299 Saugatuck Avenue
Westport, Connecticut 06880
- Beds
- 4
- Baths
- 4 | 2
- SqFt
- 5,627
- Acres
- 1.10
- Year Built
- 1987
- Neighborhood
- Saugatuck
- 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
*THANK YOU FOR YOUR INTEREST, SELLER REQUESTS HIGHEST/BEST OFFERS BY 3PM MONDAY 6/1/26*Set on over an acre of park-like, usable property, this stunning Modern home with an oversized gunite pool is a showcase of exhilarating design. In an area known for major watefront properties as well as immediate convenience to the railroad station and all commuting routes, this home blends sophisticated elegance with an easy lifestyle. A gracious, landscaped approach brings you to the grand double-door entrance lined with windows and into a vaulted ceiling foyer. The interior captures gorgeous light all day through walls of glass & numerous skylights. The floor plan is an entertainer's dream, accommodating groups large or small in refined surroundings. The living and family rooms each have floor-to-ceiling stone fireplaces and glass doors to the rear deck. The DR has a picture-perfect view across the property. Gourmet E-I-K w/Wolf gas cooktop, Sub Zero ref/frz, Viking double ovens, pantry, center island w/seating & a breakfast area enhanced by scenic views. An adjacent sunroom transitions the space out to the deck. Two half baths complete this level. The airy atmosphere continues up front & rear stairs to the 2nd level, beginning w/a grand primary suite w/priv sitting rm, king-size BR w/pool view balcony, vast dressing rm & two lux baths. Three addl' BRs have double clsts & two full baths. Fin LL w/rec rm, office, storage. Enjoy a porch that leads to the pool/spa. 3 car garage, generator.
Key Facts
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
70
56 under contract
Median List Price
$4.70M
70 active listings
Median Closed Price
$2.42M
303 sales
Median Days on Market
60
70 active listings
Median $ / Sq Ft
$821
70 active listings
Sale-to-List Ratio
100.0%
303 sales
How this home compares
List Price
$2.80M
vs $4.70M median
40.4% below median
Price / Sq Ft
$497
vs $821 median
39.5% below median
Days on Market
64 days
vs 60 days median
4 days longer than median
Based on 70 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.
Location
299 Saugatuck Avenue, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$14,271
- Property Taxes$1,619
- Insurance$933
- 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
- Contemporary,Modern
- Year Built
- 1987
- New Construction
- No/Resale
- Living Area
- 5,627 sq ft
- Below Grade
- 773 sq ft
Schools
- Elementary
- Kings Highway
- High
- Staples
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- Oil
- Cooling
- Central AirZoned
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Gas CooktopWall OvenMicrowaveRange HoodSubzeroIcemakerDishwasherWasherDryer
- Basement
- FullStorageInterior AccessPartially FinishedLiveable SpaceFull With Hatchway
- In-Law Apartment
- PossibleLower Level
- Interior Features
- Audio SystemAuto Garage Door OpenerCable - AvailableHumidifierOpen Floor PlanSecurity System
- Additional Rooms
- FoyerLaundry Room
Exterior & Lot
- Lot Size
- 1.10 acres
- Zoning
- AA
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- Yes
- Pool
- GuniteHeatedSpaIn Ground Pool
- Construction
- ClapboardCedar
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BalconyPorchDeckLightingUnderground SprinklerPatio
- Lot Description
- Fence - PartialLevel LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $19,422 / Annually
- Days on Market
- 64
- MLS #
- 24169465
- MLS Status
- Under Contract
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 7/27/2026. 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 7/27/2026 at 11:40 AM UTC.