 Middle Point Rd, Neavitt, MD 21652
    22860 Middle Point Rd, Neavitt, MD 21652
    22860 Middle Point Rd, Neavitt, MD 21652
    /57

    $1,150,000

    • 3 Beds
    • 2 Baths
    • 2,642 Sq Ft

    22860 Middle Point Rd, Neavitt, MD 21652

    Welcome to this architecturally designed waterfront retreat, thoughtfully created to capture broad, breathtaking views and harmonize with its natural surroundings. Set in a quiet village near historic St. Michaels, this home offers a rare blend of tranquility, comfort, and convenience—just minutes from a public park and landing. Inside, the home features 3 spacious bedrooms, an office, and

    Wink Cowee Benson & Mangold, LLC

    22860 Middle Point Rd, Neavitt, MD 21652
  • 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
  • 5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    /83

    $1,200,000

    • 5 Beds
    • 2.5 Baths
    • 4,214 Sq Ft

    5520 Leeward Ln, Tilghman, MD 21671

    Welcome to 5520 Leeward Lane, a private waterfront estate tucked away at the end of a quiet, tree-lined drive on Tilghman Island—a rare opportunity to own a stunning piece of Maryland’s Eastern Shore. This expansive home features panoramic water views from almost every room and delivers the ultimate blend of luxury, comfort, and natural beauty. The grand foyer sets a graceful tone, leading into a

    Samantha Jackson Keller Williams Realty

    5520 Leeward Ln, Tilghman, MD 21671
  • 9235 Martingham Dr, Saint Michaels, MD 21663
    9235 Martingham Dr, Saint Michaels, MD 21663
    9235 Martingham Dr, Saint Michaels, MD 21663
    /30

    $699,000

    • 3 Beds
    • 3 Baths
    • 2,646 Sq Ft

    9235 Martingham Dr, Saint Michaels, MD 21663

    Set in one of St. Michaels’ most sought-after waterfront communities, this 3-bedroom, 3-bath Colonial offers a formal dining room, sitting room, living room with gas fireplace and built-ins, and a kitchen ready for your updates. In very good condition with solid construction, the home also includes a 2-car garage. An excellent opportunity to customize in a premier location, just minutes from

    Alicia Gannon Dulin Benson & Mangold, LLC

    9235 Martingham Dr, Saint Michaels, MD 21663
  • 8629 Unionville Rd, Easton, MD 21601
    8629 Unionville Rd, Easton, MD 21601
    8629 Unionville Rd, Easton, MD 21601
    /56

    $639,000

    • 3 Beds
    • 2.5 Baths
    • 2,246 Sq Ft

    8629 Unionville Rd, Easton, MD 21601

    BRAND NEW AND READY FOR IMMEDIATE OCCUPANCY! This spacious 2200+ square foot new build features a MAIN LEVEL OWNER'S SUITE and high end appointments throughout. Step into the main level and enjoy an open concept layout including a spacious family room with gas fireplace, formal office with cathedral ceiling, morning room, dining area and a half bath. The luxury kitchen features a center island

    Adam Ellison Long & Foster Real Estate, Inc.

    8629 Unionville Rd, Easton, MD 21601

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