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19 Skymeadow Drive

Stamford, Connecticut 06903

PENDING$3,345,000
Beds
5
Baths
4
SqFt
5,133
Acres
3.47
Year Built
1870
Matt Caiola

Matt Caiola

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Guest HouseTennis CourtPool3-Car Garage4 FireplacesVirtual Tour

About This Home

Welcome to The Benjamin Weed House, a distinguished and storied estate set across 3.5 exquisite acres-where historic provenance meets refined modern living. Expanded and meticulously curated over time, this exceptional five-bed, four-bath residence offers a rare blend of architectural integrity and contemporary sophistication. Inside, soaring ceilings, wide-plank hardwood floors, and masterful craftsmanship create an atmosphere of understated elegance. The chef's kitchen is both functional and beautiful, appointed with a Sub-Zero refrigerator, Wolf cooktop, granite countertops, and an expansive dining area designed for effortless entertaining. The grounds are nothing short of extraordinary-evoking the romance of an English country garden with fountain, mature specimen plantings, hydrangeas, and peonies woven throughout the landscape. A collection of thoughtfully designed outdoor amenities elevates the estate to a private retreat: a newly constructed post-and-beam barn in pine and cedar, a fully renovated guest house with kitchen and bath, a tennis court, and a resort-style gunite pool. The stone terrace-complete with fireplace, grill, and pergola-creates an idyllic setting for al fresco dining. A detached 3 car garage is complemented by a beautifully finished second-floor flex space, ideal for a studio, office, or wellness retreat. The new guest house offers a luxurious and private accommodation for extended family and guests.

Key Facts

City/Town
Stamford
Neighborhood
North Stamford
Property / Style
Single Family · Colonial
Year Built
1870
Days on Market
105 days
Beds
5
Baths
4 full
Living Area
5,133 sq ft
Lot Size
3.47 acres
Garage / Parking
3 garage
Property Taxes
$25,039 / 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

$3.35M

vs $1.20M median

2.8× the median

Price / Sq Ft

$652

vs $414 median

57.5% above median

Days on Market

105 days

vs 39 days median

66 days longer 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

19 Skymeadow Drive, Stamford, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$20,257

per month

  • Principal & Interest$17,055
  • Property Taxes$2,087
  • Insurance$1,115
  • HOA$0

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

Location

City/Town
Stamford
Neighborhood
North Stamford
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1870
New Construction
No/Resale
Living Area
5,133 sq ft

Schools

Elementary
Northeast
High
Westhill

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central AirZoned
Fireplaces
4
Laundry Location
upper
Appliances
Cook TopWall OvenRefrigeratorSubzeroIcemakerDisposalWasherDryer
Basement
FullPartially Finished
In-Law Apartment
PossibleDetached

Exterior & Lot

Lot Size
3.47 acres
Zoning
RA1
Garage / Parking
3 garage spacesDetached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Pool
GuniteHeatedSalt WaterIn Ground Pool
Construction
Wood
Color
White
Roof
Wood Shingle
Foundation
Concrete
Exterior Features
GrillTennis CourtBarnGuttersGarden AreaGuest HouseFrench DoorsPatio
Lot Description
Lightly WoodedCleared

Listing & Financials

Property Taxes
$25,039 / Annually
Days on Market
105
MLS #
24166734
MLS Status
Under Contract
Financing
Assumable,FHA,VA

Similar Properties

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Listed By

Laurie Cingari

(203) 273-9090

Berkshire Hathaway NE Prop.

(203) 329-2111

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 8:01 AM UTC.