Google satellite image for 32 Windy Hill Rd, Oak Bluffs, MA 02557

Off market feb 2004 for $375K

$1,245,483

Est. refi paymentEst. refi $2,308/mo

•

2 ba

•

1,687

sq ft

32 Windy Hill Rd, Oak Bluffs, MA 02557

About this home

32 Windy Hill Rd is a 1,687 square foot house on a 0.5 acre lot with 4 bedrooms and 2 bathrooms. - it last sold on February 27, 2004 for $375,000. Based on Redfin's Oak Bluffs data, we estimate the home's value is $1,245,483.

Single-familyProperty Type

1968Year Built

0.5 acresLot Size

$738Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,245,483

$870K since sold in February 2004$45K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 3.6% lower than the average sale price ($1.29M) of 6 comparable homes.

SOLD SEP 11, 2026
$1,050,000
A
4 beds2 baths1,513 sq ft
1 Dodgers Hole Rd, Edgartown, MA 02539
SOLD OCT 23, 2026
$1,600,000
B
4 beds2 baths1,342 sq ft
58 Road To The Plns, Edgartown, MA 02539
SOLD JUN 12, 2026
$1,187,500
C
4 beds2 baths1,764 sq ft
54 Columbian, Oak Bluffs, MA 02557
SOLD SEP 15, 2026
$1,188,000
D
3 beds2 baths1,164 sq ft
3 Kims Way, Oak Bluffs, MA 02557
SOLD MAR 16, 2026
$1,225,000
E
4 beds2 baths1,566 sq ft
344 Greenwood Ave, Vineyard Haven, MA 02568
SOLD OCT 1, 2026
$1,500,000
F
3 beds2 baths1,560 sq ft
9 Martha's Rd, Edgartown, MA 02539

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

Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Market trends in 02568, MA

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

95.3%

+0.8% MoM

Median sale price

$1.4M

$59K MoM

Avg. days on market

70d

15 days MoM

Recently sold homes

9 MoM

Provided by Redfin

Sale history for 32 Windy Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,441 (+0.7%)

$449,800 + $391,300

$841,100

2022

$4,410 (+5.8%)

$338,800 + $310,700

$649,500

2021

$4,167 (+5.3%)

$295,500 + $269,900

$565,400

2020

$3,957 (+4.8%)

$281,400 + $250,500

$531,900

2019

$3,777 (+3.2%)

$245,400 + $245,700

$491,100

2018

$3,661 (+5.5%)

$221,600 + $246,000

$467,600

2017

$3,471 (+11.1%)

$210,100 + $215,800

$425,900

2016

$3,123 (+5.7%)

$216,600 + $168,500

$385,100

2015

$2,954

$216,600 + $154,500

$371,100

Tax history for 32 Windy Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$4,441 (+0.7%)

$449,800 + $391,300

$841,100

2022

$4,410 (+5.8%)

$338,800 + $310,700

$649,500

2021

$4,167 (+5.3%)

$295,500 + $269,900

$565,400

2020

$3,957 (+4.8%)

$281,400 + $250,500

$531,900

2019

$3,777 (+3.2%)

$245,400 + $245,700

$491,100

2018

$3,661 (+5.5%)

$221,600 + $246,000

$467,600

2017

$3,471 (+11.1%)

$210,100 + $215,800

$425,900

2016

$3,123 (+5.7%)

$216,600 + $168,500

$385,100

2015

$2,954

$216,600 + $154,500

$371,100

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

Property details

Interior

Bathroom Information
# of Full Baths: 2

Heating & Cooling
Heating Type: Baseboard

Room Information
# of Rooms: 6

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Ranch
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 1,687
Gross Sq. Ft: 2,639
# of Units: 1
# of Stories: 1

Lot Information
# of Buildings: 1
Land Sq. Ft: 21,780
Municipality Name: OAK BLUFFS
Acres: 0.5
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 1,687
Stories: 1.0
Lot Size: 0.5 acres
Style: Single Family Residential
Year Built: 1968
Year Renovated: 1998
County: Dukes County
APN: 3876532

Home facts updated by county records on Jul 19, 2023

Around this home

Schools

K - 12
Preschool & daycare

Oak Bluffs Elementary School

Public PreK-8 • Assigned • 0.4mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 2.6mi

6/10

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

4/10 Heat Factor

7 days above 88° expected this year, 19 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Oak Bluffs, MA • 02557

Average low and high temperatures (°F)

36°

24°

37°

24°

47°

34°

55°

41°

64°

51°

75°

59°

79°

65°

76°

59°

72°

57°

62°

50°

53°

40°

43°

29°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.5 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.18M – $1.43M

Sell confidently with a local market expert in Oak Bluffs. 3 minutes to get started.

