About the Home
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.
Rooms & Interior
Room Details
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Office (Main Level)
9 ft+ Ceilings, Beams, Book Shelves, Built-Ins, Hardwood Floor
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Full Bath (Main Level)
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Primary Br Suite (Upper Level)
9 ft+ Ceilings, Balcony/Deck, French Doors, Steam/Sauna, Walk-In Closet, Hardwood Floor
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Bedroom (Upper Level)
Book Shelves, Built-Ins, Hardwood Floor
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Bedroom (Other Level)
Built-Ins, On 3rd Floor
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Formal Dining Room (Main Level)
9 ft+ Ceilings, French Doors, Patio/Terrace, Hardwood Floor
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Den (Main Level)
Book Shelves, Built-Ins, Hardwood Floor
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Bedroom (Upper Level)
Book Shelves, Built-Ins, Full Bath, Hardwood Floor
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Rec/Play Room (Lower Level)
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Library (Main Level)
Balcony/Deck, Beams, Book Shelves, Built-Ins, French Doors, Hardwood Floor
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Den (Main Level)
Book Shelves, Built-Ins, Hardwood Floor
-
Bedroom (Upper Level)
Book Shelves, Built-Ins, Full Bath, Hardwood Floor
-
Rec/Play Room (Lower Level)
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Library (Main Level)
Balcony/Deck, Beams, Book Shelves, Built-Ins, French Doors, Hardwood Floor
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Great Room (Main Level)
Bay/Bow Window, 9 ft+ Ceilings, Beams, Built-Ins, Fireplace, Hardwood Floor
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Kitchen (Main Level)
9 ft+ Ceilings, Beams, Built-Ins, Island, Pantry, Hardwood Floor
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Bedroom (Main Level)
Hardwood Floor
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Full Bath (Upper Level)
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Full Bath (Upper Level)
Home Features
Heating
- Fireplaces: 1
- Heating: hot air
- Heat fuel type: oil
- Fuel tank: in basement
Appliances
- Gas range
- Range hood
- Refrigerator
- Dishwasher
Attic
- Storage space
- Finished
- Walk-up
Basement
- Full
- Storage
- Fully finished
Exterior Features
- Balcony
- Awnings
- Stone wall
- French doors
- Patio
Property Details
Parking
- Garage spaces: 3
- Under house garage
- Other
- Driveway
Swimming Pool
- Gunite
- Heated
- In ground pool
Lot Details
- Lot surface: 2.52 acres
- Secluded
- Interior lot
- Cleared
- Professionally landscaped
- Water view
- Open lot
Utilities
- Water: public water connected
- Sewage: pub. sewer connected
Near-by Amenities
- Basketball court
- Golf course
- Library
- Park
- Private school(s)
- Shopping/mall
- Tennis courts
Construction Details
- Style
- colonial
- Construction year
- 1949
- Exterior Siding
- cedar, stone
- Foundation
- concrete
- Roof
- wood shingle
Area & Town
This home is located in In-Town neighborhood, in the town of Westport.
- $1.65M med. price
- 12 homes for sale
- $2.09M med. price
- 99 homes for sale
Finance & Listing Info
| Status |
Coming soon |
| Listing date |
May 23, 2026 |
| List price |
$ 4,850,000 |
| Current price |
$ 4,850,000 |
| Tax amount |
$ 27,234 |
| Tax year |
july 2025-june 2026 |
| MLS ID |
#24172211 |
| List Agent |
Valerie Alvarez |
| Co-List Agent |
Carmen Desiato |
| List Office |
Serhant Connecticut, LLC |
| Co-List Office |
serhant connecticut, llc |
(c) 2026 Based on information provided to and compiled by the Smart MLS, Inc.
22 Evergreen Avenue
Home Photos