Discover a collection of historic estates, each offering a unique blend of classic architecture, preserved charm, and modern amenities. From the 1909 Breezemore Estate in Greenwich, CT, to the 1846 Burr & Abel Calhoun Farm in Washington, CT, these properties showcase timeless craftsmanship on expansive grounds. The 1810 Colonial features a barn and pool on 2 acres, while a 225-acre estate includes a historic inn, event barn, and commercial greenhouse. A 1880 estate provides 7 bedrooms, a pool, and 4 scenic acres, ideal for spacious living and entertaining. Each of these properties presents a rare opportunity to own a piece of history with updated conveniences in sought-after locations.
1. 1909 Breezemore Estate
Priced at $9,750,000, Breezemore is a 9,483 sq. ft. historic estate built in 1909, located in the exclusive Rock Ridge Association of Greenwich, CT, on 3.2 private acres. This 10-bedroom, 9-bathroom home features a grand 3-story staircase, soaring ceilings, intricate millwork, and a newly expanded custom chef’s kitchen with a butler’s pantry and spacious mudroom. The property includes a porte-cochère, circular driveway, a new 60KW generator, and 3,000 sq. ft. of additional FAR for a potential pool house or garage. Offering a blend of historic charm and modern luxury, this estate is just minutes from downtown Greenwich, making it an exceptional opportunity for elegant living.
Where is Greenwich?
Greenwich, Connecticut, is a coastal town in Fairfield County, located on Long Island Sound, about 35 miles northeast of New York City. Known for its affluent neighborhoods, scenic waterfront, and historic estates, Greenwich offers a mix of suburban charm and city convenience with easy access to Interstate 95 and Metro-North Railroad, making it a prime location for commuters. The town is also home to high-end shopping, top-rated schools, golf courses, and cultural institutions, making it one of the most desirable places to live in the New York metropolitan area.
Living Room
Living room has white walls with classic molding and dark hardwood flooring. Large windows allow natural light to enter, creating an airy atmosphere. A fireplace with a black frame adds warmth, complemented by neutral furnishings and modern decor.
Dining Room
White paneled walls, a high ceiling, and hardwood flooring. A long wooden dining table is surrounded by upholstered chairs with modern cutout designs. Large windows and French doors allow natural light to enter, while a crystal chandelier adds refinement.
Kitchen
Kitchen has white cabinetry, deep blue walls, and hardwood flooring. A central island with a black countertop provides seating and additional workspace. Modern light fixtures and large windows brighten the room, while built-in appliances offer functionality.
Bedroom
Large bay windows allowing natural light to enter. A gold-painted ceiling contrasts with white walls and hardwood flooring. A sitting area with armchairs and an ottoman creates a cozy corner near the windows.
Aerial View
A white multi-story home is surrounded by lush greenery and mature trees. A terraced backyard leads to a stone patio with a swimming pool and lounge chairs. Well-manicured hedges and pathways add structure to the expansive lawn.
Source: Coldwell Banker
2. 1846 Greek Revival Estate
Priced at $3,250,000, the Burr & Abel Calhoun Farm is a 3,876 sq. ft. Greek Revival estate built in 1846, located on 24+ acres in the Calhoun Historic District of Washington, CT. The main house features 4 bedrooms, 4 baths, 4 original fireplaces, antique wide hardwood floors, a paneled library, a chef’s kitchen with a bee-hive fireplace, and a sun-filled family room opening to a bluestone patio. The estate includes a charming c.1800 guest house with 2 rooms, 2 baths, and 2 fireplaces, as well as a hand-hewn 1800s Bank Barn, surrounded by apple orchards, perennial gardens, and original stone walls. Modern upgrades include central A/C, a generator, potential long views, and multiple pool sites, making this a rare offering in an A+ location.
Where is Washington?
Washington, Connecticut, is a historic town in Litchfield County, located about 85 miles northeast of New York City and 45 miles west of Hartford. Known for its scenic countryside, rolling hills, and cultural attractions, Washington is home to prestigious private schools, charming villages, and the renowned Mayflower Inn & Spa. The town offers a peaceful rural lifestyle with access to hiking trails, lakes, and historic sites, making it a sought-after retreat in northwestern Connecticut’s Litchfield Hills.
