Generously sited on 2.15 stunning acres in Greens Farms, the Joseph H. Wakeman House is a perfect example of New England ingenuity and warmth. Built in 1840, this distinguished Federal-style residence was thoughtfully reimagined in the 1930s by an owner intent on showcasing its craftsmanship and enduring quality. The current residents were similarly captivated by its character and history. Located in the heart of one of Westport's most coveted and convenient neighborhoods, the park-like grounds, with sweeping lawns and meandering stone walls, are enchanting in every season. Inside, the home is warm and inviting-walls painted in pristine white provide a clean backdrop that highlights architectural details and period millwork. Wideboard flooring and 9-foot ceilings extend throughout, underscoring the timeless proportions and charm. Welcomed through double front doors, guests are immediately drawn to the gracious front hall or library, lined with bookshelves and anchored by the home's original staircase - a space so inviting, it is hard to leave. The elegant LR, with its rare double fireplaces, easily accommodates a grand piano, while the intimate formal DR-also with a fireplace, encourages evenings when friends linger. A butler's pantry connects seamlessly to the gourmet kitchen, which opens to the terrace and is bathed in natural light.The spacious FR features wide French doors to the yard, while a charming mudroom offers a practical yet welcoming entry. Throughout, greenery and garden views blur the line between inside and out. Upstairs, the second floor is anchored by a tranquil primary suite with an exquisite new bathroom. Four additional BRs provide comfort and flexibility for family or guests. The third floor offers its own sense of retreat, with a bunkroom, full bath, and a cheerful playroom. Outbuildings include a separate garage with custom-made doors, a barn, a corn crib and garden shed. Southport Harbor and beach are both within walking distance. This is a timeless, magical home; come to see it and feel some Westport's early history.
Sold for $3,850,000
$3,850,000
365 Greens Farms Road, Westport, CT 06880
6beds
4,420sqft
Single Family Residence
Built in 1840
2.12 Acres Lot
$3,914,200 Zestimate®
$871/sqft
$7,867 Estimated rent
Home value
$3,914,200
$3.52M - $4.34M
$7,867/mo
Zestimate® history
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List your homeWhat's special
Zillow last checked: 7 hours ago
Listing updated: November 11, 2025 at 04:57am
Listed by:
KMS Team at Compass,
Michael Mombello (203)505-4477,
Compass Connecticut, LLC 203-293-9715,
Co-Listing Agent: Lynne Nolan 703-906-3003,
Compass Connecticut, LLC
Bought with:
Veronica A. Monahan, RES.0776529
Compass Connecticut, LLC
Source: Smart MLS,MLS#: 24124482
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: Full Bath, Walk-In Closet(s), Wide Board Floor
- Level: Upper
Bedroom
- Features: Wide Board Floor
- Level: Upper
Bedroom
- Features: Wide Board Floor
- Level: Upper
Bedroom
- Features: Wide Board Floor
- Level: Upper
Bedroom
- Features: Wide Board Floor
- Level: Other
Bedroom
- Features: Skylight, Beamed Ceilings, Full Bath, Wide Board Floor
- Level: Third,Upper
Bathroom
- Features: Tile Floor
- Level: Main
Bathroom
- Level: Upper
Bathroom
- Level: Upper
Dining room
- Features: High Ceilings, Fireplace, Wide Board Floor
- Level: Main
Family room
- Features: French Doors, Wide Board Floor
- Level: Main
Kitchen
- Features: High Ceilings, French Doors, Kitchen Island, Pantry, Patio/Terrace, Wide Board Floor
- Level: Main
Living room
- Features: High Ceilings, Fireplace, Wide Board Floor
- Level: Main
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven, Refrigerator, Subzero, Dishwasher, Disposal, Washer, Dryer, Water Heater
- Laundry: Main Level, Mud Room
Features
- Sound System, Wired for Data, Entrance Foyer
- Doors: French Doors
- Basement: Full,Unfinished,Storage Space,Hatchway Access,Interior Entry,Concrete
- Attic: Storage,Finished,Walk-up
- Number of fireplaces: 5
Interior area
- Total structure area: 4,420
- Total interior livable area: 4,420 sqft
- Finished area above ground: 4,420
Property
Parking
- Total spaces: 2
- Parking features: Detached, Garage Door Opener
- Garage spaces: 2
Features
- Patio & porch: Patio, Porch
- Exterior features: Rain Gutters, Garden, Stone Wall, Underground Sprinkler
- Waterfront features: Beach Access
Lot
- Size: 2.12 Acres
- Features: Few Trees, Wooded, Level, Landscaped
Details
- Additional structures: Barn(s), Shed(s)
- Parcel number: 415868
- Zoning: AAA
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Antique
- Property subtype: Single Family Residence
Materials
- Clapboard, Wood Siding
- Foundation: Masonry, Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1840
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Golf, Library, Medical Facilities, Park, Private School(s), Public Rec Facilities, Shopping/Mall, Tennis Court(s)
Location
- Region: Westport
- Subdivision: Greens Farms
Price history
| Date | Event | Price |
|---|---|---|
| 11/10/2025 | Sold | $3,850,000+1.3%$871/sqft |
Source:  Smart MLS #24124482 Report a problem | ||
| 10/2/2025 | Pending sale | $3,800,000$860/sqft |
Source: Smart MLS #24124482 Report a problem | ||
| 9/18/2025 | Listed for sale | $3,800,000+54.5%$860/sqft |
Source: Smart MLS #24124482 Report a problem | ||
| 12/1/2021 | Sold | $2,459,500-8.1%$556/sqft |
Source: Smart MLS #170399108 Report a problem | ||
| 9/10/2021 | Contingent | $2,675,000$605/sqft |
Source: Smart MLS #170399108 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $24,846 +1.3% | $1,317,400 |
| 2024 | $24,530 +1.5% | $1,317,400 |
| 2023 | $24,174 +2.3% | $1,317,400 +0.7% |
Find assessor info on the county website
Neighborhood: Greens Farms
Nearby schools
GreatSchools rating
- 9/10Green's Farms SchoolGrades: K-5Distance: 1.2 mi
- 8/10Bedford Middle SchoolGrades: 6-8Distance: 2.2 mi
- 10/10Staples High SchoolGrades: 9-12Distance: 2 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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$3,914,200
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- Connecticut
- Fairfield County
- Westport
- 06880
- Greens Farms
- 365 Greens Farms Road