22 Evergreen Avenue, Westport, Connecticut

$4,850,000

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5

Beds

5

Baths

5,103

Square feet

2.52

Acres

About 22 Evergreen Avenue

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.

Features of 22 Evergreen Avenue

MLS® # 24172211
Price $4,850,000
Bedrooms 5
Bathrooms 5.00
Full Baths 5
Square Footage 5,103
Acres 2.52
Type Single Family For Sale
Style Colonial
Status Active

Community Information

Address 22 Evergreen Avenue
Area In-Town
City Westport
County Fairfield
State Connecticut
Zip Code 06880

Amenities

Parking Spaces 10
Parking Under House Garage, Other, Driveway
# of Garages 2
Is Waterfront No
Waterfront Beach Rights, Water Community
Has Pool Yes
Pool Gunite, Heated, In Ground Pool

Interior

Appliances Gas Range, Range Hood, Refrigerator, Dishwasher
Heating Hot Air, Oil
Cooling Central Air, Zoned
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Full, Storage, Fully Finished

Exterior

Exterior Cedar, Stone
Exterior Features Balcony, Awnings, Stone Wall, French Doors, Patio
Lot Description Secluded, Interior Lot, Cleared, Professionally Landscaped, Water View, Open Lot
Roof Wood Shingle
Foundation Concrete

School Information

Elementary Saugatuck
Middle Bedford
High Staples

Additional Information

Date Listed May 23rd, 2026
Days on Market 101
Zoning A
RE / Bank Owned No

Listing Details

OfficeSerhant Connecticut, LLC

Listing Map

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