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$2,195,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 5,658 Sq. Ft.
  • 3 Car Garage
  • Updated 2 days ago

Next open house:

Open House: 1:00 PM - 3:00 PM

Sunday 5/17 1:00 PM - 3:00 PM

2 Sleepy Hollow Road,New Canaan, CT 06840

2 Sleepy Hollow RoadNew CanaanCT06840

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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.

Full Property Details for 2 Sleepy Hollow Rd

General

  • Price: $2,195,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24166322
  • Updated: 5/14/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 12
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Electric Cooktop, Wall Oven, Refrigerator, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Balcony/Deck, Full Bath, Walk-In Closet, Main
  • Bedroom 1: Bedroom - Built-Ins, Full Bath, Main
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper
  • Bedroom 4: Bedroom, Upper

Other Rooms

  • Living Room: Living Room - 2 Story Window(s), Vaulted Ceiling, Balcony/Deck, Gas Log Fireplace, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - 2 Story Window(s), 9 ft+ Ceilings, Built-Ins, Pantry, Hardwood, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Balcony/Deck, Built-Ins, Gas Log Fireplace, Patio/Terrace, Main
  • Office: Office, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Sliders, Lower
  • Rec Room: Sliders, Lower
  • Theater/Media: Media Room - Vaulted Ceiling, Beams, Built-Ins, Upper
  • Laundry: Main Level

Exterior

  • Exterior Features: Deck, Garden Area

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage, Under House Garage

Location

  • County: Fairfield
  • Driving Directions: Laurel Rd to Sleepy Hollow

School Information

  • Elementary School: East
  • Middle School: Saxe Middle
  • High School: New Canaan

Heating & Cooling

  • Cooling Type: Central Air, Split System
  • Heating Type: Hot Air, Propane
  • Heating Fuel: Propane
  • Water Heater: Electric, Propane, Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Contemporary, Modern
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Heated, Partially Finished, Walk-out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 5,658
  • Above Ground: 5,050 Sq. Ft.
  • Below Ground: 608 Sq. Ft.
  • Year Built: 1981

Lot Features

  • Lot Size (Acres): 2.62
  • Zoning: 2AC
  • Lot Description: Some Wetlands, Level Lot, On Cul-De-Sac, Professionally Landscaped, Rolling

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Pond, View

Financial Considerations

  • Assessment Amount: $1,107,750
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: see inclusion/ exclusion sheet
  • Flood Zone: Yes
  • Property ID: 187541

Listed by William Pitt Sotheby's Int'l, Leslie Razook

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Listing agent

— 2 Sleepy Hollow Rd —

  • Leslie Razook

    William Pitt Sotheby's Int'l

Agent Contact: (203) 918-4452 Office Contact: (203) 966-2633

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2 Sleepy Hollow Rd

School District:New Canaan School District
NameGradesDistance
East School
54 Little Brook Road, New Canaan, CT 06840
K-41.8 mi
Saxe Middle School
468 South Avenue, New Canaan, CT 06840
5-82.8 mi
New Canaan High School
11 Farm Road, New Canaan, CT 06840
9-123 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2 Sleepy Hollow Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/14/2026
Listed
$2,195,000
15.53%
MLS
7/07/2025
Sold
$1,900,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2 Sleepy Hollow Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$18,488
3%
$1,107,750
—
2023
$17,879
7%
$1,107,750
26%
2023
$16,664
3%
$879,830
—
2022
$16,162
1%
$879,830
—
2021
$15,978
—
$879,830
—
2020
$15,978
—
$879,830
—
2019
$16,048
6%
$879,830
-2%
2018
$15,169
2%
$894,390
—
2017
$14,909
—
$894,390
-2%
2016
$14,860
2%
$911,120
—
2015
$14,569
3%
$911,120
—
2014
$14,159
-24%
$911,120
-29%
2012
$18,597
—
$1,274,630
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by William Pitt Sotheby's Int'l, Leslie Razook

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2 Sleepy Hollow Road, New Canaan, CT 06840 (MLS# 24166322) is a Single Family property with 5 bedrooms and 3 full bathrooms. 2 Sleepy Hollow Road is currently listed for $2,195,000 and was received on May 14, 2026. Want to learn more about 2 Sleepy Hollow Road? Do you have questions about finding other Single Family real estate for sale in New Canaan? You can browse all New Canaan real estate or contact a Coldwell Banker agent to request more information.

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