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249 Chestnut Hill Road

Wilton, Connecticut 06897

ACTIVE - NEW$2,395,000
Beds
5
Baths
5 | 2
SqFt
8,685
Acres
1.00
Year Built
2008
Matt Caiola

Matt Caiola

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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...

Key Facts

City/Town
Wilton
Neighborhood
South Wilton
Property / Style
Single Family · Colonial
Year Built
2008
Days on Market
0 days
Beds
5
Baths
5 full · 2 half
Living Area
8,685 sq ft
Lot Size
1.00 acres
Garage / Parking
3 garage
Property Taxes
$30,752 / Annually

Market Snapshot

The Wilton Market

Single Family · trailing 12 months

View area

Median Days on Market

45

29 active listings

Median $ / Sq Ft

$414

29 active listings

Sale-to-List Ratio

105.5%

213 sales

How this home compares

List Price

$2.40M

vs $1.79M median

33.4% above median

Price / Sq Ft

$276

vs $414 median

33.3% below median

Days on Market

0 days

vs 45 days median

45 days fresher than median

Based on 29 active and 213 closed sales (trailing 12 mo) of single family in Wilton. Source: SmartMLS · As of September 14, 2026.

Location

249 Chestnut Hill Road, Wilton, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$15,801

per month

  • Principal & Interest$12,440
  • Property Taxes$2,563
  • Insurance$798
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Wilton
Neighborhood
South Wilton
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
2008
New Construction
No/Resale
Living Area
8,685 sq ft
Below Grade
2,305 sq ft

Schools

Elementary
Miller-Driscoll
High
Wilton

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
3
Laundry
Upper Level
Appliances
Cook TopWall OvenRefrigeratorDishwasherWasherDryer
Basement
Full
Additional Rooms
FoyerGymLaundry RoomMud RoomSitting RoomWorkshop

Exterior & Lot

Lot Size
1.00 acres
Zoning
R-2
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Shake
Color
grey
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
French DoorsPatio
Lot Description
Fence - StoneLevel Lot

Listing & Financials

Property Taxes
$30,752 / Annually
Days on Market
0
MLS #
24206451
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Meghan Gatt

(203) 904-8064

William Raveis Real Estate

(203) 854-5116

Co-Listed By

Carla Kupiec

William Raveis Real Estate

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/14/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 9/14/2026 at 10:55 PM UTC.