Storied and superbly restored, 'The Lookout' at 249 Greens Farms Rd blends the grandeur of a 1907 Victorian 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. An adjacent lot for added privacy or future expansion is also available. 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 December 07, 2025
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Source: SmartMLS #24132302
Listing Facts
TypeSingle-family
NeighborhoodGreens Farms
Bedrooms7
Bathrooms9
Days on Prevu57
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
Frequently Asked Questions
How many bedrooms and bathrooms does this single-family home have?
There are 7 bedrooms and 9 bathrooms in this single-family home at 249 Greens Farms Road.
What schools are nearby to 249 Greens Farms Road?
Nearby schools include the Greens Farms Elementary School, Bedford Middle School, and Staples High School.
Does this single-family home have parking?
Yes, there are 2 parking spaces available for 249 Greens Farms Road.
What are the annual taxes for 249 Greens Farms Road?
Annual taxes for this single-family home are estimated at $35,498.
How does 249 Greens Farms Road compare to other single-family homes in Greens Farms?
This single-family home is listed 40% below the average price for single-family homes in Greens Farms and has been on the market for 33 less days than the typical home in this area.
What is the square footage on this single-family home?
According to the MLS, this listing is 10,104 sqft.
249 Greens Farms Road is a 7-bedroom, 9-bath single-family home for sale in Westport CT 06880. On Prevu for 57 days at $3,750,000. This home features 10,104 square feet of living space, located in Greens Farms. The median listing price for single-family homes in this area is $4,999,000. Nearby schools include Greens Farms Elementary School, Bedford Middle School, and Staples High School. View other single-family home listings in Fairfield County.
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