"The Thimbles today are mostly private seasonal residences, including Davis Island that was once the “Summer White House” of William Howard Taft."
Stony Creek is the gateway to the historic Thimble Islands. The largest grouping of islands in Connecticut, the Thimbles started as a resort community in the mid-19th century with numerous summer hotels and boarding houses. Numbering some hundred islands, about thirty of which are inhabited, the Thimbles today are mostly private seasonal residences, including Davis Island that was once the “Summer White House” of William Howard Taft. Money Island, includes 32 residences, while the largest, Horse Island, is owned by Yale University and maintained as an ecological laboratory. Outer Island is open to the public and is part of the Stewart B. McKinney National Wildlife Refuge. The best way to get a glimpse of these treasures close up is to take a 45-minute cruise offered by tour boats from the Stony Creek Town dock. On the Sea Mist offered by Thimble Island Cruise or Captain Dave’s smaller boat, stories are told of Captain Kidd and his buried treasure along with other local legends.
Top off a day enjoying the water and sun at dining options ranging from the highly-acclaimed French bistro, Le Petit Café, or G-Zen, recognized as one of the top ten vegan restaurants in America. Drop by at my favorite, Lenny’s Indian Head Inn, for steamers and fried clams. Go to the Lobster Shack for one of the best hot lobster rolls on the shoreline with picnic tables on the Branford River, and don’t forget to BYOB. A vintage renovated gas station has been converted to a hugely popular indoor-outdoor barbecue/market at The Stand. The Stony Creek Brewery directly on the Branford River waterfront is a mecca for craft beer aficionados as well as those seeking a casual scenic spot to congregate with friends. Duvig Brewing Company and Thimble Island Brewing Company offer tastings of their craft beer offerings, making Branford a craft beer destination.
A short drive or train ride away on Shoreline East, New Haven broadens the restaurant offerings and provides a wide array of cultural options—Long Wharf, Yale Repertory, and Shubert Theaters, the New Haven Symphony, the Yale Museum of British Art, the Yale Art Gallery, the Peabody Museum of Natural History, and the International Festival of Arts and Ideas in June.
Take a step further and explore the historic eastern end of the Connecticut shoreline with shipbuilding lore in Mystic, the quaint beauty of Essex and the harbor and submarine history in New London and Groton.
With stunning shoreline scenery and extensive options for outdoor recreation, culture, and epicurean delights, Branford has it all. Come and explore!
Featured Listings
310 Litchfield Road, Norfolk, CT
$6,650,000
Known as "The Bungalow", this spectacular Tudor-inspired estate set on 43.8 private acres is one of architect Alfredo S.G. Taylor's finest designs. Built in 1908 for a Remington Arms heiress, the home seamlessly blends Gilded Age grandeur with exceptional modern luxury. The dramatic great hall features soaring 40-foot timber ceilings, a monumental stone fireplace, and exquisite fieldstone and half-timber construction. Thoughtfully updated throughout, the home offers a stunning new eat-in chef's kitchen complete with a butler's pantry and premium appliances, including a True glass-door refrigerator, Miele dishwasher, Wolf warming drawers, Sub-Zero wine and beverage refrigerator, and an exceptional custom range with handcrafted hood. The luxurious marble-clad bathrooms have been beautifully renovated with Kohler fixtures, while custom cabinetry, updated electrical systems, and meticulous craftsmanship elevate every space. Spectacular balconies and a wraparound veranda extend from the main living areas, providing breathtaking views across the surrounding landscape. Offering 6 bedrooms, 6 bathrooms, and 6,766 square feet of living space, the estate is set amid lightly wooded grounds with expansive northern vistas. Additional amenities include a guest house, barn, formal gardens, and a picturesque pond. Approached by a winding, newly improved drive, the residence sits atop a private ridge and culminates in a gracious porte-cochere, creating a sense of arrival rarely found. Recent improvements include a new roof, copper gutters, and two whole-house generators-one serving the main residence and the other dedicated to the guest house. Offering an exceptional combination of privacy, history, and modern luxury, this remarkable estate feels worlds away while remaining just minutes from the heart of Norfolk, with its renowned restaurants, shops, cultural attractions, and year-round events. Conveniently located approximately 120 minutes from Manhattan, it presents a rare opportunity to own one of New England's most distinguished country estates.
175 Brookside Road, Darien, CT
$8,750,000
Exceptional new construction estate by K&C Builders Inc., set on over 2.5 private acres on coveted Brookside Road. Offering approximately 11,000 SF across four finished levels, this stunning residence features 6 bedrooms, 8 full baths, and 1 half bath. Designed for elegant entertaining and everyday living, the home showcases a spectacular great room, gourmet chef's kitchen, private study, cabana-style room opening to the pool area, finished lower level, and finished attic. Premium Rhea European Windows flood the home with natural light while providing exceptional energy efficiency and modern sophistication. Extensive custom millwork, architectural ceiling details, designer lighting, detailed interior paneling, custom cabinetry, and bespoke finishes reflect the superior craftsmanship and attention to detail that define every K&C Builders project. The luxurious primary suite offers a spa-inspired bath and oversized custom walk-in closets. Outdoor amenities include professionally landscaped grounds, a resort-style pool, outdoor kitchen, and expansive entertaining spaces designed for seamless indoor-outdoor living. Ideally located minutes from downtown Darien, Metro-North, beaches, country clubs, and Darien schools, this extraordinary residence presents a rare opportunity to own a signature home built to the highest standards of quality, design, and craftsmanship.
379 Ocean Drive West, Stamford (Shippan), CT
$14,500,000
Completed in 2023 and designed by Michael Smith Architects, this extraordinary six bedroom waterfront residence offers more than 8,700 square feet of luxury living along one of Stamford's most coveted stretches of Ocean Drive West. Built two feet above FEMA flood elevation requirements and featuring sweeping views of Long Island Sound from every principal room, the home combines timeless coastal architecture, exceptional craftsmanship, and modern construction. Thoughtfully designed for both grand entertaining and everyday living, the residence balances expansive gathering spaces with private retreats, all oriented toward the water. A cedar shake exterior, stone detailing, and sunrise to sunset exposure define the home's striking waterfront presence. Across three levels, terraces, balconies, and principal living spaces are carefully positioned to capture panoramic views of Long Island Sound, creating a seamless connection between the interior and the surrounding landscape. The result is a residence equally suited for weekend escapes, year round living, and large scale entertaining. The main level is centered around a dramatic great room that opens directly to the waterfront patio and pool terrace. A separate living room with fireplace and wet bar provides a more intimate setting for gathering, while the custom chef's kitchen and butler's pantry feature extensive cabinetry and storage. A glass enclosed 72 bottle wine display serves as a striking focal point within the dining area. Outdoor amenities rival those of a private resort and include an infinity edge pool with integrated spa, outdoor kitchen, multiple fireplaces, heated covered seating areas, and expansive patios overlooking the Sound. Designed for seamless indoor outdoor living, the property is equally suited for summer entertaining and quiet evenings along the shoreline. Occupying its own private wing, the primary suite enjoys sweeping water views, direct terrace access, a sitting room, dressing area, and a luxurious bath appointed with heated Dolomite marble floors. Five additional ensuite bedrooms occupy the upper levels, complemented by lounge spaces, a fitness room, office, and bonus room. A heated three car garage completes the home. Rarely does a waterfront property combine this level of design, construction quality, and setting in one of Shippan Point's most desirable locations. Visit www.coastalmasterpiece.co for more pictures and information. One of the owners is a licensed real estate agent.
