195 Steep Hill Road
Weston, Connecticut 06883
- Beds
- 5
- Baths
- 4
- SqFt
- 4,344
- Acres
- 2.42
- Year Built
- 1975
- Neighborhood
- Lower Weston
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Surrounded by nature and complete privacy, this unique home offers a peaceful retreat with exceptional indoor-outdoor living. A large, welcoming entry foyer features tile flooring and a skylight that fills the space with abundant natural light. Hardwood floors and custom windows are found throughout the home.The main level showcases a spacious living room with a wood-burning fireplace and walls of glass sliders that open to the pool & cabana. The eat-in kitchen with new marble countertops is open to the sunken den...creating the perfect setting for entertaining. The dining room is filled with natural light from solarium windows and features built-in window seating. The impressive two-story primary suite serves as a true sanctuary, complete with its own staircase leading up to a private loft with a wood-burning fireplace, perfect for a den or office. Dramatic floor-to-ceiling two-story windows and direct access to the pool and stone patio further elevate the space. Two additional bedrooms share a recently updated Jack & Jill bathroom. The lower level offers two more bedrooms, a full bath, and laundry area. An attached two-car garage adds convenience. Outside, enjoy your own private oasis in the fully fenced backyard featuring a gunite pool, expansive stone patio, and a cabana equipped with a kitchenette, second laundry, and full bath - ideal for entertaining or relaxing all summer long. Conveniently located to town, award-winning schools, dog park, Westport, Merritt Parkway.
Key Facts
- City/Town
- Weston
- Neighborhood
- Lower Weston
- Property / Style
- Single Family · Contemporary
- Year Built
- 1975
- Days on Market
- 55 days
- Beds
- 5
- Baths
- 4 full
- Living Area
- 4,344 sq ft
- Lot Size
- 2.42 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $18,371 / Annually
Market Snapshot
The Weston Market
Single Family · trailing 12 months
Active Listings
29
28 under contract
Median List Price
$1.40M
29 active listings
Median Closed Price
$1.38M
129 sales
Median Days on Market
48
29 active listings
Median $ / Sq Ft
$381
29 active listings
Sale-to-List Ratio
100.1%
129 sales
How this home compares
List Price
$1.25M
vs $1.40M median
10.7% below median
Price / Sq Ft
$288
vs $381 median
24.4% below median
Days on Market
55 days
vs 48 days median
7 days longer than median
Based on 29 active and 129 closed sales (trailing 12 mo) of single family in Weston. Source: SmartMLS · As of July 28, 2026.
Location
195 Steep Hill Road, Weston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$6,373
- Property Taxes$1,531
- Insurance$417
- 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
- 1975
- New Construction
- No/Resale
- Living Area
- 4,344 sq ft
- Below Grade
- 1,262 sq ft
Schools
- Elementary
- Hurlbutt
- Middle
- Weston
- High
- Weston
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 2
- Laundry
- Lower Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorFreezerDishwasher
- Basement
- FullStorageFully FinishedGarage AccessInterior AccessLiveable Space
Exterior & Lot
- Lot Size
- 2.42 acres
- Zoning
- R
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GunitePool HouseIn Ground Pool
- Construction
- Wood
- Roof
- Flat
- Foundation
- Concrete
- Exterior Features
- CabanaPatio
- Lot Description
- SecludedCorner LotRolling
Listing & Financials
- Property Taxes
- $18,371 / Annually
- Days on Market
- 55
- MLS #
- 24172499
- MLS Status
- Under Contract
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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 7/28/2026. 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 7/28/2026 at 5:25 AM UTC.