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153 West Trail

Stamford, Connecticut 06903

COMING SOON - NEW$1,325,000
Beds
4
Baths
3 | 1
SqFt
4,001
Acres
1.17
Year Built
1964
Matt Caiola

Matt Caiola

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1 Fireplace

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 hot tub, 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.

Key Facts

City/Town
Stamford
Neighborhood
North Stamford
Property / Style
Single Family · Colonial
Year Built
1964
Days on Market
0 days
Beds
4
Baths
3 full · 1 half
Living Area
4,001 sq ft
Lot Size
1.17 acres
Property Taxes
$14,532 / Annually

Market Snapshot

The Stamford Market

Single Family · trailing 12 months

View area

Median Days on Market

39

84 active listings

Median $ / Sq Ft

$419

84 active listings

Sale-to-List Ratio

104.1%

575 sales

How this home compares

List Price

$1.32M

vs $1.13M median

17.4% above median

Price / Sq Ft

$331

vs $419 median

21.0% below median

Days on Market

0 days

vs 39 days median

39 days fresher than median

Based on 84 active and 575 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of October 16, 2026.

Location

153 West Trail, Stamford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,992

per month

  • Principal & Interest$7,339
  • Property Taxes$1,211
  • Insurance$442
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Stamford
Neighborhood
North Stamford
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1964
New Construction
No/Resale
Living Area
4,001 sq ft
Below Grade
960 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Ceiling FansCentral Air
Fireplaces
1
Appliances
Cook TopOven/RangeRefrigeratorDishwasherWasherDryer
Basement
FullFully Finished
Additional Rooms
Exercise RoomFoyerMud Room

Exterior & Lot

Lot Size
1.17 acres
Zoning
RA1
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
ClapboardWood
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Fence - PrivacyProfessionally Landscaped

Listing & Financials

Property Taxes
$14,532 / Annually
Days on Market
0
MLS #
24198396
MLS Status
Coming Soon

Similar Properties

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Listed By

John Dunn

(203) 388-5353

Compass Connecticut, LLC

(203) 442-6626

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/16/2026. 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 10/16/2026 at 11:05 PM UTC.