153 West Trail, Stamford, Connecticut 06903

About this home

There's a particular quiet that settles over 153 West Trail Road - the kind that comes from thirty years of a family calling this 4,000-square-foot classic Connecticut Colonial home, and grounds so thoughtfully planted the outside world falls away as you turn up the drive. Inside, the house unfolds unhurried across three finished levels. Sunlight pours through oversized windows and pools across the eat-in kitchen's island, where morning coffee turns naturally into open French doors and a deck that seems to float in the trees. By evening, the living room fireplace pulls everyone back inside. Upstairs, the primary suite feels less like a bedroom and more like an escape - a dressing room, a marble bath with soaking tub, and a private balcony overlooking the gorgeous backyard. Three more bedrooms (one ensuite), and an optional office/nursery complete the second floor. Downstairs, a spacious rec room and a separate gym give the lower level a life of its own, while outside, the wooded, private grounds unfold into an 800-square-foot Ipe wood deck, a bluestone patio with outdoor kitchen, and a separate pergola-covered gathering spot. Cared for year after year because it was loved - this rare, turnkey home is ready for its next lucky owner.

Flood risk: check the FEMA flood map for this address.

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

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 $1,200,000, ranging $1,130,000 to $1,470,000.

Within a 15-minute walk, sold in the last year
• 49 Alexandra Drive3 bd · 4 ba · 3,436 sq ft · 0.2 mi away
  $1,130,000$328/sq ft2025-12-19
• 58 Briar Woods Trail3 bd · 5 ba · 4,388 sq ft · 0.2 mi away
  $1,149,000$261/sq ft2026-09-16
• 95 Alexandra Drive5 bd · 5 ba · 4,312 sq ft · 0.3 mi away
  $1,200,000$278/sq ft2026-07-30
• 95 Saddle Hill Road5 bd · 4 ba · 3,892 sq ft · 0.6 mi away
  $1,450,000$372/sq ft2026-06-12
• 250 Saddle Hill Road4 bd · 5 ba · 3,885 sq ft · 0.7 mi away
  $1,470,000$378/sq ft2025-11-10

Public record

From the Stamford 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.

More homes in Stamford

Closest in price to this one.

• 30 Ridge Brook Lane4 bed · 3 bath · 3,297 sq ft$1,325,000
• 11 Joan Road4 bed · 3 bath · 3,406 sq ft$1,340,000
• 128 Van Buskirk Avenue5 bed · 4 bath · 2,930 sq ft$1,300,000
• 68 Parry Road3 bed · 3 bath · 2,790 sq ft$1,350,000
• 72 Doral Farm Road3 bed · 3 bath · 3,132 sq ft$1,350,000
• 34 Downs Avenue5 bed · 4 bath · 3,094 sq ft$1,295,000

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