Autumnal fullmoon maple leaves. Aomori Prefecture, Japan

Fall in Love for the Fall: 5 Timeless New England Homes

There’s nothing quite like autumn in New England. The covered bridges and rolling hills set against a backdrop of vibrantly colored leaves makes for an unbeatable picture-perfect setting. Now add to this the cozy atmosphere of relaxing beside a warm fire in an authentic antique home—it doesn’t get more charming than that!

Here are five homes throughout Litchfield County and the Berkshires that make this seemingly unreal fall ambiance come true.

252 Meadow Street—Litchfield, CT

Completed in 1935, this beautiful Litchfield home boasts the elegant style of an 18th century Williamsburg Colonial residence. In its three levels of space, one will find numerous elegant features including arched doorways, a formal dining room with raised paneling and detailed moldings, a curved entry hall, a living room with crown moldings and a library that contains antique barn paneling, solid arched doors, a fireplace and more. Although staying true to its timeless character, the residence contains many updates throughout. Its remodeled kitchen offers a center island, two wall ovens, a walk-in pantry, in addition to a breakfast nook and butler’s pantry with ample storage and serving space. There are five bedrooms and three full and two half baths in total, one of which includes a master suite with a sitting room and fireplace. A screened-in porch overlooking nearly 4 acres of sweeping land and gardens, which rest adjacent to a flagstone terrace, completes the renovated, yet still charismatic, old-world property. Sit back, relax and enjoy the picture-perfect scene of autumn in Litchfield County unfold from the comfort of home.

Timeless Homes for the Fall


9 Macedonia Brook—Kent, CT

Over the past 140 years, this 19th century schoolhouse has evolved into a delightful two-bedroom, two-bath residential gem. The expanded structure was originally built in 1870, and has since been reborn, boasting an open floor plan with a living room and fireplace, dining room and beautifully remodeled kitchen. Interior details that stay true to its historic roots include exposed wood beams, window seats, wide plank floors and vaulted ceilings. A covered front porch greets visitors upon entrance, while a gloriously light-filled sunroom around back opens to a boxwood garden and the property’s meticulously landscaped grounds, which feature an in-ground pool, stone patios, rock outcroppings and stone fences.

Timeless Homes for the Fall


236 Kemble Street—Lenox, MA

This spectacular compound estate in Lenox, MA has over 20 acres of land with amenities including a pond, tennis court, half basketball court and others. The property presents three separate buildings—the original Bishop Estates carriage house, which was constructed in 1894, boasting six bedrooms and four and a half baths, a guest house with three bedrooms and one and a half baths, and a free-standing studio with loft space that has various options for use. The reconfigured main carriage house maintains its original barn doors that open to a main level with expansive open living and a style of pure rustic luxury, offering antique features such as large fireplaces, wood floors and exposed beams, to name a few. Separated into two living spaces, the house also enjoys a guest suite portion with a private entrance that leads to three bedrooms, two full baths, a kitchen, as well as living and dining areas with walls that are uniquely built from authentic horse stalls. Even more housing options continue in the neighboring, fully equipped guest house. And it doesn’t end there! Situated just minutes from the Berkshire’s many cultural gems, this stunning compound estate goes above and beyond all expectations…especially when surrounded by the matchless beauty of autumn in New England.

Timeless Homes for the Fall


Although more recently constructed, these two Georgian-style Colonials in Bethany and Weston, Connecticut have been meticulously built to exemplify the timeless quality of an antique home in New England. 275 Carrington Road, also known as “Pear Tree Farm,” is a lovely country home with a white picket fence located in the town of Bethany, CT. The stately Georgian-style Colonial was added to the 1834 Beri Beecher Homestead in 1991, carefully crafted to fit the tranquil, antique atmosphere of the 5.7-acre property’s roots. Over the last 29 years, the current owners have transformed the residence into an outstanding estate, which has been featured in various reputable decorating and remodeling magazines. Still remaining as part of the original historic homestead, the barn, which can be used as a pool house or studio, dates back to 1850. Despite its recent renovation, the structure features many maintained antique qualities, including its original stone foundation walls. 61 Singing Oaks Drive is yet another Georgian Colonial that rests on over 2 acres of land in Weston, CT. Built just a year later in 1992, the 10,651 square-foot home has four levels of exquisitely designed living space with an exceptional flow that offers privacy and room for formal entertaining. The home amenities are beyond all expectations, offering both an indoor and outdoor pool, upper level game room, gym, pool house and more. Imagine benefiting from all of these modern luxuries, while also savoring the everlasting allure of a historically inspired Colonial home—the possibilities are endless!

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275 Carrington Road
Timeless Homes for the Fall
61 Singing Oaks Drive

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