Tolland Real Estate

Welcome to Tolland, Massachusetts – a hidden gem nestled in the picturesque Hampden County. This charming town, with its serene landscapes and rich history, offers a unique blend of rural tranquility and community spirit that is hard to find elsewhere.

Tolland is characterized by its lush woodlands, rolling hills, and pristine lakes, making it a haven for outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply soaking in the beauty of nature, the town's scenic parks and trails provide ample opportunities to explore the great outdoors. The nearby Otis Reservoir is perfect for boating and swimming during the warm summer months, while winter brings opportunities for snowshoeing and cross-country skiing.

The town’s sense of community is palpable, with friendly neighbors and local events that bring residents together throughout the year. From farmers’ markets to seasonal festivals, Tolland fosters a welcoming atmosphere that makes it easy to feel at home.

Tolland's real estate market presents a variety of options, from charming historic homes to modern constructions, catering to diverse lifestyles and budgets. With its low crime rates and excellent schools, families find Tolland to be an ideal place to raise children.

With easy access to major highways, Tolland is conveniently located for commuters, allowing residents to enjoy a peaceful rural lifestyle while being just a short drive away from the bustling cities of Western Massachusetts.

Discover the allure of Tolland – where nature meets community, and every day feels like a retreat. Come explore this enchanting town and find your perfect home in the heart of Hampden County.

Newest Listings in Tolland

$422,800

3 Beds ⋅ 3 Baths ⋅ 73544466 MLS

Home being sold fully furnished, Sauna is located in the basement,

154 Brook Ln, Tolland

Listing courtesy of Listing Agent: David P. Hall from Listing Office: Berkshire Hathaway Home Service New England Properties.

$165,000

73531202 MLS

Discover the possibilities with this 32-acre property in the scenic Hilltown of Tolland, Massachusetts. The land has already been divided into two approved building lots of approximately 16 and 15 acres, creating flexibility for development, investment, or a private retreat. Portions of the property have been cleared, with a curved driveway plan already cut in and marked trees outlining potential building areas. Surrounded by woods and abundant wildlife, this setting offers exceptional privacy while still providing convenient access to major routes. Tolland is known for its rolling landscapes, hiking trails, and light traffic, making it an ideal location for those seeking a more relaxed pace. Outdoor recreation is close at hand, with Otis Reservoir close by and offering boating, kayaking, fishing, and swimming. Despite its secluded feel, the property remains accessible, located roughly 12 miles from I-91, about 30 miles from the Massachusetts Turnpike, & near Route 57 for easy travel.

1282 Burt Hill Rd, Tolland

Listing courtesy of Listing Agent: Mary O'Connell from Listing Office: Wolcott Realty.

$49,900

73516385 MLS

Discover the perfect blend of privacy, natural beauty, and ready-to-build convenience at this exceptional nearly half-acre parcel at 23 South Village in the desirable Wildwood Association of Tolland, Massachusetts. Set within 740+ acres of Berkshire woodland, this homesite offers access to Cranberry and Otter Ponds and is surrounded by association land for added seclusion. Extensive groundwork is complete, including perc and pit testing, a well installation, plus an approved septic plan and building permit—making it ready for your dream build. Whether you're planning a weekend retreat or year-round home, this property offers a peaceful escape with essential infrastructure already in place.

23 South Village, Tolland

Listing courtesy of Listing Agent: Amy Rio from Listing Office: Executive Real Estate, Inc..

$449,500

3 Beds ⋅ 3 Baths ⋅ 73512157 MLS

Beautifully appointed 4-season home with stunning views from large great room and deck in the private lake community of Wildwood (WW). This .84 acre property is adjacent to Meadow Beach (1 of 5 WW member beaches) and a lush blueberry patch.The great room is bathed in natural light by a vaulted ceiling, sky lights, & 2 8ft sliders. It features a large granite island and countertops, lots of storage, a pantry & stainless steel appliances.The attached garage makes winter visiting (and living) feel even cozier. WW offers an active and varied social calendar for the whole family and amenities such as a club house, pickle ball & tennis courts, hiking trails and more... The Berkshires offer historic & world class venues such as Tanglewood, Jacob's Pillow, Norman Rockwell museum, and summer stock & traditional theater performances abound. Tolland also offers summer fun like the annual Fireman's Steak Roast, live music, a rural, rustic charm & low taxes.

