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880 Whittemore Road

Middlebury, Connecticut 06762

PENDING$499,000
Beds
4
Baths
2 | 1
SqFt
2,157
Acres
1.40
Year Built
1966
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Highest and Best by Tuesday, the 21st, 5pm. Welcome to this charming four-bedroom traditional Colonial, privately tucked away on a secluded lot while offering the convenience of city sewer. This light and bright home combines timeless character with important modern updates, including a DeGiorgi roof with a transferable warranty, a new driveway, updated electrical panel, and a newer boiler. Inside, a classic center hall foyer with a graceful staircase welcomes you. The spacious eat-in kitchen is ideal for everyday living, while the formal dining room, complete with a charming swinging door, and is perfect for entertaining. The front-to-back living room features a cozy wood-burning fireplace and new sliding glass doors that open to the backyard, creating a seamless connection to outdoor living. A tucked-away office or den with built-ins provides the perfect space for working from home, reading, or relaxing. Upstairs, the generous primary suite offers a private full-bath along with his-and-hers closets. Three additional bedrooms provide ample space for family, guests, or hobbies. Hardwood floors run throughout the home, enhancing its warmth and classic appeal. Completing the property is an attached two-car garage and a private setting that offers both tranquility and convenience. This charming Colonial is the perfect blend of traditional elegance, thoughtful updates, and comfortable living.

Key Facts

City/Town
Middlebury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1966
Days on Market
13 days
Beds
4
Baths
2 full · 1 half
Living Area
2,157 sq ft
Lot Size
1.40 acres
Garage / Parking
2 garage · 10 total
Property Taxes
$8,437 / Annually

Market Snapshot

The Middlebury Market

Single Family · trailing 12 months

Median Days on Market

43

20 active listings

Median $ / Sq Ft

$277

20 active listings

Sale-to-List Ratio

99.8%

74 sales

How this home compares

List Price

$499,000

vs $672,000 median

25.7% below median

Price / Sq Ft

$231

vs $277 median

16.6% below median

Days on Market

13 days

vs 43 days median

30 days fresher than median

Based on 20 active and 74 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of July 28, 2026.

Location

880 Whittemore Road, Middlebury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,413

per month

  • Principal & Interest$2,544
  • Property Taxes$703
  • Insurance$166
  • 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
Colonial
Year Built
1966
New Construction
No/Resale
Living Area
2,157 sq ft

Schools

Elementary
Middlebury
High
Pomperaug

Interior

Heating
Baseboard
Heat Fuel
Oil
Cooling
None
Fireplaces
1
Laundry
Lower Level
Laundry Location
Basement
Appliances
Electric RangeRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullUnfinishedSump PumpFull With Hatchway
In-Law Apartment
No

Exterior & Lot

Lot Size
1.40 acres
Zoning
R40
Garage / Parking
2 garage spaces10 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPrivatePavedAsphalt
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Color
grey
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
GuttersLighting
Lot Description
Lightly WoodedLevel Lot

Listing & Financials

Property Taxes
$8,437 / Annually
Days on Market
13
MLS #
24189438
MLS Status
Under Contract - Continue to Show
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Christina Zainc

(860) 637-0620

BHGRE Gaetano Marra Homes

(203) 758-1300

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 5:10 AM UTC.