Google street view image for 108 Windy Hill Rd, Westbrook, CT 06498

Local rules require you to be signed in to see more photos.

Sold

$576,248

Est. refi paymentEst. refi $1,244/mo

•

2 ba

•

1,959

sq ft

108 Windy Hill Rd, Westbrook, CT 06498

About this home

Newly renovated cape on large lot, complete with fruit trees. Just steps to deeded water access. Open kitchen/living room with fireplace. First floor office/denwith built-ins. Owner/agent.

Single-familyProperty Type

1952Year Built

0.96 acresLot Size

$294Est. Price/Sq.Ft.

1 car garageParking

Source:Public Records

Redfin Estimate

$576,248

$261K since sold in December 2006$5,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 35% lower than the average sale price ($886K) of 6 comparable homes.

SOLD AUG 28, 2026
$580,000
A
3 beds2 baths1,800 sq ft
2 Half Penny Ln, Old Saybrook, CT 06475
SOLD AUG 14, 2026
$960,000
B
3 beds2 baths1,787 sq ft
3 Mohican Rd, Westbrook, CT 06498
SOLD OCT 1, 2026
$527,800
C
3 beds2 baths1,500 sq ft
106 Glenwood Rd, Clinton, CT 06413
SOLD AUG 4, 2026
$2,450,000
D
3 beds2 baths1,800 sq ft
47 Old Mail Trl, Westbrook, CT 06498
SOLD JUN 26, 2026
$400,000
E
3 beds2 baths1,281 sq ft
405 Pond Meadow Rd, Westbrook, CT 06498
SOLD SEP 16, 2026
$400,000
F
3 beds2 baths1,382 sq ft
17 Hunters Path, Clinton, CT 06413

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

Earn from this home

Sell

$541,087

Est. take-home

List your home with Redfin and save $5,762

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$2,423/mo

Redfin rental estimate

List your home for rent

Market trends in 06498, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

101.4%

2.0% MoM

Median sale price

$655K

$5K MoM

Avg. days on market

47d

16 days MoM

Recently sold homes

2 MoM

New listings for sale

FOR SALE BY OWNER
$560,000
4 beds2 baths1,922 sq ft
46 School Hill Ln, Westbrook, CT 06498
$1,375,000
4 beds2 baths1,954 sq ft
73 Chapman Beach Rd, Westbrook, CT 06498
$399,900
1 bed1.5 baths1,430 sq ft
159 Wrights Pond Rd, Westbrook, CT 06498
$740,000
3 beds3 baths2,355 sq ft
1340 Old Clinton Rd #10, Westbrook, CT 06498
$689,900
4 beds1.5 baths1,776 sq ft
84 Plymouth Rd, Westbrook, CT 06498
$1,195,000
4 beds2 baths1,593 sq ft
70 Old Mail Trl, Westbrook, CT 06498
See all

Provided by Redfin

Sale history for 108 Windy Hill Rd

Join or sign in to view all info

Year

Property tax

Land + Additions

Assessment*

2023

$5,122 (+2.7%)

$92,270 + $147,970

$240,240

2022

$4,987 (+3.4%)

$92,270 + $147,970

$240,240

2021

$4,821

$57,860 + $134,970

$192,830

2020

$4,821 (+1.3%)

$57,860 + $134,970

$192,830

2019

$4,757 (+1.2%)

$57,860 + $134,970

$192,830

2018

$4,699

$57,860 + $134,970

$192,830

2017

$4,699 (+11.4%)

$57,860 + $134,970

$192,830

2016

$4,218 (+6.2%)

$51,430 + $130,860

$182,290

2014

$3,972 (+5.5%)

$51,430 + $130,860

$182,290

2011

$3,765

$51,430 + $128,030

$179,460

Tax history for 108 Windy Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,122 (+2.7%)

$92,270 + $147,970

$240,240

2022

$4,987 (+3.4%)

$92,270 + $147,970

$240,240

2021

$4,821

$57,860 + $134,970

$192,830

2020

$4,821 (+1.3%)

$57,860 + $134,970

$192,830

2019

$4,757 (+1.2%)

$57,860 + $134,970

$192,830

2018

$4,699

$57,860 + $134,970

$192,830

2017

$4,699 (+11.4%)

$57,860 + $134,970

$192,830

2016

$4,218 (+6.2%)

$51,430 + $130,860

$182,290

2014

$3,972 (+5.5%)

$51,430 + $130,860

$182,290

2011

$3,765

$51,430 + $128,030

$179,460

*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

0.96 Acres

Year renovated

—

Sq. Ft.

1,959

Year built

1952

Style

Single Family Residential

County

Middlesex County

APN

1038664

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Around this home

Schools

K - 12
Preschool & daycare

Daisy Ingraham School

Public PreK-5 • Assigned • 1.1mi

8/10

Westbrook Middle School

Public 6-8 • Assigned • 1.2mi

10/10

Westbrook High School

Public 9-12 • Assigned • 1.5mi

7/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

6/10 Heat Factor

7 days above 93° expected this year, 18 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 days in 30 years

Provided by First Street

Historical weather

Westbrook, CT • 06498

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 9 hours in June and 4.6 hours in December, which is comparable to the U.S. average for solar exposure.

