158 Steep Hill Road

Weston, CT
$ 1,795,000 Beds 5 Baths 4 Sq 4,577
Monthly Estimate* How much can I afford?

Light-filled, beautifully renovated and wonderfully versatile, this striking Weston 5/6 bedroom 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.

Single Family

  • Price
  • $ 1,795,000
  • City
  • Weston
  • Bedrooms
  • 5
  • Full Bathrooms
  • 4
  • County
  • Fairfield
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 2.15 Acres
  • Zip
  • 06883
  • Sqr Footage
  • 4,577
  • Year Built
  • 1978
  • Taxes
  • $ 17976
  • Style
  • MLS#
  • 24205738
Listed By: Christine Oleynick 203-912-9712 with Keller Williams Realty. - (203) 429-4020
Data Source: Smart MLS

Features

General

Zoning R
Neighborhood Lower Weston
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.15
Directions GPS friendly
High School Weston
City Weston
Elementary School Hurlbutt
Sq Ft Total 4577
DOM 10
Year Built 1978
Exclusions Ask for exclusion list
Style Contemporary
Year Built Source Public Records

Interior Features

Cooling System Central Air
Total Rooms 8
Basement Description Full,Heated,Garage Access,Cooled,Interior Access,Liveable Space,Full With Walk-Out

Exterior Features

Water Source Private Well
Lot Description Sloping Lot
Color White

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Hurlbutt Elementary School
Middle School Unknown Middle School
High School Weston High School

Price History

9/10/2026 Listed $1,795,000

Property vs Zip Code Average in 06883

Price
AVG $1.86M
$1.8M
Taxes
AVG $22,074
$17,976
Year Built
AVG 1969
1978

In The Neighborhood

Areas That We Cover

158 Steep Hill Road Weston, CT is a Single Family Home for sale at $1795000 with 4577 sqft and a lot size of 2.15 Acres Acre(s). 158 Steep Hill Road Weston has 5 bedrooms, 4 baths and was built in 1978. The property's zip code is 06883 which is in Weston, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

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