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
Sold for $3,480,000
$3,480,000
249 Greens Farms Road, Westport, CT 06880
7beds
10,104sqft
Single Family Residence
Built in 1907
2.02 Acres Lot
$3,554,600 Zestimate®
$344/sqft
$6,938 Estimated rent
Home value
$3,554,600
$3.20M - $3.95M
$6,938/mo
Zestimate® history
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List your homeWhat's special
Sparkling poolPrimary suiteOriginal architectural detailsAntique copper beechesMedia roomElegant formal spacesPerennial gardens
Zillow last checked:
Listing updated:
Listed by:
KMS Team at Compass,
Kim Harizman (917)270-5168,
Compass Connecticut, LLC 203-293-9715,
Co-Listing Agent: Karen Scott 203-613-9200,
Compass Connecticut, LLC
Bought with:
Zoe Hamann, RES.0808620
Compass Connecticut, LLC
Co-Buyer Agent: Carolyn Nally
Source: Smart MLS,MLS#: 24132302
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 9
- Full bathrooms: 6
- 1/2 bathrooms: 3
Primary bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Balcony/Deck, Full Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: High Ceilings, Balcony/Deck, Bedroom Suite, Full Bath, Hardwood Floor
- Level: Third,Other
Dining room
- Level: Main
Family room
- Features: Remodeled, Built-in Features, Dry Bar, Tile Floor
- Level: Lower
Great room
- Level: Main
Kitchen
- Level: Main
Living room
- Level: Main
Office
- Features: Bay/Bow Window, Hardwood Floor
- Level: Third,Other
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven, Microwave, Range Hood, Refrigerator, Freezer, Ice Maker, Dishwasher, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Upper Level
Features
- Doors: French Doors
- Basement: Full,Partially Finished
- Attic: Finished,Walk-up
- Number of fireplaces: 4
Interior area
- Total structure area: 10,104
- Total interior livable area: 10,104 sqft
- Finished area above ground: 7,604
- Finished area below ground: 2,500
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Features
- Patio & porch: Wrap Around, Porch, Patio
- Exterior features: Balcony, Rain Gutters, Lighting
- Has private pool: Yes
- Pool features: Gunite, Heated, Pool/Spa Combo, In Ground
- Fencing: Partial
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Beach Access, Water Community
Lot
- Size: 2.02 Acres
- Features: Additional Land Avail., Dry, Cleared, Landscaped
Details
- Parcel number: 415566
- Zoning: AAA
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Victorian
- Property subtype: Single Family Residence
Materials
- Shingle Siding, Stone
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1907
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Underground Utilities
Green energy
- Energy efficient items: Insulation, Thermostat
Community & HOA
Community
- Features: Golf, Health Club, Library, Medical Facilities, Park, Playground, Pool, Tennis Court(s)
- Subdivision: Greens Farms
HOA
- Has HOA: No
Location
- Region: Westport
Financial & listing details
- Price per square foot: $344/sqft
- Tax assessed value: $1,882,200
- Annual tax amount: $35,498
- Date on market: 10/15/2025
Price history
| Date | Event | Price |
|---|---|---|
| 4/16/2026 | Sold | $3,480,000-7.2%$344/sqft |
Source:  Smart MLS #24132302 Report a problem | ||
| 3/29/2026 | Pending sale | $3,750,000$371/sqft |
Source: Smart MLS #24132302 Report a problem | ||
| 10/15/2025 | Listed for sale | $3,750,000+2.7%$371/sqft |
Source: Smart MLS #24132302 Report a problem | ||
| 12/26/2006 | Sold | $3,650,000+595.2%$361/sqft |
Source: Public Record Report a problem | ||
| 3/2/2000 | Sold | $525,000+61.5%$52/sqft |
Source: Public Record Report a problem | ||
| 10/29/1999 | Sold | $325,000-1.5%$32/sqft |
Source: Public Record Report a problem | ||
| 8/7/1987 | Sold | $330,000$33/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $35,498 +1.3% | $1,882,200 |
| 2024 | $35,047 +1.5% | $1,882,200 |
| 2023 | $34,538 +1.5% | $1,882,200 |
| 2022 | $34,011 | $1,882,200 |
| 2021 | $34,011 +10% | $1,882,200 +1.8% |
| 2020 | $30,910 -0.9% | $1,849,800 |
| 2019 | $31,188 | $1,849,800 |
| 2018 | $31,188 | $1,849,800 |
| 2017 | $31,188 | $1,849,800 |
| 2016 | $31,188 | $1,849,800 |
Find assessor info on the county website
Neighborhood: Greens Farms
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Nearby schools
GreatSchools rating
- 10/10Green's Farms SchoolGrades: K-5Distance: 1.1 mi
- 9/10Bedford Middle SchoolGrades: 6-8Distance: 2.5 mi
- 10/10Staples High SchoolGrades: 9-12Distance: 2.3 mi
Schools provided by the listing agent
- Elementary: Greens Farms
- Middle: Bedford
- High: Staples
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Fairfield County
- Westport
- 06880
- Greens Farms
- 249 Greens Farms Road
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