16 Winding Brook Road
Newtown, Connecticut 06470
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,640
- Acres
- 3.03
- Year Built
- 1986
- Property Type
- Single Family
Matt Caiola
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About This Home
Welcome to 16 Winding Brook, a distinguished custom estate offering an exceptional combination of craftsmanship, privacy and resort-style outdoor living. Built as the personal residence of a renowned builder and completely updated for today's lifestyle, the home is privately positioned on more than 3 fully fenced acres at the end of a desirable cul-de-sac, with a 100-acre land preserve creating an extraordinary natural backdrop. A two-story foyer introduces beautifully proportioned interiors enhanced by custom millwork, hardwood floors and abundant natural light. The elegant dining room is ideal for entertaining, while the front-to-back living room features a fireplace and French doors opening to an expansive porcelain-tile patio. The completely remodeled kitchen showcases Wood Mode cabinetry, quartz countertops and an oversized center island, flowing seamlessly into the inviting family room with a dramatic floor-to-ceiling fireplace. Bathroom have been beautifully remodeled, including the primary bath. Outdoors, the expansive level lawn is truly exceptional, providing a magnificent setting for the gunite pool and pool house, with generous space for entertaining, recreation and relaxed summer living. Raised stone beds create a beautiful vegetable garden area. The finished walkout lower level adds a game room, full bath and sauna. Minutes from the center of town, this remarkable estate offers a level of privacy, quality and outdoor living, difficult to replace.
Key Facts
- City/Town
- Newtown
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1986
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 4 full · 1 half
- Living Area
- 4,640 sq ft
- Lot Size
- 3.03 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $17,125 / Annually
Market Snapshot
The Newtown Market
Single Family · trailing 12 months
Active Listings
82
38 under contract
Median List Price
$880,000
82 active listings
Median Closed Price
$679,500
314 sales
Median Days on Market
35
82 active listings
Median $ / Sq Ft
$311
82 active listings
Sale-to-List Ratio
100.0%
314 sales
How this home compares
List Price
$2.20M
vs $880,000 median
2.5× the median
Price / Sq Ft
$474
vs $311 median
52.4% above median
Days on Market
0 days
vs 35 days median
35 days fresher than median
Based on 82 active and 314 closed sales (trailing 12 mo) of single family in Newtown. Source: SmartMLS · As of September 12, 2026.
Location
16 Winding Brook Road, Newtown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$11,427
- Property Taxes$1,427
- Insurance$733
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Newtown
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1986
- New Construction
- No/Resale
- Living Area
- 4,640 sq ft
- Below Grade
- 442 sq ft
Schools
- Elementary
- Middle Gate
- Middle
- Reed
- High
- Newtown
Interior
- Heating
- Hydro AirZoned
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry Location
- Main Floor in the Mud Room with Sink
- Appliances
- Gas CooktopWall OvenMicrowaveRefrigeratorDishwasherWasherDryerWine Chiller
- Basement
- PartialInterior AccessPartial With Walk-Out
- In-Law Apartment
- PossibleLower Level
- Interior Features
- Audio SystemAuto Garage Door OpenerCentral VacuumSaunaSecurity System
- Additional Rooms
- Mud RoomSteam/Sauna
Exterior & Lot
- Lot Size
- 3.03 acres
- Zoning
- R-3
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- GuniteHeatedPool HouseSpaSalt WaterIn Ground Pool
- Construction
- Clapboard
- Color
- Repose Gray
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedAwningsCabanaGarden AreaLightingStone WallFrench DoorsPatio
- Lot Description
- Fence - PartialBorders Open SpaceLevel LotOn Cul-De-SacProfessionally Landscaped
Listing & Financials
- Property Taxes
- $17,125 / Annually
- Days on Market
- 0
- MLS #
- 24205817
- MLS Status
- Active
- Financing
- FHA,VA,CHFA
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/12/2026. 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 9/12/2026 at 2:15 AM UTC.