93

Homes for Sale near St. Michaels Middle/High School

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  • 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
  • 209 Webb Ln, Saint Michaels, MD 21663
    209 Webb Ln, Saint Michaels, MD 21663
    209 Webb Ln, Saint Michaels, MD 21663
    /33

    $229,000 Open Sat 11AM - 1PM

    • 2 Beds
    • 1 Bath
    • 932 Sq Ft

    209 Webb Ln, Saint Michaels, MD 21663

    Wonderful opportunity to live in the quaint, picturesque and historic town of St Michaels at a great price. New carpeting, and new paint. Move in ready. Well kept, light filled townhouse with 2 bedrooms, one bath and fenced back yard. Must be primary residence. 2 assigned parking spaces. Walkable to all St Michaels has to offer.

    Agent Photo

    Harry Kaiser

    Coldwell Banker Realty

    (844) 491-6381

    209 Webb Ln, Saint Michaels, MD 21663
  • 0 St Michaels Rd Unit MDTA2012442, Newcomb, MD 21653
    0 St Michaels Rd Unit MDTA2012442, Newcomb, MD 21653
    0 St Michaels Rd Unit MDTA2012442, Newcomb, MD 21653
    /27

    $1,795,000

    • Land
    • 20 Acres
    • $89,750 per Acre

    0 St Michaels Rd Unit MDTA2012442, Newcomb, MD 21653

    20 acres off St Michaels Rd overlooking Newcomb Creek and out to the Miles River. Partially cleared shoreline offering expansive views of the water with beautiful sandy beaches and high elevation. During the summer, enjoy a quick boat ride to St. Michaels and all that the town has to offer. In the fall and winter, enjoy great goose and duck hunting. Approved for 6 bedroom SDA.

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 421-7750

    0 St Michaels Rd Unit MDTA2012442, Newcomb, MD 21653
  • 6827 Bellevue Rd, Royal Oak, MD 21662
    6827 Bellevue Rd, Royal Oak, MD 21662
    6827 Bellevue Rd, Royal Oak, MD 21662
    /32

    $350,000

    • 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. Michaels Welcome 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 weekend

    Agent Photo

    Angela Simonelli

    Compass

    (410) 200-0414

    6827 Bellevue Rd, Royal Oak, MD 21662
  • 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
  • 216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    216 E Chew Ave, Saint Michaels, MD 21663
    /132

    $1,795,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 3,575 Sq Ft

    216 E Chew Ave, Saint Michaels, MD 21663

    Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, seasonal farmer's market, museums and more. This home has received a fresh interior painting and

    Agent Photo

    Christopher Clinton

    Coldwell Banker Chesapeake Real Estate Company

    (855) 940-3395

    216 E Chew Ave, Saint Michaels, MD 21663
  • 6135 Summit St, Tilghman, MD 21671
    6135 Summit St, Tilghman, MD 21671
    6135 Summit St, Tilghman, MD 21671
    /31

    $365,000

    • 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
  • 28309 Village Lake Way, Easton, MD 21601
    28309 Village Lake Way, Easton, MD 21601
    28309 Village Lake Way, Easton, MD 21601
    /50

    $810,000

    • 4 Beds
    • 2.5 Baths
    • 2,800 Sq Ft

    28309 Village Lake Way, Easton, MD 21601

    Beautifully maintained 4-bedroom, 2.5 bath home in the highly desirable Easton Village community, offering a perfect blend of traditional style, modern comfort, and timeless charm. Step into a bright 2-story foyer with newly installed luxury vinyl plank (LVP) flooring that continues throughout much of the home. On either side, the formal living and dining rooms provide elegant spaces for

    Agent Photo

    Lori Woods-Fortney

    Berkshire Hathaway HomeServices Homesale Realty

    (410) 517-7606

    28309 Village Lake Way, Easton, MD 21601
  • 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
  • 21384 Coopertown Rd, Tilghman, MD 21671
    21384 Coopertown Rd, Tilghman, MD 21671
    21384 Coopertown Rd, Tilghman, MD 21671
    /25

