Connecticut’s historic mansions are more than just homes—they’re a living showcase of the state’s architectural evolution and timeless elegance.
From turn-of-the-century chateaus and storybook Cotswold estates to restored colonials and 19th-century gems, each residence marries period detail with luxurious modern upgrades. These properties reflect a refined lifestyle, offering features like chef’s kitchens, grand fireplaces, sunrooms, and private grounds—all within charming towns known for their culture, beaches, and commuter convenience.
Here’s a curated look at some of the most distinctive historic estates currently on the market in Connecticut.
1. 1887 Drum Road Residence
This 4,576 square foot home in Rowayton was originally built in 1887 and features six bedrooms and four bathrooms. Set on a 0.36-acre lot, the property retains original architectural details like moldings while offering modern updates across three levels, including a library, multiple flexible spaces, and a finished garage. Listed at $3,995,000, it sits near the town center with proximity to local dining and Bayley Beach.
Where is Norwalk, CT?
Norwalk is a coastal city located in Fairfield County, Connecticut, along the northern shore of Long Island Sound. It is part of the New York metropolitan area and is served by the Metro-North Railroad. Norwalk is home to the Maritime Aquarium and the historic Lockwood-Mathews Mansion Museum. The city also includes several neighborhoods such as South Norwalk (SoNo), which features a vibrant dining and arts scene.
Living Room
Framed by five tall windows, the living room features a central cream-colored sofa, flanked by woven wood-frame chairs and a red armchair. A dark rectangular coffee table anchors the seating arrangement on a pale rug, with books and flowers adding a lived-in touch. Centered artwork and surrounding paintings lend geometric and landscape themes to the white-walled space.
Kitchen
Spread across three walls and centered by a large island, the kitchen uses pale green cabinetry and wood floors to create warmth. The island includes two stools, built-in shelves, and a vase of flowers, while open shelving and glass-front cabinets offer accessible storage. A large refrigerator and dual sinks frame the room’s functional layout.
Dining Room
Positioned between two large windows, the dining room centers around a long black rectangular table surrounded by eight woven-back chairs. A fireplace with a carved wood mantle sits on one end, and built-in cabinetry with glass doors offers functional charm. A modern chandelier and a pair of abstract artworks complete the room’s balanced style.
Bedroom
Under a vaulted wooden ceiling, the primary bedroom holds a wide bed between two symmetrical windows and matching bedside tables. A fireplace with a black mantle sits to one side, opposite a reading chair and small seating area. A pendant light fixture hangs centrally above, drawing attention to the room’s pitched roofline.
Bathroom
Surrounded by white tile walls with soft blue accents, the bathroom features a freestanding clawfoot bathtub placed below two windows. A wood-paneled ceiling mirrors the bedroom’s and includes a small triangular window above. A wicker stool, chrome fixtures, and subtle built-in heating complete the light-filled bath space.
Listing agents: Elizabeth Beinfield, Jenny Friedman of Compass Connecticut, LLC., info provided by Coldwell Banker Realty
2. Stone and Clapboard Colonial in Chestnut Hill
Built in 1930, this 4,751 square foot stone and clapboard colonial in southeast Wilton offers five bedrooms and six bathrooms on a spacious property designed by architect Frazier Peters. The home features a garage apartment with its own bed and bath, dual laundry areas, and a finished basement with a fireplace-equipped playroom. Priced at $2,050,000, the residence includes a heated pool, spa, cabana with full bath, and a three-car garage.
Where is Wilton, CT?
Wilton is a town in Fairfield County, Connecticut, located in the southwestern part of the state. It is known for its residential character, wooded areas, and access to the Metro-North Railroad via the Danbury Branch. Wilton includes several historic landmarks such as the Cannondale Historic District and Weir Farm National Historical Park. The town is governed by a Board of Selectmen and has a strong public school system.
Dining Room
Furnished with a dark oval table and eight wood chairs, the formal dining room features blue patterned seat cushions and botanical prints above a sideboard. A lantern-style ceiling fixture centers the space, framed by neutral walls and wood flooring. A wide doorway leads into another part of the home, providing a sense of openness.
Family Room
Focal to the family room is a fireplace with a marble surround and wall-mounted TV above, flanked by white built-in shelving. Two patterned armchairs and a brown sectional form a seating area around a round navy ottoman. The room opens into the dining area and is accented by wood floors, white trim, and a beam-accented ceiling.
