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14 High Point Road

Westport, Connecticut 06880

ACTIVE - NEW$2,999,999
Beds
5
Baths
5 | 1
SqFt
6,094
Acres
1.07
Year Built
2002
Matt Caiola

Matt Caiola

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Pool2-Car Garage2 Fireplaces

About This Home

Classic Colonial 5 Bedroom 5 - 1/2 Bath set on over 1 acre with a Gunite Swimming Pool on Westport's longest and perhaps, most sought after Cul-De-Sac! Almost 4700 sq ft on 1st & 2nd floors (hardwood flooring throughout), Plus 1400 sq ft in the fully finished, daylight, walk-out lower level. On the Main level the Gracious Living Room with Fireplace & Box Bay Window, is so large it easily accommodates the grand piano. Stroll through the Cocktail Lounge with built-ins, wet-bar & wine fridge to the delightful sunny, oversized Dining Room with dozens of windows & French Doors that lead to the rear deck. Circle back to the large Eat-In Kitchen with Island that seats four and a dedicated Dining Area by the Bay Window, this all seamlessly flows into the Family Room with Fireplace, Built-In Bookshelves and French Doors opening to the rear deck with views of the pool below. Rounding out the first floor are a Home Office, Ensuite Guest Bedroom with a Full Bath and Walk-In Closet, Half Bath in hall. The 2nd floor has an Enormous Primary Suite with Spa Bath, 3 Walk-In closets & Office or Dressing Room attached to the suite. The 2nd level has 3 more spacious family bedrooms, including one with an ensuite bath and walk-in closet and two more that have ample closet space and share a hall bath. The daylight, walkout lower level has a full bath, tv/media room, gym/playroom with sink, d/w, and fridge and a bonus storage room. Generac Generator! Walls freshly painted! Newer -Roof, HVAC, Septic!

Key Facts

City/Town
Westport
Neighborhood
Long Lots
Property / Style
Single Family · Colonial
Year Built
2002
Days on Market
0 days
Beds
5
Baths
5 full · 1 half
Living Area
6,094 sq ft
Lot Size
1.07 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$24,570 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

35

70 active listings

Median $ / Sq Ft

$779

70 active listings

Sale-to-List Ratio

100.0%

299 sales

How this home compares

List Price

$3.00M

vs $4.67M median

35.8% below median

Price / Sq Ft

$492

vs $779 median

36.8% below median

Days on Market

0 days

vs 35 days median

35 days fresher than median

Based on 70 active and 299 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of October 15, 2026.

Location

14 High Point Road, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$19,665

per month

  • Principal & Interest$16,617
  • Property Taxes$2,048
  • Insurance$1,000
  • HOA$0

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

Location

City/Town
Westport
Neighborhood
Long Lots
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
2002
New Construction
No/Resale
Living Area
6,094 sq ft
Below Grade
1,400 sq ft

Schools

Elementary
Per Board of Ed
High
Staples

Interior

Heating
Hot AirHot WaterZoned
Heat Fuel
OilPropane
Cooling
Central AirZoned
Fireplaces
2
Laundry
Upper Level
Laundry Location
2nd Floor Landing
Appliances
Gas CooktopWall OvenRefrigeratorDishwasherWasherDryerWine Chiller
Basement
FullHeatedGarage AccessCooledInterior AccessLiveable SpaceFull With Walk-Out
In-Law Apartment
PossibleFirst Floor
Interior Features
Auto Garage Door Opener
Additional Rooms
Bonus RoomExercise RoomGym

Exterior & Lot

Lot Size
1.07 acres
Zoning
AA
Garage / Parking
2 garage spaces6 total parking spacesAttached GarageUnder House GaragePavedDrivewayPrivatePavedAsphalt
Waterfront Details
Beach Rights
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
No
Pool
GuniteHeatedSafety FenceIn Ground Pool
Construction
Clapboard
Color
White
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckGuttersFrench DoorsUnderground SprinklerPatio
Lot Description
Fence - PartialSome WetlandsLevel LotSloping LotOn Cul-De-Sac

Listing & Financials

Property Taxes
$24,570 / Annually
Days on Market
0
MLS #
24213615
MLS Status
Active

Similar Properties

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

Listed By

Joelle Malec

(203) 209-1131

William Raveis Real Estate

(203) 227-4343

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/15/2026. 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 10/15/2026 at 3:26 PM UTC.