34 Massasoit Ave, Oak Bluffs, MA 02557
Property image
Property image
SOLD
FEB 11, 2026

$1,945,400

Trulia Estimate
  • 6 Beds
  • 3.5 Baths
  • 1,616 sqft

34 Massasoit Ave, Oak Bluffs, MA 02557

Refinance Your Home
Currently Off Market - Sold Feb 11, 2026 for $2,000,000

Home Value

Trulia Estimate
$1.95M
Since last month
Increased$382K (+24.5%)
Since last year
Decreased$764K (-28.2%)
Since last sale
Decreased$55K (-2.7%)
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 +177% in the last 10 years
MonthEstimated value
2026
August 2026$1.95M
August 2026$1.93M
July 2026$1.56M
June 2026$1.57M
May 2026$1.57M
April 2026$1.57M
March 2026$2.01M
February 2026$2.01M
January 2026$1.57M
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
1 Rowland Ave, Oak Bluffs, MA
0.40
Single-Family Home
$2,025,000
09/30/25
6
3
3,009
22 Greenleaf Ave, Oak Bluffs, MA
0.32
Single-Family Home
$2,100,000
11/07/25
3
2
1,608
14 Chapman Ave, Oak Bluffs, MA
0.43
Single-Family Home
$1,775,000
03/02/26
5
2
1,469
33 Ocean Ave, Oak Bluffs, MA
0.19
Single-Family Home
$2,775,000
06/29/26
3
2.5
1,845
10 Winthrop Ave, Oak Bluffs, MA
0.35
Single-Family Home
$1,195,000
06/18/26
3
2
1,188
23 Laurel Ave, Oak Bluffs, MA
0.50
Single-Family Home
$1,300,000
12/18/25
4
2
1,248
11 John Wesley Ave, Oak Bluffs, MA
0.62
Single-Family Home
$1,475,000
10/10/25
4
1.5
1,304
30 Franklin Ave, Vineyard Haven, MA
0.47
Single-Family Home
$1,900,000
02/09/26
2
2.5
2,137
25 Pennacook Ave, Oak Bluffs, MA
0.19
Single-Family Home
$2,100,000
08/11/26
4
4
2,516

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
1 Bayliss Ave, Oak Bluffs, MA 02557
0.03
$1,179,400
4
1.5
1,299
Off Market
56 Narragansett Ave #3B, Oak Bluffs, MA 02557
0.05
$644,300
2
1
655
Off Market
56 Narragansett Ave #3A, Oak Bluffs, MA 02557
0.05
$595,900
2
1
647
Off Market
1 Cottage Park, Oak Bluffs, MA 02557
0.04
$910,800
3
2.5
987
Off Market
53 CIRCUIT AVE, OAK BLUFFS, MA 02557
0.07
$5,500,000
6
4.5
5,706
For Sale
16 Cottage Park, Oak Bluffs, MA 02557
0.08
$839,000
2
1
939
Recently Sold
2 Fisk Ave, Oak Bluffs, MA 02557
0.08
$720,700
3
1
725
Off Market
1 Pease Ave, Oak Bluffs, MA 02557
0.08
$750,000
2
1
623
Recently Sold
59 Tuckernuck Ave, Oak Bluffs, MA 02557
0.10
$2,650,000
4
2.5
1,900
For Sale
51 Rural Cir, Oak Bluffs, MA 02557
0.10
$684,200
3
1.5
806
Off Market
9 Forest Cir, Oak Bluffs, MA 02557
0.10
$696,600
2
1.5
508
Off Market

Local Information

  • Map ViewExplore the area around 34 Massasoit Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1900
1,616 sqft
$1,238/sqft

About this House

Located on the corner of Circuit Ave and Massasoit this B1 property with mixed use capability has an existing Victorian home with 6 bedrooms, and 3.5 bathrooms and plenty of room to build a commercial building facing Circuit Ave. The house spacious home with a large wrap around porch would be a great weekly rental property or for employee housing. Right in the heart of Oak Bluffs, walkable to shops, restaurants, beaches, and ferries. . The commercial zoned land has been approved for several different situations from housing to store fronts. Come take a look at all this property has to offer.
34 Massasoit Ave, Oak Bluffs, MA 02557 is a 6 bedroom, 4 bathroom, 1,616 sqft single-family home built in 1900. It last sold for the $2,000,000 asking price on Feb 11, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,945,400.
Last check for updates: about 15 hours ago
Listed by Lisa Lucier
Anchor Realty of Martha's Vineyard
Bought with: Jennifer B. DaSilva, Compass | Point B
Source: LINK, MLS#44132

Home Details for 34 Massasoit Ave

Interior Features

Interior Details
Basement: CrawlNumber of Rooms: 9
Beds & Baths
Number of Bedrooms: 6Main Level Bedrooms: 2Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1616 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: yes, Washer: yes
Heating & Cooling
Heating: ElectricNo CoolingHas HeatingHeating Fuel: Electric
Windows, Doors, Floors & Walls
Flooring: 2
Levels, Entrance, & Accessibility
Floors: 2
View
Has a ViewView: None, Twn

Exterior Features

Exterior Home Features
Other Structures: 2 shedsExterior: Garden, Patio, Porch, PubBchFoundation: BlockGarden
Parking & Garage
No CarportNo GarageNo Attached GarageParking: yes
Frontage
Frontage Type: NoneNot on Waterfront
Water & Sewer
Sewer: Town

Property Information

Year Built
Year Built: 1900Year Renovated: 2008
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Property Information
Parcel Number: 0

Price & Status

Price
List Price: $2,000,000Price Per Sqft: $1,238/sqft

Active Status

MLS Status: S

Location

Direction & Address
City: Oak Bluffs

Building

Building Area
Building Area: 1616 Square Feet

Lot Information

Lot Area: 6534 sqft

Offer

Listing Agreement Type: E

Miscellaneous

Mls Number: 44132

Price and Tax history

DateEventPrice
Feb 11, 2026
Source: LINK #44132
Sold
$2,000,000
Jan 6, 2026
Source: LINK #43981
Contingent
$1,650,000
Jan 6, 2026
Source: Martha's Vineyard MLS #32500392
Pending
$1,650,000
Dec 5, 2025
Source: LINK #43981
PriceChange
$1,650,000
Price decreased by 27%
Oct 20, 2025
Source: LINK #42580
PriceChange
$2,250,000
Price decreased by 10%

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

© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-10 00:13:32 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

Frequently asked questions about 34 Massasoit Ave

  • What is 34 Massasoit Ave estimated to be worth?
    Trulia's estimated value for 34 Massasoit Ave in Oak Bluffs, MA is $1,945,400.
  • What is the price history for 34 Massasoit Ave?
    34 Massasoit Ave in Oak Bluffs, MA last sold for $2,000,000 in February 2026.
  • 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 34 Massasoit Ave?
    The lot at 34 Massasoit Ave in Oak Bluffs, MA is about 0.15 acres (6,534 sq ft).
  • Does 34 Massasoit Ave have parking?
    Yes, 34 Massasoit Ave in Oak Bluffs, MA has on-site parking.

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