2 Wing Rd, Oak Bluffs, MA 02557
Property image
Property image
OFF MARKET

$999,000

Trulia Estimate
  • Studio

2 Wing Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $5,558/mo*
Refinance Your Home
Currently Off Market - Sold Jan 14, 2016 for $620,000

Home Value

Trulia Estimate
$999K
Since last month
Decreased$39K (-3.8%)
Since last year
Increased$47K (+5%)
Since last sale
Increased$379K (+61.1%)
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 +60% in the last 10 years
MonthEstimated value
2026
August 2026$999K
August 2026$991K
July 2026$1.04M
June 2026$1.02M
May 2026$950K
April 2026$951K
March 2026$984K
February 2026$926K
January 2026$923K
2025
2024
2023
2022
2021

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
22 Wing Rd, Oak Bluffs, MA
0.08
Single-Family Home
$1,000,000
12/30/25
3
1.5
1,136
8 Hitchings Cir, Oak Bluffs, MA
0.22
Single-Family Home
$860,000
02/09/26
2
2
1,232
30 Franklin Ave, Vineyard Haven, MA
0.15
Single-Family Home
$1,900,000
02/09/26
2
2.5
2,137
10 Winthrop Ave, Oak Bluffs, MA
0.16
Single-Family Home
$1,195,000
06/18/26
3
2
1,188
24 School St, Oak Bluffs, MA
0.42
Single-Family Home
$782,000
03/06/26
2
1
861
56 Garvin St, Oak Bluffs, MA
0.24
Single-Family Home
$1,235,000
05/29/26
2
1
1,300
70 Carol Ln, Oak Bluffs, MA
0.48
Single-Family Home
$1,070,000
04/17/26
2
2.5
1,500
35 Stevens Ave, Oak Bluffs, MA
0.43
Single-Family Home
$1,290,020
12/05/25
2
3
1,632
25 Windy Hill Rd, Oak Bluffs, MA
0.42
Single-Family Home
$982,000
12/19/25
3
1
980
22 Firehouse Ln, Oak Bluffs, MA
0.53
Single-Family Home
$905,000
09/02/26
2
1
1,074

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
31 Winthrop Ave, Oak Bluffs, MA 02557
0.04
$1,212,900
2
2
1,646
Off Market
184 Circuit Avenue #0, Oak Bluffs, MA 02557
0.06
$1,137,300
Studio
-
1,942
Off Market
12 Wing Rd, Oak Bluffs, MA 02557
0.04
$1,379,800
2
2.5
1,872
Off Market
26 Winthrop Ave, Oak Bluffs, MA 02557
0.09
$839,000
1
1
804
For Sale
112 Dukes County Avenue, Oak Bluffs, MA 02557
0.11
$549,000
-
-
-
For Sale
22 Wing Rd, Oak Bluffs, MA 02557
0.08
$1,000,000
3
1.5
1,136
Recently Sold
3 Debettencourt Cir, Oak Bluffs, MA 02557
0.09
$1,122,700
1
2.5
1,640
Off Market
30 Shawmut Ave, Oak Bluffs, MA 02557
0.10
$1,301,900
4
2
-
Off Market
Heather Ln, Oak Bluffs, MA 02557
0.13
$425,000
-
-
-
For Sale
24 Shawmut Ave, Oak Bluffs, MA 02557
0.13
$1,170,700
4
2
1,770
Off Market
14 Richmond Ave, Oak Bluffs, MA 02557
0.14
$976,800
3
1
986
Off Market
10 Winthrop Ave, Oak Bluffs, MA 02557
0.16
$1,195,000
3
2
1,188
Recently Sold

Local Information

  • Map ViewExplore the area around 2 Wing Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home

About this House

This single-family home is located at 2 Wing Rd, Oak Bluffs, MA. 2 Wing Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has a lot size of 0.46 acres.
2 Wing Rd, Oak Bluffs, MA 02557 is a studio single-family home. It last sold for $620,000 on Jan 14, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $999,000, with a rent estimate of $6,560/month.

Home Details for 2 Wing Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 3920 sqft

Price and Tax history

DateEventPrice
Jan 14, 2016
Source: LINK #27767
Sold
$620,000
May 21, 2012
Source: LINK #23304
Sold
$225,000
Aug 18, 2006
Source: N/A
Sold
$30,000

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 2 Wing Rd

  • What is 2 Wing Rd estimated to be worth?
    Trulia's estimated value for 2 Wing Rd in Oak Bluffs, MA is $999,000.
  • What is the price history for 2 Wing Rd?
    2 Wing Rd in Oak Bluffs, MA last sold for $620,000 in January 2016.
  • 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.
  • How big is the lot at 2 Wing Rd?
    The lot at 2 Wing Rd in Oak Bluffs, MA is about 0.46 acres (20,038 sq ft).

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