Living Room
Symmetrical arrangement of upholstered armchairs and a central sofa is set on an intricate patterned rug. Large windows with cream-colored drapery allow natural light to brighten the space. Decorative accents such as blue porcelain vases, gold-framed mirrors, and antique wooden tables enhance the room’s traditional style.
Dining Room
Polished wooden dining table with blue-upholstered chairs is set against a backdrop of warm yellow walls. A white fireplace mantel is decorated with blue and white porcelain plates and candlesticks. Large windows with floral drapes allow natural light to highlight the antique wooden furniture and hardwood floors.
Kitchen
Soft blue distressed cabinetry contrasts with warm wooden flooring and beams. A kitchen island with a wooden countertop and barstool seating extends into a cozy sitting area with a fireplace. Built-in stainless steel appliances complement the traditional design elements.
Bedroom
Sloped ceilings and warm-toned walls create an inviting atmosphere. A wooden trunk serves as a functional centerpiece at the foot of the bed with red floral accents. Classic wooden furniture and a writing desk complement the traditional style.
Patio
Stone-paved patio is surrounded by lush greenery and overlooks a historic red barn. Wrought iron furniture with white cushions provides a comfortable outdoor seating area. Manicured hedges and climbing vines enhance the tranquil setting.
Source: Coldwell Banker
3. Restored 1810 Colonial Gem
Priced at $1,250,000, this 4,057 sq. ft. restored 1810 Colonial sits on 2 acres, featuring 4 bedrooms, 3 baths, and a large barn for additional use. The home includes a spacious living room with a wood-burning fireplace, a formal dining room with patio access, a sunroom leading to a mahogany deck, and an updated gourmet kitchen with newer appliances and a laundry/mudroom. The primary suite has a fireplace, full bath, and multiple closets, while the third floor offers two finished rooms and an additional bath for flexible use. Outdoor amenities include an in-ground pool, ornamental trees, perennial gardens, stone walls, and a long circular driveway, with the potential for an additional lot.
Where is Trumbull?
Trumbull, Connecticut, is a suburban town in Fairfield County, located about 60 miles northeast of New York City and 10 miles north of Bridgeport. It offers a mix of residential neighborhoods, parks, and shopping centers, with easy access to Interstate 95, the Merritt Parkway, and Route 8, making it a convenient location for commuters. Known for its top-rated schools, recreational facilities, and preserved open spaces, Trumbull provides a balance of suburban living and proximity to major cities in southwestern Connecticut.
Living Room
Warm wood flooring and white walls adorned with built-in shelves. A deep blue tufted sofa sits atop a patterned area rug, complemented by striped and floral accents. Natural light fills the space through multiple windows, creating an inviting atmosphere.
Dining Room
A refined dining room showcases a large wooden table surrounded by upholstered chairs. A bronze chandelier hangs from a coffered ceiling, adding warmth to the space. Soft white walls, crown molding, and an arched doorway lead to a traditional kitchen.
Kitchen
Cream-colored cabinetry with dark hardware and granite countertops. Stainless steel appliances, including a gas range and dishwasher, add modern convenience. A round wooden table with upholstered chairs provides a cozy dining area.
Bedroom
Wide-plank wood floors and built-in cabinetry. Large windows and French doors allow natural light to enter the space. A decorative fireplace, neutral decor, and vintage-style furniture enhance the charm.
Pool
Large swimming pool is surrounded by a spacious concrete deck and tall, manicured evergreens. The area includes multiple seating options, including lounge chairs and an outdoor sofa set. A traditional white house with black shutters is visible in the background.
Source: Coldwell Banker
4. 225-Acre Estate
Priced at $7,750,000, Maple Lane Farms spans 225 contiguous acres across Preston and North Stonington, CT, featuring a 9,784 sq. ft. estate with 9 bedrooms and 6 baths. The property includes a c. 1993 Cape Cod-style residence with 3 bedrooms, 2.5 baths, and a 3-car garage, along with a c. 1791 Antique Colonial Inn offering 6 bedrooms, 3.5 baths, and a detached garage with an auxiliary apartment. Additional structures include a 2,000 sq. ft. post-and-beam event barn with indoor and outdoor space, an 8,000 sq. ft. hydroponic greenhouse currently producing Bibb lettuce, and multiple storage barns and sheds. The land consists of open meadows, tree plantations, and a 50-acre Christmas tree farm, making it a rare opportunity for residential, agricultural, or commercial use.
