Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$3,345,000

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 5,133 Sq. Ft.
  • 3 Car Garage
See This Home
Save This Home
See This Home
Save 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.

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: 4/21/2026
  • Added to Site: 46 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

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

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

Schools serving 19 Sky Meadow Dr

School District:Stamford School District
NameGradesDistance
Northeast School, Stamford, CT
82 Scofieldtown Road, Stamford, CT 06903
K-51.3 mi
Turn Of River School
117 Vine Road, Stamford, CT 06905
6-83 mi
Westhill High School, Stamford, CT
125 Roxbury Road, Stamford, CT 06902
9-123.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

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.

Estimate the Cost for 19 Sky Meadow Dr

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Berkshire Hathaway NE Prop., Laurie Cingari

Similar Properties near 19 Sky Meadow Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

19 Sky Meadow Dr, Stamford, CT 06903 - Photo 1
$3,345,000

19 Sky Meadow Dr  Stamford, CT 06903

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 5,133
    Sq. Ft.
Listed by BHHS New England Properties
21A South Brook Dr, Stamford, CT 06903 - Photo 1
$3,389,000

21A South Brook Dr  Stamford, CT 06903

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 6,103
    Sq. Ft.
Listed by Elaine Voss (914) 774-5459 and Compass Connecticut, LLC
469 Taconic Rd, Greenwich, CT 06831 - Photo 1
$3,425,000

469 Taconic Rd  Greenwich, CT 06831

  • Single Family
  • Active
  • 4
    Beds
  • 5
    Total Baths
  • 4,616
    Sq. Ft.
Listed by BHGRE Shore & Country
5 Middlesex Rd, Darien, CT 06820 - Photo 1
$3,245,000

5 Middlesex Rd  Darien, CT 06820

  • Single Family
  • Active
  • Updated 4 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 6,195
    Sq. Ft.
Listed by William Raveis Real Estate

Just Listed near 19 Sky Meadow Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

27 Park Ave, Old Greenwich, CT 06870 - Photo 1 Just Listed
$1,795,000

27 Park Ave  Old Greenwich, CT 06870

  • Lots/Land
  • Active
  • Updated 2 days ago
  • 0.22
    Acres
Listed by Sotheby's International Realty
22 North Way, Old Greenwich, CT 06870 - Photo 1 Just Listed
$13,500,000

22 North Way  Old Greenwich, CT 06870

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 4
    Total Baths
  • 3,330
    Sq. Ft.
Listed by Houlihan Lawrence
10 MacArthur Dr, Old Greenwich, CT 06870 - Photo 1 Just Listed
$1,600,000
Open House

10 MacArthur Dr  Old Greenwich, CT 06870

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,671
    Sq. Ft.
Listed by Compass Connecticut, LLC
27 Park Ave, Old Greenwich, CT 06870 - Photo 1 Just Listed
$1,795,000

27 Park Ave  Old Greenwich, CT 06870

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 1
    Total Bath
  • 1,080
    Sq. Ft.
Listed by Sotheby's International Realty

Price Reduced near 19 Sky Meadow Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

118 Shore Rd, Old Greenwich, CT 06870 - Photo 1 Price Reduced
-$200,000 (-4.57%)
$4,175,000

118 Shore Rd  Old Greenwich, CT 06870

  • Single Family
  • Active
  • Updated 11 hours ago
  • 5
    Beds
  • 5
    Total Baths
  • 3,384
    Sq. Ft.
Listed by Sotheby's International Realty
518 Hoyt St, Darien, CT 06820 - Photo 1 Price Reduced
-$451,000 (-18.41%)
$1,999,000
Open House

518 Hoyt St  Darien, CT 06820

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 4
    Total Baths
  • 3,704
    Sq. Ft.
Listed by Ben Fitts (678) 362-6330
28 Shields Rd, Darien, CT 06820 - Photo 1 Price Reduced
-$305,000 (-6.63%)
$4,295,000

28 Shields Rd  Darien, CT 06820

  • Single Family
  • Active
  • Updated 10 hours ago
  • 6
    Beds
  • 8
    Total Baths
  • 6,274
    Sq. Ft.
Listed by Compass Connecticut, LLC
39 Leeuwarden Rd, Darien, CT 06820 - Photo 1 Price Reduced
-$200,000 (-5.01%)
$3,795,000
Open House

39 Leeuwarden Rd  Darien, CT 06820

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 7
    Total Baths
  • 6,424
    Sq. Ft.
Listed by Brown Harris Stevens

Recent Sales near 19 Sky Meadow Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1580 Ponus Ridge, New Canaan, CT 06840 - Photo 1 Sold
$3,400,000

1580 Ponus Ridge  New Canaan, CT 06840

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 6,388
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Pitt Sotheby's Int'l
24 Clearview Ln, New Canaan, CT 06840 - Photo 1 Sold
$3,700,000

24 Clearview Ln  New Canaan, CT 06840

  • Single Family
  • Closed
  • 6
    Beds
  • 9
    Total Baths
  • 6,476
    Sq. Ft.
Listed by Houlihan Lawrence
Sold by Compass Connecticut, LLC
298 Greenley Rd, New Canaan, CT 06840 - Photo 1 Sold
$3,100,000

298 Greenley Rd  New Canaan, CT 06840

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 4,021
    Sq. Ft.
Listed by Marsha Charles
Sold by Brown Harris Stevens
73 Lake Wind Rd, New Canaan, CT 06840 - Photo 1 Sold
$3,825,000

73 Lake Wind Rd  New Canaan, CT 06840

  • Single Family
  • Closed
  • Updated 14 hours ago
  • 5
    Beds
  • 10
    Total Baths
  • 9,062
    Sq. Ft.
Listed and Sold by AG Prime Realty

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.

Tour this property