Middlebury, CT Real Estate & Homes For Sale

30 homes

Real Estate & Homes For Sale Near Middlebury, CT

We found 30 more homes matching your filters just outside Middlebury

Middlebury, CT Real Estate Trends

Learn about the Middlebury, CT housing market through trends and averages.

Affordability of Living in Middlebury, CT

The median home value is $541,789
MonthMedian home value
November 2025$536k
December 2025$537k
January 2026$538k
February 2026$538k
March 2026$538k
April 2026$538k
May 2026$545k
June 2026$538k
July 2026$538k
August 2026$539k
September 2026$540k
October 2026$542k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Middlebury, CT, by Home Size

Currently, there are 2 new listings in Middlebury, CT and 30 homes for sale.
Home SizeHome Value*
2 bedrooms (2 homes)$449,272
3 bedrooms (11 homes)$521,557
4 bedrooms (10 homes)$649,525
*Home value over the past month

What Locals Say about Middlebury

  • Ginacea313@gmail.com
    "It’s a beautiful community with little to no crime. There is a crystal clear lake and a small amusement park. Additionally, there are plenty of hiking trails. Autumn is quite amazing here, with many vibrant colors. "
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  • Ginacea313@gmail.com
    "Middlebury is a beautiful town. It is truly a New England gem. Lake Quassapaug is clean and the MRA is well kept. Summers are heavenly here. "
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  • Plandusky
    "Region 15 public schools are some of the best in the state. Middlebury, Southbury public schools. Safe neighborhoods lived here 27 years and could have left the car unlocked the whole time"
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  • Cadecres
    "I’ve lived here 11 years now and everyone is friendly and thoughtful. This town is a hidden gem, just far enough away from the bustle yet close enough not to be isolated."
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  • darrenwittko
    "With excellent schools and beautiful parks, Middlebury is the perfect family community. Close to I-84, it's great for commuters too."
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  • Donathom1114
    "This is an excellent community for families. Top notch schools with excellent family activities. Private community with walking trails and child and pet friendly streets. Wonderful neighbors and pride of home ownership,"
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  • castaway45
    "I grew up here, moved here when I was 9. Many fond memories. Great place to walk and for recreation, and for kids to play, points were neighbors, community spirit, natural setting."
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  • Rtfa50
    "Great neighborhood for a family with children. Close proximity to I-84 both east and westbound. Excellent area for biking, hiking and walking. Easy access to neighboring towns such as Woodbury, Southbury and easy commute for professionals working in both Waterbury or Danbury. "
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  • Hallie
    "I have lived here for 10 years and would not live anywhere else. The schools are fantastic, the parks beautiful, and the town beach perfect. Everywhere you look are flowers, towering oaks, and wonderful jogging paths. This is quintessential New England."
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.