Antonio Ford

22 Evergreen Avenue

Westport, CT
$ 4,850,000 Beds 5 Baths 5 Sq 5,103
Monthly Estimate* How much can I afford?

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town. Despite its secluded setting, The Winslow Manor enjoys an unrivaled location just steps from everything that defines the Westport lifestyle. The Metro-North train, Levitt Pavilion, Compo Beach, the Westport Farmers Market, Longshore Golf Club, Cranberry Park, Sherwood Island State Park, the Westport Observatory, and Playhouse Square are all moments away, offering effortless access to culture, recreation, dining, and coastal living. Whether hosting unforgettable gatherings or enjoying quiet mornings overlooking the landscape, The Winslow Manor is more than a home - it's a sanctuary, a retreat, and a rare opportunity to own one of Westport's most captivating properties.

Single Family

  • Price
  • $ 4,850,000
  • City
  • Westport
  • Bedrooms
  • 5
  • Full Bathrooms
  • 5
  • County
  • Fairfield
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 2.52 Acres
  • Zip
  • 06880
  • Sqr Footage
  • 5,103
  • Year Built
  • 1949
  • Taxes
  • $ 27234
  • Style
  • MLS#
  • 24172211
Listed By: Valerie Alvarez 203-224-0361 with Serhant Connecticut, LLC. - (203) 489-7800
Data Source: Smart MLS

Features

General

Zoning A
Neighborhood In-Town
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.52
Directions Gps friendly. As you turn on Evergreen, it is the home all the way down the driveway. Approach the gate, wait for it to open, and continue down the driveway to the property.
High School Staples
City Westport
Elementary School Saugatuck
Sq Ft Total 5103
Year Built 1949
Style Colonial
Year Built Source Public Records
Pool Description Gunite,Heated,In Ground Pool

Interior Features

Cooling System Central Air,Zoned
Total Rooms 12
Basement Description Full,Storage,Fully Finished

Exterior Features

Water Source Public Water Connected
Lot Description Secluded,Interior Lot,Cleared,Professionally Landscaped,Water View,Open Lot

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Saugatuck Elementary School
Middle School Unknown Middle School
High School Staples High School

Price History

5/23/2026 Listed $4,850,000

Property vs Zip Code Average in 06880

Price
AVG $4.44M
$4.85M
Year Built
AVG 1983
1949

In The Neighborhood

Areas That We Cover

22 Evergreen Avenue Westport, CT is a Single Family Home for sale at $4850000 with 5103 sqft and a lot size of 2.52 Acres Acre(s). 22 Evergreen Avenue Westport has 5 bedrooms, 5 baths and was built in 1949. The property's zip code is 06880 which is in Westport, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

Antonio Ford

Antonio Ford

646-836-4274

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