Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,795,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 4,577 Sq. Ft.
  • 2 Car Garage
  • Updated 8 hours ago

Next open house:

Open House: 12:00 PM - 2:00 PM

Sunday 9/13 12:00 PM - 2:00 PM

158 Steep Hill Road,Weston, CT 06883

158 Steep Hill RoadWestonCT06883

Get directions
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 158 Steep Hill Rd

General

  • Price: $1,795,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24205738
  • Updated: 9/10/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 8
  • Interior Features: Auto Garage Door Opener, Cable - Available, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Cook Top, Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Balcony/Deck, Bedroom Suite, Fireplace, Full Bath, Walk-In Closet, Hardwood Floor, Main
  • Bedroom 1: Bedroom - Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Hardwood Floor, Upper
  • Bedroom 4: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Balcony/Deck, Fireplace, Hardwood Floor, Main
  • Family Room: Family Room - Engineered Wood Floor, Lower
  • Eat In Kitchen: Eat-In Kitchen - Balcony/Deck, Breakfast Bar, Quartz Counters, Eating Space, Ha, Main
  • Dining Room: Dining Room - Skylight, 9 ft+ Ceilings, Balcony/Deck, Beams, Patio/Terrace, Hardwood Floor, Main
  • Laundry: Main Level
  • Other Room 1: Other - Patio/Terrace, Sliders, Engineered Wood Floor, Lower

Exterior

  • Exterior Features: Balcony, Porch, Deck, Gutters, Lighting, Covered Deck
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking: Attached Garage, Paved, Driveway

Location

  • County: Fairfield
  • Neighborhood: Lower Weston
  • Driving Directions: GPS friendly

School Information

  • Elementary School: Hurlbutt
  • Middle School: Weston
  • Intermediate School: Weston
  • High School: Weston

Community

  • Community Name: Lower Weston

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Contemporary
  • Construction Status: No/Resale
  • Exterior Const.: Shingle
  • Basement Desc.: Full, Heated, Garage Access, Cooled, Interior Access, Liveable Space, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,577
  • Above Ground: 3,518 Sq. Ft.
  • Below Ground: 1,059 Sq. Ft.
  • Year Built: 1978

Lot Features

  • Lot Size (Acres): 2.15
  • Driveway/Sidewalk: Private, Circular
  • Zoning: R
  • Lot Description: Sloping Lot

Water Features

  • Water Front Desc.: Beach Rights

Financial Considerations

  • Assessment Amount: $752,150
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Ask for exclusion list
  • Property ID: 404954

Listed by Keller Williams Realty, THE CHRISTINE OLEYNICK TEAM, Christine Oleynick

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 158 Steep Hill Rd —

  • Christine Oleynick

    Keller Williams Realty

Agent Contact: (203) 912-9712 Office Contact: (203) 429-4020

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 158 Steep Hill Rd

School District:Weston School District
NameGradesDistance
Weston Intermediate School
95 School Road, Weston, CT 06883
3-51.7 mi
Hurlbutt Elementary School
9 School Road, Weston, CT 06883
PK-22 mi
Weston Middle School
135 School Road, Weston, CT 06883
6-81.5 mi
Weston High School
115 School Road, Weston, CT 06883
9-121.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 158 Steep Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/09/2026
Listed
$1,795,000
112.11%
MLS
6/28/2002
Sold
$846,250
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 158 Steep Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$17,976
2%
$752,150
—
2023
$17,653
—
$752,150
41%
2023
$17,585
—
$531,900
—
2022
$17,537
—
$531,900
—
2021
$17,510
2%
$531,900
—
2020
$17,218
—
$531,900
—
2019
$17,218
1%
$531,900
-8%
2018
$17,008
2%
$578,700
1%
2017
$16,643
1%
$575,700
—
2016
$16,442
—
$575,700
—
2015
$16,505
3%
$575,700
-14%
2013
$16,061
—
$672,300
—
2011
$16,061
—
$672,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 158 Steep Hill Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Keller Williams Realty, THE CHRISTINE OLEYNICK TEAM, Christine Oleynick

Similar Properties near 158 Steep Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

62 Wells Hill Rd, Weston, CT 06883 - Photo 1 Just Listed
$1,880,000
Open House

62 Wells Hill Rd  Weston, CT 06883

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,965
    Sq. Ft.
Listed by Compass Connecticut, LLC
23 Norton Rd, Easton, CT 06612 - Photo 1 Just Listed
$1,575,000
Open House

23 Norton Rd  Easton, CT 06612

  • Single Family
  • Active
  • Updated 13 hours ago
  • 5
    Beds
  • 4
    Total Baths
  • 5,079
    Sq. Ft.
Listed by Higgins Group Real Estate
28 Old Orchard Dr, Weston, CT 06883 - Photo 1
$1,779,000

