783 Whittemore Road
Middlebury, Connecticut 06762
- Beds
- 5
- Baths
- 3
- SqFt
- 3,728
- Acres
- 1.04
- Year Built
- 1953
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
At 783 Whittemore Road, beautifully detailed living spaces are paired with something rarely found in a residential property: an expansive garage with room for far more than everyday parking. Extensively rebuilt in 2010, this Middlebury home offers five bedrooms, three full baths, and remarkable flexibility across its living and utility spaces. Beneath the main living level, the multi-vehicle garage offers substantial room for automobile collections, restoration projects, recreational equipment, and a personal workshop. It's a defining feature for a property where practicality and distinctive design share equal billing. Upstairs, vaulted ceilings, exposed beams, skylights, and blue and green zinc paneling lend architectural character throughout. The kitchen features solid wood cabinetry, a professional gas range, French-door wall oven, convection oven, dual Sub-Zero refrigerators, a separate freezer, and two dishwashers, opening to the dining and family rooms. Radiant-heated hardwood floors distinguish the family room. The primary suite includes a sitting area, two walk-in closets, and a bath with heated floors, soaking tub, oversized shower, and heated towel bars. Additional rooms provide flexibility for living or working, complemented by built-in storage and dedicated laundry. A distinctive combination of craftsmanship, comfortable living, and exceptional space for the things that matter beyond the front door.
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch,Hi-Ranch
- Year Built
- 1953
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 3,728 sq ft
- Lot Size
- 1.04 acres
- Garage / Parking
- 5 garage · 12 total
- Property Taxes
- $13,428 / Annually
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
25
21 under contract
Median List Price
$670,000
25 active listings
Median Closed Price
$540,000
79 sales
Median Days on Market
46
25 active listings
Median $ / Sq Ft
$280
25 active listings
Sale-to-List Ratio
100.0%
79 sales
How this home compares
List Price
$725,000
vs $670,000 median
8.2% above median
Price / Sq Ft
$194
vs $280 median
30.7% below median
Days on Market
0 days
vs 46 days median
46 days fresher than median
Based on 25 active and 79 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of October 13, 2026.
Location
783 Whittemore Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$4,016
- Property Taxes$1,119
- Insurance$242
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middlebury
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Ranch,Hi-Ranch
- Year Built
- 1953
- New Construction
- No/Resale
- Living Area
- 3,728 sq ft
Schools
- Elementary
- Middlebury
- High
- Per Board of Ed
Interior
- Heating
- RadiantZoned
- Heat Fuel
- Propane
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- In Threshold
- Appliances
- Gas RangeWall OvenMicrowaveRefrigeratorFreezerSubzeroDishwasherWasherDryer
- Basement
- FullGarage AccessInterior AccessFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerCable - Pre-wiredOpen Floor PlanSecurity System
- Additional Rooms
- Laundry RoomMud RoomWorkshop
Exterior & Lot
- Lot Size
- 1.04 acres
- Zoning
- R40
- Garage / Parking
- 5 garage spaces12 total parking spacesUnder House GarageDrivewayPrivateCrushed Stone
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- ShakeCedar
- Color
- Blue
- Roof
- Other
- Foundation
- Concrete
- Exterior Features
- GuttersLightingPatio
- Lot Description
- Fence - PartialRolling
Listing & Financials
- Property Taxes
- $13,428 / Annually
- Days on Market
- 0
- MLS #
- 24213699
- MLS Status
- Coming Soon
- Financing
- FHA,VA,CHFA
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/13/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 10/13/2026 at 5:10 PM UTC.