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21 Deepwood Road, Weston CT 06883
21 Deepwood Road, Weston CT 06883
Connecticut>Fairfield County>Weston

21 Deepwood RoadWeston, CT 06883

For Sale

$1,299,000

Smart Buyer Rebate $12,990

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.

Listed by Colby Gee

·

Real Broker CT

·

(607) 351-1527

Last updated July 30, 2026

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Source: SmartMLS #24190123

Listing Facts

  • TypeSingle-family
  • NeighborhoodWeston
  • Bedrooms5
  • Bathrooms3
  • Days on Prevu24
  • Taxes$17,404/year
  • Size5,671 sqft
  • Price per sqft$229

Location

Mortgage Calculator

Listing History

07/24/2026
Price Decreased
$1,299,000
07/20/2026
Status changed to Active
$1,325,000
07/19/2026
Status changed to Removed from Feed
$1,325,000
07/12/2026
Status changed to Active
$1,325,000
07/08/2026
Listed by Real Broker CT
$1,325,000

Property Details for 21 Deepwood Road

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1979
  • Year Built Details: Public Records
  • Architectural Style: Contemporary
  • Construction Materials: Frame
  • Exterior Features: Balcony, Deck, Patio

Features

  • Waterfront Features: Brook

Measurements

  • Lot Features: On Cul-De-Sac, Water View
  • Lot Size Acres: 2.14

Financial

Taxes

  • Parcel Number: 404619
  • Tax Annual Amount: $17,404.00
  • Tax Year: 25

Interior

Features

  • Appliances: Cook Top, Oven/Range, Refrigerator, Subzero, Dishwasher, Washer, Dryer
  • Fireplaces Total: 2

Measurements

  • Living Area: 4,336

Rooms

  • Basement: Full, Heated, Fully Finished, Garage Access, Walk-out, Full With Walk-Out
  • Bathrooms Full: 3
  • Bathrooms Total Integer: 3
  • Bedrooms Total: 5
  • Rooms Total: 12

Parking

Parking

  • Attached Garage: Attached Garage
  • Garage Spaces: 2

Schools

Elementary School

  • Elementary School: Hurlbutt

High School

  • High School: Weston

Middle or Junior School

  • Middle Or Junior School: Weston

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Hot Water
  • Laundry Features: Lower Level
  • Sewer: Septic
  • Water Source: Private Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 3 bathrooms in this single-family home at 21 Deepwood Road.

What schools are nearby to 21 Deepwood Road?

Nearby schools include the Hurlbutt Elementary School, Weston Middle School, and Weston High School.

Does this single-family home have parking?

Yes, there are 2 parking spaces available for 21 Deepwood Road.

What are the annual taxes for 21 Deepwood Road?

Annual taxes for this single-family home are estimated at $17,404.

How does 21 Deepwood Road compare to other single-family homes in Weston?

This single-family home is listed 29% below the average price for single-family homes in Weston and has been on the market for 48 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 5,671 sqft.

21 Deepwood Road is a 5-bedroom, 3-bath single-family home for sale in Weston CT 06883. Available on Prevu for 24 days at $1,299,000. This includes a recent price decrease of $26,000. This property features 5,671 square feet of living space, located in Weston. The median listing price for single-family homes in this area is $1,599,000. Nearby schools include Hurlbutt Elementary School, Weston Middle School, and Weston High School. Browse more single-family home listings in Fairfield County.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.