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Homes for Sale near Tilghman Elementary School

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  • 23336 Tunis Ln, Claiborne, MD 21624
    23336 Tunis Ln, Claiborne, MD 21624
    23336 Tunis Ln, Claiborne, MD 21624
    /58

    $549,000

    • 2 Beds
    • 1 Bath
    • 1,190 Sq Ft

    23336 Tunis Ln, Claiborne, MD 21624

    The charming Eastern Shore Waterman’s Cottage, located at 23336 Tunis Lane in Claiborne, MD, was originally built in 1900 and fully renovated in 2017. Additional features include a modern kitchen with stainless steel appliances and a propane stove, as well as a bathroom with Carrera marble, heated floors, and a towel warmer. The home has been rebuilt with durable IPE hardwood, and the crawl space

    Agent Photo

    Maureen McHugh

    Chesapeake Bay Real Estate Plus, LLC

    (667) 771-4585

    23336 Tunis Ln, Claiborne, MD 21624
  • 5820 Tilghman Beach Dr, Tilghman, MD 21671
    5820 Tilghman Beach Dr, Tilghman, MD 21671
    5820 Tilghman Beach Dr, Tilghman, MD 21671
    /31

    $889,000

    • 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, two

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (410) 927-1165

    5820 Tilghman Beach Dr, Tilghman, MD 21671
  • 5934 Tilghman Island Rd, Tilghman, MD 21671
    5934 Tilghman Island Rd, Tilghman, MD 21671
    5934 Tilghman Island Rd, Tilghman, MD 21671
    /41

    $365,000

    • 2 Beds
    • 1.5 Baths
    • 892 Sq Ft

    5934 Tilghman Island Rd, Tilghman, MD 21671

    Simple Pleasures & Smart Living : Tilghman Island Cottage RetreatCharming Eastern Shore Cottage with Endless PossibilitiesDiscover the perfect blend of simplicity and comfort at 5934 Tilghman Island Road, wherethoughtful upgrades meet cozy cottage charm. This delightful 2-bedroom, 1 and one half bathroom homeoffers a smartly designed living space that maximizes every corner for comfortable

    Agent Photo

    John McGlannan

    Meredith Fine Properties

    (667) 222-3534

    5934 Tilghman Island Rd, Tilghman, MD 21671
  • 5379 Anchor Rd, Tilghman, MD 21671
    5379 Anchor Rd, Tilghman, MD 21671
    5379 Anchor Rd, Tilghman, MD 21671
    /56

    $610,000

    • 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 made.Picture yourself unwinding

    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

    $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
  • 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
  • 5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    5520 Leeward Ln, Tilghman, MD 21671
    /83

    $1,750,000

    • 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
  • 9190 Pennywhistle Dr, McDaniel, MD 21647
    9190 Pennywhistle Dr, McDaniel, MD 21647
    9190 Pennywhistle Dr, McDaniel, MD 21647
    /74

    $1,300,000

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

    9190 Pennywhistle Dr, McDaniel, MD 21647

    PARADISE FOUND! 3.5 Acres surrounded on 3 sides by water at the end of a private Cul-de-sac teeming with wildlife and immersed in the scenic beauty of mature trees and wetland grasses.  Enjoy morning coffee and watch the eagles, osprey and turtles nest in your backyard from your kitchen table!  The two-slip pier offers opportunities to fish and crab and serves as a gateway to time on the water

    George Howard George Howard Real Estate Inc.

