880 Whittemore Road
Middlebury, Connecticut 06762
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,157
- Acres
- 1.40
- Year Built
- 1966
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
20
19 under contract
Median List Price
$672,000
20 active listings
Median Closed Price
$522,500
74 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 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.