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Back 2 Sleepy Hollow Rd
Off Market

2 Sleepy Hollow Rd

Fairfield County CT 06840

5
3
3
5658 sq. ft.
2.62 ac.
Single-Family
Last sold for $2,400,000
Leslie RazookLeslie Razook, last sold this property on 29 June 2026 after 46 days on market.

Overview

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.

Features

5 bedrooms
3 bathrooms
3 carspaces
3 garage spaces
5658 sq. ft. floor area
2.62 ac. lot size
Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Fairfield County over the last 12 months, the estimated median property value of 2 Sleepy Hollow Rd is $3m.

Median value
$3m
Estimated value range
$955k - $8.65m
Median days on market
21
Estimated value trend
7%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Fairfield County. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 2 Sleepy Hollow Rd

2026
Sold
$2,400,000
29 Jun 2026 by Leslie Razook, of William Pitt Sotheby's Int'l
2025
Sold
$1,900,000
07 Jul 2025 by Richard Tanner, of Houlihan Lawrence
2019
Sold
$962,500
20 Aug 2019 by Martha Perry, of William Pitt Sotheby's Int'l

Happy sellers in Fairfield County

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We have insufficient information to provide an overview of customer satisfaction for Fairfield County. Viewing the agent profiles, reviews and sales for Fairfield County can provide insights for this location.

Local market activity for 5 bedroom single-family properties in Fairfield County

In the last 12 months, 75 five-bedroom single-family properties similar to 2 Sleepy Hollow Rd, have been sold.

This represents a 11% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Fairfield County

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Hannelore Kaplan

Hannelore Kaplan is a recommended agent for Fairfield County.  They have 22 local sales across the last 12 months.

  •   5   (1 review)
  •  22 Sales in Fairfield County
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Christine Saxe

Christine Saxe is a recommended agent for Fairfield County.  They have 15 local sales across the last 12 months.

  •  15 Sales in Fairfield County
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Marsha Charles

Marsha Charles is a recommended agent for Fairfield County.  They have 10 local sales across the last 12 months.

  •  10 Sales in Fairfield County
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Amanda Bryan

Amanda Bryan is a recommended agent for Fairfield County.  They have 7 local sales across the last 12 months.

  •  7 Sales in Fairfield County
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