Connecticut’s luxury real estate market dazzles with its fusion of coastal charm, historic estates, and commuter-friendly opulence. From Greenwich’s waterfront mansions to the wooded elegance of New Canaan and Guilford, each property feels like its own private sanctuary shaped by both heritage and design.
Let’s unveil some of the most expensive homes currently listed in the Constitution State.
5. Riverside, CT – $13,995,000
Designed by Douglas Vanderhorn and completed in 2008, this 9,416 square feet estate in Riverside features 7 bedrooms and 11 bathrooms on 1.77 acres within the Indian Head Association. Offering sweeping views of Long Island Sound, the property includes a pool, multiple terraces, covered porches, and a restored 1929 guest cottage connected to the main house.
Listed at $13,995,000, it also includes beach rights and was built to blend classical design with high-end finishes throughout.
Where is Riverside?
Riverside is a neighborhood in the town of Greenwich, Connecticut, located along the eastern side near the Mianus River and Long Island Sound. It is primarily residential with access to Metro-North rail service into New York City. The area includes schools, parks, and a small commercial district. Riverside shares services and governance with the larger town of Greenwich.
Study
Dark wood paneling surrounds this study, where a black marble fireplace anchors the far wall beneath built-in shelves. French doors open to a water view and patio, framed by tall windows. Seating includes a leather tufted sofa, zebra-patterned armchairs, and a trunk-style coffee table.
Kitchen
Marble countertops and a large island with a built-in butcher block define the layout of the kitchen. Cabinetry in white and black contrasts with a red oven and paneled appliances. Entryways lead into adjacent formal and informal dining areas.
Theater Room
Red walls and ceiling panels surround the home theater room, equipped with black leather recliners and a mounted screen. A movie is projected from the ceiling above, with built-in speakers beneath the screen. The layout suggests a cozy, enclosed entertainment space.
Bedroom
Tall ceilings and a fireplace with a wall-mounted TV create a focal point in the bedroom. A pair of mirrored nightstands flank the upholstered bed placed along one wall. Windows line the opposite side, with a view of the water beyond.
Backyard
Stone and timber walls outline the rear exterior of the house, where a rectangular pool sits at the center of a paved patio. Multiple seating and lounge areas surround the water, including a fire pit setup in one corner. Landscaping includes low hedges and flower borders wrapping the perimeter.
Listing agents: Joanne Mancuso, Amanda Miller of Houlihan Lawrence, info provided by Coldwell Banker Realty
4. Fairfield, CT – $25,000,000
Set at the end of Sasco Hill Road with 450 feet on Long Island Sound, this 19,569 square feet estate spans over 11 acres and includes 6 bedrooms and 11 bathrooms. Built in 2002, it features a private dock, wine cellar, new pool, multi-car garage with art studio, and panoramic water views from nearly every room.
Listed at $25,000,000, the property combines architectural influences from Sweden, the Netherlands, and Moorish design with modern upgrades and expansive coastal grounds.
Where is Fairfield?
Fairfield is a coastal town in southwestern Connecticut, located along Long Island Sound in Fairfield County. It is home to several beaches, Fairfield University, and Sacred Heart University. The town was settled in the 1600s and has a mix of suburban neighborhoods and historic districts. Fairfield also offers commuter rail access to New York City.
Living Room
Bookshelves built into the walls wrap around the living room, framing a stone fireplace and large French doors. Two gray sofas, several lounge chairs, and circular wooden coffee tables sit on a thick cream rug. Red-shaded table lamps add contrast near the end tables and windows.
Sunroom
Curtains stretch floor to ceiling along the glass walls of the sunroom, letting in daylight from all sides. White sofas, woven baskets, and a pair of stools arranged behind a console table define the sitting area. The fireplace in the corner blends into the light-paneled walls.
Kitchen
Cabinetry in soft gray tones fills the kitchen, including glass-fronted storage and a built-in wine cooler on the island. Stainless steel refrigerators, a gas range with hood, and marble countertops complete the layout. Pendant lights hang above the central island with bowls of fruit set for display.
Bedroom
Soft gray paneling and low bookshelves border the bedroom, which holds a gray-upholstered bed and sitting area with modern chairs and tables. A stone fireplace with a carved surround sits on one end, and a small arched window nook offers additional seating. The palette stays muted with light floors and neutral bedding.
Bathroom
Vaulted paneling stretches across the ceiling above this primary bathroom, which features a double vanity with recessed mirrors and wall sconces. A sunken tub surrounded by steps sits beneath an arched alcove next to tall frosted windows. A small vanity table and built-in shelving are arranged opposite the bathing area.
Listing agents: Andrew Whiteley, Wendy Ryan of Brown Harris Stevens, info provided by Coldwell Banker Realty
3. New Canaan, CT – $25,500,000
Originally built in 1937 and set on 52 acres in Fairfield County, this 14,266 square feet French-style estate includes 9 bedrooms and 14 bathrooms. Once owned by copper heiress Huguette Clark, the property has been restored with updated interiors and includes a pool, tennis court, wildflower gardens, and two additional cottages—a 2-bedroom, 1,096 square feet caretaker’s home and a 1,296 square feet exercise pavilion.
Listed at $25,500,000, the estate blends historic character with modern design across expansive grounds.
Where is New Canaan?
New Canaan is a town in southwestern Connecticut, located in Fairfield County near the New York state line. It is known for mid-century modern architecture and a strong residential character. The town developed as a commuter hub with access to New York City by rail. New Canaan also features a walkable downtown and cultural institutions like the Glass House.
