Connecticut’s rolling hills and historic towns hold some of New England’s most exquisite estates—homes that have witnessed centuries of change while preserving the craftsmanship and elegance of their eras. Tucked into quiet corners of the state, these grand residences blend period architecture with modern luxuries, offering a rare opportunity to own a piece of history. Whether it’s a Revolutionary-era farmhouse with rustic charm, a palatial Georgian Revival with ornate woodwork, or a riverfront retreat that has stood for over 270 years, each estate tells a story of those who built, lived, and entertained within their walls.
Among Connecticut’s finest, Ballyhack Farm (1760) in Cornwall stands as a testament to early American design, originally a major logging farm that now offers scenic tranquility and refined interiors. In Fairfield County, the Homewood Estate (1755) dazzles with its 50-foot ballroom, 13 fireplaces, and a grandeur that recalls Gilded Age glamour. Meanwhile, the Thorp House Estate (1750) in Easton, sprawling over 24.5 acres, combines pastoral beauty with historic charm, featuring exposed beams, a stone fireplace, and a cottage overlooking the countryside.
More than just homes, these estates are living history—preserved yet adapted for the modern era. They offer an unparalleled combination of craftsmanship, luxury, and a sense of place, making them some of the most desirable historic properties in New England.
1. Historic 1760 Ballyhack Farm
Priced at $1,620,000, Ballyhack Farm is a 3,899 sq. ft. historic home built in 1760, once a major logging farm and documented in the Cornwall Historical Society. The 5-bedroom, 4-bathroom home features high ceilings, large rooms, a center hall entry, a living room, parlor, den, and a first-floor bedroom option. Modern updates include a well-organized chef’s kitchen and a sunroom addition, providing indoor-outdoor living with views over a bird sanctuary.
Where is Cornwall?
Cornwall, Connecticut, is a small, rural town in Litchfield County, located about 40 miles west of Hartford and 95 miles north of New York City. Known for its scenic landscapes, covered bridges, and outdoor recreation, Cornwall is home to Mohawk Mountain Ski Area, making it a popular destination for winter sports. With historic farms, preserved woodlands, and access to the Housatonic River, the town offers a quiet retreat with a strong connection to nature and New England charm.
Foyer
A spacious foyer features sage green wainscoting, hardwood floors, and a red Persian rug. A chandelier hangs from the ceiling, and double doors open to a scenic landscape. Modern artwork and a bold yellow mirror contrast with the classic architectural elements.
Living Room
Historic living room has a large fireplace with a white wooden mantel and built-in cabinetry. The space is furnished with blue upholstered seating, a Persian rug, and a glass-top coffee table. Large windows bring in natural light, and modern artwork contrasts with the classic elements.
Kitchen
Kitchen has cream-colored cabinetry, dark countertops, and a large island with seating. Stainless steel appliances, including a double-door refrigerator, complement the contemporary barstools. Multiple windows allow natural light to brighten the space, highlighting the wide-plank wood flooring.
Bedroom
Four-poster bed with patterned bedding and matching upholstered chairs. Exposed wood beams contrast with white walls and blue trim around the windows and doors. Natural light enters through multiple windows, complementing the warm tones of the hardwood flooring and furnishings.
Patio
A traditional white house has a sunroom with large windows and a gabled roof. A tiered stone retaining wall surrounds a landscaped garden with flowering plants and greenery. An outdoor dining area with wooden furniture is set on a gravel patio overlooking the property.
Source: Coldwell Banker
2. 1755 Homewood Estate
Priced at $4,795,000, “Homewood” is a 12,853 sq. ft. estate built in 1755, expanded in 1890 by NYC banker George Haven, and extensively updated with $2M in renovations. Set on 3.22 manicured acres, this 8-bedroom, 9-bathroom home features 13 fireplaces, a 50-foot ballroom designed by Elsie de Wolfe, a chef’s kitchen with a butler’s pantry, and a grand Great Hall with mahogany staircases. Outdoor amenities include a heated gunite pool and spa, a pool house with a full kitchen and bath, multiple porches and terraces, and three carriage-style garages with a porte-cochère. Located in Fairfield County’s premier Silver Spring area, just moments from the New York border, this estate blends historic elegance with modern luxury, featuring an elevator, radiant heated floors, and a generator.
Where is Ridgefield?
