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509-511 Roosevelt Drive

Derby, Connecticut 06418

PENDING$575,000
Beds
6
Baths
3 | 1
SqFt
2,592
Acres
0.23
Year Built
1985
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,138

per 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

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Listed By

Ryzard Villa

(860) 549-6833

Premier Properties of CT

(860) 756-0980

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.