Tokeneke Real Estate

Welcome to Tokeneke, a picturesque neighborhood nestled in the charming town of Darien, Connecticut. Known for its serene ambiance and stunning waterfront views, Tokeneke is a hidden gem that perfectly blends suburban tranquility with a vibrant community spirit.

As you wander through the tree-lined streets, you’ll discover a mix of elegant homes, many of which boast breathtaking vistas of Long Island Sound. The architectural styles here range from classic New England colonials to modern coastal retreats, catering to a variety of tastes and lifestyles. Tokeneke is not just a feast for the eyes; it’s a community where neighbors become friends, and families thrive.

One of the neighborhood's most appealing features is its proximity to Tokeneke Beach, a private haven for residents that offers sandy shores and a relaxed atmosphere. Whether you enjoy swimming, sunbathing, or simply taking in the stunning sunsets, this beach is the perfect spot to unwind. For those who appreciate outdoor activities, the nearby Tokeneke School and parks provide ample opportunities for recreation, from sports to leisurely strolls.

Additionally, Tokeneke is conveniently located near the heart of Darien, where you’ll find an array of boutique shops, delightful dining options, and vibrant cultural events. With easy access to major highways and the Metro-North train station, commuting to New York City is a breeze, making it an ideal choice for professionals seeking a peaceful home life without sacrificing connectivity.

Discover the charm of Tokeneke, where community, beauty, and convenience come together to create an idyllic living experience.

Newest Listings in Tokeneke

$4,450,000

5 Beds ⋅ 5 Baths ⋅ 24190513 MLS

Welcome to this classic Coastal Connecticut colonial, ideally situated in the coveted Tokeneke Association - offering space, comfort, and versatility for every member of the family. With 5 bedrooms - including a convenient first-floor guest suite and four bedrooms on the second level - this home is designed for gracious everyday living. The main floor features a formal living room, elegant dining room, casual dining area, and a spacious office, all flowing effortlessly together. The chef's kitchen opens to both casual dining and a warm, fireplace-lit gathering room, the heart of the home. A large mudroom with garage and back-entrance access, plus a separate laundry room, adds everyday ease. Retreat to the private primary suite, complete with an en-suite bath and two walk-in closets. The second floor also offers a second en-suite bedroom, two additional bedrooms sharing a beautifully renovated hall bath, a versatile sitting/work area, and abundant storage throughout. The finished basement boasts a spectacular wine room, that holds 1600 bottles, and casual sitting area - perfect for relaxing or entertaining. The attached garage holds two-cars plus, and a third bay is in the "barn" - a blank canvas ready to become a guest quarters, entertaining space, second-floor hangout, studio, or whatever you can imagination. Outside, unwind on the beautiful stone patio, set against an expansive, green yard. A rare opportunity in one of the most sought-after associations.

6 Searles Rd, Darien

$5,895,000

5 Beds ⋅ 5 Baths ⋅ 24171365 MLS

Quietly iconic. Effortlessly cool. Live large without living complicated. This is the rare waterfront home that offers the lifestyle of a grand estate with the ease of a true lock-and-leave retreat. Set on just over an acre in the private Tokeneke Association it's designed for living well not maintaining endlessly. There are four private bedrooms in the main house and several places to lounge. Escape whenever you choose a weekend, a week, or all the days in between. Paddle over to Rowayton for lunch, entertain under the stars by the fire, or spend an afternoon with a great book by the pool. A private guest cottage with multiple sleep configurations offers family and friends their own retreat while preserving yours. Waterfront homes that live this effortlessly are incredibly rare. A manageable home, beautiful grounds, a dock, freeform pool, an abundant vegetable garden and even a chicken coop, all within the security of Tokeneke including optional home check-ins while you're away. Make coming and going completely carefree, an easy house, an extraordinary life.

13 Edgehill Dr, Darien

$8,495,000

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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