53 High Street, Middlebury, VT, 05753 | $275,000

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!

Features

  • Rooms: 8
  • Bedrooms: 3
  • Baths: 3 full
  • Style: Colonial,Duplex,Tri-Level,Walkout Lower Level
  • Year Built: 1920
  • Heating: Baseboard,Electric
  • Cooling: Wall AC Units
  • Basement: Full
  • Approx Sq. Feet: 1,740
  • Acreage: 0.29
  • Est. Taxes: $7,056
  • Lot Desc: Country Setting,Hilly,Mountain View,Open,Sloping,Trail/Near Trail,View
  • Elem. School: Mary Hogan School
  • Middle School: Middlebury Union Middle #3
  • High School: Middlebury Senior UHSD #3
  • School District: Addison Central
  • MLS#: 5045832
  • Website: https://www.raveis.com
    /prop/5045832/53highstreet_middlebury_vt?source=qrflyer
©2026 New England Real Estate Network, Inc. All rights reserved.This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimMLS. 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 1/29/2026

William Raveis Family of Services

Our family of companies partner in delivering quality services in a one-stop-shopping environment. Together, we integrate the most comprehensive real estate, mortgage and insurance services available to fulfill your specific real estate needs.

Toni TiceLuxury Properties Specialist

203.257.9647

Toni.Tice@raveis.com

Our family of companies offer our clients a new level of full-service real estate. We shall:

  • Market your home to realize a quick sale at the best possible price
  • Place up to 20+ photos of your home on our website, raveis.com
  • Provide frequent communication and tracking reports showing the Internet views your home received on raveis.com
  • Showcase your home on raveis.com with a larger and more prominent format
  • Give you the full resources and strength of William Raveis Real Estate, Mortgage & Insurance and our cutting-edge technology

To learn more about our credentials, visit raveis.com today.

Christine PrestonVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 90874

203.521.7207

Christine.Preston@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
  • Is in constant contact with a full processing, underwriting, and closing staff to ensure an efficient transaction

Rosemarie DePasqualeInsurance Sales Director, William Raveis Insurance

203.561.0013

Rosemarie.DePasquale@raveis.com

Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
  • Offers full-service coverage such as Homeowner's, Auto, Life, Renter's, Flood and Valuable Items
  • Partners with major insurance companies including Chubb, Kemper Unitrin, The Hartford, Progressive,
    Encompass, Travelers, Fireman's Fund, Middleoak Mutual, One Beacon and American Reliable

53 High Street, Middlebury, VT, 05753

$275,000

Toni Tice

Luxury Properties Specialist

William Raveis Real Estate

Phone: 203.257.9647

Toni.Tice@raveis.com

Christine Preston

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 203.521.7207

Christine.Preston@raveis.com

NMLS Mortgage Loan Originator ID 90874

5/6 (30 Yr)
Adjustable Rate Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $220,000 $220,000 $220,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 5.990% 5.375%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.209% 6.168% 5.609%
Monthly Tax Payment $588 $588 $588
H/O Insurance Payment $75 $75 $75
Initial Principal & Interest Pmt $1,249 $1,318 $1,783
Total Monthly Payment $1,912 $1,981 $2,446

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.