Sunroom and Office
Split between two spaces, the sunroom and adjacent office offer separate functions in a shared open layout. Large arched windows define the sunroom, furnished with transparent chairs, a loveseat, and a floral rug. Just past the wide doorway, the office features a long white desk with pink stools and dual windows over hardwood floors.
Bedroom
Tucked under a sloped ceiling, the bedroom includes a king-size bed, two closets, and a window bench centered between dormer windows. A large light rug spreads across the wood floor beneath a soft overhead light. A tall dresser, TV, and side tables complete the layout, blending traditional elements with cottage-like details.
Backyard and Pool Area
Seen from above, the backyard includes a rectangular in-ground pool with a built-in hot tub and surrounding stone patio lined with lounge chairs. A wide lawn extends beyond the pool, featuring a children’s playset and bordered by tall trees and shrubs. The house connects to the outdoor space through several entrances, with a driveway and garage set to one side.
Listing agent: Marion Filley of Compass Connecticut, LLC., info provided by Coldwell Banker Realty
3. Elegant 1928 Cotswold Estate
Tucked behind lush landscaping on a rare double lot, this 6,469 square foot English Cotswold-style residence in Riverside offers six bedrooms and seven bathrooms. Built in 1928, the home features a 2020-renovated chef’s kitchen, a vaulted family room with a bar, and a spacious playroom, all blending historic charm with modern luxury. Priced at $5,250,000, it provides proximity to parks, schools, the village, and train access.
Where is Riverside, CT?
Riverside is a neighborhood in Greenwich, Connecticut, located in Fairfield County along the Long Island Sound. It is primarily residential and known for its access to the Riverside and Cos Cob train stations on the Metro-North line. The area includes Riverside School and Eastern Middle School, serving the local community. Riverside also features several parks and is bordered by Old Greenwich and central Greenwich.
Living Room
Set around a white fireplace with glass doors, the living room includes two long sofas, two matching armchairs, and a pair of sculptural coffee tables. A muted rug and light blue walls provide a neutral palette, with soft accent pillows and a single abstract painting adding subtle variation. Double French doors open to the outside, while an arched built-in shelf adds a small architectural detail.
Kitchen
Running along one wall and anchored by a large island, the kitchen features all-white cabinetry, stainless appliances, and marble-style backsplash and countertops. A trio of white stools lines the breakfast bar, while recessed lighting brightens the space. Toward the back, a vaulted ceiling rises over a breakfast nook framed by tall windows and a modern pendant light.
Dining Room
Lit by a central chandelier, the dining room features a long glass-top table with eight curved upholstered chairs on a patterned area rug. French doors line both sides of the room, opening to an outdoor patio and bringing in sunlight. Warm beige walls and clean white trim keep the setting formal yet accessible.
Bedroom
Organized around a king-size bed with white linens and matching side tables, the bedroom includes neutral walls, a large window with tailored curtains, and recessed lighting. A light rug covers the wood flooring, and a cushioned bench rests at the foot of the bed. To one side, a small hallway leads to additional rooms or a closet space.
Patio
Framed by hedges and flowering trees, the patio includes a wicker outdoor lounge set with beige cushions arranged around a central coffee table. Another dining set is positioned nearby, suggesting space for both relaxation and meals. Large doors connect the house directly to the stone-paved courtyard, surrounded by shaped greenery and a retaining wall.
Listing agent: Lindsay Sheehy of Compass Connecticut, LLC., info provided by Coldwell Banker Realty
4. Updated 1900 Colonial
Blending early 20th-century charm with modern updates, this 3,270 square foot colonial in Westport’s Compo South neighborhood features four bedrooms and four bathrooms. Originally built in 1900 and set on a 0.79-acre lot, the home includes a renovated kitchen, updated baths, dual staircases, and a finished lower level. Priced at $2,300,000, it offers a peaceful cul-de-sac setting just minutes from downtown, the train station, Longshore Club Park, and Compo Beach.
Where is Westport, CT?
Westport is a coastal town in Fairfield County, Connecticut, situated along Long Island Sound. It has a commuter-friendly location with a Metro-North station and is known for its strong arts scene, including the Westport Country Playhouse. The town features popular destinations like Compo Beach and the downtown shopping district. Westport also has a public school system and a mix of suburban and waterfront neighborhoods.
