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509-515 Gregory Street

Bridgeport, Connecticut 06604

ACTIVE - NEW$1,175,000
Beds
12
Baths
6
SqFt
5,676
Acres
0.12
Year Built
1895
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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About This Home

Welcome to 509-515 Gregory Street, Bridgeport, Connecticut, a compelling six-unit multifamily investment opportunity offering attractive in-place cash flow and significant rental upside. Ideally positioned on a prominent corner at Gregory and Rennell Streets in Bridgeport's South Side, this approximately 5,700-square-foot property presents investors with the opportunity to acquire a well-positioned residential asset in an excellent neighborhood in one of the fastest growing rental markets in the US. The property consists of six generously sized apartments, including four 2.5-bedroom units and two 2-bedroom units. These larger-than-average layouts appeal to a broad tenant base and offer a competitive advantage in attracting and retaining residents. All utilities are separately metered, helping minimize owner-paid operating expenses, while a dedicated rear parking area accommodates approximately six vehicles. The property's location further enhances its appeal. Situated within walking distance of Seaside Park, The Hartford Healthcare Ampitheater, the University of Bridgeport, and Downtown Bridgeport, the property benefits from proximity to some of the city's most significant neighborhood amenities and employment centers. These nearby destinations support consistent rental demand from students, university personnel, and working professionals.

Key Facts

City/Town
Bridgeport
Neighborhood
South End
Property / Style
Multi-Family · Units are Side-by-Side
Year Built
1895
Days on Market
1 day
Beds
12
Baths
6 full
Living Area
5,676 sq ft
Lot Size
0.12 acres
Garage / Parking
6 total
Property Taxes
$10,149 / Annually

Market Snapshot

The Bridgeport Market

Multi-Family · trailing 12 months

Median Days on Market

46

74 active listings

Median $ / Sq Ft

$219

74 active listings

Sale-to-List Ratio

100.0%

253 sales

How this home compares

List Price

$1.18M

vs $678,500 median

73.2% above median

Price / Sq Ft

$207

vs $219 median

5.5% below median

Days on Market

0 days

vs 46 days median

46 days fresher than median

Based on 74 active and 253 closed sales (trailing 12 mo) of multi-family in Bridgeport. Source: SmartMLS · As of November 10, 2026.

Location

509-515 Gregory Street, Bridgeport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$7,606

per month

  • Principal & Interest$6,368
  • Property Taxes$846
  • Insurance$392
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Bridgeport
Neighborhood
South End
County
Fairfield

Residence

Property Type
Multi-Family
Subtype
5 Family+
Style
Units are Side-by-Side
Year Built
1895
New Construction
No/Resale
Living Area
5,676 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Natural Gas
Cooling
Window Unit
Basement
Full

Exterior & Lot

Lot Size
0.12 acres
Zoning
RB
Garage / Parking
6 total parking spacesDrivewayPavedParking LotPrivate
Waterfront Details
Walk to Water
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Flat
Foundation
Brick
Lot Description
Corner LotCity ViewsLevel LotWater View

Listing & Financials

Property Taxes
$10,149 / Annually
Days on Market
1
MLS #
24220476
MLS Status
Active

Similar Properties

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

Listed By

Daniel Shawah

(203) 521-6348

Baldwin Pearson & Co., Inc

(203) 335-5117

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 11/11/2026. 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 11/11/2026 at 6:16 PM UTC.