52 Chesterfield Road
Stamford, Connecticut 06902
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 4,164
- Acres
- 0.14
- Year Built
- 1920
- Neighborhood
- Shippan
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
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
$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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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.
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.