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$3,345,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 5,133 Sq. Ft.
  • 3 Car Garage
  • Updated 6 hours ago
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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. New cedar roof 2026.

Full Property Details for 19 Sky Meadow Dr

General

  • Price: $3,345,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24166734
  • Updated: 4/14/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 10
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Appliances: Cook Top, Wall Oven, Refrigerator, Subzero, Icemaker, Disposal, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4
  • Full Bath: Main

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Built-Ins, Dressing Room, Fireplace, Full Bath, Walk-In Closet, Upper
  • Bedroom 1: Bedroom - Bedroom Suite, Main
  • Bedroom 2: Bedroom - 9 ft+ Ceilings, Book Shelves, Built-Ins, Hardwood Floor, Upper
  • Bedroom 3: Bedroom - 9 ft+ Ceilings, Book Shelves, Built-Ins, Hardwood Floor, Upper
  • Bedroom 4: Bedroom - 9 ft+ Ceilings, Built-Ins, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Beams, Fireplace, Wide Board Floor, Main
  • Family Room: Family Room - 9 ft+ Ceilings, Balcony/Deck, Book Shelves, Built-Ins, French Doors, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - 9 ft+ Ceilings, Built-Ins, Granite Counters, French Doors, Pan, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Fireplace, Hardwood Floor, Main
  • Office: Office - 9 ft+ Ceilings, Book Shelves, Built-Ins, Hardwood Floor, Upper
  • Library: Library - 9 ft+ Ceilings, Book Shelves, Built-Ins, Fi, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Remodeled, Lower
  • Rec Room: Remodeled, Lower

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Salt Water, In Ground Pool

Exterior

  • Exterior Features: Grill, Tennis Court, Barn, Gutters, Garden Area, Guest House, French Doors, Patio
  • Color: White

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Parking: Detached Garage

Location

  • County: Fairfield
  • Neighborhood: North Stamford
  • Driving Directions: North on High Ridge Road left on Skymeadow-first right into driveway-pass barn and guest house to Main Residence

School Information

  • Elementary School: Northeast
  • Middle School: Turn of River
  • High School: Westhill

Community

  • Community Name: North Stamford

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Full, Partially Finished
  • Roof: Wood Shingle
  • Attic: Yes
  • Square Feet: 5,133
  • Above Ground: 5,133 Sq. Ft.
  • Year Built: 1870

Lot Features

  • Lot Size (Acres): 3.47
  • Zoning: RA1
  • Lot Description: Lightly Wooded, Cleared

Financial Considerations

  • Assessment Amount: $1,076,030
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 314994

Listed by Berkshire Hathaway NE Prop., Laurie Cingari

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Listing agent

— 19 Sky Meadow Dr —

  • Laurie Cingari

    Berkshire Hathaway NE Prop.

Agent Contact: (203) 273-9090 Office Contact: (203) 329-2111

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Price & Sales History for 19 Sky Meadow Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/13/2026
Listed
$3,345,000
343.05%
MLS
7/14/1992
Sold
$755,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 19 Sky Meadow Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$25,039
4%
$1,076,030
1%
2023
$24,181
-7%
$1,062,430
—
2023
$25,864
1%
$1,057,390
9%
2022
$25,608
2%
$972,560
—
2021
$25,202
3%
$970,420
—
2020
$24,565
—
$969,790
—
2019
$24,565
4%
$969,790
—
2018
$23,711
-1%
$969,790
3%
2017
$24,035
3%
$939,230
—
2016
$23,312
3%
$939,230
—
2015
$22,673
4%
$939,230
—
2014
$21,893
3%
$939,230
—
2011
$21,292
—
$939,230
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Berkshire Hathaway NE Prop., Laurie Cingari

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19 Skymeadow Drive, Stamford, CT 06903 (MLS# 24166734) is a Single Family property with 5 bedrooms and 4 full bathrooms. 19 Skymeadow Drive is currently listed for $3,345,000 and was received on April 13, 2026. Want to learn more about 19 Skymeadow Drive? Do you have questions about finding other Single Family real estate for sale in Stamford? You can browse all Stamford real estate or contact a Coldwell Banker agent to request more information.

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