Storied and superbly restored, 'The Lookout' at 249 Greens Farms Rd blends the grandeur of a 1907 Colonial Revival with todays modern luxury. Privately set among perennial gardens and antique copper beeches, this iconic 16-room residence offers a gracious floor plan with elegant formal spaces, a chefs eat-in kitchen, media room, wine cellar, and inviting family areas. Original architectural details shine alongside impeccable updates. The primary suite features a spa bath and custom closets; three additional bedrooms offer flexible space. Outside, relax by a sparkling pool or host gatherings on the lush, landscaped lawn. The property includes an adjacent lot for added privacy or future expansion. A true Westport landmark, steps from town, schools, and rail, this is a rare opportunity to own an estate rich in character and comfort. Shown by appointment
Listed by Kim Harizman
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Compass Connecticut, LLC
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(917) 270-5168
Listed by Karen Scott
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Compass Connecticut, LLC
Last updated October 15, 2025
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Source: SmartMLS #24132302
Listing Facts
TypeSingle-family
NeighborhoodGreens Farms
Bedrooms7
Bathrooms9
Days on Prevu8
Taxes$35,498/year
Size10,104 sqft
Price per sqft$371
Location
Mortgage Calculator
Listing History
10/15/2025
Listed by Compass Connecticut, LLC
$3,750,000
Property Details for 249 Greens Farms Road
Exterior
Construction
New Construction: No/Resale
Roof: Asphalt Shingle
Year Built: 1907
Year Built Details: Public Records
Architectural Style: Victorian
Construction Materials: Frame, Stone, Concrete
Exterior Features: Porch-Wrap Around, Balcony, Underground Utilities, Porch, Wrap Around Deck, Gutters, Lighting, French Doors, Patio
Features
Pool Features: Gunite, Heated, Spa, In Ground Pool
Pool Private: Yes
Waterfront Features: Beach Rights, Water Community, View
Measurements
Lot Features: Fence - Partial, Additional Land Avail., Dry, Cleared, Professionally Landscaped
Lot Size Acres: 2.02
Financial
Taxes
Parcel Number: 415566
Tax Annual Amount: $35,498.00
Tax Year: 25
Interior
Features
Appliances: Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
Fireplaces Total: 4
Measurements
Living Area: 7,604
Rooms
Basement: Full, Partially Finished
Bathrooms Full: 6
Bathrooms Half: 3
Bathrooms Total Integer: 9
Bedrooms Total: 7
Rooms Total: 18
Parking
Parking
Attached Garage: Attached Garage, Under House Garage
Garage Spaces: 2
Schools
Elementary School
Elementary School: Greens Farms
High School
High School: Staples
Middle or Junior School
Middle Or Junior School: Bedford
Utilities
Equipment
Cooling: Central Air
Heating: Hot Air
Laundry Features: Upper Level
Sewer: Septic
Water Source: Public Water Connected
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