Exceptional Multi-Family Property with Water Views on City Island

Welcome to 111 Rochelle Street — a rare and elegant multi-family estate located at the coveted southern tip of City Island. This stately 1920s property offers three independent residences, each immersed in the unmistakable charm of coastal living. Surrounded by sweeping water views and the tranquil sounds of sailboats from the nearby Morris Yacht Club, this home is a serene retreat just 20 minutes from Manhattan.

Property Overview:
Total building square footage: 3160 square feet
Lot size: 7000 square feet (100 ft deep by 70 ft wide)

East Residence – “111 Rochelle Street East”

Currently the owner’s primary residence, this beautifully updated 5-bedroom home spans approximately 2107 square feet across three spacious levels. A breezy front porch welcomes you with waterfront views of the Long Island Sound evoking coastal calm, charm and tranquility.
Inside, a circular-flow layout creates an open, airy feel—enhanced by oversized windows, high ceilings, and a large bay window with built-in seating. The expansive kitchen is a chef’s dream, featuring ample counter space, cabinetry, and a full bathroom just off to the side. French doors lead to a beautiful,16'x18' oversized deck, ideal for alfresco dining and entertainment.
The adjacent dining room, centered around a stunning fireplace, is perfect for gatherings and entertaining. Upstairs, the second level includes a generous primary bedroom, two additional bedrooms (one currently used as an office), and a beautifully renovated full bathroom.
The third floor offers a flexible layout: two bedrooms and an open-concept living area ideal for use as a family room, guest suite, fitness center or additional workspace.
The entire residence has been thoughtfully renovated with a modern yet coastal design, maintaining its timeless pre-war character.


West Residence – “111 Rochelle Street West”
A separate, equally charming residence full of classic prewar elegance, this home includes 1053 square feet of space and period details throughout. A curved, hand-carved oak staircase serves as a striking centerpiece, complemented by soaring ceilings and original moldings.
The main level features two spacious entertaining rooms and a kitchen with direct access to the backyard. Upstairs are two comfortable bedrooms and a full bathroom.

The Cottage – Newly Renovated Guest House
Nestled at the rear of the property, this enchanting guest cottage offers its own slice of island living. Features include:
A queen-sized Murphy bed.
Full bathroom
Lofted sleeping/storage area
Compact yet functional kitchenette
Approx. 300 square feet
Ideal for guests, rental income, or a peaceful artist’s studio

111 Rochelle Street also offers a full unfinished basement in great condition, and two driveways fitting 4 cars.

The City Island Lifestyle
City Island is a rare gem — a tight-knit, coastal village within New York City. Home to yacht clubs, private beaches, art galleries, boutique shops, and excellent dining (many with stunning views of the Manhattan skyline, Eastchester Bay, and Long Island Sound), the island offers a lifestyle unlike any other in the city.

Residents enjoy:
A true beach-town atmosphere
Low taxes and high-quality city services
Easy access to Manhattan via car or public transit
Excellent schools, library, post office, and more
Active boating, social, and cultural community events

It’s no wonder City Islanders rarely want to leave.

111 Rochelle Street is one of the few properties on City Island that offers this much space, flexibility, and historical charm — all with postcard-worthy water views. Whether you’re looking for a multi-generational home, an investment property, or simply a peaceful retreat from the city, this is an extraordinary opportunity.

Don’t miss your chance to experience the Ci