Old Greenwich Real Estate

Welcome to Old Greenwich, a picturesque gem nestled in the heart of Fairfield County, Connecticut. This charming coastal neighborhood, part of the affluent town of Greenwich, is renowned for its stunning waterfront views, serene atmosphere, and a strong sense of community. With its rich history dating back to the 17th century, Old Greenwich beautifully marries classic New England charm with modern conveniences.

As you stroll through the tree-lined streets, you'll discover a delightful mix of historic homes and contemporary residences, each radiating unique character. The neighborhood is home to pristine beaches, including the popular Greenwich Point Park, where residents enjoy sun-soaked days by the Long Island Sound, picnicking, and outdoor activities. The local parks and recreational facilities provide ample opportunity for hiking, biking, and enjoying nature.

Old Greenwich boasts a vibrant local scene with quaint shops, gourmet delis, and charming cafes that invite you to savor the local flavors. The community is also known for its excellent schools, making it an ideal place for families. The area’s close-knit atmosphere is complemented by various community events throughout the year, fostering connections among residents.

For those commuting to New York City, Old Greenwich offers convenient access via Metro-North trains, making it a perfect balance of suburban tranquility and urban accessibility. Whether you’re drawn by the scenic beauty, the welcoming community, or the top-notch amenities, Old Greenwich is a place where you can truly feel at home. Come explore this enchanting neighborhood and discover your dream lifestyle in Old Greenwich!

Newest Listings in Old Greenwich

$2,995,000

24189224 MLS

Exceptional opportunity in the heart of Old Greenwich! A rare opportunity to own a flat, build-ready lot in the heart of Old Greenwich, offering the perfect setting to expand the existing home or create a stunning new custom residence. Set on a level lot in a highly sought-after neighborhood, this spacious 4-bedroom, 2.1-bath Colonial offers over 2,346 square feet of living space with generously sized rooms. The main level features a welcoming foyer, large living room with fireplace, formal dining room, expansive sunroom, and a spacious family room. The eat-in kitchen provides ample workspace and storage, with a conveniently located half bath nearby. Upstairs offers four generously sized bedrooms, two full baths, multiple walk-in closets, and additional closet space throughout. The home's functional layout, oversized rooms, and abundance of living space provide excellent flexibility for everyday living and entertaining.

67 Benjamin St, Greenwich

$2,995,000

4 Beds ⋅ 3 Baths ⋅ 24189215 MLS

67 Benjamin St, Greenwich

$3,995,000

5 Beds ⋅ 7 Baths ⋅ 24188747 MLS

Experience exceptional new construction by Build Casa Tua on Halsey Drive. Spanning four finished levels, this home blends timeless architecture with modern luxury. A dramatic double-height foyer opens to sun-filled living spaces with soaring ceilings, wide-plank white oak floors, and walls of glass leading to a covered deck and private fenced backyard. The custom white oak kitchen features Thermador appliances, quartz countertops, bespoke cabinetry, and a walnut wet bar. Five en-suite bedrooms include a luxurious primary suite with vaulted ceilings, heated bath floors, and a steam shower. Ideally located near Riverside Commons, Metro-North, beaches, downtown Old Greenwich, parks, and top-rated schools.

58 Halsey Dr, Greenwich

$4,000,000

4 Beds ⋅ 3 Baths ⋅ 24179259 MLS

A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one of Old Greenwich's most sought after waterfront settings. The .28 acre property sits within a private association that includes sandy beach access, a boat launch ramp for paddle boarding, kayaking and boating and a large communal waterfront lawn. The current home features a large living room with direct Sound views, a formal dining room, a kitchen and family room opening to a stone patio facing Long Island Sound, and a primary bedroom suite with private bath. Three additional bedrooms and full bath occupy the upper level, sharing the same water views. Gas heating, central air conditioning and an attached 2-car garage are in place. A beautiful and serene location in a private waterfront association, Long Island Sound views and steps to Tod's Point - all within minutes of the Old Greenwich train station, Old Greenwich shops and dining and schools.

14 Shorehame Club Rd, Greenwich

$13,500,000

5 Beds ⋅ 4 Baths ⋅ 24182645 MLS

Live like you're on vacation all year round in Old Greenwich with spectacular 200 feet of waterfront with stunning views of Manhattan. Amazing vistas from every room of this 5 bedroom designer house. Sliding doors open to expansive deck, both covered and uncovered overlooking private pier with ramp to floating dock. Dine al fresco with stunningly beautiful sunsets, and enjoy sailing, boating, swimming and paddle boarding in Greenwich Cove. There is a wide lush lawn for entertaining, playing ball or croquet or hosting a wedding. Enjoy the private, exclusive Lucas Point beach and boatyard, close to Greenwich Point beach. At the end of a cul de sac, this home is a private retreat to enjoy. A short distance to the Old Greenwich village with shops and restaurants and the train station to NYC.

