28 Old Orchard Drive
Weston, Connecticut 06883
- Beds
- 5
- Baths
- 5 | 1
- SqFt
- 7,611
- Acres
- 2.00
- Year Built
- 1986
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer. Large windows that fill the rooms w/sunlight are a defining characteristic of the home, including the cathedral-ceil LR w/stone fpl & wide plank floors, holiday-sized DR w/bay window, fam rm w/wet bar and wall of glass to deck. The dine-in kitchen w/ center island, updated stainless steel appls incl gas cooktop & Sub Zero, also opens out to the large deck. A main flr office & 1.5 bths complete the main lvl. Front & rear staircases lead up to the spacious 2nd level where you will find a grand primary suite w/lrg walk-in clst & en-suite bth plus 3 addl BRs & 2 full baths. The incredible finished, walk-out lower level is a highlight, with sun-drenched spaces that add spacious comfort, flexibility and can meet any need - while still offering great storage. The rec rm w/fpl and a pair of offices or bonus rms each have doors to the rear property. The gym has an adjacent full bth, making it an ideal cabana for swimming guests using the pool when entertaining in these splendid surroundings. Enjoy gorgeous views & tranquil privacy, just minutes to the town Center & school campus plus commuting.
Key Facts
- City/Town
- Weston
- Neighborhood
- N/A
- Property / Style
- Single Family · Contemporary
- Year Built
- 1986
- Days on Market
- 461 days
- Beds
- 5
- Baths
- 5 full · 1 half
- Living Area
- 7,611 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $25,674 / 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
$1.78M
vs $1.40M median
27.1% above median
Price / Sq Ft
$234
vs $381 median
38.6% below median
Days on Market
461 days
vs 48 days median
413 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
28 Old Orchard Drive, Weston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$9,071
- Property Taxes$2,140
- Insurance$593
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Weston
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1986
- New Construction
- No/Resale
- Living Area
- 7,611 sq ft
- Below Grade
- 3,532 sq ft
Schools
- Elementary
- Hurlbutt
- Middle
- Weston
- High
- Weston
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- Oil
- Cooling
- Ceiling FansCentral AirZoned
- Fireplaces
- 3
- Laundry
- Upper Level
- Appliances
- Gas CooktopWall OvenRange HoodRefrigeratorFreezerSubzeroIcemakerDishwasherInstant Hot Water TapWasherElectric Dryer
- Basement
- FullHeatedStorageCooledPartially FinishedLiveable SpaceFull With Walk-Out
- In-Law Apartment
- PossibleLower LevelSeparate Entry
- Interior Features
- Audio SystemAuto Garage Door OpenerCable - Pre-wiredCentral VacuumSaunaSecurity System
- Additional Rooms
- FoyerLaundry RoomMud RoomSteam/SaunaWine Cellar
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- R
- Garage / Parking
- 2 garage spaces6 total parking spacesAttached GaragePavedDrivewayPrivateCircularPavedAsphalt
- Waterfront Details
- Beach Rights
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- GuniteHeatedTileSafety FenceIn Ground Pool
- Construction
- ShingleWood
- Color
- Cream
- Roof
- Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesDeckGuttersGarden AreaLightingStone WallUnderground SprinklerPatio
- Lot Description
- Fence - PartialFence - Electric PetLightly WoodedDryClearedProfessionally LandscapedRolling
Listing & Financials
- Property Taxes
- $25,674 / Annually
- Days on Market
- 461
- MLS #
- 24079433
- 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 7:01 AM UTC.