4 Academy Street
New Haven, Connecticut 06511
- Beds
- 6
- Baths
- 6
- SqFt
- 3,757
- Acres
- 0.04
- Year Built
- 1860
- Neighborhood
- Wooster Square
- Property Type
- 3 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
Rare opportunity to own a classic brick three-family directly on the park in Wooster Square, one of New Haven's most distinctive and sought-after neighborhoods. This property combines historic character, an exceptional location, and a highly desirable apartment configuration. The building features three spacious 2-bedroom, 2-bathroom apartments, providing a layout that works equally well for an investor or owner-occupant. Each residence offers the added convenience of in-unit laundry, along with generous living space and the privacy of two full bathrooms. The property's timeless brick exterior, arched entryway, and architectural details complement its prime park-front setting in the heart of Wooster Square. Enjoy immediate access to the neighborhood's tree-lined streets, historic architecture, restaurants, cafes, and the renowned Wooster Street dining district, while remaining convenient to Downtown New Haven and Yale. With three 2-bedroom/2-bath units, laundry in every apartment, and an outstanding location directly on Wooster Square Park, this is a unique opportunity to acquire a substantial multifamily property in one of New Haven's premier neighborhoods.
Key Facts
- City/Town
- New Haven
- Neighborhood
- Wooster Square
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1860
- Days on Market
- 0 days
- Beds
- 6
- Baths
- 6 full
- Living Area
- 3,757 sq ft
- Lot Size
- 1,742 sq ft
- Property Taxes
- $23,749 / Annually
Market Snapshot
The New Haven Market
Multi-Family · trailing 12 months
Active Listings
70
51 under contract
Median List Price
$597,000
70 active listings
Median Closed Price
$490,000
309 sales
Median Days on Market
59
70 active listings
Median $ / Sq Ft
$211
70 active listings
Sale-to-List Ratio
100.2%
309 sales
How this home compares
List Price
$950,000
vs $597,000 median
59.1% above median
Price / Sq Ft
$253
vs $211 median
19.9% above median
Days on Market
0 days
vs 59 days median
59 days fresher than median
Based on 70 active and 309 closed sales (trailing 12 mo) of multi-family in New Haven. Source: SmartMLS · As of October 12, 2026.
Location
4 Academy Street, New Haven, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$5,262
- Property Taxes$1,979
- Insurance$317
- 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
- 3 Family
- Style
- Units on different Floors
- Year Built
- 1860
- New Construction
- No/Resale
- Living Area
- 3,757 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- None
- Basement
- Full
Exterior & Lot
- Lot Size
- 1,742 sq ft
- Zoning
- RM2
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Brick
- Roof
- Flat
- Foundation
- Stone
- Lot Description
- City Views
Listing & Financials
- Property Taxes
- $23,749 / Annually
- Days on Market
- 0
- MLS #
- 24212980
- MLS Status
- Active
Similar Properties
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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 10/12/2026. 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 10/12/2026 at 5:20 PM UTC.