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38 Old Redding Road

Weston, Connecticut 06883

ACTIVE$1,325,000

Reduced from $1,375,000

Beds
4
Baths
3 | 2
SqFt
3,457
Acres
2.00
Year Built
1975
Matt Caiola

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,524

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Lori Elkins Ferber

(203) 247-0450

William Raveis Real Estate

(203) 227-4343

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.