Tilghman Island Homes with Pool

Tilghman Island Homes with Pool

Welcome to the serene and picturesque Tilghman Island, a hidden gem nestled in Talbot County, Maryland. This charming waterfront community offers a unique blend of tranquil living and vibrant local culture, making it an ideal destination for those seeking a peaceful retreat or a permanent residence.

Tilghman Island is renowned for its stunning views of the Chesapeake Bay, where the gentle sounds of lapping waves and the sight of sailboats gliding across the horizon create a picturesque backdrop for everyday life. The island is rich in history and boasts a tight-knit community that embraces the beauty of nature and the warmth of its residents.

One of the standout features of homes in Tilghman Island is the availability of properties with pools. Imagine stepping out into your own private oasis on a warm summer day, where you can unwind by the poolside, host family barbecues, or simply enjoy a refreshing dip while soaking in the sun. These homes are designed to capture the essence of coastal living, with spacious layouts and outdoor spaces that encourage relaxation and entertainment.

In addition to the luxurious homes with pools, Tilghman Island offers a variety of recreational activities, from fishing and kayaking to biking along scenic trails. The local dining scene is also a delight, featuring fresh seafood and charming eateries that showcase the island's coastal heritage.

If you’re looking for a place where you can embrace a laid-back lifestyle while surrounded by natural beauty, Tilghman Island is the perfect choice. Explore the available properties today and discover your dream home in this idyllic waterfront community!

Newest Tilghman Island Homes with Pool

$1,250,000
4 Beds 3 Baths
Experience Eastern Shore waterfront living in this charming Chesapeake Bay home, where breathtaking sunset views and a relaxed coastal atmosphere create the perfect setting for everyday living or weekend escapes. Designed to embrace the waterfront lifestyle, the property offers exceptional indoor and outdoor spaces for entertaining family and friends. A brick walkway welcomes you to the inviting front porch and foyer, where hardwood floors flow throughout the home. Recently renovated, the kitchen features white cabinetry, quartz countertops and large windows that fill the space with natural light while overlooking the front yard. The spacious living room is highlighted by a cathedral ceiling and opening to a year-round sunroom surrounded by walls of windows showcasing panoramic views of the Chesapeake Bay. The primary suite features a newly renovated bath with a tile and glass shower. Two guest bedrooms, an office and two additional beautifully renovated full baths occupy the opposite wing of the home, while the second level offers a fourth bedroom with skylights. Outside, you'll find everything needed to enjoy life on the water. The waterside pool with swim deck is complemented by a screened porch, expansive patio, covered seating area and a pool house/bar complete with air conditioning and electric. The private pier provides the perfect spot for fishing, crabbing, or simply taking in the spectacular sunsets, while the rip-rapped shoreline offers lasting shoreline protection. Additional improvements include an attached two-car garage, a storage shed with electric, and a new roof installed in 2025. Situated on high ground outside of the flood zone, this exceptional waterfront property offers direct access to some of the Chesapeake Bay's best fishing, boating, waterfront restaurants and the unforgettable Eastern Shore lifestyle.

5480 Windward Dr, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$2,475,000
7 Beds 6 Baths
"Tranquil Waters" is a rare Chesapeake Bay waterfront retreat on Tilghman Island, comprehensively renovated to the highest standard and designed to capture panoramic water views from nearly every room. This extraordinary residence blends refined coastal architecture with the relaxed elegance of Eastern Shore living. Dramatic walls of glass, soaring ceilings, and open living spaces flood the home with natural light while framing endless Bay views, spectacular sunrises, and unforgettable sunsets. The fully renovated interior includes a redesigned chef's kitchen, spa-inspired baths, new windows and sliding doors, updated trim and fireplace features, and extensive system upgrades throughout. Exceptional waterfront amenities include expansive Trex decking, deep-water dockage, a heated indoor pool and spa pavilion, and seamless indoor-outdoor living designed for entertaining and year-round enjoyment. Major capital improvements include new HVAC systems, roof replacement, hot water heater, air purification system, decking, windows, doors, and more, offering true turnkey peace of mind. Beyond its appeal as a private waterfront retreat, "Tranquil Waters" has enjoyed a Successfull Luxury Vacation Rental history, creating an appealing opportunity for buyers seeking both lifestyle and INVESTMENT POTENTIAL. Equally suited as a luxury primary residence, waterfront getaway, or private retreat, "Tranquil Waters" delivers the ultimate Eastern Shore lifestyle: water, light, privacy, and complete escape.

21642 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

Start Your Search