4 Historic Mansions in Connecticut Blend Period Charm with Modern Updates

Discover a collection of historic estates that offer privacy, scenic landscapes, and timeless architecture. From a 1910 riverfront log home with a guest cottage to a 1780 colonial estate on 100 acres in the exclusive Doolittle Lake community, these properties provide a rare opportunity to own a piece of history. The 1810 estate in Greenfield Hill features a guest house, barn, and pool, while the 1790 riverside estate sits on 40+ acres with a guest cottage and heated gunite pool. Each home blends period charm with modern amenities, creating unique retreats in some of Connecticut’s most desirable locations.

1. 1910 Riverfront Log Home 

Priced at $5,500,000, this 4,636 sq. ft. log home, built in 1910, sits on a private estate with over 500 feet of direct waterfront on the Saugatuck River in Westport, CT. The 4-bedroom, 4-bathroom residence offers one-floor living, an inground gunite pool, and beautiful grounds, creating a tranquil retreat just one hour from New York City. Previously featured in magazines and home tours, this unique property has been home to various theatrical figures before becoming a private residence. Additionally, a separate legal 2-bedroom cottage is included on the property, currently rented, providing additional space or rental income.

Where is Westport?

Westport, Connecticut, is a coastal town in Fairfield County, located about 50 miles northeast of New York City along Long Island Sound. Known for its beaches, waterfront estates, vibrant arts scene, and top-rated schools, Westport offers a mix of suburban living with easy access to Interstate 95 and the Metro-North Railroad, making it a desirable location for commuters. The town features high-end shopping, fine dining, cultural attractions like the Westport Country Playhouse, and outdoor recreation along the Saugatuck River and Compo Beach.

Related: The 42 Countries That Shaped Connecticut in 1900: A Snapshot of Immigration and Identity

Living Room

Living room with log walls, a vaulted ceiling, and exposed wooden beams. A large stone fireplace with a thick wooden mantel serves as the focal point. Plush seating, a red-patterned rug, and a chandelier create a cozy and inviting atmosphere.

Dining Area

Wood-paneled walls and exposed log beams define the dining and living area, with a vaulted ceiling and skylights allowing natural light. A long wooden dining table with plaid-upholstered chairs sits on a checkered wood floor, and built-in bookshelves line one wall. A handcrafted staircase with twisted branches leads to a loft with a decorative railing, adding an additional level to the space.

Kitchen

Green wooden cabinets and butcher block countertops define the kitchen, with a large window over the sink providing natural light. A central island with woven-seat barstools adds seating and workspace, while an open hutch displays dishware. A brass chandelier hangs above the dining table, and a red-framed door leads outside, complementing the log walls.

Bedroom

A stone fireplace with a rustic wood beam mantel serves as the focal point of the bedroom, framed by log walls. A bed with a red and white quilt and large patterned pillows sits against a windowed wall with natural light. A wooden wardrobe and vintage-style decor complete the space, adding warmth and character.

Related: These are 25 of the Best Towns to Retire to in Connecticut Taking the Costs of Buying a Home and Homeownership Into Consideration Along with Six Other Key Criteria

Pool

Freeform swimming pool with a stone border is set within a landscaped yard with mature trees and flowering shrubs. Lounge chairs, potted plants, and a patio table with an umbrella create a relaxing seating area. The surrounding lawn and dense foliage provide a private and serene setting.

Source: Coldwell Banker

2. 780 Colonial Estate on 100 Acres 

Priced at $4,995,000, this 5,671 sq. ft. 1780 center hall colonial sits on 100 acres within the exclusive 1,700-acre Doolittle Lake Company woods. The 6-bedroom, 8-bathroom home features colonial and art deco details, wide red pine floors, high ceilings, two wet bars, and nine wood-burning fireplaces, preserving its historic charm. Renovated by architect Robert Carrere in the 1930s, the home includes a gourmet kitchen with custom cabinetry, a sunroom, stone-walled perennial gardens, and a custom oval heated gunite pool with a pool house. Ownership provides private access to hunting, fishing, boating, and hiking, offering a rare opportunity for secluded lakefront living just 2.5 hours from New York City and Boston.

Where is Norfolk?

Norfolk, Connecticut, is a small town in Litchfield County, located about 45 miles northwest of Hartford and 120 miles northeast of New York City. Known as the “Icebox of Connecticut” due to its cool climate, Norfolk is home to three state parks, miles of hiking trails, and the private, pristine Doolittle Lake. The town is also recognized for its historic architecture, vibrant arts scene, and the renowned Norfolk Chamber Music Festival, making it a cultural and nature-rich destination in northwestern Connecticut.

Living Room

A fireplace with a white wood mantel and framed landscape painting serves as the focal point of the living room. Upholstered armchairs, a red settee, and antique-style tables create a classic seating arrangement. Large windows allow natural light, while decorative lamps and artwork enhance the traditional ambiance.

