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783 Whittemore Road

Middlebury, Connecticut 06762

COMING SOON - NEW$725,000
Beds
5
Baths
3
SqFt
3,728
Acres
1.04
Year Built
1953
Matt Caiola

Matt Caiola

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5-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,377

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Sean Jackson

(203) 581-2334

Keller Williams Realty

(203) 429-4020

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.