Tucked away on two serene, park-like acres in North Stamford, 28 Pony Trail offers a refined blend of modern design and effortless living just minutes from the Greenwich border and Merritt Parkway. Natural light fills the home, enhanced by soaring vaulted ceilings and skylights that create an elevated yet inviting atmosphere with seamless indoor-outdoor flow. The property is set against a tranquil natural backdrop, complete with a gentle brook. A custom chef's kitchen by Deane anchors the home, featuring a large walnut center island, marble countertops, and a custom walk-in pantry, while living spaces extend to a large composite deck with multiple access points-ideal for entertaining or enjoying the peaceful surroundings. The Home offers two luxurious primary suites with spa-like baths, including a main-level suite with dressing area and walk-in closet. Upstairs, a second primary suite features dual walk-in closets, along with two additional bedrooms, an updated hall bath, large closets and custom built-ins. A spacious main-level office/den adds flexibility. Additional highlights include two laundry location options, a large unfinished lower level complete with gym, extensive storage, wine capacity for 500+ bottles and potential for a playroom. Enjoy close proximity to Greenwich horse trails and Greenwich Avenue, along with Metro-North access to NYC and Stamford amenities. Added features for convenience include a whole-house generator and irrigation system
***Please submit Final and Best offers by Tuesday 5/5 at noon***
Est. $3,744 per month, based on comparable rentals
Sale and tax history for 28 Pony Trail Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24170555
Jun 23, 2026
Sold
$1,400,000
$469/sq ft
May 14, 2026
Pending
—
May 1, 2026
Listed
$1,295,000
$433/sq ft
Apr 29, 2026
Coming Soon
$1,295,000
$433/sq ft
Smart MLS #170402857
Jun 25, 2021
Sold
$889,000
$298/sq ft
May 23, 2021
Listed
$849,000
$284/sq ft
Conveniently located close to both downtown Stamford and Greenwich and the Merritt Parkway, this North Stamford Contemporary is a gorgeous retreat with great light. It marries comfortable elegance and modern sophistication. Welcome to 28 Pony Trail Road. Featuring: New roof, siding and deck New well pump and piping to house Newly paved asphalt driveway New water softener Whole house generator with automatic failover 15 zone irrigation system Custom lighting and high-end fixtures throughout with Lutron automation Solid wood doors with Baldwin hardware Custom chef’s kitchen by Deane Custom flooring Hot water circulator Walk-in pantry with California Closet system Skylights throughout, including 3 large automated skylights on main level Large deck, accessible from 3 different areas--seamlessly extends living from inside to outside Flexible configuration: ** Primary (or large 4th) bedroom with walk-in closet and ensuite bathroom and sitting room on main level ** 2nd floor Primary bedroom suite with two walk-in closets and ensuite bathroom Vaulted ceilings, open floor plan and tons of natural light Large first floor office/study Washer/dryer hookups on 1st floor and basement 2 park-like acres with babbling brook Invisible fence for pet containment Large, attached 2-car garage with epoxy-coated floor and ample storage space
GMLS #81766
Jun 10, 2017
Delisted
—
Mar 27, 2012
Listed
$810,000
$271/sq ft
Public Records
Aug 1, 2012
Sold
$775,000
$259/sq ft
Smart MLS #98528582
Feb 19, 2012
Listed
$810,000
$271/sq ft
Public Records
Apr 19, 2004
Sold
$853,000
$285/sq ft
GMLS #55182
Jan 5, 2004
Listed
$869,000
$291/sq ft
Smart MLS #98183778
Jan 5, 2004
Listed
$869,000
$291/sq ft
Public Records
Mar 20, 1996
Sold
$375,000
$126/sq ft
Smart MLS #94000032
Feb 5, 1995
Listing Removed
—
Jan 5, 1994
Listed
$489,000
$164/sq ft
Smart MLS #95000266
Jan 4, 1995
Listed
$395,000
$132/sq ft
Smart MLS #95071745
Jan 5, 1995
Listing Removed
—
Jan 5, 1994
Listed
$489,000
$164/sq ft
Year
Property tax
Land + Additions
Assessment*
2022
$11,435 (+1.4%)
$210,010 + $224,280
$434,290
2021
$11,279 (+2.5%)
$210,010 + $224,280
$434,290
2020
$11,001
$210,010 + $224,280
$434,290
2019
$11,001 (+3.6%)
$210,010 + $224,280
$434,290
2018
$10,618 (−18.7%)
$210,010 + $224,280
$434,290
2017
$13,054 (+3.1%)
$289,810 + $220,320
$510,130
2016
$12,661 (+6.5%)
$289,810 + $220,320
$510,130
2014
$11,891
$289,810 + $220,320
$510,130
Public record
Public record
Zoning
Beds
4
Baths
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
2 Acres
Year renovated
—
Sq. Ft.
