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38 Prospect Road

Westport, Connecticut 06880

ACTIVE$9,200,000
Beds
6
Baths
6 | 3
SqFt
8,623
Acres
1.19
Year Built
2026
Matt Caiola

Matt Caiola

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Pool3-Car Garage4 FireplacesNew Construction

About This Home

A bold expression of sculptural architecture and modern organic design, this exceptional Green's Farms estate is set on 1.19 artfully layered acres with stacked stone walls, gardens, and a striking stone and white stucco facade. Walls of glass flood the interiors with natural light, seamlessly connecting the home to the private grounds and heated pool. Every space is composed with architectural precision, balancing dramatic scale with warmth and livability. The main level features a statement dining room anchored by a dramatic fireplace, sophisticated den showcasing architectural millwork and custom built-ins, private office, and an expansive living room which extends to a covered outdoor terrace with fireplace, creating a exquisite setting for effortless entertaining and relaxed outdoor living. The kitchen is defined by architectural wood cabinetry, striking natural stone, a curated suite of professional-grade appliances, and a fully appointed scullery. Upstairs, five ensuite bedrooms include a serene primary suite with fireplace, private terrace, dual walk-in closets, and a spa-inspired bath finished in natural stone and refined wood detailing. The finished lower level offers a gym, recreation/game room, media lounge, sixth bedroom, and full bath. Moments from beaches, train, shopping, and dining, this extraordinary residence offers exceptional craftsmanship and an effortless indoor-outdoor lifestyle in Westport's most coveted neighborhood.

Key Facts

City/Town
Westport
Neighborhood
Greens Farms
Property / Style
Single Family · Modern
Year Built
2026
Days on Market
18 days
Beds
6
Baths
6 full · 3 half
Living Area
8,623 sq ft
Lot Size
1.19 acres
Garage / Parking
3 garage
Property Taxes
$45,000 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

62

69 active listings

Median $ / Sq Ft

$763

69 active listings

Sale-to-List Ratio

100.0%

303 sales

How this home compares

List Price

$9.20M

vs $4.60M median

2.0× the median

Price / Sq Ft

$1,067

vs $763 median

39.8% above median

Days on Market

17 days

vs 62 days median

45 days fresher than median

Based on 69 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.

Location

38 Prospect Road, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$53,725

per month

  • Principal & Interest$46,908
  • Property Taxes$3,750
  • Insurance$3,067
  • 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
Modern
Year Built
2026
New Construction
Under Construction
Living Area
8,623 sq ft

Schools

Elementary
Greens Farms
High
Staples

Interior

Heating
Hydro AirZoned
Heat Fuel
Propane
Cooling
Central AirZoned
Fireplaces
4
Laundry
Upper Level
Laundry Location
2nd Floor
Appliances
Gas CooktopWall OvenMicrowaveRange HoodRefrigeratorFreezerDishwasherWine Chiller
Basement
FullHeatedFully FinishedCooledInterior AccessFull With Walk-Out
In-Law Apartment
PossibleDetachedLower Level
Additional Rooms
FoyerGymLaundry RoomMud Room

Exterior & Lot

Lot Size
1.19 acres
Zoning
AA
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Beach RightsWater Community
Water Source
Public Water Connected
Sewer
Septic
Pool
GuniteHeatedSpaIn Ground Pool
Construction
StoneStucco
Color
stone and white
Roof
Other
Foundation
Concrete
Exterior Features
GrillGuttersLightingPatio
Lot Description
Professionally Landscaped

Listing & Financials

Property Taxes
$45,000 / Annually
Days on Market
18
MLS #
24190177
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Jaclyn Picarillo

(203) 981-5012

Higgins Group Bedford Square

(203) 226-0300

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 5:45 AM UTC.