16 Winding Brook Road

Beautiful twilight exterior with manicured landscaping.
Aerial view showcasing the home, expansive grounds, circular driveway, pool area and surrounding mature trees.
Beautifully landscaped grounds with evening lighting.
Welcoming two-story foyer featuring a curved staircase and distinctive black-and-white flooring.
Formal dining room with hardwood flooring, detailed millwork, crown molding and elegant chandelier.
Spacious formal living room featuring hardwood flooring, fireplace, crown molding and multiple windows overlooking the grounds.
Additional view of the formal living room with fireplace, hardwood flooring and French doors providing direct access to the patio.
Inviting family room with hardwood flooring, brick fireplace and dramatic arched windows overlooking the property.
Additional view of the family room showcasing built-in shelving, hardwood flooring and abundant natural light.
Updated kitchen featuring abundant cabinetry, expansive counter space, recessed lighting and views of the surrounding greenery.
Updated kitchen with extensive cabinetry, stainless steel appliances, decorative backsplash and generous workspace.
Bright eat-in kitchen featuring a large center island, skylights, walls of windows and access to the outdoor living areas.
Spacious hallway with tile flooring, recessed lighting and convenient access to the back staircase.
Main-level powder room featuring a pedestal sink and classic black-and-white flooring.
Bright and inviting main level bedroom featuring hardwood floors, crown molding and double windows overlooking the surrounding greenery.
Beautifully updated full bath featuring a glass-enclosed tiled shower with steam, custom vanity and modern fixtures.
Generously sized primary bedroom featuring hardwood floors, charming window seats and abundant natural light.
Spacious primary suite offering plenty of room for additional furniture and convenient access to the en-suite bath.
Stunning renovated primary bath featuring a spacious glass-enclosed shower, patterned tile, skylight and custom built-in bench seating.
Light-filled primary bath with custom cabinetry, marble-look countertops, oversized shower and thoughtful built-in storage.
Comfortable bedroom featuring hardwood floors, built-in window seating and generous closet space.
Updated full bath with double vanity and tiled tub/shower.
Bright bedroom with a large double window and ample space for a desk, making it equally well suited for a bedroom or study area.
Spacious bedroom with soft carpeting, double windows and flexible space for multiple beds or additional furnishings.
Spacious bonus room with skylights and flexible living space.
Finished lower-level recreation room with pool table.
Lower-level full bath with glass-enclosed shower and Sauna
Spacious stone patio surrounded by mature trees and overlooking the beautifully landscaped backyard.
Private backyard patio with multiple seating areas and views of the lush, professionally landscaped grounds.
Inviting outdoor patio overlooking the backyard.
Spacious rear patio with retractable awning, multiple seating areas and beautiful hydrangea plantings.
Expansive outdoor patio offering multiple areas for dining, grilling and entertaining.
Resort-style pool surrounded by lush landscaping.
In-ground pool surrounded by mature landscaping, stonework and a spacious poolside lounging area.
Private backyard retreat featuring an in-ground pool, spa, stone surround and lush established gardens.
Aerial view of the private pool and spa surrounded by extensive landscaping, stonework and a pool house.
Beautifully landscaped pool area featuring colorful perennial gardens and a charming pool house.
Pool house with kitchenette and breakfast bar seating.
Front exterior showcasing the home's classic architecture, expansive lawn and mature landscaping.
Active
$2,200,000
5 beds4,640 sqft$474/sqft
16 Winding Brook Rd, Newtown, CT 06470
Est: $12,796/moGet pre-approved
Single FamilyProperty Type
3.03 acresLot Size
1986Year Built
$474/sq ftPrice per sq ft
2 carsParking Spaces

Description

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...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.
Days on Market Listed Today
  • Listed by: Connie Widmann 203.856.6491 connie.widmann@raveis.com • William Raveis Real Estate
Last updated: 09/11/2026 08:58 PM • Source: SMARTMLS, MLS#: 24205817

Location

Listing Courtesy of William Raveis Real Estate, Connie Widmann
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Property Taxes

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Property Information for 16 Winding Brook Road

