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Connecticut continues to dazzle with stately homes steeped in heritage, each uniquely adapted to modern luxury. Whether it’s a waterfront sanctuary in Stamford, a sun-drenched Colonial compound in Greenwich, or a historic Dutch home reimagined in Darien, these properties showcase the state’s deep architectural roots paired with fresh, high-end comforts.
With features like chef’s kitchens, restored barns, soaring atriums, and private pools, these estates reflect a lifestyle defined by elegance, character, and timeless design. Here’s a fresh collection of Connecticut’s most exquisite historic homes currently on the market.
In order to come up with the very specific design ideas, we create most designs with the assistance of state-of-the-art AI interior design software.
1. Colonial-Style Compound
Originally built in 1900 and expanded in the 1970s with a guest wing added in 2018, this 7,148 square foot Colonial-style residence offers seven bedrooms and eight bathrooms. Set on a landscaped one-acre lot in a prime location near downtown, the property includes multiple terraces, formal and casual living spaces, and a foyer with hardwood and marble flooring. Listed at $4,000,000, the home blends historic charm with modern updates and features a guest suite engineered for a potential two-story elevator.
Where is Greenwich, CT?
Greenwich is a town in Fairfield County, Connecticut, located on Long Island Sound and bordering Westchester County, New York. It includes several neighborhoods such as Cos Cob, Riverside, and Old Greenwich. The town is a financial hub with many hedge funds and investment firms based there. Greenwich has Metro-North rail service, public beaches, and parks, including the 147-acre Greenwich Point Park.
Living Room
Set beneath skylights, the main living area centers around a fireplace and wall-mounted TV. A white sectional, tufted ottoman, and armchairs define the space, with windowed doors opening to the patio. Pale finishes and layered seating make the space feel expansive.
Breakfast Nook
Tucked beside a tall arched window, the breakfast nook includes a round glass table and four striped armchairs. A cabinet and curtain panels fill the corners, echoing the traditional trim. Rail posts separate the space from the adjacent living room level.
Kitchen
Positioned at the center of the home, the kitchen features white cabinetry, glass-front uppers, and stainless steel appliances. A raised peninsula with four chrome stools divides the workspace from the adjoining rooms. Wide-plank dark flooring anchors the light-colored finishes throughout.
Bedroom
Arranged with symmetry, the bedroom places a king-size bed against a navy wall with triple windows at the foot. Patterned valances and matching lamps frame the room, while an armchair rests in the alcove. A striped rug and neutral floors complete the simple palette.
Patio Garden
Laid out with gravel and framed by manicured hedges, the garden patio offers multiple lounge areas beneath tree shade. Woven outdoor furniture surrounds a fire pit and side tables. Terraced steps connect this space to the rest of the backyard and house.
Listing agent: Patte Nusbaum of Sotheby’S International Realty, info provided by Coldwell Banker Realty
2. Restored Gem in New Canaan
Tucked into the vibrant center of New Canaan, this 1900-era residence was fully reimagined in 2011 to merge historic charm with modern elegance across 3,856 square feet. Featuring four bedrooms and five bathrooms, the home includes a chef’s kitchen, Sonos sound system, heated in-ground pool with cabana, and a garage designed for a car lift. Priced at $2,595,000, this property offers luxury living just steps from the town’s shops, restaurants, and amenities.
Where is New Canaan, CT?
New Canaan is a town in Fairfield County, Connecticut, situated near the New York state border. It is known for mid-century modern architecture and includes sites like Grace Farms and Waveny Park. The town center features boutique shops, restaurants, and a Metro-North station for commuting to New York City. New Canaan has a strong public school system and a suburban residential character.
Kitchen
Running along the back wall, the kitchen includes a stainless steel range with a full backsplash and matching hood. A white center island holds a table-height extension and integrated oven beneath. Floor-to-ceiling cabinets and a double-door refrigerator complete the built-in layout.
Dining Area
Centered in the home, the dining area features a rectangular wood table for eight set on a geometric-patterned rug. A double-sided marble fireplace divides the room and opens into the living space. Overhead lighting includes a modern chandelier and two wall sconces flanking a framed artwork.
Bedroom
Located under a vaulted ceiling, the bedroom includes a low platform bed flanked by nightstands and wall-mounted lamps. Storage drawers line both sides of the space under the windows. Natural light enters through a tall front-facing window and side casement units.
Bathroom
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Positioned along one side, the bathroom includes a wide vanity with dual sinks, marble counters, and mirrored wall. The walk-in shower is enclosed in glass and outfitted with body jets and a bench. Tiled floors feature a basket-weave pattern in white and gray.
Patio and Spa Area
Extending from the rear elevation, the outdoor space includes a raised stone hot tub next to a sunken seating area. Cushioned dining and lounge furniture are arranged under umbrellas. Lush plantings and trees form a green border for the stone terrace.
Listing agent: Melissa Rwambuya of William Raveis Real Estate, info provided by Coldwell Banker Realty
3. Renovated 1852 Residence
Set on 1.36 acres in Westport’s Old Hill neighborhood, this 1852-built home offers 3,658 square feet with four bedrooms and five bathrooms. Thoughtfully renovated, the property includes a custom kitchen with Miele and Viking appliances, multiple fireplaces, a sunroom, and vaulted living spaces, plus two heated/cooled outbuildings. Listed at $2,299,999, the grounds feature a stone patio, outdoor fireplace, pergola, and specimen plantings just minutes from town, schools, and Post Road.
Where is Westport, CT?
Westport is a coastal town in Fairfield County, Connecticut, located along Long Island Sound. It has a lively downtown, access to beaches like Compo Beach, and cultural venues such as the Westport Country Playhouse. The town is served by the Metro-North Railroad, connecting it to New York City. Westport is also known for its public schools and affluent residential neighborhoods.
