555 Whittemore Rd

Middlebury, CT 06762

$449,000
Price
4
Beds
1,855 Sq. Ft.
$242 / Sq. Ft.
1,855
Sq. Ft.
$242
per Sq. Ft.
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Under Contract
Under Contract

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 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....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.
  1. Listed by Deb Smolley • Dave Jones Realty, LLC
    P: (860)-417-9200 C: (860)-417-9200 debsmolley@sbcglobal.net

Property Details for 555 Whittemore Road

Basement Description
Full, Full With Hatchway
Direct Waterfront
No
Garages Number
0
Neighborhood
N/A
Style
Cape Cod
Garage Parking Info
Off Street Parking
Swimming Pool
No
LISTING UPDATED: 07/28/2026 01:15 AM

Property Details for 555 Whittemore Road

StatusUnder Contract
MLS #24181461
Days on Market53
Taxes$5,984 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1946
Lot Size0.34 AC / 14,810 SF
CountyNew Haven County
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Location

Listing Courtesy of Dave Jones Realty, LLC, Deb Smolley
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Building Information for 555 Whittemore Road

Stories-Year Built1946Building Size-Lot Size0.34 AC / 14,810 SF

Payment Calculator

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$2,781 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,282

Property Taxes

$499

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 555 Whittemore Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: gps friendly
  • Elementary School: Per Board of Ed
  • Flood Zone: No
  • High School: Pomperaug
  • Latitude: 41.526886
  • Longitude: -73.100899
  • Neighborhood Amenities: Health Club, Lake, Library, Park, Playground/Tot Lot, Private School(s), Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 3
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $5,984
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Porch, Gutters, Patio
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Unfinished, Access Via Hatch
  • Cooling System: Ceiling Fans, Window Unit
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 0
  • Home Automation: Electric Outlet(s), Thermostat(s)
  • Interior Features: Cable - Available
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Hardwood Floor
  • Room Length: 16.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 14.0
Room 2
  • Room Entry Order: 2
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 11.0
Room 3
  • Room Entry Order: 3
  • Room Features: Book Shelves,Corian Counters,Tile Floor
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 11.0
Room 4
  • Room Entry Order: 4
  • Room Features: Wall/Wall Carpet
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Primary Bedroom
  • Room Width: 13.0
Room 5
  • Listing Key: 5383CDADE557ABDCE0631A01100AF4C8
  • Room Entry Order: 5
  • Room Features: Wall/Wall Carpet
  • Room Length: 12.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Room 6
  • Room Entry Order: 6
  • Room Features: Laminate Floor
  • Room Length: 11.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 8.0
Room 7
  • Room Entry Order: 7
  • Room Features: Wall/Wall Carpet
  • Room Length: 13.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Property
Property and Assessments
  • Color: blue
  • Construction Description: Frame
  • Exterior Siding: Aluminum
  • Foundation Type: Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1946
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor, Separate Entry
  • In Law Apartment: Yes
  • Living Area SQFT Per Public Records: 1855
Lot Information
  • Lot Description: Corner Lot
  • Parcel Number: 1192456
  • Sq Ft Est Heated Above Grade: 1855.0
  • Sq Ft Total: 1855.0
  • Zoning: R40
Utilities
  • Energy Features: Storm Doors, Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Public Sewer Connected
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Public Records for 555 Whittemore Road

Taxable ValueLand$48,700Additions$135,300Total$184,000
Tax Record2025$5,984 ($499 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt1,855 SqFtAbove Grade Finished SqFt1,855 SqFtUnfinished Basement SqFt900 SqFtStories2Lot Size14,810 SqFtStyleSingle Family ResidenceYear Built1946Year Renovated1946ZoningR40CountyNAUGATUCK VALLEYAPNMDBY M:4-06 L:040

Schools near 555 Whittemore Road

This home is within Regional School District 15.
Rating
School
Type
Grades
Distance
Middlebury Elementary School
Public - PK to 5
Memorial Middle School
Public - 6 to 8
Pomperaug Regional High School
Public - 9 to 12
Rating
School
Distance
Middlebury Elementary School
PublicPK to 5

Memorial Middle School
Public6 to 8

Pomperaug Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Dave Jones Realty, LLC, Deb Smolley

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.