114 Cross Highway
Westport, Connecticut 06880
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,179
- Acres
- 1.26
- Year Built
- 1964
- Neighborhood
- Long Lots
- 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
Welcome to a one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian Estate. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for everyday living or entertaining. The formal DR offers its own fireplace, blending classic character with warmth and style. The chef's kitchen features two iconic AGA stoves, a walk-in pantry, skylights and a large center island. A charming covered porch offers peaceful morning coffee or evening outdoor dining. Upstairs, the primary suite, is a private sanctuary with vaulted ceilings, sunny sitting room, HW floors, walk-in closet, and spa-like bath incl cast iron soaking tub, oversized shower and elegant finishes. Add'l bedrooms 1 en suite the other w hall bath on the 2nd floor and 2 more Bedrooms on the 3rd floor w Hall Bath are bright and spacious, each w/ HW floors and serene views of the pool and gardens. The LL offers gym area, work space, storage and access to 2 car garage. The fully fenced backyard is a private paradise. Stone walls, mature English gardens and spectacular In-ground pool with auto cover add to the magic of this private oasis. Whole House Generator. Minutes to schools, shopping and town offering the rare combination of luxury, charm, privacy and convenience.
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
$2.70M
vs $4.60M median
41.3% below median
Price / Sq Ft
$646
vs $820 median
21.2% below median
Days on Market
110 days
vs 56 days median
54 days longer than 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
114 Cross Highway, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$13,767
- Property Taxes$1,801
- Insurance$900
- 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
- 1964
- New Construction
- No/Resale
- Living Area
- 4,179 sq ft
Schools
- Elementary
- Long Lots
- High
- Staples
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Oven/RangeRange HoodRefrigeratorFreezerDishwasher
- Basement
- Full
Exterior & Lot
- Lot Size
- 1.26 acres
- Zoning
- AA
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- Pond
- Water Source
- Public Water Connected
- Sewer
- Septic
- Pool
- In Ground Pool
- Construction
- Hardie Board
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Fence - FullSome WetlandsLevel LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $21,612 / Annually
- Days on Market
- 110
- MLS #
- 24165047
- MLS Status
- Under Contract
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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 10:05 AM UTC.