555 Whittemore Road

Off Market

555 Whittemore Road

Middlebury CT 06762

1855 sq. ft.

0.34 ac.

Single-Family

Last sold for $340,000

Deb Smolley, last sold this property on 10 September 2026 after 66 days on market.

Overview

Welcome to this charming Cape Cod home, situated on a 0.34-acre corner lot in the highly desirable town of Middlebury. This home offers 1,855 square feet of comfortable living space with 4 bedrooms and 2.5 baths. The heart of the home features updated oversized country kitchen, with cabinets galore, stainless steel refrigerator, dishwaher and microwave and a gas range. Formal Living Room and Formal Dining Room for your gatherings and entertaining. Newer windows, doors. Remodeled and updated bathrooms. First floor laundry room and bedroom for your convenience. Also, an in-law apartment provides added flexibility for extended family, guests, or potential rental income. The in-law was originally the two car garage that can be converted back! Enjoy all that Middlebury has to offer, including its small-town charm, highly rated schools, wonderful parks, popular restaurants, lake, tennis courts,health club, walking and riding trails, health club and convenient access to Route 8 and I-84.

Features

4 bedrooms

3 bathrooms

3 carspaces

1855 sq. ft. floor area

0.34 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Middlebury over the last 12 months, the estimated median property value of 555 Whittemore Road is $632.5k.

Median value

$632.5k

Estimated value range

$245k - $975k

Median days on market

Estimated value trend

-4%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Middlebury. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 555 Whittemore Road

2026

Sold

$340,000

10 Sep 2026 by Deb Smolley, of DAVE JONES REALTY, LLC

Happy sellers in Middlebury

We have insufficient information to provide an overview of customer satisfaction for Middlebury. Viewing the agent profiles, reviews and sales for Middlebury can provide insights for this location.

Local market activity for 4 bedroom single-family properties in Middlebury

In the last 12 months, 25 four-bedroom single-family properties similar to 555 Whittemore Road, have been sold.

This represents a 25% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Middlebury for a market analysis.

Ken Demirs

at Regency Real Estate, LLC

(74 reviews)

Get a market analysis

Lauren Auresto

at BHGRE Gaetano Marra Homes

(7 reviews)

Get a market analysis

Jay Irvine

at Showcase Realty, Inc.

(1 review)

Get a market analysis

Christina Zainc

at BHGRE Bannon & Hebert

(15 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Middlebury

Ken Demirs

Sellers who recommend Ken Demirs have praised them for being local expert, clear communication, responsive, reliable, dedicated, patient, and supportive