George Cress of Real Broker Email: george@cress.co (dot co) Call/Text: 212-203-5251
Weston, CT / 20 DAYS ON MARKET
21 Deepwood RoadWeston, CT 06883
Asking price$1,249,000Active
Open house
- Sunday, September 20, 202612:00 pm – 2:00 pm ET
Our Take
21 Deepwood Road in Weston sits at the end of a cul-de-sac on two acres overlooking a gently flowing brook. The five-bedroom, three-full-bath home includes two primary suites, with one on the main level and another upstairs with a private balcony. A kitchen with new countertops, contemporary bathroom finishes, and brand-new Andersen windows are among the described updates. The setting combines wooded surroundings with access to shops, restaurants, beaches, and a Metro-North station in neighboring Westport.
At a glance
Active · MLS #24202535- Bedrooms
- 5
- BathroomsBaths
- 3 full / 0 half
- Square feet
- 4,336
- Year built
- 1979
- Acres
- 2.14
- Property taxes
- $17,404
July 2025-June 2026
What stands out
- Two-acre cul-de-sac setting
- Overlooks a gently flowing brook
- Two primary suites on separate levels
- Upstairs primary suite with private balcony
- New countertops in the kitchen
- Contemporary bathroom finishes
- Brand-new Andersen windows throughout
Read the full listing description
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.
Schools
- Elementary
- Hurlbutt
- Middle
- Weston
- High
- Weston
Schools as reported by SmartMLS. Confirm attendance assignments with the district.
A closer look at the location
Open Google Maps ↗21 Deepwood Road, Weston, CT 06883
Price history
| Date | Event | Price |
|---|---|---|
| Originally listed | $1,249,000 |
Intermediate price changes and previous listings may not be included.
Could this be your next home?
Let’s talk about the property—and what working with Cress could save you.
*Estimate: $1,249,000 asking price × assumed 2.5% buyer-agent commission × 30% rebate = $9,368. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.
Listed by Real Broker CT · (413) 231-6114
Michael Spindler
SmartMLS · Listing #24202535 · Active
Listing data checked: Sep 17, 2026, 7:10 PM EDT.
Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.
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