Connecticut real estate runs on old money, new money, and hedge fund bonuses. Mansions hide behind hedges in Greenwich, while quiet power brokers swap properties along the Gold Coast without making noise. The state’s shoreline, dotted with estates that look more like institutions, trades privacy for price tags. Up north, country homes sit on land that’s been owned longer than most companies have existed.
Here’s a look at the five most expensive houses on the market in Connecticut.
5. New Canaan, CT – $9,188,000
Set on 4 acres in New Canaan, this $9,188,000 estate spans 16,255 square feet and includes 6 bedrooms and 10 bathrooms. Designed by architect James E. Gearity, the home features a 30-foot foyer with a spiral staircase, 7 fireplaces, a chef’s kitchen with SubZero and Viking appliances, and a 35.5-foot vaulted great room with hand-carved buttresses.
The primary suite includes a Juliet balcony, vaulted ceilings, a freestanding tub, and an 800-square-foot dressing suite. Additional features include a guest suite with private entrance, a media room, wine grotto, pool, and dining pavilion.
Where is New Canaan?
New Canaan, Connecticut, is a residential town in Fairfield County known for its mid-century modern architecture and walkable downtown. The town center includes shops, restaurants, and a train station with service to New York City. Surrounding neighborhoods feature parks, schools, and wooded residential areas. New Canaan is also home to cultural institutions like the Glass House and local art centers.
Foyer
Curved twin staircases wrap around a double-height foyer with full-length windows stretching up toward a crystal chandelier. Arched wooden beams frame the entry space, connecting visually to the white walls and trim. A circular glass table with a floral arrangement stands at the center of the tiled floor. Natural light fills the area from multiple directions.
Living Room
Dark blue paneling and exposed structural beams define a moody living room with a central fireplace and built-in shelving. Recessed lights dot the ceiling, highlighting a large framed painting above the mantel. Two cream-colored sofas and a pair of armchairs surround round coffee tables on a plush rug. Small windows flank the fireplace, allowing minimal daylight into the space.
Dining Room
Black dining chairs surround a long rectangular table positioned below a layered chandelier. A carved white fireplace sits between two tall windows, with a pair of armchairs placed at the hearth. Built-in niches display sculptural vases lit from above. Artwork and crown molding add detail around the perimeter of the room.
Home Theater
A home theater features wall-mounted speakers, ceiling acoustic treatments, and a projector system facing a large screen. Rows of plush seating, including sectionals and armchairs, are arranged on a soft carpet. The space is finished in deep tones with minimal lighting, designed for focused viewing. Multiple subwoofers are placed beneath the screen.
Bedroom
Vaulted ceilings with exposed wooden beams add scale to a bedroom with white walls and custom molding. A fireplace sits opposite a low platform bed, both centered on a large gray area rug. Matching nightstands and lamps flank the bed, and a gray bench rests at the foot. Natural light enters through multiple vertical windows.
Source: Ashlei De Souza @ Serhant Connecticut, LLC. via Coldwell Banker Realty
4. Greenwich, CT – $10,995,000
Located along the waterfront in Greenwich, this $10,995,000 estate spans 9,280 square feet and includes 6 bedrooms and 9 bathrooms (7 full, 2 half). Built in a Victorian style and set on nearly 1 acre, the property features a deep-water dock, an infinity pool, and a separate 2-bedroom guest cottage. Interior amenities include a new Italian kitchen with water views, a private gym, and a wine cellar.
Where is Greenwich?
Bordering New York and the coast, Greenwich, Connecticut, moves between quiet neighborhoods and a busy town center. It includes waterfront parks, shopping districts, and residential areas that reach into forested backcountry. The town has deep ties to finance, shipping, and regional history. Metro-North service connects Greenwich to New York City in under an hour.
Living Room
Sliding glass doors open the living room to a covered patio, blending indoor and outdoor seating areas. A fireplace anchors one end of the room, flanked by windows and tall plants in corner planters. Neutral-toned furniture surrounds a glass coffee table with a blue border, placed on a textured area rug. Recessed lighting and light wall colors keep the space bright.
Dining Room
Columned entryways connect the dining room to surrounding spaces, with glass doors leading out toward the water. A long wooden table with white modern chairs sits over a dark rug, under a linear pendant light. Potted plants and abstract wall art add visual interest around the perimeter. Multiple windows and glass panels frame water views.
Bedroom
Waterfront views dominate the bedroom through wide corner windows and a glass door that opens to a terrace. A window bench and animal print chair are positioned to face the scenery. The bed features a low-profile frame, flanked by two modern nightstands and matching lamps. Neutral tones and light fabric accents soften the room’s structure.