Living Room
Tall arched windows line both walls of this living room, filling the space with natural light. Two white sofas and two matching armchairs form a square around a central coffee table beneath a rustic chandelier. Neutral colors and layered textures complement the white vaulted ceiling and hardwood flooring.
Kitchen
Rich wood cabinets and paneling define this open kitchen layout, which features a central island with a black stone countertop. A large white range stands out against the darker tones, while four sleek barstools provide seating. French doors and windows bring light into the kitchen and nearby dining nook.
Dining Space
Curved wooden chairs surround a round fluted pedestal table positioned in the center of a long sunroom. Floor-to-ceiling windows line both sides of the room with French doors opening into an adjoining area. A vaulted ceiling and hanging light fixture emphasize the symmetry of this open layout.
Home Office
Wall-to-wall shelving in deep wood tones provides storage and display space in this private office. A large window stretches across one side, offering a view of the garden outside. A white desk and armchair sit at the center, flanked by neutral-toned chairs and accessories.
Sunroom
Rattan lounge chairs, poufs, and a bar tray sit atop a tiled floor surrounded by tall windows. Views of trees and snow-covered ground are visible on all sides, creating a quiet, enclosed retreat. Multiple seating options define the space as casual and flexible for indoor-outdoor living.
Listing agent: Erica Acheychek of Coldwell Banker Realty
4. 1930s Dutch Colonial
On one of Darien’s most beloved in-town streets, this 1930 Dutch Colonial blends period elegance with modern updates across 3,417 square feet. Set on a full acre in a rare half-acre zone, the home features four bedrooms, four bathrooms, a new kitchen and baths, original hardwood floors, and detailed millwork. Listed at $2,950,000, the property includes a private pool and lush grounds with room to expand or add a guest cottage.
Where is Darien, CT?
Darien is a town in Fairfield County, Connecticut, located on the Long Island Sound between Norwalk and Stamford. It is primarily residential, with a compact downtown, two train stations on the Metro-North line, and access to beaches like Pear Tree Point and Weed Beach. The town has top-ranked public schools and several private clubs. Darien is also undergoing downtown redevelopment with new retail and housing projects.
Living Room
Framed by large windows, the living room offers a sitting arrangement with two armchairs, a couch, and a pair of side tables. The room centers around a glass coffee table set on a neutral-toned rug. A single colorful art piece hangs above the main sofa, providing contrast to the soft palette.
Kitchen
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Designed with clean lines, the kitchen includes a central island with turned legs, white cabinetry, and a stainless steel range and refrigerator. Pendant lights hang above the island where barstools provide extra seating. A bay window by the sink brings in natural light and views of the outdoors.
Dining Room
Surrounded by windows on two sides, the dining room is anchored by a long rectangular wood table with six carved chairs. A sideboard with a mirror and twin lamps lines one wall while built-in shelving accents the corner. Overhead, a three-light fixture adds symmetry above the centerpiece.
Family Room
Configured around a fireplace and mounted television, the family room contains a sectional sofa, two leather armchairs, and a large area rug. Recessed lighting and window symmetry add balance to the layout. Art above the couch and a fire lit in the hearth provide visual warmth.
Bedroom
Furnished with a neatly made bed, antique dressers, and an upholstered chair, the bedroom includes four windows that frame views of greenery. A sloped ceiling adds character to the room’s otherwise traditional structure. Soft textiles and light walls maintain an inviting atmosphere.
Listing agent: Amy Barsanti of William Pitt Sotheby’S Int’L, info provided by Coldwell Banker Realty
5. Waterfront Retreat
Perched on the edge of Long Island Sound, this 1925-built residence in Stamford’s Shippan Point offers nearly 4,000 square feet of sweeping waterfront living. With five bedrooms and four bathrooms, the home features a chef’s kitchen, gas fireplace, wraparound Ipe deck, and a private beach for kayaking. Listed at $3,200,000, it also includes a separate in-law apartment and panoramic water views from nearly every room.
Where is Stamford, CT?
Stamford is a city in Fairfield County, Connecticut, located on Long Island Sound and just north of the New York border. It has a major business district with corporate headquarters, especially in finance and media. Stamford includes neighborhoods like Harbor Point, Glenbrook, and Springdale, and is served by Amtrak and Metro-North rail. The city also features parks, a downtown arts scene, and waterfront attractions.
Living Room
Gathered around the television and glass coffee table, the living room features a sofa set framed by built-in cabinetry and shelving. Light wood floors run throughout, and the room opens up toward a waterside seating area visible in the background. Plants add color near each corner, flanking the transitional spaces.
Kitchen
Centered in the kitchen is a white island with a built-in wooden counter extension and four bistro-style stools. Cabinetry in white surrounds a commercial-style range with a decorative tile backsplash showing a sailing ship. Light floods the room through glass doors that open to a deck with a water view.
Dining Area
Framed by cabinetry and large windows, the dining space includes a white table paired with six cushioned chairs on a patterned rug. A chandelier hangs above the table, and sliding glass doors lead directly to the deck. Across the room, built-in cabinetry with glass doors includes a wet bar.
Bedroom
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Oriented toward a set of double closets, the primary bedroom includes a tufted headboard, lounge chairs, and a vanity. A large rug softens the wood floors, and multiple windows let in natural light. Walls are painted a soft blue-gray tone and are paired with white trim and light curtains.
Waterfront Deck
Positioned on a wood-plank deck, the outdoor seating area features woven lounge chairs and a circular fire pit table. A glass-railing edge lines the space, allowing uninterrupted views of the shoreline and neighboring buildings. Decorative pillows and a ceramic garden stool complete the setup.
Listing agent: Suzette Kraus of Compass Connecticut, LLC., info provided by Coldwell Banker Realty
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