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36 Old Orchard Drive

Weston, Connecticut 06883

ACTIVE - NEW$2,189,000
Beds
5
Baths
4 | 1
SqFt
5,912
Acres
2.00
Year Built
1974
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Pool4-Car Garage4 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$14,112

per 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

Similar Properties

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

Listed By

Carrie Shea

(203) 858-7699

Camelot Real Estate

(203) 226-3568

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.