Living Room
Living room centers around a cream-colored sectional with matching sofas and wooden armchairs arranged over a large woven rug. Full-length windows line the wall, drawing in natural light across the entire space. A simple fireplace is built into the back wall beneath a grid of framed artworks.
Library
Library sits adjacent to the living room and is wrapped with floor-to-ceiling built-in bookshelves. Two angular desks and clear chairs are placed in the center, surrounded by reading nooks and vintage furnishings. A large dome-shaped pendant light hangs overhead.
Kitchen
Kitchen features a checkered black-and-white tile floor and stainless steel counters lining three walls. Two ranges are installed beneath a large commercial-style hood, and an island with built-in seating sits at the center. Natural light enters through tall windows at the far end.
Bedroom
Bedroom features a large bed on the left, with seating and a coffee table arranged across the room near tall windows. Two separate workspaces are positioned at each end, offering flexibility and function. The same wide herringbone floors and minimalist white walls carry throughout.
Bathroom
Bathroom combines a soaking tub, two lounge chairs, and a marble fireplace beneath two wide windows. Twin vanities are placed on the left, and sculptural elements are positioned in the corners. Marble floors span the entire room with white fixtures throughout.
Listing agents: Mary Higgins, Rob Johnson of Brown Harris Stevens, info provided by Coldwell Banker Realty
2. Guilford, CT – $35,000,000
Spanning 13.03 acres in Sachems Head, this waterfront estate includes a 5,354 square feet main residence built in 2009 with 6 bedrooms and 5 bathrooms. Priced at $35,000,000, the property features 1,900 feet of shoreline, 3 docks, a boat lift, pool, spa, vineyard, tennis court, go-kart track, and multiple structures including a 3-bedroom guest house, in-law quarters, and a carriage house.
The combined offering includes development potential or use as a private compound with extensive outdoor and recreational amenities.
Where is Guilford?
Guilford is a town on the southern coast of Connecticut, located along Long Island Sound in New Haven County. It was settled in 1639 and features a well-preserved historic town green and colonial architecture. The town includes shoreline access, marinas, and nature preserves. Guilford is part of the New Haven metropolitan area.
Living Room
Main seating area in this living room centers around two sofas and two armchairs, all arranged to maximize the view across the harbor. Floor-to-ceiling windows wrap around the perimeter, bringing in natural light and access to the patio beyond. Decor includes a Monopoly-themed poster and a modern console table.
Dining Room
Glass panels in the shelving wall divide this dining room from an adjacent area while keeping the layout open. Seating for twelve surrounds a modern wood dining table that faces double glass doors leading to a water view. Statement lighting is suspended above, positioned between ceiling beams.
Kitchen
Multi-tone cabinetry frames the space in this kitchen, where red barstools line the black stone island beneath hanging pendant lights. A built-in microwave and visible countertop appliances suggest a space designed for regular use. Sliding glass doors provide immediate access to the yard outside.
Reading Nook
Upper-level hallway includes built-in cubbies with navy cushions and bright round pillows, paired with circular windows and mounted reading lights. Continuous wood cabinetry frames the top and bottom of the corridor. The far end opens to a staircase with narrow railings.
Library Tower
Circular room at the top of a spiral staircase houses bookshelves and a panoramic view through tall windows. The wood-clad ceiling and walls enclose a compact study nook lined with colorful stools and decorative objects. Glass doors offer access to an outdoor balcony above the water.
Listing agents: Joe Piscitelli, John Guarino of Coldwell Banker Realty
1. Greenwich, CT – $44,600,000
Completed in 2014 within the private guard-gated Mead Point Association in Greenwich, this 12,492 square feet waterfront home includes 6 bedrooms and 8 bathrooms on 1.6 acres. Designed with Georgian architecture and inspired by a 1928 stone residence, the estate features a private beach, dock, waterfront pool, and outdoor kitchen.
Listed at $44,600,000, the property also includes a gym, sauna, wine storage, and deeded access to the association’s community beach.
Where is Greenwich?
Greenwich is a town in southwestern Connecticut, located along the Long Island Sound and near the New York state border. It is part of the New York City metropolitan area and serves as a residential and financial hub. The town includes several distinct neighborhoods and has a long history dating back to the 1600s. Greenwich is also home to hedge funds, historic estates, and coastal parks.
Foyer
Checkerboard tile leads to a sweeping staircase at the back of the foyer, curving up past framed paneling and a gallery of wall sconces. A narrow table stands beneath a mirror, with floral arrangements adding a touch of softness. The space opens through a wide archway into adjoining rooms.
Living Room
Natural light floods the living room from towering windows framing a fireplace centered on the back wall. A tufted leather sofa faces a wide wood coffee table, with open shelving and side seating placed along the perimeter. High ceilings and a second-floor balcony overlook the open space.
Dining Room
Glass double doors and a circular window bring brightness into the dining room arranged with a long wood table and six green velvet chairs. The chandelier overhead echoes the ornate design of the white ceiling molding. A sideboard and mirror are placed against the far wall, maintaining balance in the layout.
Kitchen
A large island with white paneling and green-cushioned chairs anchors the kitchen under a trio of glass pendant lights. The counters and backsplash are finished in white marble, blending into custom cabinetry. Stainless appliances and a large range hood give a contemporary touch to the classic design.
Bedroom
Tall windows in the bedroom look out to the water, flanked by a white chaise and writing desk on one side and a king bed with teal bench on the other. Matching nightstands and lamps complete the setup under a soft chandelier. The ceiling pitches upward, expanding the volume of the room.
Listing agent: Leslie Mcelwreath of Sotheby’S International Realty, info provided by Coldwell Banker Realty
