Period Details | Modern Comfort | Room to Grow Welcome home to 11 West Chestnut Hill, a remarkable piece of Connecticut history now awaiting its next chapter. This magnificent 5-bedroom, 3.5-bathroom property is set on 1.6 picturesque acres, ideally nestled just a half-mile from the historic Litchfield town green. Lovingly hand-built in 1804 by Stephen Clark for his wife and daughter on the site of an old blacksmith and tannery, this residence offers an unparalleled blend of architectural integrity and storied past. As a superb example of colonial architecture, the home retains its traditional "4 over 4" floor plan, featuring four grand, sun-drenched rooms on the first level and four generous bedrooms above, all connected by an elegant central hallway. Step inside and experience the character of historic construction. Watch the light truly dance through the mesmerizing antique crown-glass window panes. The interiors are adorned with exquisite original details, including wide-plank chestnut flooring in the primary suite, built-in closets, and five stately fireplaces that serve as captivating focal points throughout the main rooms.
Thoughtfully designed for flexibility, the first-floor office on the North side boasts handsome vaulted ceilings, an original fireplace, and a dedicated separate private entrance, complete with a separate adjacent driveway. This arrangement makes the space ideally suited for a home business, or guest space. Ascend further to find the finished attic suite-a private retreat complete with a secluded bedroom, a cozy sitting room, and a full bath featuring gorgeous skylight windows and a beautifully refinished antique cast iron tub. The property has been substantially updated to offer modern peace of mind, including a new roof and septic system in 2020, and updated plumbing and appliances in 2022. This is a rare opportunity to own a distinguished piece of Litchfield history with the framework of modern comfort already in place.
Est. $3,900 per month, based on comparable rentals
Sale and tax history for 11 W Chestnut Hill Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24140262
May 1, 2026
Sold
$765,000
$230/sq ft
Apr 24, 2026
Pending
—
Mar 13, 2026
Contingent
—
Nov 20, 2025
Listed
$765,000
$230/sq ft
Nov 18, 2025
Price Changed
$765,000
$230/sq ft
Nov 18, 2025
Coming Soon
$760,000
$228/sq ft
Smart MLS #170421713
Mar 10, 2022
Sold
$612,500
$184/sq ft
Jan 25, 2022
Contingent
—
Dec 2, 2021
Price Changed
$625,000
$188/sq ft
Sep 29, 2021
Price Changed
$675,000
$203/sq ft
Jul 24, 2021
Listed
$699,900
$210/sq ft
Jul 20, 2021
Coming Soon
$699,900
$210/sq ft
This is a great opportunity to secure your very own slice of history w/ this antique Litchfield gem. Meticulously remodeled & designed to showcase the quaint original features, this is a home for those who appreciate charm & flawless attention to detail. From the moment you step inside this remarkable residence, you will be in awe. A formal DR & LR are set just off the entry, both w/ original FP's & direct access through to a casual FR w/ vaulted ceilings & refinished chestnut floors & a feature wall anchored by a FP. The study & a casual breakfast area extends the layout even further plus there’s a beautifully remodeled kitchen for the eager cook. Here, granite counters, a cooking FP & SS appliances are yours to enjoy along w/ quality fixtures & a center island. A 1/2 bath, mudroom, laundry room & garage complete this main level. Upstairs, you’ll find four large bedrooms & two full baths including the master suite. The top floor is finished into a perfect private guest suite w/ vaulted ceilings that inc a lounge area, a separate, bedroom & a full bath. Outside, you will love to host guests on the sun-soaked patio & admire the park-like surrounds w/ lush lawn & mature trees. You will live within a short distance to the village area that has renowned restaurants, schools, shopping, wineries & the Litchfield Green. Those who like to stay active will adore the endless trails, walking paths & bike riding nearby. You’re also only moments from golf courses, skiing & so much more.
Smart MLS #170326377
Oct 7, 2020
Sold
$308,500
$93/sq ft
Sep 10, 2020
Price Changed
$269,900
$81/sq ft
Aug 13, 2020
Listed
$279,900
$84/sq ft
This Fannie Mae home is just minutes from the Litchfield Green. It sits on 1.6 acres with plantings and professional landscaping. Kitchen comes with granite counter tops and a fireplace. 5 bedrooms 3 1/2 baths, 5 fireplaces with Chestnut floor boards throughout. This property is a must see.