Welcome to an exclusive look at six of Westport, CT‘s most magnificent mansions, where luxury, elegance, and charm come together in perfect harmony. Nestled in one of Fairfield County’s most desirable towns, these sprawling estates offer a glimpse into the pinnacle of refined living.
In this post, we’ve compiled captivating video tours showcasing the unique features, breathtaking interiors, and expansive grounds of these remarkable homes. Whether you’re in the market for your dream home or simply enjoy exploring exquisite real estate, these mansions are sure to inspire and amaze.
So, sit back, press play, and let these stunning Westport properties whisk you away to a world of unparalleled opulence.
$7,250,000 (Sold)
This extraordinary modern estate by Skyview Builders offers unparalleled luxury and privacy on 2+ acres in Westport’s prestigious Coleytown area, adjacent to the Paul Newman-Poses Nature Preserve. Defined by expansive triple-glazed windows, cutting-edge construction, and seamless indoor-outdoor living, this turnkey home features a gourmet kitchen, heated porch, pool, spa, and an optional guest house for the ultimate compound experience.
$6,700,000 (Sold)
Step into the world of Martha Stewart with an exclusive video tour of her first home, 48 Turkey Hill in Westport, Connecticut. Explore the enchanting grounds, exquisite gardens, and thoughtfully renovated interiors of this iconic estate while uncovering its rich history and transformation.
$8,500,000 (Sold)
Experience the perfect fusion of art and life at this contemporary masterpiece on Saugatuck Island, offering sensational water views from every angle. With features like a heated pool, private dock, rooftop terrace, and a stunning chef’s kitchen, this luxurious home redefines coastal living.
$4,750,000 (Sold)
Discover effortless waterfront living at this Nantucket-style 5-bedroom home on Saugatuck Shores’ Bermuda Lagoon, complete with a private sandy shoreline and deep-water dock. With timeless craftsmanship, seamless indoor-outdoor spaces, and luxurious details like a gourmet chef’s kitchen, expansive Bluestone patio, and a serene primary suite with water views, this home is designed for making memories by the shore.
$6,150,000 (Sold)
Perched atop exclusive Minute Man Hill, this coastal estate offers breathtaking Long Island Sound views, unparalleled luxury, and ultimate privacy on 1.42 impeccably landscaped acres. Featuring exquisite craftsmanship, a saltwater pool, room for a tennis court, and thoughtfully designed interiors—including a gourmet kitchen, stunning third-floor lounge, and walk-out lower level with a custom wine cellar—this home is a masterpiece of coastal living.
$4,550,000 (Sold)
Located in the Westport’s Compo Beach neighborhood, this transitional modern luxury home by Tomas Brothers Builders showcases impeccable craftsmanship and sophisticated design. With 6 bedrooms, 8 baths, sun-filled interiors, and stunning outdoor spaces—including a pool, spa, outdoor fireplace, and built-in grill—this 6,800 sq ft masterpiece offers the perfect blend of style and functionality.
Cress is an innovative real estate advisory firm representing buyers and sellers of high-end properties throughout Fairfield County, CT and beyond. On the sell side, Cress delivers marketing-driven support designed to expand visibility and maximize outcomes. Through its co-listing model, Cress partners alongside listing agents to provide digital-first distribution, high-quality content creation, and proactive demand generation strategies that extend well beyond traditional MLS exposure.
On the buy side, Cress offers flat-fee representation and commission rebate programs that bring efficiency and transparency to luxury transactions while maintaining a high standard of service. Known for strategic insight, modern marketing execution, and deep local knowledge, Cress provides a smarter, more aligned approach to buying and selling real estate.
For more information, visit www.callcress.com.
Doug Cress
(212) 203-5251
doug@cress.co
License #RES.0832278
Fairfield County, CT
Enterprise Realty Inc.
License #REB.0751297
45 Huntington Plaza
Shelton, CT 06484
