55 Wing Rd, Oak Bluffs, MA 02557
OFF MARKET

$1,215,800

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,972 sqft (on 0.64 acres)

55 Wing Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $6,749/mo*
Refinance Your Home
Currently Off Market - Sold Dec 17, 2015 for $401,000

Home Value

Trulia Estimate
$1.22M
Since last month
Decreased$9K (-0.7%)
Since last year
Decreased$40K (-3.1%)
Since last sale
Increased$816K (+203.6%)
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 +168% in the last 10 years
MonthEstimated value
2026
August 2026$1.22M
August 2026$1.22M
July 2026$1.23M
June 2026$1.23M
May 2026$1.22M
April 2026$1.21M
March 2026$1.23M
February 2026$1.21M
January 2026$1.2M
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
35 Stevens Ave, Oak Bluffs, MA
0.21
Single-Family Home
$1,290,020
12/05/25
2
3
1,632
30 Franklin Ave, Vineyard Haven, MA
0.13
Single-Family Home
$1,900,000
02/09/26
2
2.5
2,137
70 Carol Ln, Oak Bluffs, MA
0.26
Single-Family Home
$1,070,000
04/17/26
2
2.5
1,500
8 Hitchings Cir, Oak Bluffs, MA
0.04
Single-Family Home
$860,000
02/09/26
2
2
1,232
22 Wing Rd, Oak Bluffs, MA
0.16
Single-Family Home
$1,000,000
12/30/25
3
1.5
1,136
38 Rogers Way, Oak Bluffs, MA
0.27
Single-Family Home
$1,450,000
05/04/26
3
1.5
2,448
5 Johns Way, Oak Bluffs, MA
0.46
Single-Family Home
$880,000
10/17/25
3
2
1,365
1 Jessie Leigh Mitchell Way, Oak Bluffs, MA
0.63
Single-Family Home
$1,000,000
12/12/25
2
2.5
2,128
10 Winthrop Ave, Oak Bluffs, MA
0.25
Single-Family Home
$1,195,000
06/18/26
3
2
1,188
25 Windy Hill Rd, Oak Bluffs, MA
0.22
Single-Family Home
$982,000
12/19/25
3
1
980

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
16 Hitchings Circle, Oak Bluffs, MA 02557
0.04
$978,800
2
2
986
Off Market
18 Hitchings Cir, Oak Bluffs, MA 02557
0.05
$931,500
2
2
1,000
Off Market
83 Wing Rd, Oak Bluffs, MA 02557
0.06
$1,455,000
4
2
1,705
Off Market
19 Hitchings Cir, Oak Bluffs, MA 02557
0.06
$1,000,900
4
1.5
966
Off Market
8 Hitchings Cir, Oak Bluffs, MA 02557
0.04
$860,000
2
2
1,232
Recently Sold
27 Hitchings Cir, Oak Bluffs, MA 02557
0.07
$992,100
2
1.5
986
Off Market
21 Norris Ave, Oak Bluffs, MA 02557
0.09
$205,100
2
1
1,086
Off Market
10 Richmond Ave, Oak Bluffs, MA 02557
0.08
$793,600
2
1
724
Off Market
9 Goode St, Oak Bluffs, MA 02557
0.12
$1,749,100
4
4.5
2,954
Off Market
36 Norris Ave, Oak Bluffs, MA 02557
0.14
$1,184,300
3
2
1,321
Off Market
39 Norris Ave, Oak Bluffs, MA 02557
0.14
$1,164,100
3
2
1,224
Off Market
7 Richmond St, Oak Bluffs, MA 02557
0.11
$998,300
3
1
1,120
Off Market

Local Information

  • Map ViewExplore the area around 55 Wing Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1960
0.64 acre lot
1,972 sqft
$617/sqft
Garage

About this House

Single family home with an in-law apartment.
55 Wing Rd, Oak Bluffs, MA 02557 is a 3 bedroom, 3 bathroom, 1,972 sqft single-family home built in 1960. It last sold for $401,000 on Dec 17, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,215,800, with a rent estimate of $7,091/month.

Home Details for 55 Wing Rd

Interior Features

Interior Details
BasementAtticIn-law unitTypes of Rooms: Family Room, Laundry Room, Master Bath, Mud RoomCeiling Fan
Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: VinylLawnPatio
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached

Property Information

Year Built
Year Built: 1960Year Updated: 2020
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.64 acres

Price and Tax history

DateEventPrice
Dec 17, 2015
Source: LINK #29148
Sold
$401,000

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 55 Wing Rd

  • What is 55 Wing Rd estimated to be worth?
    Trulia's estimated value for 55 Wing Rd in Oak Bluffs, MA is $1,215,800.
  • What is the price history for 55 Wing Rd?
    55 Wing Rd in Oak Bluffs, MA last sold for $401,000 in December 2015.
  • 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 55 Wing Rd have air conditioning?
    Yes, 55 Wing Rd in Oak Bluffs, MA has air conditioning.
  • Does 55 Wing Rd have laundry facilities?
    Yes, 55 Wing Rd in Oak Bluffs, MA has in-unit laundry.

Explore by feature - Air Conditioning

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Oak Bluffs, MA

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Off Market Homes Near 55 Wing Rd

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