Google street view image for 91 Tradewinds Rd, Oak Bluffs, MA 02557

Off market feb 2004 for $392K

$1,049,839

Est. refi paymentEst. refi $2,571/mo

•

1.5 ba

•

1,536

sq ft

91 Tradewinds Rd, Oak Bluffs, MA 02557

About this home

91 Tradewinds Rd is a 1,536 square foot house on a 0.37 acre lot with 1 bedroom and 1.5 bathrooms. - it last sold on February 17, 2004 for $392,000. Based on Redfin's Oak Bluffs data, we estimate the home's value is $1,049,839.

Single-familyProperty Type

1980Year Built

0.37 acresLot Size

$683Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,049,839

$658K since sold in February 2004$27K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 12.7% lower than the average sale price ($1.20M) of 6 comparable homes.

SOLD SEP 2, 2026
$905,000
A
2 beds1 bath1,074 sq ft
22 Firehouse, Oak Bluffs, MA 02557
SOLD SEP 15, 2026
$1,188,000
B
3 beds2 baths1,164 sq ft
3 Kims Way, Oak Bluffs, MA 02557
SOLD OCT 28, 2026
$1,080,000
C
3 beds2 baths1,373 sq ft
72 Moonstone Way, Vineyard Haven, MA 02568
SOLD OCT 8, 2026
$1,296,000
D
3 beds2 baths908 sq ft
66 Hudson Avenue Avenue, Oak Bluffs, MA 02557
SOLD SEP 18, 2026
$1,250,000
E
3 beds1.5 baths1,144 sq ft
82 Pennsylvania Ave, Oak Bluffs, MA 02557
SOLD OCT 1, 2026
$1,500,000
F
3 beds2 baths1,560 sq ft
9 Martha's Rd, Edgartown, MA 02539

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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 91 Tradewinds Rd

Year

Property tax

Land + Additions

Assessment*

2023

$3,888 (+1.1%)

$440,600 + $295,700

$736,300

2022

$3,847 (+5.9%)

$331,900 + $234,600

$566,500

2021

$3,632 (+5.0%)

$288,000 + $204,800

$492,800

2020

$3,459 (+7.2%)

$274,300 + $190,600

$464,900

2019

$3,227 (+4.5%)

$239,200 + $180,500

$419,700

2018

$3,089 (+4.6%)

$216,000 + $178,500

$394,500

2017

$2,954 (+7.1%)

$204,800 + $157,600

$362,400

2016

$2,758 (+5.1%)

$211,100 + $129,000

$340,100

2015

$2,624

$211,100 + $118,600

$329,700

Tax history for 91 Tradewinds Rd

Year

Property tax

Land + Additions

Assessment*

2023

$3,888 (+1.1%)

$440,600 + $295,700

$736,300

2022

$3,847 (+5.9%)

$331,900 + $234,600

$566,500

2021

$3,632 (+5.0%)

$288,000 + $204,800

$492,800

2020

$3,459 (+7.2%)

$274,300 + $190,600

$464,900

2019

$3,227 (+4.5%)

$239,200 + $180,500

$419,700

2018

$3,089 (+4.6%)

$216,000 + $178,500

$394,500

2017

$2,954 (+7.1%)

$204,800 + $157,600

$362,400

2016

$2,758 (+5.1%)

$211,100 + $129,000

$340,100

2015

$2,624

$211,100 + $118,600

$329,700

*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: 1
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Air

Exterior

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

Property Information
Living Sq. Ft: 1,536
Gross Sq. Ft: 2,642
# of Units: 1
# of Stories: 1

Lot Information
# of Buildings: 1
Land Sq. Ft: 16,117
Municipality Name: OAK BLUFFS
Acres: 0.37
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 1
Baths: 1.5
Sq. Ft.: 1,536
Stories: 1.0
Lot Size: 0.37 acres
Style: Single Family Residential
Year Built: 1980
Year Renovated: 1993
County: Dukes County
APN: 3877513

Home facts updated by county records on Jan 30, 2023

Around this home

Schools

K - 12
Preschool & daycare

Oak Bluffs Elementary School

Public PreK-8 • Assigned • 0.3mi

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

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

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

$998,000 – $1.21M

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

Nearby similar homes

$5,750,000

6 beds6.5 baths5,424 sq ft

41 Hagerty Dr, Vineyard Haven, MA 02568

Custom cabinetry • Oversized island • Inviting home office

$1,399,000

3 beds2.5 baths1,645 sq ft

7 Ploughshare Ln, Oak Bluffs, MA 02557

Cul-de-sac • Open floor plan • Cozy fireplace

$1,570,000

3 beds2.5 baths2,347 sq ft

41 & 0 Cook Rd, Vineyard Haven, MA 02568

Buildable lot • Custom kitchen • Walk-in pantry

$1,745,000

2 beds1 bath561 sq ft

11 Beach Rd, Oak Bluffs, MA 02557

Oceanfront cottage • Waterfront property • Eat-in kitchen

OPEN SUN, 1PM TO 3PM

$1,195,000

3 beds1.5 baths912 sq ft

11 Stanley St, Oak Bluffs, MA 02557

Cul-de-sac • Spacious lot • Recent upgrades

$1,095,000

1 bed2 baths1,428 sq ft

323 County Rd, Oak Bluffs, MA 02557

First floor den • Spacious deck • Outdoor shower

Home values near 91 Tradewinds Rd

Data from public records.

Address	Redfin Estimate
107 Tradewinds Road, Oak Bluffs, MA 2 Beds \| 1 Baths \| 1075 Sq. Ft.	$904,050
71 Tradewinds Road, Oak Bluffs, MA 3 Beds \| 3 Baths \| 1418 Sq. Ft.	$1,353,926
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
24 Pinewood Lane, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1310 Sq. Ft.	$1,277,043
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
101 Tradewinds Road, Oak Bluffs, MA 3 Beds \| 1.5 Baths \| 1456 Sq. Ft.	$1,358,510
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
32 Lower Douglas Lane, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1008 Sq. Ft.	$1,009,511
255 County Road, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1990 Sq. Ft.	$1,063,518
15 Pinewood Lane, Oak Bluffs, MA 2 Beds \| 1 Baths \| 1184 Sq. Ft.	$1,017,198

Address	Redfin Estimate
95 Tradewinds Road, Oak Bluffs, MA 5 Beds \| 2 Baths \| 1590 Sq. Ft.	$986,161
75 Tradewinds Road, Oak Bluffs, MA 2 Beds \| 2 Baths \| 1310 Sq. Ft.	$1,026,464
242 County Road, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1280 Sq. Ft.	$872,172
3 Hudson Avenue, Oak Bluffs, MA 3 Beds \| 2 Baths \| 985 Sq. Ft.	—
18 Pinewood Lane, Oak Bluffs, MA 3 Beds \| 1.5 Baths \| 1142 Sq. Ft.	$1,184,820
238 County Road, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1156 Sq. Ft.	$856,883
5 Pinewood Lane, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1872 Sq. Ft.	$1,363,849

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