Connecticut’s shoreline and countryside continue to unveil their most enchanting secrets through timeless estates that have been beautifully updated for modern living. From an island escape in the Thimble Islands to a grand Greenfield Hill Colonial, these historic homes offer stories etched in wood, stone, and sea breeze. Each property seamlessly integrates heritage architecture with contemporary luxury—whether through solar panels, chef’s kitchens, or spa-like suites—while nestled in some of the state’s most coveted enclaves.
Below is a curated selection of Connecticut’s historic mansions that prove legacy and lifestyle can truly go hand in hand.
1. 1912 Island Cottage
Set on 1.04 acres on Beldens Island in the Thimble Islands, this 2,038 square foot 1912 cottage offers 4 bedrooms and 2 bathrooms with sweeping views of Long Island Sound.
Offered fully furnished at $2,750,000, the property includes a private dock, sandy beach, two deeded acres of adjacent shellfish beds, and modern upgrades such as solar, a new seawall, and irrigation system. Surrounded by pink granite walls and lush lawns, the vintage cottage features hardwood floors, a stone fireplace, and a country kitchen with butler’s pantry.
Where is Branford, CT?
Branford is a coastal town in New Haven County, Connecticut, located along Long Island Sound just east of New Haven. It features a scenic harbor, over 20 miles of shoreline, and the Thimble Islands, a group of small islands popular for boating. The town includes distinct neighborhoods such as Stony Creek, Short Beach, and Pine Orchard. Branford has a mix of residential, commercial, and historic areas, with roots dating back to its incorporation in 1685.
Living Room
Living room is lined in wood paneling and anchored by a wide stone fireplace between two windows. Patterned slipcovered sofas face a central glass coffee table with a nautical model nearby. Wall art and wood flooring enhance the rustic cabin style.
Dining Room
The dining room sits beside corner windows, framing water views through wood trim. A long wooden table with ten chairs stands in the middle of the room under a small light fixture. Matching wood paneling and floors carry over from the adjacent rooms.
Kitchen
Wood-clad kitchen features a central island with thick countertops and hanging pots above. Cabinets with glass fronts line the upper wall while the tiled stove area adds a distinct accent. A deep white sink stretches across the windowed wall under vintage fixtures.
Bedroom
Bedroom on the upper level features sloped wooden ceilings and a view through several windows. A white metal bed frame is paired with blue bedding and a coastal artwork above the headboard. Light from the side windows illuminates hardwood floors and a dresser.
Aerial View
A small private island hosts a coastal home, surrounded by calm blue waters and connected by a narrow wooden dock. Grass covers most of the landscape, bordered by rocky edges and a stone retaining wall. Two blue Adirondack chairs face the open water from the lawn.
Listing agent: Kiara Rusconi of William Raveis Real Estate, info provided by Coldwell Banker Realty
2. 1744 Farmhouse
Built in 1744 with a 1992 addition by architect Bruce Beinfield, this 3,336 square foot farmhouse in Norwalk’s Wilson Point enclave offers 4 bedrooms and 4 bathrooms. Set on a landscaped acre with a heated gunite pool, spa, and rebuilt screened-in porch, the home blends historic charm with modern upgrades including a vaulted family room, updated kitchen, and private guest suite.
Priced at $2,349,000, it includes access to Long Island Sound, private beach, dock, clubhouse, and tennis courts in a coveted gated waterfront community.
Where is Norwalk, CT?
Norwalk is a city in Fairfield County, Connecticut, located along Long Island Sound between Stamford and Bridgeport. It has a historic seaport, a revitalized downtown area called SoNo (South Norwalk), and attractions like The Maritime Aquarium and the Sheffield Island Lighthouse. Norwalk is served by multiple Metro-North stations and is a major stop along I-95 and the Merritt Parkway. The city is known for its oyster industry and hosts the annual Norwalk Oyster Festival.
Living Room
Double-height ceilings define this living room, where a white entertainment center and TV wall face off with two gray armchairs and a soft-toned sofa. Railings from the upper level balcony surround the room, and a central chandelier ties the space together. The staircase leads up on both sides, connecting the main floor with rooms above.
