SoldJun 15, 2026

Bought with Shelley Drakeley from Drakeley Real Estate, Inc.

Source: SmartMLS Connecticut #24167463

245 Upper Whittemore Road, Middlebury, CT, 06762

$875,000

3
3
8
2990 sq. ft.
3.03 ac.

SingleFam

1 day on the market

Sold: Jun 15, 2026

What's around 245 Upper Whittemore Road

About this property

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.

Looking for more information on 245 Upper Whittemore Road?

Explore comparables, sales history and growth for this property.
Learn more

Similar properties sold nearby

SoldJun 18, 2026
$500,000
283 Whittemore Road
Middlebury CT 06762
3
3
2
Single-Family
Listing courtesy of REMAX Heritage | Monroe and Better Living Realty, LLC
SoldMay 29, 2026
$444,000
863 Whittemore Rd
New Haven County CT 06762
3
2
1
Single-Family
Listing courtesy of West View Properties, LLC and William Raveis Real Estate
SoldMay 29, 2026
$300,000
314 Porter Avenue
Middlebury CT 06762
3
2
Single-Family
Listing courtesy of Coldwell Banker Realty and YellowBrick Real Estate LLC

Other properties sold by Shelley Drakeley

SoldJun 2, 2026
$530,000
58 Steele Brook Road
Watertown CT 06795
4
2
1
Single-Family
Listing courtesy of Drakeley Real Estate, Inc. and Burns Realty
SoldDec 15, 2025
$785,000
24 Riverwalk
Branford CT 06405
2
3
2
Single-Family
Listing courtesy of Drakeley Real Estate, Inc. and Coldwell Banker Realty
SoldAug 7, 2025
$1,825,000
44 South St
Litchfield County CT 06783
3
4
3
Single-Family
Listing courtesy of William Pitt Sotheby's Int'l and Drakeley Real Estate, Inc.

Browse properties sold in nearby areas

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the "DMCA") provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under MLS GRID IDX Rules Updated September 16, 2024 7 U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to: dmca@ratemyagent.com

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner's behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Email
© 2026 RateMyAgent