Google street view image for 21 Deepwood Rd, Weston, CT 06883

Sold

$1,342,129

Est. refi paymentEst. refi $4,003/mo

•

3 ba

•

4,336

sq ft

21 Deepwood Rd, Weston, CT 06883

About this home

Spacious Contemp On 2 Priv Ac W/ Stream&Waterfall. Wonderful Spaces For Fam Liv. Designed For Tranquil Setting,There Are Walls Of Glass W/Many Drs To Wrap-Around Deck Overlooking Stream. Indoor/Outdoor Living At Its Best!

Single-familyProperty Type

1979Year Built

2.14 acresLot Size

$310Est. Price/Sq.Ft.

2 car garageParking

Source:Public Records

Redfin Estimate

$1,342,129

$587K since sold in April 2005$60K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 3.1% lower than the average sale price ($1.39M) of 6 comparable homes.

SOLD SEP 11, 2026
$1,700,000
A
5 beds3.5 baths4,476 sq ft
59 September Ln, Weston, CT 06883
SOLD AUG 18, 2026
$1,600,000
B
4 beds3.5 baths4,264 sq ft
38 Lords Hwy E, Weston, CT 06883
SOLD OCT 22, 2026
$950,000
C
6 beds3 baths3,096 sq ft
50 Ravenwood Dr, Weston, CT 06883
SOLD AUG 15, 2026
$1,170,000
D
5 beds4 baths4,344 sq ft
195 Steep Hill Rd, Weston, CT 06883
SOLD OCT 5, 2026
$1,680,000
E
4 beds3 baths3,621 sq ft
9 Autumn Ridge Rd, Weston, CT 06883
SOLD JUN 15, 2026
$1,213,000
F
5 beds2.5 baths4,092 sq ft
12 Mountain View Dr, Weston, CT 06883

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$1,263,006

Est. take-home

List your home with Redfin and save $13,421

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,232/mo

Redfin rental estimate

List your home for rent

Market trends in 06883, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

103.6%

2.4% MoM

Median sale price

$1.6M

$82K MoM

Avg. days on market

34d

5 days MoM

Recently sold homes

5 MoM

New listings for sale

OPEN SUN, 1PM TO 3PM
$1,585,000
4 beds4 baths2,512 sq ft
129 Davis Hill Rd, Weston, CT 06883
OPEN TODAY, 1PM TO 3PM
$1,850,000
4 beds5 baths4,202 sq ft
43 Kettle Creek Rd, Weston, CT 06883
OPEN SUN, 12PM TO 3PM
$1,495,000
5 beds3.5 baths4,728 sq ft
50 Catbrier Rd, Weston, CT 06883
$684,000
3 beds1.5 baths1,518 sq ft
494 Newtown Tpke, Weston, CT 06883
See all

Provided by Redfin

Sale history for 21 Deepwood Rd

Year

Property tax

Land + Additions

Assessment*

2023

$16,152 (+0.3%)

$192,920 + $295,650

$488,570

2022

$16,108 (+0.1%)

$192,920 + $295,650

$488,570

2021

$16,084 (+1.7%)

$192,920 + $295,650

$488,570

2020

$15,815

$192,920 + $295,650

$488,570

2019

$15,815 (+0.1%)

$192,920 + $295,650

$488,570

2018

$15,797 (+1.7%)

$192,900 + $344,600

$537,500

2017

$15,539 (+1.2%)

$192,900 + $344,600

$537,500

2016

$15,351 (+4.8%)

$192,900 + $344,600

$537,500

2013

$14,654

$254,700 + $358,700

$613,400

Tax history for 21 Deepwood Rd

Year

Property tax

Land + Additions

Assessment*

2023

$16,152 (+0.3%)

$192,920 + $295,650

$488,570

2022

$16,108 (+0.1%)

$192,920 + $295,650

$488,570

2021

$16,084 (+1.7%)

$192,920 + $295,650

$488,570

2020

$15,815

$192,920 + $295,650

$488,570

2019

$15,815 (+0.1%)

$192,920 + $295,650

$488,570

2018

$15,797 (+1.7%)

$192,900 + $344,600

$537,500

2017

$15,539 (+1.2%)

$192,900 + $344,600

$537,500

2016

$15,351 (+4.8%)

$192,900 + $344,600

$537,500

2013

$14,654

$254,700 + $358,700

$613,400

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

2.14 Acres

Year renovated

2007

Sq. Ft.

4,336

Year built

1979

Style

Single Family Residential

County

Fairfield County

APN

404619

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

Property details

Around this home

Schools

K - 12
Preschool & daycare

Weston Intermediate School

Public 3-5 • Assigned • 2.1mi

10/10

Weston Middle School

Public 6-8 • Assigned • 1.9mi

10/10

Weston High School

Public 9-12 • Assigned • 2.0mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Historical weather

Weston, CT • 06883

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

80/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

7.8 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.28M – $1.54M

Reach more buyers when you sell with Redfin. Save up to $13,421 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

