Middlebury

The town of Middlebury is a premier Connecticut hamlet in New Haven County known for its scenic beauty, friendliness and rural warmth.

Incorporated in 1807 from former Southbury, Woodbury and Waterbury lands, the town of Middlebury in New Haven County took its name from its proximity to its neighboring communities. Home to the private Westover School for girls and the historic Quassy Amusement Park, one of the nation’s oldest amusement parks in operation, Middlebury’s town leaders continuously strive to maintain a high standard of living for residents and a welcoming and rewarding experience for visitors.
The 18.5 square mile town is home to 6,450 residents who take pride in the community’s history and its plethora of parks and preserved lands offering quiet relaxation and a multitude of opportunities for recreation and tranquil getaways. A popular destination is the vast and scenic, the state-owned Larkin Park State Trail. A long and narrow linear trail stretches across four towns, including Middlebury, and is a popular destination for walkers, bikers, hikers and joggers. During the winter months, the trail is ideal for cross-country skiing.
An active Chamber of Commerce comprising local businesses promotes the town’s economic development. Residents of this Connecticut town know and appreciate small-town living at its finest.

Incorporated in 1807 from former Southbury, Woodbury and Waterbury lands, the town of Middlebury in New Haven County took its name from its proximity to its neighboring communities. Home to the private Westover School for girls and the historic Quassy Amusement Park, one of the nation’s oldest amusement parks in operation, Middlebury’s town leaders continuously strive to maintain a high standard of living for residents and a welcoming and rewarding experience for visitors.
The 18.5 square mile town is home to 6,450 residents who take pride in the community’s history and its plethora of parks and preserved lands offering quiet relaxation and a multitude of opportunities for recreation and tranquil getaways. A popular destination is the vast and scenic, the state-owned Larkin Park State Trail. A long and narrow linear trail stretches across four towns, including Middlebury, and is a popular destination for walkers, bikers, hikers and joggers. During the winter months, the trail is ideal for cross-country skiing.
An active Chamber of Commerce comprising local businesses promotes the town’s economic development. Residents of this Connecticut town know and appreciate small-town living at its finest.

Incorporated in 1807 from former Southbury, Woodbury and Waterbury lands, the town of Middlebury in New Haven County took its name from its proximity to its neighboring communities. Home to the private Westover School for girls and the historic Quassy Amusement Park, one of the nation’s oldest amusement parks in operation, Middlebury’s town leaders continuously strive to maintain a high standard of living for residents and a welcoming and rewarding experience for visitors.
The 18.5 square mile town is home to 6,450 residents who take pride in the community’s history and its plethora of parks and preserved lands offering quiet relaxation and a multitude of opportunities for recreation and tranquil getaways. A popular destination is the vast and scenic, the state-owned Larkin Park State Trail. A long and narrow linear trail stretches across four towns, including Middlebury, and is a popular destination for walkers, bikers, hikers and joggers. During the winter months, the trail is ideal for cross-country skiing.
An active Chamber of Commerce comprising local businesses promotes the town’s economic development. Residents of this Connecticut town know and appreciate small-town living at its finest.

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Featured Listings

106 Judd Hill Road
Middlebury, CT $1,219,900

106 Judd Hill Road

Middlebury, CT

$1,219,900
  • 4 Beds
  • 3/1 Baths
  • 4,696 Sqft
45 East Farm Road
Middlebury, CT $1,150,000

45 East Farm Road

Middlebury, CT

$1,150,000
  • 4 Beds
  • 4/2 Baths
  • 5,054 Sqft
593 Park Road Extension
Middlebury, CT $995,000

593 Park Road Extension

Middlebury, CT

$995,000
  • 4 Beds
  • 3/1 Baths
  • 4,496 Sqft
Lot 6 White Birch Drive
Middlebury, CT $899,950

Lot 6 White Birch Drive

Middlebury, CT

$899,950
  • 4 Beds
  • 3/1 Baths
  • 3,100 Sqft
294 Christian Road
Middlebury, CT $899,000

294 Christian Road

Middlebury, CT

$899,000
  • 3 Beds
  • 2/1 Baths
  • 2,878 Sqft
22 Somerset Drive
Middlebury, CT $899,000

22 Somerset Drive

Middlebury, CT

$899,000
  • 3 Beds
  • 2/1 Baths
  • 2,878 Sqft
11 Hunting Ridge Road
Middlebury, CT $799,900

11 Hunting Ridge Road

Middlebury, CT

$799,900
  • 4 Beds
  • 2/1 Baths
  • 2,700 Sqft
18 Hunting Ridge Road
Middlebury, CT $799,900

18 Hunting Ridge Road

Middlebury, CT

$799,900
  • 4 Beds
  • 2/1 Baths
  • 2,700 Sqft

Middlebury

Area Map

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Middlebury

Market Snapshot

Units Sold

March 2025

15 TOTAL UNITS

image description +114.3% image description +114.3% vs

Median Sales Price

March 2025 - Single Family Homes

$421K
image description -19.8% image description -0.9% vs

Percentage of Asking Price

March 2025 Single Family Homes

100%
image description +8.5% image description +1.4% vs
100%
image description +8.5% image description +1.4% vs
100%
image description +8.5% image description +1.4% vs
100%
image description +8.5% image description +1.4% vs
100%
image description +8.5% image description +1.4% vs