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

$1,188,300

Trulia Estimate
  • 2 Beds
  • 4 Baths
  • 2,388 sqft

8 Wing Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $6,597/mo*
Refinance Your Home
Currently Off Market - Sold Dec 2, 2008 for $225,000

Home Value

Trulia Estimate
$1.19M
Since last month
Decreased$15K (-1.3%)
Since last year
Decreased$17K (-1.4%)
Since last sale
Increased$964K (+428.5%)
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 +247% in the last 10 years
MonthEstimated value
2026
August 2026$1.19M
August 2026$1.19M
July 2026$1.2M
June 2026$1.21M
May 2026$1.17M
April 2026$1.17M
March 2026$1.22M
February 2026$1.21M
January 2026$1.13M
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
30 Franklin Ave, Vineyard Haven, MA
0.13
Single-Family Home
$1,900,000
02/09/26
2
2.5
2,137
8 Hitchings Cir, Oak Bluffs, MA
0.19
Single-Family Home
$860,000
02/09/26
2
2
1,232
22 Wing Rd, Oak Bluffs, MA
0.06
Single-Family Home
$1,000,000
12/30/25
3
1.5
1,136
35 Stevens Ave, Oak Bluffs, MA
0.41
Single-Family Home
$1,290,020
12/05/25
2
3
1,632
70 Carol Ln, Oak Bluffs, MA
0.45
Single-Family Home
$1,070,000
04/17/26
2
2.5
1,500
38 Rogers Way, Oak Bluffs, MA
0.43
Single-Family Home
$1,450,000
05/04/26
3
1.5
2,448
10 Winthrop Ave, Oak Bluffs, MA
0.16
Single-Family Home
$1,195,000
06/18/26
3
2
1,188
56 Garvin St, Oak Bluffs, MA
0.24
Single-Family Home
$1,235,000
05/29/26
2
1
1,300
24 School St, Oak Bluffs, MA
0.42
Single-Family Home
$782,000
03/06/26
2
1
861
1 Jessie Leigh Mitchell Way, Oak Bluffs, MA
0.72
Single-Family Home
$1,000,000
12/12/25
2
2.5
2,128

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
12 Wing Rd, Oak Bluffs, MA 02557
0.02
$1,379,800
2
2.5
1,872
Off Market
31 Winthrop Ave, Oak Bluffs, MA 02557
0.03
$1,212,900
2
2
1,646
Off Market
22 Wing Rd, Oak Bluffs, MA 02557
0.06
$1,000,000
3
1.5
1,136
Recently Sold
30 Shawmut Ave, Oak Bluffs, MA 02557
0.08
$1,301,900
4
2
-
Off Market
26 Winthrop Ave, Oak Bluffs, MA 02557
0.08
$839,000
1
1
804
For Sale
184 Circuit Avenue #0, Oak Bluffs, MA 02557
0.08
$1,137,300
Studio
-
1,942
Off Market
14 Richmond Ave, Oak Bluffs, MA 02557
0.12
$976,800
3
1
986
Off Market
24 Shawmut Ave, Oak Bluffs, MA 02557
0.12
$1,170,700
4
2
1,770
Off Market
30 Franklin Ave, Vineyard Haven, MA 02568
0.13
$1,900,000
2
2.5
2,137
Recently Sold
112 Dukes County Avenue, Oak Bluffs, MA 02557
0.12
$549,000
-
-
-
For Sale
3 Debettencourt Cir, Oak Bluffs, MA 02557
0.11
$1,122,700
1
2.5
1,640
Off Market
7 Richmond St, Oak Bluffs, MA 02557
0.15
$998,300
3
1
1,120
Off Market

Local Information

  • Map ViewExplore the area around 8 Wing Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1940
2,388 sqft
$498/sqft

About this House

This home is very well constructed, with large floor beams, large ceiling beams, lathe and plaster walls, and old hardwood floors. All trim, floor, walls, including attic and basement are original. The home is in need of cosmetic repair, but is in overall good shape. The basement could be easily finished, adding 500+ livable sq. ft. The attic could also be finished as a loft. The yard extends back 80 - 90 yards from the road. Quiet neighbors. 1/2 mile to Oak Bluffs center, 4 blocks to Oak Bluffs Elementary, 1/2 mile to beach. Lots of potential for this house and lot..

Neighborhood Description

It's the Vineyard!
8 Wing Rd, Oak Bluffs, MA 02557 is a 2 bedroom, 4 bathroom, 2,388 sqft single-family home built in 1940. It last sold for $225,000 on Dec 2, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,188,300, with a rent estimate of $6,705/month.

Home Details for 8 Wing Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: Family Room, Mud Room, Workshop
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood, Linoleum Vinyl
Appliances & Utilities
Cable ReadyDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: ShingleLawnPatio
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1940Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 10454 sqft

Price and Tax history

DateEventPrice
Mar 16, 2021
Source: N/A
ListingRemoved
Mar 24, 2011
Source: N/A
ListingRemoved
$299,000
Dec 2, 2008
Source: LINK #18051
Sold
$225,000
Oct 6, 2008
Source: N/A
PriceChange
$299,000
Price decreased by 11%
Sep 10, 2008
Source: N/A
Listed For Sale
$335,000

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 8 Wing Rd

  • What is 8 Wing Rd estimated to be worth?
    Trulia's estimated value for 8 Wing Rd in Oak Bluffs, MA is $1,188,300.
  • What is the price history for 8 Wing Rd?
    8 Wing Rd in Oak Bluffs, MA last sold for $225,000 in December 2008.
  • 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.
  • Does 8 Wing Rd have laundry facilities?
    Yes, 8 Wing Rd in Oak Bluffs, MA has in-unit laundry.
  • How big is the lot at 8 Wing Rd?
    The lot at 8 Wing Rd in Oak Bluffs, MA is about 0.24 acres (10,454 sq ft).

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