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195 Steep Hill Road

Weston, Connecticut 06883

PENDING$1,250,000
Beds
5
Baths
4
SqFt
4,344
Acres
2.42
Year Built
1975
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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Pool2-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,321

per 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

Similar Properties

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Listed By

Jenny Walsh

(203) 249-9851

Coldwell Banker Realty

(203) 227-8424

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.