585 Winchester Avenue
New Haven, Connecticut 06511
- Beds
- 6
- Baths
- 3
- SqFt
- 4,098
- Acres
- 0.11
- Year Built
- 1900
- Property Type
- 3 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
Amazing opportunity for a huge 3 unit asset in Newhallville on a tree lined street & is walking distance to Yale Divinity School, Science Park and Albertus Magnus College! This opportunity allows you to choose your tenants, which eliminates any arrears in rent collections. Rents for 3 beds remodeled with quality finishes are leasing at $1700+. The utilities are paid by the tenants. Water is paid by the Owner. The surrounding properties in the neighborhood have been remodeled with loads of character. The property has ample off street parking. 2 units have 3 beds & 1 bath and 1 units has 4 beds & 1 bath. Subpanels are in the units and electrical is updated to circuit breakers. Windows are newer and the flooring is wood, vinyl & ceramic tile. There are back porches on the property and ample parking. There is a Police Substation across the street.
Key Facts
- City/Town
- New Haven
- Property Type
- Multi-Family
- Year Built
- 1900
- Days on Market
- 1276 days
- Beds
- 6
- Baths
- 3 full
- Living Area
- 4,098 sq ft
- Lot Size
- 0.11 acres
- Property Taxes
- Not on file from MLS
Market Snapshot
The New Haven Market
Multi-Family · trailing 12 months
Active Listings
63
56 under contract
Median List Price
$599,900
63 active listings
Median Closed Price
$500,000
296 sales
Median Days on Market
54
63 active listings
Median $ / Sq Ft
$211
63 active listings
Sale-to-List Ratio
100.2%
296 sales
How this home compares
List Price
$390,000
vs $599,900 median
35.0% below median
Price / Sq Ft
$95
vs $211 median
55.0% below median
Days on Market
1276 days
vs 54 days median
1222 days longer than median
Based on 63 active and 296 closed sales (trailing 12 mo) of multi-family in New Haven. Source: SmartMLS · As of November 6, 2026.
Location
585 Winchester Avenue, New Haven, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$2,114
- Property Taxes$0
- Insurance$130
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- New Haven
- County
- New Haven
Residence
- Property Type
- Multi-Family
- Subtype
- 3 Family
- Year Built
- 1900
- Living Area
- 4,098 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Cooling
- None
Exterior & Lot
- Lot Size
- 0.11 acres
- Garage / Parking
- DrivewayOff Street Parking
- Waterfront Details
- Not Applicable
- Construction
- ShingleVinyl Siding
- Roof
- Other
- Foundation
- Concrete
- Exterior Features
- GuttersLightingPorchSidewalk
- Lot Description
- Level Lot
Listing & Financials
- Days on Market
- 1276
- MLS #
- 170569039
- MLS Status
- Under Contract
- Financing
- FHA,VA,CHFA
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Maddy Ceruti
Berkshire Hathaway NE Prop.
Buyer's Agent
Eric J. Allen
Chess Real Estate Services
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/6/2026. 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 11/6/2026 at 3:10 AM UTC.