Wilton, CT / 3 DAYS ON MARKET

249 Chestnut Hill RoadWilton, CT 06897

Asking price$2,395,000Active

Our Take

249 Chestnut Hill Road is a South Wilton Colonial with Nantucket shingle-style architecture, a 2008 build, and a one-acre setting. The home pairs a chef’s kitchen with an adjoining family room, while the main level includes a room that can serve as a formal dining room or private workspace. The primary suite has a fireplace, sitting area, walk-in closets, and spa-inspired bath. Additional spaces include a multigenerational living area, lower-level play or game room, gym, and TV area.

Estimated buyer rebate

Buy with Cress and Save $29,938 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 #24206451
Bedrooms
5
BathroomsBaths
5 full / 2 half
Square feet
8,685
Year built
2008
Acres
1
Property taxes
$30,752

July 2026-June 2027

What stands out

  • Chef’s kitchen with Viking cooktop and double ovens
  • Family room with custom built-ins and fireplace
  • Primary suite with fireplace and sitting area
  • Main-level room for dining or private work
  • Three-zone integrated surround sound system
  • Upper-level multigenerational living space with built-ins
  • Lower-level play or game room, gym, and TV area
Read the full listing description

Sophisticated South Wilton Colonial: This Nantucket shingle-style residence blends timeless architectural elegance with seamless modern luxury, ideally positioned for effortless commuting to town, the train, and the Merritt Parkway. Thoughtfully designed for both grand entertaining and everyday comfort, the home features gorgeous custom details, extensive high-end upgrades, and an integrated three-zone surround sound system. The chef's kitchen is outfitted with premium appliances including a Viking six-burner gas cooktop, double ovens with a warming drawer, a built-in refrigerator, and a Miele dishwasher, opening directly into an inviting family room with custom built-ins and fireplace. On the main level, a sophisticated room provides versatile living space, seamlessly accommodating a formal dining room or private work space. Upstairs, the master bedroom serves as a luxurious private sanctuary with a cozy fireplace, a dedicated sitting area, expansive walk-in closets, and a spa-inspired primary bath. There are four additional bedrooms on this floor, two with ensuite bathrooms and two with a connected full-bath. The upper third level boasts a sixth bedroom suite and a large multi-generational living space with extensive built-ins, including cozy window-seating. The finished lower level provides an ideal versatile space featuring a spacious dedicated play/ game room, home gym, and a comfortable TV-watching area designed to grow right along with your kids...

Schools

Elementary
Miller-Driscoll
Middle
Not provided
High
Wilton

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

A closer look at the location

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249 Chestnut Hill Road, Wilton, CT 06897

Price history

DateEventPrice
Originally listed$2,395,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $2,395,000 asking price × assumed 2.5% buyer-agent commission × 50% rebate = $29,938. 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) 854-5116

Meghan Gatt

SmartMLS · Listing #24206451 · Active

Listing data checked: Sep 17, 2026, 7:11 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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