Old Greenwich Real Estate

Welcome to Old Greenwich, a picturesque coastal gem nestled in the heart of Greenwich, Connecticut. Known for its charming New England character, this vibrant neighborhood offers a delightful blend of serene residential streets, stunning waterfront views, and an inviting community spirit.

Old Greenwich is renowned for its rich history, with many homes dating back to the 19th century, showcasing classic architectural styles that exude timeless elegance. Tree-lined streets and well-manicured gardens create a peaceful atmosphere, making it a perfect place for families and individuals seeking a tranquil lifestyle. The neighborhood is also home to a variety of amenities, including boutique shops, cozy cafes, and gourmet restaurants that cater to diverse tastes.

For outdoor enthusiasts, Old Greenwich boasts easy access to beautiful beaches and parks. The scenic Tod's Point offers expansive green spaces, walking trails, and sandy shores where residents can enjoy picnics, swimming, and breathtaking sunsets over Long Island Sound. The nearby Greenwich Point Park provides additional recreational opportunities, with its serene walking paths and stunning vistas.

Education is a top priority in Old Greenwich, with highly rated schools that foster a nurturing learning environment for children. The community is also well-connected, with convenient access to public transportation, making commuting to New York City a breeze.

Whether you’re looking for a family-friendly neighborhood, a vibrant community, or a serene escape by the sea, Old Greenwich is a delightful place to call home. Experience the charm, beauty, and warmth of this exceptional coastal community, where every day feels like a vacation.

Newest Listings in Old Greenwich

$4,674,000

5 Beds ⋅ 7 Baths ⋅ 24206524 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

$19,995,000

5 Beds ⋅ 7 Baths ⋅ 24164225 MLS

You don't look at your home...you look out from it. Set directly on the waterfront in Old Greenwich, this newly constructed residence is a masterclass in design, engineering and execution where every material, finish and feature was selected without compromise. Beyond a long, privately gated drive, sweeping cove views unfold, leading to a facade clad in premium Thermory wood siding beneath a Spanish slate roof an exterior that feels both grounded and enduring.. Walls of Aluprof glass dissolve the boundary between interior and Long Island Sound, drawing light deep into nearly every principal room. The result is a seamless connection to the water, with unobstructed views that are impossible to replicate. Inside, large-scale radiant-heated Porcelanosa tiles grace the main and lower levels, setting a warm, modern foundation. At the heart of the home, a statement kitchen delivers both performance and presence; featuring custom Vimora cabinetry, top-of-the-line Gaggenau appliances and a fully equipped secondary prep kitchen designed for effortless entertaining at scale. Upstairs, European white oak introduce warmth, while radiant heat continues throughout all main spaces and baths reinforcing a consistent commitment to comfort and precision. The primary suite is conceived as a private retreat, oriented entirely toward the water. A fireplace anchors the space, while a private deck leads directly to the heated pool below. The bath offers a spa-like experience, featuring a sculptural

58 Shore Rd, Greenwich

$3,450,000

5 Beds ⋅ 5 Baths ⋅ 24202309 MLS

Beautifully renovated by the current owners, this 5 bedroom, 5 bath home features refinished hardwood floors throughout, a modern open floor plan with eat-in kitchen/dining that opens to a generous new deck overlooking the level yard, and a versatile main-floor bedroom with a full bathroom that adds flexibility for guests, family, or working from home. The 2nd floor offers 3 well-proportioned bedrooms (one en-suite) and a hall bathroom, a few steps up, a primary bedroom/primary bath, luxurious walk-in-closet, and ample storage. The walk-out Lower Level is fully finished with a playroom, rec room, full bath and den/gym, separate laundry room and lots of storage. Located in a quiet Old Greenwich neighborhood no car needed to get to Binney Park, Perrot Library, Metro North and OG Town.

18 Shady Brook Ln, Greenwich

$1,549,000

5 Beds ⋅ 3 Baths ⋅ 24200241 MLS

Welcome to 61 Center Drive, a move-in-ready Old Greenwich home at the end of a cul de sac. 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, or just relax. 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.

61 Center Dr, Greenwich

$4,000,000

4 Beds ⋅ 3 Baths ⋅ 24205297 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 Shoreham Club Rd, Greenwich

$3,495,000

4 Beds ⋅ 3 Baths ⋅ 24203497 MLS

Rich with classic character this 1918 Colonial sits on one of the most coveted streets in Old Greenwich. With an expansive 3,670 square feet, this charm filled home pairs timeless architectural details. A quintessential wide wraparound front porch greets you, opening into a spacious entry hall that connects the formal living room with high ceilings and into the warm flexible layout., coffered ceiling in the dining room and inviting family room with elevated half cathedral ceiling and skylights. At the center of the home, the family kitchen offers informal dining, a built in family office space and casual seating area, all flowing effortlessly onto an expansive back deck and stone patio. The Perfect private space for indoor-outdoor entertaining and to escape the day. The second floor hosts four light-filled bedrooms and a full bath, while the third level provides a private fifth bedroom suite with its own bath. Set on a .3 acre lot backing up to the scenic grounds of Innis Arden Golf Club, the property offers exceptional privacy. Unbeatable coastal lifestyle offering. Work in NYC? it's a 7 minute walk to the Old Greenwich Train Station or 2 minute drive. Effortless stroll to the village, local favorite King's Market, Binney Park and the seasonal outdoor concert series, living at 14 Highview, including short 9 minute bike ride to Tod's Point beach. Location is everything, start your next chapter of your story here in the heart of Old Greenwich at 14 Highview Avenue!