Bathroom
Cream-colored curtains frame tall windows in a spacious bathroom, allowing filtered natural light throughout. A marble-trimmed tub is set into a paneled surround near the center of the room. A curved double-sink vanity sits under an arched wall recess. Light hardwood floors extend across the room, contrasting the white cabinetry and trim. Small decorative pieces and wall art add subtle detail.
Waterfront Area
A large dock stretches from the backyard into the water, surrounded by lounge areas, dining space, and a grill setup on the wooden deck. A rectangular pool sits just above the lawn, bordered by stone and surrounded by greenery. A daybed with a canopy is placed at the pool’s edge, near a set of stepping stones leading through the garden. The property overlooks a small island, with additional docks nearby.
Source: Eva Penson @ Sotheby’S International Realty via Coldwell Banker Realty
3. Greenwich, CT – $19,500,000
Located in Greenwich, Connecticut, this $19,500,000 equestrian estate spans over 16 acres and includes three residential structures totaling 11 bedrooms and 13 bathrooms. The main residence, renovated in 2023, has 5 bedrooms and 7 bathrooms and is accompanied by a one-bedroom guest house/pool cabana and a separate French Country guest house with 5 bedrooms and 5 bathrooms.
Built by Drake Builders LLC and designed by Rich Granoff, the property includes horse stables for 12, a dressage arena, paddocks, and agricultural features such as vineyards, orchards, and gardens. Square footage for the structures is not specified, and the estate was originally built in an unspecified year.
Where is Greenwich?
Just an hour from Manhattan, Greenwich, Connecticut, stretches from wooded backcountry to the shores of Long Island Sound. The town includes several neighborhoods, a busy downtown, and a stretch of waterfront. Greenwich has a history tied to shipping, finance, and suburban growth. It offers beaches, parks, and train access to New York City.
Kitchen
Stone walls and wooden beams give the kitchen a lodge-like feel, with two large islands at the center topped with butcher block countertops. Copper pots and pans hang from racks suspended above the workspace, while more are stored on open shelving below. The cooking area features a copper range hood and a series of built-in appliances. Shelving units are stocked with deep purple dishware. Large stone tiles cover the floor throughout.
Dining Room
Two large chandeliers with purple accents hang over an extended dining table surrounded by fourteen upholstered chairs, some with embroidered crests. Floor-to-ceiling windows and glass doors wrap around the space, allowing natural light to pour in. Rustic wooden beams run across the ceiling, echoing the framing of the walls. Wall sconces and draped curtains add decorative detail. A fireplace with a stone surround anchors one end of the room.
Study
Built-in wood shelving lines the back wall of the study, filled with books and facing a traditional desk with carved legs and gold detailing. French doors open to a balcony, flanked by floor-to-ceiling wood paneling. A pair of computer monitors sits on a side desk beneath multiple windows. The ceiling features green patterned panels set between exposed wooden beams. A zebra-patterned rug lies across the light wood floor near the fireplace.
Bedroom
Whitewashed tree-trunk bedposts frame the bed in a bedroom that combines rustic wood with clean lines. One wall and the vaulted ceiling are clad in wood planks, while the others remain white. A pair of armchairs and a footstool sit near a bank of windows overlooking greenery. An oversized pendant light hangs from the peak of the ceiling. A sheepskin rug lies on the wide-plank floor.
Bathroom
Green and white veined stone forms a dramatic backdrop in the bathroom, stretching across the wall behind dual showerheads. A freestanding marble tub with brass fixtures is placed under a row of windows that frame views of a fenced field. The flooring and surrounding walls are done in matching pale marble. Built-in shelves hold rolled towels and decorative accents. A fur rug softens the look in front of the tub.
Source: Danielle Claroni and Leslie Mcelwreath @ Sotheby’S International Realty via Coldwell Banker Realty
2. Washington, CT – $19,900,000
With panoramic views of Lake Waramaug, this property includes 5 bedrooms, 8 bathrooms, and 10,203 square feet of living space, offered at $19,900,000. The home was designed by architect Steven F. Haas and featured in Architectural Digest in 2007.
It sits on approximately 18 acres with an additional 7-acre parcel included. The layout features a barrel-vaulted, glass-ceilinged walkway with high ceilings, limestone flooring, and mahogany-framed window walls. The estate also includes a pool, reflecting pool, formal gardens, and a guest house.
Where is Washington?
