147 Highline Trail
Stamford, Connecticut 06902
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,505
- Acres
- 2.00
- Year Built
- 1921
- Neighborhood
- Westover
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Rare. Exceptional. Timeless. Hidden away on a private two-acre cul-de-sac where Westover meets Greenwich, this Mid-Century Modern estate is a masterclass in light, height, and form. Designed for an inspired lifestyle, the main residence boasts five spacious bedrooms and four-and-a-half baths, defined by sweeping architectural lines and massive expanses of glass that look out over the Mianus River. A true compound for creatives and entertainers alike, the property features a spectacular detached pool house complete with a kitchen, lofted bedroom, and full bath-perfect for multigenerational living or an ultra-private guest suite. A vintage greenhouse, detached two-car garage, and a storied history of artistic residents complete this unparalleled sanctuary. Live where nature and iconic design completely converge.
Key Facts
Market Snapshot
The Stamford Market
Single Family · trailing 12 months
Active Listings
77
116 under contract
Median List Price
$1.20M
77 active listings
Median Closed Price
$977,000
577 sales
Median Days on Market
39
77 active listings
Median $ / Sq Ft
$414
77 active listings
Sale-to-List Ratio
103.8%
577 sales
How this home compares
List Price
$1.59M
vs $1.20M median
33.5% above median
Price / Sq Ft
$354
vs $414 median
14.5% below median
Days on Market
33 days
vs 39 days median
6 days fresher than median
Based on 77 active and 577 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of July 28, 2026.
Location
147 Highline Trail, Stamford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$8,132
- Property Taxes$1,766
- Insurance$532
- 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
- Contemporary
- Year Built
- 1921
- New Construction
- No/Resale
- Living Area
- 4,505 sq ft
Schools
- Elementary
- Stillmeadow
- High
- Westhill
Interior
- Heating
- Steam
- Heat Fuel
- Oil
- Cooling
- Central AirWall Unit
- Fireplaces
- 2
- Appliances
- Gas CooktopOven/RangeRefrigeratorFreezerDishwasherWasherDryer
- Basement
- PartialUnfinished
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- RA1
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- View
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- Pool HouseSpaIn Ground Pool
- Construction
- StoneWood
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- TreedProfessionally LandscapedRollingWater View
Listing & Financials
- Property Taxes
- $21,195 / Annually
- Days on Market
- 33
- MLS #
- 24186866
- MLS Status
- Under Contract
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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 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.