61 Clapboard Hill Road
Westport, Connecticut 06880
Reduced from $3,850,000
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,418
- Acres
- 2.01
- Year Built
- 1929
- Neighborhood
- Greens Farms
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private gates on expansive, picturesque grounds, the property is surrounded by multimillion-dollar estates-making it an exceptional canvas for new construction or a significant estate expansion. The existing home is beautifully renovated, offering flexibility with gracious living and dining rooms, a sun-filled sunroom, cozy family room, and a curated Chef's kitchen with Calacatta marble, bespoke cabinetry, and top-tier appliances. A serene Primary Suite and additional bedrooms upstairs, the home functions perfectly as-is-or as a future guest house or accessory residence with thoughtful modifications. The sweeping land provides ample room for a new main residence set further back on the property, while maintaining the current home for extended family, guests, staff, or as a pool house. Outdoor living is equally compelling, with an expansive covered stone terrace, fire pit, and open meadow-like grounds offering endless possibilities for a pool, tennis court, barn, or gardens. Whether you choose to embrace the home's timeless appeal or create a legacy estate tailored to your vision, this is a unique chance to live comfortably now while building for tomorrow-all in one of Westport's most coveted locations, just minutes to Westport's vibrant downtown with award winning restaurants, premium shopping, beaches, and train.
Key Facts
- City/Town
- Westport
- Neighborhood
- Greens Farms
- Property / Style
- Single Family · Mediterranean,Colonial
- Year Built
- 1929
- Days on Market
- 86 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 3,418 sq ft
- Lot Size
- 2.01 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $23,386 / Annually
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
71
56 under contract
Median List Price
$4.60M
71 active listings
Median Closed Price
$2.42M
303 sales
Median Days on Market
56
71 active listings
Median $ / Sq Ft
$820
71 active listings
Sale-to-List Ratio
100.0%
303 sales
How this home compares
List Price
$3.79M
vs $4.60M median
17.5% below median
Price / Sq Ft
$1,110
vs $820 median
35.4% above median
Days on Market
86 days
vs 56 days median
30 days longer than median
Based on 71 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.
Location
61 Clapboard Hill Road, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$19,350
- Property Taxes$1,949
- Insurance$1,265
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Westport
- Neighborhood
- Greens Farms
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Mediterranean,Colonial
- Year Built
- 1929
- New Construction
- No/Resale
- Living Area
- 3,418 sq ft
Schools
- Elementary
- Greens Farms
- High
- Staples
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central AirZoned
- Fireplaces
- 1
- Laundry Location
- Main Level
- Appliances
- Gas RangeMicrowaveRange HoodRefrigeratorFreezerDishwasherWasherDryerWine Chiller
- Basement
- PartialUnfinishedSump PumpStorageInterior AccessConcrete Floor
- In-Law Apartment
- No
- Interior Features
- Auto Garage Door OpenerCable - AvailableSecurity System
- Additional Rooms
- Laundry RoomMud Room
Exterior & Lot
- Lot Size
- 2.01 acres
- Zoning
- AAA
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Beach RightsWater Community
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Stucco
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Fence - WoodFence - FullDryLevel LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $23,386 / Annually
- Days on Market
- 86
- MLS #
- 24171986
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Julie Vanderblue
Higgins Group Real Estate
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/27/2026 at 10:50 AM UTC.