Dining Room
Wood ceiling beams painted white stretch across this dining room filled with natural light from multiple windows. A long wooden table anchors the space, paired with six upholstered chairs and an oversized rug. A glass-panel door leads to an adjoining area, while warm wall tones contrast with crisp white trim.
Kitchen
Long counters wrap around the perimeter of this white kitchen, with marble surfaces and ample cabinetry. Centered under a small window, the sink sits between two corner units with glass-fronted cupboards above. A wide island extends toward the adjacent room, featuring display shelving and seating.
Bedroom
Tall ceilings and oversized windows define this bedroom, where the bed is placed diagonally across from a daybed near a narrow strip of clerestory windows. A TV sits flush in a recessed nook beside a full-height window that looks out to the backyard. Hardwood floors and soft beige walls warm up the airy interior.
Pool Area
Paved stone surrounds the in-ground pool out back, bordered by a white picket fence and lounge chairs. Trees rise behind the perimeter for privacy, with a patio dining set set up to one side. A built-in hot tub is positioned close to the house, integrated into the corner of the pool.
Listing agent: Kathleen O’Connell of Coldwell Banker Realty, info provided by Coldwell Banker Realty
3. 1872 Retreat
Perched on Seminary Street, this 2,300 square foot home blends 1872 charm with a full-scale renovation, offering 3 bedrooms and 4 bathrooms on a beautifully landscaped in-town lot. Inside, 8-inch wide plank floors, arched 9-foot ceilings, and a Carrara marble kitchen lead to a cozy breakfast room with soapstone floors, while the lower level adds a flexible suite with bath, mudroom, and laundry.
Priced at $2,295,000, the property includes a bucolic backyard barn and is steps from downtown shops, dining, parks, and the train.
Where is New Canaan, CT?
New Canaan is a town in Fairfield County, Connecticut, located about 48 miles northeast of New York City. It’s known for its mid-century modern architecture, especially in the “Harvard Five” homes, and for the expansive Waveny Park. The downtown area features upscale shops, restaurants, and a train station on the Metro-North New Haven Line. Incorporated in 1801, New Canaan remains a residential community with strong schools and preserved open space.
Living Room
Sunlight streams in through tall corner windows, casting soft shadows across the white walls and wood flooring. In this part of the house, a pale sofa and a pair of plaid armchairs center around a textured ottoman set atop a patterned rug. Minimalist furniture and wall art keep the space open and airy while preserving a relaxed mood.
Dining Room
Natural light defines the dining area, where a rustic wood table anchors the space between two tall windows. In this part of the house, woven chairs and a linear pendant add visual balance to the vertical window frames. The soft tones of the floor and walls keep the atmosphere quiet and understated.
Kitchen
Matte white cabinetry lines the kitchen where shaker doors and open shelving create symmetry along the perimeter. In this part of the house, a central island with barstools allows for casual dining under a ceiling with detailed molding. Black and gold fixtures break the monochrome palette with subtle contrast.
Bedroom
Pitched ceilings and a bay window draw attention upward in this second-floor bedroom. In this part of the house, the pink upholstered bed sits opposite a built-in bench that faces multiple windows overlooking the trees. White walls and minimal furnishings keep the room feeling crisp and open.
Listing agent: Marsha Charles of Coldwell Banker Realty
4. 1921 Colonial
Built in 1921 and fully renovated, this 3,919 square foot Nantucket-style Colonial in Darien’s Tokeneke Association offers 5 bedrooms and 5 bathrooms. Elevated on a scenic lot overlooking Scott’s Cove Estuary, the home features a wraparound deck, high ceilings, a custom wet bar, and a third-floor guest suite with office and gym.
Listed at $4,395,000, the property includes a newly built two-car garage and combines historic charm with modern function in a prime coastal setting.
Where is Darien, CT?
