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585 Winchester Avenue

New Haven, Connecticut 06511

PENDING$390,000
Beds
6
Baths
3
SqFt
4,098
Acres
0.11
Year Built
1900
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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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
1176 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

Median Days on Market

42

62 active listings

Median $ / Sq Ft

$212

62 active listings

Sale-to-List Ratio

100.1%

294 sales

How this home compares

List Price

$390,000

vs $599,450 median

34.9% below median

Price / Sq Ft

$95

vs $212 median

55.2% below median

Days on Market

1176 days

vs 42 days median

1134 days longer than median

Based on 62 active and 294 closed sales (trailing 12 mo) of multi-family in New Haven. Source: SmartMLS · As of July 29, 2026.

Location

585 Winchester Avenue, New Haven, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,118

per month

  • Principal & Interest$1,988
  • 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
1176
MLS #
170569039
MLS Status
Under Contract
Financing
FHA,VA,CHFA

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Lisa Cozzi

(860) 5082102

Berkshire Hathaway NE Prop.

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 7/29/2026. 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 7/29/2026 at 11:01 AM UTC.