19 Skymeadow Drive, Stamford, Connecticut 06903

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.

Flood risk: check the FEMA flood map for this address.

Schools

Taxes

Interior

Building & Exterior

Lot & Land

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

What's nearby

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $1,675,000, ranging $1,225,000 to $2,000,000.

Within a 15-minute walk, sold in the last year
• 3 Mary Joy Lane4 bd · 4 ba · 3,921 sq ft · 0.1 mi away
  $1,422,000$362/sq ft2026-08-10
• 161 North Stamford Road4 bd · 4 ba · 3,854 sq ft · 0.2 mi away
  $1,675,000$434/sq ft2025-10-02
• 37 Pinner Lane4 bd · 4 ba · 4,767 sq ft · 0.2 mi away
  $1,225,000$256/sq ft2025-11-21
• 49 Pinner Lane4 bd · 4 ba · 5,217 sq ft · 0.3 mi away
  $1,850,000$354/sq ft2026-01-13
• 40 Cascade Road5 bd · 5 ba · 6,370 sq ft · 0.3 mi away
  $2,000,000$313/sq ft2025-09-15

Public record

From the Stamford assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

More homes in Stamford

Closest in price to this one.

• 21A South Brook Drive4 bed · 4 bath · 6,103 sq ft$3,389,000
• 25 Sagamore Road6 bed · 6 bath · 7,310 sq ft$3,295,000
• 22 Ocean Drive North4 bed · 5 bath · 3,866 sq ft$3,100,000
• 62-64 Wallacks Drive4 bed · 5 bath · 4,599 sq ft$2,995,000
• 40 Rogers Road6 bed · 4 bath · 5,105 sq ft$2,950,000
• 58 Rogers Road5 bed · 5 bath · 5,618 sq ft$3,800,000

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