    $5,200,000

    • 20 Beds
    • 24 Baths
    • 14,035 Sq Ft

    21384 Coopertown Rd, Tilghman, MD 21671

    *A Once-in-a-Lifetime Chesapeake Bay Waterfront Offering – The Iconic Tilghman Island Inn* NOTE: Has public sewer and well. Welcome to a rare opportunity to own one of the most beautiful, fully reimagined waterfront hospitality properties on Maryland’s Eastern Shore. Set on five acres with sweeping views of the Chesapeake Bay, the Tilghman Island Inn is that extraordinary blend of romance,

    Agent Photo

    Angela Simonelli

    Compass

    (410) 200-0414

    21384 Coopertown Rd, Tilghman, MD 21671
  • 26396 St Michaels Rd, Newcomb, MD 21653
    26396 St Michaels Rd, Newcomb, MD 21653
    26396 St Michaels Rd, Newcomb, MD 21653
    /23

    $2,900,000

    • 3 Beds
    • 3 Baths
    • 1,973 Sq Ft

    26396 St Michaels Rd, Newcomb, MD 21653

    Generational Waterfront Farm. Magnificent Building site on the Miles River on 50+ acres. Private tree-lined driveway passing through productive fields, mature evergreen and deciduous trees. There is a brick cape cod on the property and an outbuilding that should be considered a footprint for future development. Existing well, pier and bulkhead area on the cove (Newcomb Creek). Over 1500 of

    Agent Photo

    Brian Gearhart

    Benson & Mangold, LLC

    (410) 618-4530

    26396 St Michaels Rd, Newcomb, MD 21653
  • 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
  • 5744 Johns Way, Tilghman, MD 21671
    5744 Johns Way, Tilghman, MD 21671
    5744 Johns Way, Tilghman, MD 21671
    /41

    $450,000

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

    5744 Johns Way, Tilghman, MD 21671

    2 year old cottage located on Tilghman Island. 3 bedrooms and 2.5 baths, this property is perfect for full time residents or for weekend getaways. Property is located on a quite cul-de-sac and backs up to trees. Large open living room, dining area and kitchen provides enough space for family gatherings or entertaining friends. Kitchen has granite counters and stainless appliances along with a

    Rebecca Biggs

    Tilghman Island Realty Inc

    (667) 245-9539

    5744 Johns Way, Tilghman, MD 21671
  • 6660 Reeses Pride Rd, Sherwood, MD 21665
    6660 Reeses Pride Rd, Sherwood, MD 21665
    6660 Reeses Pride Rd, Sherwood, MD 21665
    /72

    $765,000

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft

    6660 Reeses Pride Rd, Sherwood, MD 21665

    Your Eastern Shore paradise awaits! This awesomely updated, meticulously maintained, classic colonial-style home is like a breath of fresh air. Located on a full 2 acre parcel, in the heart of the sought after Deep Harbour Farm community, custom features include a lovely private backyard oasis, designed around an 18’x32’ inground salt-water pool, and surrounded by all new, high-quality fencing,

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 431-3957

    6660 Reeses Pride Rd, Sherwood, MD 21665
  • 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
  • 408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    408 Spinnaker Ln, Saint Michaels, MD 21663
    /82

    $725,000 Open Sat 11AM - 1PM

    • 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
  • 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
  • 0 Ocean Gateway Unit 20568200, Easton, MD 21601
    0 Ocean Gateway Unit 20568200, Easton, MD 21601
    /2

    $1,795,000

    • Land
    • 1.83 Acres
    • $980,874 per Acre

    0 Ocean Gateway Unit 20568200, Easton, MD 21601

    Two RT 50 parcels located in Easton on sought after O.C. bound side at corner of Rt 50 and Dutchman s Lane. Office on property in good condition but sold as-is. Zoned General Commercial with all utilities available at site.

    Chuck Jr. Benson and Mangold

    0 Ocean Gateway Unit 20568200, Easton, MD 21601
  • 0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671
    0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671
    0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671
    /4

    $3,500,000

    • Land
    • 64.88 Acres
    • $53,946 per Acre

    0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671

    Very rare opportunity to buy a truly beautiful Eastern Shore Farm. This 65 acre farm has four residential building sites. There are two ponds and nearly 4,000’ of rip-rapped shoreline. Build your dream home or compound with unobstructed views of the Chesapeake Bay and Choptank River.