    9190 Pennywhistle Dr, McDaniel, MD 21647
  • 4957 Bar Neck Rd, Tilghman, MD 21671
    4957 Bar Neck Rd, Tilghman, MD 21671
    4957 Bar Neck Rd, Tilghman, MD 21671
    /45

    $895,000

    • 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
  • 9175 Mallard Point Ct, McDaniel, MD 21647
    9175 Mallard Point Ct, McDaniel, MD 21647
    9175 Mallard Point Ct, McDaniel, MD 21647
    /134

    $1,599,900

    • 4 Beds
    • 3 Baths
    • 2,731 Sq Ft

    9175 Mallard Point Ct, McDaniel, MD 21647

    Step into waterfront luxury with the spectacularly reimagined 4 bedroom, 3 bath custom home on Harris Creek meticulously remodeled by RBCI, Inc., an award-winning custom home builder. No expense was spared in creating this 2,731 sq. ft. masterpiece on over 1.5 acres of magnificent waterfront living. New flooring, counter tops, appliances, garage floor, extended ceiling and walls in master, new

    Ann Holtz Coldwell Banker Realty

    9175 Mallard Point Ct, McDaniel, MD 21647
  • 21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    21486 Mission Rd, Tilghman, MD 21671
    /35

    $699,000

    • 9 Beds
    • 2.5 Baths
    • 5,389 Sq Ft

    21486 Mission Rd, Tilghman, MD 21671

    History:"The Elms" is located on the Northeast corner of Mission Road and Route 33 in the village of Tilghman on Tilghman Island, Talbot County, MD. The house faces west, with the gable oriented on a north/south axis. Built around 1893. The Elms is clad in weatherboard and supported by a brick pier foundation. The roof of this two story frame home is covered in asphalt shingles. The five bay

    Daphne Cawley TTR Sotheby's International Realty

    21486 Mission Rd, Tilghman, MD 21671
  • 8698 Cummings Rd, Wittman, MD 21676
    8698 Cummings Rd, Wittman, MD 21676
    8698 Cummings Rd, Wittman, MD 21676
    /14

    $1,295,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    8698 Cummings Rd, Wittman, MD 21676

    WATERFRONT CHARM! This home was built by Peninsula Construction with care in 2001 for the original and only owners! It boasts an open floor plan with hardwood floors throughout except the carpeted 3 bedrooms. The water views are captivating of Cummings Creek from the the open floor plan of the home but you will also enjoy the waterside screened porch with amazing views of the the quiet

    Leslie Stevenson Shore Living Real Estate

    8698 Cummings Rd, Wittman, MD 21676
  • 7651 Main St, Sherwood, MD 21665
    7651 Main St, Sherwood, MD 21665
    7651 Main St, Sherwood, MD 21665
    /35

    $425,000

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

    7651 Main St, Sherwood, MD 21665

    CHARMING SHERWOOD VILLAGE WITH ITS RICH HISTORY. ONE OF THE BEST KEPT SECRETS.STEP BACK IN TIME, WONDER PAST BEAUTIFUL GARDENS UNDER SHADE TREES, GET GREETED BY THE PEACEFUL SETTING . THE COMMUNITY DOCK WITH MULTIPLE SLIPS AND FLOATING DOCK , THE KAYAK LANDING, IS A NEIGHBORHOOD HANG OUT, VERY POPULAR AT SUNSET TIME TO ENJOY GLORIOUS SUNSETS WITH WIDE OPEN VIEWS OVER HARRIS CREEK.THIS HOME HAS

    Cornelia Heckenbach Long & Foster Real Estate, Inc.

    7651 Main St, Sherwood, MD 21665
  • 9681 Macks Ln, McDaniel, MD 21647
    9681 Macks Ln, McDaniel, MD 21647
    9681 Macks Ln, McDaniel, MD 21647
    /3

    $102,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    9681 Macks Ln, McDaniel, MD 21647

    Please don’t enter the home. The value is in the land.

    Lesley Jackson EXIT Sunshine Realty

    9681 Macks Ln, McDaniel, MD 21647
  • 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
  • 10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    10770 Rich Neck Rd, Claiborne, MD 21624
    /108

    $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
  • 5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    5559 Trafalgar Cir, Tilghman, MD 21671
    /62

    $600,000

    • 5 Beds
    • 3.5 Baths
    • 3,404 Sq Ft

    5559 Trafalgar Cir, Tilghman, MD 21671

    Welcome to this beautiful, spacious 5-bedroom, 3 1/2-bathroom single-family home located in the sought-after Tilghman on Chesapeake community. This property offers the perfect blend of modern comfort and serene island living, featuring an open-concept floor plan with plenty of natural light and elegant finishes. Each bedroom offers ample space and comfort with the Primary Suite offering 2

