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31 Hillcrest Avenue

Waterbury, Connecticut 06705

PENDING$425,000
Beds
3
Baths
3
SqFt
1,876
Acres
0.16
Year Built
1925
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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About This Home

Discover the perfect blend of timeless character and modern updates in this impeccably maintained two-family home on a corner lot in Waterbury. Whether you're seeking a smart investment opportunity or a flexible multigenerational living arrangement, this spacious property delivers. Live on the two-floor upper level and draw income from the three-room garden apartment with a private entrance and laundry hookup below. The fully renovated, 1,300+ square-foot main residence is filled with natural light and showcases quality craftsmanship throughout. The open concept living-dining area leads to a beautifully updated kitchen with fine finishes, plus a roomy home office space. Upstairs, the primary bedroom feels like an airy private retreat with its vaulted ceilings and abundant sunlight, second full bath, and 11-by-17 bonus room (currently used as a walk-in closet.) Rich architectural details add warmth and personality to every room. Once outside, enjoy a private backyard with plenty of space to relax, garden, or play. The partially covered deck significantly extends your entertaining space and provides the perfect setting for outdoor enjoyment. A detached outbuilding offers additional storage or conversion potential. Conveniently located close to shopping, parks, I-84 and the bus line, this versatile property combines comfort, character, and practicality in one exceptional package. A rare opportunity for owner-occupants and investors alike.

Key Facts

City/Town
Waterbury
Neighborhood
N/A
Property / Style
Multi-Family · Units on different Floors
Year Built
1925
Days on Market
70 days
Beds
3
Baths
3 full
Living Area
1,876 sq ft
Lot Size
0.16 acres
Property Taxes
$5,318 / Annually

Market Snapshot

The Waterbury Market

Multi-Family · trailing 12 months

Median Days on Market

48

51 active listings

Median $ / Sq Ft

$158

51 active listings

Sale-to-List Ratio

100.0%

198 sales

How this home compares

List Price

$425,000

vs $439,900 median

In line with median

Price / Sq Ft

$227

vs $158 median

43.7% above median

Days on Market

70 days

vs 48 days median

22 days longer than median

Based on 51 active and 198 closed sales (trailing 12 mo) of multi-family in Waterbury. Source: SmartMLS · As of July 29, 2026.

Location

31 Hillcrest Avenue, Waterbury, Connecticut

Property + 10 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,752

per month

  • Principal & Interest$2,167
  • Property Taxes$443
  • Insurance$142
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Waterbury
Neighborhood
N/A
County
New Haven

Residence

Property Type
Multi-Family
Subtype
Duplex
Style
Units on different Floors
Year Built
1925
New Construction
No/Resale
Living Area
1,876 sq ft
Below Grade
550 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
BaseboardOther
Heat Fuel
Electric
Cooling
Window Unit
Basement
FullFully Finished

Exterior & Lot

Lot Size
0.16 acres
Zoning
RL
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl SidingAluminumStucco
Color
Blue
Roof
Asphalt Shingle
Foundation
MasonryStone
Exterior Features
ShedDeckGarden AreaCovered Deck
Lot Description
Corner Lot

Listing & Financials

Property Taxes
$5,318 / Annually
Days on Market
70
MLS #
24173184
MLS Status
Under Contract - Continue to Show
Financing
FHA,VA,CHFA

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Jeffrey Boucher

(203) 709-1423

Drakeley Real Estate, Inc.

(203) 263-4336

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/29/2026 at 10:10 AM UTC.