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10 Side Hill Road

Westport, Connecticut 06880

PENDING$3,250,000
Beds
6
Baths
4 | 2
SqFt
6,844
Acres
1.00
Year Built
1997
Matt Caiola

Matt Caiola

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Pool3-Car Garage2 Fireplaces

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

City/Town
Westport
Neighborhood
Old Hill
Property / Style
Single Family · Colonial
Year Built
1997
Days on Market
61 days
Beds
6
Baths
4 full · 2 half
Living Area
6,844 sq ft
Lot Size
1.00 acres
Garage / Parking
3 garage
Property Taxes
$26,176 / Annually
HOA Fee
$900 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$19,910

per 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

City/Town
Westport
Neighborhood
Old Hill
County
Fairfield

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

Homes with a close match in area, property type, and price.

Listed By

Susan Lieberman

(203) 858-9411

The Riverside Realty Group

(203) 226-8300

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.