653 Winchester Avenue
New Haven, Connecticut 06511
Reduced from $499,900
- Beds
- 4
- Baths
- 2 | 2
- SqFt
- 1,855
- Acres
- 0.13
- Year Built
- 1900
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
- 68 days
- Beds
- 4
- Baths
- 2 full · 2 half
- Living Area
- 1,855 sq ft
- Lot Size
- 0.13 acres
- Property Taxes
- $7,287 / Annually
Market Snapshot
The New Haven Market
Single Family · trailing 12 months
Active Listings
52
43 under contract
Median List Price
$392,700
52 active listings
Median Closed Price
$365,000
275 sales
Median Days on Market
64
52 active listings
Median $ / Sq Ft
$259
52 active listings
Sale-to-List Ratio
100.7%
275 sales
How this home compares
List Price
$449,900
vs $392,700 median
14.6% above median
Price / Sq Ft
$243
vs $259 median
6.2% below median
Days on Market
68 days
vs 64 days median
4 days longer than median
Based on 52 active and 275 closed sales (trailing 12 mo) of single family in New Haven. Source: SmartMLS · As of September 17, 2026.
Location
653 Winchester Avenue, New Haven, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$2,337
- Property Taxes$607
- Insurance$150
- 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
- $7,287 / Annually
- Days on Market
- 68
- MLS #
- 24189784
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/17/2026. 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 9/17/2026 at 4:20 AM UTC.