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110 Cross Highway

Westport, Connecticut 06880

ACTIVE$1,999,000
Beds
5
Baths
3 | 1
SqFt
2,864
Acres
1.57
Year Built
1956
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage2 Fireplaces

About This Home

Experience modern luxury in this beautifully reimagined home, set on 1.57 scenic, park-like acres. Thoughtfully renovated, this 2,864 sq ft residence offers open-concept living spaces filled with natural light and sophisticated finishes throughout. The designer kitchen features a stunning island and premium cabinetry, flowing seamlessly into the dining and living areas with a dramatic linear fireplace. The spacious family room opens to a sun-soaked bluestone patio overlooking an expansive backyard extending to the pond-an idyllic setting for entertaining and everyday enjoyment. The fabulous primary suite is a private retreat with a cozy fireplace, incredible walk-in closet, and beautifully appointed modern bath. Two additional bedrooms complete the second level, while a private 4th-bedroom ensuite is ideal for guests or flexible living space. A main-level office/5th bedroom, powder room, and mudroom with custom built-ins leading to the 2-car garage add versatility and convenience. Ideally located within walking distance of Staples High School and Bedford Middle School, and minutes from Westport's beaches, vibrant downtown, shopping, dining, and train station.

Key Facts

City/Town
Westport
Neighborhood
Long Lots
Property / Style
Single Family · Colonial
Year Built
1956
Days on Market
12 days
Beds
5
Baths
3 full · 1 half
Living Area
2,864 sq ft
Lot Size
1.57 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$11,254 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

60

70 active listings

Median $ / Sq Ft

$821

70 active listings

Sale-to-List Ratio

100.0%

303 sales

How this home compares

List Price

$2.00M

vs $4.70M median

57.4% below median

Price / Sq Ft

$698

vs $821 median

15.0% below median

Days on Market

12 days

vs 60 days median

48 days fresher than median

Based on 70 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.

Location

110 Cross Highway, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,796

per month

  • Principal & Interest$10,192
  • Property Taxes$938
  • Insurance$666
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Westport
Neighborhood
Long Lots
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1956
New Construction
No/Resale
Living Area
2,864 sq ft

Schools

Elementary
Long Lots
High
Staples

Interior

Heating
Hot AirHot Water
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
2
Appliances
Gas RangeWall OvenMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
Basement
Crawl SpaceUnfinished
In-Law Apartment
PossibleOver Garage
Interior Features
Auto Garage Door Opener

Exterior & Lot

Lot Size
1.57 acres
Zoning
AA
Garage / Parking
2 garage spaces6 total parking spacesAttached GaragePavedDrivewayPrivate
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
Hardie Board
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
GuttersUnderground SprinklerPatio
Lot Description
Fence - Partial

Listing & Financials

Property Taxes
$11,254 / Annually
Days on Market
12
MLS #
24191704
MLS Status
Active

Similar Properties

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

Listed By

Stephanie Ferreira

(203) 520-2305

BHGRE Gaetano Marra Homes

(203) 627-8726

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 2:05 PM UTC.