Related: 5 Historic Mansions in Connecticut Showcase Timeless Craftsmanship

Dining Room

Dark wood dining table with intricately carved chairs sits atop a patterned area rug in a spacious dining room. A black fireplace with a framed painting and decorative candlesticks serves as a focal point. Large windows with green drapes and French doors bring in natural light and offer views of the surrounding greenery.

Bedroom

Four-poster wooden bed with white linens and pink accents is centrally positioned in the bedroom. Large windows with a built-in window seat and patterned cushions provide natural light and an inviting reading nook. An open doorway leads to an en-suite bathroom with a visible clawfoot tub.

Pool

Circular swimming pool with a stone patio is surrounded by greenery and mature trees. A white pool house with arched openings provides a shaded seating area with outdoor furniture. Lounge chairs and manicured landscaping create a serene and private setting.

Source: Coldwell Banker

3. Restored 1810 Estate 

Priced at $2,295,000, this 5,291 sq. ft. 1810 estate sits on over two acres in the scenic Greenfield Hill area of Fairfield, CT. The 7-bedroom, 6-bathroom home has been meticulously restored, featuring hand-hewn wide plank wood floors, exposed beams, bay windows, custom built-ins, and four wood-burning fireplaces. The property includes a two-story legal guest house, a large renovated barn, a garage with a bonus room, and a greenhouse attached to a spectacular room with brick flooring and an oversized fireplace. Outdoor amenities include stone walls, an expansive stone terrace, mature landscaping, and a luxurious gunite pool and spa, all within minutes of Fairfield center, Metro-North train, Southport Village, and local beaches.

Where is Fairfield?

Fairfield, Connecticut, is a coastal town in Fairfield County, located about 50 miles northeast of New York City along Long Island Sound. Known for its top-rated schools, vibrant downtown, and five public beaches, Fairfield offers a mix of suburban charm and waterfront living with easy access to Interstate 95 and the Metro-North Railroad, making it a prime location for commuters. The town features historic homes, upscale shopping, dining, golf courses, and recreational amenities, making it one of the most desirable communities in southwestern Connecticut.

Foyer

A grand staircase with black steps, white risers, and a matching handrail leads to the upper level of the home. Glossy black hardwood floors contrast with the crisp white walls and paneled doors. A chandelier with curved arms hangs from the ceiling, adding a traditional touch to the space.

Dining Room

Glass dining table with six upholstered chairs sits atop a patterned rug. Large bay window allows natural light to brighten the white walls and blue ceiling. Black chandelier hangs from the ceiling, and modern artwork decorates the walls.

Bedroom

Large bedroom with a fireplace framed by teal built-in shelves and sconces. Wide plank wood floors contrast with cream-colored walls and bedding. French doors and windows allow natural light and views of the wooded outdoors.

Bathroom

White vanity with a marble countertop and black faucet sits below a gold-framed mirror. Large window allows natural light to brighten the space, showing a view of the outdoors. Marble-tiled shower with built-in shelving is enclosed by a glass partition.

Source: Coldwell Banker

4. 1790 Riverside Estate on 40+ Acres 

Priced at $2,750,000, Firefly Farm is a 4,071 sq. ft. estate built in 1790, set on 40+ private acres with the West Aspetuck River flowing through the property. The 4-bedroom, 5-bathroom main residence retains its historic charm with five fireplaces, a country kitchen, a formal dining room, a large living room, a library, and a media room. Outdoor amenities include a heated gunite pool, sports court, and a pond-side guest cottage, all accessed via a long private driveway off a scenic unpaved road. Once home to Oscar-winning actor Frederic March, this tranquil retreat is located 15 minutes from New Preston, less than 20 minutes from Kent, and approximately 1.5 hours from New York City.

Where is New Milford?

New Milford, Connecticut, is the largest town by area in Litchfield County, located about 75 miles northeast of New York City and 25 miles north of Danbury. Situated along the Housatonic River, New Milford offers a mix of historic charm, vibrant downtown shops, and outdoor recreation, including Lovers Leap State Park and Candlewood Lake, the largest lake in Connecticut. With a blend of rural landscapes, preserved farmland, and modern conveniences, the town provides a balance of country living and accessibility to major highways and Metro-North train stations.

Living Room

Spacious living room with a beamed ceiling and wide plank wood floors. Large windows bring in natural light and provide views of lush greenery. Fireplace with a white mantel sits opposite a sectional sofa and modern furnishings.

Kitchen

Kitchen with wooden cabinetry and granite countertops. Large central island with a sink provides additional workspace and storage. Stainless steel appliances, including a professional-grade range, are integrated into the layout.

Bedroom

Bedroom with a sloped ceiling and hardwood floors. Large bed with neutral bedding sits near two windows that bring in natural light. Fireplace and a small seating area with modern chairs complete the space.

Pool

Rectangular swimming pool surrounded by a stone patio and lush greenery. Mature trees and manicured landscaping provide a scenic backdrop. Lounge chairs and an outdoor dining area sit near the water’s edge.

Source: Coldwell Banker