10 Side Hill Road
Westport, Connecticut 06880
- Beds
- 6
- Baths
- 4 | 2
- SqFt
- 6,844
- Acres
- 1.00
- Year Built
- 1997
- 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
Now more than ever, home is a haven - a place to live, work, relax, and entertain. Privately sited on 1 beautifully landscaped acre in highly sought-after Old Hill, this sophisticated 6,000+ SF home with a brand-new pool offers 6 bedrooms, exceptional living spaces, and breathtaking western sunsets overlooking Earthplace's 62-acre nature sanctuary. A rare blend of privacy, style, and convenience, all within walking distance to town. Designed for both elegant entertaining and comfortable everyday living, the main level features a stunning chef's kitchen with custom cabinetry, pantry, and sun-filled dining area flowing seamlessly into the spacious family room with fireplace - all overlooking the expansive lawns, sparkling pool, and serene natural setting. Formal living and dining rooms provide elegant gathering spaces, while a private office/playroom and guest bedroom with full bath complete the first floor. The luxurious primary serves as a private retreat with sitting area or office, walk-in closet, and spa-inspired bath. Four additional bedrooms, two full baths, and a conveniently located laundry room complete the second level. The top floor offers exceptional bonus space, including a vaulted-ceiling playroom, additional room, and half bath. The lower level provides versatile space featuring a gym, mudroom, and extensive storage. Chic yet welcoming interiors, contemporary amenities, and extraordinary natural surroundings combine to create the ultimate Westport retreat.
Key Facts
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
70
57 under contract
Median List Price
$4.70M
70 active listings
Median Closed Price
$2.42M
303 sales
Median Days on Market
56
70 active listings
Median $ / Sq Ft
$826
70 active listings
Sale-to-List Ratio
100.0%
303 sales
How this home compares
List Price
$3.25M
vs $4.70M median
30.8% below median
Price / Sq Ft
$475
vs $826 median
42.5% below median
Days on Market
61 days
vs 56 days median
5 days longer than median
Based on 70 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 28, 2026.
Location
10 Side Hill Road, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$16,571
- Property Taxes$2,181
- Insurance$1,083
- HOA$75
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
- 1997
- New Construction
- No/Resale
- Living Area
- 6,844 sq ft
- Below Grade
- 1,178 sq ft
Schools
- Elementary
- Kings Highway
- High
- Staples
Interior
- Heating
- Hot Air
- Heat Fuel
- PropaneOther
- Cooling
- Central AirZoned
- Fireplaces
- 2
- Laundry
- Upper Level
- Laundry Location
- Second Floor
- Appliances
- Oven/RangeRange HoodFreezerDishwasherWasherDryer
- Basement
- FullStorageGarage AccessInterior AccessPartially Finished
- Interior Features
- Audio SystemCable - Available
- Additional Rooms
- Bonus RoomFoyerLaundry RoomSitting Room
Exterior & Lot
- Lot Size
- 1.00 acres
- Zoning
- AA
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Beach RightsWater Community
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- HeatedSalt WaterIn Ground Pool
- Construction
- ClapboardWood
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- GuttersLightingStone WallFrench Doors
- Lot Description
- On Cul-De-Sac
HOA / Association
- Fee
- $900 / Annually
Listing & Financials
- Property Taxes
- $26,176 / Annually
- Days on Market
- 61
- MLS #
- 24178615
- MLS Status
- Under Contract
Similar Properties
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Co-Listed By
Justine Fink
The Riverside Realty Group
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 7:55 AM UTC.