Explore Connecticut’s Most Elegant Mansions for Sale Starting at $35 Million

Explore Connecticut’s Most Elegant Mansions for Sale Starting at $35 Million

Photo: Douglas Elliman Real Estate

Located in Branford, Connecticut, Rogers Island is the epitome of luxury and sophistication. Priced at $35 million, this stunning estate spans 7.7 acres of meticulously designed property, offering both privacy and expansive views of the Long Island Sound.

WRKI and WINE logo
Get our free mobile app

Originally built in 1902, the main residence has been thoughtfully renovated to meet modern standards of comfort and style, while maintaining its classic architectural charm. The estate also includes a four-bedroom waterfront guest house, creating the perfect retreat for family and guests alike. With an array of outdoor amenities and serene spaces, Rogers Island is not just a home—it’s an experience.

The estate is designed to cater to every need and desire, from leisure and relaxation to active living. The outdoor spaces are particularly impressive, with formal gardens, meandering trails, and a koi pond providing the ideal setting for peaceful reflection or entertaining guests. Rogers Island also boasts three private beaches, two docks, and an elegant pool house for ultimate indulgence. Whether you enjoy sunbathing by the pool, strolling through lush gardens, or engaging in tennis matches on the private court, every corner of this expansive estate is curated for your enjoyment.

But those are just fancy ass words, what they amount to is this place is heaven on Earth. I don't know how these rich folks do it, I'd never leave this property, I cannot see a reason.

Listing: Douglas Elliman Real Estate/Jennifer Leahy

Explore Connecticut’s Most Elegant Mansions for Sale Starting at $35 Million

This is 0 Rogers Island, a $35 million estate located at 0 Rogers Island, Branford, CT 06405. Take a closer look at the remarkable features that make this one of the most coveted properties in the world. From its breathtaking outdoor spaces to its luxurious amenities, this estate offers an unparalleled living experience.

Gallery Credit: Lou Milano

I'm serious, WHY would you leave this property? I'm trying my darndest to come up with a scenario that would get me off this island and I just cannot find one.

Check out the Ethan, Lou & Large Dave Podcast on Apple and Spotify

Is This the Best $25 Million Home in Connecticut? A Look Inside a Waterfront Paradise

Located at 1131 Sasco Hill Road in Fairfield, CT, this exceptional estate offers 11 acres of waterfront living with 450 feet of Long Island Sound frontage. Designed by architect Jason Chai, the home blends Swedish, Dutch, and Moorish elements to create a space that is both luxurious and inviting. At least that is what I'm told, I understand about 12% of what I just wrote. Let's take a look around. 



Gallery Credit: Lou Milano

Exquisite Connecticut Estate with Custom Grounds on Sale for $34 Million

Resting atop one of the highest points in Greenwich, Connecticut, at 7 John Street, Robin Hill Farm and Smokey Hill Farm offer an extraordinary opportunity to own a truly majestic family estate. It has 10 bedrooms, 12 full baths, 4 half-baths, and a range of luxurious living spaces —and it can all be yours for a cool $34.5 million. Let's take a look around.


Gallery Credit: Lou Milano

Discover Luxury Living in a $3.9 Million Putnam County Mansion

Discover the stunning residence at 40 High Ridge Road in Garrison, NY, where luxury meets simplicity in a breathtaking contemporary design. Perched on six acres, this home offers expansive views of the Hudson River and a seamless flow between indoor and outdoor spaces. With its open-plan layout, luxurious amenities, and prime location, this property is a true oasis, perfect for those seeking a serene lifestyle without sacrificing modern comforts. This can all be yours for a cool $3.9 Million. 


Gallery Credit: Lou Milano

Luxury Redefined: Take a Tour of this $12 Million Home in North Salem

So, you’ve got a cool $12 million lying around and are in the market for a mansion that makes Buckingham Palace look like a starter home? Well, have we got a place for you! Located at 123 Dream Lane, North Salem, NY, this breathtaking estate spans a massive 83 acres and is a stunning replica of the English Georgian masterpiece “Salutation.” With 10,700 square feet of pure luxury, this home is designed to impress at every turn. As you explore, you’ll find expansive grounds perfect for outdoor activities, a serene English garden, top-notch equestrian facilities, and luxurious indoor amenities like a spa-like indoor pool and a state-of-the-art gym. Each room is crafted for comfort and sophistication, from the grand entrance with its dramatic staircase to the cozy library and elegant dining spaces. Get ready to step into a world where luxury meets tranquility—let’s take a closer look inside this $12 million mega-estate!


Gallery Credit: Lou Milano

Paradise Awaits: Explore This $50 Million Luxury Estate in Connecticut

Step inside this mind-blowing estate, the true essence of luxurious coastal living. From the meticulously designed interiors to the stunning outdoor amenities, every feature of this home reflects a harmonious blend of elegance and comfort. Take a virtual tour into this idyllic waterfront estate in Connecticut that is on the market for $50 million. 

This is 545 Indian Field Road in Greenwich, CT.

Gallery Credit: Lou Milano

Welcome to The Falls: Stunning $8 Million Modern Retreat in Connecticut

Welcome to "The Falls, where you can enjoy magical views of the Litchfield Hills while being just minutes from the award-winning restaurants of Kent Center. Inside, you’ll find open space, curved walls, and a view of the waterfall from the living room. "The Falls" has a tennis court, pool and spa, and expansive meadows, this estate is truly a slice of paradise—yours for $8 million.

Let’s take a virtual tour together!


Gallery Credit: Lou Milano

Lap Of Luxury: Stunning 10-Acre Estate On The NY-CT Border For 16+ Million

A 10-acre estate tailored for sports enthusiasts has come on the market in Westchester County, just north of New York City, with an asking price of $16.5 million. See what a monster-sized bucket of dough can buy you on the NY/CT border.

Listing: Compass

Gallery Credit: Lou Milano

Luxury Meets Privacy: Discover Old Greenwich’s Exclusive Peninsula

28 East Point Lane is a luxury address in Old Greenwich, CT that happens to rest on a peninsula. If you have a metric f--- ton of money I have good news, It recently hit the market for $12.5 Million. 

Gallery Credit: Lou Milano

All Along the Posh Tower, Glorious $15 Million Connecticut Estate Hits the Market

This home is not a home it’s not an address, it’s 3 full addresses in a gated community, that sits inside a gated community. It’s a playground, a trophy and a showpiece for anyone who can afford the price tag. Here’s how I will do this; the top line will be what I’d say to you, if I was the realtor, and the bottom line will be wiseass commentary for my own sick amusement. 

Gallery Credit: Lou Milano

Categories: Articles

More From WRKI and WINE