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653 Winchester Avenue

New Haven, Connecticut 06511

ACTIVE$499,900
Beds
4
Baths
2 | 2
SqFt
1,855
Acres
0.13
Year Built
1900
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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1 Fireplace

About This Home

Beautifully restored historic Colonial offering the perfect blend of timeless character and thoughtful modern updates. Originally taken down to the studs and completely renovated by a respected local nonprofit, this home has since been beautifully redesigned and further upgraded by the current owners with exceptional attention to detail. The tastefully updated interior features an upgraded kitchen, four bedrooms, two full bathrooms, two half bathrooms and a fully finished walk up attic. Pride of ownership is evident throughout, from the recently painted exterior to the meticulously maintained living spaces. Outside, the property offers established gardens, greenhouse structures, and inviting outdoor spaces for gardening, entertaining, or simply enjoying the surroundings. Ideally located within walking distance of Science Park, the Farmington Canal Heritage Trail, and the exciting new retail and commercial developments transforming the Winchester Avenue corridor, this home combines historic charm, modern comfort, and outstanding convenience in one of New Haven's most dynamic neighborhoods.

Key Facts

City/Town
New Haven
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1900
Days on Market
17 days
Beds
4
Baths
2 full · 2 half
Living Area
1,855 sq ft
Lot Size
0.13 acres
Property Taxes
$7,185 / Annually

Market Snapshot

The New Haven Market

Single Family · trailing 12 months

Median Days on Market

30

47 active listings

Median $ / Sq Ft

$278

47 active listings

Sale-to-List Ratio

101.4%

280 sales

How this home compares

List Price

$499,900

vs $420,000 median

19.0% above median

Price / Sq Ft

$269

vs $278 median

In line with median

Days on Market

17 days

vs 30 days median

13 days fresher than median

Based on 47 active and 280 closed sales (trailing 12 mo) of single family in New Haven. Source: SmartMLS · As of July 28, 2026.

Location

653 Winchester Avenue, New Haven, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,315

per month

  • Principal & Interest$2,549
  • Property Taxes$599
  • Insurance$167
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
New Haven
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Colonial
Year Built
1900
New Construction
No/Resale
Living Area
1,855 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Other
Cooling
Window Unit
Fireplaces
1
Appliances
Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullUnfinished

Exterior & Lot

Lot Size
0.13 acres
Zoning
RM2
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Wood
Roof
Asphalt Shingle
Foundation
Stone
Lot Description
Lightly WoodedLevel LotProfessionally Landscaped

Listing & Financials

Property Taxes
$7,185 / Annually
Days on Market
17
MLS #
24189784
MLS Status
Active

Similar Properties

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

Listed By

Jacob Miller

(203) 589-7191

Huntsman,Meade & Partners Comp

(203) 777-2009

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.