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$499,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,671 Sq. Ft.
  • 2 Car Garage
  • Updated 11 hours ago

Next open house:

Open House: 1:00 PM - 3:00 PM

Saturday 10/24 1:00 PM - 3:00 PM

555 Windsor Avenue,Stratford, CT 06614

555 Windsor AvenueStratfordCT06614

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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! Open House this weekend

Full Property Details for 555 Windsor Ave

General

  • Price: $499,900
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24214855
  • Updated: 10/20/2026
  • Added to Site: 6 day(s) ago

Interior

  • Number of Rooms: 7
  • Rooms/Areas: Bonus Room
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Electric Range

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3
  • Primary Bedroom: Primary Bedroom - Fireplace, Hardwood Floor, Upper
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Ceiling Fan, Fireplace, Hardwood Floor, Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Porch, Deck
  • Color: light green

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Detached Garage

Location

  • County: Fairfield
  • Neighborhood: Paradise Green
  • Driving Directions: Main Street to Windsor Ave

School Information

  • Elementary School: Wilcoxson
  • Middle School: Wooster
  • Intermediate School: Per Board of Ed
  • High School: Stratford

Community

  • Community Name: Paradise Green

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, 40 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial, Tudor
  • Construction Status: No/Resale
  • Exterior Const.: Other
  • Basement Desc.: Full, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 1,671
  • Above Ground: 1,671 Sq. Ft.
  • Year Built: 1928

Lot Features

  • Lot Size (Acres): 0.11
  • Zoning: RS-4
  • Lot Description: Level Lot

Water Features

  • Water Front Desc.: Beach Rights

Green Features

  • Energy Features: Active Solar

Financial Considerations

  • Assessment Amount: $327,320
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 381715

Listed by Higgins Group Real Estate, The Vanderblue Team at Higgins Group, Vera Maximin

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Listing agent

— 555 Windsor Ave —

  • Vera Maximin

    Higgins Group Real Estate

Agent Contact: (203) 243-4841 Office Contact: (203) 254-9000

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 555 Windsor Ave

School District:Stratford School District
NameGradesDistance
Wilcoxson School
600 Wilcoxson Avenue, Stratford, CT 06614
K-60.3 mi
David Wooster Middle School
150 Lincoln Street, Stratford, CT 06615
7-80.7 mi
Stratford High School
245 King Street, Stratford, CT 06615
9-121 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 555 Windsor Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/20/2026
Listed
$499,900
86.53%
MLS
5/14/2015
Sold
$268,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 555 Windsor Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,665
—
$190,680
—
2023
$7,665
2%
$190,680
—
2022
$7,524
—
$190,680
—
2021
$7,526
—
$190,680
—
2020
$7,559
-2%
$190,680
-2%
2019
$7,728
—
$193,830
—
2018
$7,734
3%
$193,830
3%
2017
$7,521
3%
$188,160
—
2016
$7,336
6%
$188,160
1%
2015
$6,914
10%
$186,970
6%
2014
$6,303
3%
$176,890
—
2011
$6,127
—
$176,890
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 555 Windsor Ave

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Higgins Group Real Estate, The Vanderblue Team at Higgins Group, Vera Maximin

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555 Windsor Avenue, Stratford, CT 06614 (MLS# 24214855) is a Single Family property with 3 bedrooms and 2 full bathrooms. 555 Windsor Avenue is currently listed for $499,900 and was received on October 15, 2026. Want to learn more about 555 Windsor Avenue? Do you have questions about finding other Single Family real estate for sale in Stratford? You can browse all Stratford real estate or contact a Coldwell Banker agent to request more information.

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