38 Prospect Road
Westport, Connecticut 06880
- Beds
- 6
- Baths
- 7 | 3
- SqFt
- 8,623
- Acres
- 1.19
- Year Built
- 2026
- Neighborhood
- Greens Farms
- Property Type
- Single Family

Matt Caiola
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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
Active Listings
59
41 under contract
Median List Price
$5.00M
59 active listings
Median Closed Price
$2.40M
295 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per 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
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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.