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
| Office | William Raveis Real Estate |
|---|