    Chuck Mangold Benson & Mangold, LLC

    0 Bar Neck Rd Unit MDTA2012008, Tilghman, MD 21671
  • 5499 Anderby Hall Rd, Royal Oak, MD 21662
    5499 Anderby Hall Rd, Royal Oak, MD 21662
    5499 Anderby Hall Rd, Royal Oak, MD 21662
    /87

    $6,000,000

    • 3 Beds
    • 4 Baths
    • 5,921 Sq Ft

    5499 Anderby Hall Rd, Royal Oak, MD 21662

    Royal Oak - escape to your own Eastern Shore estate. Anderby Hall is part of an original 1680 land grant. This 12 +/- acre parcel features 3,260' +/- of shoreline (mostly rip rapped) including a tidal pond and island (accessed by bridge)to a private peninsula and private cove. The gated driveway leads to the main house- a 3000 +/- sq.ft. Colonial featuring a great room with fireplace, charming

    Valerie Brown Coldwell Banker Realty

    5499 Anderby Hall Rd, Royal Oak, MD 21662
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /43

    $544,888 New Construction

    • 3 Beds
    • 2 Baths
    • 2,068 Sq Ft

    5648 Trafalgar Cir, Tilghman, MD 21671

    Built in 2025, this new construction home offers the best of Eastern Shore living in the water-privileged community of Tilghman on the Chesapeake. Enjoy the ease of one-level living and a thoughtfully designed split-bedroom floor plan. The welcoming covered front porch opens to a bright entry foyer leading to the spacious, open-concept living area. The kitchen boasts granite countertops, a center

    Kim Crouch Ozman Benson & Mangold, LLC

    5648 Trafalgar Cir, Tilghman, MD 21671
  • 0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601
    0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601
    0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601
    /29

    $8,000,000

    • Land
    • 56.62 Acres
    • $141,293 per Acre

    0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601

    Don’t miss out on this rare opportunity to transform this 56+/ -acre parcel into a premier development project. This expansive property offers a blend of zoning options and fantastic exposure on Route 50, making it an ideal investment for developers. The property is well-suited for high-visibility projects including home improvement stores, pad sites, restaurants, and so much more. All utilities

    Barbara Watkins Benson & Mangold, LLC

    0 Ocean Gateway Unit MDTA2008568, Easton, MD 21601
  • 10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    /109

    $7,900,000

    • 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
  • 24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    24318 Oakwood Park Rd, Saint Michaels, MD 21663
    /44

    $1,195,000

    • 3 Beds
    • 3 Baths
    • 2,085 Sq Ft

    24318 Oakwood Park Rd, Saint Michaels, MD 21663

    Welcome to Old House Cove Waterfront Retreat in St. Michaels, MDNestled on nearly half an acre with scenic frontage along Old House Cove, this quintessential Eastern Shore property offers a rare combination of waterfront serenity, literary history, and timeless design. The expansive parcel provides privacy in a highly desirable location, just minutes from the heart of St. Michael’s—one of

    Kathleen Eder Compass

    24318 Oakwood Park Rd, Saint Michaels, MD 21663
  • Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    Lot 16A Meadow St, Saint Michaels, MD 21163
    /24

    $799,000 New Construction

    • 4 Beds
    • 2.5 Baths

    Lot 16A Meadow St, Saint Michaels, MD 21163

    Welcome to the quaint town of St. Michaels. Waterfront dining, history and small town feel are combined to give you a perfect home for full time or vacation home.Lacrosse homes is proud to present The Pointe.Time to make your personal selections.Make this home your personal staement.Pick the exterior colors, interior feature such as flooring, cabinets, countertops and more.Make this

    George Bailey Keller Williams Flagship

    Lot 16A Meadow St, Saint Michaels, MD 21163
  • 7605 Pendleton Farm Ln, Easton, MD 21601
    7605 Pendleton Farm Ln, Easton, MD 21601
    7605 Pendleton Farm Ln, Easton, MD 21601
    /8

    $1,299,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 2,840 Sq Ft

    7605 Pendleton Farm Ln, Easton, MD 21601

    Experience exceptional waterfront living in this custom-built home set on a private, 3-acre lot. Designed to maximize comfort and connection to the outdoors. The spacious floor plan includes a dedicated office, a cozy den and a gourmet kitchen. The oversized garage and separate laundry room are an added bonus to this perfect property. This custom designed and built - one of a kind home is

