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Tilghman Island Homes for Sale

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

    $550,000

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

    5877 Tilghman Island Rd, Tilghman, MD 21671

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

    Agent Photo

    Angela Simonelli

    Compass

    (410) 200-0414

    5877 Tilghman Island Rd, Tilghman, MD 21671
  • 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
  • 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
  • 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
  • 4912 Bar Neck Rd, Tilghman, MD 21671
    4912 Bar Neck Rd, Tilghman, MD 21671
    4912 Bar Neck Rd, Tilghman, MD 21671
    /83

    $895,000

    • 3 Beds
    • 1 Bath
    • 1,550 Sq Ft

    4912 Bar Neck Rd, Tilghman, MD 21671

    Great value - this home is in move in condition. You can start enjoying your slice of Paradise immediately. Price has been reduced on this awesome waterfront with one of the best sunset views in Tilghman. Property is in and estate and Owners are sadly ready to let this sweet property go. Welcome home to your own little bit of paradise. Three bedrooms, eat in kitchen, dining room or den,

    Connie Loveland Benson & Mangold, LLC

    4912 Bar Neck Rd, 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
  • 5793 Tilghman Island Rd, Tilghman, MD 21671
    5793 Tilghman Island Rd, Tilghman, MD 21671
    5793 Tilghman Island Rd, Tilghman, MD 21671
    /11

    $289,000

    • 3 Beds
    • 1 Bath
    • 810 Sq Ft

    5793 Tilghman Island Rd, Tilghman, MD 21671

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

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    5793 Tilghman Island Rd, Tilghman, MD 21671
  • 5582 Trafalgar Cir, Tilghman, MD 21671
    5582 Trafalgar Cir, Tilghman, MD 21671
    5582 Trafalgar Cir, Tilghman, MD 21671
    /58

    $569,000

    • 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
  • 5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    5654 Trafalgar Cir, Tilghman, MD 21671
    /14

    $509,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    5654 Trafalgar Cir, Tilghman, MD 21671

    The New Castle is a modern ranch-style home with 3 bedrooms, 2.5 baths, and a 2 car garage with drop zone entry, attached to a laundry room, that leads through to the Kitchen. The Kitchen has a large amount of space, plenty of cabinets, and a pantry, making storage and organization plentiful and manageable. The well-equipped kitchen is ready for entertaining and with family and friends. The open

    Mary Ann Hammel Mary Ann Hammel

    5654 Trafalgar Cir, Tilghman, MD 21671
  • 21271 Phillips Rd, Tilghman, MD 21671
    21271 Phillips Rd, Tilghman, MD 21671
    21271 Phillips Rd, Tilghman, MD 21671
    /57

    $430,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 1.5 Baths
    • 1,445 Sq Ft

    21271 Phillips Rd, Tilghman, MD 21671

    Welcome to your Eastern Shore escape! Nestled in the heart of Tilghman Island, this beautifully maintained 3-bedroom, 1.5-bath home blends coastal charm with modern updates. Enjoy breathtaking bay views from the large front bay window, offering a daily dose of waterfront serenity. The home features luxury vinyl plank (LVP) flooring throughout, a completely updated main bathroom, and a spacious

    Adam Chubbuck Douglas Realty, LLC

    21271 Phillips Rd, Tilghman, MD 21671
Maryland Saint Michaels Tilghman Island

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

About 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 $509,990. If you put a 20% down payment of $102,000 and had a 30-year fixed mortgage with an interest rate of 6.76%, your estimated principal and interest payment would be $2,650 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $114K 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, 21601, 21401, 21403 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 23% in the last 12 months.

Home Trends in Tilghman Island, MD

On average, homes in Tilghman Island, Saint Michaels sell after 74 days on the market compared to the national average of 48 days. The average sale price for homes in Tilghman Island, Saint Michaels over the last 12 months is $431,160, down 23% from the average home sale price over the previous 12 months.

Home Trends

Median Price (12 Mo)
$349,500
Median Single Family Price
$505,000
Average Price Per Sq Ft
$315
Number of Homes for Sale
11
Last 12 months Home Sales
18
Months of Supply
7.30
Median List Price
$509,990
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
-24%
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