153 West Trail

Stamford, CT 06903

$1,325,000Active$9,938 Buyer Rebate*
4
beds
3.5
baths
4,001
SF

Our Take

153 West Trail is a Connecticut Colonial with four bedrooms and three finished levels. Oversized windows bring light into the eat-in kitchen, where an island connects to open French doors and a deck among the trees. The living room has a fireplace. The primary suite includes a dressing room, marble bath with soaking tub, and private balcony. Three additional bedrooms, including one ensuite, share the second floor with an optional office or nursery. The lower level adds a rec room and separate gym, while the grounds include an ipe deck, bluestone patio, outdoor kitchen, hot tub, and pergola-covered gathering spot.

Property Details

Listing Facts

Acres
1.17
Year built
1964
Taxes (July 2025-June 2026)
$14,532 (July 2025-June 2026)
Price/SF
$331
Days on Market
8 Days
MLS number
24198396

Highlights

  • Eat-in kitchen with island and deck access
  • Living room fireplace
  • Primary suite with dressing room and marble bath
  • Private balcony overlooking the backyard
  • Three additional bedrooms, including one ensuite
  • Rec room and separate gym
  • Ipe deck, bluestone patio, outdoor kitchen, and hot tub
  • Pergola-covered outdoor gathering spot
Read the full listing description

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.

Schools

Elementary
Per Board of Ed
Middle
Not provided
High
Per Board of Ed

School assignments as reported by SmartMLS.

Price History

DateEventPrice
Listed$1,325,000

Listing Agent

Compass Connecticut, LLC · (203) 442-6626
John Dunn · (203) 388-5353

Building permit history

How we compile this →

Municipal records document permitted work at this property.

2026
Building PermitMechanical

Legalize work done in the basement. 900 SF. Walled off existing space. Left all mechanical (heating and air conditioning) in place.

Issued date
PermitB-26-1212
Permit typeBuilding Permit
Declared project cost$40,000

Interpretation note: This matched record set reflects only the municipal data currently imported; it is not a claim that no other work occurred.

How we compile this. The source is Stamford municipal permit records. These records are imported periodically and are not a live feed from the town. A permit’s presence does not, by itself, confirm that work was completed or passed final inspection. Dates shown are issue dates unless identified otherwise. Descriptions may be lightly edited for readability without changing material details. Dollar amounts are town-reported project costs or permit valuations, not estimates of the property’s market value.

Map

153 West Trail, Stamford, CT 06903

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SmartMLS · Listing #24198396 · Active

Listing data checked: Oct 28, 2026, 6:39 AM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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153 West Trail · Stamford, CT

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