    Connie Loveland Benson & Mangold, LLC

    7605 Pendleton Farm Ln, Easton, MD 21601
  • 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
  • 21825 Langdon Farm Rd, Sherwood, MD 21665
    21825 Langdon Farm Rd, Sherwood, MD 21665
    21825 Langdon Farm Rd, Sherwood, MD 21665
    /47

    $2,395,000

    • 3 Beds
    • 3.5 Baths
    • 3,847 Sq Ft

    21825 Langdon Farm Rd, Sherwood, MD 21665

    It doesn't get any better than this ! Stunning brand-new ,one-story coastal residence with a contemporary flair! As soon as you enter this magnificent home, you will be captivated by 20'+ ceilings, superb craftsmanship , an extremely well-designed open floor-plan; breathtaking water-views on Dun Cove and a luxurious yet inviting kitchen. There are a total of 3 en-suite bedrooms as well as an

    Robert Lacaze TTR Sotheby's International Realty

    21825 Langdon Farm Rd, Sherwood, MD 21665
  • 6403 Bozman Neavitt Rd, Neavitt, MD 21652
    6403 Bozman Neavitt Rd, Neavitt, MD 21652
    6403 Bozman Neavitt Rd, Neavitt, MD 21652
    /31

    $469,500

    • 3 Beds
    • 2 Baths
    • 1,834 Sq Ft

    6403 Bozman Neavitt Rd, Neavitt, MD 21652

    Neavitt is a village of +/-seventy houses located at the end of a peninsula surrounded by water. About 12 miles from the shops and restaurants of St Michaels, it is in another, much more peaceful world, with its own park and playground, a public landing with a launch for canoes, and an active community association. Most residents have retired or plan to retire from professional jobs in

    Joan Wetmore TTR Sotheby's International Realty

    6403 Bozman Neavitt Rd, Neavitt, MD 21652
  • 7090 Cooper Point Rd, Bozman, MD 21612
    7090 Cooper Point Rd, Bozman, MD 21612
    7090 Cooper Point Rd, Bozman, MD 21612
    /86

    $7,500,000

    • 5 Beds
    • 6 Baths
    • 10,000 Sq Ft

    7090 Cooper Point Rd, Bozman, MD 21612

    Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design.The custom brick exterior is crowned

    Laura Carney TTR Sotheby's International Realty

    7090 Cooper Point Rd, Bozman, MD 21612
  • 8805 Cummings Rd, Wittman, MD 21676
    8805 Cummings Rd, Wittman, MD 21676
    8805 Cummings Rd, Wittman, MD 21676
    /39

    $385,000

    • 2 Beds
    • 1.5 Baths
    • 1,364 Sq Ft

    8805 Cummings Rd, Wittman, MD 21676

    Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas, 2 office spaces, and generous storage. Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Elevated and

    Wink Cowee Benson & Mangold, LLC

    8805 Cummings Rd, Wittman, MD 21676
  • 912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    912 Calvert Ave, Saint Michaels, MD 21663
    /11

    $229,000

    • Land
    • 0.25 Acre
    • $916,000 per Acre

    912 Calvert Ave, Saint Michaels, MD 21663

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

    Tom Crouch Benson & Mangold, LLC

    912 Calvert Ave, Saint Michaels, MD 21663
  • 7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
    /40

    $2,295,000

    • 6 Beds
    • 3.5 Baths
    • 1,454 Sq Ft

    7049 & 7047 Acorn Aly, Royal Oak, MD 21662

    **Discover Your Waterfront Oasis in Royal Oak** Nestled in the charming town of Royal Oak, these exceptional waterfront properties present breathtaking views of Oak Creek, conveniently located near the Miles River and the renowned Chesapeake Bay. Positioned between the picturesque communities of Saint Michael’s and Easton, this rare gem boasts approximately 541 feet of pristine water frontage,

    Blaine Williamson McClain-Williamson Realty, LLC

    7049 & 7047 Acorn Aly, Royal Oak, MD 21662
  • 21907 Sherwood Landing Rd, Sherwood, MD 21665
    21907 Sherwood Landing Rd, Sherwood, MD 21665
    21907 Sherwood Landing Rd, Sherwood, MD 21665
    /34

    $259,900

    • 3 Beds
    • 1.5 Baths
    • 1,336 Sq Ft

    21907 Sherwood Landing Rd, Sherwood, MD 21665

    First time offered in 60 years! Nestled in the heart of a charming waterfront village, this classic 3-bedroom, 1.5-bath Eastern Shore home exudes timeless appeal. With rich historic character and warm wood floors throughout, it’s ready for your personal touch to bring it back to life. Enjoy partial water views and the convenience of a county pier and kayak launch just down the street, providing

