Tashna Bowes

21 Deepwood Road

Weston, CT
$ 1,249,000 Beds 5 Baths 3 Sq 4,336
Monthly Estimate* How much can I afford?

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.

Single Family

  • Price
  • $ 1,249,000
  • City
  • Weston
  • Bedrooms
  • 5
  • Full Bathrooms
  • 3
  • County
  • Fairfield
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 2.14 Acres
  • Zip
  • 06883
  • Sqr Footage
  • 4,336
  • Year Built
  • 1979
  • Taxes
  • $ 17404
  • Style
  • MLS#
  • 24202535
Listed By: Michael Spindler 347-419-2250 with Real Broker CT. - (413) 231-6114
Data Source: Smart MLS

Features

General

Zoning R
Neighborhood Lower Weston
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.14
Directions Left on Hill Farm to Deepwood. Down shared driveway to 21 Deepwood
High School Weston
City Weston
Elementary School Hurlbutt
Sq Ft Total 4336
DOM 23
Year Built 1979
Style Contemporary
Year Built Source Public Records
Energy Features Thermopane Windows

Interior Features

Cooling System Central Air
Total Rooms 12
Basement Description Full,Heated,Fully Finished,Garage Access,Walk-out,Full With Walk-Out

Exterior Features

Water Source Private Well
Lot Description On Cul-De-Sac,Water View

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Hurlbutt Elementary School
Middle School Unknown Middle School
High School Weston High School

Price History

8/28/2026 Listed $1,249,000

Property vs Zip Code Average in 06883

Price
AVG $1.86M
$1.25M
Taxes
AVG $22,074
$17,404
Year Built
AVG 1969
1979

In The Neighborhood

Areas That We Cover

21 Deepwood Road Weston, CT is a Single Family Home for sale at $1249000 with 4336 sqft and a lot size of 2.14 Acres Acre(s). 21 Deepwood Road Weston has 5 bedrooms, 3 baths and was built in 1979. The property's zip code is 06883 which is in Weston, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

Tashna Bowes

Tashna Bowes

347-698-0908

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