Connecticut’s historic estates combine timeless architecture, lush landscapes, and sweeping waterfront views in some of the state’s most coveted locations.
From the private islands of the Long Island Sound to hilltop retreats with Hollywood history, these properties boast intricate renovations that honor their past while offering luxurious modern amenities. With features like private docks, stables, conservatories, and storied guest lists, these homes are built for both quiet elegance and grand entertaining.
Here’s a look at some of Connecticut’s most remarkable historic estates currently on the market.
1. Historic Rogers Island Estate in Long Island Sound
Built in 1902, the 8,746 square foot main residence on Rogers Island spans 7.65 private acres in the Thimble Islands near Branford, Connecticut. This summer compound includes 10 bedrooms and 8 bathrooms, along with a guest cottage, staff quarters, studio, greenhouse, and mainland access point, all listed at $29,995,000.
Renovated in 2023–2024, the estate features two docks, a saltwater pool, tennis court, putting green, and multiple outbuildings designed for entertaining and large-scale hosting.
Where is Branford, CT?
Branford is a coastal town in New Haven County, Connecticut, located along Long Island Sound. It includes several residential neighborhoods and the Branford River, with a town center featuring shops and historic buildings. The Thimble Islands, a group of small islands off its coast, are a notable local feature. Branford is part of the Greater New Haven area and offers commuter access via rail and highway.
Living Room
Framed by a carved fireplace and a large arched window, the living room arranges white sofas in a U-shape around a circular glass coffee table. A TV is mounted above the mantle, while layered rugs and warm wood flooring add comfort underfoot. Wall paneling, shelving, and accent lighting complete the inviting layout.
Kitchen
Gold hardware and marble countertops line the kitchen, where an oversized island with four stools anchors the space beneath vaulted ceilings. A built-in window seat spans the wall beside a set of tall windows, offering views of the surrounding greenery. Cabinetry wraps around the room in a U-shape, creating a bright and functional workspace.
Game Room
Bold wall art and playful rugs fill the game room, centered around a pool table with deep red fringe and wood legs. Lounge seating and a red coffee table sit at the back of the room beneath a bank of windows. Light fixtures overhead are shaped like sculptural white globes, adding whimsy to the atmosphere.
Pool House
An open-concept layout defines the pool house, where a full kitchen, sectional sofa, and built-in TV face sliding doors leading to the terrace. White walls with beadboard detail and wood-trimmed windows echo the coastal surroundings. Views of the ocean are visible from nearly every angle, with access points to both indoor and outdoor seating areas.
Pool Deck
Set against the water’s edge, the pool deck features a rectangular swimming pool surrounded by rows of lounge chairs and umbrellas. Stone paving lines the area, with a small gazebo positioned at the far end near the rocks and shoreline. Trees and trimmed hedges add privacy to this coastal setup.
Listing agents: Joseph Barbieri, Leslie Mcelwreath of Sotheby’S International Realty, info provided by Coldwell Banker Realty
2. Georgian Revival Estate
Once a summer haven for cultural icons, this 5,920 square foot Georgian Revival estate sits atop nearly 3 acres on Fairfield’s Sasco Hill with panoramic views of Long Island Sound and the Manhattan skyline. Built in 1926 and designed by Francis Hamilton, the 6-bedroom, 9-bathroom home—listed at $10,250,000—has hosted luminaries like Noel Coward, Vivien Leigh, and Richard Rodgers.
Rich in history and elegance, the property features grand interiors, formal terraces, and a celebrated pool featured in the 1968 film The Swimmer.
Where is Fairfield, CT?
Fairfield is a town in Fairfield County, Connecticut, located along Long Island Sound between Bridgeport and Westport. It is home to several beaches, Fairfield University, and Sacred Heart University. The town has a historic town green, a mix of residential neighborhoods, and a commuter rail station on the Metro-North line. Fairfield is part of the Greater Bridgeport area and has a blend of coastal and suburban environments.
Living Room
Centered around a detailed white fireplace, the formal living room displays velvet and patterned armchairs around a small round table. A crystal chandelier hangs above an ornate rug, and framed artwork fills the pale blue walls. Wall sconces and tall windows with drapery add symmetry and balance throughout the space.
Kitchen
White cabinetry with brass hardware lines the kitchen, where a marble island and stainless steel range define the workspace. A casual dining area sits beyond the archway, surrounded by windows that bring in natural light. Subway tile backsplash and dark wood floors add contrast to the otherwise bright design.
Dining Room
Positioned in a windowed bay, the dining room centers a long wood table and antique chairs atop a detailed area rug. Sideboards and classical sconces line the walls, and floor-to-ceiling windows open out to views of the waterfront. A chandelier adds elegance above the central space.
Bedroom
Soft tones and traditional furnishings fill the bedroom, with a large bed, cushioned bench, and area rug anchoring the room. A marble fireplace sits opposite the windows, surrounded by art and figurines on the mantel. Hardwood floors and flowing curtains complete the calm and polished setting.
Backyard and Pool
Expansive lawns stretch from the brick home to a pool area on the opposite end, where a small pool house stands beside a paved deck. A path leads past hedges and flower beds to a symmetrical garden, anchoring the outdoor space. Tall trees and surrounding fences provide privacy across the wide estate.
