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Sold for $1,900,000 on 07/07/25
  • $1,900,000

    2 Sleepy Hollow Road, New Canaan, CT 06840

    4beds
    5,658sqft
    Single Family Residence
    Built in 1981
    2.62 Acres Lot
    $1,906,100 Zestimate®
    $336/sqft
    $8,510 Estimated rent

    What's special

    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.

    Zillow last checked: 7 hours ago

    Listing updated: July 07, 2025 at 01:38pm

    Listed by:

    Richard Tanner,

    Houlihan Lawrence

    Bought with:

    Leslie Razook, RES.0784934

    William Pitt Sotheby's Int'l

    Source: Smart MLS,MLS#: 24085668MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 3
    • Full bathrooms: 3
    Primary bedroom
    • Features: Balcony/Deck, Stall Shower, Whirlpool Tub, Walk-In Closet(s), Hardwood Floor
    • Level: Main
    • Area: 360 Square Feet
    • Dimensions: 15 x 24
    Bedroom
    • Features: Vaulted Ceiling(s), Walk-In Closet(s), Hardwood Floor
    • Level: Main
    • Area: 315 Square Feet
    • Dimensions: 15 x 21
    Bedroom
    • Features: Vaulted Ceiling(s), Walk-In Closet(s), Hardwood Floor
    • Level: Upper
    • Area: 169 Square Feet
    • Dimensions: 13 x 13
    Bedroom
    • Features: Vaulted Ceiling(s), Walk-In Closet(s), Hardwood Floor
    • Level: Upper
    • Area: 180 Square Feet
    • Dimensions: 12 x 15
    Den
    • Features: Vaulted Ceiling(s), Bookcases, Hardwood Floor
    • Level: Upper
    • Area: 165 Square Feet
    • Dimensions: 11 x 15
    Family room
    • Features: Vaulted Ceiling(s), Hardwood Floor
    • Level: Upper
    • Area: 306 Square Feet
    • Dimensions: 17 x 18
    Kitchen
    • Features: 2 Story Window(s), Cathedral Ceiling(s), Breakfast Nook, Sliders, Hardwood Floor
    • Level: Main
    • Area: 572 Square Feet
    • Dimensions: 22 x 26
    Living room
    • Features: 2 Story Window(s), Vaulted Ceiling(s), Balcony/Deck, Dining Area, Fireplace, Hardwood Floor
    • Level: Main
    • Area: 736 Square Feet
    • Dimensions: 23 x 32
    Loft
    • Level: Third,Other
    • Area: 126 Square Feet
    • Dimensions: 9 x 14
    Loft
    • Level: Third,Other
    • Area: 90 Square Feet
    • Dimensions: 6 x 15
    Office
    • Features: Hardwood Floor
    • Level: Main
    • Area: 180 Square Feet
    • Dimensions: 12 x 15
    Rec play room
    • Features: Skylight, Wall/Wall Carpet
    • Level: Lower
    • Area: 1026 Square Feet
    • Dimensions: 27 x 38
    Heating
    • Forced Air, Propane
    Cooling
    • Central Air, Zoned
    Appliances
    • Included: Cooktop, Oven, Subzero, Dishwasher, Washer, Dryer, Water Heater, Tankless Water Heater
    • Laundry: Main Level
    Features
    • Sound System, Open Floorplan, Smart Thermostat
    • Windows: Thermopane Windows
    • Basement: Partial,Heated,Storage Space,Cooled,Partially Finished,Walk-Out Access
    • Number of fireplaces: 1
    Interior area
    • Total structure area: 5,658
    • Total interior livable area: 5,658 sqft
    • Finished area above ground: 5,050
    • Finished area below ground: 608

    Property

    Parking
    • Total spaces: 3
    • Parking features: Attached, Garage Door Opener
    • Attached garage spaces: 3
    Features
    • Patio & porch: Deck, Patio
    • Exterior features: Rain Gutters, Garden, Lighting, Underground Sprinkler
    Lot
    • Size: 2.62 Acres
    • Features: Wetlands, Borders Open Space, Cul-De-Sac, Landscaped, Rolling Slope, In Flood Zone
    Details
    • Parcel number: 187541
    • Zoning: 2AC
    • Other equipment: Generator

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Contemporary
    • Property subtype: Single Family Residence
    Materials
    • Shingle Siding
    • Foundation: Concrete Perimeter
    • Roof: Asphalt
    Condition
    • New construction: No
    • Year built: 1981

    Utilities & green energy

    • Sewer: Septic Tank
    • Water: Well
    • Utilities for property: Cable Available
    Green energy
    • Energy efficient items: Thermostat, Windows

    Community & neighborhood

    Security
    • Security features: Security System
    Location
    • Region: New Canaan
    Services availability
    Sell for more on Zillow
    Get a free Zillow Showcase℠ listing and you could sell for .
    $1,906,100
    2% more+ $38,122
    With Zillow Showcase(estimated)
    $1,944,222