14 High Point Road
Westport, Connecticut 06880
- Beds
- 5
- Baths
- 5 | 1
- SqFt
- 6,094
- Acres
- 1.07
- Year Built
- 2002
- Neighborhood
- Long Lots
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
70
40 under contract
Median List Price
$4.67M
70 active listings
Median Closed Price
$2.42M
299 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per 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
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
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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.