Middlebury

Shoreline, Connecticut

VIEW 94 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 Yale Avenue
Middlebury, CT $449,000

1 Yale Avenue

Middlebury, CT

$449,000
  • 3 Beds
  • 2 Baths
  • 1,788 Sqft
225 Whittemore Road
Middlebury, CT $425,000

225 Whittemore Road

Middlebury, CT

$425,000
  • 3 Beds
  • 1 Baths
  • 1,630 Sqft
122 Mirey Dam Road
Middlebury, CT $1,475,000

122 Mirey Dam Road

Middlebury, CT

$1,475,000
  • 4 Beds
  • 5 Baths
  • 6,175 Sqft
6 White Birch Lane
Middlebury, CT $1,249,500

6 White Birch Lane

Middlebury, CT

$1,249,500
  • 4 Beds
  • 3/1 Baths
  • 3,700 Sqft
7 White Birch Lane
Middlebury, CT $1,099,750

7 White Birch Lane

Middlebury, CT

$1,099,750
  • 4 Beds
  • 3/1 Baths
  • 3,325 Sqft
11 White Birch Lane
Middlebury, CT $999,500

11 White Birch Lane

Middlebury, CT

$999,500
  • 4 Beds
  • 4/1 Baths
  • 3,000 Sqft
4 White Birch Lane
Middlebury, CT $949,500

4 White Birch Lane

Middlebury, CT

$949,500
  • 4 Beds
  • 3/1 Baths
  • 2,750 Sqft
383 Leonard Road
Middlebury, CT $939,000

383 Leonard Road

Middlebury, CT

$939,000
  • 4 Beds
  • 3/1 Baths
  • 3,220 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

June 2025

14 TOTAL UNITS

image description +27.3% image description +40.0% vs

Median Sales Price

June 2025 - Single Family Homes

$590K
image description +0.9% image description +2.2% vs

Percentage of Asking Price

June 2025 Single Family Homes

101%
image description +1.8% image description +4.2% vs
101%
image description +1.8% image description +4.2% vs
101%
image description +1.8% image description +4.2% vs
101%
image description +1.8% image description +4.2% vs
101%
image description +1.8% image description +4.2% vs
Middlebury-CT 1440x806