Google street view image for 75 Tradewinds Rd, Oak Bluffs, MA 02557

Off market oct 1998 for $179K

$1,026,464

Est. refi paymentEst. refi $880/mo

•

2 ba

•

1,310

sq ft

75 Tradewinds Rd, Oak Bluffs, MA 02557

About this home

75 Tradewinds Rd is a 1,310 square foot house on a 0.29 acre lot with 2 bedrooms and 2 bathrooms. - it last sold on October 22, 1998 for $179,000. Based on Redfin's Oak Bluffs data, we estimate the home's value is $1,026,464.

Single-familyProperty Type

1981Year Built

0.29 acresLot Size

$784Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,026,464

$847K since sold in October 1998$65K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 5.5% lower than the average sale price ($1.09M) of 6 comparable homes.

SOLD SEP 15, 2026
$1,188,000
A
3 beds2 baths1,164 sq ft
3 Kims Way, Oak Bluffs, MA 02557
SOLD SEP 2, 2026
$905,000
B
2 beds1 bath1,074 sq ft
22 Firehouse, Oak Bluffs, MA 02557
SOLD OCT 8, 2026
$1,296,000
C
3 beds2 baths908 sq ft
66 Hudson Avenue Avenue, Oak Bluffs, MA 02557
SOLD OCT 28, 2026
$1,080,000
D
3 beds2 baths1,373 sq ft
72 Moonstone Way, Vineyard Haven, MA 02568
SOLD JUN 4, 2026
$800,000
E
3 beds2 baths1,152 sq ft
17 Mariner Rd, Vineyard Haven, MA 02568
SOLD SEP 18, 2026
$1,250,000
F
3 beds1.5 baths1,144 sq ft
82 Pennsylvania Ave, Oak Bluffs, MA 02557

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Refinance

Est. cash available

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Market trends in 02568, MA

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

94.6%

0.4% MoM

Median sale price

$1.3M

$130K MoM

Avg. days on market

85d

2 days MoM

Recently sold homes

0 MoM

Provided by Redfin

Sale history for 75 Tradewinds Rd

Year

Property tax

Land + Additions

Assessment*

2023

$433,300 + $429,100

$862,400

2022

$326,300 + $321,500

$647,800

2021

$4,130 (+5.2%)

$281,900 + $278,500

$560,400

2020

$3,924 (+4.6%)

$268,500 + $258,900

$527,400

2019

$3,753 (+2.8%)

$234,100 + $254,000

$488,100

2018

$3,651 (+6.0%)

$211,400 + $254,900

$466,300

2017

$3,445 (+6.8%)

$200,400 + $222,300

$422,700

2016

$3,225 (+5.6%)

$206,600 + $191,000

$397,600

2015

$3,055

$206,600 + $177,200

$383,800

Tax history for 75 Tradewinds Rd

Year

Property tax

Land + Additions

Assessment*

2023

$433,300 + $429,100

$862,400

2022

$326,300 + $321,500

$647,800

2021

$4,130 (+5.2%)

$281,900 + $278,500

$560,400

2020

$3,924 (+4.6%)

$268,500 + $258,900

$527,400

2019

$3,753 (+2.8%)

$234,100 + $254,000

$488,100

2018

$3,651 (+6.0%)

$211,400 + $254,900

$466,300

2017

$3,445 (+6.8%)

$200,400 + $222,300

$422,700

2016

$3,225 (+5.6%)

$206,600 + $191,000

$397,600

2015

$3,055

$206,600 + $177,200

$383,800

*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: Forced Hot Water

Exterior

Exterior Information
Physical Condition: Average
Building Style Type: Cape Cod
Construction Type: Frame
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 1,310
Gross Sq. Ft: 3,493
# of Units: 1
# of Stories: 1

Lot Information
# of Buildings: 1
Land Sq. Ft: 12,632
Municipality Name: OAK BLUFFS
Acres: 0.29
State Use Description: MIXED USE-PRIM RES & COMM

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 1,310
Stories: 1.0
Lot Size: 0.29 acres
Style: Single Family Residential
Year Built: 1981
Year Renovated: 1998
County: Dukes County
APN: 3877509

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 • 0.2mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 2.2mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

Flood Factor

We're working on getting current and accurate flood risk information for this home.