2,988
Year built
1978
Style
Single Family Residential
County
Fairfield County
APN
338639
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 12, 2023.
RA-3
Single Family Districts, Very Low Density
The purpose of these districts is to set aside and protect areas which have been or may be developed predominantly for single family dwellings on large Lots in a rural setting. Certain other uses are also permitted as-of-right or by Special Permit subject to adequate conditions and safeguards. It is intended that all uses permitted in these districts be compatible with single family Development and consistent with local Street characteristics, the use and protection of private water and sewer facilities (where public facilities are unavailable) and the level of other public services. it is hereby found and declared, further, that these regulations are necessary to the protection of these areas and that their protection is essential to the maintenance of a balanced community of sound residential area of diverse types.
Permitted uses
Include but are not limited to:
Housing-Single unit
Housing-Senior
Educational/school
Communications tower
Property details
Parking
Garage Information
Garage & Parking: Attached Garage
Garages Number: 2
Interior
Interior Information
Total Rooms: 8
Laundry Room Location: 2 locations-main level and basement
Laundry Room Info: Lower Level, Main Level
In-Law Apartment: No
Cooling System: Central Air
Appliances Included: Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher
Bathroom Information
# of Baths (Full): 3
# of Baths (Half): 1
Bedroom Information
Beds Total: 4
Room Information
Basement Description: Full, Unfinished
Has Attic
Attic Description: Access Via Hatch
Exterior
Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Wood
Exterior Features: Deck, Underground Sprinkler
Lot Information
Lot Description: Lightly Wooded
Building Information
Foundation Type: Concrete
Construction Description: Frame
Property Information
Radon Mitigation Air
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2988
Financial
Assessments Information
Assessed Value: $561,220
Utilities
Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Electric
Heat Type: Hot Air
Heat Fuel Type: Oil, Propane
Fuel Tank Location: Above Ground
Energy Features: Generator, Programmable Thermostat, Ridge Vents, Storm Doors, Thermopane Windows
Location
School Information
Middle Jr High School: Cloonan
High School: Westhill
Elementary School: Roxbury
Location Information
State: Connecticut
Directions: Farms Rd to Pony Trail Rd. House on left
County: Fairfield
Public facts
Beds: 4
Baths: 3.5
Sq. Ft.: 2,988
Stories: 2.0
Lot Size: 2 acres
Style: Single Family Residential
Year Built: 1978
Year Renovated: —
County: Fairfield County
APN: 338639
Home facts updated by county records on Jul 12, 2023
Other
Documents & Disclosures
Supplement Count Public: 2
Around this home
Schools
Roxbury School
Public K-5 • Assigned • 3.3mi
4/10
Cloonan School
Public 6-8 • Assigned • 5.5mi
4/10
Westhill High School
Public 9-12 • Assigned • 3.2mi
3/10
Provided by GreatSchools
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
5/10 Heat Factor
7 days above 99° expected this year, 16 days in 30 years
6/10 Wind Factor
56% chance of strong winds in next 30 years
4/10 Air Factor
5 unhealthy days expected this year, 7 days in 30 years
Provided by First Street
Historical weather
Stamford, CT • 06903
Average low and high temperatures (°F)
35
21
38
22
53
33
62
43
70
51
82
61
86
68
81
60
75
57
66
46
54
37
40
26
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
84/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.1 hrs
5.8 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.25M – $1.52M
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