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
Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple serene water features-a heated saltwater gunite pool with hot tub, a tranquil private pond with fountain and picturesque Stony Brook. The stately stone and wood exterior blends seamlessly with the lush surroundings, while inside, an expansive, light-filled layout is ideal both for grand entertaining and quiet retreat. A dramatic wall of windows captures sweeping views of the brook, creating a seamless connection between indoor comfort and the surrounding landscape. The ground floor consists of a gourmet kitchen, large family room with fireplace, dining room with wet bar, living room with fireplace + lounge area with water views, a large entry foyer with stone floors and two powder rooms. Upstairs, a primary bedroom suite with two balconies overlooking the pond and brook, two walk in closets & beautifully appointed bathroom, 4 additional bedrooms each with its own bathroom, a large home office/6th bedroom with fireplace and brook & pond views, a large playroom with full bathroom, windowed home gym, and another family room on the 3rd floor, offering multiple options for relaxation and entertainment. Fully fenced for privacy with automated driveway gates, it has a heated 3 car garage, Crestron lighting system, full house generator, mature landscaping, and a gas grill seamlessly built into the stonework by the pool.
Key Facts
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
71
56 under contract
Median List Price
$4.60M
71 active listings
Median Closed Price
$2.42M
303 sales
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
$5.75M
vs $4.60M median
25.0% above median
Price / Sq Ft
$884
vs $820 median
7.8% above median
Days on Market
56 days
vs 56 days median
In line with 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
31 Stonybrook Road, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$29,318
- Property Taxes$3,647
- Insurance$1,917
- 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
- 56
- MLS #
- 24178699
- 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 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 10:01 AM UTC.