Ridgefield, Connecticut, is a historic town in Fairfield County, located about 60 miles northeast of New York City and 20 miles southwest of Danbury. Known for its charming Main Street, top-rated schools, and cultural attractions, Ridgefield offers a blend of New England charm and modern conveniences. With preserved historic homes, scenic parks, and venues like The Ridgefield Playhouse, the town provides a vibrant arts scene, outdoor recreation, and a strong sense of community while remaining easily accessible to major highways and Metro-North train stations.
Living Room
Living room has intricate wall paneling, large windows, and French doors. An ornate fireplace with a decorative mirror is the focal point of the room. Antique-style furniture with upholstered seating and a large patterned rug complement the traditional design.
Dining Room
A long wooden dining table is surrounded by ten matching chairs and two upholstered armchairs. A chandelier hangs above the table, while a fireplace with a portrait above it serves as a focal point. Patterned wallpaper, gold-framed mirrors, and a large area rug add traditional design elements.
Bedroom
Large wooden bed with gold bedding is positioned against a patterned wallpapered wall. A fireplace with a white mantel serves as a focal point between two sets of French doors. Leather wingback chairs and a teal loveseat add seating to the space.
Pool
In-ground swimming pool is surrounded by a stone patio with lounge chairs and an umbrella. A pool house with a gambrel-style roof and covered seating area is positioned nearby. The main house, featuring dormer windows and multiple chimneys, is visible in the background.
Source: Coldwell Banker
3. 1750 Thorp House Estate on 24.5 Acres
Priced at $3,995,000, this historic 1750 estate, listed on the National Register of Historic Places, spans 24.5 acres of riverfront property in Easton, CT. The 4,170 sq. ft. main house features 5 bedrooms, 3 baths, cathedral ceilings in the kitchen and great room, and authentic period details, offering a blend of historic charm and modern comfort. The estate also includes a 1-bedroom rental cottage with an attached 2-car garage, scenic walking trails, stone walls, a pond, and flagstone terraces overlooking open fields and the Aspetuck Valley Country Club golf course. Located within walking distance to the Blue Bird Inn and local orchards, this property provides a rare opportunity to own a treasured family estate known throughout the community.
Where is Easton?
Easton, Connecticut, is a rural town in Fairfield County, located about 50 miles northeast of New York City and 10 miles north of Bridgeport. Known for its scenic farmland, historic homes, and strong agricultural roots, Easton offers a peaceful, small-town atmosphere with rolling hills, nature trails, and local farms such as Silverman’s Farm and Sherwood Farm. With top-rated schools, access to major highways, and proximity to cultural and shopping hubs in Fairfield and Westport, Easton is a desirable location for those seeking privacy and a connection to nature while remaining close to urban conveniences.
Great Room
A large living space showcases exposed wooden beams, a vaulted ceiling, and a stone fireplace with a fire burning. A grand piano sits near tall windows that let in natural light. The seating area consists of upholstered sofas and chairs arranged around an ornate rug.
Kitchen
Kitchen has exposed wooden beams, natural wood cabinetry, and terracotta floor tiles. Large window above the sink allows natural light to fill the space. Rustic dining table is set for a meal, surrounded by green wooden chairs.
Bedroom
Wood-paneled ceiling and exposed beams create a warm atmosphere in the bedroom. Built-in bookshelves frame a seating area with two white fur-lined chairs and a small table. Large area rug with intricate patterns adds color to the wooden floor.
Patio
Slate stone patio extends from the house, providing multiple seating areas with cushioned chairs and wrought iron benches. Flowering shrubs and fall foliage surround the space, adding seasonal color. French doors lead from the house to the patio, connecting indoor and outdoor living areas.
Source: Coldwell Banker
It’s easy to overlook the hidden gems in Connecticut! I love the Homewood Estate, but don’t forget about the Hill-Stead Museum with its beautiful gardens and art collection. The Lockwood-Mathews Mansion is also a must-see. it really brings the Gilded Age to life. Such rich history everywhere!
Those mansions are stunning. Have you checked out the Mark Twain House? It’s such a cool glimpse into his life. And the Bush-Holley House is lovely too!
I’ve definitely strolled through the halls of the Mark Twain House! It’s like stepping into a time machine where early American charm meets Twain’s humor. I love exploring history!