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61 Clapboard Hill Road

Westport, Connecticut 06880

ACTIVE$3,795,000

Reduced from $3,850,000

Beds
4
Baths
3 | 1
SqFt
3,418
Acres
2.01
Year Built
1929
Matt Caiola

Matt Caiola

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2-Car Garage1 FireplacePrice Reduced

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

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$22,564

per 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.

Listed By

Lorelei Atwood

(203) 803-7600

Higgins Group Real Estate

(203) 254-9000

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.