OPEN SUN, 1PM TO 3PM

$1,585,000

4 beds4 baths2,512 sq ft

129 Davis Hill Rd, Weston, CT 06883

Hidden dry bar • Heated gunite pool • Bluestone patio

$925,000

2 beds2 baths1,135 sq ft

11 Judges Hollow Rd, Fairfield, CT 06824

Hilltop property • Private drive • Mature trees

OPEN SUN, 12PM TO 3PM

$4,450,000

6 beds7 baths8,594 sq ft

159 Easton Rd, Westport, CT 06880

Two acres • Aspetuck river • Finished space

OPEN SUN, 1PM TO 3PM

$1,449,900

6 beds5 baths4,348 sq ft

81 Trails End Rd, Weston, CT 06883

Private roof deck • Massive backyard • Picturesque pond

$1,249,000

4 beds3.5 baths2,958 sq ft

181 Georgetown Rd, Weston, CT 06883

Historic character • Modern comfort • Renovated baths

VIDEO TOUR

$4,695,000

5 beds4.5 baths7,907 sq ft

300 Sturges Ridge Rd, Wilton, CT 06897

Protected open space • Walls of glass • Soaring ceilings

New listings for sale in 06883

OPEN SUN, 1PM TO 3PM

$1,585,000

4 beds4 baths2,512 sq ft

129 Davis Hill Rd, Weston, CT 06883

Hidden dry bar • Heated gunite pool • Bluestone patio

OPEN TODAY, 1PM TO 3PM

$1,850,000

4 beds5 baths4,202 sq ft

43 Kettle Creek Rd, Weston, CT 06883

Nearly 5 acres • Swimming pool • Tennis court

OPEN SUN, 12PM TO 3PM3D WALKTHROUGH

$1,495,000

5 beds3.5 baths4,728 sq ft

50 Catbrier Rd, Weston, CT 06883

Renovated kitchen • Four season sunroom • Expansive deck

$684,000

3 beds1.5 baths1,518 sq ft

494 Newtown Tpke, Weston, CT 06883

New kitchen • Custom cabinetry • Brick fireplace

Home values near 21 Deepwood Rd

Data from public records.

Address	Redfin Estimate
22 Deepwood Road, Weston, CT 3 Beds \| 3 Baths \| 2708 Sq. Ft.	$1,214,362
15 Deepwood Road, Weston, CT 3 Beds \| 2.5 Baths \| 2820 Sq. Ft.	$1,112,709
20 Deepwood Road, Weston, CT 4 Beds \| 2.5 Baths \| 2184 Sq. Ft.	$726,648
3 Deepwood Road, Weston, CT 6 Beds \| 5 Baths \| 6566 Sq. Ft.	$2,313,136
26 Hill Farm Road, Weston, CT 6 Beds \| 4 Baths \| 3537 Sq. Ft.	$1,220,272
23 Hill Farm Road, Weston, CT 5 Beds \| 3 Baths \| 3516 Sq. Ft.	$1,316,222
16 Hill Farm Road, Weston, CT 4 Beds \| 4.5 Baths \| 5261 Sq. Ft.	$1,305,278

Address	Redfin Estimate
24 Deepwood Road, Weston, CT 3 Beds \| 3 Baths \| 2310 Sq. Ft.	$1,116,521
8 Deepwood Road, Weston, CT 3 Beds \| 2 Baths \| 3868 Sq. Ft.	$1,213,397
4 Deepwood Road, Weston, CT 3 Beds \| 2 Baths \| 2057 Sq. Ft.	$974,009
2 Deepwood Road, Weston, CT 4 Beds \| 5 Baths \| 7287 Sq. Ft.	$1,281,436
206 Steep Hill Road, Weston, CT 6 Beds \| 5.5 Baths \| 6469 Sq. Ft.	$1,824,198
198 Steep Hill Road, Weston, CT 5 Beds \| 4 Baths \| 3581 Sq. Ft.	$1,426,477
10 Tiffany Lane, Weston, CT 3 Beds \| 2 Baths \| 1318 Sq. Ft.	$925,718

Address	Redfin Estimate
9 Deepwood Road, Weston, CT 4 Beds \| 2.5 Baths \| 2928 Sq. Ft.	$1,293,169
12 Deepwood Road, Weston, CT 3 Beds \| 2 Baths \| 2136 Sq. Ft.	$1,130,068
17 Deepwood Road, Weston, CT 3 Beds \| 3 Baths \| 3616 Sq. Ft.	$840,176
24 Hill Farm Road, Weston, CT 4 Beds \| 3 Baths \| 1535 Sq. Ft.	$977,782
21 Hill Farm Road, Weston, CT 3 Beds \| 2.5 Baths \| 2052 Sq. Ft.	$997,841
22 Hill Farm Road, Weston, CT 3 Beds \| 3 Baths \| 2921 Sq. Ft.	$1,304,980
76 Davis Hill Road, Weston, CT 4 Beds \| 4.5 Baths \| 1456 Sq. Ft.	$1,247,848

More real estate resources

Cities
Neighborhoods
Minor Civil Divisions
Zip Codes
Popular Searches

Summit homes for sale
Princeton homes for sale
New York homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

Redfin Brokerage Licenses

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

East Brunswick Township homes for sale
Piscataway Township homes for sale
Livingston Township homes for sale
West Orange Township homes for sale
Millburn Township homes for sale

08873 homes for sale
08835 homes for sale
08844 homes for sale
08890 homes for sale

Houses for rent in Weston	Agents near me	Summit, NJ homes for sale	Weston Housing Market
Houses for sale near me	Jersey City, NJ homes for sale	Ridgewood, NJ homes for sale
Land for sale near me	Montclair, NJ homes for sale	Fort Lee, NJ homes for sale
Open Houses near me	Hoboken, NJ homes for sale	Weston Property Records
Condos for sale near me	Princeton, NJ homes for sale	CT New Listings