Middlebury Homes For Sale 

Middlebury

Middlebury boasts a strong sense of community, supported by amenities such as the Middlebury Greenway, a scenic trail repurposed from a former trolley line, and the Larkin State Park Trail, offering opportunities for hiking, biking, and horseback riding. The town's strategic location provides easy access to major highways, the Waterbury-Oxford Airport, and the Metro-North Railroad, facilitating convenient travel to neighboring cities and beyond.

Real Estate Statistics

Average Price	$595K
Lowest Price	$12
Highest Price	$1.5M
Total Listings	92
Avg. Days On Market	101
Avg. Price/SQFT	$264

Property Types (active listings)

Search Middlebury Homes For Sale

• All Listings
• Under $100,000
• $100,000 - $200,000
• $200,000 - $300,000
• $300,000 - $400,000
• $400,000 - $500,000
• $500,000 - $600,000
• $600,000 - $700,000
• $700,000 - $800,000
• $800,000 - $900,000
• $900,000 - $1,000,000
• Over $1,000,000

Bedrooms

Bathrooms

Price Range

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New

$700,000

33 Ridgewood Drive 33, Middlebury

3 Beds 4 Baths 3,432 SqFt Condo/Co-Op For Sale MLS® # 24105460

New

$900,000

87 Falcon Crest Road, Middlebury

4 Beds 3 Baths 3,142 SqFt Single Family For Sale MLS® # 24101514

New

$4,500

77 Crest Road, Middlebury

4 Beds 4 Baths 2,674 SqFt Residential Rental MLS® # 24103854

$539,900

190 Allerton Farms Road, Middlebury

2 Beds 3 Baths 1,744 SqFt Single Family For Sale MLS® # 24101800

$2,900

443 Benson Road, Middlebury

4 Beds 2 Baths 1,766 SqFt Residential Rental MLS® # 24102210

$465,000

1 Yale Avenue, Middlebury

3 Beds 2 Baths 1,788 SqFt Single Family For Sale MLS® # 24101631

$799,000

77 Crest Road, Middlebury

4 Beds 4 Baths 2,674 SqFt Single Family For Sale MLS® # 24101291

$560,753

North Benson Road 52, Middlebury

3 Beds 3 Baths 2,206 SqFt Condo/Co-Op For Sale MLS® # 24100213

$649,900

1 Independence Circle 1, Middlebury

4 Beds 3 Baths 3,224 SqFt Single Family For Sale MLS® # 24100063

$649,900

1 Independence Circle 1, Middlebury

4 Beds 3 Baths 3,224 SqFt Condo/Co-Op For Sale MLS® # 24099988

$509,900

North Benson Road 47, Middlebury

3 Beds 3 Baths 1,950 SqFt Condo/Co-Op For Sale MLS® # 24099635

$799,900

18 Deer Run Road, Middlebury

3 Beds 3 Baths 2,190 SqFt Single Family For Sale MLS® # 24099002

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