299 High Street
Naugatuck, Connecticut 06770
- Beds
- 6
- Baths
- 3
- SqFt
- 2,497
- Acres
- 0.11
- Year Built
- 1864
- Property Type
- 3 Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
3
13 under contract
Median List Price
$580,000
3 active listings
Median Closed Price
$425,000
39 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.