380 Orange Avenue
Milford, Connecticut 06461
- Beds
- 6
- Baths
- 2
- SqFt
- 3,360
- Acres
- 1.01
- Year Built
- 1880
- 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
Beautifully updated and incredibly versatile, this two family home is currently operating as a highly successful Airbnb and can easily be converted back to a spacious single family residence. Situated on a beautiful lot, the property includes a separate barn with a one car garage. Both ranch style units are bright and well maintained. The first floor offers an updated kitchen with quartz countertops, a door to the deck, a fully renovated bath with a walk in shower, three bedrooms, a spacious living room, and hardwood floors throughout. The upper unit also features three bedrooms with hardwood floors, a bright kitchen with sliders to a private deck, and comfortable living space. Each unit has its own washer and dryer. The finished third floor provides additional flexible living space ideal for a home office, playroom, or guest area. Additional features include vinyl siding, newer windows, newer decks, and well maintained mechanicals. The 2 units are connected by a center staircase making conversion to a single family very easy. The home can be sold furnished, making it a true turnkey investment or owner occupied opportunity. Conveniently located near downtown, shopping, restaurants, train service, and major highways. Enjoy the beautiful yard in every season.
Key Facts
- City/Town
- Milford
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1880
- Days on Market
- 7 days
- Beds
- 6
- Baths
- 2 full
- Living Area
- 3,360 sq ft
- Lot Size
- 1.01 acres
- Garage / Parking
- 1 garage · 6 total
- Property Taxes
- $10,537 / Annually
Market Snapshot
The Milford Market
Multi-Family · trailing 12 months
Active Listings
2
Milford inventory
Median List Price
$822,000
2 active listings
Median Closed Price
$731,100
15 sales
Median Days on Market
14
2 active listings
Median $ / Sq Ft
$250
2 active listings
Sale-to-List Ratio
97.3%
15 sales
How this home compares
List Price
$975,000
vs $822,000 median
18.6% above median
Price / Sq Ft
$290
vs $250 median
16.0% above median
Days on Market
7 days
vs 14 days median
7 days fresher than median
Based on 2 active and 15 closed sales (trailing 12 mo) of multi-family in Milford. Source: SmartMLS · As of July 28, 2026.
Location
380 Orange Avenue, Milford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,971
- Property Taxes$878
- Insurance$325
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Milford
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Multi-Family
- Subtype
- Duplex
- Style
- Units on different Floors
- Year Built
- 1880
- New Construction
- No/Resale
- Living Area
- 3,360 sq ft
Schools
- Elementary
- Orange Avenue
- High
- Joseph A. Foran
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Laundry
- Hook-Up In Unit 1Hook-Up In Unit 2
- Laundry Location
- In unit
- Basement
- FullUnfinishedHatchway Access
Exterior & Lot
- Lot Size
- 1.01 acres
- Zoning
- R30
- Garage / Parking
- 1 garage space6 total parking spacesBarnPavedOff Street ParkingDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Exterior Features
- PorchBarnDeckGuttersLighting
- Lot Description
- Rolling
Listing & Financials
- Property Taxes
- $10,537 / Annually
- Days on Market
- 7
- MLS #
- 24189957
- MLS Status
- Active
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 4:25 AM UTC.