299 Oak Street
Waterbury, Connecticut 06705
- Beds
- 4
- Baths
- 2
- SqFt
- 1,792
- Acres
- 0.17
- Year Built
- 1889
- Property Type
- 2 Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Investor package - 299 Oak St is sold together with 301 Oak St (see related MLS listing 24218005); package price $369,900 for both parcels, this listing reflects the allocation for 299 only. Two-family built 1889 with a separate studio over the detached garage. Both apartments are 2 bed / 1 bath: the first floor is intact and needs cosmetics; the second floor kitchen and bath are gutted, the rest is cosmetic. Flat-roof rear addition takes on water and the roof is likely due; stone basement; three electric panels; electric heat. Studio over the garage is gutted. Next door, 301 Oak St is a one-story 3-unit with two fully renovated apartments - six potential units across the package, buyer to verify unit count and zoning with the City of Waterbury. Strictly as-is. Cash or hard money only. Bring your contractor and your vision.
Key Facts
- City/Town
- Waterbury
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1889
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,792 sq ft
- Lot Size
- 0.17 acres
- Garage / Parking
- 1 garage · 4 total
- Property Taxes
- $4,651 / Annually
Market Snapshot
The Waterbury Market
Multi-Family · trailing 12 months
Active Listings
71
31 under contract
Median List Price
$469,900
71 active listings
Median Closed Price
$419,900
197 sales
Median Days on Market
32
71 active listings
Median $ / Sq Ft
$159
71 active listings
Sale-to-List Ratio
100.0%
197 sales
How this home compares
List Price
$166,900
vs $469,900 median
64.5% below median
Price / Sq Ft
$93
vs $159 median
41.5% below median
Days on Market
0 days
vs 32 days median
32 days fresher than median
Based on 71 active and 197 closed sales (trailing 12 mo) of multi-family in Waterbury. Source: SmartMLS · As of October 30, 2026.
Location
299 Oak Street, Waterbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$910
- Property Taxes$388
- Insurance$56
- 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
- 1889
- New Construction
- No/Resale
- Living Area
- 1,792 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Electric
- Cooling
- None
- Basement
- FullInterior AccessDirt Floor
Exterior & Lot
- Lot Size
- 0.17 acres
- Zoning
- RM
- Garage / Parking
- 1 garage space4 total parking spacesDetached GarageOff Street ParkingDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Aluminum
- Roof
- Asphalt ShingleFlat
- Foundation
- Stone
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $4,651 / Annually
- Days on Market
- 0
- MLS #
- 24218013
- MLS Status
- Active
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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 10/30/2026. 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 10/30/2026 at 5:11 PM UTC.