Date
Details
Price
Change
Source
6/04/2026
Listed
$449,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
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 glore, stainless steel refrigerator, dishwaher and microwave and propane stove. 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, etc....and convenient access to Route 8 and I-84.
Full Property Details
Full Property Details for 555 Whittemore Rd
General
- Price: $449,000
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24181461
- Updated: 7/7/2026
- Added to Site: 33 day(s) ago
Interior
- Number of Rooms: 8
- Appliances: Microwave, Refrigerator, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
- Primary Bedroom: Primary Bedroom - Wall/Wall Carpet, 13 x 13, Main
- Bedroom 1: Bedroom - Laminate Floor, 11 x 8, Upper
- Bedroom 2: Bedroom - Wall/Wall Carpet, 12 x 12, Upper
- Bedroom 3: Bedroom - Wall/Wall Carpet, 13 x 13, Upper
Other Rooms
- Living Room: Living Room - Hardwood Floor, 16 x 14, Main
- Eat In Kitchen: Eat-In Kitchen - Book Shelves, Tile Floor, 14 x 11, Main
- Dining Room: Dining Room - Ceiling Fan, Hardwood Floor, 12 x 11, Main
Exterior
- Color: blue
Parking
- Total Spaces: 3
- Parking: Off Street Parking
Location
- County: New Haven
- Driving Directions: gps friendly
School Information
- Elementary School: Per Board of Ed
- High School: Pomperaug
Heating & Cooling
- Cooling Type: Window Unit
- Heating Type: Hot Water, Oil
- Heating Fuel: Oil
- Water Heater: Other
Utilities
- Sewer: Public Sewer Connected
- Water: Private Well
Structural Information
- Architectural Style: Cape Cod
- Construction Status: No/Resale
- Exterior Const.: Aluminum
- Basement Desc.: Full
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 1,855
- Above Ground: 1,855 Sq. Ft.
- Year Built: 1946
Lot Features
- Lot Size (Acres): 0.34
- Zoning: R40
- Lot Description: Corner Lot
Financial Considerations
- Assessment Amount: $184,000
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 1192456
Listed by Dave Jones Realty, LLC, Deb Smolley
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 555 Whittemore Rd —
Deb Smolley
Dave Jones Realty, LLC
Agent Contact: (860) 417-9200 Office Contact: (203) 758-0264
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 555 Whittemore Rd
School District:Regional School District 15
| Name | Grades | Distance |
|---|---|---|
Middlebury Elementary School 550 Whittemore Road, Middlebury, CT 06762 | K-5 | 0.1 mi |
Memorial Middle School, Middlebury, CT 1 Memorial Drive, Middlebury, CT 06762 | 6-8 | 1.2 mi |
Pomperaug Regional High School 234 Judd Road, Southbury, CT 06488 | 9-12 | 3.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 555 Whittemore Rd
Tax History
Tax History for 555 Whittemore Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,984
—
$184,000
—
2023
$5,998
1%
$184,000
—
2023
$5,936
3%
$184,000
—
2022
$5,752
20%
$184,000
34%
2021
$4,779
-1%
$137,200
—
2020
$4,816
5%
$137,200
—
2019
$4,582
3%
$137,200
—
2018
$4,460
3%
$137,200
—
2017
$4,320
-2%
$137,200
-3%
2016
$4,391
3%
$141,600
—
2015
$4,265
3%
$141,600
—
2014
$4,155
2%
$141,600
—
2011
$4,087
—
$141,600
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 555 Whittemore Rd
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- Single Family
- Active
- Updated 4 days ago
- 2Beds
- 2Total Baths
- 1,188Sq. Ft.
- Single Family
- Active
- Updated 16 minutes ago
- 3Beds
- 4Total Baths
- 4,385Sq. Ft.
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- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 3Total Baths
- 2,032Sq. Ft.
- Single Family
- Active
- Updated 5 days ago
- 4Beds
- 2Total Baths
- 1,512Sq. Ft.
- Single Family
- Active
- Updated 4 days ago
- 4Beds
- 5Total Baths
- 3,865Sq. Ft.
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- Single Family
- Closed
- Updated 18 hours ago
- 3Beds
- 2Total Baths
- 1,572Sq. Ft.
Listed by The Dawn Ciapetti Team
Sold by William Raveis Real Estate
Sold by William Raveis Real Estate
555 Whittemore Road, Middlebury, CT 06762 (MLS# 24181461) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 555 Whittemore Road is currently listed for $449,000 and was received on June 04, 2026. Want to learn more about 555 Whittemore Road? Do you have questions about finding other Single Family real estate for sale in Middlebury? You can browse all Middlebury real estate or contact a Coldwell Banker agent to request more information.