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.
Single-familyProperty Type
1999Year Built
0.62 acresLot Size
$416Est. Price/Sq.Ft.
2 car garageParking
Listed by John McGlannan• Meredith Fine Properties
•410-714-9166 (broker)
•mre@goeaston.net (broker)
Bought with Rebecca Biggs• Tilghman Island Realty Inc
Tilghman Island. Do not miss this fabulous home located in the sought after water privileged Tilghman Beach Neighborhood. Sited just steps away from the Community beach and picnic area you will enjoy wide open Chesapeake Bay views. The main house offers two bedrooms and two full bathrooms beautiful hardwood floors throughout. The gourmet kitchen features stainless appliances granite countertops hand made solid wood cabinetry, gas cooktop & built in microwave. Step out to the large waterside deck to enjoy spectacular sunset water views while entertaining or just relaxing at the end of the day with your favorite beverage. Next we have the art studio/ guest house built in 2017. This space is truly one of a kind here you will find a relaxing getaway right in your own backyard, boasting a screened in porch with more water views of the Chesapeake Bay, split unit for heating and cooling and a half bath. Other features of this great offering include large two car garage/ workshop with electric, outside shower, paved driveway, extensive landscaping & gardens with fruit trees. New roof 2018. New HVAC 2016. Make your showing appointment today!
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Beds
—
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
0.62 Acres
Year renovated
—
Sq. Ft.
1,232
Year built
1999
Style
Single Family Residential
County
Talbot County
APN
05 187648
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 26, 2026.
VM
Village Mixed District
The Village Mixed District provides for low- or moderate-intensity residential and commercial uses. This district may contain a mixture of residential, commercial, and maritime/agricultural service uses. The commercial and service uses serve residents of the village and nearby areas, and may include heritage tourism uses to attract visitors. Limited new development is directed to this district so that the environment and natural resources of nearby rural areas are protected and preserved. These districts may have public water and/or sewer service with relatively smaller lots and higher densities than surrounding rural areas.
Permitted uses
Include but are not limited to:
Gas station
Bank
Day care facility
General retail
Restaurant
Housing-Group
Housing-Single unit
Office
Fire house
Police station
Property details
Parking
Parking Information
# of Detached Garage Spaces: 2
Garage Features: Covered Parking, Garage - Front Entry, Garage - Side Entry, Garage Door Opener