Tokeneke Real Estate

Welcome to Tokeneke, a picturesque gem nestled in Darien, Connecticut, within the scenic Fairfield County. This charming neighborhood offers a unique blend of coastal living and suburban tranquility, making it an ideal place for families, professionals, and retirees alike.

Tokeneke is renowned for its stunning waterfront properties, many of which boast breathtaking views of Long Island Sound. The area is characterized by its tree-lined streets, beautifully manicured lawns, and a strong sense of community. Residents enjoy easy access to a private beach, where summer days can be spent soaking up the sun, swimming, or enjoying leisurely strolls along the shore.

The neighborhood is also home to a variety of parks and recreational facilities, perfect for outdoor enthusiasts. Whether you’re looking to hike scenic trails, play a round of tennis, or simply enjoy a picnic with family, Tokeneke has something for everyone. The local schools are highly rated, making it a sought-after area for families looking to provide their children with an excellent education.

Convenience is key in Tokeneke, with easy access to Darien’s vibrant downtown area, where you’ll find an array of shops, restaurants, and cultural attractions. Commuters will appreciate the proximity to the Darien train station, offering a swift ride into New York City.

In Tokeneke, you’re not just buying a home; you’re investing in a lifestyle filled with charm, community, and coastal beauty. Discover the magic of Tokeneke—where every day feels like a vacation!

Newest Listings in Tokeneke

$3,795,000

4 Beds ⋅ 5 Baths ⋅ 24210059 MLS

Set within Darien's coveted private Tokeneke Association, 5 Cross Road is a quintessential stone Colonial gracefully positioned on a private .70 acre property. Timeless architectural character, exceptional privacy, and inviting living spaces define this distinctive residence in one of the town's most sought-after coastal neighborhoods.The thoughtfully updated kitchen serves as the heart of the home, while an extraordinary family room with soaring ceilings and abundant natural light offers a dramatic yet welcoming setting for everyday living and entertaining. A desirable first-floor primary suite provides comfort and convenience, creating an ideal layout for modern living. Classic details and generous rooms throughout complement the home's enduring stone facade and beautifully secluded grounds. Enjoy the rare combination of a tranquil residential setting, private association lifestyle, and convenient access to Darien's village, schools, train, beaches, and waterfront. A special Tokeneke offering where classic New England charm meets effortless, refined living.

5 Cross Rd, Darien

$7,950,000

9 Beds ⋅ 10 Baths ⋅ 24168537 MLS

Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the home's historic integrity while introducing refined, livable spaces. Interiors by acclaimed designer Katie Ridder bring a fresh yet classic sensibility, blending color, texture, and bespoke detail throughout. The main residence offers 7 bedrooms and 6 full baths, anchored by five fireplaces that add warmth and character across its gracious living spaces. A classic carriage house offers a fully equipped 2-bedroom, 1-bath guest residence with its own kitchen, providing exceptional flexibility-ideal for extended stays, in-law living, or a private home office retreat. The grounds, designed by renowned landscape architect Janice Parker, are a true highlight-lush, structured, and beautifully layered for year-round interest. An in-ground saltwater pool completes the estate-like setting, creating a private retreat perfect for both entertaining and quiet enjoyment. Rich in history and elevated by a world-class design team, 16 East Trail offers a rare opportunity to own a piece of Darien's architectural legacy-seamlessly tailored for modern living.

16 E Trail, Darien

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