89 Wing Rd, Oak Bluffs, MA 02557
OFF MARKET

$1,254,200

Trulia Estimate
  • 5 Beds
  • 2 Baths
  • 2,398 sqft (on 0.25 acres)

89 Wing Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $6,960/mo*
Refinance Your Home

Home Value

Trulia Estimate
$1.25M
Since last month
Decreased$16K (-1.2%)
Since last year
Increased$9K (+0.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +149% in the last 10 years
MonthEstimated value
2026
August 2026$1.25M
August 2026$1.25M
July 2026$1.27M
June 2026$1.28M
May 2026$1.26M
April 2026$1.25M
March 2026$1.27M
February 2026$1.23M
January 2026$1.23M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
38 Rogers Way, Oak Bluffs, MA
0.26
Single-Family Home
$1,450,000
05/04/26
3
1.5
2,448
8 Hitchings Cir, Oak Bluffs, MA
0.12
Single-Family Home
$860,000
02/09/26
2
2
1,232
22 Wing Rd, Oak Bluffs, MA
0.24
Single-Family Home
$1,000,000
12/30/25
3
1.5
1,136
30 Franklin Ave, Vineyard Haven, MA
0.21
Single-Family Home
$1,900,000
02/09/26
2
2.5
2,137
54 Columbian Ave, Oak Bluffs, MA
0.53
Single-Family Home
$1,187,500
06/12/26
4
2
1,764
35 Stevens Ave, Oak Bluffs, MA
0.14
Single-Family Home
$1,290,020
12/05/25
2
3
1,632
9 Bay View Ave, Oak Bluffs, MA
0.46
Single-Family Home
$1,090,000
01/16/26
3
2
1,428
25 Windy Hill Rd, Oak Bluffs, MA
0.19
Single-Family Home
$982,000
12/19/25
3
1
980
70 Carol Ln, Oak Bluffs, MA
0.20
Single-Family Home
$1,070,000
04/17/26
2
2.5
1,500
10 Winthrop Ave, Oak Bluffs, MA
0.34
Single-Family Home
$1,195,000
06/18/26
3
2
1,188

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
83 Wing Rd, Oak Bluffs, MA 02557
0.04
$1,455,000
4
2
1,705
Off Market
16 Hitchings Circle, Oak Bluffs, MA 02557
0.07
$978,800
2
2
986
Off Market
21 Norris Ave, Oak Bluffs, MA 02557
0.07
$205,100
2
1
1,086
Off Market
18 Hitchings Cir, Oak Bluffs, MA 02557
0.08
$931,500
2
2
1,000
Off Market
19 Hitchings Cir, Oak Bluffs, MA 02557
0.09
$1,000,900
4
1.5
966
Off Market
10 Kims Way, Oak Bluffs, MA 02557
0.10
$1,132,200
4
2.5
1,976
Off Market
21 Pheasant Ln, Oak Bluffs, MA 02557
0.14
$1,635,600
3
2
2,235
Off Market
27 Hitchings Cir, Oak Bluffs, MA 02557
0.11
$992,100
2
1.5
986
Off Market
8 Hitchings Cir, Oak Bluffs, MA 02557
0.12
$860,000
2
2
1,232
Recently Sold
35 Stevens Ave, Oak Bluffs, MA 02557
0.14
$1,290,020
2
3
1,632
Recently Sold
36 Norris Ave, Oak Bluffs, MA 02557
0.14
$1,184,300
3
2
1,321
Off Market
14 Windy Hill Rd, Oak Bluffs, MA 02557
0.16
$1,350,700
3
2
1,456
Off Market

Local Information

  • Map ViewExplore the area around 89 Wing Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1950
0.25 acre lot
2,398 sqft
$523/sqft

About this House

This single-family home is located at 89 Wing Rd, Oak Bluffs, MA. 89 Wing Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has 5 bedrooms, 2 bathrooms and approximately 2,398 sqft of floor space. This property has a lot size of 10890 sqft and was built in 1950.
89 Wing Rd, Oak Bluffs, MA 02557 is a 5 bedroom, 2 bathroom, 2,398 sqft single-family home built in 1950. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,254,200, with a rent estimate of $6,933/month.

Home Details for 89 Wing Rd

Interior Features

Heating & Cooling
Heating: OilHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1950Year Updated: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Old Style

Community

Units in Building: 2

Lot Information

Lot Area: 10890 sqft

Price and Tax history

YearProperty taxTax assessment
2025
$5,198
$1,029,300
Home facts updated by county records

Market trends in Oak Bluffs

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
58
4MoM

Around this home

What Locals Say about Oak Bluffs

At least 18 Trulia users voted on each feature.

  • 96 % Say it's dog friendly

  • 86 % Say kids play outside

  • 83 % Say yards are well-kept

  • 79 % Say it's walkable to restaurants

  • 79 % Say car is needed

  • 78 % Say people would walk alone at night

  • 78 % Say it's walkable to grocery stores

  • 73 % Say there's wildlife

  • 73 % Say they plan to stay for at least 5 years

  • 70 % Say there's holiday spirit

  • 67 % Say it's quiet

  • 62 % Say parking is easy

  • 59 % Say neighbors are friendly

  • 47 % Say there are community events

  • 44 % Say there are sidewalks

  • 36 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Easy to walk dogs"
    0
    Flag
  • P5j4f84ncw
    "Local people, well known community,quite,hard working people,solid business,good schools,hospitality,new opportunities,security and safety place to leave. "
    0
    Flag
  • Adrianalleyne
    "Oak Bluffs has a vibrant history and continues to be a bastion of African American culture. It’s worth checking out some of the many cultural sites in Oak Bluffs and throughout the island "
    0
    Flag
  • Trulia User
    "Oak Bluffs is a charming town with a bustling summer harbor and lovely shopping district. It’s a beautiful place to live. "
    0
    Flag
  • Jrheneeb
    "I love it here. It’s beautiful and the people are amazing. It’s a great place To come relax and unwind. "
    0
    Flag
  • Kayceesmith27
    "I take the bus to and from work . Car for longer distances. Boat to get to the main land which is 45min ride."
    0
    Flag
  • Andrea H.
    "This is fantasy island. It is not like the real world it's not fast paced. we say we're on island time. there's hardly any crime it's safe for kids. and it's a good community."
    0
    Flag
  • tkurian
    "I own a property in Oak Bluffs"
    0
    Flag
  • Kristin Z.
    "We live here year round in what most people think is a vacation paradise for the rich and famous. But in actuality it is one of the best communities to live in terms of caring wonderful neighbors and exciting intellectual stimulation throughout the winter in the form of performances, music groups, communities by interests. "
    0
    Flag
  • Island R. E.
    "This is a lovely and desirable area close to town and everything the island has to offer."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 89 Wing Rd

  • What is 89 Wing Rd estimated to be worth?
    Trulia's estimated value for 89 Wing Rd in Oak Bluffs, MA is $1,254,200.
  • Is Oak Bluffs a buyer's or seller's market?
    Oak Bluffs is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Oak Bluffs?
    Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See recently sold homes in Oak Bluffs, MA.
  • What are the closest schools to 89 Wing Rd?
    The closest schools to 89 Wing Rd in Oak Bluffs, MA are Martha's Vineyard Regional High School (rated 6/10), Oak Bluffs Elementary School (Pre-K/Middle, rated 7/10).
  • How big is the lot at 89 Wing Rd?
    The lot at 89 Wing Rd in Oak Bluffs, MA is about 0.25 acres (10,890 sq ft).

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