Home / Listings / Wilton
Active · For Sale
$2,395,000

249 Chestnut Hill Road, Wilton, Connecticut 06897

5 beds 7 baths 8,685 sq ft Single Family For Sale Built 2008

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...

Status
Active
Type
Single Family For Sale
Price
$2,395,000
Beds
5
Baths
7
Interior
8,685 sq ft
Lot
1 ac
Year Built
2008
MLS #
24206451
ZIP
06897
Days on Market
4
Heat
Oil · Hot Air
Cooling
Central Air
Water
Private Well
Sewer
Septic
Parking
Attached Garage (3-car)
Laundry
Upper Level

Flood risk: check the FEMA flood map for this address.

Schools

Elementary
Miller-Driscoll
High School
Wilton

Taxes

Property tax
$30,752 (July 2026-June 2027)
Assessed value
$1,227,030

Interior

Appliances
Cook Top, Wall Oven, Refrigerator, Dishwasher, Washer, Dryer
Basement
Full
Fireplaces
3
Total rooms
11

Building & Exterior

Style
Colonial
Roof
Asphalt Shingle
Siding
Shake
Exterior features
French Doors, Patio
Foundation
Concrete
New construction
No/Resale

Lot & Land

Zoning
R-2
Lot
Fence - Stone, Level Lot

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

/mo
principal & interest

What's nearby

Grocery
Lily's Weston Market1.26 mi away
Also nearby
Stop & Shop1.81 mi away
Pharmacy
CVS Pharmacy3.85 mi away
Train
Wilton Station1.87 mi awayMetro-North Railroad
Bus stop
Wolfpit Park & Ride1.15 mi away
Elementary
Miller-Driscoll
High school
Wilton
School zone
Check the district's school finder the MLS did not name one for this address
~3.0 miLily's Weston Market — 1.26 miStop & Shop — 1.81 miCVS Pharmacy — 3.85 miWilton — 1.87 miWolfpit Park & Ride — 1.15 mi
This homeGroceryPharmacyTrainBus

Real streets from OpenStreetMap; distances are straight-line from the property, not driving routes.

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $2,395,000, ranging $1,800,000 to $3,540,000.

Public record

From the Wilton assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

Year built2008
Living area6,368 sq ft
Total rooms11
Lot size1 acres
Stories3
HeatForced Air
ExteriorWood Shingle
Assessed value$1,227,030
Town appraisal$1,752,900
Last recorded sale2013 — $1,600,000

Recorded sales

Deed transfers on file with the Wilton land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.

Listing courtesy of William Raveis Real Estate — Meghan Gatt · (203) 854-5116

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