396 E Main St, Middlebury, VT 05753
OFF MARKET

396 E Main St
Middlebury, VT 05753

East Middlebury
  • 4 Beds
  • 3 Baths
  • 3,300 sqft (on 0.40 acres)

$504,900

Trulia Estimate
as of Aug 19, 2026

$504,900

Trulia Estimate
as of Aug 19, 2026
4 Beds
3 Baths
3,300 sqft
(on 0.40 acres)

Home Value

Trulia Estimate
$505K
Since last month
Decreased$40K (-7.7%)
Since last year
Decreased$52K (-9.9%)
Since last sale
Increased$239K (+100%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +140% in the last 10 years
MonthEstimated value
2026
August 2026$479K
July 2026$519K
June 2026$510K
May 2026$499K
April 2026$498K
March 2026$498K
February 2026$493K
January 2026$502K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
427 E Main Street, Middlebury, VT
0.24
Single-Family Home
$432,000
12/23/25
5
2
2,963
82 Ossie Road, Middlebury, VT
0.16
Single-Family Home
$280,000
03/18/26
3
1.5
1,330
86 Ossie Road, Middlebury, VT
0.15
Single-Family Home
$410,000
02/11/26
3
2
1,673
46 Ossie Road, Middlebury, VT
0.39
Single-Family Home
$408,000
03/26/26
3
2.5
1,694
418 East Main Street, Middlebury, VT
0.17
Single-Family Home
$516,000
08/22/25
3
2
1,780
385 East Main Street, Middlebury, VT
0.11
Single-Family Home
$399,000
10/02/25
2
2
1,206
29 Kings Row, Middlebury, VT
0.18
Single-Family Home
$676,767
08/10/26
5
4.5
4,840
72 Daisy Ln, Middlebury, VT
0.62
Single-Family Home
$590,000
06/17/26
4
2.5
2,318
42 Lower Plains Road, Middlebury, VT
0.81
Single-Family Home
$320,000
02/25/26
4
2.5
1,875
44 Lower Plains Road, Middlebury, VT
0.85
Single-Family Home
$372,500
03/20/26
6
3
2,415

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
385 East Main Street, Middlebury, VT 05753
0.11
$416,000
2
2
1,206
Off Market
418 East Main Street, Middlebury, VT 05753
0.17
$539,700
3
2
1,780
Off Market
86 Ossie Road, Middlebury, VT 05753
0.15
$410,000
3
2
1,673
Recently Sold
82 Ossie Road, Middlebury, VT 05753
0.16
$280,000
3
1.5
1,330
Recently Sold
29 Kings Row, Middlebury, VT 05753
0.18
$676,767
5
4.5
4,840
Recently Sold
426 East Main Street, Middlebury, VT 05753
0.23
$508,400
5
2
2,304
Off Market
427 E Main Street, Middlebury, VT 05753
0.24
$432,000
5
2
2,963
Recently Sold
436 East Main Street, Middlebury, VT 05753
0.32
$389,700
3
2
1,558
Off Market
58 Ossie Road, Middlebury, VT 05753
0.30
$454,500
3
2
1,292
Off Market
5 Case Street, Middlebury, VT 05753
0.29
$346,300
3
1
1,144
Off Market
10 Case Street, Middlebury, VT 05753
0.30
$410,000
3
2
1,455
For Sale
55 Ossie Road, Middlebury, VT 05753
0.33
$250,500
2
2
1,068
Off Market

Local Information

  • Map ViewExplore the area around 396 E Main St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1840
Lot Size
0.4 acres
Living Area
3,300 sqft
Price/Sqft
$153

About this House

This single-family home is located at 396 E Main St, Middlebury, VT. 396 E Main St is in the East Middlebury neighborhood in Middlebury, VT and in ZIP code 05753. This property has 4 bedrooms, 3 bathrooms and approximately 3,300 sqft of floor space. This property has a lot size of 0.40 acres and was built in 1840.
396 E Main St, Middlebury, VT 05753 is a 4 bedroom, 3 bathroom, 3,300 sqft single-family home in East Middlebury, built in 1840. It last sold for $239,500 on Aug 11, 2009. It is currently off market. The Trulia Estimate is $504,900, with a rent estimate of $3,693/month.

Home Details for 396 E Main St

Property Information

Year Built
Year Built: 1840Year Updated: 2017
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.40 acres

Price and Tax history

DateEventPrice
Aug 11, 2009
Source: N/A
Sold
$239,500
Jan 4, 1995
Source: N/A
Sold
$111,800

Market trends in Middlebury

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
18
2MoM

Around this home

Neighborhood Overview

East Middlebury
See Local Highlights
Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Frequently asked questions about 396 E Main St

  • What is 396 E Main St estimated to be worth?
    Trulia's estimated value for 396 E Main St in Middlebury, VT is $504,900.
  • What is the price history for 396 E Main St?
    396 E Main St in Middlebury, VT last sold for $239,500 in August 2009.
  • Is Middlebury a buyer's or seller's market?
    Middlebury is currently a balanced market, based on recent for-sale activity.
  • What are the closest schools to 396 E Main St?
    The closest schools to 396 E Main St in Middlebury, VT are Mary Hogan School (Pre-K/Elementary, rated 8/10), Middlebury Senior Uhsd #3 (High, rated 9/10), Middlebury Union Middle School (rated 6/10).
  • How big is the lot at 396 E Main St?
    The lot at 396 E Main St in Middlebury, VT is about 0.40 acres (17,424 sq ft).

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 396 E Main St

Skip to last item
Skip to first item

Homes for sale near 396 E Main St

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item