Google street view image for 36 Tradewinds Rd, Oak Bluffs, MA 02557

Off market jan 2003 for $475K

$1,471,285

Est. refi paymentEst. refi $3,076/mo

•

3 ba

•

2,072

sq ft

36 Tradewinds Rd, Oak Bluffs, MA 02557

About this home

36 Tradewinds Rd is a 2,072 square foot house on a 0.53 acre lot with 4 bedrooms and 3 bathrooms. - it last sold on January 09, 2003 for $475,000. Based on Redfin's Oak Bluffs data, we estimate the home's value is $1,471,285.

Single-familyProperty Type

1999Year Built

0.53 acresLot Size

$710Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,471,285

$996K since sold in January 2003$40K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 13.2% lower than the average sale price ($1.70M) of 6 comparable homes.

SOLD MAR 30, 2026
$1,500,000
A
4 beds3 baths1,975 sq ft
68 Twentieth Street South, Edgartown, MA 02539
SOLD OCT 23, 2026
$2,350,000
B
4 beds3 baths1,968 sq ft
105 Whalers Walk, Edgartown, MA 02539
SOLD JUL 29, 2026
$1,885,000
C
5 beds3.5 baths2,527 sq ft
18 Puritan Dr, Oak Bluffs, MA 02557
SOLD OCT 2, 2026
$2,200,000
D
4 beds4 baths2,288 sq ft
54 Amelia's Xing, Vineyard Haven, MA 02568
SOLD SEP 11, 2026
$1,050,000
E
4 beds2 baths1,513 sq ft
1 Dodgers Hole Rd, Edgartown, MA 02539
SOLD JUN 12, 2026
$1,187,500
F
4 beds2 baths1,764 sq ft
54 Columbian, Oak Bluffs, MA 02557

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Earn from this home

Refinance

Est. cash available

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Rent

$3,446/mo

Redfin rental estimate

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Market trends in Oak Bluffs, MA

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

95.5%

1.1% MoM

Median sale price

$1.2M

$49K MoM

Avg. days on market

75d

14 days MoM

Recently sold homes

2 MoM

Provided by Redfin

Sale history for 36 Tradewinds Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,221 (−3.1%)

$451,900 + $537,000

$988,900

2022

$5,387 (+1.9%)

$340,400 + $452,900

$793,300

2021

$5,287 (+5.6%)

$297,200 + $420,200

$717,400

2020

$5,007 (+3.6%)

$283,000 + $390,000

$673,000

2019

$4,833 (+1.9%)

$246,800 + $381,700

$628,500

2018

$4,742 (+6.5%)

$222,900 + $382,700

$605,600

2017

$4,453 (+8.6%)

$211,300 + $335,100

$546,400

2016

$4,101 (+6.4%)

$217,800 + $287,900

$505,700

2015

$3,853

$217,800 + $266,200

$484,000

Tax history for 36 Tradewinds Rd

Year

Property tax

Land + Additions

Assessment*

2023

$5,221 (−3.1%)

$451,900 + $537,000

$988,900

2022

$5,387 (+1.9%)

$340,400 + $452,900

$793,300

2021

$5,287 (+5.6%)

$297,200 + $420,200

$717,400

2020

$5,007 (+3.6%)

$283,000 + $390,000

$673,000

2019

$4,833 (+1.9%)

$246,800 + $381,700

$628,500

2018

$4,742 (+6.5%)

$222,900 + $382,700

$605,600

2017

$4,453 (+8.6%)

$211,300 + $335,100

$546,400

2016

$4,101 (+6.4%)

$217,800 + $287,900

$505,700

2015

$3,853

$217,800 + $266,200

$484,000

*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: 3

Heating & Cooling
Heating Type: Forced Hot Water

Room Information
# of Rooms: 6

Exterior

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

Property Information
Subdivision Name: OAK BLUFFS
Living Sq. Ft: 2,072
Gross Sq. Ft: 3,634
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 23,087
Municipality Name: OAK BLUFFS
Acres: 0.53
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 3.0
Sq. Ft.: 2,072
Stories: 2.0
Lot Size: 0.53 acres
Style: Single Family Residential
Year Built: 1999
Year Renovated: 2008
County: Dukes County
APN: 3877047

