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299 High Street

Naugatuck, Connecticut 06770

PENDING$499,900
Beds
6
Baths
3
SqFt
2,497
Acres
0.11
Year Built
1864
Matt Caiola

Matt Caiola

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About This Home

Welcome to this spacious and well-maintained 3-family home in the heart of Naugatuck, offering an outstanding opportunity for both owner-occupants and investors alike! The second-floor apartment is move-in ready, making it the perfect option for an owner looking to offset their mortgage with rental income. This updated unit features new carpeting, an updated kitchen, and a bright, comfortable layout. The first-floor apartment offers 3 generously sized bedrooms with beautiful hardwood floors, an updated kitchen, and a renovated bathroom. Major exterior improvements include a new roof (2024), new vinyl siding (2025), a new privacy fence (2020), and a fully fenced backyard. Enjoy outdoor living with a welcoming front porch, a rear patio, and a balcony overlooking the attached one-car garage. The property also offers ample off-street parking and beautiful city views. Inside, the oversized basement with high ceilings provides exceptional storage space or endless possibilities for a workshop, recreation area, or future finished bonus space. Additional updates include two newer hot water heaters, while the second and third-floor apartments are heated with electric heat. Whether you're looking to live in one unit while generating rental income or add a solid asset to your investment portfolio, this well-maintained property offers space, flexibility, and tremendous value!

Key Facts

City/Town
Naugatuck
Neighborhood
N/A
Property / Style
Multi-Family · 3updown - Unit(s) per Floor
Year Built
1864
Days on Market
21 days
Beds
6
Baths
3 full
Living Area
2,497 sq ft
Lot Size
0.11 acres
Garage / Parking
1 garage · 5 total
Property Taxes
$7,334 / Annually

Market Snapshot

The Naugatuck Market

Multi-Family · trailing 12 months

Median Days on Market

27

3 active listings

Median $ / Sq Ft

$146

3 active listings

Sale-to-List Ratio

100.0%

39 sales

How this home compares

List Price

$499,900

vs $580,000 median

13.8% below median

Price / Sq Ft

$200

vs $146 median

37.0% above median

Days on Market

21 days

vs 27 days median

6 days fresher than median

Based on 3 active and 39 closed sales (trailing 12 mo) of multi-family in Naugatuck. Source: SmartMLS · As of July 28, 2026.

Location

299 High Street, Naugatuck, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,327

per month

  • Principal & Interest$2,549
  • Property Taxes$611
  • Insurance$167
  • HOA$0

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

Location

City/Town
Naugatuck
Neighborhood
N/A
County
New Haven

Residence

Property Type
Multi-Family
Subtype
3 Family
Style
3updown - Unit(s) per Floor
Year Built
1864
New Construction
No/Resale
Living Area
2,497 sq ft

Schools

Elementary
Per Board of Ed
High
Naugatuck

Interior

Heating
BaseboardHot Water
Heat Fuel
ElectricNatural Gas
Cooling
Ceiling Fans
Laundry
Basement Hook-Up(s)Common Laundry Area
Laundry Location
Basement
Basement
FullFull With Hatchway

Exterior & Lot

Lot Size
0.11 acres
Zoning
RA1
Garage / Parking
1 garage space5 total parking spacesAttached GaragePavedDrivewayAsphalt
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
No
Construction
Aluminum
Color
Blue
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
PorchDeckPatio
Lot Description
Corner LotCity Views

Listing & Financials

Property Taxes
$7,334 / Annually
Days on Market
21
MLS #
24189575
MLS Status
Under Contract
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Daniel Zandvliet

(203) 565-8822

Coldwell Banker Realty 2000

(203) 706-1222

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 5:25 AM UTC.