Sold on Jul 2026

$380,000

•

1,608

sq ft

55 Highwood Rd, Waterbury, CT 06708

Track this home’s value and nearby sales activity

About this home

Multiple Offers In Review. Be the next chapter in the story of this one-of-a-kind 1930s charmer with only 3 previous owners. Tucked away on a quiet street in a desirable area of Waterbury just minutes from Tracy's Pond this 3-bedroom Cape-style home offers a sense of calm and retreat. Original wide plank wood floors greet you at the door, while fresh paint throughout creates the perfect backdrop for quiet nights in or boisterous nights of entertaining with friends. A wood burning stove in the living room adds to the charm. Two good sized bedrooms are found on the main floor and a third bedroom is privately located on the second floor. The property offers the hard to find vibe of refined coziness. Outside, enjoy a large level partially fenced yard, beautiful landscaping, a wrap around deck and the convenience of a 3rd garage -- perfect for you to store bikes, kayaks, or your prized warm weather "garage queen". Additional features include a 10-year old roof, newer windows, newer siding, hardscaping, and newer water heater.

Single-familyProperty Type

1930Year Built

0.69 acresLot Size

$236Price/Sq.Ft.

3 garage spacesParking

Listed by Julie Avellino • Connecticut Realty Studios LLC

Contact: Agent Attribution Contact: (203) 414-9479

Bought with George Stankus • Showcase Realty, Inc.

Source:Smart MLS #24175647

Redfin Estimate

$376,977

$3,023 since sold in July 2026$6,000 since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 17.3% higher than the average sale price ($321K) of 6 comparable homes.

SOLD JUL 1, 2026
$355,000
A
3 beds1 bath1,193 sq ft
90 Larchmont Ave, Waterbury, CT 06708
SOLD JUL 6, 2026
$400,000
B
3 beds1.5 baths1,572 sq ft
301 Steinmann Ave, Middlebury, CT 06762
SOLD JUL 22, 2026
$350,000
C
3 beds1 bath1,200 sq ft
21 Parklawn Cir, Waterbury, CT 06708
SOLD DEC 12, 2025
$285,000
D
3 beds1.5 baths1,802 sq ft
49 Southridge Dr, Waterbury, CT 06708
SOLD AUG 11, 2026
$250,000
E
3 beds1.5 baths1,536 sq ft
34 Fern Cir, Waterbury, CT 06708
SOLD MAY 22, 2026
$288,000
F
3 beds1 bath1,200 sq ft
30 Parklawn Dr, Waterbury, CT 06708

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Market trends in 06708, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

100.8%

+0.7% MoM

Median sale price

$330K

$12K MoM

Avg. days on market

45d

3 days MoM

Recently sold homes

9 MoM

New listings for sale

NEW 26 HRS AGO
$279,500
3 beds2 baths1,714 sq ft
18 Greenmount Ter, Waterbury, CT 06708
$349,900
3 beds1.5 baths1,456 sq ft
169 Circuit Ave, Waterbury, CT 06708
$300,000
3 beds1.5 baths1,524 sq ft
49 Delaware Ave, Waterbury, CT 06708
$339,900
2 beds1.5 baths1,284 sq ft
879 Congress Ave, Waterbury, CT 06708
$345,000
3 beds2 baths1,236 sq ft
32 Kaynor Dr, Waterbury, CT 06708
COMING SOON
$599,900
4 beds2.5 baths3,914 sq ft
205 Country Club Rd, Waterbury, CT 06708
$279,900
3 beds2 baths1,920 sq ft
Waterbury, CT 06708
$319,000
3 beds1.5 baths1,392 sq ft
85 Mason Ave, Waterbury, CT 06708
$450,000
8 beds3.5 baths2,362 sq ft
265 Congress Ave, Waterbury, CT 06708
$249,900
3 beds2 baths1,454 sq ft
275 Congress Ave, Waterbury, CT 06708
See all