    Wink Cowee Benson & Mangold, LLC

    21907 Sherwood Landing Rd, Sherwood, MD 21665
  • 6369 Neavitt Manor Rd, Neavitt, MD 21652
    6369 Neavitt Manor Rd, Neavitt, MD 21652
    6369 Neavitt Manor Rd, Neavitt, MD 21652
    /11

    $150,000

    • 1 Bed
    • 1 Bath
    • 832 Sq Ft

    6369 Neavitt Manor Rd, Neavitt, MD 21652

    Nice location, in small water front community, 15 min to St Michaels. Corner lot and drive way for parking, would make nice weekend get away or summer home. Check it out

    Bill Griffin Results Realty Inc.

    6369 Neavitt Manor Rd, Neavitt, MD 21652
  • 25826 Orchard Terrace, Royal Oak, MD 21662
    25826 Orchard Terrace, Royal Oak, MD 21662
    25826 Orchard Terrace, Royal Oak, MD 21662
    /20

    $3,495,000 New Construction

    • 4 Beds
    • 4.5 Baths

    25826 Orchard Terrace, Royal Oak, MD 21662

    Buildable 1.6 +/- acre lot ready for your vision and a builder ready to help you make it a reality! Over 500 ft of shoreline on the Tred Avon River. Close to the public park/playground and just a short boat ride or ferry ride to Oxford. Centrally located between Easton and St Michaels. Just minutes to Talbot County's favorite waterfront towns by car, bike, or boat.

    Chuck Mangold Benson & Mangold, LLC

    25826 Orchard Terrace, Royal Oak, MD 21662
  • 5084 Ferry Neck Rd, Royal Oak, MD 21662
    5084 Ferry Neck Rd, Royal Oak, MD 21662
    5084 Ferry Neck Rd, Royal Oak, MD 21662
    /58

    $4,395,000

    • 4 Beds
    • 4 Baths
    • 7,903 Sq Ft

    5084 Ferry Neck Rd, Royal Oak, MD 21662

    Tucked within a canopy of trees along Maryland’s Eastern Shore, this remarkable home rests quietly beside the Choptank River. The setting feels worlds away, eighty acres of meadows and woodland that open gently to more than 1,800 feet of private shoreline, where a western exposure captures breathtaking sunsets reflected across the water. The residence at 5084 Ferry Neck Road was shaped by owners

    Ron Mangas TTR Sothebys International Realty

    5084 Ferry Neck Rd, Royal Oak, MD 21662
  • 9792 Martingham Cir, Saint Michaels, MD 21663
    9792 Martingham Cir, Saint Michaels, MD 21663
    9792 Martingham Cir, Saint Michaels, MD 21663
    /39

    $975,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3 Baths
    • 2,135 Sq Ft

    9792 Martingham Cir, Saint Michaels, MD 21663

    Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels! This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer. Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier

    Keith Hensley Meredith Fine Properties

    9792 Martingham Cir, Saint Michaels, MD 21663
  • 24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    24912 Back Creek Dr, Saint Michaels, MD 21663
    /63

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 3,166 Sq Ft

    24912 Back Creek Dr, Saint Michaels, MD 21663

    Welcome to **Back Creek Landing** — one of Saint Michaels’ most desirable neighborhoods, known for its peaceful setting, friendly community, and easy access to town. Just a few minutes by bike or golf cart from downtown, this neighborhood offers the best of both worlds: close to everything, yet surrounded by nature. This beautifully maintained home invites you in with a wide front porch — perfect

    Kathleen Coale Benson & Mangold, LLC

    24912 Back Creek Dr, Saint Michaels, MD 21663
  • 24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
    /41

    $339,500

    • 2 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    Welcome to Martingham, a premier golf course and waterfront community located just a mile from historic St. Michaels. This Widgeon Place condo offers two en-suite bedrooms and a half bath, with a thoughtful two-level layout designed for comfort and convenience. The main level features a kitchen with a charming breakfast nook, hardwood floors, a gas fireplace, and an open-concept living area. A

    Amy Berry Meredith Fine Properties

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

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