399 E Main St, Middlebury, VT 05753
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Property image
OFF MARKET

399 E Main St
Middlebury, VT 05753

East Middlebury
  • 6 Beds
  • 3 Baths
  • 3,000 sqft (on 0.50 acres)

$513,200

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $3,385/mo*
Refinance Your Home

$513,200

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $3,385/mo*
Refinance Your Home
6 Beds
3 Baths
3,000 sqft
(on 0.50 acres)

Local Information

  • Map ViewExplore the area around 399 E Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

(3 BR, 2 BR, 1 BR) Owner/Occupy multi family apartment building with 1 car garage, storage barn. In quintessential Vermont college town. 5 minute drive to Middlebury and Middlebury College. Enjoy all the Green Mountains have to offer in your back yard (hiking, skiing, fishing). 2 minute walk to historic Wayburry Inn restaurant and pub (https://wayburyinn.com/). A great investment. Use monthly cash flow from tenants to pay your mortgage and build equity. Take advantage of historically low interest rates in a well maintained, low maintenance, great rental history property. Current rental rates are below the market and can be raised to increase cash flow. $3,300 could go to $3,700.


399 E Main St, Middlebury, VT 05753 is a 6 bedroom, 3 bathroom, 3,000 sqft multi-family in East Middlebury, built in 1960. It last sold for $349,000 on Nov 9, 2020. More recently, it was listed as a rental in April 2018 with an asking price of $950 per month. That rental listing was removed on May 22, 2018. It is currently off market. The Trulia Estimate is $513,200, with a rent estimate of $1,834/month.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 399 E Main St

Property Information

Year Built
Year Built: 1960
Property Type / Style
Property Type: Multi Family

Lot Information

Lot Area: 0.50 acres

Price History for 399 E Main St

DatePriceEventSource
11/09/2020$349,000Sold
N/A
07/15/2020$349,000Listed For SaleN/A
05/22/2018$950ListingRemovedN/A
04/20/2018$950Listed For RentN/A
05/07/2013$230,000Sold
N/A

Market trends in Middlebury

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
14
8MoM
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Property Tax and Assessment

Year2024
Tax
Assessment$284,800
Home facts updated by county records

Comparable Sales for 399 E Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
60-62 E Main St, Middlebury, VT
0.26
Multi-Family Home
$597,500
09/05/25
3
4,506
237 Upper Plains Road, Salisbury, VT
3.45
Multi-Family Home
$345,000
12/03/25
7
2
2,544
62 Court Street, Middlebury, VT
3.97
Multi-Family Home
$420,000
09/12/25
3
1
2,352
29 North Pleasant Street, Middlebury, VT
4.40
Multi-Family Home
$595,000
03/18/26
4
2
2,870
53 High Street, Middlebury, VT
4.63
Multi-Family Home
$250,000
06/11/26
3
3
1,740
29 Middle Seymour Street, Middlebury, VT
4.66
Multi-Family Home
$600,000
12/19/25
4
1.5
2,257

Nearby homes

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Assigned Schools

These are the assigned schools for 399 E Main St.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

East Middlebury
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Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 399 E Main St

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Off Market Homes Near 399 E Main St

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