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Tilghman Island Homes for Sale

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

    $560,000 Open Sat 12PM - 3PM

    • 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
  • 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
Maryland Saint Michaels Tilghman Island

Real Estate & Homes for Sale in Tilghman Island, Saint Michaels

Why Live in Tilghman Island

Tilghman Island in Saint Michaels, Maryland, is a 3-mile-long island known for its rich history and evolving community. Once thriving on oyster harvesting, the island has transformed into a luxury real estate destination while maintaining its traditional watermen’s character. The island features a mix of Cape Cod, Colonial Revival, and ranch homes, with waterfront properties being particularly sought after. Local amenities include the Tilghman Island Country Store for groceries and Fairbank Tackle for gas and community news. Dining options range from the chic Wylder hotel and restaurant to casual spots like Two If By Sea. For things to do, residents and visitors can enjoy waterfront recreation at three marinas, a public boat ramp, and private docks, as well as small parks like Back Creek Community Park. The Tilghman Watermen’s Museum offers insights into the island’s maritime heritage. Annual events such as Tilghman Island Day celebrate the community’s waterfront identity with competitions and fresh seafood. The island is fairly self-sufficient but lacks public transportation, so residents rely on cars, bikes, or walking. Tilghman Elementary serves younger students, while older students attend St. Michaels Middle High School, both of which have high ratings. The island is connected to St. Michaels, 15 miles away, via Maryland Route 33, which also provides access to Annapolis and Ocean City. Flood zones identified by FEMA may necessitate flood insurance for some properties.

Learn more about living in Tilghman Island

Frequently Asked Questions

Is Tilghman Island a good place to live?
Tilghman Island is a good place to live. Tilghman Island is considered very car-dependent and somewhat bikeable. Tilghman Island is a neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Tilghman Island has 2 parks for recreational activities. It is sparse in population with 0.5 people per acre and a median age of 61. The average household income is $75,521 which is below the national average. College graduates make up 20.6% of residents. A majority of residents in Tilghman Island are home owners, with 18.4% of residents renting and 81.6% of residents owning their home. A local real estate agent serving Tilghman Island can help you decide if this neighborhood is the right one for you. Learn more on our Tilghman Island neighborhood guide.
Is Tilghman Island, MD a safe neighborhood?
Tilghman Island, MD is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
How much do you need to make to afford a house in Tilghman Island?
The median home price in Tilghman Island is $537,500. If you put a 20% down payment of $107,500 and had a 30-year fixed mortgage with an interest rate of 6.81%, your estimated principal and interest payment would be $2,810 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $120K a year to afford the median home price in Tilghman Island. The average household income in Tilghman Island is $76K.
What are the best public schools in Tilghman Island?
The best public schools that serve Tilghman Island are:
What are the most popular zip codes in Tilghman Island, Saint Michaels, MD?
The most popular zip codes in Tilghman Island, Saint Michaels, MD include 21613, 21403, 21601, 21401 and 21666.
What are the most popular neighborhoods near Tilghman Island, Saint Michaels, MD?
The most popular neighborhoods near Tilghman Island, Saint Michaels, MD are Romancoke, Sunderland, Algonquin, Port Republic and Selby-on-the-Bay.
Are home prices dropping in Tilghman Island?
Yes, home prices in Tilghman Island are down 9% in the last 12 months.

Home Trends in Tilghman Island, MD

On average, homes in Tilghman Island, Saint Michaels sell after 84 days on the market compared to the national average of 50 days. The median sale price for homes in Tilghman Island, Saint Michaels over the last 12 months is $342,500, down 18% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$342,500
Median Single Family Sale Price
$525,000
Median Townhouse Sale Price
$335,000
Average Price Per Sq Ft
$333
Number of Homes for Sale
10
Last 12 months Home Sales
20
Months of Supply
6.00
Median List Price
$537,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-18%
How to Buy a Home How to Finance a Home How to Sell a Home

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