34 High Point Road
Westport, Connecticut 06880
- Beds
- 6
- Baths
- 6 | 2
- SqFt
- 7,132
- Acres
- 1.01
- Year Built
- 2022
- Neighborhood
- Long Lots
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Refined living awaits on one of Westport's most coveted cul-de-sac settings, nestled within the sought-after Long Lots neighborhood. The exceptional residence unfolds across four finished levels, offering six ensuite bedrooms, two additional half baths, and a thoughtfully designed layout that balances grand scale with everyday functionality. A glass-doored entry introduces interiors defined by opulence and impeccable craftsmanship. Formal living and dining rooms are elegantly appointed, complemented by a butler's pantry for seamless entertaining. The chef's kitchen is both stunning and highly functional. Flowing effortlessly into a sunlit breakfast room and family room with fireplace and wet bar, all have a front row view to the spacious backyard. A private office and well-designed utility room enhance daily living, while direct access to the three-car garage ensures convenience. The second level hosts five beautifully appointed ensuite bedrooms, including a luxurious primary suite complete with fireplace, bespoke walk-in closets, and a spa-inspired bath. An additional study or lounge space provides flexibility for work or relaxation. The third floor offers a sixth ensuite bedroom along with generous bonus space, ideal for guests or extended stays. The finished lower level is designed for recreation and wellness, featuring a media room, gym, game room, and ample storage. Comprised of park-like acre with room for a pool, the property offers both privacy and possibilities.
Key Facts
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
63
42 under contract
Median List Price
$5.00M
63 active listings
Median Closed Price
$2.42M
295 sales
Median Days on Market
45
63 active listings
Median $ / Sq Ft
$795
63 active listings
Sale-to-List Ratio
100.0%
295 sales
How this home compares
List Price
$4.59M
vs $5.00M median
8.0% below median
Price / Sq Ft
$644
vs $795 median
19.0% below median
Days on Market
0 days
vs 45 days median
45 days fresher than median
Based on 63 active and 295 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of October 30, 2026.
Location
34 High Point Road, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$25,052
- Property Taxes$3,605
- Insurance$1,532
- 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
- 2022
- New Construction
- No/Resale
- Living Area
- 7,132 sq ft
Schools
- Elementary
- Long Lots
- High
- Staples
Interior
- Heating
- Hydro AirSolarZoned
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Upper Level
- Appliances
- Gas RangeMicrowaveRange HoodRefrigeratorFreezerDishwasherWine Chiller
- Basement
- FullHeatedStorageFully FinishedCooledInterior AccessLiveable Space
- Interior Features
- Cable - AvailableOpen Floor PlanSecurity System
- Additional Rooms
- Bonus RoomGymLaundry RoomMud Room
Exterior & Lot
- Lot Size
- 1.01 acres
- Zoning
- AAA
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Beach RightsWater Community
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Construction
- ShingleClapboardVertical Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesGuttersLightingStone WallFrench DoorsUnderground SprinklerPatio
- Lot Description
- Sloping LotOn Cul-De-SacProfessionally Landscaped
Listing & Financials
- Property Taxes
- $43,260 / Annually
- Days on Market
- 0
- MLS #
- 24194698
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/30/2026. 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 10/30/2026 at 11:25 PM UTC.