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104 Old Road

Westport, Connecticut 06880

COMING SOON - NEW$1,649,000
Beds
4
Baths
3
SqFt
2,807
Acres
0.51
Year Built
1954
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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1-Car Garage1 FireplaceVirtual Tour

About This Home

Set on a private flat half acre and thoughtfully expanded and beautifully maintained, this move-in-ready 4 bedroom home offers a flexible floor plan designed for today's lifestyle, with exceptional space for work, entertaining, and relaxation. Enter to a wonderful sun filled living room with fireplace, a new renovated kitchen with large island and stainless steel appliances and separate dining area. Adjacent to the kitchen is a sun filled great room with vaulted ceilings that opens to a generous stone patio-perfect for endless entertaining inside and out. Finished across four levels, the home offers a wonderful blend of comfort and privacy. The spacious primary suite occupies its own private floor and features vaulted ceilings, a walk-in closet, and a luxurious bath. An adjacent oversized room provides the perfect retreat for a home office, gym, or additional living space. 3 additional bedrooms share another large bath. The finished lower level offers even more versatility, with a separate entrance, mudroom/laundry room, full bath, and a flexible playroom, family room, or second home office. Outside, the level, fully fenced yard provides plenty of room for play, pets, gardening, and entertaining. With its exceptional location, thoughtfully designed spaces, and inviting indoor-outdoor living, 104 Old Road is a wonderful opportunity to enjoy all that Westport has to offer-close to town, schools, shopping, & just minutes from the Greens Farms train station.

Key Facts

City/Town
Westport
Neighborhood
Long Lots
Property / Style
Single Family · Split Level
Year Built
1954
Days on Market
1 day
Beds
4
Baths
3 full
Living Area
2,807 sq ft
Lot Size
0.51 acres
Garage / Parking
1 garage
Property Taxes
$10,035 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

57

53 active listings

Median $ / Sq Ft

$821

53 active listings

Sale-to-List Ratio

100.0%

312 sales

How this home compares

List Price

$1.65M

vs $5.00M median

67.0% below median

Price / Sq Ft

$587

vs $821 median

28.5% below median

Days on Market

1 day

vs 57 days median

56 days fresher than median

Based on 53 active and 312 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of September 6, 2026.

Location

104 Old Road, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$9,907

per month

  • Principal & Interest$8,521
  • Property Taxes$836
  • Insurance$550
  • 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
Split Level
Year Built
1954
New Construction
No/Resale
Living Area
2,807 sq ft

Schools

Elementary
Long Lots
High
Staples

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Appliances
Electric CooktopOven/RangeMicrowaveRefrigeratorFreezerDishwasherWasherDryer
Basement
Crawl Space
Interior Features
Auto Garage Door OpenerOpen Floor Plan

Exterior & Lot

Lot Size
0.51 acres
Zoning
A
Garage / Parking
1 garage spaceAttached Garage
Waterfront Details
Beach Rights
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
No
Construction
Clapboard
Color
Grey
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Garden AreaStone WallPatio
Lot Description
Level Lot

Listing & Financials

Property Taxes
$10,035 / Annually
Days on Market
1
MLS #
24201214
MLS Status
Coming Soon

Similar Properties

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

Listed By

Casey Lange

(203) 249-0900

Compass Connecticut, LLC

(203) 423-3100

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/6/2026. 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 9/6/2026 at 8:05 AM UTC.