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329 Chestnut Hill Road #5

Norwalk, Connecticut 06851

PENDING$2,100,000
Beds
3
Baths
3 | 1
SqFt
4,146
Acres
0.31
Year Built
2020
Matt Caiola

Matt Caiola

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About This Home

: Final Offers Due 7/1 at 5PM : One of the most coveted enclaves in Fairfield County, WINDOVER, is a HOBI award-winning 8-home, 12-acre, private community just over the Wilton/Westport line. Highly sophisticated, designer-curated & professionally landscaped, this home is sited on one of the most private lots overlooking meadows, pond & near Cranbury park. A one-of-a-kind, primary or second residence AND HOA managed for a maintenance-free, Main-level living lifestyle. The stunning kitchen/great room area is swathed in natural light from the wall of sliders opening to the elevated bluestone patio w/ custom rail system. NEW private fenced courtyard off DR and rear fenced yard with owner-curated gardens. Every room is adorned w/ luxe, branded fixtures, appliances, & designer finishes. Subzero fridge + drawers, Wolf stovetop/oven & quartz-topped island overlooking the FR fireplace, wide-plank oak 7" floors, & sleek lines of custom trim work. The expansive butler's pantry incl: barn-style doors, custom cabinetry, wetbar, 2nd dishwasher, wine fridge & quartz tops. The primary suite is sumptuous w/ its vaulted ceilings, steam shower, radiant heated floor, soaking tub & WIC. Fully equipped laundry, mudroom & WIC complete the 1st floor. Upstairs, discover 2 well-proportioned BR suites w/ en-suite baths, plus light-filled office. 2 car garage w/ epoxy flooring & garage system from Garage Living. Just completed finished lower level w/ gym, office cedar closet & workshop.

Key Facts

City/Town
Norwalk
Neighborhood
Cranbury
Property / Style
Single Family · Colonial
Year Built
2020
Days on Market
31 days
Beds
3
Baths
3 full · 1 half
Living Area
4,146 sq ft
Lot Size
0.31 acres
Garage / Parking
2 garage · 2 total
Property Taxes
$28,267 / Annually
HOA Fee
$1,375 / Monthly

Market Snapshot

The Norwalk Market

Single Family · trailing 12 months

View area

Median Days on Market

28

75 active listings

Median $ / Sq Ft

$425

75 active listings

Sale-to-List Ratio

102.3%

516 sales

How this home compares

List Price

$2.10M

vs $900,000 median

2.3× the median

Price / Sq Ft

$507

vs $425 median

19.3% above median

Days on Market

31 days

vs 28 days median

3 days longer than median

Based on 75 active and 516 closed sales (trailing 12 mo) of single family in Norwalk. Source: SmartMLS · As of July 28, 2026.

Location

329 Chestnut Hill Road #5, Norwalk, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$15,138

per month

  • Principal & Interest$10,707
  • Property Taxes$2,356
  • Insurance$700
  • HOA$1,375

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

Location

City/Town
Norwalk
Neighborhood
Cranbury
County
Fairfield
Subdivision
Windover

Residence

Property Type
Single Family
Style
Colonial
Year Built
2020
New Construction
No/Resale
Living Area
4,146 sq ft
Below Grade
900 sq ft

Schools

Elementary
Cranbury
High
Norwalk

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Appliances
Gas CooktopWall OvenMicrowaveSubzeroDishwasherWasherDryerWine Chiller
Basement
FullHeatedStorageCooledInterior AccessPartially Finished
Interior Features
Auto Garage Door OpenerCable - Pre-wiredOpen Floor PlanSecurity System
Additional Rooms
FoyerLaundry RoomMud RoomSitting Room

Exterior & Lot

Lot Size
0.31 acres
Zoning
A3
Garage / Parking
2 garage spaces2 total parking spacesAttached GaragePavedDrivewayPrivatePavedAsphalt
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Wood
Roof
Wood Shingle
Foundation
Concrete
Exterior Features
GuttersGarden AreaLightingStone WallFrench DoorsUnderground SprinklerPatio
Lot Description
In SubdivisionDryOn Cul-De-SacProfessionally Landscaped

HOA / Association

Fee
$1,375 / Monthly
Amenities
Guest ParkingPark

Listing & Financials

Property Taxes
$28,267 / Annually
Days on Market
31
MLS #
24186977
MLS Status
Under Contract

Similar Properties

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

Listed By

Denise Walsh

(203) 650-1583

William Raveis Real Estate

(203) 255-6841

Co-Listed By

Kaitlyn Walsh

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 7/28/2026. 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 7/28/2026 at 12:01 AM UTC.