21 Deepwood Road Weston, CT $ 1,249,000
21 Deepwood Road
$ 1,249,000
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21 Deepwood Road

Weston, CT, 06883
$ 1,249,000
Bedrooms5 Baths3.0 Sq 4,336

Monthly Estimate*

$ 7,886

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Single Family Home for sale in Weston, CT

for $1,249,000 with 5 bedrooms and 3 full baths. This 4,336 square foot home was built in 1979 on a lot size of 2.14.

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.

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Single Family Active

Price

$ 1,249,000

Bedrooms

5

Full Bath

3

Property Type

Single Family

Taxes

$ 17,404

Style

Lot Size

2.14

Year Built

1979

Town/City

Weston

MLS | Web ID

24202535

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 1
Year Built 1979
Style Contemporary
Year Built Source Public Records
Energy Features Thermopane Windows
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Interior
Cooling System Central Air
Total Rooms 12
Basement Description Full Heated Fully Finished Garage Access Walk-out Full With Walk-Out
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Exterior
Water Source Private Well
Lot Description On Cul-De-Sac Water View
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* Excluded Features
List By
Michael Spindler

Listing Agent

Real Broker Ct

Broker

mike@vantagepoint-properties.com

Email

Affordability Calculator

$9,337
Per Month
84%
16%
0%
Monthly Principal & Interest
$7,886
Monthly Property Taxes
$1,450
Monthly Home Insurance
--
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.
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Nearby
2060327 Elementary School
3041581 Middle School
Weston High School High School
Pricing History
DatePricePrice ChangeDescription
8/28/2026$1,249,000 Listed Price

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21 Deepwood Road, Weston, CT, 06883 is a Single Family Home for sale at $1,249,000 with 4,336 sqft and a lot size of 2.14. 21 Deepwood Road has 5 bedrooms, 3.0 baths, and was built in 1979. The property's zip code is 06883 which is in Weston, CT