283 Whittemore Road

Off Market

283 Whittemore Road

Middlebury CT 06762

2500 sq. ft.

0.39 ac.

Single-Family

Last sold for $500,000

Jennifer Sisco, last sold this property on 18 June 2026 after 49 days on market.

Overview

Thoughtful updates, versatile living space, and an unbeatable location come together at this gorgeous, meticulously maintained Middlebury home which offers the perfect blend of comfort and functionality and a layout designed for both everyday living and gracious entertaining. Freshly painted throughout, the home feels bright, clean, and move-in ready from the moment you step inside. The heart of the home flows from the kitchen and dining area out to a spacious bi-level deck, overlooking a large, flat backyard, ideal for gatherings, play, or simply enjoying peaceful time outdoors. A lovely lower patio creates an additional outdoor living space that feels like your own private retreat. Downstairs, the recently renovated lower level adds exceptional value and flexibility. Finished with upscale touches, this space features a comfortable living area with a luxurious fireplace, a private bedroom, full bathroom, and direct access to both the oversized 2-car garage and the backyard patio through sliding doors. Practical upgrades provide peace of mind and long-term efficiency, including: New roof and leaf guards (2020), Upgraded 200-amp electrical service, New Furnace (2024), Generator hookup (2020), New double-wall 300-gallon oil tank (2020), New well pump and water softener (2025), and hot and cold water supply in garage (2025).

Features

3 bedrooms

3 bathrooms

2 carspaces

2 garage spaces

2500 sq. ft. floor area

0.39 ac. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Middlebury over the last 12 months, the estimated median property value of 283 Whittemore Road is $495k.

Median value

$495k

Estimated value range

$300k - $875k

Median days on market

Estimated value trend

13%

increase 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 283 Whittemore Road

2026

Sold

$500,000

18 Jun 2026 by Jennifer Sisco, of REMAX Heritage | Monroe

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 3 bedroom single-family properties in Middlebury

In the last 12 months, 34 three-bedroom single-family properties similar to 283 Whittemore Road, have been sold.

This represents a 11% increase in three-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

(72 reviews)

Get a market analysis

Lauren Auresto

at BHGRE Gaetano Marra Homes

(7 reviews)

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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