Connecticut’s real estate scene is a refined blend of coastal splendor, wooded privacy, and architectural prestige. From the classic estates of Greenwich to the artistic enclaves of Litchfield County, the state offers elegant living with proximity to both natural beauty and metropolitan life.
Here are some of the most expensive homes in Connecticut, where grandeur meets timeless East Coast charm.
5. Washington, CT – $14,000,000
Set on 18 acres overlooking Lake Waramaug, this $14,000,000 modernist villa spans 10,203 square feet with 5 bedrooms and 8 bathrooms, built in 2003. Designed by architect Steven F. Haas with landscape by Renny Reynolds, the estate features limestone and mahogany finishes, floor-to-ceiling window walls, and a glass-ceilinged walkway. The property includes a guest house, formal and vegetable gardens, a pool, and a reflecting pool, with a separate 7-acre parcel included.
Where is Washington?
Washington is a rural town in Litchfield County, Connecticut, located in the northwestern part of the state. It is known for its scenic countryside, private schools like The Gunnery, and a tradition of land conservation. The town includes several villages, including Washington Depot, which inspired the setting for the TV show Gilmore Girls. Washington is part of the Housatonic Valley region and has a strong arts and literary community.
Living Room
Wrapped in floor-to-ceiling windows and exposed beams, the living room frames tree-lined views with low-profile sofas and rustic tables. An earthy color palette dominates the walls and furniture. Oriental rugs and sculptural decor pieces anchor the seating areas.
Dining Room
Positioned between open walls and sliding glass doors, the dining room features a long table with mismatched chairs. Natural light pours in from all sides and leads out to a terrace. Warm-toned walls and clean lines balance rustic and contemporary details.
Kitchen
Centered around a mosaic-tiled island, the kitchen combines commercial-grade stainless-steel appliances with wood cabinetry. Open shelving and large windows support function and light. Compact layout keeps tools, pans, and prep areas close at hand.
Bedroom
Encased in full-height windows with wooden framing, the bedroom captures expansive landscape views. A neutral palette spans the bed, sofa, and soft rug. Lounge chairs and sculptural accents complete the tranquil corner.
Bathroom
Framed by bamboo lighting and large windows, the bathroom includes a concrete soaking tub and extended double vanity. Wall textures range from polished to organic. Access to a private outdoor patio sits directly across from the tub.
Listing agent: Peter Klemm of Klemm Real Estate Inc, info provided by Coldwell Banker Realty
4. Fairfield, CT – $15,000,000
Enclosed within nearly 39 acres in Greenfield Hill, this $15,000,000 estate spans 9,129 square feet with 7 bedrooms and 10 bathrooms, originally built in 1965. Once home to composer Richard Rodgers, the mid-century residence has been extensively restored and features a pool, pool house with gym, heated paddle tennis court, and separate gatehouse. Surrounded by a 155-acre nature preserve, the property includes a theater, Moroccan lounge, and two-story office pavilion, offering potential for equestrian use and private living close to Fairfield and Westport.
Where is Fairfield?
Fairfield is a town in Fairfield County, Connecticut, located on the Long Island Sound between Bridgeport and Westport. It is home to several beaches, universities like Fairfield University and Sacred Heart University, and a mix of residential neighborhoods. The town has a historic town green and a growing downtown area. Fairfield is served by multiple Metro-North stations, linking it to New York City.
Dining Room
Lined with glass doors on one side and a mural wall on the other, the dining room features a long wooden table surrounded by upholstered chairs in mixed fabrics. A glossy black ceiling reflects contemporary lighting. Large panels open to a stone patio and lawn.
Kitchen
Organized around a central island and stainless-steel range, the kitchen is finished with dark wood cabinetry and matte countertops. Sliding doors lead into a study with shelves and a bright green chair. Open sightlines connect to a seating area with a large photograph.
Study
Divided by black-framed bookshelves, the study room includes a lounge sofa, writing desk, and patterned rug. Floor-to-ceiling shelving surrounds a view into the bedroom. Wallpaper and a mosaic ceiling add texture and contrast throughout the room.
Bedroom
Framed by vaulted ceilings, the bedroom holds a tall blue bed flanked by twin nightstands and two accent chairs by the fireplace. A statement light fixture hangs overhead. Curtains and framed artwork complete the room’s tailored style.
Bathroom
Decorated with patterned wallpaper and tile, the bathroom includes a freestanding tub facing garden views through sliding glass doors. A mounted TV and dual towel bars line the wall. Monochrome graphics appear throughout the space from floor to ceiling.
Listing agents: Leslie Razook, Cyd Hamer of William Pitt Sotheby’S Int’L, info provided by Coldwell Banker Realty
3. Westport, CT – $25,000,000
On 6.6 acres along Beachside Avenue, this $25,000,000 estate features 11,450 square feet of living space with 5 bedrooms and 6 bathrooms, built in 2007. Designed by Roger Ferris, the home includes 400 feet of direct Long Island Sound frontage, a tennis pavilion, multiple garage bays, and expansive south-facing patios for indoor-outdoor living. Highlights include a modern primary suite, guest wing with private entry, geothermal heating, and a full basement with catering prep room and utility areas.
Where is Westport?
Westport is a town in Fairfield County, Connecticut, located along Long Island Sound. It has a vibrant downtown, public beaches, and a strong arts scene. The town is a commuter community within the New York metropolitan area, served by Metro-North Railroad. Westport is also known for its public schools and historic districts.