Lounge
Arranged around a black fireplace with a white painted brick surround, the sitting room features a sofa, two armchairs, and a glass coffee table. Wall art and neutral window treatments enhance the space, and hardwood flooring ties the room together. An open hallway leads into additional areas of the home, visible just beyond the seating area.
Kitchen
Outfitted with gray shaker cabinets and stainless steel appliances, the kitchen centers around a wide island with white quartz countertops and four white barstools. A set of pendant lights hangs above the sink, while a tile backsplash lines the wall behind the stove and range hood. Double ovens and a large refrigerator complete the galley layout, blending form and function.
Dining Area
Combining dining and living in one open layout, the shared area includes a wood dining table with six light gray chairs on a blue rug. Toward the back, the living space holds armchairs and a sofa arranged around a white fireplace beneath framed artwork. Natural light from multiple windows and recessed lighting overhead brightens both zones equally.
Sunroom
Styled with wicker seating and blue cushions, the sunroom runs the length of the side of the house beneath a paneled white ceiling. Striped blue and white carpeting stretches wall to wall, while potted plants and small tables finish the relaxed setting. A wood dining table anchors the far end, surrounded by large windows looking out to the yard.
Bedroom
Divided into sleeping and lounge areas, the primary bedroom includes a bed with neutral bedding, a curved settee, and a TV setup across the room. Two windows and light wall tones keep the room bright, and a modern chandelier hangs from a white-beamed ceiling. A doorway leads directly into an en suite bath, partially visible near the dresser.
Listing agent: Judy Michaelis of Coldwell Banker Realty
5. Turn-of-the-Century French Chateau
Built in 1906 by banker Albert Wiggin, this 6,781 square foot French Chateau-style estate in Ridgefield offers six bedrooms and eight bathrooms on a 2.14-acre lot. Known as Peaceable Acres, the home has been restored to preserve original details and includes features such as a chef’s kitchen with double islands, a wood-paneled study, multiple fireplaces, and a curved staircase leading to a luxurious primary suite. Listed at $3,275,000, the property also includes a veranda, stone terraces, and a separate cottage, all within walking distance to the town center.
Where is Ridgefield, CT?
Ridgefield is a town in Fairfield County, Connecticut, located in the foothills of the Berkshire Mountains near the New York state line. It has a well-preserved Main Street with historic buildings, shops, and the Ridgefield Playhouse. The town is known for its school system and residential character, with access to nearby Metro-North stations in Branchville and Katonah, NY. Ridgefield also includes natural attractions like Bennett’s Pond and the Aldrich Contemporary Art Museum.
Kitchen
Fitted with sky-blue cabinets and double islands, the kitchen includes pendant lighting, white countertops, and wood flooring throughout. A long island with curved corners offers seating for six on striped stools, while the stove wall features open shelving, a pot filler, and white subway tile backsplash. Diamond-patterned windows over the sink and a wide fridge along the side wall round out the layout.
Dining Room
Surrounded by navy blue walls and white wainscoting, the dining room includes a long wooden table with ten white slipcovered chairs on a pale rug. A woven pendant light hangs from the coffered ceiling, adding texture above the center of the room. Two tall plants frame the space, and doorways open into adjacent rooms.
Sunroom
Wrapped in large windows, the sunroom includes a TV wall, wicker-framed seating, a central rug with blue and white chevrons, and a small table set near the far door. Pillows, poufs, and side tables add comfort and utility to the long space. Beige tile flooring and white beadboard walls keep the palette light and coastal.
Bedroom
Defined by its spacious layout, the primary bedroom centers a king bed with a bench, two nightstands, and a tall dresser across from a full-length mirror. Blue walls and light curtains frame the tall windows, with wood flooring and a soft rug covering most of the room. A fireplace peeks into the side of the frame, opposite built-in closets and doors.
Bathroom
Divided between soaking and shower zones, the bathroom features a freestanding tub by the windows and a glass-enclosed shower with white marble-style tile. A wide dual-sink vanity includes storage and two mirrors under modern lighting. White beadboard paneling and medium-tone floors give it a clean, simple finish.
Listing agents: Kenny Rhodes, Jeff Turner of eXp Realty, info provided by Coldwell Banker Realty
