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.
Sold for $1,900,000
$1,900,000
2 Sleepy Hollow Road, New Canaan, CT 06840
4beds
5,658sqft
Single Family Residence
Built in 1981
2.62 Acres Lot
$1,954,300 Zestimate®
$336/sqft
$7,590 Estimated rent
Home value
$1,954,300
$1.76M - $2.19M
$7,590/mo
Zestimate® history
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Zillow last checked: 7 hours ago
Listing updated: October 14, 2025 at 07:02pm
Listed by:
Richard Tanner 917-703-7000,
Houlihan Lawrence 203-966-3507
Bought with:
Leslie Razook, RES.0784934
William Pitt Sotheby's Int'l
Source: Smart MLS,MLS#: 24085668
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
Price history
| Date | Event | Price |
|---|---|---|
| 7/7/2025 | Sold | $1,900,000-5%$336/sqft |
Source:  Smart MLS #24085668 Report a problem | ||
| 6/2/2025 | Pending sale | $1,999,000$353/sqft |
Source: Smart MLS #24085668 Report a problem | ||
| 4/4/2025 | Listed for sale | $1,999,000+107.7%$353/sqft |
Source: Smart MLS #24085668 Report a problem | ||
| 8/20/2019 | Sold | $962,500-10.5%$170/sqft |
Source: Smart MLS #170178546 Report a problem | ||
| 7/17/2019 | Pending sale | $1,075,000$190/sqft |
Source: William Pitt Sotheby's International Realty #170178546 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $18,488 +3.4% | $1,107,750 |
| 2024 | $17,879 +7.3% | $1,107,750 +25.9% |
| 2023 | $16,664 +3.1% | $879,830 |
Find assessor info on the county website
Neighborhood: 06840
Nearby schools
GreatSchools rating
- 10/10East SchoolGrades: K-4Distance: 1.8 mi
- 9/10Saxe Middle SchoolGrades: 5-8Distance: 2.8 mi
- 10/10New Canaan High SchoolGrades: 9-12Distance: 3 mi
Schools provided by the listing agent
- Elementary: East
- Middle: Saxe Middle
- High: New Canaan
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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$1,993,386
- Connecticut
- Fairfield County
- New Canaan
- 06840
- 2 Sleepy Hollow Road