21 School Road
Wilton, Connecticut 06897
- Beds
- 6
- Baths
- 5 | 2
- SqFt
- 7,793
- Acres
- 4.35
- Year Built
- 1966
- 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
Welcome to an unparalleled masterpiece of living, nestled within a completely fenced, four-plus-acre private paradise in the very heart of Wilton, Connecticut. This extraordinary estate perfectly balances absolute serene privacy with the effortless convenience of town life. Approached via double-gated entries, the winding driveway unveils a residence meticulously crafted for the epicurean, the entertainer, and the modern visionary. The heart of the home centers around a true chef's kitchen, anchored by a roaring fireplace that radiates warmth and timeless character. Designed for both casual mornings and grand-scale catering, it features premium commercial appliances, a designated coffee bar room for your morning rituals, and endless custom storage to keep the aesthetic flawless. Just off the kitchen, a walk-in wine room awaits your private collection. For seamless entertaining, the formal sitting room features a fully equipped walk-in bar, transitioning beautifully into a stunning screened-in porch and a massive outside deck overlooking the grounds. Offering a total of six luxurious bedrooms, the home's layout is brilliantly engineered for ultimate privacy. The Owner's Suite and Family Quarters are situated in the main expanse of the home, offering opulent retreats with peaceful views of the estate.
Key Facts
- City/Town
- Wilton
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1966
- Days on Market
- 0 days
- Beds
- 6
- Baths
- 5 full · 2 half
- Living Area
- 7,793 sq ft
- Lot Size
- 4.35 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $50,521 / Annually
Market Snapshot
The Wilton Market
Single Family · trailing 12 months
Active Listings
32
24 under contract
Median List Price
$1.80M
32 active listings
Median Closed Price
$1.41M
208 sales
Median Days on Market
29
32 active listings
Median $ / Sq Ft
$424
32 active listings
Sale-to-List Ratio
105.8%
208 sales
How this home compares
List Price
$4.00M
vs $1.80M median
2.2× the median
Price / Sq Ft
$513
vs $424 median
21.0% above median
Days on Market
0 days
vs 29 days median
29 days fresher than median
Based on 32 active and 208 closed sales (trailing 12 mo) of single family in Wilton. Source: SmartMLS · As of October 7, 2026.
Location
21 School Road, Wilton, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per month
- Principal & Interest$21,895
- Property Taxes$4,210
- Insurance$1,333
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Wilton
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1966
- New Construction
- No/Resale
- Living Area
- 7,793 sq ft
- Below Grade
- 1,492 sq ft
Schools
- Elementary
- Miller-Driscoll
- Middle
- Cider Mill
- High
- Wilton
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 4
- Laundry Location
- Main Level
- Appliances
- Gas CooktopWall OvenRange HoodSubzeroDishwasherWasherDryerWine Chiller
- Basement
- FullFull With Walk-Out
- Interior Features
- Audio SystemAuto Garage Door OpenerCable - AvailableSecurity System
- Additional Rooms
- GymLaundry RoomMud Room
Exterior & Lot
- Lot Size
- 4.35 acres
- Zoning
- R-2
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedSpaSalt WaterIn Ground Pool
- Construction
- Wood
- Color
- White
- Roof
- Wood Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-ScreenedWrap Around DeckBarnLightingFrench DoorsGrillPorchDeckGarden AreaUnderground Sprinkler
- Lot Description
- Fence - FullLevel LotSloping Lot
Listing & Financials
- Property Taxes
- $50,521 / Annually
- Days on Market
- 0
- MLS #
- 24212467
- MLS Status
- Coming Soon
Similar Properties
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Co-Listed By
Lainie Floyd
William Pitt Sotheby's Int'l
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/7/2026. 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 10/7/2026 at 5:46 AM UTC.