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592 West Hill Road

Stamford, Connecticut 06902

COMING SOON - NEW$1,299,000
Beds
5
Baths
3 | 1
SqFt
3,788
Acres
1.49
Year Built
1927
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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1 Fireplace

About This Home

Move right into this timeless classic Colonial, beautifully sited on 1.49 manicured acres with a fully fenced backyard in the heart of desirable Westover. Brimming with character and thoughtfully updated throughout, the home welcomes you with a stunning foyer that opens to an expansive living room with a wood burning fireplace and a bright, elegant formal dining room. The chef's kitchen offers generous space for cooking and entertaining and flows into an expansive pantry and mudroom for exceptional everyday functionality. The grounds are perfect for entertaining, a large front patio, and back deck for BBQ's. Plenty of room for a pool and site plans available for a 3 car garage. Freshly painted throughout, the home also features beautifully refinished hardwood floors across the first and second levels. Upstairs, the completely renovated primary suite features a spacious walk-in closet and luxurious marble bath with Waterworks fixtures. The third floor, converted in 2024 adds an additional bedroom, full bath, and bonus office space, ideal for guests, working from home, or flexible living. Extensive improvements include a new 5 bedroom septic system (2021); Full HVAC and Electrical upgrades (2022); EV charger (2023); and third floor renovation (2024). With classic architecture, beautifully refreshed interiors, and extensive modern upgrades, this exceptional Westover home presents a rare opportunity in one of Stamford's most desirable neighborhoods.

Key Facts

City/Town
Stamford
Neighborhood
Westover
Property / Style
Single Family · Colonial
Year Built
1927
Days on Market
0 days
Beds
5
Baths
3 full · 1 half
Living Area
3,788 sq ft
Lot Size
1.49 acres
Property Taxes
$15,591 / Annually

Market Snapshot

The Stamford Market

Single Family · trailing 12 months

View area

Median Days on Market

32

92 active listings

Median $ / Sq Ft

$417

92 active listings

Sale-to-List Ratio

104.0%

568 sales

How this home compares

List Price

$1.30M

vs $1.15M median

13.0% above median

Price / Sq Ft

$343

vs $417 median

17.7% below median

Days on Market

0 days

vs 32 days median

32 days fresher than median

Based on 92 active and 568 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of September 14, 2026.

Location

592 West Hill Road, Stamford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,479

per month

  • Principal & Interest$6,747
  • Property Taxes$1,299
  • Insurance$433
  • HOA$0

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

Location

City/Town
Stamford
Neighborhood
Westover
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1927
New Construction
No/Resale
Living Area
3,788 sq ft

Schools

Elementary
Roxbury
High
Westhill

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Appliances
Gas CooktopWall OvenMicrowaveRefrigeratorFreezerWasherDryer
Basement
FullUnfinishedFull With Walk-Out

Exterior & Lot

Lot Size
1.49 acres
Zoning
RA1
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
CedarStone
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Level LotProfessionally Landscaped

Listing & Financials

Property Taxes
$15,591 / Annually
Days on Market
0
MLS #
24196481
MLS Status
Coming Soon

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Molly Rubins

(203) 216-3111

NestSeekers International

(203) 204-9555

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

The IDX display contains information sourced from SmartMLS, Inc. as of 9/14/2026. 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 9/14/2026 at 10:55 PM UTC.