9 hrs

4.6 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$548,000 – $663,000

Reach more buyers when you sell with Redfin. Save up to $5,762 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

$429,000

2 beds1 bath960 sq ft

28 Bluff Ave, Clinton, CT 06413

Updated kitchen • Spacious island • Fenced in backyard

SHORT SALE

$349,000

3 beds1 bath1,172 sq ft

513 Essex Rd, Westbrook, CT 06498

0.52 acre lot • Garage • Built 1967

$12,000,000

4 beds1 bath2,059 sq ft

1445 Boston Post Rd, Old Saybrook, CT 06475

Bushnell farm house • Mature landscaping • Stone walls

$220,000

2 beds1.5 baths1,056 sq ft

40 Beach Rd, Clinton, CT 06413

Beach rights • Extensive renovation • Prime location

$115,000

2 beds1 bath672 sq ft

5 Cook Ter, Westbrook, CT 06498

New kitchen • Renovated bathroom • Carefree shed

$2,400,000

8 beds3 baths2,709 sq ft

127 Shore Rd, Clinton, CT 06413

Recently updated • 8,276 sq ft lot • 4 parking spots

New listings for sale in 06498

FOR SALE BY OWNER

$560,000

4 beds2 baths1,922 sq ft

46 School Hill Ln, Westbrook, CT 06498

Raised ranch • Hardwood floors • Corian countertops

$1,375,000

4 beds2 baths1,954 sq ft

73 Chapman Beach Rd, Westbrook, CT 06498

Custom patio • Private yard • Outdoor shower

$399,900

1 bed1.5 baths1,430 sq ft

159 Wrights Pond Rd, Westbrook, CT 06498

Private acres • Hardwood floors • Open floor plan

$740,000

3 beds3 baths2,355 sq ft

1340 Old Clinton Rd #10, Westbrook, CT 06498

Cul de sac • Large private deck • Remodeled kitchen

$689,900

4 beds1.5 baths1,776 sq ft

84 Plymouth Rd, Westbrook, CT 06498

Remodeled kitchen • Granite countertops • French doors

$1,195,000

4 beds2 baths1,593 sq ft

70 Old Mail Trl, Westbrook, CT 06498

Renovated beach home • Beach rights • Gorgeous new kitchen

Home values near 108 Windy Hill Rd

Data from public records.

Address	Redfin Estimate
24 Windy Hill Drive, Westbrook, CT 3 Beds \| 2 Baths \| 1834 Sq. Ft.	$573,822
122 Windy Hill Road, Westbrook, CT 2 Beds \| 1.5 Baths \| 1219 Sq. Ft.	$488,377
86 Windy Hill Road, Westbrook, CT 2 Beds \| 1 Baths \| 900 Sq. Ft.	$400,282
16 Windy Hill Drive, Westbrook, CT 3 Beds \| 2 Baths \| 1288 Sq. Ft.	$516,666
58 Meadowbrook Road, Westbrook, CT 2 Beds \| 2 Baths \| 1522 Sq. Ft.	$488,788
61 Lookout Road, Westbrook, CT 4 Beds \| 3 Baths \| 3880 Sq. Ft.	$1,185,130
78 Meadowbrook Road, Westbrook, CT 3 Beds \| 1.5 Baths \| 1289 Sq. Ft.	$359,514

Address	Redfin Estimate
77 Windy Hill Road, Westbrook, CT 2 Beds \| 1 Baths \| 960 Sq. Ft.	$417,212
123 Windy Hill Road, Westbrook, CT 3 Beds \| 3 Baths \| 2498 Sq. Ft.	$879,947
103 Windy Hill Road, Westbrook, CT 3 Beds \| 1 Baths \| 1450 Sq. Ft.	$442,847
63 Windy Hill Road, Westbrook, CT 4 Beds \| 2.5 Baths \| 1890 Sq. Ft.	$490,093
3 Lookout Road, Westbrook, CT 3 Beds \| 2 Baths \| 2304 Sq. Ft.	$791,150
37 Lookout Road, Westbrook, CT 4 Beds \| 2 Baths \| 1337 Sq. Ft.	$635,822
32 Lookout Road, Westbrook, CT 3 Beds \| 2.5 Baths \| 1392 Sq. Ft.	$523,521

Address	Redfin Estimate
91 Windy Hill Road, Westbrook, CT 2 Beds \| 2 Baths \| 1464 Sq. Ft.	$476,842
72 Windy Hill Road, Westbrook, CT 3 Beds \| 2 Baths \| 1720 Sq. Ft.	$543,912
23 Windy Hill Drive, Westbrook, CT 4 Beds \| 1.5 Baths \| 1818 Sq. Ft.	$608,227
15 Lookout Road, Westbrook, CT 2 Beds \| 2 Baths \| 1503 Sq. Ft.	$535,036
1 Lookout Road, Westbrook, CT 3 Beds \| 2.5 Baths \| 2700 Sq. Ft.	$834,930
92 Meadowbrook Road, Westbrook, CT 3 Beds \| 2.5 Baths \| 2092 Sq. Ft.	$1,212,290
62 Lookout Road, Westbrook, CT 3 Beds \| 1 Baths \| 1503 Sq. Ft.	$443,679

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.

Guilford homes for sale
Old Saybrook homes for sale
Wallingford homes for sale
Madison homes for sale
Branford homes for sale

Houses for rent in Westbrook Center	Agents near me	Westport, CT homes for sale	Westbrook Center Housing Market
Houses for sale near me	Greenwich, CT homes for sale	New Haven, CT homes for sale
Land for sale near me	Stamford, CT homes for sale	Milford, CT homes for sale
Open Houses near me	West Hartford, CT homes for sale	Westbrook Center Property Records
Condos for sale near me	Norwalk, CT homes for sale	CT New Listings

108 Windy Hill Rd, Westbrook, CT 06498

About this home

Redfin Estimate

Earn from this home

Market trends in 06498, CT

Sale history for 108 Windy Hill Rd

Tax history for 108 Windy Hill Rd

Public record

Property details

Public facts

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06498

Home values near 108 Windy Hill Rd

More real estate resources

Clinton homes for sale
Waterford homes for sale
Middletown homes for sale