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249 Chestnut Hill Road, Wilton, CT 06897

Single Family For Sale

$2,395,000
$276/sqft
249 Chestnut Hill Road, Wilton, CT
Active
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5
Bedrooms
7
Bathrooms
8,685
Sq Ft
1
Acres
2008
Year Built

About This 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...

Listed by Meghan Gatt (203) 904-8064 with William Raveis Real Estate (203) 854-5116

Listing Snapshot

Price $2,395,000 Days on Our Site 1 days
Property Tax $30,752/yr Style Colonial
Year Built 2008 Total Sq Ft 8,685
Lot Size 1 acres HOA Fees N/A
Bedrooms 5 Full Bathrooms 5
Total Rooms 11 Half Baths 2

Key Features

Appliances
  • Cook Top
  • Wall Oven
  • Refrigerator
  • Dishwasher
  • Washer
  • Dryer
Outdoor
  • French Doors
  • Patio

Structure & Parking

Construction Frame
Roof Asphalt Shingle
Garage Spaces 3
Garage Type Attached Garage
Below Grade 2,305 sq ft

Systems & Utilities

Heat Hot Air
Fuel Oil
Cooling Central Air
Hot Water Oil, Domestic
Water Private Well
Sewer Septic

Schools

Elem Miller-Driscoll
High Wilton

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Property Tax $2,563/mo
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Sep 14, 2026 Listed $2,395,000

Frequently Asked Questions

How much does 249 Chestnut Hill Road in Wilton, CT cost?
This property is listed at $2,395,000, which works out to $276 per square foot.
How many bedrooms does 249 Chestnut Hill Road have?
This home has 5 bedrooms and 7 bathrooms.
What is the square footage of 249 Chestnut Hill Road?
The home is 8,685 square feet, situated on 1 acres.
When was 249 Chestnut Hill Road in Wilton built?
This property was built in 2008.
Is 249 Chestnut Hill Road, Wilton, CT still available?
The current MLS status of this property is "Active". Contact RYZE Realty Group for the latest availability.
What school district is 249 Chestnut Hill Road, Wilton in?
This home is served by the Wilton public school system, with Miller-Driscoll as the elementary school and Wilton as the high school.
How do I schedule a tour of 249 Chestnut Hill Road, Wilton, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Meghan Gatt · (203) 904-8064

William Raveis Real Estate · (203) 854-5116

MLS# 24206451 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Sep 15, 2026 11:27 PM UTC