Where is Preston?
Preston, Connecticut, is a small town in New London County, located in southeastern Connecticut. It sits approximately 8 miles north of New London, 50 miles southeast of Hartford, and 125 miles northeast of New York City. Known for its rural character, historic farms, and proximity to Foxwoods Resort Casino and Mohegan Sun, Preston offers a quiet, scenic setting with access to major highways and nearby coastal attractions.
Living Room
Living room with warm wood paneling, a brick fireplace, and built-in bookshelves. The space includes light-colored sofas, a wooden coffee table, and an adjoining dining area. Large windows allow natural light to brighten the room.
Dining Room
A long wooden dining table with carved chairs sits beside a large stone fireplace with a wooden mantel. The room features wide-plank wood flooring, exposed beams, and large windows with white curtains. A doorway leads to an adjacent kitchen, enhancing the space’s functionality.
Kitchen
White cabinetry, granite countertops, and a large center island. Multiple windows allow natural light to fill the space, offering views of the greenery outside. A door leads to a screened porch with seating, seamlessly connecting indoor and outdoor areas.
Bedroom
A bedroom with soft blue walls, hardwood flooring, and a wooden bed frame. Large windows provide natural light and views of the surrounding greenery. A seating area with a cushioned chair and a classic wooden dresser complete the space.
Backyard
Light blue house with a pitched roof, large windows, and a central arched window. The backyard includes a stone patio with outdoor seating, lounge chairs, and potted plants. The property is surrounded by lush greenery and mature trees under a bright blue sky.
Source: Coldwell Banker
5. 1880 Estate on 4 Acres
Priced at $3,995,000, this 6,121 sq. ft. home on Hilltop Road sits on 4 acres and features 7 bedrooms, 4 full baths, 1 half bath, and a 2-car garage. Built in 1880, the home includes a spacious kitchen with a grand center island, a family room with a fireplace, a screened-in porch, and a third-floor playroom or gym. The primary suite is located on the second floor along with four additional bedrooms, while the third floor offers two more bedrooms and flexible living space. Outdoor amenities include a heated pool, fenced-in garden, and a large bluestone terrace for entertaining and gatherings.
Where is Sharon?
Sharon, Connecticut, is a historic town in Litchfield County, located in the northwestern corner of the state. It sits approximately 45 miles west of Hartford, 90 miles north of New York City, and 15 miles from the Massachusetts border, offering a quiet, rural setting with easy access to larger cities. Known for its scenic countryside, preserved farmland, and cultural institutions like the Sharon Playhouse, the town is a sought-after retreat for those looking to enjoy the natural beauty of the Litchfield Hills.
Living Room
Living room with light blue walls, hardwood floors, and large patterned area rugs. A black grand piano sits near French doors leading to an outdoor area. A marble fireplace, upholstered seating, and antique-style chairs add to the classic decor.
Dining Room
A long wooden table surrounded by intricately carved chairs with green upholstered seats. A crystal chandelier hangs above the table, complementing the gold-toned walls and elegant drapery. A white fireplace, antique sideboard, and sconces add a sophisticated touch to the space.
Kitchen
Wooden island has built-in cabinets and seating for two with high-backed wooden chairs. A brick accent wall with a black clock and open shelving contrasts with light-colored cabinetry and tiled flooring. Pendant lights with glass enclosures hang above the island, and a row of windows provides natural light.
Bedroom
Hardwood flooring has a white fireplace with a decorative mantel and a gold-framed mirror above it. A blue and white patterned bed sits against a beige wall, accompanied by matching pillows and bedding. A chaise lounge is positioned near two windows with natural wood blinds, allowing ample natural light.
Poolside
Three-story home with a steeply pitched roof and a screened-in porch is surrounded by greenery. A stone retaining wall with shrubs separates the house from a brick-paved patio with lounge chairs and a dining table under a large umbrella. A rectangular swimming pool sits in the foreground with water reflecting the overcast sky.
Source: Coldwell Banker