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Rental estimate

Est. $2,008 per month, based on comparable rentals

Sale and tax history for 55 Highwood Rd

Sale History
Tax History

Date

Event

Price

Smart MLS #24175647

Jul 9, 2026

Sold

$380,000

$236/sq ft

Jun 25, 2026

Pending

—

May 26, 2026

Contingent

—

May 22, 2026

Listed

$369,000

$229/sq ft

May 19, 2026

Coming Soon

$369,000

$229/sq ft

Smart MLS #170324465

Sep 25, 2020

Sold

$210,000

$131/sq ft

Aug 21, 2020

Contingent

—

Aug 7, 2020

Price Changed

$189,900

$118/sq ft

Aug 7, 2020

Listed

$187,000

$116/sq ft

Lovingly cared for home by generations! This 3 Bedroom/1 Bath Ranch is beautifully situated on a level lot on a side street and is recently updated and ready for you to just move in and unpack your bags. Large freshly painted kitchen with stainless steel appliances, tile floor, bathroom with tile floor. Hardwood floors on main level were just refinished, and rooms are freshly painted add to that newer roof and recently painted siding. This home is ideal for a first-time home buyer, downsizer, or someone seeking a condo alternative. First floor offers a living room with fireplace with a wood stove insert, two bedrooms, full bath, family room, laundry room and large kitchen with a dining area. Entire yard is visible from multiple windows from the kitchen. Watch the yard while cooking or walk through the sliders to expansive deck and bask in the sunlight. On cold days sit on your dining table and enjoy a hot morning coffee while looking at trees and listening to birds! Enjoy the extra large private deck off the kitchen and large driveway for plenty of parking in addition to 3 garages. Upper level offers a bedroom and a cedar closet. Best of all, this location cannot be beat, local schools and close to area shopping and transportation both in Waterbury and Middlebury. If you are looking for a house that is ready to just open the front door and move into, this is the home for you!!

Sale fell through due to buyer losing his job.

Smart MLS #170287666

Aug 6, 2020

Listing Removed

—

Jun 6, 2020

Contingent

—

May 27, 2020

Price Changed

$180,000

$112/sq ft

May 13, 2020

Relisted

—

Apr 17, 2020

Contingent

—

Apr 11, 2020

Listed

$189,900

$118/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$7,928 (+42.0%)

$31,220 + $115,080

$146,300

2022

$5,583

$31,240 + $61,490

$92,730

2021

$5,583

$31,240 + $61,490

$92,730

2020

$5,583

$31,240 + $61,490

$92,730

2019

$5,583

$31,240 + $61,490

$92,730

2018

$5,583 (+0.9%)

$31,240 + $61,490

$92,730

2017

$5,531

$31,250 + $60,610

$91,860

2016

$5,531 (+5.7%)

$31,250 + $60,610

$91,860

2013

$5,234

$31,250 + $60,610

$91,860

2011

$5,234

$31,250 + $60,610

$91,860

Public record

Public record
Zoning

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.69 Acres

Year renovated

1969

Sq. Ft.

1,608

Year built

1930

Style

Single Family Residential

County

New Haven County

APN

1388061

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

RS-12

Large Lot Single-Family Residential District

The RS-12 District is established to provide for low density single-family residential neighborhoods and limited non-residential uses on lots having a minimum area of 12,000 sq ft. Uses and Conditional Accessory Uses are permitted by Zoning Permit, Special Permit, or Special Exception approval as provided in Article 11 of these Regulations.

Permitted uses

Include but are not limited to:

No uses permitted by right

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Detached Garage, Under House Garage, Paved, Driveway
Garages Number: 3

Parking Information
Parking Total Spaces: 8

Interior

Interior Information
Total Rooms: 7
Laundry Room Location: main floor with storage area
Laundry Room Info: Main Level
In-Law Apartment: No
Fireplaces Total: 1
Cooling System: Window Unit
Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 1

Bedroom Information
Beds Total: 3

Room Information
Rooms Additional: Laundry Room
Basement Description: Full, Unfinished

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Vinyl Siding
Exterior Features: Wrap Around Deck, Deck, Gutters

Lot Information
Lot Description: Fence - Partial, Fence - Privacy, Level Lot

Building Information
Foundation Type: Concrete, Masonry
Construction Description: Frame
Color: grey