Living and Dining Area
Anchored by a light brick fireplace, the living and dining area includes a white sofa, plush armchairs, and a round dining table near arched windows. Pendant lights hang above both seating zones. Glass doors open to a waterfront lawn and ocean view.
Lounge Room
Flanked by open bookshelves, the lounge room holds two blue sofas, two white chairs, and a central white coffee table. Shelves contain ceramics, framed art, and books arranged by height. A woven jute rug grounds the seating over dark-stained flooring.
Kitchen
Laid out with an oversized island, the kitchen uses stone countertops, white cabinetry, and a massive stainless steel range hood. Four woven stools line the breakfast bar. Warm wood flooring continues into the connected living space.
Bedroom
Outlined with a wood-paneled ceiling, the bedroom faces the water through wide bay windows. A king bed sits beside two upholstered chairs and a low round ottoman. Neutral tones dominate the space with whitewashed walls and soft carpet underfoot.
Aerial View
Shaped in a bent L-formation, the home features multiple roof angles, a central courtyard, and surrounding formal gardens. A long driveway curves through manicured lawns leading to the main entrance. Paths and hedges frame outdoor seating and planted sections.
Listing agent: Leslie Clarke of Compass Connecticut, LLC., info provided by Coldwell Banker Realty
2. Darien, CT – $29,500,000
On Darien’s coast, this $29,500,000 estate spans 8,684 square feet with 6 bedrooms and 8 bathrooms, built in 2010 on Hay Island. The 18.15-acre private island includes a main house, two-bedroom guest house, pool house, dock, infinity-edge pool, and two sandy beaches. Designed by Austin Patterson Disston, the home features six fireplaces, panoramic Long Island Sound views, and extensive outdoor living spaces including terraces, spa, and screened porches.
Where is Darien?
Darien is a coastal town in Fairfield County, Connecticut, situated along Long Island Sound between Stamford and Norwalk. It is primarily residential and part of the New York City metropolitan area. The town features parks, beaches, and a walkable downtown area. Darien is served by Metro-North Railroad, making it a commuter hub.
Lounge
Positioned between columns and large windows, the sitting room features a pair of patterned armchairs, a rolled-arm loveseat, and a tufted ottoman. Drapes are pulled back to reveal the ocean view. Throw pillows in red and cream accent the muted upholstery.
Library
Wrapped in built-in wooden bookshelves, the library includes two armchairs, a matching ottoman, and a long upholstered sofa. Book spines in varied colors line the shelves from floor to ceiling. A patterned rug anchors the furniture facing the windows.
Kitchen
Designed in a galley layout, the kitchen features light stone counters, green and beige cabinetry, and a dark metal hood above the stove. A lantern-style pendant light hangs over the central island. Wood ceiling beams and a framed vintage poster add visual texture.
Dining Room
Set near tall waterfront windows, the dining room holds a polished wood table surrounded by eight high-back chairs. A crystal chandelier hangs above, and a pale floral rug spans the floor. Decorative columns frame the open passage into the adjacent parlor.
Pool Area
Enclosed by a low stone wall and wooden deck, the rectangular pool sits at the edge of the manicured lawn. Lounge chairs and umbrellas line one side, while steps lead down from the house above. Trees and waterfront views complete the background.
Listing agent: Leslie Mcelwreath of Sotheby’S International Realty, info provided by Coldwell Banker Realty
1. Greenwich, CT – $34,500,000
In Greenwich’s backcountry, this $34,500,000 estate spans 15,820 square feet with 10 bedrooms and 16 bathrooms, originally built in 1937. Set on a high point, the compound includes two cottages, stables, paddocks, indoor and outdoor pools, a tennis house, and tennis court. The grounds, designed by Parisian landscape architect Jacqueline Osty, complement the restored main house by Augusta L. Noel, creating an expansive, multi-residence property.
Where is Greenwich?
Greenwich is a town in Fairfield County, Connecticut, located on the southwestern tip of the state along Long Island Sound. It is part of the New York metropolitan area and known for its financial services sector. The town features historic districts, beaches, and upscale residential neighborhoods. Greenwich also hosts corporate headquarters and cultural institutions like the Bruce Museum.
Entry Hall
Framed by a curved staircase, the entry hall features white marble floors with inset stone detailing and a seating area by the large front window. A sculptural table and decorative vases anchor the center. The stair railings and trim contrast in deep wood tones against light neutral walls.
Living Room
Placed under a grid ceiling with golden lines, the living room includes multiple lounge arrangements, pastel chandeliers, and walls of tall windows and draped glass doors. A staircase in the back corner leads to an adjacent indoor pool. Bold wallpaper and layered furniture create a formal reception space.
Office
Surrounded by ornate gold trim, the office includes glass-front cabinets that wrap around the entire room. A small writing desk sits centered between two white textured chairs. Molded ceiling panels and detailed wall insets follow a symmetrical layout.
Dining Room
Ornate chandeliers hang over a large oval table in the dining room, where tall ceilings and crown moldings frame soft cream-colored walls. A mirrored buffet and gold-framed mirror occupy one side opposite a fireplace. Floral arrangements and candleholders complete the table setting.
Aerial View
Spanning several acres, the estate includes a main residence, guest structures, a pool, tennis court, greenhouse, and riding arena. Winding driveways, manicured lawns, and paddock fencing divide the land. Trees line the perimeter while open fields stretch between buildings.
Listing agent: Shelly Tretter Lynch of Compass Connecticut, LLC., info provided by Coldwell Banker Realty