23 Chipmunk Crossing, Tolland

Listing courtesy of Listing Agent: Joan Maxson from Listing Office: Park Square Realty.

$30,000

73509314 MLS

Be part of a small community with your own ponds and beach for the hot summer months. Escape the crowded beaches to this oasis located in the Wildwood Association of Tolland, MA. On the edge of the Berkshires this rural community is still near CT and NY. This year round or seasonal location is near the happenings of the Berkshires - Tanglewood, museums, skiing. Access can be provided to the community amenities of 5 beaches, Clubhouse, tennis, basketball, pickleball, hiking, fishing, swimming, boating (sail, paddle or electric powered). Don't miss this opportunity.

Lot 43 South Village Rd, Tolland

Listing courtesy of Listing Agent: Susan Como from Listing Office: Buy Rite Home.

$410,000

3 Beds ⋅ 2 Baths ⋅ 73506939 MLS

Contemporary, well maintained 4-season home in private lake resort community of Wildwood (WW), sits surrounded by vibrant perennial gardens. Just steps to 1 of 5 member beaches, this move-in-ready home features gleaming hard wood floors, quartz countertops & ceramic tile backsplash in kitchen. It boasts of many new, major improvements such as: state-of-the-art septic system (2025), roof & skylights (2021), 4-zoned mini-splits (2022), new electrical service (2020), new hot water heater, and it’s been maximally insulated throughout. Nothing to do except relax and bask in the peaceful sights and sounds of nature. Besides the 5 beaches on protected spring-fed ponds, WW offers a club house, tennis & pickle ball courts, hiking, fishing, private campgrounds, social activities and more.The nearby Berkshires are steeped in a rich culture, history and charm. Enjoy visiting some of its world-class venues such as Tanglewood and Jacob's Pillow. Low property taxes. Some photos are AI generated.

32 Woodchuck Hollow, Tolland

Listing courtesy of Listing Agent: Joan Maxson from Listing Office: Park Square Realty.

$65,000

73490718 MLS

Seller is willing to Finance if needed. At the beginning of the Berkshires this wooded acreage puts you near the CT and NY border. Enjoy the sunset with your western view, sit on the back deck of your new home and enjoy dinner at sunset. Not far from the center of town, use the town website to pick an area point of interest to visit or go to "Visit the Berkshires" website to see other local offerings. Buy now and plan for the future, building lots with the charm of this area are getting hard to find so don't miss your opportunity. You want small town New England then check out Tolland with a 2020 census population of 471.

Lot 15 Colebrook River Rd, Tolland

Listing courtesy of Listing Agent: Susan Como from Listing Office: Buy Rite Home.

$305,000

3 Beds ⋅ 1 Baths ⋅ 73471862 MLS

Spend peaceful mornings surrounded by nature in a private setting that backs to protected conservation land at the foothills of the Berkshires. Set on a rare triple lot, this home offers the perfect balance of privacy, tranquility, and everyday comfort. The bright, open-concept layout is filled with natural light and opens to an expansive deck, where deer, birds, and other wildlife regularly visit the property. A first-floor bedroom adds flexibility, while a newer roof and updated septic system provide peace of mind. Enjoy nearby lake access, hiking trails, boating, kayaking, fishing, and skiing at Otis Ridge. Convenient to Hartford/BDL Airport, Springfield, Boston, and New York, it's an ideal year-round home or weekend escape.

200 Fox Den Rd, Tolland

Listing courtesy of Listing Agent: Team ROVI from Listing Office: Real Broker MA, LLC.

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