Washington, Connecticut, is a small town in Litchfield County known for its rural setting and preserved farmland. It includes several villages, with Washington Depot serving as the town center. The area features hiking trails, art institutions, and private schools. Washington has been a retreat for writers, artists, and visitors seeking quiet from nearby cities.
Living Room
Light filters through horizontal glass bands, casting striped shadows across stone floors in the main living room. Sofas in velvet and linen cluster around two coffee tables layered with books, plants, and ceramics. Framed by trees outside, the space feels folded into the landscape. Seating ranges from sculptural to traditional, with no piece overpowering the room’s rhythm.
Kitchen
Steel, tile, and wood come together in this kitchen, where open shelving and professional-grade appliances define the room’s purpose. A central island doubles as prep station and pot storage, with copper cookware stacked beneath. Sunlight pours through the oversized window behind the sink, blurring the edge between indoors and out. Everything is in reach, but nothing clutters.
Indoor Garden
Tropical foliage and sculptural baskets line the perimeter of the conservatory, where a round table and bentwood chairs sit at center. Skylights stretch across the ceiling, casting layered shadows like branches. Framed in wood and glass, the space acts as an indoor garden and informal dining room. Even the light seems alive here.
Bedroom
Soft curves and tall panes shape the bedroom into a space that opens fully to the hillside beyond. A tailored bed faces two club chairs by the window, with a carved clock acting as the room’s lone vertical anchor. Neutral textiles and light wood floors create calm without flattening it. Views wrap the room like wallpaper.
Bathroom
Concrete tub and floating vanity define the bathroom’s layout, with bamboo beams above echoing the vertical rhythm of trees outside. A wall of glass slides open to a small patio, letting light and air move through freely. Green tile forms a mosaic behind the mirror, catching each shift in daylight. Everything here is minimal but intentional.
Source: Peter Klemm @ Klemm Real Estate Inc via Coldwell Banker Realty
1. Greenwich, CT – $49,500,000
In Greenwich’s private Mead Point Association, this waterfront property spans 12,492 square feet with 6 bedrooms and 8 bathrooms and is offered for $49,500,000.
Built in 2014, the home sits on 1.6 acres and includes a private beach, dock, pool, outdoor kitchen, and fire pit. Interior features include a double-height living room, paneled library, reading room, formal and informal dining areas, chef’s kitchen, wine storage, exercise room, mudroom, and a three-car garage.
The primary suite has two dressing rooms, a private balcony, sauna, and soaking tub with water views. The property also includes a full house generator and access to the Mead Point Association’s community beach.
Where is Greenwich?
Greenwich, Connecticut, sits along the Long Island Sound and serves as a gateway between New York City and New England. The town includes coastal neighborhoods, inland parks, and a central business district with shops and restaurants. It has a long maritime history and a strong connection to finance through nearby Wall Street. Greenwich also offers museums, beaches, and access to commuter rail.
Living Room
Wood-paneled living room features arched glass doors that open to a waterfront view. Two blue leather chairs and a zigzag-patterned sofa form the central seating area around a curved wood coffee table. Sculptural lamps, bold pillows, and a textured rug fill the space. Wall-mounted television sits opposite the windows.
Kitchen
Cabinetry blends into the walls like built-ins from another time, while pendant lights and polished countertops cut clean lines across the space. Centered in the home, this kitchen draws its energy from symmetry and contrast—green seat cushions pop against white frames, and carved legs ground the marble island. Stainless steel appliances fold quietly into the corners. Movement flows without interruption.
Dining Room
Chandelier drops from a plaster medallion, floating over a wood table surrounded by green velvet chairs with brass legs. In this dining room, symmetry rules—from the oval window set opposite the glass doors to the balanced mirror and sideboard across the back wall. Pale rug and quiet walls let texture take over. Every detail holds still.
Office / Library
Books stand in measured rows, surrounded by bottle-green walls that lead to a pair of glass doors opening onto the sea. Centered in this office-library, two patterned armchairs face a game table set beneath a hanging lantern. Every shelf, frame, and object is part of the composition. Nothing is extra, but nothing is missed.
Bedroom
Ceiling slopes upward to a chandelier shaped like frost, while crisp white bedding and tailored edges frame the calm in this primary bedroom. Windows pull in coastline views from multiple angles, with a chaise stationed beneath one for quiet observation. A velvet bench and minimal side tables echo the room’s rhythm. Light plays across the walls like a tide.
Source: Leslie Mcelwreath @ Sotheby’S International Realty via Coldwell Banker Realty
