Timber Trails Real Estate

Welcome to Timber Trails, a hidden gem nestled in the serene town of Sherman, Connecticut, within the picturesque Fairfield County. This charming neighborhood offers a unique blend of natural beauty and community spirit, making it an ideal place for families, retirees, and anyone seeking a peaceful retreat from the hustle and bustle of city life.

Timber Trails is characterized by its lush woodlands, rolling hills, and tranquil lakes, providing residents with ample opportunities for outdoor activities. Whether you enjoy hiking, fishing, or simply taking leisurely strolls, the area’s scenic trails and pristine nature reserves invite you to explore the great outdoors. The nearby Candlewood Lake, Connecticut's largest lake, is perfect for boating, swimming, and picnicking, ensuring that every day can feel like a vacation.

The community itself is tight-knit, with friendly neighbors and a welcoming atmosphere. Local events, farmers' markets, and seasonal festivities foster a sense of belonging and make it easy to forge lasting friendships. Families will appreciate the top-rated schools in the region, which emphasize academic excellence and community involvement.

Sherman's charming downtown area is just a short drive away, offering quaint shops, delightful eateries, and essential services. With easy access to major highways, residents can enjoy the tranquility of Timber Trails while still being within reach of urban conveniences and attractions in nearby towns.

Discover the elegance of Timber Trails, where nature meets community, and make this enchanting neighborhood your new home!

Newest Listings in Timber Trails

$1,495,000

6 Beds ⋅ 6 Baths ⋅ 24167831 MLS

Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and you'll feel it immediately-the sense of grace that lingers in homes built with heart. Wide-board chestnut and white pine floors, dual staircases, and charming hidden nooks invite you to wander, to slow down, to imagine the lives that came before. The generous yet intimate flow of the main level makes it equally suited for fireside evenings or lively gatherings. At its center lies the kitchen, beautifully reimagined for today while honoring its past. Soapstone countertops, custom cabinetry, and high-end appliances meet the warmth of an original fireplace and the practicality of a walk-in laundry room. Beyond the doors, your private world awaits. A heated, in-ground saltwater Gunite pool with automatic cover and outdoor shower sits tucked among lush gardens and gentle breezes, home abuts valley pond adding a hush of serenity. Extensive upgrades have been completed, from new mechanical systems to refined details throughout, ensuring comfort in every season. With central air, steam/hot air heating, and a standby generator, every modern convenience is in place. For Sale and or Lease.

201 Rte 37 S, Sherman

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.