37 Chesterfield Road
Stamford, Connecticut 06902
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,405
- Acres
- 0.29
- Year Built
- 1928
- Neighborhood
- Shippan
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
With deeded beach rights in Shippan Point's private ALC Beach Association, this sun-drenched coastal home blends timeless character with a stunning studs-out transformation. An expansive double lot offers landscaped grounds, updated pool and spacious motor court. New stone walls and steps lead to a custom arched mahogany entry. The 4 BR, 3.5 BA home features an open great room with oak floors, wood-burning fireplace and Thermador kitchen. A den and versatile living space overlook the pool and grounds. Upstairs, 4 BRs include a primary suite with private deck and spa bath, plus 2nd-floor laundry. The finished lower level adds 800 sq ft with full bath and kitchenette. Refined finishes, all-new infrastructure, Lutron lighting, built-in speakers, networking and Ring cameras complete the home.
Key Facts
Market Snapshot
The Stamford Market
Single Family · trailing 12 months
Active Listings
93
96 under contract
Median List Price
$1.25M
93 active listings
Median Closed Price
$975,000
574 sales
Median Days on Market
35
93 active listings
Median $ / Sq Ft
$417
93 active listings
Sale-to-List Ratio
104.1%
574 sales
How this home compares
List Price
$2.00M
vs $1.25M median
59.7% above median
Price / Sq Ft
$586
vs $417 median
40.5% above median
Days on Market
0 days
vs 35 days median
35 days fresher than median
Based on 93 active and 574 closed sales (trailing 12 mo) of single family in Stamford. Source: SmartMLS · As of November 12, 2026.
Location
37 Chesterfield Road, Stamford, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$10,812
- Property Taxes$1,391
- Insurance$665
- 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
- Colonial
- Year Built
- 1928
- New Construction
- No/Resale
- Living Area
- 3,405 sq ft
- Below Grade
- 799 sq ft
Schools
- Elementary
- Toquam Magnet
- High
- Stamford
Interior
- Heating
- Hydro Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Upper Level
- Laundry Location
- Upstairs closet
- Appliances
- Gas RangeRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullFully Finished
- Interior Features
- Audio SystemAuto Garage Door OpenerCable - Pre-wiredOpen Floor PlanSecurity System
Exterior & Lot
- Lot Size
- 0.29 acres
- Zoning
- R75
- Garage / Parking
- 1 garage space4 total parking spacesAttached GarageDrivewayPrivate
- Waterfront Details
- Walk to WaterBeach Rights
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Pool
- VinylIn Ground Pool
- Construction
- Hardie Board
- Roof
- Asphalt Shingle
- Foundation
- ConcreteMasonry
- Exterior Features
- TerraceShedDeckGuttersLightingUnderground Sprinkler
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $16,691 / Annually
- Days on Market
- 0
- MLS #
- 24220404
- MLS Status
- Active
Similar Properties
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Co-Listed By
Spencer Sodokoff
Houlihan Lawrence
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/12/2026. 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 11/12/2026 at 11:45 PM UTC.