21 Deepwood Rd

Weston, CT 06883

$1,325,000
Price
5
Beds
5,671 Sq. Ft.
$234 / Sq. Ft.
5,671
Sq. Ft.
$234
per Sq. Ft.
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Open: 7/12 12:00PM - 02:00PM
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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...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.
  1. Listed by Colby Gee • Real Broker CT
    P: (607)-351-1527 C: (607)-351-1527 Colbysellsct@gmail.com

Property Details for 21 Deepwood Road

Basement Description
Full, Heated, Fully Finished, Garage Access, Walk-out, Full With Walk-Out
Direct Waterfront
Yes
Expected Active Date
07-11-2026
Garages Number
2
Neighborhood
Lower Weston
Style
Contemporary
Garage Parking Info
Attached Garage
Swimming Pool
No

Open Houses

Sunday, Jul 12th12:00 PM - 2:00 PM
PublicView contact
LISTING UPDATED: 07/11/2026 11:40 PM

Property Details for 21 Deepwood Road

StatusActive
MLS #24190123
Days on Market1
Taxes$17,404 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1979
Lot Size2.14 AC / 93,218 SF
CountyFairfield County
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Location

Listing Courtesy of Real Broker CT, Colby Gee
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Building Information for 21 Deepwood Road

Stories-Year Built1979Building Size-Lot Size2.14 AC / 93,218 SF

Payment Calculator

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$8,053 per month

30 year fixed, 6.36% Interest

Principal and Interest

$6,603

Property Taxes

$1,450

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 21 Deepwood Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Left on Hill Farm to Deepwood. Down shared driveway to 21 Deepwood
  • Elementary School: Hurlbutt
  • Flood Zone: Yes
  • High School: Weston
  • Latitude: 41.231819
  • Longitude: -73.355168
  • Middle Jr High School: Weston
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $17,404
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Deck, Patio
  • Waterfront Description: Brook
Interior Features
  • Appliances Included: Cook Top, Oven/Range, Refrigerator, Subzero, Dishwasher, Washer, Dryer
  • Attic Description: Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Laundry Room Info: Lower Level
  • Laundry Room Location: Hook up for 2nd laundry in primary
  • Rooms Additional: Bonus Room, Exercise Room
  • Rooms Total: 12
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Balcony/Deck,Fireplace
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Dry Bar,Fireplace,Patio/Terrace
  • Room Level: Lower
  • Room Type: Family Room
Room 3
  • Room Entry Order: 2
  • Room Features: Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 4
  • Room Entry Order: 3
  • Room Features: Bedroom Suite,Full Bath
  • Room Level: Main
  • Room Type: Primary Bedroom
Room 5
  • Listing Key: 562380CC9127C420E063E201100AC289
  • Room Entry Order: 4
  • Room Features: Balcony/Deck,Bedroom Suite,Full Bath,Sliders,Walk-In Closet
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 6
  • Room Entry Order: 5
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 6
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 7
  • Room Level: Upper
  • Room Type: Bedroom
Room 9
  • Listing Key: 562380CC9127C420E063E201100AC289
  • Room Entry Order: 8
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 10
  • Room Entry Order: 9
  • Room Features: Engineered Wood Floor
  • Room Level: Main
  • Room Type: Rec/Play Room
Property
Property and Assessments
  • Construction Description: Frame
  • Elevation Certificate: No
  • Exterior Siding: Vertical Siding, Cedar
  • Foundation Type: Block
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1979
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level
  • In Law Apartment: Possible
  • Sq Ft Description: per floor plans
  • Sq Ft Est Heated Below Grade: 1547
  • Living Area SQFT Per Public Records: 4336
Lot Information
  • Lot Description: On Cul-De-Sac, Water View
  • Parcel Number: 404619
  • Sq Ft Est Heated Above Grade: 4124.0
  • Sq Ft Total: 5671.0
  • Zoning: R
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Upright Tank
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 21 Deepwood Road

DateEvent & SourcePriceAppreciation
Jan 31, 2026

Closed (Public Record)

Public Record #1931405936

$880,000

+0.7% / yr

Apr 11, 2005

Closed (Public Record)

Public Record #159297306

$755,000—
DateEvent & SourcePrice
01/31/2026

Closed (Public Record)

Public Record #1931405936

$880,000

+0.7% / yr

04/11/2005

Closed (Public Record)

Public Record #159297306

$755,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 21 Deepwood Road

Taxable ValueLand$192,920Additions$535,290Total$728,210
Tax Record2024$17,404 ($1,450 / month)
Home Facts
Beds5Baths3Total Finished SqFt4,336 SqFtAbove Grade Finished SqFt4,336 SqFtUnfinished Basement SqFt2,668 SqFtStories2Lot Size93,218 SqFtStyleSingle Family ResidenceYear Built1979Year Renovated2007ZoningRCountyWESTERN CONNECTICUTAPNWSTN M:16 B:2 L:26Fireplace TypeHas Fireplace

Schools near 21 Deepwood Road

This home is within Weston School District.
Rating
School
Type
Grades
Distance
Hurlbutt Elementary School
Public - PK to 2
Weston Intermediate School
Public - 3 to 5
Weston Middle School
Public - 6 to 8
Weston High School
Public - 9 to 12
Rating
School
Distance
Hurlbutt Elementary School
PublicPK to 2

Weston Intermediate School
Public3 to 5

Weston Middle School
Public6 to 8

Weston High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Weston
Weston
An inviting and peaceful town with lots of natural beauty. Home to just over 10,000 people, beautiful Weston delivers a bucolic atmosphere crisscrossed by woods, streams and rivers. Founded in 1787 as an agricultural community, a lack of railroad access buffered further commercial development....
Weston Guide

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More information about 21 Deepwood Road, Weston, CT 06883

21 Deepwood Road is a single family home for sale in Weston, CT 06883. This listing's school district is Weston School District. Nearby schools include Hurlbutt Elementary School, Weston Intermediate School and Weston Middle School. 21 Deepwood Road is a 5-bed, 3-bath, 5,671 sqft single family home built in 1979.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Real Broker CT, Colby Gee

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.