Middlebury

Shoreline, Connecticut

VIEW 78 COMMUNITY LISTINGS

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

1 Tyler Ridge Drive
Goshen, CT $150,000

1 Tyler Ridge Drive

Goshen, CT

$150,000
  • 5.01 Acres
2 Tyler Ridge Drive
Goshen, CT $150,000

2 Tyler Ridge Drive

Goshen, CT

$150,000
  • 5.12 Acres
775 South Street
Middlebury, CT $2,999,000

775 South Street

Middlebury, CT

$2,999,000
  • 7 Beds
  • 6/2 Baths
  • 9,619 Sqft
40 Winthrop Drive
Unspecified, CT $2,100,000

40 Winthrop Drive

Unspecified, CT

$2,100,000
  • 4 Beds
  • 4/2 Baths
  • 4,954 Sqft
40 Winthrop Drive
Middlebury, CT $2,000,000

40 Winthrop Drive

Middlebury, CT

$2,000,000
  • 4 Beds
  • 4/2 Baths
  • 6,024 Sqft
700 South Street
Middlebury, CT $1,999,900

700 South Street

Middlebury, CT

$1,999,900
  • 5 Beds
  • 5/2 Baths
  • 5,811 Sqft
397 White Deer Rock Road
Middlebury, CT $1,695,000

397 White Deer Rock Road

Middlebury, CT

$1,695,000
  • 3 Beds
  • 2/1 Baths
  • 3,363 Sqft
100 North Benson Road
Middlebury, CT $1,590,000

100 North Benson Road

Middlebury, CT

$1,590,000
  • 5,312 Sqft

Middlebury

Area Map

Middlebury is within Shoreline, Connecticut and borders Woodbury, Watertown and Southbury.

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Featured Communities Within

Shoreline

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Middlebury

Market Snapshot

Units Sold

September 2023

5 TOTAL UNITS

image description -58.3% image description -73.7% vs

Median Sales Price

September 2023 - Single Family Homes

$335K
image description -4.3% image description -2.6% vs

Percentage of Asking Price

September 2023 Single Family Homes

100%
image description +4.1% image description -1.6% vs
100%
image description +4.1% image description -1.6% vs
Middlebury-CT 1440x806