Open House 5/2 11am - 1pm
283 Whittemore Road
Middlebury, CT, 06762 $ 529,000
Bedrooms3 Baths2.1 Sq 2,500 Monthly Estimate*
$ 3,257
for $529,000 with 3 bedrooms and 2 full baths, 1 half bath. This 2,500 square foot home was built in 1972 on a lot size of 0.39.
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, 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.
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Open House
5/2/2026 11:00 AM - 1:00 PM
283 Whittemore Road Middlebury, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
Single Family Coming Soon
FeaturesGeneralZoning R40
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 0.39
Directions I-84 to Straits Tpk to Whittemore Rd. Turn onto Shadduck Rd. Driveway is on Shadduck.
High School Per Board of Ed
City Middlebury
Elementary School Per Board of Ed
Sq Ft Total 2500
Year Built 1972
Exclusions Per Inclusions/Exclusions Addendum
Style Raised Ranch
Year Built Source Public Records
Handicap Features Accessible Bath Bath Grab Bars Multiple Entries/Exits
Energy Features Generator Ready
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InteriorCooling System Window Unit
Total Rooms 6
Basement Description Full Heated Fully Finished Garage Access Interior Access Liveable Space Full With Walk-Out
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ExteriorWater Source Private Well
Lot Description Corner Lot Level Lot
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* Excluded FeaturesList ByJennifer SiscoListing Agent
jenrheritage@gmail.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $3,257
- Monthly Property Taxes
- $513
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Middlebury, CT
Average List Price $704,142
Percent of Sale Price 33%
About Middlebury, CT 7,671 Population
18% Since 2002
$ 105,125 Median Income
46.66 Median Age
27% Households with Children
Trends Information provided by ATTOM Data Solutions.
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 4/27/2026 | $529,000 | | Listed Price |