Ridgefield, CT / 14 DAYS ON MARKET

105 Sleepy Hollow RoadRidgefield, CT 06877

Asking price$1,475,000ActiveReduced $100,000 (6.3%) from original price · Price history ↓

Open house

  • Saturday, September 19, 202611:00 am – 1:00 pm ET
  • Sunday, September 20, 202612:00 pm – 2:00 pm ET

Our Take

105 Sleepy Hollow Road is a 2021 Ridgefield home with four bedrooms, three full bathrooms, and one half bath. Its main level brings the kitchen, gathering areas, and dining spaces together, while the kitchen includes a substantial center island and separate butler’s pantry. The second floor includes an owner’s suite with two walk-in closets and a finished bathroom with dual sinks, soaking tub, and glass-enclosed shower. Outdoor spaces include a deck, patio, and hot tub. A walk-out basement, generator, two-car garage, mudroom, laundry room, and walk-up attic add utility.

Estimated buyer rebate

Buy with Cress and Save $11,063 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

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*Estimate assumes a 2.5% buyer-agent commission and a 30% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24203399
Bedrooms
4
BathroomsBaths
3 full / 1 half
Square feet
2,774
Year built
2021
Acres
1.2
Property taxes
$19,196

July 2025-June 2026

What stands out

  • Kitchen with center island and butler’s pantry
  • Owner’s suite with two walk-in closets
  • Dual-sink bathroom with soaking tub and glass-enclosed shower
  • Unfinished walk-out basement with high ceilings
  • Deck, patio, and hot tub outdoors
  • Whole-house generator and two-car garage
  • Mudroom, separate laundry room, and walk-up attic
  • Gas fireplace near the gathering areas
Read the full listing 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.

Schools

Elementary
Scotland
Middle
Scotts Ridge
High
Ridgefield

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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105 Sleepy Hollow Road, Ridgefield, CT 06877

Price history

DateEventPrice
Latest asking price$1,475,000
Originally listed$1,575,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $1,475,000 asking price × assumed 2.5% buyer-agent commission × 30% rebate = $11,063. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by Property Twins Real Estate

Derek Heering

SmartMLS · Listing #24203399 · Active

Listing data checked: Sep 18, 2026, 7:05 AM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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