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$340,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,855 Sq. Ft.
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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.

Full Property Details for 555 Whittemore Rd

General

  • Sold For: $340,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24181461
  • Added to Site: 130 day(s) ago

Interior

  • Number of Rooms: 8
  • Interior Features: Cable - Available
  • Appliances: Gas Range, 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, Corian Counters, Tile Floor, 14 x 11, Main
  • Dining Room: Dining Room - Ceiling Fan, Hardwood Floor, 12 x 11, Main
  • In-Law/Au Pair Suite: Yes

Exterior

  • Exterior Features: Shed, Porch, Gutters, Patio
  • 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: Ceiling Fans, Window Unit
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Public Sewer Connected
  • Water: Private Well

Structural Information

  • Architectural Style: Cape Cod
  • Construction Status: No/Resale
  • Exterior Const.: Aluminum
  • Basement Desc.: Full, Full With Hatchway
  • 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

Green Features

  • Energy Features: Storm Doors, Thermopane Windows

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
Sold by ERA Treanor Real Estate, Veronica Miriam Blekis

Listing agent

— 555 Whittemore Rd —

  • Deb Smolley

    Dave Jones Realty, LLC

Agent Contact: (860) 417-9200 Office Contact: (203) 758-0264

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 555 Whittemore Rd

School District:Regional School District 15
NameGradesDistance
Middlebury Elementary School
550 Whittemore Road, Middlebury, CT 06762
K-50.1 mi
Memorial Middle School, Middlebury, CT
1 Memorial Drive, Middlebury, CT 06762
6-81.2 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-123.6 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

Date
Details
Price
Change
Source
9/10/2026
Sold
$340,000
-24.28%
MLS
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.

Listed by Dave Jones Realty, LLC, Deb Smolley
Sold by ERA Treanor Real Estate, Veronica Miriam Blekis

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555 Whittemore Road, Middlebury, CT 06762 (MLS# 24181461) is a Single Family property that was sold at $340,000 on September 10, 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.