Tolland County Real Estate Search

Tolland County Historical Properties for Sale

Our website features the best real estate search for historical properties available in Tolland County and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Tolland County Historical Homes for Sale

$749,000
4 Beds 3 Baths 24196094 MLS
Experience the perfect blend of luxury, privacy, and equestrian living at this exceptional estate set on 6.94 picturesque acres in the heart of Willington, Connecticut. Thoughtfully designed for both elegant entertaining and everyday comfort, this remarkable property offers resort-style amenities, premium finishes, and outstanding functionality. The beautifully appointed main residence showcases a sophisticated chef's kitchen featuring a Wolf gas range, Sub-Zero wine cooler, and both the Sub-Zero refrigerator and Asko dishwasher seamlessly concealed behind custom cabinetry for a sleek, integrated look. Modern conveniences including mini-split systems, a whole-house gas generator, and a SPAN smart electrical panel provide year-round comfort, efficiency, and peace of mind. Step outside to your own private backyard oasis complete with a heated in-ground pool, inviting hot tub, and charming pool house-perfect for relaxing or hosting unforgettable gatherings. The expansive grounds are equally impressive, featuring mature apple and blueberry trees, open green space, and scenic views that create the feel of a private country retreat. Equestrian enthusiasts will appreciate the property's outstanding horse facilities. The impressive barn/garage offers space for up to four vehicles and is topped with 50 owned solar panels, providing exceptional energy efficiency. The current owners enjoy minimal to virtually no electric costs, making this an incredible long-term value in addition to

56 Old Farms Rd, Willington

$369,900
2 Beds 1 Baths 24189988 MLS
Step back in time and discover the timeless charm of this 1946 Cape nestled on over 11+ picturesque acres along a quintessential country road. Filled with character, this inviting home showcases H/W floors, graceful archways, French doors, and beautiful original details throughout. The eat-in kitchen features cherry cabinetry, a pantry, Bosch dishwasher, SS refrigerator, and a casual dining area that flows seamlessly into the formal dining room. The dining room is a true standout with H/W floors, dual corner hutches, and an extra-wide archway that adds warmth and classic appeal. Relax in the cozy living room highlighted by a FP, picture window, and French door leading to the sunroom with custom built-ins. The upper level offers two comfortable bedrooms and a full bath, while the full basement provides excellent storage or future possibilities. Outside, enjoy the covered patio overlooking the expansive property. Equestrians, hobby farmers, and outdoor enthusiasts will appreciate the impressive two-story, 5-stall barn complete with a tack room, along with several additional outbuildings. Additional highlights include a new septic tank and the potential for future opportunities, as buyers are encouraged to perform their own diligence regarding possible subdivision or building options. While the home could benefit from some updating & TLC, it presents an exceptional opportunity to restore its original beauty and create something truly special in a peaceful country setting.

123 Stafford St, Stafford

$550,000
3 Beds 2 Baths 24193967 MLS
Built in 1750, this beautifully updated & meticulously maintained historic antique Colonial blends timeless character with modern comfort. Rich wide-board floors and classic 12-over-12 windows highlight its heritage, complemented by four fireplaces throughout the home. The inviting kitchen features granite countertops, custom cabinetry, a wood stove, and abundant natural light from multiple windows and a sliding door leading to the patio-perfect for everyday living & entertaining. A charming library with custom built-ins sits just off the kitchen, offering a cozy and functional retreat. Features a first floor bedroom.Both the living and dining rooms showcase impressive fireplaces with updated liners, enhancing both style and efficiency. Two staircases provide convenient access to the second floor, where you'll find two spacious bedrooms, a beautifully remodeled full bath, and an additional room ideal for a nursery. An open landing area between the bedrooms offers flexible space for a home office or playroom. New asphalt roof installed May 2026. New well pipe from well house to house installed Summer 2026. Set on 3.8 acres of rolling, usable land, the property also features a new driveway, an expansive three-car garage with a loft workshop-perfect for hobbies, storage, or creative pursuits, a barn and a well house. A rare opportunity to own a thoughtfully preserved historic home with modern updates in a serene setting. Please do not drive up the driveway without an appointmen