14 Highview Ave, Greenwich

$2,500,000

3 Beds ⋅ 4 Baths ⋅ 24198810 MLS ⋅ Harbor House Association BLDG.

Moments from the beach in one of Old Greenwich's most distinctive concierge residences. Sun-filled and sophisticated, this beautifully appointed three-bedroom blends timeless Shore Colonial character with effortless, turnkey living. An open floor plan is enhanced by handcrafted millwork, hardwood floors and signature custom windows, while the bright kitchen flows seamlessly into the living room with fireplace and French doors overlooking the peaceful grounds. Exceptional amenities elevate the lifestyle, including a door person, water-view rooftop terrace, entertaining and wine-tasting room with stone fireplace, personal wine locker, catering kitchen, fitness room, outdoor grills and dining terrace, plus two assigned parking spaces. Just seconds from Tod's Point beaches and nature preserve and close to the shops, restaurants and train in Old Greenwich Village, this is a rare opportunity to enjoy sophisticated, low-maintenance coastal living, equally ideal as a full-time or part-time residence.

165 Shore Rd Unit D, Greenwich

$9,875,000

5 Beds ⋅ 6 Baths ⋅ 24196984 MLS

Hamptons-Inspired Elegance in Waterfront Lucas Point Experience the ease of coastal living just one hour from New York City in the coveted private waterfront association of Lucas Point in Old Greenwich. Residents enjoy an exceptional lifestyle anchored by a private sandy beach, dock, and boat storage, while the neighborhood's charming privet-lined lanes foster a true sense of community--where neighbors gather on their porches to share conversation and watch the evening sunset. A ''Coastal Shingle Style Residence'', 2016 HOBI Award winning home, designed by noted Greenwich Architect Steven Mueller, sits atop one of the highest elevations in Lucas Point, on one of the neighborhood's largest properties. The level half-acre parcel lies outside the flood zone and offers dual access from Shore

203 Shore Rd, Greenwich

$3,300,000

24196451 MLS

A once-in-a-generation waterfront opportunity in Old Greenwich, perched above Greenwich Cove with breathtaking sunsets, expansive water views, and direct access to "The Cove" and Long Island Sound, 1 Hendrie Drive Ext offers the opportunity to build or renovate in an exceptional waterfront setting. The property includes a separate tax parcel with a private dock, creating the unique advantage of owning both the residence parcel and a separately deeded dock parcel-a rare offering in Old Greenwich. .Just minutes from the village, train station, schools, and library, this property combines waterfront serenity with exceptional everyday convenience. Sold As-Is. Mailbox address: 1 Cove Ridge Lane, Old Greenwich, CT.

1 Hendrie Dr Extension, Greenwich

$3,300,000

5 Beds ⋅ 3 Baths ⋅ 24194050 MLS

A once-in-a-generation waterfront opportunity in Old Greenwich, perched above Greenwich Cove with breathtaking sunsets, expansive water views, and direct access to "The Cove" and Long Island Sound, 1 Hendrie Drive Ext offers the opportunity to build or renovate in an exceptional waterfront setting. The property includes a separate tax parcel with a private dock, creating the unique advantage of owning both the residence parcel and a separately deeded dock parcel-a rare offering in Old Greenwich. .Just minutes from the village, train station, schools, and library, this property combines waterfront serenity with exceptional everyday convenience. Being sold As-Is. Mailbox address: 1 Cove Ridge Lane, Old Greenwich, CT.

1 Hendrie Dr Extension, Greenwich

$1,495,000

3 Beds ⋅ 2 Baths ⋅ 24195428 MLS

Move right in and enjoy this charming 3-bedroom home, immediate occupancy and a quick closing. Whether you're looking to settle in before the school year begins or create your dream home with renovation potential and FAR opportunities, this property offers exceptional flexibility. Ideally located in one of Old Greenwich's most desirable neighborhoods, you'll love the convenience to schools, shops, restaurants, parks, and transportation. The inviting interior is complemented by a wonderful, private backyard--perfect for entertaining, play, or relaxing outdoors. A rare opportunity to own a sweet home in a fantastic community with endless possibilities.

4 Hassake Rd, Greenwich

$2,995,000

4 Beds ⋅ 4 Baths ⋅ 24177489 MLS

Updated with a Modern flair this four-bedroom home is near the water, Tod's Point & located on a quiet cul-de-sac in Old Greenwich. Spacious & bright, there is an open design, sun-filled rooms & hardwood floors. A flexible floor plan makes living & working at home easy. The first floor has a gourmet kitchen w/stainless steel appliances, living room w/fireplace, formal dining room, primary suite with full bath, additional bedroom and full bath. Garden level has 2/3 more bedrooms, two full baths, family room w/access to stone patio, mudroom and laundry. Level and fenced backyard, perfect for entertaining, grilling and relaxing. This home is a short distance to town, schools and Metro North train. Deeded access to view LI Sound at the end of the street. Perfect for today's living & enjoyment.

6 Meadowbank Rd, Greenwich

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