Pending

$449,000

Est. $3,004/mo —

•

1,855

sq ft

555 Whittemore Rd, Middlebury, CT 06762

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.

Single-familyProperty Type

1946Year Built

0.34 acresLot Size

$242Price/Sq.Ft.

3 spacesParking

Listed by Deb Smolley • Dave Jones Realty, LLC

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

Source:Smart MLS #24181461

Payment calculator

$3,004 per month

Principal and interest$2,360

Property taxes

$499

HOA dues

Home insurance

$146

Utilities

Add

5 minutes to get started. No credit impact.

Mortgage resources

Open houses

No upcoming open houses.

Nearby open houses (6)

OPEN TODAY, 11AM TO 1PM
$279,999
3 beds1 bath912 sq ft
146 Downes St, Waterbury, CT 06704
OPEN SAT, 12PM TO 2PM3D & VIDEO TOUR
$778,585
2 beds2.5 baths2,454 sq ft
1111 St Andrews Dr Lot 16, Oxford, CT 06478
OPEN SAT, 12PM TO 2PM3D & VIDEO TOUR
$754,150
2 beds2.5 baths1,955 sq ft
1138 St Andrews Dr Lot 90, Oxford, CT 06478
OPEN SAT, 12PM TO 2PM3D & VIDEO TOUR
$709,555
2 beds2.5 baths2,454 sq ft
1129 St Andrews Dr Lot 49, Oxford, CT 06478
OPEN SAT, 12PM TO 2PM
$564,000
5 beds3.5 baths1,842 sq ft
40 Booth Ter, Hamden, CT 06518
OPEN SEP 13, 12PM TO 2PM
$360,000
2 beds2 baths1,432 sq ft
972 Heritage Vlg Unit B, Southbury, CT 06488

Around this home

Schools

K - 12
Preschool & daycare

Middlebury Elementary School

Public PreK-5 • Assigned • 0.1mi

5/10

Memorial Middle School

Public 6-8 • Assigned • 1.2mi

8/10

Pomperaug Regional High School

Public 9-12 • Assigned • 3.5mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

555 Whittemore Rd · $449,000

DAYS ON MARKET

The average home goes pending in 39 days.

SALE-TO-LIST

Most homes are selling 3% above list price.

LIST PRICE

Median sale price in this area is $473,243. (5% higher than this home)

PRICE DROP

16% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bedroom

Living

Interior features
Cable available
Electric outlets
Thermostats
Ceiling fans
Window air conditioning units
Full basement
Attic with hatch access

Bedrooms
4 bedrooms

Bathrooms
2 full bathrooms
1 half bathroom

Kitchen
Gas range
Microwave
Refrigerator
Dishwasher

Laundry & utility
Washer and dryer
Oil-fired hot water heating
Fuel tank located in basement

Heating & cooling
Hot water heating (oil)
Ceiling fans
Window units for cooling

Sale and tax history for 555 Whittemore Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2022

$5,752 (+20.4%)

$48,700 + $135,300

$184,000

2021

$4,779 (−0.8%)

$55,600 + $81,600

$137,200

2020

$4,816 (+5.1%)

$55,600 + $81,600

$137,200

2019

$4,582 (+2.7%)

$55,600 + $81,600

$137,200

2018

$4,460 (+3.2%)

$55,600 + $81,600

$137,200

2017

$4,320 (−1.6%)

$55,600 + $81,600

$137,200

2016

$4,391 (+5.7%)

$64,900 + $76,700

$141,600

2014

$4,155 (+1.7%)

$64,900 + $76,700

$141,600

2011

$4,087

$64,900 + $76,700

$141,600

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.34 Acres

Year renovated

—

Finished Sq. Ft.

1,855

Unfinished Sq. Ft.

—

Total Sq. Ft.

1,855

Year built

1946

Style

Single Family Residential

County

New Haven County

APN

1192456

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 97° expected this year, 16 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Middlebury, CT • 06762

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

88/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.8 hrs

5.8 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 555 Whittemore Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $400,000 and $480,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $400K to $480K.

SOLD JUL 6, 2026
$400,000 Last sold price
3 beds1.5 baths1,572 sq ft
301 Steinmann Ave, Middlebury, CT 06762
$12/sq ft
8 years newer
SOLD JUL 10, 2026
$435,000 Last sold price
3 beds2 baths1,812 sq ft
123 Evelyn Dr, Naugatuck, CT 06770
$2/sq ft
larger lot
22 years newer
SOLD JUL 1, 2026
$430,000 Last sold price
3 beds2.5 baths1,739 sq ft
422 Jones Rd, Naugatuck, CT 06770
$5/sq ft
larger lot
58 years newer
SOLD JUL 16, 2026
$400,000 Last sold price
3 beds2.5 baths1,976 sq ft
163 Lucille St, Waterbury, CT 06708
$40/sq ft
smaller lot
24 years newer
SOLD JUN 22, 2026
$445,000 Last sold price
4 beds3 baths1,921 sq ft
166 Round Hill Rd, Naugatuck, CT 06770
$10/sq ft
larger lot
23 years newer
SOLD DEC 22, 2025
$480,000 Last sold price
3 beds2.5 baths2,110 sq ft
243 Stonefence Rd, Naugatuck, CT 06770
$15/sq ft
larger lot
47 years newer

This home is pending

The seller has accepted an offer, and this property is now .

Have questions?

Anthony Cervoni

Middlebury Redfin Agent

Anthony Cervoni typically replies in about 15 minutes

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FOR SALE BY OWNER

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3D WALKTHROUGH

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1 bed1 bath889 sq ft

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Details provided by Smart MLS and may not match the public record. Learn more.

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About this home

Payment calculator

Mortgage resources

Open houses

Nearby open houses (6)

Around this home

Schools

Lifestyle

Market insights

Property details

Sale and tax history for 555 Whittemore Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 555 Whittemore Rd

This home is pending

Have questions?

Nearby similar homes

New listings for sale in 06762

More real estate resources