555 Whittemore Road
Middlebury, Connecticut 06762
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 1,855
- Acres
- 0.34
- Year Built
- 1946
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Welcome to this charming Cape Cod home, situated on a 0.34-acre corner lot in the highly desirable town of Middlebury. This home offers 1,855 square feet of comfortable living space with 4 bedrooms and 2.5 baths. The heart of the home features updated oversized country kitchen, with cabinets galore, stainless steel refrigerator, dishwaher and microwave and a gas range. Formal Living Room and Formal Dining Room for your gatherings and entertaining. Newer windows, doors. Remodeled and updated bathrooms. First floor laundry room and bedroom for your convenience. Also, an in-law apartment provides added flexibility for extended family, guests, or potential rental income. The in-law was originally the two car garage that can be converted back! Enjoy all that Middlebury has to offer, including its small-town charm, highly rated schools, wonderful parks, popular restaurants, lake, tennis courts,health club, walking and riding trails, health club and convenient access to Route 8 and I-84.
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1946
- Days on Market
- 53 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 1,855 sq ft
- Lot Size
- 0.34 acres
- Garage / Parking
- 3 total
- Property Taxes
- $5,984 / 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
$449,000
vs $672,000 median
33.2% below median
Price / Sq Ft
$242
vs $277 median
12.6% below median
Days on Market
53 days
vs 43 days median
10 days longer 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
555 Whittemore Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,289
- Property Taxes$499
- Insurance$150
- 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
- Cape Cod
- Year Built
- 1946
- New Construction
- No/Resale
- Living Area
- 1,855 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Pomperaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Ceiling FansWindow Unit
- Appliances
- Gas RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullFull With Hatchway
- In-Law Apartment
- YesFirst FloorSeparate Entry
- Interior Features
- Cable - Available
Exterior & Lot
- Lot Size
- 0.34 acres
- Zoning
- R40
- Garage / Parking
- 3 total parking spacesOff Street Parking
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Aluminum
- Color
- blue
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- ShedPorchGuttersPatio
- Lot Description
- Corner Lot
Listing & Financials
- Property Taxes
- $5,984 / Annually
- Days on Market
- 53
- MLS #
- 24181461
- MLS Status
- Under Contract
Similar Properties
Homes with a close match in area, property type, and price.
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 5:20 AM UTC.