$439,539Average Value$274Average Price per Sq Ft1Home For Sale
Tolland is a rural getaway among the forests of Western Massachusetts
Just outside the Berkshires in Western Massachusetts sits the rural hideaway of Tolland, a tiny community of 500 that has been around since the 1750s. What this area lacks in modern conveniences, it makes up for with outdoor opportunities. The many lakes and forests in the area have made this a popular location for second homes.
Tolland is a largely undeveloped, rural town with only one main road cutting through it.
Tolland is a large forest town with many ponds and lakes for recreation.
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A variety of housing and HOAs present
The median home price is $200,000, less than state and national numbers. Homes in the area vary and include Colonials, saltbox, and craftsman styles. Plots of land are also available throughout Tolland. Homes near the center of the community offer plenty of land and direct access to the road that goes through town. “Tolland has several predominantly second-home HOA communities based around lakes,” says Kim Bergland, a broker with Red Horse Real Estate. “There are no real suburban-type neighborhoods.” The HOA and private communities in Tolland can be found on the lakes that dot the area. Association fees vary but can reach more than $200 a month.
A black colonial style clapboard sided home sits on a corner of two main roads in Tolland.
A saltbox style home in Tolland hides behind a large oak tree shading the front lawn.
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Southwick-Tolland-Granville School District
Tolland’s pupils attend the Southwick-Tolland-Granville School District, which is rated C-plus on Niche. The district has only a few schools and is concentrated in Southwick.
Powder Mill Middle School in Southwick serves students in grades 6-8.
Southwick Regional High School in Southwick serves students in grade 6-9.
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State forests and nearby attractions
The area is rich with forests. Nearby, the Tolland State Forest features a 1,000-acre reservoir for boating and fishing and offers plenty of opportunities for camping, hunting and biking. Granville State Forest has horseback riding, cross-country skiing, and hiking trails. Attractions outside of Tolland include Jacob’s Pillow, a performing arts center specializing in dance and has been in the Berkshires since the 1930s. In Windsor Locks, Connecticut, the New England Air and Aviation Museum has multiple historical aircraft and a rotating series of exhibits on display.
A porcupine wanders along the grass in Tolland State Forest plucking dandelions to munch on.
Otis Reservoir, near Tolland, is one of the best lakes in the region for recreational activities.
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Dining and Shopping outside of Tolland
Tolland has no restaurants, but dining options are available in New Boston or Otis. The New Boston Inn, open since 1737, serves lunch options, including sandwiches and burgers, along with chicken and pasta entrees for dinner. In Otis, The Grouse House is a casual seasonal dining spot. The Knox Trail Inn has salads, pizza, and seafood. Shopping is also available outside of Tolland. Granville has a small country store and some smaller boutique shops. However, the closest grocery stores, such as the Big Y, are in Westfield, 18 miles east. Big box stores can also found in Westfield. Baystate Medical Center is 30 miles east in Springfield.
The New Boston Inn, near Tolland, is a historic inn, restaurant, and tavern in Sandisfield.
Westfield is the closest urban area with streets lined with dining for residents of Tolland.
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Route 57 and Bradley International Airport
Route 57 runs through the center of Tolland and connects the community with Springfield to the east and the rest of the Berkshires to the west. The closest airport is Bradley International Airport in Windsor Locks, 24 miles southeast.
Crime in Tolland
According to data from the state of Massachusetts, crime in Tolland has dropped by over 30%, with only two crimes reported in the area in 2024.
Written By
Tyler Patchen
Photography Contributed By
Matt Barrett
Video By
Adam Barkley
Interested in learning more about homes in this area?
Reach out to
Chapin Fish,
an experienced agent in this area.
GreatSchools:
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On average, homes in Tolland, MA sell after 107 days on the market compared to the national average of 57 days. The median sale price for homes in Tolland, MA over the last 12 months is $377,500, up 4% from the median home sale price over the previous 12 months.
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
Beautiful, well maintained, sunny, airy home in coveted private lake community of Wildwood, nestled in the foothills of the Berkshires. Updated, open floor plan, year-round living with gas furnace and fireplace, walk to 1 of 5 sandy beaches with bath houses. New 3 Bedr septic installed 2019. Large 1.13 acre lot provides lots of space for outdoor family fun and entertaining. Vaulted ceiling and
Tucked away in a peaceful corner of Tolland, this beautiful 1-acre wooded parcel offers the perfect setting to build your dream home or private getaway. Surrounded by mature trees and natural beauty, the property provides both privacy and a serene atmosphere while still being conveniently located.Enjoy close proximity to Twining Pond, ideal for relaxing days outdoors, whether you're kayaking,
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
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,
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 boasts many new, major improvements such as: state-of-the-art septic system (2025), roof and skylights (2021), 4-zoned mini-splits (2022), new electrical service (2020), new hot water heater, and
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,
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
An amazing water view home situated on a very private .65 acre lot in the Wildwood Community of Tolland Massachusetts. Gorgeous cherry hardwood flooring, fieldstone fireplace, soaring ceilings with wood and beams, and an open concept floor plan with nearly all rooms having stunning views of the lake and private yard. A beautiful kitchen with windowed cherry cabinets, cherry wood floors, granite
Great opportunity to build your dream vacation or full-time home in the private lake community of Wildwood Property Owners Association. Two adjoining lots totaling just under an acre (.99) have been combined, one is cleared and has passing perc test. Lots are pinned. Enjoy the many amenities of this private lake community as well as all the Berkshires have to offer. Walk to one of 5 beaches, club
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
Beautiful, well maintained, sunny, airy home in coveted private lake community of Wildwood, nestled in the foothills of the Berkshires. Updated, open floor plan, year-round living with gas furnace and fireplace, walk to 1 of 5 sandy beaches with bath houses. New 3 Bedr septic installed 2019. Large 1.13 acre lot provides lots of space for outdoor family fun and entertaining. Vaulted ceiling and
Set within a private lake community with beach access, this contemporary Cape sits on a rare triple lot at the foothills of the Berkshires, offering an ideal balance of lakeside living and everyday convenience. The bright open-concept layout is filled with natural light and opens to peaceful meadow views from the deck. Enjoy five sandy beaches and all the Wildwood community amenities. The second
Your chance to own 32.28 acres in Tolland, MA. Already subdivided into two approved lots (approx. 16 & 15 acres). Partially cleared with a crescent driveway layout cut in; trees are marked to guide your build. A brook runs along the back, offering a serene natural setting. Located in a quiet hilltown known for its natural beauty, trails, and low traffic. Just minutes from Massachusetts' largest
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