38 Old Redding Road
Weston, Connecticut 06883
Reduced from $1,375,000
- Beds
- 4
- Baths
- 3 | 2
- SqFt
- 3,457
- Acres
- 2.00
- Year Built
- 1975
- Neighborhood
- Lower Weston
- Property Type
- Single Family

Matt Caiola
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About This Home
This sun-kissed contemporary captivates with private panoramic views overlooking the forever-green 14th and 15th fairways of Aspetuck Country Club. Designed to fully embrace its striking setting, this home offers a wide deck, large patio, five balconies, and grand windows framing views. Sited on two idyllic acres in bucolic Lower Weston, this premier property is minutes to the amenities and train stations of Westport and Fairfield. The home's immaculate exterior sets a welcoming tone with an oversized front porch with seating that beckons you inside. Upon entry, the home unfolds with an open layout featuring vaulted ceilings, skylights, walls of glass, rich wood floors, and fireplaces that add warmth and character. The main house offers a first-floor primary suite with walk-in closet and sunlit bath with double sinks, tub/shower, and sauna, along with access to a versatile loft. The great room features a dramatic two-story fireplace and flows into the dining room, living room, and kitchen, all filled with natural light and opening to the outdoor decks. Two powder rooms and a second loft level include a dedicated office, sitting room, & studio/recreation room. Lower level offers a family room with fireplace, three bedrooms, and a renovated full bathroom. Each room opens via sliders to decks/patio, and a laundry room completes this level. A renovated studio with separate entry and full bath offers multiple uses. A special home offering privacy, beauty, and seamless living
Key Facts
- City/Town
- Weston
- Neighborhood
- Lower Weston
- Property / Style
- Single Family · Contemporary
- Year Built
- 1975
- Days on Market
- 57 days
- Beds
- 4
- Baths
- 3 full · 2 half
- Living Area
- 3,457 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $15,907 / 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
$1.32M
vs $1.40M median
5.4% below median
Price / Sq Ft
$383
vs $381 median
In line with median
Days on Market
57 days
vs 48 days median
9 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
38 Old Redding Road, Weston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$6,756
- Property Taxes$1,326
- Insurance$442
- 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
- 3,457 sq ft
- Below Grade
- 1,178 sq ft
Schools
- Elementary
- Hurlbutt
- Middle
- Weston
- High
- Weston
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- ElectricOil
- Cooling
- Central AirWindow UnitZoned
- Fireplaces
- 2
- Laundry
- Lower Level
- Appliances
- Electric RangeMicrowaveRefrigeratorDishwasherCompactorWasherDryer
- Basement
- None
- In-Law Apartment
- PossibleOver Garage
- Interior Features
- Auto Garage Door OpenerSauna
- Additional Rooms
- Exercise RoomFoyerLaundry Room
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- R
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vertical SidingCedarWood
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BalconyShedDeckPatio
- Lot Description
- Fence - Electric PetGolf Course FrontageSome WetlandsTreedLevel Lot
Listing & Financials
- Property Taxes
- $15,907 / Annually
- Days on Market
- 57
- MLS #
- 24176914
- MLS Status
- Active
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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 7:55 AM UTC.