177 Chestnut Street
New Haven, Connecticut 06511
Reduced from $2,400,000
- Beds
- 16
- Baths
- 12
- SqFt
- 6,009
- Acres
- 0.12
- Year Built
- 1900
- Neighborhood
- Wooster Square
- Property Type
- 5+ 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
Turn-key 6-unit multifamily investment opportunity in New Haven's highly desirable Wooster Square neighborhood! Fully renovated and fully leased with long-term tenants in place, this income-producing asset offers true "collect the keys and collect the rent" ownership. Ideally located just minutes from Downtown New Haven, Yale University, Yale New Haven Hospital, Union Station, I-95, and I-91, the property benefits from strong rental demand driven by education, healthcare, biotech, and technology sectors. The approximately 6,009 SF building features updated units with modern kitchens, renovated bathrooms, contemporary finishes, and attractive layouts that appeal to today's renters. Tenants enjoy walkable access to Wooster Square Park, renowned restaurants including Frank Pepe's and Sally's Apizza, shopping, entertainment, cultural attractions, and direct rail access to New York City. With 5 off-street parking spaces, stable cash flow, and a premier location surrounded by ongoing residential and mixed-use development, this is a rare opportunity to own a fully stabilized multifamily asset in one of Connecticut's strongest rental markets.
Key Facts
- City/Town
- New Haven
- Neighborhood
- Wooster Square
- Property / Style
- Multi-Family · Units on different Floors,Units are Side-by-Side
- Year Built
- 1900
- Days on Market
- 53 days
- Beds
- 16
- Baths
- 12 full
- Living Area
- 6,009 sq ft
- Lot Size
- 0.12 acres
- Garage / Parking
- 5 total
- Property Taxes
- $22,618 / 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
$2.30M
vs $599,900 median
3.8× the median
Price / Sq Ft
$383
vs $212 median
80.7% above median
Days on Market
53 days
vs 41 days median
12 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
177 Chestnut Street, New Haven, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$11,727
- Property Taxes$1,885
- Insurance$767
- 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
- 5 Family+
- Style
- Units on different Floors,Units are Side-by-Side
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 6,009 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Laundry
- Washer/Dryer All Units
- Basement
- FullUnfinished
Exterior & Lot
- Lot Size
- 0.12 acres
- Zoning
- RM2
- Garage / Parking
- 5 total parking spacesPavedOff Street ParkingDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- AluminumBrick
- Roof
- Gable
- Foundation
- Stone
- Lot Description
- Lightly Wooded
Listing & Financials
- Property Taxes
- $22,618 / Annually
- Days on Market
- 53
- MLS #
- 24181250
- MLS Status
- Active
Similar Properties
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Co-Listed By
Tonino Mavuli
Serhant Connecticut, LLC
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.