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105 Sleepy Hollow RoadRidgefield, CT 06877

For Sale

$1,475,000

Smart Buyer Rebate $14,750

Privacy, craftsmanship, and a nearly new home come together at 105 Sleepy Hollow Road. Constructed in 2021, this distinctive Ridgefield residence offers generous proportions and a polished interior filled with sunlight. The main level was created with connection in mind, bringing the kitchen, gathering areas, and dining spaces together naturally. A substantial center island anchors the kitchen, complemented by extensive prep space and a separate butler's pantry. Nearby, a gas fireplace adds warmth and character. The second floor includes four bedrooms, highlighted by an impressive owner's suite with two walk-in closets and a beautifully finished bathroom with dual sinks, a freestanding soaking tub, and large glass-enclosed shower. Two additional full bathrooms serve the remaining bedrooms. Below, a large unfinished walk-out basement with high ceilings provides exciting possibilities for future finished space, whether envisioned as a gym, media room, recreation area, or additional living space. The property offers multiple outdoor areas, including a deck, patio, and hot tub, all surrounded by established landscaping and a peaceful natural backdrop. A whole-house generator, 2-car garage, mudroom, separate laundry room, and walk-up attic add everyday practicality. Close to Ridgefield's town center and commuter routes, this special property pairs a newer build with space, seclusion, and convenience.

Listed by Derek Heering

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Property Twins Real Estate

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(203) 832-7677

Listed by Stephanie Heering

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Property Twins Real Estate

Last updated September 14, 2026

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Source: SmartMLS #24203399

Listing Facts

  • TypeSingle-family
  • NeighborhoodFairfield County
  • Bedrooms4
  • Bathrooms4
  • Days on Prevu13
  • Taxes$19,196/year
  • Size2,774 sqft
  • Price per sqft$532

Location

Mortgage Calculator

Listing History

09/15/2026
Price Decreased
$1,475,000
09/04/2026
Status changed to Active
$1,575,000
09/02/2026
Listed by Property Twins Real Estate
$1,575,000
  1. 09/15/2026$1,475,000
    Price Decreased
  2. 09/04/2026$1,575,000
    Status changed to Active
  3. 09/02/2026$1,575,000
    Listed by Property Twins Real Estate

Property Details for 105 Sleepy Hollow Road

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2021
  • Year Built Details: Public Records
  • Architectural Style: Colonial
  • Construction Materials: Frame

Features

  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Lightly Wooded, Professionally Landscaped
  • Lot Size Acres: 1.20

Financial

Taxes

  • Parcel Number: 273420
  • Tax Annual Amount: $19,196.00
  • Tax Year: 25

Interior

Features

  • Appliances: Gas Range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
  • Fireplaces Total: 1

Measurements

  • Living Area: 2,774

Rooms

  • Basement: Full, Full With Walk-Out
  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 4
  • Bedrooms Total: 4
  • Rooms Total: 8

Parking

Parking

  • Attached Garage: Attached Garage
  • Garage Spaces: 2

Schools

Elementary School

  • Elementary School: Scotland

High School

  • High School: Ridgefield

Middle or Junior School

  • Middle Or Junior School: Scotts Ridge

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Hot Air
  • Sewer: Septic
  • Water Source: Private Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 4 bedrooms and 4 bathrooms in this single-family home at 105 Sleepy Hollow Road.

What schools are nearby to 105 Sleepy Hollow Road?

Nearby schools include the Scotland Elementary School, Scotts Ridge Middle School, and Ridgefield High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 105 Sleepy Hollow Road.

What are the annual taxes for 105 Sleepy Hollow Road?

Annual taxes for this single-family home are estimated at $19,196.

How does 105 Sleepy Hollow Road compare to other single-family homes in Fairfield County?

This single-family home is listed 39% below the average price for single-family homes in Fairfield County and has been on the market for 44 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 2,774 sqft.

105 Sleepy Hollow Road is a 4-bedroom, 4-bath single-family home for sale in Ridgefield CT 06877. Available on Prevu for 13 days at $1,475,000. This includes a recent price decrease of $100,000. This property features 2,774 square feet of living space, located in Fairfield County. The median listing price for single-family homes in this area is $815,000. Nearby schools include Scotland Elementary School, Scotts Ridge Middle School, and Ridgefield High School. Explore more single-family home listings in Connecticut.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.