#12 Money Island

Escape to a place unlike anywhere else! Tucked among the iconic Thimble Islands and surrounded by the sparkling waters of Long Island Sound, this enchanting Money Island cottage, affectionately known as "The Dollhouse," offers a rare opportunity to own your own slice of island paradise. Perched along the island's beautiful granite shoreline, this charming retreat is all about slowing down, unplugging and embracing life on the water. Wake to sweeping Sound views, spend your days swimming, boating and exploring the island, then enjoy unforgettable sunsets and peaceful evenings by the sea. A sunroom overlooking the water provides the perfect spot to relax and take in the incredible surroundings. Inside, the bedroom features two sets of bunk beds, while a large Murphy bed in the living room pulls down to provide additional sleeping space for family and guests. Thoughtfully updated while preserving its quintessential New England coastal charm, the cottage features owned, fully paid-off solar panels with no rental or lease fee, along with a composting toilet for convenient off-grid living. Accessible by boat from Stony Creek, with seasonal ferry service to the Thimble Islands, Money Island feels worlds away while remaining close to the Connecticut shoreline. Whether a summer escape, weekend hideaway or treasured gathering place for generations, "The Dollhouse" is more than a cottage-it's a truly special waterfront lifestyle.