Old Greenwich CT Real Estate & Homes for Sale

Stunning Colonial in Havemeyer Park, Old Greenwich, on a 0.38-acre cul-de-sac lot, offers resort-style living with a pool, deck, and built-in barbecue. Inside, find hardwood floors and sunlit rooms. The main floor includes a living room, family room with fireplace, breakfast room, gourmet kitchen with Sub-Zero and Wolf appliances, dining room, powder room, and mudroom. The second floor boasts a primary suite with tray ceiling, walk-in closets, spa bath, plus three bedrooms, hall bath, and laundry. A private guest suite is above the garage with a separate entrance.The lower level features a full bath, playroom, utility room, and bonus space. Minutes from Old Greenwich Village, Metro North, and Tod's Point beach.

Move right into this beautifully updated home ideally located in the heart of Old Greenwich - just around the corner from shops, restaurants, and the train. Offering the perfect blend of charm and convenience, this residence is designed for comfortable living and effortless entertaining. This spacious and stylishly updated home offers a fantastic layout with an open kitchen and family room that overlooks a fully fenced backyard - ideal for everyday living and entertaining. The main level also features elegant formal living and dining rooms that flow beautifully and feature excellent natural light. Upstairs, you'll find a spacious and private primary suite along with three additional well-proportioned family bedrooms. The finished lower level (920 sq ft) offers even more flexible space, including a large playroom, fifth bedroom, and a full bathroom. Total living space is 4,224 sq ft. The home is not located in a flood zone. Don't miss this rare opportunity to live in one of Greenwich's most desirable neighborhoods!

Stunning fully renovated and expanded Colonial in the heart of Old Greenwich seamlessly blends timeless charm with modern luxury. Set on a quiet, tree-lined street just minutes from Old Greenwich Village, Metro North, and Tod's Point beach, this 5-bedroom, 4-bath home offers refined living in a prime location. The brand-new chef's kitchen showcases custom cabinetry, premium fixtures and finishes, and top-tier appliances including a Sub-Zero refrigerator and Wolf range. The kitchen opens to a sunlit dining room and inviting living room, while the family room features a cozy fireplace-perfect for entertaining or relaxing. A generous upstairs landing leads to five spacious bedrooms, including a vaulted-ceiling primary suite with a luxurious spa bath and soaking tub. The finished lower level Stunning fully renovated and expanded Colonial in the heart of Old Greenwich seamlessly blends timeless charm with modern luxury. Set on a quiet, tree-lined street just minutes from Old Greenwich Village, Metro North, and Tod's Point beach, this 5-bedroom, 4-bath home offers refined living in a prime location. The brand-new chef's kitchen showcases custom cabinetry, premium fixtures and finishes, and top-tier appliances including a Sub-Zero refrigerator and Wolf range. The kitchen opens to a sunlit dining room and inviting living room, while the family room features a cozy fireplace-perfect for entertaining or relaxing. A generous upstairs landing leads to five spacious bedrooms, including a vaulted-ceiling primary suite with a luxurious spa bath and soaking tub. The finished lower level offers a full bath, playroom, utility room, and bonus space ideal for a guest room, gym, or au pair suite. Outside, a private backyard oasis features a sparkling pool and space for unforgettable gatherings. Every detail reflects exceptional craftsmanship, thoughtful design, and effortless elegance. This rare, move-in-ready gem offers sophisticated living in one of Greenwich's most sought-after neighborhoods. Above Grade:2608 sqft Below Grade 602 sqft

There is more than meets the eye in this sweet colonial on oversized lot in R7 zone. A prior expansion creates flexible space on the first floor. A spacious living room with fireplace is flanked by an office/playroom, ample formal dining room and a first floor primary bedroom with full bath which can alternately be used as a family room. Archways lend a special charm to the formal rooms. The kitchen offers a sunny breakfast area with adjacent mudroom/laundry area. Walk out to a spacious deck overlooking the level fenced yard and heated pool. On the second floor there is another primary bedroom with ensuite bath, and two additional bedrooms share a hall bath. Bring your own style and personality to this lovely home with so much potential! Just 1/2 mile to Binney Park and less than a mile to Old Greenwich trains station and all that downtown Old Greenwich has to offer. Only a 7 minute drive to Todd's Point.

This stunning direct waterfront home boasts panoramic views of the Long Island Sound, Manhattan skyline, Stamford Harbor, Greenwich Cove and the beach at Tod's Point. Designed by renowned shingle-style architect Lyman Perry, and custom built and uniquely sited within its own context, framing magnificent views to ocean and landscape. Sparkling water views can be enjoyed from every room, including the great room, a gourmet kitchen with double marble topped islands, a stylish oversized paneled library with window seat and the sunny breakfast room. Temperature controlled custom crafted wine cellar. Wraparound porches on the first floor and two balconies on the second floor and one on the third make indoor/outdoor living a breeze. The second floor features a spacious primary suite with balcony with luxurious bathroom with soaking tub, private water closet, separate shower and walk-in closet. There is also a custom office area with access via a spiral staircase to a rooftop lookout. Second floor also features four ensuite bedrooms, and a spacious family room with a vaulted ceiling. Outdoor amenities include a waterfront pool, a separate spa, sports court/pickle ball court, an outdoor kitchen and beautifully landscaped lawn. Located in the private Lucas Point Association, the residence enjoys easy access to the private beach and marina. This is a rare opportunity to own a truly exceptional waterfront property presented in turnkey condition with the ability to enlarge or just enjoy as is.