22 Northway, Greenwich

$3,995,000

6 Beds ⋅ 5 Baths ⋅ 24180733 MLS

A rare opportunity to own a classic Shore Colonial in one of Old Greenwich's most sought-after neighborhoods. Set on 0.36 acres and significantly expanded in 2004, this spacious 6 BR 4.5 BA residence offers over 4300 SF of thoughtfully designed living space, blending comfort, functionality, and timeless appeal. A welcoming wraparound porch leads to elegant formal living and dining rooms, a cozy family room, and a bright eat-in kitchen with direct access to a bluestone patio and expansive private backyard, perfect for summer entertaining, outdoor dining, and everyday enjoyment. The second floor features a primary BR with luxurious bath, fireplace, walk-in closet, and private sun deck, along with four more bedrooms and an additional full bath. The third floor offers flexible space for family and guests. The walkout lower level includes a recreation room, exercise area, and another full bath. Ideally located midway between the shops, schools, and train in OG Village and the sandy shores of beautiful Tod's Point Beach. Zoned for Old Greenwich and Eastern Middle Schools.

2 Wahneta Rd, Greenwich

$1,649,600

5 Beds ⋅ 3 Baths ⋅ 24178975 MLS

Welcome to 61 Center Drive, a move-in-ready Old Greenwich home on a dead-end lot. Thoughtfully updated across two levels, this 5-bedroom, 3-full bath home offers approximately 2,300 square feet with bright gathering spaces, renovated finishes, and multiple areas to work, host, relax, or spread out. The main level features hardwood floors, a newly updated kitchen that easily flows into a spacious dining and living room overlooking the foyer with generous natural light. Three bedrooms and two newly renovated full bathrooms complete this level. The finished lower level adds meaningful versatility with a spacious bedroom, renovated full bathroom, fireside recreation room, and an additional flex room that can function as a bedroom, office, gym, or playroom. With its own sense of privacy, this level is well suited for extended-stay guests, multigenerational living, work-from-home needs, or simply extra room to unwind. Outside, a manicured front lawn and garden provide welcoming curb appeal, while the private backyard stone patio offers an inviting setting for summer dinners, weekend grilling, and easy outdoor entertaining. Set in a highly convenient Old Greenwich location, 61 Center Drive is just minutes from Metro-North, Old Greenwich Village, Binney Park, and the town beach, Tod's Point. The home also offers access to sought-after Greenwich public schools, including Eastern Middle School and the International School at Dundee, an authorized International Baccalaureate school.

61 Center Dr, Greenwich

$13,890,000

5 Beds ⋅ 7 Baths ⋅ 24172344 MLS

Exceptional new construction waterfront home set on a private cul-de-sac in one of Old Greenwich's most desirable enclaves. This custom-built residence offers 180-degree unobstructed water views from every bedroom and living space, with beautiful NYC skyline views. Designed for modern coastal living, the home spans three levels with six decks and seamless indoor-outdoor flow. Walls of glass and Nano folding doors open the main level directly to the water, leading to a newly built private dock ideal for boating and entertaining. The interior features 5 bedrooms, 5 full baths, and 2 powder rooms, with wide 10-inch plank floors throughout. The chef's kitchen is centered around a 22-foot quartz island and equipped with Wolf and Sub-Zero appliances, including double ovens, double dishwashers, and additional refrigerated drawers. A third-floor full kitchen offers added flexibility for guests or extended living. Spa-like baths include Lusso Stone fixtures, heated floors, towel warmers, and a Kohler smart toilet in the primary suite. Built to the highest standards with steel beam and pile construction, 16-foot FEMA compliance, and custom Marvin windows. Ideally located just moments from Old Greenwich village, train, and a short walk to schools, town, and beach, with private beach access.

4 Little Cove Ln, Greenwich

$8,750,000

4 Beds ⋅ 4 Baths ⋅ 24157191 MLS

An extraordinary waterfront residence in Old Greenwich, offers a rare opportunity for sophisticated coastal living with spectacular, unobstructed water views from virtually every room. Meticulously redesigned by renowned architect Rick Swann, this exceptional home is defined by dramatic architectural details, soaring ceilings, and an open, light-filled floor plan that seamlessly blends indoor elegance with the serenity of Long Island Sound vistas. First-floor rooms are anchored by expansive walls of glass and French doors that open to a wrap-around deck, the ideal setting for refined entertaining against the backdrop of ever-changing waterfront panoramas. The gourmet kitchen showcases marble countertops, a generous island, and state-of-the-art appliances, reflecting both style and performance. Thoughtfully designed living spaces offer flexibility and grace, with a first-floor den that can serve as a fifth bedroom, private guest suite, or executive office. Each room is elevated by exceptional light and continuous water views, creating an immersive connection to the coastal environment. Set on a premier waterfront parcel with private dock access to Long Island Sound, this distinguished property embodies the ultimate in seaside refinement; a sanctuary of light, luxury, and lifestyle in one of Connecticut's most coveted coastal enclaves.

189 Shore Rd, Greenwich

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