105 Sleepy Hollow Road
Ridgefield, Connecticut 06877
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,774
- Acres
- 1.20
- Year Built
- 2021
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
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.
Key Facts
- City/Town
- Ridgefield
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2021
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 2,774 sq ft
- Lot Size
- 1.20 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $19,196 / Annually
Market Snapshot
The Ridgefield Market
Single Family · trailing 12 months
Active Listings
50
40 under contract
Median List Price
$1.20M
50 active listings
Median Closed Price
$1.30M
235 sales
Median Days on Market
53
50 active listings
Median $ / Sq Ft
$437
50 active listings
Sale-to-List Ratio
101.8%
235 sales
How this home compares
List Price
$1.57M
vs $1.20M median
31.6% above median
Price / Sq Ft
$568
vs $437 median
30.0% above median
Days on Market
0 days
vs 53 days median
53 days fresher than median
Based on 50 active and 235 closed sales (trailing 12 mo) of single family in Ridgefield. Source: SmartMLS · As of September 3, 2026.
Location
105 Sleepy Hollow Road, Ridgefield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$8,097
- Property Taxes$1,600
- Insurance$525
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Ridgefield
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2021
- New Construction
- No/Resale
- Living Area
- 2,774 sq ft
Schools
- Elementary
- Scotland
- High
- Ridgefield
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Appliances
- Gas RangeWall OvenRange HoodRefrigeratorDishwasherWasherDryerWine Chiller
- Basement
- FullFull With Walk-Out
Exterior & Lot
- Lot Size
- 1.20 acres
- Zoning
- RAA
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Lightly WoodedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $19,196 / Annually
- Days on Market
- 0
- MLS #
- 24203399
- MLS Status
- Coming Soon
Similar Properties
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Co-Listed By
Stephanie Heering
Property Twins Real Estate
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/3/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/3/2026 at 3:02 AM UTC.