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52 Chesterfield Road

Stamford, Connecticut 06902

PENDING$2,500,000
Beds
4
Baths
3 | 1
SqFt
4,164
Acres
0.14
Year Built
1920
Matt Caiola

Matt Caiola

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About This Home

HIGHEST AND BEST BY JULY 14 AT 5:00. Rarely available in the highly sought-after ALC neighborhood of Shippan Point, this beautifully maintained 4-bedroom, 3.5 bath home offers exceptional quality, thoughtful design and a prime location. The home has deeded beach rights to a private beach on LI Sound, which is located just steps away. Completely reimagined through an extensive renovation and expansion, the home was redesigned to enhance function and flow. High ceilings, abundant natural light, and well-proportioned living spaces create a welcoming atmosphere throughout. The renovation included the addition of a 3rd floor, reconfiguration of the 1st and 2nd floors, 3 new bathrooms and a 2nd floor laundry room. Additional living spaces include a family room, a finished lower level and a 3rd floor home office with water views that can also serve as a 5th bedroom. At the center of the home is a custom kitchen by Deane, featuring Wolf, Thermador and Sub-Zero appliances, custom cabinetry and generous workspace. Throughout the home custom millwork, high-end finishes, and professionally curated interiors reflect careful attention to detail and timeless style. The primary suite offers a peaceful retreat with a private deck with water views. Set on a professionally landscaped corner lot, the property offers strong curb appeal and an ideal location within one of Stamford's most desirable waterfront neighborhoods. This beautiful home is ready for its next owners.

Key Facts

City/Town
Stamford
Neighborhood
Shippan
Property / Style
Single Family · Colonial
Year Built
1920
Days on Market
23 days
Beds
4
Baths
3 full · 1 half
Living Area
4,164 sq ft
Lot Size
0.14 acres
Garage / Parking
1 garage
Property Taxes
$21,689 / Annually
HOA Fee
$325 / Annually

Market Snapshot

The Stamford Market

Single Family · trailing 12 months

View area

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

$2.50M

vs $1.20M median

2.1× the median

Price / Sq Ft

$600

vs $414 median

44.9% above median

Days on Market

23 days

vs 39 days median

16 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

52 Chesterfield Road, Stamford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$15,414

per month

  • Principal & Interest$12,747
  • Property Taxes$1,807
  • Insurance$833
  • HOA$27

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

Location

City/Town
Stamford
Neighborhood
Shippan
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1920
New Construction
No/Resale
Living Area
4,164 sq ft

Schools

Elementary
Toquam Magnet
High
Stamford

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Laundry
Upper Level
Laundry Location
On second floor
Appliances
Gas CooktopWall OvenMicrowaveRange HoodSubzeroDishwasherDisposalWasherDryerWine Chiller
Basement
FullPartially Finished

Exterior & Lot

Lot Size
0.14 acres
Zoning
R75
Garage / Parking
1 garage spaceAttached Garage
Waterfront Details
Walk to WaterBeach RightsWater CommunityView
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Shake
Roof
Asphalt Shingle
Foundation
Stone
Lot Description
Level LotWater View

HOA / Association

Fee
$325 / Annually

Listing & Financials

Property Taxes
$21,689 / Annually
Days on Market
23
MLS #
24187400
MLS Status
Under Contract

Similar Properties

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

Listed By

Barbara Ryan

(203) 326-1144

William Raveis Real Estate

(203) 322-0200

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 6:55 AM UTC.