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$4,850,000 Coming Soon

  • For Sale
  • Coming Soon
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 5,103 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago
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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.

Full Property Details for 22 Evergreen Ave

General

  • Price: $4,850,000
  • Taxes: (July 2025-June 2026)
  • Status: Coming Soon
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24172211
  • Updated: 5/24/2026
  • Added to Site: 3 day(s) ago
  • Expected Market Date: 5/29/2026

Interior

  • Number of Rooms: 12
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Range, Range Hood, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5
  • Full Bath: Main

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: 9 ft+ Ceilings, Balcony/Deck, French Doors, Steam/Sau, Upper
  • Bedroom 1: Bedroom - Hardwood Floor, Main
  • Bedroom 2: Bedroom - Built-Ins, On 3rd Floor, Other
  • Bedroom 3: Bedroom - Book Shelves, Built-Ins, Full Bath, Hardwood Floor, Upper
  • Bedroom 4: Bedroom - Book Shelves, Built-Ins, Hardwood Floor, Upper

Other Rooms

  • Great Room: Great Room - Bay/Bow Window, 9 ft+ Ceilings, Beams, Built-Ins, Fireplace, Hardwood Floor, Main
  • Kitchen: Kitchen - 9 ft+ Ceilings, Beams, Built-Ins, Island, Pantry, Hardwood Floor, Main
  • Formal Dining Room: Formal Dining Room - 9 ft+ Ceilings, French Doors, Patio/Terrace, Hardwood Floor, Main
  • Office: Office - 9 ft+ Ceilings, Beams, Book Shelves, Built-Ins, Hardwood Floor, Main
  • Den: Den - Book Shelves, Built-Ins, Hardwood Floor, Main
  • Library: Library - Balcony/Deck, Beams, Book Shelves, Built-In, Main
  • Game room: Yes
  • Game Room: Rec/Play Room, Lower
  • Rec Room: Lower

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, In Ground Pool

Exterior

  • Exterior Features: Balcony, Awnings, Stone Wall, French Doors, Patio

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 10
  • Parking: Under House Garage, Other, Driveway

Location

  • County: Fairfield
  • Neighborhood: In-Town
  • Driving 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.

School Information

  • Elementary School: Saugatuck
  • Middle School: Bedford
  • High School: Staples

Community

  • Community Name: In-Town

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Electric, Domestic

Utilities

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

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Cedar, Stone
  • Basement Desc.: Full, Storage, Fully Finished
  • Roof: Wood Shingle
  • Attic: Yes
  • Square Feet: 5,103
  • Above Ground: 4,377 Sq. Ft.
  • Below Ground: 726 Sq. Ft.
  • Year Built: 1949

Lot Features

  • Lot Size (Acres): 2.52
  • Driveway/Sidewalk: Private, Crushed Stone
  • Zoning: A
  • Lot Description: Secluded, Interior Lot, Cleared, Professionally Landscaped, Water View, Open Lot

Water Features

  • Water Front Desc.: Beach Rights, Water Community

Financial Considerations

  • Assessment Amount: $1,444,000
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 412172

Listed by Serhant Connecticut, LLC, Valerie Alvarez and Serhant Connecticut, LLC, Carmen Desiato

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Listing agents

— 22 Evergreen Ave —

  • Valerie Alvarez

    Serhant Connecticut, LLC

  • Carmen Desiato

    Serhant Connecticut, LLC

Agent Contact: (203) 224-0361 Office Contact: (203) 489-7800

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 22 Evergreen Ave

School District:Westport School District
NameGradesDistance
Saugatuck Elementary School
170 Riverside Avenue, Westport, CT 06880
K-50.9 mi
Bedford Middle School
88 North Avenue, Westport, CT 06880
6-81.7 mi
Staples High School
70 North Avenue, Westport, CT 06880
9-121.6 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 22 Evergreen Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/23/2026
Listed
$4,850,000
260.86%
MLS
7/31/1995
Sold
$1,344,000
—
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 22 Evergreen Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$27,234
1%
$1,444,000
—
2023
$26,887
1%
$1,444,000
—
2023
$26,497
2%
$1,444,000
—
2022
$26,093
—
$1,444,000
—
2021
$26,093
4%
$1,444,000
-4%
2020
$25,159
-1%
$1,505,600
—
2019
$25,384
—
$1,505,600
—
2018
$25,384
—
$1,505,600
—
2017
$25,384
—
$1,505,600
—
2016
$25,384
-5%
$1,505,600
2%
2015
$26,657
1%
$1,473,600
—
2014
$26,436
-1%
$1,473,600
—
2011
$26,628
—
$1,473,600
—
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 22 Evergreen 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 Serhant Connecticut, LLC, Valerie Alvarez and Serhant Connecticut, LLC, Carmen Desiato

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22 Evergreen Avenue, Westport, CT 06880 (MLS# 24172211) is a Single Family property with 5 bedrooms and 5 full bathrooms. 22 Evergreen Avenue is currently listed for $4,850,000 and was received on May 23, 2026. Want to learn more about 22 Evergreen Avenue? Do you have questions about finding other Single Family real estate for sale in Westport? You can browse all Westport real estate or contact a Coldwell Banker agent to request more information.

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