31 Stonybrook Road
Westport, Connecticut 06880
- Beds
- 5
- Baths
- 6 | 2
- SqFt
- 6,503
- Acres
- 0.95
- Year Built
- 1936
- Neighborhood
- Old Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
From the moment you enter the gates of this Old Hill estate, you know you've arrived- a rare sanctuary built with a level of custom stonework and craftsmanship impossible to replicate today. This stunning 5 bedroom, 6.2 bath home offers an extraordinary blend of elegance, privacy, and nature. Set in a mature landscape that takes generations to establish, the setting delivers unmatched wildlife views-from herons and owls to ducks and otters along picturesque Stony Brook. Resort-style amenities feature a heated saltwater pool/spa, a private pond with a fountain, and deeded access to nearby Nash's Pond for kayaking and fishing. Inside, a dramatic wall of glass captures sweeping water views, creating a seamless connection to the outdoors. The main level includes a gourmet kitchen, family room with fireplace, dining room with wet bar, living room with fireplace and lounge, stone entry foyer, mudroom and two powder rooms. Upstairs, the primary suite boasts two terraces, dual walk-in closets, and a spa bath. Four additional bedrooms each with its own bathroom, a sprawling home office/6th bedroom with fireplace, a large playroom with a full bath, a third floor family room, and a mirrored gym/yoga studio with a ballet barre offer exceptional living options. Moments from Earthplace nature trails, key features include a heated 3-car garage, Crestron lighting, full-house generator, and a built-in poolside gas grill. A rare opportunity to own a sanctuary where design and nature converge.
Key Facts
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
$2.42M
307 sales
Median Days on Market
77
59 active listings
Median $ / Sq Ft
$823
59 active listings
Sale-to-List Ratio
100.0%
307 sales
How this home compares
List Price
$5.35M
vs $5.00M median
7.1% above median
Price / Sq Ft
$823
vs $823 median
In line with median
Days on Market
0 days
vs 77 days median
77 days fresher than median
Based on 59 active and 307 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of August 27, 2026.
Location
31 Stonybrook Road, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per month
- Principal & Interest$27,471
- Property Taxes$3,647
- Insurance$1,783
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1936
- New Construction
- No/Resale
- Living Area
- 6,503 sq ft
Schools
- Elementary
- Kings Highway
- High
- Staples
Interior
- Heating
- Hot Air
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Upper Level
- Appliances
- Gas CooktopWall OvenConvection OvenMicrowaveRange HoodRefrigeratorFreezerIcemakerDishwasherWasherDryerWine Chiller
- Basement
- Crawl SpaceConcrete Floor
- Interior Features
- Audio SystemOpen Floor PlanSecurity System
Exterior & Lot
- Lot Size
- 0.95 acres
- Zoning
- AA
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- PondBrook
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Pool
- GuniteHeatedSpaSalt WaterIn Ground Pool
- Construction
- StoneWood
- Roof
- Gable
- Foundation
- Concrete
- Exterior Features
- BalconyGrillLightingHot TubStone WallFrench DoorsUnderground SprinklerPatio
- Lot Description
- Fence - WoodFence - PrivacyFence - FullTreedLevel LotProfessionally LandscapedWater View
Listing & Financials
- Property Taxes
- $43,768 / Annually
- Days on Market
- 0
- MLS #
- 24201547
- 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 8/27/2026. 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 8/27/2026 at 3:35 PM UTC.