Connecticut’s historic mansions tell a story of grandeur, craftsmanship, and quiet refinement, where past and present merge seamlessly. These four estates, each meticulously preserved and thoughtfully updated, offer a glimpse into New England’s architectural legacy. From the stately 1860 James C. Walkley Estate overlooking the Connecticut River to a 1910 country retreat in Washington, these homes embody elegance and exclusivity. A converted 1780 schoolhouse in Sharon brings 18th-century charm into modern luxury, while a restored 1846 farmhouse in New Canaan showcases meticulous craftsmanship across 17.5 private acres. Each residence, with its rich history and sprawling landscapes, offers more than just a place to live—it provides a lifestyle steeped in heritage and sophistication. Whether you’re drawn to ornate fireplaces, grand staircases, or the serenity of pastoral estates, these four Connecticut mansions invite you to step into a world where history is not just preserved but beautifully lived.
1. Restored 1846 Farmhouse
Listed for $7,250,000, Extown Farm is a 17.5-acre historic estate in New Canaan featuring a fully restored 7,000-square-foot farmhouse, renovated in 2023 by Prutting Custom Builders and architect Joeb Moore. The property includes three separate residences: the main house with a new addition, a two-bedroom apartment above a three-bay garage with a gym, and an award-winning one-bedroom guest cottage with a sunroom and ADA-compliant bath. Additional features include multiple barns, an indoor basketball hoop, a former stable, a two-story hobby house, and a seasonal flower and vegetable garden.
Where is New Canaan?
New Canaan, CT, is a town in Fairfield County, located in southwestern Connecticut. It is approximately 48 miles northeast of New York City and 12 miles north of Stamford, offering a convenient commute via Metro-North Railroad. Known for its top-rated schools, historic estates, and architectural significance, New Canaan is home to a vibrant downtown, scenic parks, and mid-century modern landmarks such as Philip Johnson’s Glass House.
Living Room
Exposed wooden beams contrast with white walls and neutral furnishings. Large windows allow natural light to fill the space, highlighting the mix of contemporary and traditional design elements. Open layout connects the main seating area to an adjacent sunroom with additional seating and greenery.
Dining Room
Wooden ceiling beams and wide plank floors contrast with white walls and modern furnishings. A large fireplace with a wooden surround adds character to the space. Natural light streams through multiple windows, creating a bright and inviting atmosphere.
Bedroom
Neutral tones and natural light create a calming atmosphere in this bedroom. A large stone fireplace adds warmth and texture to the space. French doors open to an outdoor area with views of the surrounding landscape.
Patio
A spacious stone patio provides multiple seating areas for outdoor relaxation. A large brick chimney with a built-in fireplace serves as a focal point. The second-floor covered balcony adds additional space for enjoying the surrounding views.
Source: Coldwell Banker
2. Country Estate on 3.8 Acres
Listed for $1,725,000, this 6,115-square-foot country estate in Washington, CT, features a five-bedroom main house with wide-timbered wood floors, exposed beams, built-ins, and multiple living spaces. The property includes a great room with a brick fireplace and 9+ foot ceilings, an updated kitchen with marble counters and stainless steel appliances, and a versatile layout with a formal dining room that can serve as a second primary bedroom. Additional features include a finished walk-out lower level, a 1,196-square-foot guest house with two bedrooms and a fireplace, a Gunite pool, and a private 3.8-acre setting within two hours of NYC.
Where is Washington?
Washington, CT, is a historic town in Litchfield County, located in northwestern Connecticut. It is approximately 40 miles west of Hartford and 90 miles northeast of New York City, making it a desirable rural retreat. Known for its preserved landscapes, cultural institutions, and outdoor recreation, Washington is home to the Steep Rock Preserve, The Gunnery School, and the Institute for American Indian Studies, offering a mix of history, nature, and small-town charm.
Living Room
A spacious living room has vaulted ceilings and large windows that allow natural light to fill the space. White furniture contrasts with a dark-painted brick fireplace that serves as a focal point. A grand piano and a cozy seating arrangement complete the inviting atmosphere.
Kitchen
Exposed wood beams, wide plank flooring, and large windows. White cabinetry and furniture contrast with the warm wood tones of the ceiling and floors. A skylight and pendant lights provide additional illumination over the island and dining table.
Bedroom
Large bedroom has wood flooring, crown molding, and a neutral color scheme. French doors lead to an outdoor space, allowing natural light to enter the room. A seating area with a built-in bookshelf and multiple sofas provides additional comfort.
