555 Windsor Avenue
Stratford, Connecticut 06615
- Beds
- 3
- Baths
- 2
- SqFt
- 1,671
- Acres
- 0.11
- Year Built
- 1928
- Neighborhood
- Paradise Green
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
LOCATION! LOCATION! LOCATION! Welcome to 555 Windsor Avenue, nestled in Stratford's highly desirable Paradise Green neighborhood!** Discover the timeless charm and character of this beautiful Tudor-style home, offering 3-4 bedrooms, 2 full bathrooms, gorgeous hardwood floors throughout, and two inviting fireplaces that add warmth and elegance. The updated eat-in kitchen with SS appliances offers the perfect gathering space for everyday living and entertaining. New boiler, furnace, central air, siding. Additional highlights include a walk-up attic providing generous storage, a deck ideal for outdoor gatherings, a lovely yard with fruit trees, apples, raspberry, and grapes and numerous updates throughout. Enjoy the best of Paradise Green right at your doorstep! Take a leisurely stroll to the historic Paradise Green area, where you'll enjoy a vibrant neighborhood atmosphere, seasonal farmers markets, outdoor concerts, community celebrations, charming local shops, restaurants, cafes, and neighborhood conveniences. A commuter's dream! Conveniently located near the train station, public bus transportation, major highways, shopping centers, and everyday amenities, making travel and daily living a breeze. This home offers the perfect combination of classic architectural charm, modern conveniences, and an exceptional location in one of Stratford's most beloved neighborhoods. Don't miss this wonderful opportunity to call Paradise Green home! Coming Soon!
Key Facts
- City/Town
- Stratford
- Neighborhood
- Paradise Green
- Property / Style
- Single Family · Colonial,Tudor
- Year Built
- 1928
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full
- Living Area
- 1,671 sq ft
- Lot Size
- 0.11 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,665 / Annually
Market Snapshot
The Stratford Market
Single Family · trailing 12 months
Active Listings
71
80 under contract
Median List Price
$549,900
71 active listings
Median Closed Price
$480,000
434 sales
Median Days on Market
25
71 active listings
Median $ / Sq Ft
$298
71 active listings
Sale-to-List Ratio
101.4%
434 sales
How this home compares
List Price
$499,900
vs $549,900 median
9.1% below median
Price / Sq Ft
$299
vs $298 median
In line with median
Days on Market
0 days
vs 25 days median
25 days fresher than median
Based on 71 active and 434 closed sales (trailing 12 mo) of single family in Stratford. Source: SmartMLS · As of October 16, 2026.
Location
555 Windsor Avenue, Stratford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 15, 2026per month
- Principal & Interest$2,769
- Property Taxes$639
- Insurance$167
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Stratford
- Neighborhood
- Paradise Green
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Tudor
- Year Built
- 1928
- New Construction
- No/Resale
- Living Area
- 1,671 sq ft
Schools
- Elementary
- Wilcoxson
- Middle
- Per Board of Ed
- High
- Stratford
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- main level bathroom
- Appliances
- Electric Range
- Basement
- FullUnfinished
- Additional Rooms
- Bonus Room
Exterior & Lot
- Lot Size
- 0.11 acres
- Zoning
- RS-4
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Other
- Color
- light green
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- PorchDeck
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $7,665 / Annually
- Days on Market
- 0
- MLS #
- 24214855
- MLS Status
- Coming Soon
- Financing
- FHA,VA
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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 10/16/2026. 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 10/16/2026 at 5:15 AM UTC.