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$1,900,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 5,658 Sq. Ft.
  • 3 Car Garage
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Spectacular contemporary with soaring ceilings and walls of windows on one of New Canaan's most coveted cul-de-sacs. Purposefully set to capture light, 2 Sleepy Hollow delights on all four floors, with dramatic design and inspiring spaces. The 4-5 bedroom 5600sf home is defined by a remarkable double-story 270 degree arc that encompasses living, dining and the kitchen, all bathed with south and western exposures and ready to live and entertain. Adjacent is the home office and two bedrooms including a spacious primary suite with sitting area and one of the house's three walk-in closets. Upstairs are two more bedrooms with an option for a third and a remarkable floating den/media room with views to below. And above, are two intriguing and whimsical lofts accessible by one of the bedrooms. In the lower level is the 3 car garage, spotless utility rooms for systems and storage, and a fully finished walk-out gym and rec room with giant windows that bring the outside in. Efficiency is also paramount, with recently installed propane heat and on-demand hot water and a full-house generator. Outside features extensive decks and patios that overlook the irrigated gardens and lawns. All this is a 1 minute walk to the Firefly Land Trust trails and a 5 minute drive to downtown New Canaan's cherished village, shopping and the award-winning schools. This is truly open plan living wrapped in exciting architecture that has to be seen. Extensive upgrade list upon request.

Full Property Details for 2 Sleepy Hollow Rd

General

  • Sold For: $1,900,000
  • Taxes: (July 2024-June 2025)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24085668
  • Added to Site: 323 day(s) ago

Interior

  • Number of Rooms: 12
  • Rooms/Areas: Exercise Room
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Cook Top, Wall Oven, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Balcony/Deck, Stall Shower, Whirlpool Tub, Walk-In Cl, 24 x 15, Main
  • Bedroom 1: Bedroom - Vaulted Ceiling, Walk-In Closet, Hardwood Floor, 21 x 15, Main
  • Bedroom 2: Bedroom - Vaulted Ceiling, Walk-In Closet, Hardwood Floor, 13 x 13, Upper
  • Bedroom 3: Bedroom - Vaulted Ceiling, Walk-In Closet, Hardwood Floor, 15 x 12, Upper

Other Rooms

  • Living Room: Living Room - 2 Story Window(s), Vaulted Ceiling, Balcony/Deck, Dining Area, Fireplace, Hardwood Floor, 32 x 23, Main
  • Family Room: Family Room - Vaulted Ceiling, Hardwood Floor, 18 x 17, Upper
  • Kitchen: Kitchen - 2 Story Window(s), Cathedral Ceiling, Breakfast Nook, Sliders, Hardwood Floor, 26 x 22, Main
  • Office: Office - Hardwood Floor, 15 x 12, Main
  • Den: Den - Vaulted Ceiling, Book Shelves, Hardwood Floor, 15 x 11, Upper
  • Loft: Loft - On 3rd Floor, 14 x 9, Other
  • Game room: Yes
  • Game Room: Rec/Play Room - Skylight, Wall/Wall Carpet, 38 x 27, Lower
  • Rec Room: Skylight, Wall/Wall Carpet, 38 x 27, Lower
  • Laundry: Main Level

Exterior

  • Exterior Features: Deck, Gutters, Garden Area, Lighting, Underground Sprinkler, Patio

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Parking: Under House Garage

Location

  • County: Fairfield
  • Driving Directions: North on Canoe Hill to North on Laurel Road. Make left turn on to Sleepy Hollow Road and the house is first on the left

School Information

  • Elementary School: East
  • Middle School: Saxe Middle
  • High School: New Canaan

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Air, Propane
  • Heating Fuel: Propane
  • Water Heater: Propane, Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Contemporary
  • Construction Status: No/Resale
  • Exterior Const.: Shingle
  • Basement Desc.: Partial, Heated, Storage, Cooled, Partially Finished, Walk-out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 5,658
  • Above Ground: 5,050 Sq. Ft.
  • Below Ground: 608 Sq. Ft.
  • Year Built: 1981

Lot Features

  • Lot Size (Acres): 2.62
  • Zoning: 2AC
  • Lot Description: Some Wetlands, Borders Open Space, On Cul-De-Sac, Professionally Landscaped, Rolling

Green Features

  • Energy Features: Generator, Programmable Thermostat, Thermopane Windows

Financial Considerations

  • Assessment Amount: $1,107,750
  • Tax Year: July 2024-June 2025

Disclosures and Reports

  • Exclusions: Downstairs Refrigerator
  • Flood Zone: Yes
  • Property ID: 187541

Listed by Houlihan Lawrence, Richard Tanner
Sold by William Pitt Sotheby's Int'l, Leslie Razook

Listing agent

— 2 Sleepy Hollow Rd —

  • Richard Tanner

    Houlihan Lawrence

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 2 Sleepy Hollow Rd

School District:New Canaan School District
NameGradesDistance
East School
54 Little Brook Road, New Canaan, CT 06840
K-41.8 mi
Saxe Middle School
468 South Avenue, New Canaan, CT 06840
5-82.8 mi
New Canaan High School
11 Farm Road, New Canaan, CT 06840
9-123 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2 Sleepy Hollow Rd

Date
Details
Price
Change
Source
7/07/2025
Sold
$1,900,000
-4.95%
MLS
4/03/2025
Listed
$1,999,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Houlihan Lawrence, Richard Tanner
Sold by William Pitt Sotheby's Int'l, Leslie Razook

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2 Sleepy Hollow Road, New Canaan, CT 06840 (MLS# 24085668) is a Single Family property that was sold at $1,900,000 on July 07, 2025. Want to learn more about 2 Sleepy Hollow Road? Do you have questions about finding other Single Family real estate for sale in New Canaan? You can browse all New Canaan real estate or contact a Coldwell Banker agent to request more information.