158 Steep Hill Road
Weston, Connecticut 06883
- Beds
- 5
- Baths
- 4
- SqFt
- 4,577
- Acres
- 2.15
- Year Built
- 1978
- Neighborhood
- Lower Weston
- Property Type
- Single Family

Matt Caiola
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About This Home
Light-filled, beautifully renovated and wonderfully versatile, this striking Weston contemporary offers over 5,000 square feet of living space in a private yet convenient setting. From the moment you enter, the home impresses with a dramatic great room featuring soaring cathedral ceilings, skylights and walls of windows that bring the outdoors in. Designed for everyday living and entertaining, the open, airy floor plan features two fireplaces and multiple decks for relaxing and enjoying the surrounding landscape. The renovated kitchen offers brand-new appliances, generous workspace and an easy connection to the living and dining areas. The main-level primary suite provides the ease of one-floor living, while additional bedrooms offer plenty of room for family and guests. A private space above the garage is ideal as an au pair suite, guest quarters or home office. The finished lower level adds even more flexibility with space for a possible 6th BR, recreation/media room, fitness area and kitchenette. Numerous decks overlook the beautiful private yard. Just minutes from charming Weston Center and Weston's top-rated schools, residents also enjoy beach rights at Westport's Compo Beach. A rare combination of space, style, privacy and convenience. Enjoy the best of Weston living-peaceful surroundings, award-winning schools (bus stop at end of driveway!), a welcoming town center and easy access to Westport's shopping, dining, train and beaches.
Key Facts
- City/Town
- Weston
- Neighborhood
- Lower Weston
- Property / Style
- Single Family · Contemporary
- Year Built
- 1978
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 4 full
- Living Area
- 4,577 sq ft
- Lot Size
- 2.15 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $17,976 / Annually
Market Snapshot
The Weston Market
Single Family · trailing 12 months
Active Listings
37
22 under contract
Median List Price
$1.75M
37 active listings
Median Closed Price
$1.40M
128 sales
Median Days on Market
45
37 active listings
Median $ / Sq Ft
$397
37 active listings
Sale-to-List Ratio
102.0%
128 sales
How this home compares
List Price
$1.79M
vs $1.75M median
In line with median
Price / Sq Ft
$392
vs $397 median
In line with median
Days on Market
0 days
vs 45 days median
45 days fresher than median
Based on 37 active and 128 closed sales (trailing 12 mo) of single family in Weston. Source: SmartMLS · As of September 11, 2026.
Location
158 Steep Hill Road, Weston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$9,323
- Property Taxes$1,498
- Insurance$598
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Weston
- Neighborhood
- Lower Weston
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1978
- New Construction
- No/Resale
- Living Area
- 4,577 sq ft
- Below Grade
- 1,059 sq ft
Schools
- Elementary
- Hurlbutt
- Middle
- Weston
- High
- Weston
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- Main level
- Appliances
- Cook TopOven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullHeatedGarage AccessCooledInterior AccessLiveable SpaceFull With Walk-Out
- In-Law Apartment
- PossibleLower Level
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor Plan
Exterior & Lot
- Lot Size
- 2.15 acres
- Zoning
- R
- Garage / Parking
- 2 garage spaces4 total parking spacesAttached GaragePavedDrivewayPrivateCircular
- Waterfront Details
- Beach Rights
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Shingle
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BalconyPorchDeckGuttersLightingCovered Deck
- Lot Description
- Sloping Lot
Listing & Financials
- Property Taxes
- $17,976 / Annually
- Days on Market
- 0
- MLS #
- 24205738
- 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 9/11/2026. 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 9/11/2026 at 1:25 AM UTC.