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$279,900 Contingent

  • For Sale
  • Contingent
  • Multi-Family
  • 8 Total Beds
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Stately Victorian Two-Family in Waterbury's Historic Hillside District! Spacious home offering over 2,900 sq ft of living space and more than $3,000 per month in rental income! The first-floor unit features 5 rooms and 3 bedrooms, while the expansive second-floor apartment extends into a finished attic, boasting 10 rooms, 5 bedrooms, and 2 full baths. Both units showcase beautiful hardwood floors, original woodwork, newer windows, and separate utilities. Sold in "As Is" condition. Enjoy easy access to highways, shopping, dining, the downtown green, two major hospitals, and public transportation. Just a short walk to the Metro-North train station and the iconic 70+ acre Fulton Park, complete with ponds, walking trails, tennis courts, ball fields, playground, and a newly renovated public pool. Perfectly situated less than 45 minutes from Bridgeport and Danbury, and under 2 hours from NYC-this property blends historic charm with modern convenience. A rare opportunity for owner-occupants or investors alike!

Full Property Details for 53 Hillside Ave

General

  • Price: $279,900
  • Taxes: (July 2025-June 2026)
  • Status: Contingent
  • Type: Multi-Family
  • Source: SMARTMLS
  • MLS ID: 24134783
  • Updated: 12/16/2025
  • Added to Site: 86 day(s) ago

Interior

  • Number of Rooms: 15

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 8

Other Rooms

  • Laundry: Hook-Up In Unit 2

Exterior

  • Exterior Features: Porch-Enclosed, Balcony, Porch, Lighting

Parking

  • Total Spaces: 1
  • Parking: None, Off Street Parking, Driveway, Unpaved

Location

  • County: New Haven
  • Neighborhood: Hillside
  • Driving Directions: Corner of Hillside & Second Ave.

School Information

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

Community

  • Community Name: Hillside

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Hot Air, Hot Water, Natural Gas, Oil
  • Heating Fuel: Natural Gas, Oil
  • Water Heater: Natural Gas, Electric, Upright Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Units on different Floors
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Full, Unfinished, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,952
  • Above Ground: 2,952 Sq. Ft.
  • Year Built: 1875

Unit Information

Unit 1

  • Total Bathrooms: 1
  • Bedrooms: 3

Unit 2

  • Total Bathrooms: 2
  • Bedrooms: 5

Lot Features

  • Lot Size (Acres): 0.08
  • Driveway/Sidewalk: Private, Dirt
  • Zoning: RM
  • Lot Description: Corner Lot, Historic District

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Assessment Amount: $77,740
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1378146

Listed by Great Estates, CT, Vasco Silva

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Listing agent

— 53 Hillside Ave —

  • Vasco Silva

    Great Estates, CT

Agent Contact: (203) 217-3218 Office Contact: (203) 200-7030

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 53 Hillside Ave

School District:Waterbury School District
NameGradesDistance
Driggs School
77 Woodlawn Terrace, Waterbury, CT 06710
K-50.2 mi
West Side Middle School
483 Chase Parkway, Waterbury, CT 06708
6-81.6 mi
John F. Kennedy High School
422 Highland Avenue, Waterbury, CT 06708
9-121.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 53 Hillside Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/25/2025
Listed
$279,900
76.04%
MLS
8/19/2022
Sold
$159,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 53 Hillside Ave

Year
Property Taxes
Change
Tax Assessment
Change
2024
$4,197
-9%
$93,310
—
2023
$4,613
-9%
$93,310
—
2023
$5,056
171%
$93,310
201%
2022
$1,868
—
$31,030
—
2021
$1,868
—
$31,030
—
2020
$1,868
—
$31,030
—
2019
$1,868
—
$31,030
—
2018
$1,868
—
$31,030
—
2017
$1,871
—
$31,080
—
2016
$1,871
3%
$31,080
—
2015
$1,809
2%
$31,080
—
2011
$1,771
—
$31,080
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Great Estates, CT, Vasco Silva

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53 Hillside Avenue, Waterbury, CT 06710 (MLS# 24134783) is a Multi-Family property with 2 units containing 8 bedrooms and 3 full bathrooms. 53 Hillside Avenue is currently listed for $279,900 and was received on October 21, 2025. Want to learn more about 53 Hillside Avenue? Do you have questions about finding other Multi-Family real estate for sale in Waterbury? You can browse all Waterbury real estate or contact a Coldwell Banker agent to request more information.

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