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575 MADISON AVENUE, NEW YORK, NY 10022. 212.891.7000 © 2025 DOUGLAS ELLIMAN REAL ESTATE. EQUAL EMPLOYMENT OPPORTUNITY PROVIDER. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES, OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS, AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT, OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY.LISTING DATA REFRESHED ON OCT 20 2025 AT 2:51 PM.

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5379 ANCHOR Rd

tilghman island, MD 21671

$560,000

  • 2 BR
    2 BA, 1 HALF BA
    APPROX. 1,232 SF

INTERESTED? LET'S CONNECT

Bay Breezes & Beautiful Views: Your Tilghman Island Haven

Waterview Living with Room to Breathe on Maryland's Eastern Shore

Step into the good life at 5379 Anchor Road, where Chesapeake Bay magic meets everyday
comfort. This charming home in Tilghman's friendly beach neighborhood sits just a
short stroll from the community beach where neighbors gather and memories are made.
Picture yourself unwinding on the deck with morning coffee, watching the sun sparkle across the
bay waters. Inside, the welcoming home greets you with warm hardwood floors throughout, two
comfortable bedrooms, and two full baths. The kitchen is a joy to cook in—featuring granite
countertops, stainless appliances, and beautiful hand-crafted wood cabinets perfect for whipping up
fresh seafood dinners or casual breakfasts before heading out to explore the water.
What makes this place truly special is the adorable guest cottage built in 2017. This sweet retreat
offers a screened porch with more water views, its own heating and cooling, and a half
bath—perfect for visiting friends or your own creative escape when you need a moment to
yourself.
For water lovers, you're in paradise—grab your kayak or paddleboard and launch right from your
backyard. Gardening opportunities abound-whether ornamental or the fun of your own fresh
summer veggies-the property also includes fruit trees -pies and jams in your future?
The practical perks are all here too: a roomy two-car garage with workshop space for projects,
outdoor shower for rinsing off sandy feet, beautiful landscaping, plus recent updates including a
new roof (2018) and HVAC system (2016) so you can relax knowing the essentials are taken care of.
Beyond your doorstep, discover the authentic charm of Tilghman Island. A short, scenic drive
connects you to the fabulous restaurants, shops and galleries of St. Michaels, Easton, and Oxford.
When you choose this Tilghman Island home, you're investing in more than just real estate—you're
gaining a lifestyle where stress melts away with each bay breeze and sunset. Whether you're looking
for a full-time home with vacation vibes, a weekend getaway from the city grind, or the perfect spot
to eventually retire and watch the osprey soar, this special place offers what so many of us are
searching for—a chance to slow down, breathe deeply, and connect with the beauty of the bay.
Come see what life on Tilghman time feels like. Your Eastern Shore story is waiting to begin.

Details

1,232 Sq Ft

0.62 Private Acres Lot Size

Other

$170 Annually Maintenance/CC

$2,425 Annual Tax

Built in 1999

MLS/Listing ID MDTA2010666

Amenities & Features

Construction - Masonry

Construction - Spray Foam Insulation

Construction - Vinyl Siding

Cooling - Central Air

Cooling - Attic Fans

Ceramic Tile

Hardwood

Block

Heating - Electric

Attic

Pantry

Walk-in Closets

Lot - Level

Lot - Private

Dishwasher

Range Hood

Washer

Construction - Block

Parking - Private

Screened

BRIGHT

Source of Data: BRIGHT MLS

estimate my mortgage

TOTAL MONTHLY COST

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  • PRINCIPAL & INTEREST

    -

  • PROPERTY TAXES

    -

  • COMMON CHARGES

    -

HOME PRICE
DOWN PAYMENT
term
INTEREST

Interested in 5379 ANCHOR Rd?

The data relating to the real estate for sale on this web site comes in part from the Internet Data Exchange Program of the BrightMLS. Real estate listings held by brokerage firms other than Douglas Elliman of VA are marked with the Internet Data Exchange logo and information about them includes the name of the listing brokers. Some properties listed with the participating brokers do not appear on this website at the request of the seller. Listings of brokers that do not participate in Internet Data Exchange do not appear on this website.

All information deemed reliable but not guaranteed. Last date updated: 10/20/2025.
Source: Bright Multiple Listing Service, Inc.

© 2025 Bright Multiple Listing Service, Inc. All rights reserved.