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.
Flood risk: check the FEMA flood map for this address.
Schools
Taxes
Interior
Building & Exterior
Lot & Land
What it would cost per month
An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.
What's nearby
Real streets from OpenStreetMap; distances are straight-line from the property, not driving routes.
Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.
Recent comparable sales
The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.
5 comparable sales — median $1,875,000, ranging $1,582,500 to $2,029,422.
- $1,582,500$607/sq ft2026-09-16
- $1,750,000$818/sq ft2026-08-17
- $1,875,000$577/sq ft2026-06-08
- $2,025,000$702/sq ft2026-05-15
- $2,029,422$795/sq ft2025-06-30
Public record
From the Westport assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.
Recorded sales
Deed transfers on file with the Westport land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.
- 2022-12-20$1,250,000Single Family
- 2002-11-15$688,000
More homes in Westport
Closest in price to this one.