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158 Steep Hill Road

Weston, Connecticut 06883

ACTIVE - NEW$1,795,000
Beds
5
Baths
4
SqFt
4,577
Acres
2.15
Year Built
1978
Matt Caiola

Matt Caiola

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2-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,419

per 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

Similar Properties

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

Listed By

Christine Oleynick

(203) 912-9712

Keller Williams Realty

(203) 429-4020

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.