What happens when more than 150 Brown Harris Stevens agents and executives from across the company descend on Connecticut for a day of extraordinary real estate?
A whole lot of house envy. And an even greater appreciation for the power of being connected.
Our recent Connecticut house tour brought colleagues together to explore seven exceptional properties across Westport, Darien, Stamford, and Greenwich. From sprawling waterfront compounds to beautifully designed family retreats, the homes offered something for every taste. But the day was about more than impressive architecture and gorgeous interiors.
Click here to view the photo gallery from the event!
Seven Homes Worth Talking About
35 Dogwood Lane, Westport
Price Upon Request | Represented by Mark Gilrain and Dan McCamblau
Room to roam might be an understatement. Set on five private acres, this impressive six-bedroom Westport estate offers nearly 8,900 square feet of living space, four full bathrooms, and two half baths. With its sprawling grounds, generous proportions, and exceptional privacy, it’s the kind of property that makes escaping the city feel like a serious upgrade.
4 Sherwood Island Lane, Westport
$10,500,000 | Represented by Andrew Whiteley and Wendy Ryan
Waterfront living doesn’t get much more spectacular than this. Set on approximately 20.85 acres in Greens Farms, this seven-bedroom estate boasts extraordinary views across Sherwood Island Park and Long Island Sound. Held by the same family for more than 65 years, the property features guesthouses, a tennis court, indoor pool, pool house, and formal gardens. It’s a rare opportunity to create a true multigenerational waterfront compound.
700 Hollow Tree Ridge Road, Darien
$3,699,500 | Represented by Serena Richards and Becky Munro
With five bedrooms, five full bathrooms, a powder room, and 5,500 square feet, this Darien residence delivers the kind of generous living space today’s buyers love. An appealing combination of scale and flexibility makes it well suited for everything from everyday family life to hosting a houseful of guests.
20 Oak Street, Greenwich
$4,950,000 | Represented by Matthew Tallett
There’s room to entertain, and then there’s this. Spanning approximately 8,600 square feet across four elevator-accessible levels, this five-bedroom Greenwich home features a chef’s kitchen, wine cellar, fitness studio, and expansive entertaining spaces. Set on 0.70 acres along a private lane just minutes from Greenwich Avenue, the property even has its own golf simulator. Fore!
$4,199,000 | Represented by Serena Richards
At 6,535 square feet, this five-bedroom Darien home offers plenty of room to spread out in style. With six full bathrooms and two half baths, its generous layout is particularly appealing for buyers seeking both comfortable family living and space to entertain.
$1,595,000 | Represented by Jessica Gaglio
Proof that you don’t need seven bedrooms to make a big impression. This three-bedroom Stamford home offers nearly 4,000 square feet of living space, three full bathrooms, and two half baths. Its substantial proportions provide plenty of flexibility for entertaining, working from home, or simply enjoying a little extra breathing room.
$11,950,000 | Represented by Rob Johnson
Rounding out the tour was this impressive six-bedroom Greenwich estate, featuring seven full bathrooms, a powder room, and more than half an acre of property. With its substantial scale and coveted Greenwich location, this is the kind of luxury residence that makes an impression long after the tour ends.
The Real Highlight? The People.
When an agent in Manhattan has a client considering a move to Greenwich, or a buyer in the Hamptons is exploring a second home in Westport, those personal connections matter. They’re what turn a large geographic footprint into a closely connected community of real estate professionals.
And sometimes, the best way to strengthen those relationships is to get everyone together, open a few beautiful front doors, and see what happens.
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