Newtown, CT / 6 DAYS ON MARKET

16 Winding Brook RoadNewtown, CT 06470

Asking price$2,200,000Active

Open house

  • Thursday, September 24, 20264:00 pm – 6:00 pm ET

Our Take

16 Winding Brook Road is a five-bedroom, four-and-a-half-bath home on 3.03 fenced acres at the end of a cul-de-sac, with a 100-acre land preserve as a natural backdrop. Inside, a two-story foyer, custom millwork, hardwood floors, remodeled bathrooms, and a remodeled kitchen with Wood Mode cabinetry, quartz countertops, and an oversized island shape the living spaces. French doors open the living room to a porcelain-tile patio. A gunite pool, pool house, vegetable garden, and finished walkout lower level with a game room, full bath, and sauna add outdoor and recreation spaces.

Estimated buyer rebate

Buy with Cress and Save $27,500 on brokerage fees*

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*Estimate assumes a 2.5% buyer-agent commission and a 50% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24205817
Bedrooms
5
BathroomsBaths
4 full / 1 half
Square feet
4,640
Year built
1986
Acres
3.03
Property taxes
$17,125

July 2025-June 2026

What stands out

  • Fenced acreage at a cul-de-sac’s end
  • 100-acre land preserve as a natural backdrop
  • Two-story foyer with custom millwork
  • Remodeled kitchen with Wood Mode cabinetry
  • Porcelain-tile patio with French-door access
  • Gunite pool and pool house
  • Raised stone beds for a vegetable garden
  • Walkout lower level with game room and sauna
Read the full listing 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 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.

Schools

Elementary
Middle Gate
Middle
Newtown
High
Newtown

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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16 Winding Brook Road, Newtown, CT 06470

Price history

DateEventPrice
Originally listed$2,200,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $2,200,000 asking price × assumed 2.5% buyer-agent commission × 50% rebate = $27,500. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by William Raveis Real Estate · (203) 426-3429

Connie Widmann

SmartMLS · Listing #24205817 · Active

Listing data checked: Sep 17, 2026, 7:06 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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