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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.
Shippan Point, located between Stamford Harbor and Long Island Sound, is a waterfront and residential Stamford neighborhood with a peninsula setting and sweeping marina views. The neighborhood’s character concentrates around Shippan Avenue near the Stamford Yacht Club, where sail masts, dock gates, and a quiet coastal rhythm set the tone. Architectural identity leans to shingle-style and mid-century homes alongside newer coastal builds, many oriented toward the water. Cummings Park frames the shoreline with open lawns and a long edge for walking. The Stamford Yacht Club and Brennan’s by the Beach act as local pillars for on-the-water gatherings. Streets curve toward small coves, giving daily life a distinctly maritime cadence.
Provided by Walk Score and Local Logic
Market insights
37 Chesterfield Rd · $1,995,000
DAYS ON MARKET
1 days
The average home goes pending in 50 days.
SALE-TO-LIST
101.6%
Most homes are selling 2% above list price.
LIST PRICE
$1,995,000
Median sale price in this area is $797,397. (60% lower than this home)
PRICE DROP
0 price drops
18% of homes in this area have had a price drop in the past month.
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Interior features
Open floor plan
Audio system
Cable pre-wiring
Auto garage door opener
Home automation for lighting and thermostats
Wired for audio
Fireplace
Full, finished basement
Attic with pull-down stairs
Bedrooms
4 bedrooms
Bathrooms
3 full bathrooms
1 half bathroom
Kitchen
Gas range
Refrigerator
Freezer
Dishwasher
Laundry & utility
Washer and dryer
Upstairs laundry closet
Tankless natural gas hot water
Heating & cooling
Hydro-air heating with natural gas
Central air
Exterior features
Terrace
Deck
Shed
Gutters
Exterior lighting
Underground sprinklers
Level lot
In-ground vinyl pool
Walk to water
Beach rights
Home design
Single-family home
Parking
Attached garage
Private driveway
4 total parking spaces
Security
Security system
Construction
Frame construction
Hardie board siding
Asphalt shingle roof
Concrete and masonry foundation
Utilities
Public water
Public sewer
Generator ready
Electricity and solar
View estimated energy costs and solar savings for 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.
Smart MLS #24220404
Nov 12, 2026
Listed
$1,995,000
$586/sq ft
Public Records
Dec 3, 2018
Sold
$480,000
$141/sq ft
Public Records
Sep 17, 2004
Sold
$928,500
$273/sq ft
GMLS #56622
May 24, 2004
Listed
$988,000
$290/sq ft
Smart MLS #98197650
May 13, 2004
Listed
$988,000
$290/sq ft
Year
Property tax
Land + Additions
Assessment*
2022
$15,157 (+0.9%)
$335,400 + $222,460
$557,860
2021
$15,029 (+2.2%)
$335,400 + $222,460
$557,860
2020
$14,700
$335,400 + $222,460
$557,860
2019
$14,700 (+3.2%)
$335,400 + $222,460
$557,860
2018
$14,242 (+2.7%)
$335,400 + $222,460
$557,860
2017
$13,864 (+2.9%)
$294,440 + $221,140
$515,580
2016
$13,467 (+5.4%)
$294,440 + $221,140
$515,580
2014
$12,781
$294,440 + $221,140
$515,580
Public record
Beds
5
Baths
3
Stories
2
Lot width
—
Lot depth
—
Lot size
0.29 Acres
Year renovated
—
Finished Sq. Ft.
2,606
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,606
Year built
1928
Style
Single Family Residential
County
Fairfield County
APN
325084
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 12, 2023.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
6/10 Heat Factor
7 days above 98° expected this year, 16 days in 30 years
7/10 Wind Factor
78% chance of strong winds in next 30 years
5/10 Air Factor
7 unhealthy days expected this year, 9 days in 30 years
Provided by First Street
Historical weather
Stamford, CT • 06902
Average low and high temperatures (°F)
36°
23°
38°
24°
52°
34°
62°
44°
69°
52°
81°
62°
85°
69°
80°
62°
76°
59°
64°
49°
55°
39°
40°
27°
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
87/ 100
Very good sunlight
Sunscore
This home ranks in the top 29% for direct sun exposure in Stamford. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
8.9 hrs
4.7 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 37 Chesterfield Rd
$1,985,473
$9,527 under list price of $2.00M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $650K to $2.8M.