    Becky Wibberley Coldwell Banker Realty

    5559 Trafalgar Cir, Tilghman, MD 21671
  • 21825 Langdon Farm Rd, Sherwood, MD 21665
    21825 Langdon Farm Rd, Sherwood, MD 21665
    21825 Langdon Farm Rd, Sherwood, MD 21665
    /47

    $2,495,000

    • 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
  • 5582 Trafalgar Cir, Tilghman, MD 21671
    5582 Trafalgar Cir, Tilghman, MD 21671
    5582 Trafalgar Cir, Tilghman, MD 21671
    /58

    $560,000

    • 3 Beds
    • 2.5 Baths
    • 2,110 Sq Ft

    5582 Trafalgar Cir, Tilghman, MD 21671

    The Nottingham, (elevation Z) is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2-car garage with entry through a mudroom that leads to an expansive Great Room area that opens to the Kitchen. The Kitchen is ready for entertaining and cooking comforting meals for family and friends. An open dinette and large kitchen island offer a plethora of space for informal dining. You can take

    Stacie Luhrman Benson & Mangold, LLC

    5582 Trafalgar Cir, Tilghman, MD 21671
  • 21732 Cabin Ln, Sherwood, MD 21665
    21732 Cabin Ln, Sherwood, MD 21665
    21732 Cabin Ln, Sherwood, MD 21665
    /5

    $25,000

    • Land
    • 0.13 Acre
    • $192,308 per Acre

    21732 Cabin Ln, Sherwood, MD 21665

    .2 +/- acres located off of Cabin Ln in Sherwood, Md. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    21732 Cabin Ln, Sherwood, MD 21665
  • 21748 Cabin Ln, Sherwood, MD 21665
    21748 Cabin Ln, Sherwood, MD 21665
    21748 Cabin Ln, Sherwood, MD 21665
    /5

    $25,000

    • Land
    • 0.80 Acre
    • $31,250 per Acre

    21748 Cabin Ln, Sherwood, MD 21665

    .8 +/- acres located off of Punch Point Rd. Approximately 2.5 miles from Tilghman, Md.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    21748 Cabin Ln, Sherwood, MD 21665
  • 7683 Tilghman Island Rd, Sherwood, MD 21665
    7683 Tilghman Island Rd, Sherwood, MD 21665
    7683 Tilghman Island Rd, Sherwood, MD 21665
    /41

    $499,000

    • 3 Beds
    • 1.5 Baths
    • 5,344 Sq Ft

    7683 Tilghman Island Rd, Sherwood, MD 21665

    BACK ON MARKET-by no fault of Seller. Welcome to this beautifully updated 3-bedroom, 1.5-bath home, offering both charm and versatility. The home features three spacious bedrooms, including one with an attached area that can serve as a walk-in closet, nursery, or home office—perfect for adapting to your needs. With 1.5 bathrooms, you'll enjoy the convenience of a full bath and an additional half

    Katie Mister Keller Williams Select Realtors of Cambridge

    7683 Tilghman Island Rd, Sherwood, MD 21665
  • 8898 New Rd, Wittman, MD 21676
    8898 New Rd, Wittman, MD 21676
    8898 New Rd, Wittman, MD 21676
    /26

    $289,000

    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    8898 New Rd, Wittman, MD 21676

    Discover peaceful country living at 8898 New Rd. This thoughtfully refreshed 3‑bed, 2‑bath ranch boasts a modern kitchen, an open floor plan, and natural light throughout. The primary suite offers comfort and privacy, while two extra bedrooms are perfect for family, guests, or a home office. Situated on a nearly half‑acre lot, the private backyard offers a relaxing escape or entertaining space.

