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$1,325,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 5,671 Sq. Ft.
  • 2 Car Garage
  • Updated 7 hours ago

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Open House: 12:00 PM - 2:00 PM

Saturday 7/11 12:00 PM - 2:00 PM

21 Deepwood Road,Weston, CT 06883

21 Deepwood RoadWestonCT06883

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Join us at 21 Deepwood Road on:

  • Open House: 12:00 PM - 2:00 PM

    Sunday 7/12 12:00 PM - 2:00 PM

    21 Deepwood Road,Weston, CT 06883
    21 Deepwood RoadWestonCT06883
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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.

Full Property Details for 21 Deepwood Rd

General

  • Price: $1,325,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24190123
  • Updated: Today (7/11/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 12
  • Rooms/Areas: Bonus Room, Exercise Room
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Cook Top, Oven/Range, Refrigerator, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Bedroom Suite, Full Bath, Main
  • Primary Bedroom 2: Primary Bedroom - Balcony/Deck, Bedroom Suite, Full Bath, Sliders, Walk-In Closet, Upper
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Balcony/Deck, Fireplace, Main
  • Family Room: Family Room - Dry Bar, Fireplace, Patio/Terrace, Lower
  • Eat In Kitchen: Eat-In Kitchen, Main
  • Dining Room: Dining Room - Sliders, Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Engineered Wood Floor, Main
  • Rec Room: Engineered Wood Floor, Main
  • Laundry: Lower Level

Exterior

  • Exterior Features: Balcony, Deck, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Lower Weston
  • Driving Directions: Left on Hill Farm to Deepwood. Down shared driveway to 21 Deepwood

School Information

  • Elementary School: Hurlbutt
  • Middle School: Weston
  • High School: Weston

Community

  • Community Name: Lower Weston

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Upright Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Contemporary
  • Construction Status: No/Resale
  • Exterior Const.: Vertical Siding, Cedar
  • Basement Desc.: Full, Heated, Fully Finished, Garage Access, Walk-out, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 5,671
  • Above Ground: 4,124 Sq. Ft.
  • Below Ground: 1,547 Sq. Ft.
  • Year Built: 1979

Lot Features

  • Lot Size (Acres): 2.14
  • Zoning: R
  • Lot Description: On Cul-De-Sac, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Brook

Financial Considerations

  • Assessment Amount: $728,210
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Flood Zone: Yes
  • Property ID: 404619

Listed by Real Broker CT, Vantagepoint Properties at Real Broker, Colby Gee

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Listing agent

— 21 Deepwood Rd —

  • Colby Gee

    Real Broker CT

Agent Contact: (607) 351-1527 Office Contact: (413) 231-6114

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 21 Deepwood Rd

School District:Weston School District
NameGradesDistance
Weston Intermediate School
95 School Road, Weston, CT 06883
3-52 mi
Hurlbutt Elementary School
9 School Road, Weston, CT 06883
PK-22.4 mi
Weston Middle School
135 School Road, Weston, CT 06883
6-81.8 mi
Weston High School
115 School Road, Weston, CT 06883
9-121.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 21 Deepwood Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/11/2026
Listed
$1,325,000
50.57%
MLS
1/31/2026
Sold
$880,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 21 Deepwood Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$17,404
2%
$728,210
—
2023
$17,091
6%
$728,210
49%
2023
$16,152
—
$488,570
—
2022
$16,108
—
$488,570
—
2021
$16,084
2%
$488,570
—
2020
$15,815
—
$488,570
—
2019
$15,815
—
$488,570
-9%
2018
$15,797
2%
$537,500
—
2017
$15,539
1%
$537,500
—
2016
$15,351
—
$537,500
—
2015
$15,410
5%
$537,500
-12%
2011
$14,654
—
$613,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 21 Deepwood Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Real Broker CT, Vantagepoint Properties at Real Broker, Colby Gee

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21 Deepwood Road, Weston, CT 06883 (MLS# 24190123) is a Single Family property with 5 bedrooms and 3 full bathrooms. 21 Deepwood Road is currently listed for $1,325,000 and was received on July 11, 2026. Want to learn more about 21 Deepwood Road? Do you have questions about finding other Single Family real estate for sale in Weston? You can browse all Weston real estate or contact a Coldwell Banker agent to request more information.

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