355 Wall St, Hebron

$675,000
3 Beds 2 Baths 24186602 MLS
Steeped in New England history and perfectly positioned directly across from Shenipsit Lake, this extraordinary farmhouse traces its origins to the 1700s before being thoughtfully expanded in the 1840s during the Civil War era. Inside, you'll discover wide pine floors, hand-hewn exposed beams, three fireplaces, and beautifully preserved architectural details that capture the craftsmanship of centuries past. Thoughtful updates provide modern comfort without sacrificing authenticity, including central air, replacement windows, updated siding, a 60-year roof, generator hookup, new well pump, and numerous additional improvements completed by the current owners as they meticulously restored the home from the windows and sheetrock to the mechanical systems. Offering the flexibility of up to four bedrooms, the home also features a private in-law suite, providing an ideal layout for multigenerational living, guests, or extended family. Step outside to experience over 6.5 picturesque acres, where a beautifully rebuilt historic barn, fenced in-ground pool, mature landscaping, and open grounds create endless opportunities for horses, hobby farming, gardening, recreation, or simply enjoying the peaceful Connecticut countryside. The property also offers potential for future subdivision (buyer to perform due diligence), making it as appealing for its possibilities as it is for its beauty. Conveniently located just minutes from the University of Connecticut. A MUST SEE

352 Shenipsit Lake Rd, Tolland

$399,900
2 Beds 2 Baths 24186399 MLS
An exceptional investment or owner-occupant opportunity awaits at 596-598 Main Street, a premier commercial property nestled in the heart of historic downtown Somers, Connecticut. This unique 0.59-acre lot features a beautifully preserved, pre-Revolutionary complex dating back to 1750 and 1789, comprised of three separate freestanding retail and office buildings totaling 3,449 square feet of flexible space. The multi-building layout allows an owner to run a business from one structure while collecting reliable, multi-stream rental income from the others. Zoned entirely for business, the property perfectly accommodates boutique retail storefronts, professional offices, creative studios, or specialty shops looking to capture the area's rich New England charm. Positioned on a high-visibility regional retail corridor, the property boasts 106 linear feet of direct, paved frontage along State Route 190 and Route 83. It features highly visible pylon signage to maximize exposure and offers on-site parking for convenient access. This landmark location sits diagonally across from the historic Somers Inn and enjoys heavy daily commuter and neighborhood traffic. Tenants will benefit from unmatched walkability to core local amenities, including Geissler's Supermarket, banking, and popular dining spots like Mario's Restaurant, Hometown Kitchen, a local favorite. Less than a mile from local schools, driving steady family traffic. Schedule your private tour of this multi-building asse

596 Main St, Somers

$182,000
7 Beds 3 Baths 24181307 MLS
Rare opportunity to own a unique property with exceptional potential in the heart of Stafford Springs. Situated on a spacious parcel with natural features, including a brook, wetlands, and access to the beauty of the surrounding area, this property offers a blank canvas for investors, builders, developers, outdoor enthusiasts, or buyers seeking a private retreat. The existing home has been substantially gutted and will require extensive rehabilitation or replacement. The property is being sold strictly as-is. Buyers are encouraged to conduct their own due diligence regarding the condition of existing structures, permitted uses, zoning regulations, wetlands requirements, and future development possibilities. In addition to the main structure, the property includes an outbuilding that provides valuable storage space and flexibility for future use. Existing improvements may offer a starting point for redevelopment, renovation, or a custom project tailored to your vision. The land itself is one of the property's most attractive features. The natural setting provides privacy and a peaceful environment while remaining conveniently located near local amenities, schools, shopping, restaurants, and major commuter routes. Enjoy nearby recreational opportunities, including lakes, hiking, fishing, boating, and outdoor activities that make this area desirable year-round. Whether you are looking to create a custom residence, explore investment possibilities, e

24 New City Rd, Stafford

$599,900
4 Beds 2 Baths 24178093 MLS
Steeped in history and timeless New England charm, the historic Nathaniel Loomis House, built in 1718, offers a rare opportunity to own one of Bolton's original homesteads. Rich in heritage and beautifully preserved, this remarkable property has evolved through centuries while maintaining the character and craftsmanship that make antique homes so special. Originally established by Nathaniel Loomis, one of Bolton's earliest settlers, the property later became a thriving working farm with 22 Jersey cows, kennels for field trial dogs, and fields that produced fruits and vegetables for local markets. In 1963, the estate entered a new chapter as Fernwood Farm, an equestrian property dedicated to breeding and raising Morgan horses. Today, this stunning 2,178 square foot Colonial showcases authentic exposed post and beam construction, wide board flooring throughout, and the warmth and craftsmanship only found in homes of this era. The residence offers remodeled kitchen with unique brick flooring, 4 bedrooms and 2 full baths, blending historic character with thoughtful modern updates. Recent renovations were completed by the renowned Country Carpenters, specialists in traditional post-and-beam construction, ensuring the home's integrity and historic appeal were carefully preserved. Equestrian enthusiasts and hobby farmers alike will appreciate the impressive barn featuring 8 stalls, paddock areas, and fenced pastures ready for horses or livestock.

261 Hebron Rd, Bolton

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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.