249 Chestnut Hill Road, Wilton, Connecticut

$2,395,000

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5

Beds

7

Baths

8,685

Square feet

1.00

Acre

About 249 Chestnut Hill Road

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...

Features of 249 Chestnut Hill Road

MLS® # 24206451
Price $2,395,000
Bedrooms 5
Bathrooms 7.00
Full Baths 5
Half Baths 2
Square Footage 8,685
Acres 1.00
Type Single Family For Sale
Style Colonial
Status Under Contract

Community Information

Address 249 Chestnut Hill Road
Area South Wilton
City Wilton
County Fairfield
State Connecticut
Zip Code 06897

Amenities

Parking Attached Garage
# of Garages 3
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Appliances Cook Top, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Air, Oil
Cooling Central Air
Fireplace Yes
# of Fireplaces 3
Has Basement Yes
Basement Full

Exterior

Exterior Shake
Exterior Features French Doors, Patio
Lot Description Fence - Stone, Level Lot
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Miller-Driscoll
High Wilton

Additional Information

Date Listed September 14th, 2026
Days on Market 17
Zoning R-2
RE / Bank Owned No

Listing Details

OfficeWilliam Raveis Real Estate

Listing Map

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Listing information last updated on October 6th, 2026 at 11:17pm EDT.