George Cress of Real Broker Email: george@cress.co (dot co) Call/Text: 212-203-5251
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.
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
Open Google Maps ↗105 Sleepy Hollow Road, Ridgefield, CT 06877
Price history
| Date | Event | Price |
|---|---|---|
| Latest asking price | $1,475,000 | |
| Originally listed | $1,575,000 |
Intermediate price changes and previous listings may not be included.
Could this be your next home?
Let’s talk about the property—and what working with Cress could save you.
*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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