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).
Just a couple of minutes to I-84, commuting is a breeze, while outdoor enthusiasts will love being only half a mile from Hop Brook Lake, offering year-round recreation including swimming, fishing, hiking, mountain biking, camping, canoeing, and cross-country skiing. All of this, plus the added benefit of significantly lower taxes compared to neighboring towns, makes this property an exceptional opportunity.
Est. $2,226 per month, based on comparable rentals
Sale and tax history for 283 Whittemore Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24169230
Jun 18, 2026
Listing Removed
—
Jun 18, 2026
Sold
$500,000
$200/sq ft
Jun 6, 2026
Pending
—
May 24, 2026
Contingent
—
May 13, 2026
Price Changed
$519,000
$208/sq ft
Apr 30, 2026
Listed
$529,000
$212/sq ft
Apr 27, 2026
Coming Soon
$529,000
$212/sq ft
Smart MLS #W1067854
Feb 7, 2013
Sold
$247,500
$99/sq ft
Jul 12, 2012
Listed
$259,900
$104/sq ft
Impeccable 3 br home on lovely lot in great commuting location. Features spacious lr open to dr, kitchen with breakfast bar, family room w/ fp on walk out level. Office & laundry on walk out level. Lovely grounds.New mill rate: 28.07. Taxes: $4342.43. Room off master bedroom can easily be 3rd bedroom on that level.