509-515 Gregory Street
Bridgeport, Connecticut 06604
- Beds
- 12
- Baths
- 6
- SqFt
- 5,676
- Acres
- 0.12
- Year Built
- 1895
- Neighborhood
- South End
- Property Type
- 5+ Family

Matt Caiola
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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
Active Listings
74
62 under contract
Median List Price
$678,500
74 active listings
Median Closed Price
$600,000
253 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per 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
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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 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.