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105 Sleepy Hollow Road

Ridgefield, Connecticut 06877

COMING SOON - NEW$1,575,000
Beds
4
Baths
3 | 1
SqFt
2,774
Acres
1.20
Year Built
2021
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$10,222

per 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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Listed By

Derek Heering

(203) 832-7677

Property Twins Real Estate

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.