Attention Buyers!! Investors, Multi-generational living, first time home buyers! HUGE Price Reduction! Great Location! This is a great opportunity to build "Sweat Equity" ! Inside you will find 2 one bedroom apartments and a third floor that needs a full rehab. The town only recognizes the lower two floors. Wonderful views and sunsets from all 3 floors looking West over Middlebury proper and the Adirondacks. A short distance to groceries and the Co-op and Chipman Hill Park is a few hundred feet away! Lots of beautiful trees were planted above the house by the current owners including 2 walnut trees, pinyon pines and a willow tree. There is enough room for terraced gardening in the back yard. Bring your imagination and see what this house has to offer in this amazing location in Middlebury!
Active
Listed by: RE/MAX North Professionals, Middlebury
Price cut: $50K (1/27)
$275,000
53 High Street, Middlebury, VT 05753
3beds
1,740sqft
Est.:
Duplex
Built in 1920
-- sqft lot
$-- Zestimate®
$158/sqft
$-- HOA
What's special
- 287 days |
- 1,861 |
- 32 |
Zillow last checked: 7 hours ago
Listing updated: February 15, 2026 at 09:15pm
Listed by:
Bonnie Gridley,
RE/MAX North Professionals, Middlebury 802-388-0505,
Judith W Murdock,
RE/MAX North Professionals, Middlebury
Source: PrimeMLS,MLS#: 5045832
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
Heating
- Baseboard, Electric
Cooling
- Wall Unit(s)
Appliances
- Included: Electric Range, Refrigerator, Electric Water Heater
- Laundry: 2nd Floor Laundry
Features
- Kitchen/Dining, Natural Light
- Flooring: Carpet, Vinyl, Vinyl Plank
- Windows: Double Pane Windows
- Basement: Full,Walk-Out Access
Interior area
- Total structure area: 2,186
- Total interior livable area: 1,740 sqft
- Finished area above ground: 1,740
- Finished area below ground: 0
Property
Parking
- Parking features: Dirt, Driveway, Unpaved
- Has uncovered spaces: Yes
Accessibility
- Accessibility features: 1st Floor Bedroom, 1st Floor Full Bathroom, Hard Surface Flooring
Features
- Levels: 2.5,Tri-Level,Walkout Lower Level
- Stories: 2.5
- Patio & porch: Covered Porch
- Exterior features: Deck, Shed
- Has view: Yes
- View description: Mountain(s)
- Frontage length: Road frontage: 65
Lot
- Size: 0.29 Acres
- Features: Country Setting, Hilly, Open Lot, Sloped, Trail/Near Trail, Views
Details
- Parcel number: 38712012605
- Zoning description: RES
Construction
Type & style
- Home type: MultiFamily
- Architectural style: Colonial
- Property subtype: Duplex
Materials
- Wood Frame, Vinyl Siding
- Foundation: Concrete, Poured Concrete
- Roof: Shingle
Condition
- New construction: No
- Year built: 1920
Utilities & green energy
- Electric: 100 Amp Service, Circuit Breakers
- Sewer: Public Sewer
- Utilities for property: Cable
Community & HOA
Community
- Security: Smoke Detector(s)
Location
- Region: Middlebury
Financial & listing details
- Price per square foot: $158/sqft
- Tax assessed value: $250,900
- Annual tax amount: $7,055
- Date on market: 6/11/2025
- Road surface type: Paved
Estimated market value
Not available
Estimated sales range
Not available
$1,999/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 1/27/2026 | Price change | $275,000-15.4%$158/sqft |
Source:  PrimeMLS #5045832 Report a problem | ||
| 9/15/2025 | Price change | $325,000-3%$187/sqft |
Source: PrimeMLS #5045832 Report a problem | ||
| 8/27/2025 | Price change | $335,000-4.3%$193/sqft |
Source: PrimeMLS #5045832 Report a problem | ||
| 6/11/2025 | Listed for sale | $350,000+138.1%$201/sqft |
Source: PrimeMLS #5045832 Report a problem | ||
| 12/3/2007 | Sold | $147,000$84/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | -- | $250,900 |
| 2023 | -- | $250,900 |
| 2022 | -- | $250,900 |
| 2021 | -- | $250,900 |
| 2020 | -- | $250,900 |
| 2019 | -- | $250,900 +26% |
| 2018 | -- | $199,200 |
| 2017 | -- | $199,200 |
| 2016 | -- | $199,200 +9900% |
| 2015 | -- | $1,992 |
| 2014 | -- | $1,992 |
| 2013 | -- | $1,992 |
| 2012 | -- | $1,992 |
| 2011 | -- | $1,992 |
| 2010 | -- | $1,992 |
| 2009 | -- | $1,992 |
| 2008 | -- | $1,992 |
| 2007 | -- | $1,992 |
| 2006 | -- | $1,992 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$1,805/mo
Principal & interest
$1418
Property taxes
$387
More affordability tools
Climate risks
Neighborhood: 05753
Getting around
55 / 100
Somewhat WalkableNearby schools
GreatSchools rating
- 7/10Middlebury Id #4 SchoolGrades: PK-5Distance: 0.8 mi
- 6/10Middlebury Union Middle SchoolGrades: 6-8Distance: 1.7 mi
- 9/10Middlebury Senior Uhsd #3Grades: 9-12Distance: 1.1 mi
Schools provided by the listing agent
- Elementary: Mary Hogan School
- Middle: Middlebury Union Middle #3
- High: Middlebury Senior UHSD #3
- District: Addison Central
Source: PrimeMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 05753
- Vermont
- Addison County
- Middlebury
- 05753
- 53 High Street
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