Middlebury, VT

Homes for Sale Under $500K in Middlebury, VT

15Results

Middlebury single-family homes listed at $500,000 or less are one of the most searched price ranges on our site. See all homes for sale in Middlebury, create a free account to save this search and receive alerts, or call Greentree Real Estate at (802) 453-5232 to speak with an agent.

Newest
Active Under Contract
32 Barnes Brook Road Middlebury VT 05753

$499,000

Middlebury, VT

32 Barnes Brook Road, Unit 10.3

  • 3 Beds
  • 3 Baths
  • 1,938 SqFt
  • 36 Days on Market
MLS#: 5108296
Active Under Contract

$495,000

Middlebury, VT

5 Swanage Court

  • 3 Beds
  • 2 Baths
  • 0.6 Acres
  • 1,764 SqFt
  • 36 Days on Market
MLS#: 5108261

$429,000

Middlebury, VT

17 Forest Ridge Road

  • 2 Beds
  • 2 Baths
  • 2.21 Acres
  • 1,844 SqFt
  • 37 Days on Market
MLS#: 5108105

$225,000

Middlebury, VT

51 Ossie Road

  • 0.29 Acres
  • 2,088 SqFt
  • 58 Days on Market
MLS#: 5104820

$385,000

Middlebury, VT

10 Case Street

  • 3 Beds
  • 2 Baths
  • 1.24 Acre
  • 1,455 SqFt
  • 61 Days on Market
MLS#: 5104160
Active Under Contract

$499,000

Middlebury, VT

88 Brush Lane, Unit 10.8

  • 3 Beds
  • 3 Baths
  • 1,938 SqFt
  • 64 Days on Market
MLS#: 5104010

$475,000

Middlebury, VT

35 North Leno Lane Extension

  • 2 Beds
  • 2 Baths
  • 10.19 Acres
  • 1,472 SqFt
  • 68 Days on Market
MLS#: 5103079

$379,000

Middlebury, VT

118 Three Mile Bridge Road

  • 3 Beds
  • 2 Baths
  • 1.1 Acre
  • 2,232 SqFt
  • 73 Days on Market
MLS#: 5102314
Active Under Contract

$499,000

Middlebury, VT

44 Barnes Brook Road, Unit 10.1

  • 3 Beds
  • 3 Baths
  • 1,938 SqFt
  • 75 Days on Market
MLS#: 5101838

$499,000

Middlebury, VT

86 Brush Lane, Unit 10.7

  • 3 Beds
  • 3 Baths
  • 1,938 SqFt
  • 82 Days on Market
MLS#: 5100817

$280,000

Middlebury, VT

89 Court Street

  • 4 Beds
  • 2 Baths
  • 0.25 Acres
  • 1,344 SqFt
  • 87 Days on Market
MLS#: 5099999

$470,000

Middlebury, VT

95 Seminary Street Extension

  • 3 Beds
  • 2 Baths
  • 1.1 Acre
  • 1,916 SqFt
  • 137 Days on Market
MLS#: 5090864

Middlebury, VT Houses Listed Under $500,000

Homes in this range turn up in Middlebury's in-town neighborhoods off Court Street and Washington Street, along with capes and ranches on the roads leading out toward East Middlebury, Weybridge and Cornwall. Many offer yard space and views of the surrounding farmland, and downtown, the college and Otter Creek are a short drive or walk away. This search lists every single-family house in Middlebury listed at $500,000 or below, and it updates as homes come on the market. Greentree Real Estate knows Addison County well. Compare three-bedroom homes in Middlebury or browse homes for sale in Vergennes.

Frequently Asked Questions

Where are homes under $500K found in Middlebury?
Listings appear in neighborhoods near downtown and along the roads toward East Middlebury, Weybridge and Cornwall.
How do I get alerts for new Middlebury listings in this range?
Create a free account to save this search and receive email alerts when new homes are listed at $500,000 or less.
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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 10, 2026 8:23 AM EDT