    BJ Kilby EXIT On The Bay

    8898 New Rd, Wittman, MD 21676
  • 10376 Claiborne Rd, Claiborne, MD 21624
    10376 Claiborne Rd, Claiborne, MD 21624
    10376 Claiborne Rd, Claiborne, MD 21624
    /57

    $264,900

    • 3 Beds
    • 1 Bath
    • 1,282 Sq Ft

    10376 Claiborne Rd, Claiborne, MD 21624

    Looking for a sweet little cottage in a waterfront town minutes from Saint Michaels? The cottage has a brand-new septic system, just installed new toilet, vanity, stove, and refrigerator, hardwood floors, fireplace, large porch off the back, and short walk to Eastern Bay or Tilghman Creek. This home is ready to be loved by its next owner. This property is being sold "as is." Call today for

    Jana Meredith Meredith Fine Properties

    10376 Claiborne Rd, Claiborne, MD 21624
  • 00 New Rd, McDaniel, MD 21647
    00 New Rd, McDaniel, MD 21647
    00 New Rd, McDaniel, MD 21647
    /9

    $200,000

    • Land
    • 8 Acres
    • $24,907 per Acre

    00 New Rd, McDaniel, MD 21647

    8.037 Acres located just west of St. Michaels, MD. All wooded and has been used primarily for hunting and fire wood. There is one and possibly two approved perc sites though they may need to be updated. Access off of New Road and Walkers Turn road, there may be an opportunity to subdivide but would need to be discussed with County Planning and Zoning. Opportunity to build your home with a lot of

    James Bent Benson & Mangold, LLC

    00 New Rd, McDaniel, MD 21647
  • 5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    5648 Trafalgar Cir, Tilghman, MD 21671
    /25

    $556,990 New Construction

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

    5648 Trafalgar Cir, Tilghman, MD 21671

    THIS HOME IS UNDER CONSTRUCTION!Welcome to Sussex, the epitome of modern rancher living! This single-level floor plan has captured the hearts of many, and it's not hard to see why. With stunning curb appeal and thoughtfully designed features and finishes, the Sussex offers versatility to suit any modern lifestyle. Step into an open-concept floor plan that seamlessly connects the Kitchen,

    Mary Ann Hammel Mary Ann Hammel

    5648 Trafalgar Cir, Tilghman, MD 21671
  • 0 Pot Pie Rd, Wittman, MD 21676
    0 Pot Pie Rd, Wittman, MD 21676
    0 Pot Pie Rd, Wittman, MD 21676
    /3

    $35,000

    • Land
    • 2.86 Acres
    • $12,238 per Acre

    0 Pot Pie Rd, Wittman, MD 21676

    ONLINE AUCTION: Bidding begins 7/16/2025 @ 10:00 AM. Bidding ends 7/18/2025 @ 11:50 AM. List Price is Suggested Opening Bid. Lot of Land located in Wittman, Maryland within Talbot County. Property is in close proximity to the many attractions in St. Michaels, Maryland. Easy Access to Major Traffic Artery Tilghman Island Road. Deposit: $7,500.

    Adam Shpritz Ashland Auction Group LLC

    0 Pot Pie Rd, Wittman, MD 21676
  • 21738 Cabin Ln, Sherwood, MD 21665
    21738 Cabin Ln, Sherwood, MD 21665
    21738 Cabin Ln, Sherwood, MD 21665
    /6

    $39,000

    • Land
    • 0.83 Acre
    • $46,988 per Acre

    21738 Cabin Ln, Sherwood, MD 21665

    .8 +/- private acres located in Sherwood, MD. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    21738 Cabin Ln, Sherwood, MD 21665
  • 21747 Cabin Ln, Sherwood, MD 21665
    21747 Cabin Ln, Sherwood, MD 21665
    21747 Cabin Ln, Sherwood, MD 21665
    /6

    $25,000

    • Land
    • 0.23 Acre
    • $108,696 per Acre

    21747 Cabin Ln, Sherwood, MD 21665

    .2 +/- private acres located in Sherwood, MD. Located 10 minutes from St. Michaels, MD and 5 minutes from Tilghman, MD.BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

    Shawn Moore Meredith Fine Properties

    21747 Cabin Ln, Sherwood, MD 21665
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