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38 Prospect Road

Westport, Connecticut 06880

ACTIVE$9,675,690
Beds
6
Baths
7 | 3
SqFt
8,623
Acres
1.19
Year Built
2026
Matt Caiola

Matt Caiola

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Guest HousePool3-Car Garage4 FireplacesNew Construction

About This Home

A bold expression of sculptural architecture and modern organic design, this one-of-a-kind Green's Farms estate with stone cottage is set on 1.19 artfully layered acres with stacked stone walls, gardens, and striking stone and white stucco facade. Walls of glass flood the interiors with natural light, seamlessly connecting the home to the private grounds with heated pool and spa. 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 living room and private office showcasing elevated millwork and custom built-ins, and an expansive family room which extends to a covered outdoor terrace with fireplace, creating an exquisite setting for effortless entertaining and relaxed outdoor living. The kitchen is defined by sleek 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, 2 private terraces, 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, 6th bedroom, and 1 1/2 baths. Moments from beaches, train, shopping, & 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
120 days
Beds
6
Baths
7 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

44

59 active listings

Median $ / Sq Ft

$783

59 active listings

Sale-to-List Ratio

100.0%

295 sales

How this home compares

List Price

$9.68M

vs $5.00M median

93.7% above median

Price / Sq Ft

$1,122

vs $783 median

43.3% above median

Days on Market

120 days

vs 44 days median

76 days longer than median

Based on 59 active and 295 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of November 6, 2026.

Location

38 Prospect Road, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$59,412

per month

  • Principal & Interest$52,437
  • Property Taxes$3,750
  • Insurance$3,225
  • 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
BalconyGrillGuttersLightingGuest HousePatio
Lot Description
Professionally Landscaped

Listing & Financials

Property Taxes
$45,000 / Annually
Days on Market
120
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 11/6/2026. 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 11/6/2026 at 3:01 AM UTC.