2 Wing Rd, Vineyard Haven, MA 02557
OFF MARKET

2 Wing Rd
Vineyard Haven, MA 02557

  • 5 Beds
  • 3 Baths
  • 1,522 sqft (on 0.92 acres)

$1,245,100

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $6,864/mo*
Refinance Your Home

$1,245,100

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $6,864/mo*
Refinance Your Home
5 Beds
3 Baths
1,522 sqft
(on 0.92 acres)

Home Value

Trulia Estimate
$1.25M
Since last month
Decreased$17K (-1.4%)
Since last year
Decreased$10K (-0.8%)
Since last sale
Increased$615K (+99.2%)
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 +93% in the last 10 years
MonthEstimated value
2026
August 2026$1.24M
July 2026$1.25M
June 2026$1.26M
May 2026$1.2M
April 2026$1.21M
March 2026$1.24M
February 2026$1.21M
January 2026$1.18M
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
22 Wing Rd, Oak Bluffs, MA
0.07
Single-Family Home
$1,000,000
12/30/25
3
1.5
1,136
8 Hitchings Cir, Oak Bluffs, MA
0.21
Single-Family Home
$860,000
02/09/26
2
2
1,232
30 Franklin Ave, Vineyard Haven, MA
0.14
Single-Family Home
$1,900,000
02/09/26
2
2.5
2,137
10 Winthrop Ave, Oak Bluffs, MA
0.15
Single-Family Home
$1,195,000
06/18/26
3
2
1,188
70 Carol Ln, Oak Bluffs, MA
0.47
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
12 Marthas Park Rd, Oak Bluffs, MA
0.69
Single-Family Home
$1,800,000
08/26/25
4
1.5
1,351
21 Norris Ave, Oak Bluffs, MA
0.31
Single-Family Home
$800,000
09/04/25
2
1
1,086
2 Upper Douglas Ln, Oak Bluffs, MA
0.52
Single-Family Home
$1,295,000
09/05/25
4
2
1,584
5 Johns Way, Oak Bluffs, MA
0.63
Single-Family Home
$880,000
10/17/25
3
2
1,365

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
0 Circuit Avenue, Oak Bluffs, MA 02557
0.05
-
-
-
-
Off Market
31 Winthrop Ave, Oak Bluffs, MA 02557
0.03
$1,215,800
2
2
1,646
Off Market
12 Wing Rd, Oak Bluffs, MA 02557
0.03
$1,380,600
2
2.5
1,872
Off Market
184 Circuit Avenue #0, Oak Bluffs, MA 02557
0.08
$1,140,100
Studio
-
1,942
Off Market
26 Winthrop Ave, Oak Bluffs, MA 02557
0.08
$839,000
1
1
804
For Sale
112 Dukes County Avenue, Oak Bluffs, MA 02557
0.10
$549,000
-
-
-
For Sale
22 Wing Rd, Oak Bluffs, MA 02557
0.07
$1,000,000
3
1.5
1,136
Recently Sold
3 Debettencourt Cir, Oak Bluffs, MA 02557
0.11
$1,138,500
1
2.5
1,640
Off Market
30 Shawmut Ave, Oak Bluffs, MA 02557
0.09
$1,341,300
4
2
-
Off Market
Heather Ln, Oak Bluffs, MA 02557
0.14
$425,000
-
-
-
For Sale
24 Shawmut Ave, Oak Bluffs, MA 02557
0.12
$1,176,800
4
2
1,770
Off Market
14 Richmond Ave, Oak Bluffs, MA 02557
0.13
$994,400
3
1
986
Off Market

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

Property Type
Single-Family Home
Year Built
1900
Lot Size
0.92 acres
Living Area
1,522 sqft
Price/Sqft
$818
Parking
Garage

About this House

Vintage Vineyard- This fully renovated 1900's Farm House is the perfect Vineyard retreat. The charming 4 bedroom 3 bath home has been restored to perfection from top to bottom with no detail overlooked. All systems have been updated including new roof and septic. Sited on an expansive lot and only a short walk to downtown Oak Bluffs and the harbor, this property is the ideal vacation home!
2 Wing Rd, Vineyard Haven, MA 02557 is a 5 bedroom, 3 bathroom, 1,522 sqft single-family home built in 1900. It last sold for $620,000 on Jan 14, 2016. It is currently off market. The Trulia Estimate is $1,245,100, with a rent estimate of $7,888/month.

Home Details for 2 Wing Rd

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Baseboard, GasHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 3

Exterior Features

Exterior Home Features
Roof: Asphalt, Shake ShingleExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1900Year Updated: 2015
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.92 acres

Price and Tax history

DateEventPrice
Jan 14, 2016
Source: N/A
Sold
$620,000
Nov 16, 2015
Source: Agent Provided
Pending
$649,000
Oct 2, 2015
Source: Agent Provided
PriceChange
$649,000
Price decreased by 7%
Aug 21, 2015
Source: Agent Provided
PriceChange
$695,000
Price decreased by 7%
Jul 27, 2015
Source: Agent Provided
Listed For Sale
$749,000

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 Vineyard Haven, MA is $1,245,100.
  • What is the price history for 2 Wing Rd?
    2 Wing Rd in Vineyard Haven, MA last sold for $620,000 in January 2016.
  • Is Vineyard Haven a buyer's or seller's market?
    Vineyard Haven is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Vineyard Haven?
    Residents describe Vineyard Haven, MA as dog-friendly, well-kept, and walkable to restaurants. See recently sold homes in Vineyard Haven, MA.
  • How big is the lot at 2 Wing Rd?
    The lot at 2 Wing Rd in Vineyard Haven, MA is about 0.92 acres (40,037 sq ft).
  • Does 2 Wing Rd have a garage?
    Yes, 2 Wing Rd in Vineyard Haven, MA has a garage.

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Apartments for Rent

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Off Market Homes Near 2 Wing Rd

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Homes for sale near 2 Wing Rd

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