249 Chestnut Hill Rd Wilton, CT, 06897

single family home
$ 2,395,000 For Sale Active Sep 14, 2026
  • 5 beds
  • 7 baths
  • 8,685 sq ft
  • 1 acre
  • 2008 year built
  • 3 cars garage
Open House
249 Chestnut Hill Road, Wilton, CT 06897 | For Sale at $2,395,000
40 photos
 Map of 249 Chestnut Hill Road, Wilton, CT 06897 single family home

About the Home

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...

Rooms & Interior

5 bedrooms beds
5 full + 2 half baths
8,685 square feet sq ft

Room Details

  • Great Room (Upper Level) Book Shelves, Built-Ins, Wall/Wall Carpet, Hardwood Floor, On 3rd Floor
  • Bedroom (Upper Level) 9 ft+ Ceilings, Built-Ins, Jack & Jill Bath, Walk-In Closet, Hardwood Floor
  • Family Room (Main Level) 9 ft+ Ceilings, Book Shelves, Built-Ins, Fireplace, Hardwood Floor
  • Primary Br Suite (Upper Level) Vaulted Ceiling, Built-Ins, Dressing Room, Fireplace, Full Bath, Walk-In Closet
  • Bedroom (Upper Level) 9 ft+ Ceilings, Built-Ins, Full Bath, Walk-In Closet, Hardwood Floor
  • Rec/Play Room (Lower Level) Built-Ins
  • Dining Room (Main Level) 9 ft+ Ceilings, Hardwood Floor
  • Library (Main Level) 9 ft+ Ceilings, Built-Ins, Hardwood Floor
  • Bedroom (Upper Level) 9 ft+ Ceilings, Full Bath, Walk-In Closet, Hardwood Floor
  • Other (Upper Level) Full Bath
  • Bedroom (Upper Level) 9 ft+ Ceilings, Built-Ins, Jack & Jill Bath, Walk-In Closet, Hardwood Floor
  • Living Room (Main Level) 9 ft+ Ceilings, Fireplace, Hardwood Floor
  • Kitchen (Main Level) 9 ft+ Ceilings, Built-Ins, Granite Counters, Dining Area, Island, Hardwood Floor
  • Other Rooms Foyer, Gym, Laundry room, Mud room, Sitting room, Workshop

Home Features

Heating

  • Fireplaces: 3
  • Heating: hot air
  • Heat fuel type: oil
  • Fuel tank: in basement

Cooling

  • Central air

Appliances

  • Cook top
  • Wall oven
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer

Basement

  • Full

Laundry

  • Upper level

Exterior Features

  • French doors
  • Patio

Property Details

Parking

  • Garage spaces: 3
  • Attached garage

Lot Details

  • Lot surface: 1 acres
  • Fence - stone
  • Level lot

Utilities

  • Water: private well
  • Sewage: septic

Construction Details

Style
colonial
Construction year
2008
Exterior Siding
shake
Foundation
concrete
Roof
asphalt shingle

Open Houses

There is 1 scheduled open house for 249 Chestnut Hill Road, Wilton, CT.
September 15, 2026 Sep 15, 2026 11:00 - 13:00 (broker)

Area & Town

This home is located in South Wilton neighborhood, in the town of Wilton.

Wilton Connecticut

Natural beauty, great community, best education

  • $1.35M med. price
  • 45 homes for sale

Finance & Listing Info

Status Active
Listing date September 14, 2026
List price $ 2,395,000
Current price $ 2,395,000
Tax amount $ 30,752
Tax year july 2026-june 2027
MLS ID #24206451
List Agent Meghan Gatt
Co-List Agent Carla Kupiec
List Office William Raveis Real Estate
Co-List Office william raveis real estate
(c) 2026 Based on information provided to and compiled by the Smart MLS, Inc.

249 Chestnut Hill Road Home Photos

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