66-68 Alexander Drive
Bridgeport, Connecticut 06606
- Beds
- 4
- Baths
- 2
- SqFt
- 1,590
- Acres
- 0.22
- Year Built
- 1942
- Neighborhood
- North End
- Property Type
- 2 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
HIGHEST & BEST OFFER DUE BY WEDNESDAY 5/27 @ 6PM EST. Exceptional opportunity for both owner-occupants and savvy investors alike! This well-maintained 2-family property offers strong income potential, valuable updates, and a highly convenient location in a sought-after and growing area. Whether you're looking to offset your monthly living expenses by occupying one unit while collecting rental income from the other, or add a solid cash-flowing asset to your portfolio, this property checks all the boxes. Major recent improvements include new furnaces in both units, new hot water heaters, new appliances throughout, new washer & dryer sets in both units, and a newly fenced-in yard. Unit 68 has been extensively updated with new flooring and a beautifully renovated kitchen, creating a modern and inviting living space. Each unit also enjoys its own private driveway, separate backyard space, and dedicated basement storage area - features tenants and owner-occupants alike will appreciate. Conveniently located near schools, shopping, restaurants, public transportation, and major commuter routes, this property offers both lifestyle convenience and long-term investment appeal. A rare chance to secure a versatile multi-family property with strong upside potential in an area continuing to see growth and demand.
Key Facts
- City/Town
- Bridgeport
- Neighborhood
- North End
- Property / Style
- Multi-Family · Units are Side-by-Side
- Year Built
- 1942
- Days on Market
- 68 days
- Beds
- 4
- Baths
- 2 full
- Living Area
- 1,590 sq ft
- Lot Size
- 0.22 acres
- Garage / Parking
- 4 total
- Property Taxes
- $7,052 / Annually
Market Snapshot
The Bridgeport Market
Multi-Family · trailing 12 months
Active Listings
65
62 under contract
Median List Price
$660,000
65 active listings
Median Closed Price
$590,000
259 sales
Median Days on Market
29
65 active listings
Median $ / Sq Ft
$226
65 active listings
Sale-to-List Ratio
100.0%
259 sales
How this home compares
List Price
$499,999
vs $660,000 median
24.2% below median
Price / Sq Ft
$314
vs $226 median
38.9% above median
Days on Market
68 days
vs 29 days median
39 days longer than median
Based on 65 active and 259 closed sales (trailing 12 mo) of multi-family in Bridgeport. Source: SmartMLS · As of July 28, 2026.
Location
66-68 Alexander Drive, Bridgeport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,549
- Property Taxes$588
- Insurance$167
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Bridgeport
- Neighborhood
- North End
- County
- Fairfield
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units are Side-by-Side
- Year Built
- 1942
- New Construction
- No/Resale
- Living Area
- 1,590 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Window Unit
- Laundry Location
- In-Unit
- Basement
- FullStorageFull With Hatchway
Exterior & Lot
- Lot Size
- 0.22 acres
- Zoning
- RA
- Garage / Parking
- 4 total parking spacesOff Street ParkingDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $7,052 / Annually
- Days on Market
- 68
- MLS #
- 24176938
- MLS Status
- Under Contract
Similar Properties
Homes with a close match in area, property type, and price.
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 6:15 AM UTC.