32 Steep Hill Road
Weston, Connecticut 06883
Reduced from $2,595,000
- Beds
- 6
- Baths
- 6 | 1
- SqFt
- 7,050
- Acres
- 3.92
- Year Built
- 1750
- Neighborhood
- Lower Weston
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
A RARE property. The 28- year owners lovingly restored their 18th century antique and expanded it to 6,050 SF of modern comfort on its 4 acres including a 11/4 ac. pond. Albeit, the renovation of the property's antique 1,100 SF, 2 BR continually-rented cottage may be the financial coup for 42% marginal tax bracket (Fed+CT) buyers who assume a 6.25%, 80% ($2,080,000 of 2.6M asking) 30 yr. fixed mortgage. The rent, presently $30,000/yr., and tax advantaged deductions will contribute funds that amortize $915,000 of the 2.080M. Accordingly, the effective purchase price could be $1,685,000. High-quality finishes aside, consider the setting: brook-fed pond for large-mouth-bass anglers and visiting egrets; stunning fall foliage surrounding the pond; 450 ft. long, bleached-stone, maple tree-lined driveway to the main house; just a 2-minute drive to the Weston Town Center and K-12 school campus; 150 SF of veggie-intensive raised beds along with wild blackberries, and Concord grapes where you meander; pool site plans rendered and readied for the buyer; oversized-windows and 3rd floor balcony offering sweeping views; and a massive front lawn for that Great Tent celebration. Inside, a 2025-new heating system slashes the gas bill; a home office space w/ fireplace has its own private entrance; and the former, acclaimed NYC chef/owner's professionally equipped kitchen is central to the home's 5 entertaining areas, while a 600 SF bonus room with its own full kitchen invites countless uses.
Key Facts
- City/Town
- Weston
- Neighborhood
- Lower Weston
- Property / Style
- Single Family · Colonial,Farm House
- Year Built
- 1750
- Days on Market
- 161 days
- Beds
- 6
- Baths
- 6 full · 1 half
- Living Area
- 7,050 sq ft
- Lot Size
- 3.92 acres
- Garage / Parking
- 2 garage · 20 total
- Property Taxes
- $28,264 / Annually
Market Snapshot
The Weston Market
Single Family · trailing 12 months
Active Listings
39
22 under contract
Median List Price
$1.75M
39 active listings
Median Closed Price
$1.40M
128 sales
Median Days on Market
44
39 active listings
Median $ / Sq Ft
$397
39 active listings
Sale-to-List Ratio
102.0%
128 sales
How this home compares
List Price
$2.50M
vs $1.75M median
42.6% above median
Price / Sq Ft
$354
vs $397 median
10.8% below median
Days on Market
161 days
vs 44 days median
117 days longer than median
Based on 39 active and 128 closed sales (trailing 12 mo) of single family in Weston. Source: SmartMLS · As of September 11, 2026.
Location
32 Steep Hill Road, Weston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$12,959
- Property Taxes$2,355
- Insurance$832
- 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
- Colonial,Farm House
- Year Built
- 1750
- New Construction
- No/Resale
- Living Area
- 7,050 sq ft
Schools
- Elementary
- Hurlbutt
- Middle
- Weston
- High
- Weston
Interior
- Heating
- Hydro AirWall UnitZoned
- Heat Fuel
- Natural Gas
- Cooling
- Central AirZoned
- Fireplaces
- 3
- Laundry
- Upper Level
- Laundry Location
- Rear hallway
- Appliances
- Electric RangeWall OvenRange HoodRefrigeratorFreezerSubzeroDishwasherDisposalWasherGas Dryer
- Basement
- Crawl SpacePartialUnfinishedConcrete FloorPartial With Walk-Out
- In-Law Apartment
- PossibleSecond FloorSeparate Entry
- Interior Features
- Central Vacuum
- Additional Rooms
- Bonus RoomExercise RoomFoyerLaundry RoomSitting Room
Exterior & Lot
- Lot Size
- 3.92 acres
- Zoning
- R
- Garage / Parking
- 2 garage spaces20 total parking spacesAttached GarageDrivewayCrushed Stone
- Waterfront
- Direct waterfront
- Waterfront Details
- PondView
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- ClapboardWood
- Color
- Taupe
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Exterior Features
- TerraceGuttersLightingGuest HouseFrench DoorsPatioBalconyGarden AreaStone Wall
- Lot Description
- Some WetlandsTreedLevel LotSloping LotWater ViewOpen Lot
Listing & Financials
- Property Taxes
- $28,264 / Annually
- Days on Market
- 161
- MLS #
- 24160708
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/11/2026. 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 9/11/2026 at 11:50 PM UTC.