Community profile

Benson Woods

Periwinkle Drive, Middlebury, CT

55+ community

About the community

About Benson Woods

About Benson Woods Benson Woods is a 55+ community in the charming town of Middlebury, Connecticut. Active adults will love the quiet setting and scenic landscaping that is bordered by Eight Mile Brook. Adults 55 and better can enjoy a low-maintenance lifestyle while living in a beautiful classic New England-style home in a charming age-restricted neighborhood. Benson Woods Amenities Active adults can enjoy all of the social and physical activities that will be held at the proposed clubhouse in Benson Woods. The clubhouse will have a fully-equipped fitness center where homeowners can stay fit and avoid gym membership fees. There will also be a multi-purpose room and plenty of scenic outdoor space with walking and biking trails surrounding the community. Benson Woods Homes & Real Estate Construction at Benson Woods began in 2004 and this community will have a total of 79 residences upon completion. Benson Woods consists of single-family homes and duplex homes, which feature high ceilings, great rooms, large primary suites on the first floor, second-floor lofts, dens that can be converted into second bedrooms, porches, full basements, and plenty of storage space. Every home in Benson Woods is designed in a classic, New England-style that showcases the picturesque beauty of Middlebury. Benson Woods provides active adults with plenty of living space that's great for entertaining guests. All homes have one to two to four bedrooms, two to four bathrooms, and a two- to three-car garages. Duplex homes offer 2,354 to 2,557 square feet of living space and single-family homes offer 1,762 to 2,557 square feet of living space. Benson Woods Lifestyle Homeowners living in Benson Woods can enjoy their free time instead of worrying about exterior home chores due to the homeowners association (HOA) fee. The HOA fee includes lawn maintenance and exterior home maintenance. Active adults can spend time relaxing, socializing or strolling through the 96 acres of beautiful natural space. Area Middlebury is a beautiful town full of classic New England charm and lush landscaping. Active adults have easy access to Interstate 84. Some of the area attractions include the Palace Theater, Quassy Amusement Park, The Timex Museum, and Sandy Beach Swim Club. There are also plenty of shopping and restaurant options nearby. Residents also have easy access to nearby cities like Danbury and New Haven, which are 22 miles away as well as Hartford, which is only 35 miles away. For farther travel, residents can head to Bradley International Airport in Hartford, which is only 49 miles away. Active adults will love living in a charming 55+ community that has amenities and attractive scenery in Benson Woods in Middlebury, CT.

Verified overview

What we know from public sources

Age restriction
55+
Community size
79 homes
Home types
Single-Family, Attached
Housing offering
Homes for sale
Construction years
2004–present
Published HOA
Not publicly found
Published home purchase range
High $400ks - Low $600ks
Community features
Not publicly found
Last source check
August 5, 2026

Source-published features

Amenities and services

Grouped so you can scan what affects day-to-day life before opening an operator page.

Health & wellness

  • Fitness Center
  • Parks & Natural Space

Activities & engagement

  • Clubhouse
  • Health Club
  • Library
  • Clubhouse/Amenity Center

Outdoor spaces

  • Walking & Biking Trails
  • Golf Course
  • Guest Parking
  • Park
  • Tennis Court(s)

Other published features

  • Multipurpose Room
  • Medical Facility

Questions to confirm with the community

Current age qualification
Confirm with the community
What the HOA includes
Confirm current services and assessments
New-build or resale availability
Individual listings are not tracked here