2 Sleepy Hollow Road New Canaan, CT $ 2,195,000
2 Sleepy Hollow Road
$ 2,195,000
Recently Listed
Open House 5/17 1pm - 3pm
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2 Sleepy Hollow Road

New Canaan, CT, 06840
$ 2,195,000
Bedrooms5 Baths3.0 Sq 5,658

Monthly Estimate*

$ 13,515

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Single Family Home for sale in New Canaan, CT

for $2,195,000 with 5 bedrooms and 3 full baths. This 5,658 square foot home was built in 1981 on a lot size of 2.62.

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.

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Open House

5/17/2026 1:00 PM - 3:00 PM
2 Sleepy Hollow Road New Canaan, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 2,195,000

Bedrooms

5

Full Bath

3

Property Type

Single Family

Taxes

$ 18,488

Style

Lot Size

2.62

Year Built

1981

Town/City

New Canaan

MLS | Web ID

24166322

Features
General
Zoning 2AC
Neighborhood N/A
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.62
Directions Laurel Rd to Sleepy Hollow
High School New Canaan
City New Canaan
Elementary School East
Sq Ft Total 5658
DOM 2
Year Built 1981
Exclusions see inclusion/ exclusion sheet
Style Contemporary Modern
Year Built Source Public Records
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Interior
Cooling System Central Air Split System
Total Rooms 12
Basement Description Full Heated Partially Finished Walk-out
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Exterior
Water Source Private Well
Lot Description Some Wetlands Level Lot On Cul-De-Sac Professionally Landscaped Rolling
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* Excluded Features
List By
Leslie Razook

Listing Agent

William Pitt Sotheby's Int'l

Broker

lrazook@williampitt.com

Email

Affordability Calculator

$15,056
Per Month
90%
10%
0%
Monthly Principal & Interest
$13,515
Monthly Property Taxes
$1,541
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4778078 Elementary School
3041765 Middle School
New Canaan High School High School
Pricing History
DatePricePrice ChangeDescription
5/11/2026$2,195,000 Listed Price

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2 Sleepy Hollow Road, New Canaan, CT, 06840 is a Single Family Home for sale at $2,195,000 with 5,658 sqft and a lot size of 2.62. 2 Sleepy Hollow Road has 5 bedrooms, 3.0 baths, and was built in 1981. The property's zip code is 06840 which is in New Canaan, CT