104 Old Road
Westport, Connecticut 06880
- Beds
- 4
- Baths
- 3
- SqFt
- 2,807
- Acres
- 0.51
- Year Built
- 1954
- 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
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
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
53
32 under contract
Median List Price
$5.00M
53 active listings
Median Closed Price
$2.42M
312 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 3, 2026per 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
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
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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 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.