Nearby similar homes

NEW 35 HRS AGO

$2,375,000

3 beds2.5 baths4,470 sq ft

149 Clover Hill Dr, Vineyard Haven, MA 02568

Three season sunroom • Finished bonus room • Walk up attic

OPEN NOV 17, 1PM TO 3PM

$2,095,000

4 beds4 baths2,876 sq ft

18 Sylvan Ave, Vineyard Haven, MA 02568

Wraparound deck • Finished lower level • Natural light

$2,850,000

4 beds3 baths2,927 sq ft

2 Bold Meadow Rd, Edgartown, MA 02539

Private parcel • Mature woodlands • Association land

$1,095,000

3 beds1 bath998 sq ft

299 Daggett Ave Unit A, Vineyard Haven, MA 02568

Cathedral ceilings • Mahogany deck • Koi pond

$785,000

2 beds1 bath624 sq ft

60R Carol Ln, Oak Bluffs, MA 02557

Open concept • Wrap-around deck • Outdoor shower

$6,150,000

6 beds6 baths5,034 sq ft

59 Hagerty Dr, Vineyard Haven, MA 02568

Exceptional privacy • Open-concept layout • Bluestone patio

Home values near 32 Windy Hill Rd

Data from public records.

Address	Redfin Estimate
28 Windy Hill Rd, Oak Bluffs, MA 3 Beds \| 1 Baths \| 960 Sq. Ft.	$934,091
25 Windy Hill Rd, Oak Bluffs, MA 3 Beds \| 1 Baths \| 960 Sq. Ft.	$908,491
19 Windy Hill Rd, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1612 Sq. Ft.	$1,271,938
16 Windy Hill Rd, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1120 Sq. Ft.	$1,030,862
50 Rogers Way, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1274 Sq. Ft.	$1,067,882
38 Rogers Way, Oak Bluffs, MA 3 Beds \| 2 Baths \| 2448 Sq. Ft.	$1,572,637
30 Inca Rd, Oak Bluffs, MA 4 Beds \| 3 Baths \| 1764 Sq. Ft.	$1,651,146

Address	Redfin Estimate
15 Windy Hill Rd, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1564 Sq. Ft.	$1,304,607
18 Windy Hill Rd, Oak Bluffs, MA 2 Beds \| 2.5 Baths \| 1714 Sq. Ft.	$1,575,380
22 Windy Hill Rd, Oak Bluffs, MA 3 Beds \| 1 Baths \| 1264 Sq. Ft.	$1,081,450
27 Inca Rd, Oak Bluffs, MA 2 Beds \| 2 Baths \| 1239 Sq. Ft.	$1,402,968
63 Rogers Way, Oak Bluffs, MA 3 Beds \| 2.5 Baths \| 3088 Sq. Ft.	$1,834,946
45 Rogers Way, Oak Bluffs, MA 3 Beds \| 3.5 Baths \| 1232 Sq. Ft.	$1,074,743
26 Inca Rd, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1568 Sq. Ft.	$1,443,080

Address	Redfin Estimate
21 Windy Hill Rd, Oak Bluffs, MA 3 Beds \| 1.5 Baths \| 888 Sq. Ft.	$924,542
20 Windy Hill Rd, Oak Bluffs, MA 4 Beds \| 1.5 Baths \| 1189 Sq. Ft.	$973,546
29 Windy Hill Rd, Oak Bluffs, MA 3 Beds \| 1 Baths \| 1008 Sq. Ft.	$971,656
81 Rogers Way, Oak Bluffs, MA 3 Beds \| 3.5 Baths \| 2764 Sq. Ft.	$2,044,514
25 Inca Rd, Oak Bluffs, MA 4 Beds \| 3.5 Baths \| 1943 Sq. Ft.	$1,648,361
24 Rogers Way, Oak Bluffs, MA 3 Beds \| 3.5 Baths \| 2666 Sq. Ft.	$2,048,974
71 Rogers Way, Oak Bluffs, MA 3 Beds \| 2.5 Baths \| 1736 Sq. Ft.	$1,574,158

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.

Houses for rent in Oak Bluffs	Agents near me	Quincy, MA homes for sale	Oak Bluffs Housing Market
Houses for sale near me	Boston, MA homes for sale	Brookline, MA homes for sale
Land for sale near me	Newton, MA homes for sale	Arlington, MA homes for sale
Open Houses near me	Cambridge, MA homes for sale	Oak Bluffs Property Records
Condos for sale near me	Lexington, MA homes for sale	MA New Listings

Sandwich homes for sale
Oak Bluffs homes for sale
Falmouth homes for sale

02568 homes for sale
02573 homes for sale
02557 homes for sale