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22 Evergreen Avenue

Westport, CT 06880
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Bed 5

Bed

Bath 5

Bath

SqFt5,103

Sqft

Acres2.52

Acres(Lot)

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.

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Detail Ic Property Details

Property Type : Residential

Price : $4,850,000

AD Id : 79189700

MLS Id : 24172211

Beds : 5

Lot Size : 2.52 Acres

Living Area Size : 5,103 Sq. Ft

Tax Amount : $27,234

Year Built : 1949

Garage : 2

County : Fairfield

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Feature Features

  • Bedroom Information

    Total beds: 5

    Bathroom Information

    Total Baths: 5 Full Baths: 5

    Room Information

    Rooms Total: 12 Has Basement: Yes Basement: Full, Finished, Storage Space
  • Roofing Information

    Wood
  • Interior Features

    Roof: Wood Appliances: Dishwasher, Gas Range, Refrigerator, Electric Water Heater, Range Hood
  • Heating & Cooling

    Has Heating: Yes Heating: Oil, Forced Air Has Cooling: Yes Cooling: Central Air, Zoned

  • Building Information

    Year Built: 1949 Building Area Total: 5103 Construction Materials: Cedar, Stone, Frame Patio And Porch Features: Patio Pool Features: Gunite, Heated, Outdoor Pool, In Ground Private Pool: No Water front Features: Beach Access View: Water
  • Exterior Features

    Exterior Features: Balcony

  • Lot Information

    Lot Size Acres: 2.52 Lot Description: Cleared

  • Listing Price Information

    Listing Price: $4850000

  • Tax Information

    Parcel Number: 412172 Annual Tax: $27234

  • Parking Information

    Parking Total: 10 Gravel, Private, Other, Driveway

    Garage Information

    Has Garage: Yes Garage Space: 2

  • School Information

    Elementary School: Saugatuck
    Junior High School: Bedford
    Senior High School: Staples
  • Location Information

    Direction: 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. WaterSource: Public
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
28 Bulkley Avenue, Westport, CT, 06880 $2,350,000 5 5 5,793 0.50 Acre
69 Beachside Avenue, Westport, CT, 06880 $7,350,000 6 7 6,585 4 Acres
61 Clapboard Hill Road, Westport, CT, 06880 $3,698,000 4 4 3,418 2.01 Acres
11 Beachside Common, Westport, CT, 06880 $22,825,000 8 10 12,946 2.60 Acres
20 Turkey Hill Circle, Westport, CT, 06880 $7,250,000 5 9 9,648 1.77 Acres
25 Bauer Pl Extension, Westport, CT, 06880 $2,250,000 4 3 2,900 0.27 Acre
10 Mary Jane Lane, Westport, CT, 06880 $5,990,000 6 7 6,900 1.06 Acres
21 Sturges Commons, Westport, CT, 06880 $6,250,000 6 9 10,521 1 Acre
Clapboard Hill Road #NE.., Westport, CT, 06880 $7,926,000 6 7 7,200 2 Acres
22 Dawn Drive, Westport, CT, 06880 $4,995,700 4 5 4,000 1.50 Acres

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

ByOwner last updated this listing 10/04/2026 @ 20:27

MLS: 24172211 LISTED BY: Valerie Alvarez, Serhant Connecticut, LLC SOURCE: SmartMLS

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