36 Old Orchard Drive
Weston, Connecticut 06883
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 5,912
- Acres
- 2.00
- Year Built
- 1974
- Neighborhood
- Devil's Den
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
The New Sensation! Don't miss the opportunity to see this sun drenched 4-5 bedroom Contemporary home w/ a flexible floorplan to suit a variety of lifestyles! An entertainer's dream, this home offers something for everyone. The charming entry greets you as you step into the front parlor w/ a marble surround fireplace. A stepdown into the large family/living room w/ wetbar, built-ins, fireplace & sun solarium overlooking beautiful pool & grounds. The light & bright dining room w/ sliders to a private deck also flows into the spectacular kitchen. Your friends & family will love being entertained in this fabulous space w/ huge center island w/ five burner cook top & 2 sinks, 6 burner Viking range as well as two additional wall ovens (one w/ a pizza stone), 2 dishwashers, huge side by side Subzero, walk-in pantry, fireplace, built-ins & eat-in dining area leading to multi-tiered decking & heated in ground pool and pavilion. The main level of the home also includes lovely guest quarters w/ensuite bath & large closet. The light filled sunken Primary bedroom has fireplace, walls of glass for viewing spectacular sunrises, dual walk in closets & large bath w/spa tub & walk-in shower. The 2nd floor offers 2 bedrooms w/ bath & a bonus room (playroom, music room etc).The full walkout lower level boasts pool cabana, media room,full bath, office, workout space, large cedar closet & flexible spaces for 5th BR. All of this & so much more just minutes to Weston school campus & town center!
Key Facts
- City/Town
- Weston
- Neighborhood
- Devil'S Den
- Property / Style
- Single Family · Colonial,Contemporary
- Year Built
- 1974
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 4 full · 1 half
- Living Area
- 5,912 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 4 garage
- Property Taxes
- $24,143 / 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
$2.19M
vs $1.75M median
25.1% above median
Price / Sq Ft
$370
vs $397 median
6.8% below median
Days on Market
0 days
vs 44 days median
44 days fresher 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
36 Old Orchard Drive, Weston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$11,370
- Property Taxes$2,012
- Insurance$730
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Weston
- Neighborhood
- Devil'S Den
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Contemporary
- Year Built
- 1974
- New Construction
- No/Resale
- Living Area
- 5,912 sq ft
- Below Grade
- 1,500 sq ft
Schools
- Elementary
- Hurlbutt
- Middle
- Weston
- High
- Weston
Interior
- Heating
- Hot AirZoned
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 4
- Appliances
- Cook TopGas RangeWall OvenRefrigeratorFreezerSubzeroDishwasherWasherDryer
- Basement
- FullHeatedCooledInterior AccessPartially FinishedLiveable SpaceFull With Walk-Out
- Interior Features
- Audio SystemCentral VacuumSecurity System
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- R
- Garage / Parking
- 4 garage spacesAttached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- HeatedVinylIn Ground Pool
- Construction
- ShingleWood
- Color
- blue
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- BalconyAwningsCabanaDeckGuttersLightingUnderground Sprinkler
- Lot Description
- Some WetlandsTreedLevel LotSloping LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $24,143 / Annually
- Days on Market
- 0
- MLS #
- 24202562
- 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 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 8:10 AM UTC.