245 Upper Whittemore Road

Off Market

245 Upper Whittemore Road

Middlebury CT 06762

2990 sq. ft.

3.03 ac.

Single-Family

Last sold for $875,000

DONNA BANNON, last sold this property on 15 June 2026 after 56 days on market.

Overview

Enjoy magnificent sunsets from this exceptional home, privately set on just over three acres in one of the area's most desirable locations. The beautifully landscaped grounds offer both open space and a wooded backdrop for added privacy, along with views of a neighboring stone wall. An in-ground heated saltwater pool is surrounded by an expansive patio and charming pergola-perfect for outdoor entertaining. Three garages are conveniently accessible from both the upper and lower driveways. Inside, the home features 2,990 square feet of thoughtfully designed living space with custom touches throughout. The spacious kitchen includes a dining area, breakfast bar, and a 36" GE Monogram dual-fuel range, offering ample space for cooking and gathering. The adjoining 23' x 20' family room provides a welcoming setting, a propane fired custom fireplace and overlooks the scenic rear property. The primary suite features a walk-in closet, an additional closet, and an updated full bath. The main level is completed by a formal dining room, private office/library, powder room, and laundry area. Upstairs, you'll find two additional bedrooms, a full bath, and a flexible guest area and lots of room for expansion. Additional highlights include the lush grounds, patio, heated saltwater pool, pergola, and more.

Features

3 bedrooms

3 bathrooms

8 carspaces

3 garage spaces

2990 sq. ft. floor area

3.03 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 245 Upper Whittemore Road is $492.5k.

Median value

$492.5k

Estimated value range

$300k - $875k

Median days on market

Estimated value trend

11%

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 245 Upper Whittemore Road

2026

Sold

$875,000

15 Jun 2026 by DONNA BANNON, of BHGRE Bannon & Hebert

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 245 Upper Whittemore Road, have been sold.

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

(70 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