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 • 0.1mi

7/10

Martha's Vineyard Regional High School

Public 9-12 • Assigned • 2.5mi

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

5/10 Heat Factor

7 days above 88° expected this year, 20 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

$1.40M – $1.69M

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

$639,000

Land— sq ft

52 Heath Hen Ln, Vineyard Haven, MA 02568

Sunny lot • Septic design • Quiet neighborhood

$1,095,000

1 bed2 baths1,428 sq ft

323 County Rd, Oak Bluffs, MA 02557

First floor den • Spacious deck • Outdoor shower

$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

$2,695,000

5 beds4 baths2,374 sq ft

124 Main St, Vineyard Haven, MA 02568

Historic character • Period details • Light filled kitchen

$2,595,000

4 beds4.5 baths3,927 sq ft

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Private lot • Two new kitchens • Five new bathrooms

Home values near 36 Tradewinds Rd

Data from public records.

Address	Redfin Estimate
28 Tradewinds Rd, Oak Bluffs, MA 2 Beds \| 1 Baths \| 800 Sq. Ft.	$796,448
34 Tradewinds Rd, Oak Bluffs, MA 3 Beds \| 2.5 Baths \| 1646 Sq. Ft.	$1,439,822
89 Wing Rd, Oak Bluffs, MA 5 Beds \| 2 Baths \| 2398 Sq. Ft.	$1,446,259
83 Wing Rd, Oak Bluffs, MA 4 Beds \| 2 Baths \| 1705 Sq. Ft.	$1,477,751
13 Norris Ave, Oak Bluffs, MA 4 Beds \| 3 Baths \| 2400 Sq. Ft.	$1,833,473
7 Norris Ave, Oak Bluffs, MA 2 Beds \| 1 Baths \| 542 Sq. Ft.	$876,896
92R Wing Rd, Vineyard Haven, MA 2 Beds \| 2 Baths \| 1288 Sq. Ft.	$1,153,079

Address	Redfin Estimate
38 Tradewinds Rd, Oak Bluffs, MA 3 Beds \| 2 Baths \| 1762 Sq. Ft.	$1,445,847
16 Hitchings Cir, Vineyard Haven, MA 4 Beds \| 2 Baths \| 986 Sq. Ft.	$1,063,903
56 Wing Rd, Oak Bluffs, MA 4 Beds \| 2.5 Baths \| 2052 Sq. Ft.	$1,412,670
9 Norris Ave, Oak Bluffs, MA 3 Beds \| 1 Baths \| 1144 Sq. Ft.	$1,014,259
78 Wing Rd, Oak Bluffs, MA 3 Beds \| 2.5 Baths \| 1523 Sq. Ft.	$1,308,626
47 Wing Rd, Oak Bluffs, MA 4 Beds \| 1 Baths \| 1058 Sq. Ft.	$954,080
86 Wing Rd, Oak Bluffs, MA 1 Beds \| 1 Baths \| 741 Sq. Ft.	$917,648

Address	Redfin Estimate
32 Tradewinds Rd, Oak Bluffs, MA 3 Beds \| 2.5 Baths \| 2464 Sq. Ft.	$1,592,083
16 Pheasant Ln, Oak Bluffs, MA 2 Beds \| 1 Baths \| 768 Sq. Ft.	$805,754
8 Arrowhead Ln, Oak Bluffs, MA 3 Beds \| 1 Baths \| 1040 Sq. Ft.	$980,267
7 Arrow Head Ln, Oak Bluffs, MA 3 Beds \| 1 Baths \| 1040 Sq. Ft.	$982,169
10 Pheasant Ln, Oak Bluffs, MA 3 Beds \| 1 Baths \| 1144 Sq. Ft.	$1,087,420
55 Wing Rd, Vineyard Haven, MA 4 Beds \| 2.5 Baths \| 1866 Sq. Ft.	$1,577,792
82 Wing Rd, Oak Bluffs, MA 3 Beds \| 1.5 Baths \| 1408 Sq. Ft.	$1,113,935

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