Weston, CT / 8 DAYS ON MARKET

158 Steep Hill RoadWeston, CT 06883

Asking price$1,795,000Active

Open house

  • Saturday, September 19, 202611:00 am – 1:00 pm ET

Our Take

158 Steep Hill Road in Weston is a five-bedroom contemporary on 2.15 acres, with a private setting and flexible spaces for household living, guests, or work. The great room has cathedral ceilings, skylights, and walls of windows, while the open layout connects the living and dining areas to a renovated kitchen with brand-new appliances. A main-level primary suite supports one-floor living. Additional options include a space above the garage and a finished lower level with recreation, fitness, kitchenette, and possible sixth-bedroom uses. Multiple decks overlook the private yard, and residents enjoy beach rights at Westport’s Compo Beach.

Estimated buyer rebate

Buy with Cress and Save $17,950 on brokerage fees*

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*Estimate assumes a 2.5% buyer-agent commission and a 40% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24205738
Bedrooms
5
BathroomsBaths
4 full / 0 half
Square feet
4,577
Year built
1978
Acres
2.15
Property taxes
$17,976

July 2025-June 2026

What stands out

  • Cathedral-ceilinged great room with skylights
  • Renovated kitchen with brand-new appliances
  • Main-level primary suite
  • Private space above garage for guests or office
  • Finished lower level with recreation and fitness areas
  • Multiple decks overlooking the private yard
  • Two fireplaces for living and entertaining
  • Beach rights at Westport’s Compo Beach
Read the full listing description

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.

Schools

Elementary
Hurlbutt
Middle
Weston
High
Weston

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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158 Steep Hill Road, Weston, CT 06883

Price history

DateEventPrice
Originally listed$1,795,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $1,795,000 asking price × assumed 2.5% buyer-agent commission × 40% rebate = $17,950. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by Keller Williams Realty · (203) 429-4020

Christine Oleynick

SmartMLS · Listing #24205738 · Active

Listing data checked: Sep 17, 2026, 7:10 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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