This unparalleled custom-built modern waterfront estate, winner of 2021 HOBI-award, is a true oasis with 300'+ water frontage, pool, guest house, boat house, spa, expansive terraces integrated with gardens and deep water pier. Joeb Moore + Partners, Arthur Dunnam for Jed Johnson Studio, Reed Hilderbrand & Prutting Custom Builders collaborated on this spectacular LEED certified 13,428 sf compound defined by seamless indoor/outdoor living & entertaining spaces, geo-thermal heating/cooling system & the best of smart home technology. Stunning open floor plan interior, brimming with luxurious details, boasts dramatic floating three-story staircase; true chef's kitchen with extraordinary pantry, scullery and wine room; floor to ceiling glass imported doors and windows envelop the home with Multiple custom offices. Exceptional Primary Wing. Breathtaking open water views across to Long Island from most every room. A very unique opportunity.

Nantucket Vibes in the Heart of Old Greenwich-Tucked just south of the village in one of the most sought-after spots, this classic home blends timeless charm with an effortlessly modern flow. Set back from the street with a welcoming mahogany wraparound porch, the home opens to a bright, expansive layout designed for easy living and entertaining. Inside, airy, open-concept living spaces flow from a sweeping foyer into formal living and dining areas that seamlessly connect to a chef's kitchen complete with pro-grade appliances and space to gather. The sunny breakfast nook and cozy family room (with custom built-ins and a fireplace) open to a glass-wrapped solarium. French doors lead out to a stone patio and private backyard, perfect for lazy weekend lounging or summer hosting. Upstairs, the primary suite feels like a retreat nestled in the treetops, offering multiple closets and a spa-like bath. Oversized windows flood the home with natural light throughout. Classic meets cool in this stylish shore colonial, steps from everything Old Greenwich has to offer.

This rare three-bedroom, four-bath triplex is located in the sought-after Old Greenwich Gables complex with pool and fitness center. This exceptional home features a spacious ground floor with a large kitchen that opens to the family room a great room with fireplace and access to a private terrace perfect for outdoor entertaining. The main bedroom boasts soaring ceilings, a sitting area with its own fireplace and a private balcony for serene moments. The second floor offers two additional bedrooms and a full bath, while the versatile third floor provides an ideal space for guests or an office. Enjoy the convenience of being just a sidewalk away from the train, town, Dundee elementary school, and Binney Park, plus a short distance to the beach. Parking Space #96 and the storage is #148.

Move in for summer! Enjoy breathtaking views and stunning sunsets from this hidden gem on Shorelands waterfront. Quintessential beach cottage with approved dock plan. Ideal for weekend getaways, summer escape or year-round living. Perfectly located south of the village of Old Greenwich, close to shops, restaurants, train, school and beach. The first floor features a large living room and dining room with incredible water views and sliders to deck, kitchen with breakfast bar seating, spacious bonus room and full bath. Three bedrooms and a full bath comprise the second floor with amazing water vistas. Live in home as is or be inspired by potential new home design by James Schettino Architects. Enjoy a private beach and dock as part of this desirable association.

Stylish five-bedroom Contemporary provides a modern oasis with stunning pool, Ipe wood decks and secluded backyard on a quiet drive south of the village near shops, trains, school and beach. Striking architectural details ranging from maple wood floors, glass stair railings on three levels, high ceilings, expansive windows, sliding doors and skylights enhance 4,286 sq. ft. interior. Boasts sleek kitchen with Gaggenau appliances, Geoluxe counters and butler's pantry. Family and dining rooms with shared linear fireplace and bonus room, all with deck access for outdoor entertaining. First floor guest suite or office. Second floor offers primary suite with spacious closet and luxurious bath plus three more ensuite bedrooms. Lower level with media room, mudroom and garage for up to eight cars.

Location Location Location! Close to everything! This property has all the bells and whistles right in town! 1st floor opens up to a 2 story foyer, gourmet kitchen compliments the great room/FP 20ft ceilings with access to patio overlooking the beautiful yard, DR, laundry/mudroom/half bath with garage access, office/possible bdrm/full bath make up the first fl. The Primary bdrm/bath, 3bdrm/2bath make up the 2nd fl. LL offers another en-suite bdrm, gym ,media rm, play rm, full bath with outside access. This house has great space with tremendous flexibility! Additional Information: ParkingFeatures:2 Car Attached

This just built shore colonial is on one of Old Greenwich most desirable streets. This is truly a lifestyle most only dream of. Minutes from Old Greenwich Village, Metro north train and Tod's Point public beach. This 6 bedroom, six full and two half baths new construction embodies architectural details and luxurious amenities. Open concept first floor has a fabulous cook's kitchen, adjoining dining area opening to expansive deck overlooking in ground pool, great room with fireplace, and living room and mud room make up first floor. Second floor there is primary suite with multiple walk-in closets and bath with radiant heat, 3 double bedrooms all with en-suite baths. Third floor has bedroom, bath, office and 1/2 bath and large balcony overlooking property. Lower level contains playroom, bedroom, media room, gym and full bath and access to outside. Fenced in yard for privacy.

For true privacy and beauty, look no further than 35 Park Avenue. The magical landscape brimming with specimen plantings has been artfully designed on nearly half an acre in the heart of Old Greenwich, close to the town center, schools, parks, and beaches. Inside, the home epitomizes understated luxury, featuring gorgeous natural light, oak floors, and large windows showcasing the remarkable setting. Highlights include an elegant dining room, a sunlit living room with a fireplace, and a chef's kitchen with a soaring ceiling and sitting area. French doors open front and back terraces, while a cozy family room and 6 spacious bedrooms add further allure. Outside, shady sitting areas, a wisteria-covered pergola, and a pool site offer the chance to relax and refresh amid sublime surroundings.