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.
For sale
$529,000
283 Whittemore Road, Middlebury, CT 06762
3beds
2,500sqft
Est.:
Single Family Residence
Built in 1972
0.39 Acres Lot
$-- Zestimate®
$212/sqft
$-- HOA
What's special
- 14 days |
- 964 |
- 45 |
Zillow last checked:
Listing updated:
Listed by:
Jennifer Sisco (203)417-5764,
RE/MAX Heritage 203-452-7653
Source: Smart MLS,MLS#: 24169230
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Ceiling Fan(s), Half Bath
- Level: Main
Bedroom
- Features: Ceiling Fan(s)
- Level: Main
Bedroom
- Features: Remodeled, Ceiling Fan(s)
- Level: Lower
Dining room
- Features: Balcony/Deck, Sliders
- Level: Main
Living room
- Features: Hardwood Floor
- Level: Main
Rec play room
- Features: Remodeled, Gas Log Fireplace, Full Bath, Sliders
- Level: Lower
Heating
- Hot Water, Oil
Cooling
- Window Unit(s)
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water Heater, Tankless Water Heater
- Laundry: Lower Level
Features
- Basement: Full,Heated,Finished,Garage Access,Interior Entry,Liveable Space
- Attic: Pull Down Stairs
- Number of fireplaces: 1
Interior area
- Total structure area: 2,500
- Total interior livable area: 2,500 sqft
- Finished area above ground: 1,300
- Finished area below ground: 1,200
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Accessibility
- Accessibility features: Accessible Bath, Bath Grab Bars, Multiple Entries/Exits
Features
- Patio & porch: Porch, Deck, Patio
- Exterior features: Garden, Lighting
- Waterfront features: Walk to Water, Access
Lot
- Size: 0.39 Acres
- Features: Corner Lot, Level
Details
- Additional structures: Shed(s)
- Parcel number: 1193292
- Zoning: R40
- Other equipment: Generator Ready
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter, Raised
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1972
Utilities & green energy
- Sewer: Public Sewer
- Water: Well
Community & HOA
Community
- Features: Golf, Lake, Medical Facilities, Park, Playground, Public Rec Facilities, Near Public Transport, Shopping/Mall
HOA
- Has HOA: No
Location
- Region: Middlebury
Financial & listing details
- Price per square foot: $212/sqft
- Tax assessed value: $189,400
- Annual tax amount: $6,159
- Date on market: 4/27/2026
- Exclusions: Per Inclusions/Exclusions Addendum
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 4/30/2026 | Listed for sale | $529,000+113.7%$212/sqft |
Source:  Smart MLS #24169230 Report a problem | ||
| 2/7/2013 | Sold | $247,500-4.8%$99/sqft |
Source: Smart MLS #W1067854 Report a problem | ||
| 1/4/2013 | Pending sale | $259,900$104/sqft |
Source: Bannon & Hebert Properties, LLC #W1067854 Report a problem | ||
| 7/14/2012 | Price change | $259,900-1.9%$104/sqft |
Source: Bannon & Hebert Properties, LLC #W1067854 Report a problem | ||
| 3/19/2012 | Price change | $265,000-3.6%$106/sqft |
Source: Bannon & Hebert Properties, LLC #W1064471 Report a problem | ||
| 10/30/2011 | Listed for sale | $275,000$110/sqft |
Source: Bannon & Hebert Properties LLC #W1064471 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,159 -0.2% | $189,400 |
| 2024 | $6,174 +1% | $189,400 |
| 2023 | $6,110 +3.2% | $189,400 |
| 2022 | $5,921 +4.2% | $189,400 +16.1% |
| 2021 | $5,684 -0.8% | $163,200 |
| 2020 | $5,728 +5.1% | $163,200 |
| 2019 | $5,451 +2.7% | $163,200 |
| 2018 | $5,306 +3.2% | $163,200 |
| 2017 | $5,139 +10.3% | $163,200 +5.5% |
| 2015 | $4,660 +2.7% | $154,700 |
| 2014 | $4,539 +1.7% | $154,700 |
| 2013 | $4,465 +2.8% | $154,700 |
| 2012 | $4,342 +3.9% | $154,700 -11.9% |
| 2011 | $4,178 +0.7% | $175,600 |
| 2009 | $4,149 +1.8% | $175,600 |
| 2008 | $4,076 +6% | $175,600 |
| 2007 | $3,846 +4.6% | $175,600 +45.9% |
| 2005 | $3,677 -0.9% | $120,350 |
| 2004 | $3,709 +8.2% | $120,350 0% |
| 2003 | $3,429 +4.9% | $120,400 +18% |
| 2000 | $3,269 | $102,000 |
Find assessor info on the county website
Monthly payment
Est. payment
$3,526/mo
Principal & interest
$2587
Property taxes
$939
More affordability tools
Climate risks
Neighborhood: 06762
Nearby schools
GreatSchools rating
- 5/10Middlebury Elementary SchoolGrades: K-5Distance: 0.5 mi
- 7/10Memorial Middle SchoolGrades: 6-8Distance: 1.1 mi
- 8/10Pomperaug Regional High SchoolGrades: 9-12Distance: 4 mi
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Connecticut
- New Haven County
- Middlebury
- 06762
- 283 Whittemore Road
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