4 Jefferson Street
New Haven, Connecticut 06511
Reduced from $590,000
- Beds
- 4
- Baths
- 2
- SqFt
- 2,380
- Acres
- 0.11
- Year Built
- 1890
- Neighborhood
- Wooster Square
- Property Type
- 2 Family

Matt Caiola
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About This Home
**Eligible Yale University employees may qualify for up to $30,000 through the Yale Homebuyer Program**. Located in historic Wooster Square overlooking Lenzi Park, this two-family home offers charm, flexibility, and an exceptional location in one of New Haven's most desirable neighborhoods. Just minutes from Yale University, Yale New Haven Hospital, Downtown New Haven, Union Station, I-91, I-95, local restaurants, coffee shops, and Wooster Street's famous pizza scene, this property combines the convenience of city living with the character of a historic neighborhood. The owner's unit features tandem bedrooms, offering the perfect opportunity for a home office, nursery, or dressing room, along with hardwood floors, abundant natural light, a fireplace, and an updated eat-in kitchen with restored cabinetry and quartz countertops and a dishwasher. The second-floor apartment offers updated flooring, a functional layout, and its own laundry. Both units include newer boilers, updated hot water heaters, and separate utilities. Outside, enjoy a private patio surrounded by perennial gardens, plus a detached garage with an oversized studio/workshop ideal for a home office, fitness room, artist's studio, or additional storage. Additional highlights include a newer roof, windows, walk-up attic, full basement, natural gas heat, public utilities, and off-street parking. Whether you're looking for a home with room for extended family, space for guests, or the flexibility that a t
Key Facts
- City/Town
- New Haven
- Neighborhood
- Wooster Square
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1890
- Days on Market
- 76 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 2,380 sq ft
- Lot Size
- 0.11 acres
- Garage / Parking
- 1 garage · 3 total
- Property Taxes
- $11,297 / Annually
Market Snapshot
The New Haven Market
Multi-Family · trailing 12 months
Active Listings
61
64 under contract
Median List Price
$599,900
61 active listings
Median Closed Price
$475,000
293 sales
Median Days on Market
41
61 active listings
Median $ / Sq Ft
$212
61 active listings
Sale-to-List Ratio
100.1%
293 sales
How this home compares
List Price
$575,000
vs $599,900 median
In line with median
Price / Sq Ft
$242
vs $212 median
14.2% above median
Days on Market
76 days
vs 41 days median
35 days longer than median
Based on 61 active and 293 closed sales (trailing 12 mo) of multi-family in New Haven. Source: SmartMLS · As of July 28, 2026.
Location
4 Jefferson Street, New Haven, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,932
- Property Taxes$941
- Insurance$192
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- New Haven
- Neighborhood
- Wooster Square
- County
- New Haven
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units on different Floors
- Year Built
- 1890
- New Construction
- No/Resale
- Living Area
- 2,380 sq ft
Schools
- Elementary
- East Rock
- High
- Wilbur Cross
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Ceiling FansWindow Unit
- Fireplaces
- 1
- Laundry
- Basement Hook-Up(s)Hook-Up In Unit 2
- Laundry Location
- #1 in basement- #2 in unit
- Basement
- FullUnfinishedShared BasementConcrete Floor
Exterior & Lot
- Lot Size
- 0.11 acres
- Zoning
- RM2
- Garage / Parking
- 1 garage space3 total parking spacesDetached GarageDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer In Street
- Flood Zone
- No
- Construction
- Aluminum
- Color
- brown
- Roof
- Asphalt Shingle
- Foundation
- Masonry
- Exterior Features
- PorchGuttersLightingPatio
- Lot Description
- City ViewsLevel Lot
Listing & Financials
- Property Taxes
- $11,297 / Annually
- Days on Market
- 76
- MLS #
- 24173215
- MLS Status
- Under Contract - Continue to Show
- 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 7:05 AM UTC.