Fire Factor

We're working on getting current and accurate fire risk information for this home.

4/10 Heat Factor

7 hot days expected this year, 19 days in 30 years

Wind Factor

We're working on getting current and accurate wind risk information for this home.

2/10 Air Factor

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

Provided by First Street

Historical weather

Oak Bluffs, MA • 02557

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 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

$976,000 – $1.18M

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Nearby similar homes

$1,200,000

4 beds3 baths2,304 sq ft

33 Alyssa Ln, Vineyard Haven, MA 02568

Large side deck • High ceilings • Wood floors

$1,100,000

3 beds2 baths1,302 sq ft

47 Winemack St, Oak Bluffs, MA 02557

Open floor plan • Recent upgrades • New roofs

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

$875,000

3 beds1.5 baths2,208 sq ft

74 Chase Lane & 25 Norton Ave, Vineyard Haven, MA 02568

Cape cod style • New roof • New windows

$6,150,000

6 beds6 baths5,034 sq ft

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Exceptional privacy • Open-concept layout • Bluestone patio

$549,000

Land— sq ft

112 Dukes County, Oak Bluffs, MA 02557

Three rentable units • Listed 250 days

Home values near 75 Tradewinds Rd

Data from public records.

Address	Redfin Estimate
61 Tradewinds Road, Oak Bluffs, MA 2 Beds \| 1.5 Baths \| 768 Sq. Ft.	$1,012,553
71 Tradewinds Road, Oak Bluffs, MA 3 Beds \| 3 Baths \| 1418 Sq. Ft.	$1,353,926
91 Tradewinds Road, Oak Bluffs, MA 1 Beds \| 1.5 Baths \| 1536 Sq. Ft.	$1,049,839
38 Pinewood Lane, Oak Bluffs, MA 3 Beds \| 3 Baths \| 954 Sq. Ft.	$989,391
24 Pinewood Lane, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1310 Sq. Ft.	$1,277,043
18 Pinewood Lane, Oak Bluffs, MA 3 Beds \| 1.5 Baths \| 1142 Sq. Ft.	$1,184,820
39 Pinewood Lane, Oak Bluffs, MA 3 Beds \| 3 Baths \| 2714 Sq. Ft.	$1,684,837

Address	Redfin Estimate
67 Tradewinds Road, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1470 Sq. Ft.	$1,188,519
63 Tradewinds Road, Oak Bluffs, MA 2 Beds \| 1.5 Baths \| 1350 Sq. Ft.	$1,099,463
89 Tradewinds Road, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1512 Sq. Ft.	$1,261,599
39 Lower Douglas Lane, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1632 Sq. Ft.	$955,182
32 Lower Douglas Lane, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1008 Sq. Ft.	$1,009,511
25 Pinewood Lane, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1547 Sq. Ft.	$1,187,505
19 Pinewood Lane, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1839 Sq. Ft.	$1,395,113

Address	Redfin Estimate
95 Tradewinds Road, Oak Bluffs, MA 5 Beds \| 2 Baths \| 1590 Sq. Ft.	$986,161
79 Tradewinds Road, Oak Bluffs, MA 2 Beds \| 1 Baths \| 576 Sq. Ft.	$764,397
83 Tradewinds Road, Oak Bluffs, MA 3 Beds \| 1.5 Baths \| 1165 Sq. Ft.	$1,100,019
31 Lower Douglas Lane, Oak Bluffs, MA 4 Beds \| 4 Baths \| 2880 Sq. Ft.	$1,180,154
7 Spargo Lane, Vineyard Haven, MA 1 Beds \| 1 Baths \| 1257 Sq. Ft.	$1,373,361
29 Pinewood Lane, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1547 Sq. Ft.	$1,313,651
15 Pinewood Lane, Oak Bluffs, MA 2 Beds \| 1 Baths \| 1184 Sq. Ft.	$1,017,198

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