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

775 South Street
Middlebury, CT $2,850,000

775 South Street

Middlebury, CT

$2,850,000
  • 8 Beds
  • 6/2 Baths
  • 9,619 Sqft
397 White Deer Rock Road
Middlebury, CT $2,195,000

397 White Deer Rock Road

Middlebury, CT

$2,195,000
  • 3 Beds
  • 2/1 Baths
  • 3,863 Sqft
67 Abbott Farms Road
Middlebury, CT $1,399,900

67 Abbott Farms Road

Middlebury, CT

$1,399,900
  • 4 Beds
  • 3/1 Baths
  • 5,237 Sqft
135 Washington Drive
Middlebury, CT $999,000

135 Washington Drive

Middlebury, CT

$999,000
  • 4 Beds
  • 3/1 Baths
  • 3,485 Sqft
294 Christian Road
Middlebury, CT $995,000

294 Christian Road

Middlebury, CT

$995,000
  • 3 Beds
  • 2/1 Baths
  • 2,878 Sqft
9 Whitehall Court
Middlebury, CT $979,900

9 Whitehall Court

Middlebury, CT

$979,900
  • 4 Beds
  • 3/2 Baths
  • 4,261 Sqft
552 Breakneck Hill Road
Middlebury, CT $950,000

552 Breakneck Hill Road

Middlebury, CT

$950,000
  • 5 Beds
  • 3/1 Baths
  • 4,114 Sqft
625 Charcoal Avenue
Middlebury, CT $945,000

625 Charcoal Avenue

Middlebury, CT

$945,000
  • 3 Beds
  • 2/1 Baths
  • 4,236 Sqft

Middlebury

Area Map

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Middlebury

Market Snapshot

Units Sold

August 2026

6 TOTAL UNITS

image description -45.5% image description -45.5% vs

Median Sales Price

August 2026 - Single Family Homes

$515K
image description -2.5% image description +19.8% vs

Percentage of Asking Price

August 2026 Single Family Homes

98%
image description -2.4% image description -2.8% vs
98%
image description -2.4% image description -2.8% vs
98%
image description -2.4% image description -2.8% vs
98%
image description -2.4% image description -2.8% vs