Recently Sold East Middlebury, VT Homes

$410,000 Sold Feb 11, 2026

86 Ossie Rd, Middlebury, VT 05753

• 3 Beds
• 2 Baths
• 1,673 Sq Ft
• Built 1933

Last Sold Summary

• 2% Below List Price
• $245/SF
• 70 Days On Market

Current Estimated Value $412,434

Last Listing Agent Amey Ryan IPJ Real Estate

$240,000 Sold Sep 19, 2025

55 Ossie Rd, Middlebury, VT 05753

• 2 Beds
• 2 Baths
• 1,068 Sq Ft
• Built 2000

Last Sold Summary

• $225/SF
• 1 Day On Market

Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC

$399,000 Sold Oct 02, 2025

385 E Main St, Middlebury, VT 05753

• 2 Beds
• 2 Baths
• 1,206 Sq Ft
• Built 1900

Last Sold Summary

• 5% Below List Price
• $331/SF
• 42 Days On Market

Current Estimated Value $356,529

Last Listing Agent Sarah Peluso IPJ Real Estate

$432,000 Sold Dec 23, 2025

427 E Main St, Middlebury, VT 05753

• 5 Beds
• 2 Baths
• 2,963 Sq Ft
• Built 1800

Last Sold Summary

• 23% Below List Price
• $146/SF
• 167 Days On Market

Current Estimated Value $477,241

Last Listing Agent Levi Doria IPJ Real Estate

$516,000 Sold Aug 22, 2025

418 E Main St, Middlebury, VT 05753

• 3 Beds
• 2 Baths
• 1,780 Sq Ft
• Built 1800

Last Sold Summary

• 4% Above List Price
• $290/SF
• 5 Days On Market

Current Estimated Value $523,672

Last Listing Agent Jill Fraga The Real Estate Company of Vermont, LLC

$413,000 Sold Aug 08, 2025

45 Ossie Rd, Middlebury, VT 05753

• 3 Beds
• 2 Baths
• 2,185 Sq Ft
• Built 1955

Last Sold Summary

• 6% Above List Price
• $189/SF
• 4 Days On Market

Current Estimated Value $425,135

Last Listing Agent Beth Stanway IPJ Real Estate

$360,000 Sold Mar 12, 2025

3318 U S 7, Middlebury, VT 05753

• 5 Beds
• 3 Baths
• 2,788 Sq Ft
• Built 1880

Last Sold Summary

• 1% Below List Price
• $129/SF
• 17 Days On Market

Last Listing Agent Roxanna Emilo Emilo Real Estate, LLC

$305,000 Sold Aug 14, 2025

24 School House Hill Rd, Middlebury, VT 05753

• 3 Beds
• 2.5 Baths
• 1,584 Sq Ft
• Built 1999

Last Sold Summary

• 2% Above List Price
• $193/SF
• 2 Days On Market

Last Listing Agent Heather Morse Coldwell Banker Hickok and Boardman

$460,000 Sold Aug 12, 2025

37 School House Hill Rd, Middlebury, VT 05753

• 4 Beds
• 2 Baths
• 1,500 Sq Ft
• Built 1967

Last Sold Summary

• $307/SF
• 2 Days On Market

Current Estimated Value $467,420

Last Listing Agent The Malley Group KW Vermont