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555 Whittemore Road, Middlebury, CT 06762

Single Family For Sale

$449,000
$242/sqft
555 Whittemore Road, Middlebury, CT
Active
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4
Bedrooms
3
Bathrooms
1,855
Sq Ft
0.34
Acres
1946
Year Built

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.

Listed by Deb Smolley (860) 417-9200 with Dave Jones Realty, LLC (203) 758-0264

Listing Snapshot

Price $449,000 Days on Our Site 7 days
Property Tax $5,984/yr Style Cape Cod
Year Built 1946 Total Sq Ft 1,855
Lot Size 0.34 acres HOA Fees N/A
Bedrooms 4 Full Bathrooms 2
Total Rooms 8 Half Baths 1

Key Features

Interior
  • Cable - Available
Appliances
  • Gas Range
  • Microwave
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
Outdoor
  • Shed
  • Porch
  • Gutters
  • Patio
Nearby
  • Health Club
  • Lake
  • Library
  • Park
  • Playground/Tot Lot
  • Private School(s)
  • Tennis Courts

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Type Off Street Parking

Systems & Utilities

Heat Hot Water
Fuel Oil
Cooling Ceiling Fans, Window Unit
Hot Water Oil, Domestic
Water Private Well
Sewer Public Sewer Connected

Schools

Elem Per Board of Ed
High Pomperaug

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $499/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Jun 4, 2026 Listed $449,000

Frequently Asked Questions

How much does 555 Whittemore Road in Middlebury, CT cost?
This property is listed at $449,000, which works out to $242 per square foot.
How many bedrooms does 555 Whittemore Road have?
This home has 4 bedrooms and 3 bathrooms.
What is the square footage of 555 Whittemore Road?
The home is 1,855 square feet, situated on 0.34 acres.
When was 555 Whittemore Road in Middlebury built?
This property was built in 1946.
Is 555 Whittemore Road, Middlebury, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 555 Whittemore Road, Middlebury in?
This home is served by the Middlebury public school system, with Per Board of Ed as the elementary school and Pomperaug as the high school.
How do I schedule a tour of 555 Whittemore Road, Middlebury, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Deb Smolley · (860) 417-9200

Dave Jones Realty, LLC · (203) 758-0264

MLS# 24181461 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Jul 9, 2026 11:21 AM UTC