33 days on market
Under Contract
More about this Property

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2 Sleepy Hollow Road, New Canaan CT 06840

Current Price: $1,999,000

4 beds 3 baths 5658 sq. ft

Last Update: 6/20/2025

Property Type: Single Family For Sale

Public Remarks

Spectacular contemporary with soaring ceilings and walls of windows on one of New Canaans 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 houses 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 Canaans 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.

Map to Property at 2 Sleepy Hollow Road, New Canaan CT 06840


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

Residential Property Information for 2 Sleepy Hollow Road, New Canaan CT 06840

MLS #: 24085668

Style: Contemporary

Color:

Total Rooms:

Bedrooms: 4

Bathrooms: 3

Acres: 2.62

Year Built: 1981 (Public Records)

New Construction: No/Resale

Home Warranty Offered:

Property Tax: $17,879

Zoning: 2AC

Mil Rate:

Assessed Value: $1,107,750 

Potential Short Sale:

Square Footage: Estimated HEATED Sq.Ft. above grade is 5050; below grade sq feet total is 608; total sq ft is 5658

Features
Appliances Incl.: Cook Top,Wall Oven,Subzero,Dishwasher,Washer,Dryer
Laundry Location & Info: Main Level  off Kitchen
Fireplaces: 1
Energy Features: Generator,Programmable Thermostat,Thermopane Windows
Interior Features: Audio System,Auto Garage Door Opener,Cable - Available,Open Floor Plan,Security System
Energy Features: Generator,Programmable Thermostat,Thermopane Windows
Home Automation: Built In Audio,Thermostat(s)
Basement Desc.: Partial,Heated,Storage,Cooled,Partially Finished,Walk-out
Exterior Siding: Shingle
Exterior Features: Deck,Gutters,Garden Area,Lighting,Underground Sprinkler,Patio
Foundation: Concrete
Roof: Asphalt Shingle
Parking Spaces: 3
Garage/Parking Type: Under House Garage
Swimming Pool: 0
Waterfront Feat.: Not Applicable
Lot Description: Some Wetlands,Borders Open Space,On Cul-De-Sac,Professionally Landscaped,Rolling
In Flood Zone: 1
Occupied: Owner
Utility Information

Hot Water System

Heat Type:

Fueled By: Hot Air.

Cooling: Central Air,Zoned

Fuel Tank Location: In Ground

Water Service: Private Well

Sewage System: Septic

School Information

Elementary: East

Intermediate:

Middle: Saxe Middle

High School: New Canaan

Marketing History

Current List Price: $1,999,000

Original List Price: $1,999,000

DOM: 33

Listing Date: 4/3/2025

Last Updated: 6/2/2025 4:05:12 PM

Listing Agent and Broker

List Agent Name: Richard Tanner

List Office Name: Houlihan Lawrence