21 Deepwood Road
Weston, Connecticut 06883
- Beds
- 5
- Baths
- 3
- SqFt
- 4,336
- Acres
- 2.14
- Year Built
- 1979
- Neighborhood
- Lower Weston
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Nestled at the end of a quiet cul-de-sac on two picturesque acres, this extraordinary five-bedroom, three full bath residence offers a rare combination of timeless elegance and peaceful seclusion. Overlooking a gently flowing brook, the property is surrounded by natural beauty, creating a private retreat just minutes from the vibrant shops, acclaimed restaurants, beaches, and Metro-North train station in neighboring Westport. Designed for both everyday living and effortless entertaining, the home features two luxurious primary suites, including one on the main level and a second upstairs with its own private balcony overlooking the tranquil landscape. The sleek kitchen is beautifully appointed with new countertops, while the bathrooms offer sophisticated, contemporary finishes. Brand-new Andersen windows throughout bathe the home in natural light while enhancing comfort and efficiency. Offering an exceptional balance of privacy, convenience, and refined living, this is a rare opportunity to own a truly special home in sought-after Weston.
Key Facts
- City/Town
- Weston
- Neighborhood
- Lower Weston
- Property / Style
- Single Family · Contemporary
- Year Built
- 1979
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 3 full
- Living Area
- 4,336 sq ft
- Lot Size
- 2.14 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $17,404 / Annually
Market Snapshot
The Weston Market
Single Family · trailing 12 months
Active Listings
37
16 under contract
Median List Price
$1.70M
37 active listings
Median Closed Price
$1.40M
130 sales
Median Days on Market
51
37 active listings
Median $ / Sq Ft
$383
37 active listings
Sale-to-List Ratio
101.5%
130 sales
How this home compares
List Price
$1.25M
vs $1.70M median
26.3% below median
Price / Sq Ft
$288
vs $383 median
24.8% below median
Days on Market
0 days
vs 51 days median
51 days fresher than median
Based on 37 active and 130 closed sales (trailing 12 mo) of single family in Weston. Source: SmartMLS · As of August 28, 2026.
Location
21 Deepwood Road, Weston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 27, 2026per month
- Principal & Interest$6,421
- Property Taxes$1,450
- Insurance$416
- 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
- 1979
- New Construction
- No/Resale
- Living Area
- 4,336 sq ft
Schools
- Elementary
- Hurlbutt
- High
- Weston
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main LevelUpper Level
- Appliances
- Cook TopOven/RangeRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullHeatedFully FinishedGarage AccessWalk-outFull With Walk-Out
- In-Law Apartment
- PossibleLower Level
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 2.14 acres
- Zoning
- R
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- Yes
- Construction
- Cedar
- Roof
- Asphalt Shingle
- Foundation
- Block
- Lot Description
- On Cul-De-SacWater View
Listing & Financials
- Property Taxes
- $17,404 / Annually
- Days on Market
- 0
- MLS #
- 24202535
- MLS Status
- Active
Similar Properties
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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 8/28/2026. 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 8/28/2026 at 5:20 PM UTC.