Property Details
  • Taxes: $17,125 / year
  • MLS Type: Residential
  • County: Fairfield County
  • Basement Description: Partial, Interior Access, Partial With Walk-Out
  • Direct Waterfront: No
  • Garages Number: 2
  • Style: Cape Cod
  • Garage Parking Info: Attached Garage
  • Swimming Pool: Yes
Building Information
  • Year Built: 1986
  • Lot Size: 3.03 AC / 131,986 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Brushy Hill to John Beach, Winding Brook is first Right, at the end of the Cul De Sac on the right.
  • Elementary School: Middle Gate
  • Flood Zone: No
  • High School: Newtown
  • Intermediate School: Reed
  • Latitude: 41.375053
  • Longitude: -73.298605
  • Middle Jr High School: Newtown
  • Neighborhood Amenities: Basketball Court, Golf Course, Health Club, Lake, Library, Medical Facilities, Public Pool, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $17,125
Interior and Exterior Features
Exterior Features
  • Exterior Features: Shed, Awnings, Cabana, Garden Area, Lighting, Stone Wall, French Doors, Patio
  • Pool Description: Gunite, Heated, Pool House, Spa, Salt Water, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Cooktop, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Unfinished, Storage Space, Walk-In
  • Cooling System: Central Air
  • Heat Type: Hydro Air, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Home Automation: Built In Audio, Lighting, Security System
  • Interior Features: Audio System, Auto Garage Door Opener, Central Vacuum, Sauna, Security System
  • Laundry Room Location: Main Floor in the Mud Room with Sink
  • Rooms Additional: Mud Room, Steam/Sauna
  • Rooms Total: 11
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,French Doors,Patio/Terrace,Hardwood Floor
  • Room Length: 17.1
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 27.6
Room 2
  • Room Entry Order: 10
  • Room Features: Hardwood Floor
  • Room Length: 12.1
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.1
Room 3
  • Room Entry Order: 11
  • Room Features: Skylight,Vaulted Ceiling,Hardwood Floor
  • Room Length: 20.8
  • Room Level: Upper
  • Room Type: Office
  • Room Width: 27.6
Room 4
  • Room Entry Order: 12
  • Room Features: Full Bath,Steam/Sauna,Sliders,Wall/Wall Carpet
  • Room Length: 17.1
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 27.6
Room 5
  • Listing Key: 5B11587F82B03E82E063E201100A48CE
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 16.4
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 13.9
Room 6
  • Room Entry Order: 3
  • Room Features: Vaulted Ceiling,Breakfast Bar,Quartz Counters,Dining Area,Patio/Terrace,Tile Floor
  • Room Length: 21.9
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 13.5
Room 7
  • Room Entry Order: 4
  • Room Features: Vaulted Ceiling,Built-Ins,Wood Stove,French Doors,Patio/Terrace,Hardwood Floor
  • Room Length: 16.5
  • Room Level: Main
  • Room Type: Great Room
  • Room Width: 20.0
Room 8
  • Room Entry Order: 5
  • Room Features: Full Bath,Hardwood Floor,Stall Shower
  • Room Length: 13.7
  • Room Level: Main
  • Room Type: Bedroom
  • Room Width: 12.0
Room 9
  • Listing Key: 5B11587F82B03E82E063E201100A48CE
  • Room Entry Order: 6
  • Room Features: Full Bath,Stall Shower,Steam/Sauna,Walk-In Closet,Hardwood Floor
  • Room Length: 21.6
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 29.2
Room 10
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Length: 13.9
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.5
Room 11
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Length: 16.4
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.7
Room 12
  • Room Entry Order: 9
  • Room Features: Tub w/Shower,Tile Floor
  • Room Length: 7.1
  • Room Level: Upper
  • Room Type: Full Bath
  • Room Width: 8.7
Property
Property and Assessments
  • Color: Repose Gray
  • Construction Description: Frame, Concrete
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1986
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level
  • In Law Apartment: Possible
  • Sq Ft Est Heated Below Grade: 442
  • Living Area SQFT Per Public Records: 4198
Lot Information
  • Lot Description: Fence - Partial, Borders Open Space, Level Lot, On Cul-De-Sac, Professionally Landscaped
  • Parcel Number: 207100
  • Sq Ft Est Heated Above Grade: 4198.0
  • Sq Ft Total: 4640.0
  • Zoning: R-3
Utilities
  • Energy Features: Generator Ready, Ridge Vents, Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, 50 Gallon Tank
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 16 Winding Brook Road

DateEvent & SourcePriceAppreciation
May 19, 2006

Closed (Public Record)

Public Record #197356159

$967,000—
DateEvent & SourcePrice
05/19/2006

Closed (Public Record)

Public Record #197356159

$967,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 16 Winding Brook Road

Taxable ValueLand$146,700Additions$449,150Total$595,850
Tax Record2025$17,125 ($1,427 / month)
Home Facts
Beds4Baths4.5Total Finished SqFt4,198 SqFtAbove Grade Finished SqFt4,198 SqFtUnfinished Basement SqFt442 SqFtStories2Lot Size131,987 SqFtStyleSingle Family ResidenceYear Built1986Year Renovated1986ZoningR-3CountyWESTERN CONNECTICUTAPNNTWN M:31 B:9 L:39 U:8

Schools near 16 Winding Brook Road

This home is within Newtown School District.
Rating
School
Type
Grades
Distance
Middle Gate Elementary School
Public - K to 4
Reed Intermediate School
Public - 5 to 6
Newtown Middle School
Public - 7 to 8
Newtown High School
Public - 9 to 12
Rating
School
Distance
Middle Gate Elementary School
PublicK to 4

Reed Intermediate School
Public5 to 6

Newtown Middle School
Public7 to 8

Newtown High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 16 Winding Brook Road, Newtown, CT 06470

16 Winding Brook Road is a single family home for sale in Newtown, CT 06470. This listing's school district is Newtown School District. Nearby schools include Middle Gate Elementary School, Reed Intermediate School and Newtown Middle School. 16 Winding Brook Road is a 5-bed, 5-bath, 4,640 sqft single family home built in 1986.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Raveis Real Estate, Connie Widmann

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.