SoldJun 15, 2026

Listed by DONNA BANNON

, 

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.

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