Middlebury, CT Real Estate & Homes For Sale

21 homes

Real Estate & Homes For Sale Near Middlebury, CT

We found 30 more homes matching your filters just outside Middlebury

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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 $552,761
MonthMedian home value
June 2025$540k
July 2025$542k
August 2025$544k
September 2025$547k
October 2025$550k
November 2025$551k
December 2025$553k
January 2026$553k
February 2026$553k
March 2026$554k
April 2026$553k
May 2026$553k
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 6 new listings in Middlebury, CT and 21 homes for sale.
Home SizeHome Value*
2 bedrooms (See homes)$460,173
3 bedrooms (10 homes)$531,304
4 bedrooms (7 homes)$661,505
*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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