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177 Chestnut Street

New Haven, Connecticut 06511

ACTIVE$2,300,000

Reduced from $2,400,000

Beds
16
Baths
12
SqFt
6,009
Acres
0.12
Year Built
1900
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

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Price Reduced

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$14,379

per 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

Homes with a close match in area, property type, and price.

Listed By

Arian Hoxha

(203) 558-4798

Serhant Connecticut, LLC

(203) 489-7800

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.