19 Skymeadow Drive
Stamford, Connecticut 06903
- Beds
- 5
- Baths
- 4
- SqFt
- 5,133
- Acres
- 3.47
- Year Built
- 1870
- Neighborhood
- North Stamford
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
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
$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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.