Active Under Contract
Price CutPrice Drop: $100K (10/08)
Single family home for sale at 105 Sleepy Holw Rd, Ridgefield, CT 06877 | MLS# 24203399 | Listing updated on 2026-10-29
Photo 1 of Single family home for sale at 105 Sleepy Holw Rd, Ridgefield, CT 06877 | MLS# 24203399 | Listing updated on 2026-10-29
Photo 2 of Single family home for sale at 105 Sleepy Holw Rd, Ridgefield, CT 06877 | MLS# 24203399 | Listing updated on 2026-10-29
Photo 3 of Single family home for sale at 105 Sleepy Holw Rd, Ridgefield, CT 06877 | MLS# 24203399 | Listing updated on 2026-10-29
Photo 4 of Single family home for sale at 105 Sleepy Holw Rd, Ridgefield, CT 06877 | MLS# 24203399 | Listing updated on 2026-10-29
36+
Beds Icon

Street View

$1,475,000

Monthly Est:$7,342

  • Beds Icon4 Beds
  • Beds Icon
    4 Baths
  • Beds Icon2,774sqft

105 Sleepy Holw Rd, Ridgefield, CT 06877

$7,342/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 2021

  • $-- HOA

  • 1.2 acres lot

  • $532/sq.ft

Description

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.

  • Houzeo last checked: 27 minutes ago
  • Listing updated: October 29, 2026 at 4:50 am
  • Listing Provided by: Derek Heering | Property Twins Real Estate
  • Source: SMART MLS-CT | MLS#: 24203399 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Fairfield County

  • City

    Ridgefield

  • Neighborhood

    --

  • Year Built

    2021

  • HOA Fees

    -

  • Finished Area

    2,774 sqft

  • Lot Size

    1.2 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24203399

  • MLS Status

    Under Contract

  • Days on Market

    56

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 4

Interior

  • Heating

    Propane

  • Sewer

    Septic

  • Cooling

    Central Air

  • Appliances

    Gas Range, Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller

Construction

  • Year Built

    Year Built: 2021

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial

  • Roof

    Asphalt Shingle

  • Foundation Details

    Concrete

Utilities & Energy

  • Basement

    Full, Full With Walk Out

  • Water Source

    Private Well

  • Parking Features

    Attached Garage

Other Features

  • Lot Features

    Lightly Wooded, Professionally Landscaped

  • Subdivision Name

    N/a

Price History

DateEventPrice

09/14/2026

Source: mls_logoSMART MLS-CT #24203399

Contingent (Active Under Contract)

$1,475,000 -6.35%

$532/sqft

09/04/2026

Source: mls_logoSMART MLS-CT #24203399

Listed for Sale

$1,575,000

$568/sqft

09/02/2026

Source: mls_logoSMART MLS-CT #24203399

Coming Soon

$1,575,000 +16053.85%

$568/sqft

01/09/2025

Source: #24063938

Price Decreased

$9,750 -44.29%

$4/sqft

07/30/2024

Source: mls_logoSMART MLS-CT #24013908

Sold

$17,500

$6/sqft

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 29, 2026, 01:30PM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

Skip to Main Content