Property Information
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 1608
Driveway Type: Private, Paved

Financial

Assessments Information
Assessed Value: $146,300

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Oil
Heat Type: Baseboard, Hot Water, Radiator
Heat Fuel Type: Oil
Fuel Tank Location: In Basement

Location

School Information
High School: Per Board of Ed
Elementary School: Per Board of Ed

Location Information
State: Connecticut
Nearby Amenities: Lake, Park
Directions: Rte 63 to Anawan Ave to Lakeside Blvd W to Highwood Rd
County: New Haven

Public facts

Beds: 3
Baths: 1.0
Sq. Ft.: 1,608
Stories: 2.0
Lot Size: 0.69 acres
Style: Single Family Residential
Year Built: 1930
Year Renovated: 1969
County: New Haven County
APN: 1388061

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 2

Around this home

Schools

B. W. Tinker School

Public PreK-5 • Assigned • 1.9mi

5/10

West Side Middle School

Public 6-8 • Assigned • 1.2mi

4/10

John F. Kennedy High School

Public 9-12 • Assigned • 1.4mi

1/10

Provided by GreatSchools

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

4/10 Heat Factor

7 days above 97° expected this year, 15 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

Waterbury, CT • 06708

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

93/ 100

Exceptional sunlight

Sunscore

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

10.5 hrs

6.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$359,000 – $434,000

Reach more buyers when you sell with Redfin. Plus, you'll save $3,770 in fees.

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4 beds2.5 baths1,819 sq ft

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49 Delaware Ave, Waterbury, CT 06708

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3 beds1.5 baths1,392 sq ft

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New listings for sale in 06708

NEW 26 HRS AGO

$279,500

3 beds2 baths1,714 sq ft

18 Greenmount Ter, Waterbury, CT 06708

$349,900

3 beds1.5 baths1,456 sq ft

169 Circuit Ave, Waterbury, CT 06708

$300,000

3 beds1.5 baths1,524 sq ft

49 Delaware Ave, Waterbury, CT 06708

$339,900

2 beds1.5 baths1,284 sq ft

879 Congress Ave, Waterbury, CT 06708

$345,000

3 beds2 baths1,236 sq ft

32 Kaynor Dr, Waterbury, CT 06708

COMING SOON

$599,900

4 beds2.5 baths3,914 sq ft

205 Country Club Rd, Waterbury, CT 06708

$279,900

3 beds2 baths1,920 sq ft

Waterbury, CT 06708

$319,000

3 beds1.5 baths1,392 sq ft

85 Mason Ave, Waterbury, CT 06708

$450,000

8 beds3.5 baths2,362 sq ft

265 Congress Ave, Waterbury, CT 06708

Home values near 55 Highwood Rd

Data from public records.

Address	Redfin Estimate
30 Highwood Road, Waterbury, CT 3 Beds \| 1 Baths \| 1092 Sq. Ft.	$329,027
54 Highwood Road, Waterbury, CT 3 Beds \| 2 Baths \| 980 Sq. Ft.	$336,434

Address	Redfin Estimate
38 Highwood Road, Waterbury, CT 3 Beds \| 1 Baths \| 960 Sq. Ft.	$293,497
72 Highwood Road, Waterbury, CT 4 Beds \| 2.5 Baths \| 2864 Sq. Ft.	$430,255

Address	Redfin Estimate
48 Highwood Road, Waterbury, CT 2 Beds \| 2 Baths \| 1920 Sq. Ft.	$363,772
65 Highwood Road, Waterbury, CT 2 Beds \| 1.5 Baths \| 1243 Sq. Ft.	$354,135

Property information provided by Smart MLS when last listed in 2026. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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55 Highwood Rd, Waterbury, CT 06708

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About this home

Redfin Estimate

Market trends in 06708, CT

Homeowner tools

Sale and tax history for 55 Highwood Rd

Public record

Property details

Parking

Interior

Exterior

Financial

Utilities

Location

Public facts

Other

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06708

Home values near 55 Highwood Rd

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