2 Sleepy Hollow Rd

New Canaan, CT 06840

$2,195,000
Price
5
Beds
5,658 Sq. Ft.
$388 / Sq. Ft.
5,658
Sq. Ft.
$388
per Sq. Ft.
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Under Contract
Under Contract

Description

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...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.
  1. Listed by Leslie Razook • William Pitt Sotheby's Int'l
    P: (203)-918-4452 C: (203)-918-4452 lrazook@williampitt.com

Property Details for 2 Sleepy Hollow Road

Basement Description
Full, Heated, Partially Finished, Walk-out
Direct Waterfront
Yes
Expected Active Date
05-14-2026
Garages Number
3
Neighborhood
N/A
Style
Contemporary, Modern
Garage Parking Info
Attached Garage, Under House Garage
Swimming Pool
No
LISTING UPDATED: 05/27/2026 07:55 PM

Property Details for 2 Sleepy Hollow Road

StatusUnder Contract
MLS #24166322
Days on Market13
Taxes$18,488 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1981
Lot Size2.62 AC / 114,127 SF
CountyFairfield County
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Location

Listing Courtesy of William Pitt Sotheby's Int'l, Leslie Razook
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Building Information for 2 Sleepy Hollow Road

Stories-Year Built1981Building Size-Lot Size2.62 AC / 114,127 SF

Payment Calculator

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$12,479 per month

30 year fixed, 6.36% Interest

Principal and Interest

$10,938

Property Taxes

$1,541

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 2 Sleepy Hollow Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Laurel Rd to Sleepy Hollow
  • Elementary School: East
  • Flood Zone: Yes
  • High School: New Canaan
  • Latitude: 41.173093
  • Longitude: -73.48828
  • Middle Jr High School: Saxe Middle
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $18,488
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Garden Area
  • Waterfront Description: Pond, View
Interior Features
  • Appliances Included: Electric Cooktop, Wall Oven, Refrigerator, Subzero, Dishwasher, Washer, Dryer
  • Attic Description: Walk-In
  • Cooling System: Central Air, Split System
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
  • Laundry Room Info: Main Level
  • Rooms Total: 12
Room 1
  • Room Entry Order: 1
  • Room Features: 2 Story Window(s),Vaulted Ceiling,Balcony/Deck,Gas Log Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Vaulted Ceiling,Beams,Built-Ins
  • Room Level: Upper
  • Room Type: Media Room
Room 3
  • Room Entry Order: 11
  • Room Features: Sliders
  • Room Level: Lower
  • Room Type: Rec/Play Room
Room 4
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Balcony/Deck,Built-Ins,Gas Log Fireplace,Patio/Terrace
  • Room Level: Main
  • Room Type: Dining Room
Room 5
  • Listing Key: 4F23C9A8576ABF04E0631A01100A9912
  • Room Entry Order: 3
  • Room Features: 2 Story Window(s),9 ft+ Ceilings,Built-Ins,Pantry,Hardwood Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 6
  • Room Entry Order: 4
  • Room Level: Main
  • Room Type: Office
Room 7
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Balcony/Deck,Full Bath,Walk-In Closet
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 8
  • Room Entry Order: 6
  • Room Features: Built-Ins,Full Bath
  • Room Level: Main
  • Room Type: Bedroom
Room 9
  • Listing Key: 4F23C9A8576ABF04E0631A01100A9912
  • Room Entry Order: 7
  • Room Level: Upper
  • Room Type: Bedroom
Room 10
  • Room Entry Order: 8
  • Room Level: Upper
  • Room Type: Bedroom
Room 11
  • Room Entry Order: 9
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Elevation Certificate: Yes
  • Exclusions: see inclusion/ exclusion sheet
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Fuel Tank Location: In Ground
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1981
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Est Heated Below Grade: 608
  • Living Area SQFT Per Public Records: 5050
Lot Information
  • Lot Description: Some Wetlands, Level Lot, On Cul-De-Sac, Professionally Landscaped, Rolling
  • Parcel Number: 187541
  • Sq Ft Est Heated Above Grade: 5050.0
  • Sq Ft Total: 5658.0
  • Zoning: 2AC
Utilities
  • Heat Fuel Type: Propane
  • Hot Water Description: Electric, Propane, Tankless Hotwater
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 2 Sleepy Hollow Road

DateEvent & SourcePriceAppreciation
Jul 7, 2025

Closed (Public Record)

Public Record #1906800783

$1,900,000

+26.2% / yr

Aug 10, 2019

Closed (Public Record)

Public Record #1322303813

$481,250—
Aug 10, 2019

Closed (Public Record)

Public Record #651564456

$481,250—
DateEvent & SourcePrice
07/07/2025

Closed (Public Record)

Public Record #1906800783

$1,900,000

+26.2% / yr

08/10/2019

Closed (Public Record)

Public Record #1322303813

$481,250
08/10/2019

Closed (Public Record)

Public Record #651564456

$481,250

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 2 Sleepy Hollow Road

Taxable ValueLand$598,500Additions$509,250Total$1,107,750
Tax Record2024$18,488 ($1,541 / month)
Home Facts
Beds4Baths3Total Finished SqFt5,050 SqFtAbove Grade Finished SqFt5,050 SqFtUnfinished Basement SqFt2,769 SqFtStories2Lot Size114,127 SqFtStyleSingle Family ResidenceYear Built1981Zoning2ACCountyWESTERN CONNECTICUTAPNNCAN M:0039 B:101 L:00089Fireplace TypeHas Fireplace

Schools near 2 Sleepy Hollow Road

This home is within New Canaan School District.
Rating
School
Type
Grades
Distance
East School
Public - K to 4
Saxe Middle School
Public - 5 to 8
New Canaan High School
Public - 9 to 12
Rating
School
Distance
East School
PublicK to 4

Saxe Middle School
Public5 to 8

New Canaan High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

New Canaan
New Canaan
A verdant oasis filled with historic charm. Established in 1801, New Canaan shifted from agriculture to shoe making in the 19th century. As wealthy New Yorkers started to migrate to Connecticut, they initially made their way to New Canaan to build summer homes and eventually built permanent...
New Canaan Guide

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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Leslie Razook

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.