509-511 Roosevelt Drive
Derby, Connecticut 06418
- Beds
- 6
- Baths
- 3 | 1
- SqFt
- 2,592
- Acres
- 0.23
- Year Built
- 1985
- 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
DERBY MULTIFAMILY INVESTMENT OPPORTUNITY - TWO UNITS, SIX BEDROOMS, IMMEDIATE FLEXIBILITY! Investors, owner-occupants, and portfolio builders-this is the opportunity you've been waiting for! 509-511 Roosevelt Drive is a substantial side-by-side two-family property offering an exceptional combination of scale, flexibility, and income-producing potential in Derby. Built in 1985 and positioned on a 0.23-acre corner lot, this property delivers approximately 2,592 square feet above grade with 12 total rooms across two separate units. Each unit offers 3 bedrooms, creating an attractive six-bedroom multifamily configuration. The roof was recently replaced in 2022. Unit 509 features recently remodeled 2 full bathrooms with 1st flr bathroom having a jacuzzi tub and also connections for an additional half bath in the unfinished basement, hardwood floors, fireplace and a connection for a pellet stove in the unfinished basement and a recently updated back deck. Unit 511 features recently remodeled kitchen with hardwood floors, remodeled 1 full and 1 half bathrooms, semi-finished basement, newer Anderson windows, back door and screen door with transferrable warranties and a powered retractable awning over the updated back deck. Click on icon below main image for 3D virtual tour, floor plans and drone ariel view.
Key Facts
- City/Town
- Derby
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units are Side-by-Side
- Year Built
- 1985
- Days on Market
- 49 days
- Beds
- 6
- Baths
- 3 full · 1 half
- Living Area
- 2,592 sq ft
- Lot Size
- 0.23 acres
- Garage / Parking
- 4 total
- Property Taxes
- $9,130 / Annually
Market Snapshot
The Derby Market
Multi-Family · trailing 12 months
Active Listings
8
6 under contract
Median List Price
$492,400
8 active listings
Median Closed Price
$466,500
30 sales
Median Days on Market
59
8 active listings
Median $ / Sq Ft
$183
8 active listings
Sale-to-List Ratio
100.0%
30 sales
How this home compares
List Price
$575,000
vs $492,400 median
16.8% above median
Price / Sq Ft
$222
vs $183 median
21.3% above median
Days on Market
49 days
vs 59 days median
10 days fresher than median
Based on 8 active and 30 closed sales (trailing 12 mo) of multi-family in Derby. Source: SmartMLS · As of October 19, 2026.
Location
509-511 Roosevelt Drive, Derby, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$3,185
- Property Taxes$761
- Insurance$192
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Derby
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units are Side-by-Side
- Year Built
- 1985
- New Construction
- No/Resale
- Living Area
- 2,592 sq ft
Schools
- Elementary
- Irving
- High
- Derby
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- All Units Have Hook-UpsBasement Hook-Up(s)Washer/Dryer All Units
- Basement
- PartialFullUnfinishedHeatedFully FinishedPartial With HatchwayConcrete FloorFull With Hatchway
Exterior & Lot
- Lot Size
- 0.23 acres
- Zoning
- R-5
- Garage / Parking
- 4 total parking spacesPavedOff Street ParkingDrivewayPrivatePavedAsphalt
- Waterfront Details
- View
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Aluminum
- Color
- Brown
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGuttersGarden Area
- Lot Description
- Corner LotLevel Lot
Listing & Financials
- Property Taxes
- $9,130 / Annually
- Days on Market
- 49
- MLS #
- 24202817
- MLS Status
- Under Contract - Continue to Show
- Financing
- FHA,VA,CHFA
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 10/19/2026. 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 10/19/2026 at 11:55 PM UTC.