86 Wing Rd, Oak Bluffs, MA 02557
OFF MARKET

$877,700

Trulia Estimate
  • 1 Bed
  • 1 Bath
  • 741 sqft (on 2.18 acres)

86 Wing Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $4,907/mo*
Refinance Your Home

Home Value

Trulia Estimate
$878K
Since last month
Increased$2K (+0.2%)
Since last year
Increased$8K (+0.9%)
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 +113% in the last 10 years
MonthEstimated value
2026
August 2026$898K
July 2026$896K
June 2026$890K
May 2026$888K
April 2026$880K
March 2026$871K
February 2026$856K
January 2026$851K
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
21 Norris Ave, Oak Bluffs, MA
0.15
Single-Family Home
$800,000
09/04/25
2
1
1,086
25 Windy Hill Rd, Oak Bluffs, MA
0.26
Single-Family Home
$982,000
12/19/25
3
1
980
1 Onondaga Ave, Oak Bluffs, MA
0.64
Single-Family Home
$835,000
11/05/25
1
1
960
8 Hitchings Cir, Oak Bluffs, MA
0.18
Single-Family Home
$860,000
02/09/26
2
2
1,232
24 School St, Oak Bluffs, MA
0.59
Single-Family Home
$782,000
03/06/26
2
1
861
56 Garvin St, Oak Bluffs, MA
0.46
Single-Family Home
$1,235,000
05/29/26
2
1
1,300
22 Wing Rd, Oak Bluffs, MA
0.24
Single-Family Home
$1,000,000
12/30/25
3
1.5
1,136
35 Stevens Ave, Oak Bluffs, MA
0.18
Single-Family Home
$1,290,020
12/05/25
2
3
1,632
72 Washington Ave, Vineyard Haven, MA
0.56
Single-Family Home
$992,500
12/22/25
1
1.5
1,152
15 2nd Ave, Oak Bluffs, MA
0.52
Single-Family Home
$875,000
07/28/26
2
1
520

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
21 Pheasant Ln, Oak Bluffs, MA 02557
0.08
$1,635,600
3
2
2,235
Off Market
83 Wing Rd, Oak Bluffs, MA 02557
0.11
$1,455,000
4
2
1,705
Off Market
10 Kims Way, Oak Bluffs, MA 02557
0.14
$1,132,200
4
2.5
1,976
Off Market
21 Norris Ave, Oak Bluffs, MA 02557
0.15
$205,100
2
1
1,086
Off Market
18 Hitchings Cir, Oak Bluffs, MA 02557
0.15
$931,500
2
2
1,000
Off Market
130 Wing Rd, Oak Bluffs, MA 02557
0.18
$1,043,300
2
1
768
Off Market
19 Hitchings Cir, Oak Bluffs, MA 02557
0.16
$1,004,200
4
1.5
966
Off Market
16 Hitchings Circle, Oak Bluffs, MA 02557
0.16
$983,900
2
2
986
Off Market
35 Stevens Ave, Oak Bluffs, MA 02557
0.18
$1,290,020
2
3
1,632
Recently Sold
2 Upper Douglas Ln, Oak Bluffs, MA 02557
0.21
$1,327,900
4
2
1,584
Off Market
8 Hitchings Cir, Oak Bluffs, MA 02557
0.18
$860,000
2
2
1,232
Recently Sold
27 Hitchings Cir, Oak Bluffs, MA 02557
0.18
$989,100
2
1.5
986
Off Market

Local Information

  • Map ViewExplore the area around 86 Wing Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1880
Lot Size
2.18 acres
Living Area
741 sqft
Price/Sqft
$1,184

About this House

This single-family home is located at 86 Wing Rd, Oak Bluffs, MA. 86 Wing Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has 1 bedroom, 1 bathroom and approximately 741 sqft of floor space. This property has a lot size of 2.18 acres and was built in 1880.
86 Wing Rd, Oak Bluffs, MA 02557 is a 1 bedroom, 1 bathroom, 741 sqft single-family home built in 1880. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $877,700, with a rent estimate of $3,106/month.

Home Details for 86 Wing Rd

Interior Features

Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1880Year Updated: 1983
Property Type / Style
Property Type: Single Family HomeArchitecture: cottage

Community

Units in Building: 1

Lot Information

Lot Area: 2.18 acres

Price and Tax history

YearProperty taxTax assessment
2025
$3,880
$768,300
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 86 Wing Rd

  • What is 86 Wing Rd estimated to be worth?
    Trulia's estimated value for 86 Wing Rd in Oak Bluffs, MA is $877,700.
  • 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 86 Wing Rd?
    The closest schools to 86 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 86 Wing Rd?
    The lot at 86 Wing Rd in Oak Bluffs, MA is about 2.2 acres.

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