28 Old Orchard Dr  Weston, CT 06883

  • Single Family
  • Active
  • Updated 6 days ago
  • 5
    Beds
  • 6
    Total Baths
  • 7,611
    Sq. Ft.
Listed by Bross Chingas Bross Team at Coldwell Banker Realty (203) 454-8000
129 Davis Hill Rd, Weston, CT 06883 - Photo 1
$1,695,000

129 Davis Hill Rd  Weston, CT 06883

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 3,822
    Sq. Ft.
Listed by Georgia Wasserman (917) 923-5400

Just Listed near 158 Steep Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

24 Graenest Ridge Rd, Wilton, CT 06897 - Photo 1 Just Listed
$3,800,000

24 Graenest Ridge Rd  Wilton, CT 06897

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 4,386
    Sq. Ft.
Listed by Compass Connecticut, LLC
146 Westport Rd, Wilton, CT 06897 - Photo 1 Just Listed
$895,000
Open House

146 Westport Rd  Wilton, CT 06897

  • Single Family
  • Active
  • Updated 8 hours ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,798
    Sq. Ft.
Listed by Compass Connecticut, LLC
122 Millstone Rd, Wilton, CT 06897 - Photo 1 Just Listed
$1,795,000
Open House

122 Millstone Rd  Wilton, CT 06897

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 5
    Total Baths
  • 4,640
    Sq. Ft.
Listed by Compass Connecticut, LLC
315 Olmstead Hill Rd, Wilton, CT 06897 - Photo 1 Just Listed
$899,000

315 Olmstead Hill Rd  Wilton, CT 06897

  • Single Family
  • Active
  • Updated 8 hours ago
  • 3
    Beds
  • 4
    Total Baths
  • 2,635
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l

Price Reduced near 158 Steep Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

8 Glen Ridge, Wilton, CT 06897 - Photo 1 Price Reduced
-$34,000 (-4.48%)
$725,000
Open House

8 Glen Ridge  #8  Wilton, CT 06897

  • Townhouse
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,394
    Sq. Ft.
Listed by Brown Harris Stevens
311 Mountain Rd, Wilton, CT 06897 - Photo 1 Price Reduced
-$36,000 (-3.32%)
$1,049,000

311 Mountain Rd  Wilton, CT 06897

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,300
    Sq. Ft.
Listed by William Raveis Real Estate
89 Chestnut Hill Rd, Wilton, CT 06897 - Photo 1 Price Reduced
-$300,000 (-11.13%)
$2,395,000
Open House

89 Chestnut Hill Rd  Wilton, CT 06897

  • Single Family
  • Active
  • Updated 14 hours ago
  • 6
    Beds
  • 5
    Total Baths
  • 5,576
    Sq. Ft.
Listed by Brown Harris Stevens
River Ln, Westport, CT 06880 - Photo 1 Price Reduced
-$100,000 (-6.25%)
$1,500,000

River Ln  Westport, CT 06880

  • Land Residential
  • Active
  • Updated 1 day ago
  • 1.13
    Acres
Listed by Compass Connecticut, LLC

Recent Sales near 158 Steep Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

9 Patchen Ln, Weston, CT 06883 - Photo 1 Sold
$1,565,000

9 Patchen Ln  Weston, CT 06883

  • Single Family
  • Closed
  • 4
    Beds
  • 5
    Total Baths
  • 5,676
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Pitt Sotheby's Int'l
38 Lords Hwy E, Weston, CT 06883 - Photo 1 Sold
$1,600,000

38 Lords Hwy E  Weston, CT 06883

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 4,264
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Raveis Real Estate
21 Laurel Lake E, Weston, CT 06883 - Photo 1 Sold
$1,895,000

21 Laurel Lake E  Weston, CT 06883

  • Single Family
  • Closed
  • 5
    Beds
  • 5
    Total Baths
  • 4,370
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by Houlihan Lawrence
23 Old Stage Coach Rd, Weston, CT 06883 - Photo 1 Sold
$2,000,000

23 Old Stage Coach Rd  Weston, CT 06883

  • Single Family
  • Closed
  • 4
    Beds
  • 5
    Total Baths
  • 4,312
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Raveis Real Estate

158 Steep Hill Road, Weston, CT 06883 (MLS# 24205738) is a Single Family property with 5 bedrooms and 4 full bathrooms. 158 Steep Hill Road is currently listed for $1,795,000 and was received on September 09, 2026. Want to learn more about 158 Steep Hill Road? Do you have questions about finding other Single Family real estate for sale in Weston? You can browse all Weston real estate or contact a Coldwell Banker agent to request more information.

Tour this property