Darien is a town in Fairfield County, Connecticut, situated along Long Island Sound between Stamford and Norwalk. It is primarily residential, with two public beaches, a small downtown, and access to the Metro-North New Haven Line. The town has a high-ranking public school system and a variety of parks and community facilities. Incorporated in 1820, Darien also features Noroton and Tokeneke as notable neighborhoods.
Living Room
Windows line the back wall of this living room, filling the space with natural light and framing a cozy arrangement of navy and patterned seating. A glass coffee table sits at the center, placed over a neutral woven rug. The space opens into another sunroom through wide French doors.
Kitchen
Glass-front cabinets and white shaker drawers fill this kitchen, organized around a modern glass island table. The countertops are dark with light backsplash tiling for contrast, and a window over the sink faces green outdoor views. An induction cooktop and range hood are built into the cabinetry along the far wall.
Dining Room
Two full walls of windows brighten this dining room, which features a long wooden table paired with a mix of chairs in blue, white, and clear acrylic. Navy blue trim highlights the windows and contrasts with the white walls and curtains. A pendant chandelier hangs above the table for overhead lighting.
Bedroom
Angled walls and high ceilings define this spacious bedroom, with a fireplace placed across from the bed. A writing desk and two built-in window seats complete the layout, along with dark wood floors and soft blue walls. The room is organized around a large patterned rug beneath the bed.
Deck
An expansive deck serves as the outdoor living space, bordered by white railings and surrounded by mature trees. One side hosts a long outdoor sectional with a square coffee table, while the other includes a large dining table with multiple chairs. The layout offers views of the surrounding neighborhood and greenery.
Listing agent: Ashley Dineen of Compass Connecticut, LLC., info provided by Coldwell Banker Realty
5. 1840 Colonial Estate in Greenfield Hill
Blending nearly two centuries of history with refined modern living, this 8,004 square foot estate in Fairfield’s Greenfield Hill features 5 bedrooms and 6 bathrooms on 3 landscaped acres.
Originally built in 1840 and expanded by noted architects Cameron Clark and Jim Thompson, it offers a new primary suite with gym and office, a light-filled great room, and a detached guest house with lofted studio space. Listed at $4,995,000, this architectural gem sits just off the town green, offering timeless style and exceptional privacy.
Where is Fairfield, CT?
Fairfield is a coastal town in Fairfield County, Connecticut, located between Bridgeport and Westport along Long Island Sound. It is home to several beaches, Fairfield University, and Sacred Heart University. The town includes neighborhoods like Southport and Greenfield Hill and offers a mix of suburban living and historic charm. Fairfield was settled in 1639 and is served by multiple Metro-North stations, making it a commuter hub.
Dining Room
An oval wood table with eight patterned chairs sits in the center of the dining room beneath a traditional chandelier. French doors span the back wall, opening to outdoor spaces and bringing in natural light. A sideboard and detailed crown molding complete the setting.
Family Room
A white sectional and cream sofas create a conversation area centered on a glass coffee table over a patterned rug. Built-in shelving with cabinetry and display space lines the back wall, holding books and decor. Light flows in from nearby windows, and colorful artwork adds personality throughout the room.
Bedroom
A king-size bed with white linens anchors the bedroom, flanked by mirrored nightstands and elegant table lamps. A crystal chandelier hangs from the vaulted ceiling, and a fireplace sits beneath a mounted TV across from the bed. The room connects directly to a bright en-suite bathroom through an open doorway.
Bathroom
Dual vanities run the length of the wall beneath a row of large windows, with a soaking tub between them. On the opposite side, a spacious glass-enclosed shower features multiple fixtures and bench seating. Soft white finishes and natural light fill the room, creating an open and calming atmosphere.
Pool Area
Lounge chairs sit along the pool deck with a pergola structure offering shaded seating directly behind them. The rectangular pool features shallow entry steps at one end and is bordered by lush grass and manicured landscaping. Two trees and a wooden fence frame the backyard perimeter for privacy and symmetry.
Listing agents: Andrew Whiteley, Wendy Ryan of Brown Harris Stevens, info provided by Coldwell Banker Realty