Bathroom
Freestanding bathtub is positioned beneath a large window with natural light. Light-colored walls contrast with the warm wood flooring. Wall-mounted sconces and a doorway leading to an adjacent space complete the layout.
Source: Coldwell Banker
3. Remodeled 1860 Manor
Listed for $2,750,000, The James C. Walkley Estate is a fully remodeled 1860 manor set on 9.69 acres with views of the Connecticut River. The 5,768-square-foot home features five bedrooms, seven bathrooms (five full, two half), a grand 35-foot entry hall, 13-foot ceilings on the main level, and eight gas fireplaces with marble surrounds. Modern updates include a chef’s kitchen with Wolf, Sub-Zero, and Cove appliances, a butler’s pantry, radiant-heated marble floors in the sunroom, a bluestone patio, and a saltwater pool, blending historic charm with contemporary luxury.
Where is Haddam?
Haddam, CT, is a historic town in Middlesex County, located in central Connecticut along the Connecticut River. It is approximately 20 miles south of Hartford and 30 miles north of New Haven, offering a mix of rural landscapes, waterfront views, and small-town charm. Known for its colonial history, scenic parks, and outdoor recreation, Haddam is home to Gillette Castle State Park, the Goodspeed Opera House, and several nature preserves, making it a desirable location for those who appreciate history and natural beauty.
Foyer
Striped teal walls contrast with dark wood flooring and white trim. A staircase with a dark wooden handrail and white steps leads to the upper level. Framed artwork, decorative furniture, and a red-patterned tablecloth add visual interest to the space.
Living Room
Tall windows with white trim allow natural light to brighten the space. A white marble fireplace serves as a focal point against the orange walls. A mix of modern and classic decor, including a gold-framed mirror and contemporary lighting, adds contrast.
Dining Area
Dark cabinetry with glass doors contrasts with blue-patterned wallpaper. A black dining table is paired with white slip-covered chairs. Natural light enters through multiple windows with woven shades.
Bedroom
Light blue walls contrast with dark wood furniture and white trim. A four-poster bed is paired with navy and white bedding. A decorative fireplace with a marble surround sits beneath a gold-framed mirror.
Source: Coldwell Banker
4. 1780 Converted Schoolhouse
Listed for $1,998,000, this unique country estate in Sharon, CT, features a beautifully converted 1780 schoolhouse as the main residence, along with a guest house, a studio/gym, and multiple outdoor amenities. The 2,151-square-foot main house includes three bedrooms, three bathrooms, a spacious kitchen, a light-filled dining area, a cozy living room with a fireplace, and a primary ensuite bedroom with paneled walls and a second fireplace. Set on scenic grounds, the property also includes a heated pool with a cabana, a barrel sauna, a tennis court, a bluestone porch with pond views, and a detached three-car garage, offering a blend of historic charm and modern luxury.
Where is Sharon?
Sharon, CT, is a rural town in Litchfield County, located in northwestern Connecticut near the New York state border. It is approximately 40 miles northwest of Hartford and 95 miles north of New York City, making it a sought-after retreat for those seeking privacy and scenic countryside. Known for its rolling hills, historic homes, and cultural institutions like the Sharon Playhouse, the town also offers access to outdoor activities such as hiking, fishing, and exploring the nearby Appalachian Trail and Housatonic River.
Dining Room
A dark wood dining table is surrounded by eight matching wooden chairs with woven seats. Large windows allow natural light to fill the space and offer views of the outdoors. A built-in hutch displays glassware and decorative items.
Bedroom
Built-in bookshelves line the walls, framing two large windows with views of the outdoors. A brick fireplace with a wooden mantel is positioned opposite a simple white bed. The hardwood floor complements the wood-paneled walls and cabinetry.
Bathroom
A freestanding clawfoot tub sits beneath a window that allows natural light to fill the space. White beadboard wainscoting runs along the lower walls, complementing the pedestal sink and built-in shelving. A single sconce light is mounted above the mirror, providing additional illumination.
Poolside
Rectangular in-ground pool is surrounded by a stone patio with modern lounge seating. A wooden barrel sauna sits on the grass nearby, adjacent to a small guesthouse with a covered porch. The landscape features tall trees and open views of the surrounding countryside.
Patio
Single-story home with light gray siding has an expansive backyard patio with a built-in fire pit and dining area. A stone outdoor kitchen is positioned near the sliding glass doors leading inside. A greenhouse extends from the side of the house, surrounded by garden beds and mature trees.
Source: Coldwell Banker