Listing agents: Wendy Ryan, Andrew Whiteley of Brown Harris Stevens, info provided by Coldwell Banker Realty
3. Expansive 1820 Estate Overlooking Lake Waramaug
Set on over 230 acres in Litchfield County, Connecticut, this 7,528 square foot estate includes 9 bedrooms and 12 bathrooms across two main houses, a guest house, guest cottage, and staff quarters. Built in 1820 and owned by the same family for 70 years, the property features a 12-stall stable, carriage barn, in-ground pool, and trails leading to natural springs and a historic rocky outcrop.
Listed at $12,995,000, the compound blends historic significance with sweeping lake views and equestrian amenities just two hours from Boston and Manhattan.
Where is Warren, CT?
Warren is a rural town in Litchfield County, Connecticut, located in the northwestern part of the state. It is bordered by Lake Waramaug, a popular spot for boating and scenic views. The town is primarily residential and agricultural, with historic homes and open land. Warren is part of the Northwest Hills region and shares regional services with nearby towns.
Sunroom
Floor-to-ceiling windows wrap around this bright sunroom, letting in garden views from every angle. Seating includes two red wingback chairs and a floral-print sofa arranged around a small set of coffee tables. Vintage window valances and layered textiles add a cozy atmosphere to this corner of the house.
Dining Area
Wooden beams stretch across the ceiling above a large dining table with spindle-back chairs placed on a patterned rug. In the middle of the open space sits a bar nook with stools, dividing the dining section from a cozy living area with armchairs and a fireplace. Built-in cabinetry and rustic paneling wrap around the entire room, unifying both functions into one seamless environment.
Study
Bookshelves line the back wall of the study, surrounding a central desk positioned to face the fireplace. A tufted red ottoman and patterned sofa fill the space between the shelves and the hearth. Framed artwork and artifacts personalize the paneled walls and built-in cabinetry.
Bedroom
Multiple windows frame treetop views in this second-level bedroom with soft blue walls. A carved wood bed with pale bedding is paired with traditional nightstands, a dresser, and a sitting area. The rug beneath spans nearly wall to wall and ties in the warm hues of the curtains and accessories.
Horse Barn
Symmetrical wooden stalls with black metal grills line both sides of this long, central hallway in the horse barn. A pitched roof with exposed rafters and overhead lighting runs the length of the space. The floor is wide-planked wood, leading directly out to double barn doors on each end.
Listing agent: Pat Lahoud of William Pitt Sotheby’S Int’L, info provided by Coldwell Banker Realty
4. Waterfront Farmhouse Retreat
Built in 1904 and fully renovated, this 4,791 square foot farmhouse in Norwalk, Connecticut, offers 5 bedrooms and 4 bathrooms on the scenic shores of Gregory Point. Listed at $4,950,000, the property includes a stationary pier with a floating dock, ideal for boating enthusiasts, and features expansive harbor views from nearly every room.
The home also includes a chef’s kitchen, wraparound porch, bluestone patio, and multiple living spaces, combining historic charm with modern coastal living.
Where is Norwalk, CT?
Norwalk is a coastal city in Fairfield County, Connecticut, located on Long Island Sound. It features a working harbor, the Maritime Aquarium, and a historic district in South Norwalk (SoNo). The city has multiple commuter rail stations on the Metro-North line, linking it to New York City. Norwalk also includes neighborhoods like Rowayton and East Norwalk, blending residential areas with commercial and cultural attractions.
Living Room
In the main living room, built-in cabinetry surrounds a stone fireplace that anchors a seating area with a large sectional and patterned armchairs. The design continues with white shiplap walls, light wood flooring, and recessed lighting, while windows and doorways open to adjacent rooms. Through one of these openings, a second seating area is visible with similar finishes and another fireplace feature.
Dining Room
Next to the living space, a waterside dining room frames a wide view of the harbor through large windows and glass doors. This part of the house features a fireplace with a stone surround and white built-ins, paired with a wooden dining table flanked by plush seating. The room is styled with an area rug, decorative shelf items, and coastal artwork.
Kitchen
In the kitchen, clean lines and modern function are brought together with white cabinetry, stainless steel appliances, and a large marble island with counter seating. The space includes a blue tile backsplash and a small wine fridge, adding utility and visual texture. Open shelving and a vibrant rug bring casual character to the room’s otherwise sleek layout.
Family Lounge
Another sitting area, positioned at a corner with panoramic water views, includes multiple armchairs and sofas arranged around a large rug. The entire space is surrounded by oversized windows that overlook a private dock and shoreline beyond. Minimal decor and a bright finish maintain focus on the natural scenery.
Bedroom
Inside the bedroom, a pitched ceiling with exposed beam and recessed lighting crowns a space centered around a bed facing water-facing glass doors. A soft-toned area rug, light wood floor, and coastal furnishings keep the palette consistent with the rest of the home. The French doors open directly onto a small balcony with a view of the docks and marina.
Listing agent: Meghan Gatt of William Raveis Real Estate, info provided by Coldwell Banker Realty
