Discover this stunning five-bedroom contemporary on a premier quiet New Canaan cul-de-sac- just five minutes from town. Soaring ceilings and expansive glass windows flood the open floor plan with natural light, backed by lush landscaping for total privacy. Step into the dramatic living room anchored by a custom gas fireplace. Move seamlessly to the sunlit dining area and custom wood-paneled kitchen with new appliances, walk-in pantry, and breakfast nook-opening to a patio and enclosed garden and lawn, perfect for effortless entertaining. The first-floor primary retreat boasts a sitting area, spa-like bath, and large walk-in closet. Sip morning coffee or catch sunsets overlooking your own nature preserve from the wraparound deck. Nearby are a private office and guest bedroom. Upstairs: three generous bedrooms and vaulted media room. The light-filled walk-out lower level features gym/exercise space and a rec room ready for a wood-burning stove. Mudroom and storage areas add flexibility. All floors were refinished or replaced. A pristine utility room includes recently installed propane heat, on demand hot water and whole house generator. Fiber optic connected and security system upgraded. The oversized three-car garage with high ceilings and epoxy floors stores bikes and gear easily. Owners shared their inspired property vision images (onsite) planned before their transfer. Don't miss this incredible opportunity. Town has approved 5 bedroom designation. Approval paperwork available in documents. All measurements approximate. Only the lower level is in a flood zone. The previous owner and this owner have never experienced water intrusion. A transferable flood policy is available currently $1105.06 per year. Previous owners kept a canoe for pond access. Land trust trails and the magical firefly preserve are a short walk.
Under contract
$2,195,000
2 Sleepy Hollow Road, New Canaan, CT 06840
5beds
5,658sqft
Single Family Residence
Built in 1981
2.62 Acres Lot
$2,360,700 Zestimate®
$388/sqft
$-- HOA
What's special
- 45 days |
- 146 |
- 2 |
Zillow last checked:
Listing updated:
Listed by:
Leslie Razook (203)918-4452,
William Pitt Sotheby's Int'l 203-966-2633
Source: Smart MLS,MLS#: 24166322
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 3
Primary bedroom
- Features: High Ceilings, Balcony/Deck, Full Bath, Walk-In Closet(s)
- Level: Main
Bedroom
- Features: Built-in Features, Full Bath
- Level: Main
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Dining room
- Features: High Ceilings, Balcony/Deck, Built-in Features, Gas Log Fireplace, Patio/Terrace
- Level: Main
Kitchen
- Features: 2 Story Window(s), High Ceilings, Built-in Features, Pantry, Hardwood Floor
- Level: Main
Living room
- Features: 2 Story Window(s), Vaulted Ceiling(s), Balcony/Deck, Gas Log Fireplace, Hardwood Floor
- Level: Main
Media room
- Features: Vaulted Ceiling(s), Beamed Ceilings, Built-in Features
- Level: Upper
Office
- Level: Main
Rec play room
- Features: Sliders
- Level: Lower
Heating
- Forced Air, Propane
Cooling
- Central Air, Ductless
Appliances
- Included: Electric Cooktop, Oven, Refrigerator, Subzero, Dishwasher, Washer, Dryer, Electric Water Heater, Water Heater, Tankless Water Heater
- Laundry: Main Level
Features
- Wired for Data, Open Floorplan
- Basement: Full,Heated,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
- Exterior features: Garden
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Pond
Lot
- Size: 2.62 Acres
- Features: Wetlands, Level, Cul-De-Sac, Landscaped, Rolling Slope, In Flood Zone
Details
- Parcel number: 187541
- Zoning: 2AC
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Contemporary,Modern
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1981
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
HOA
- Has HOA: No
Location
- Region: New Canaan
Financial & listing details
- Price per square foot: $388/sqft
- Tax assessed value: $1,107,750
- Annual tax amount: $18,488
- Date on market: 5/11/2026
- Exclusions: see inclusion/ exclusion sheet
Estimated market value
$2,360,700
$2.24M - $2.48M
$7,590/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/27/2026 | Pending sale | $2,195,000$388/sqft |
Source:  Smart MLS #24166322 Report a problem | ||
| 5/14/2026 | Listed for sale | $2,195,000+15.5%$388/sqft |
Source: Smart MLS #24166322 Report a problem | ||
| 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 | ||
| 6/6/2019 | Price change | $1,075,000-6.5%$190/sqft |
Source: William Pitt Sotheby's International Realty #170178546 Report a problem | ||
| 4/1/2019 | Listed for sale | $1,150,000-8%$203/sqft |
Source: William Pitt Sotheby's International Realty #170178546 Report a problem | ||
| 8/3/2017 | Listing removed | $7,000$1/sqft |
Source: William Pitt Sotheby's International Realty #99189832 Report a problem | ||
| 7/29/2017 | Listed for rent | $7,000$1/sqft |
Source: William Pitt Sotheby's International Realty #99189832 Report a problem | ||
| 7/27/2017 | Listing removed | $1,250,000$221/sqft |
Source: William Pitt Sotheby's International Realty #99189623 Report a problem | ||
| 6/13/2017 | Listed for sale | $1,250,000-2%$221/sqft |
Source: William Pitt Sotheby's International Realty #99189623 Report a problem | ||
| 5/29/2013 | Sold | $1,275,000-8.6%$225/sqft |
Source: Smart MLS #99016602 Report a problem | ||
| 2/13/2013 | Listed for sale | $1,395,000+74.4%$247/sqft |
Source: William Raveis Real Estate #99016602 Report a problem | ||
| 12/2/1994 | Sold | $800,000$141/sqft |
Source: Public Record 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 |
| 2022 | $16,162 +1.2% | $879,830 |
| 2021 | $15,978 | $879,830 |
| 2020 | $15,978 -0.4% | $879,830 |
| 2019 | $16,048 +5.8% | $879,830 -1.6% |
| 2018 | $15,169 +1.7% | $894,390 |
| 2017 | $14,909 +0.3% | $894,390 -1.8% |
| 2016 | $14,860 +2% | $911,120 |
| 2015 | $14,569 +2.9% | $911,120 |
| 2014 | $14,159 -23.9% | $911,120 -28.5% |
| 2013 | $18,597 +3.6% | $1,274,630 +0% |
| 2012 | $17,946 +1.7% | $1,274,600 |
| 2011 | $17,653 +2% | $1,274,600 |
| 2010 | $17,309 +1.7% | $1,274,600 |
| 2009 | $17,016 -1.9% | $1,274,600 +11.1% |
| 2008 | $17,353 +4% | $1,147,700 |
| 2007 | $16,688 +3.6% | $1,147,700 |
| 2006 | $16,114 +4.9% | $1,147,700 |
| 2005 | $15,368 +5.8% | $1,147,700 |
| 2004 | $14,530 +3.5% | $1,147,700 +14.4% |
| 2003 | $14,034 +6.9% | $1,003,170 +59.5% |
| 2001 | $13,134 +2% | $629,000 0% |
| 2000 | $12,882 +5% | $629,020 |
| 1999 | $12,266 | $629,020 |
Find assessor info on the county website
Monthly payment
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Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 06840
Nearby schools
GreatSchools rating
- 10/10East SchoolGrades: K-4Distance: 1.8 mi
- 10/10Saxe Middle SchoolGrades: 5-8Distance: 2.9 mi
- 10/10New Canaan High SchoolGrades: 9-12Distance: 3.1 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.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Fairfield County
- New Canaan
- 06840
- 2 Sleepy Hollow Road
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