299 Barnes Rd, Oak Bluffs, MA 02557
OFF MARKET

$3,089,100

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,989 sqft (on 1.20 acres)

299 Barnes Rd, Oak Bluffs, MA 02557

Est. Refi. Payment $17,837/mo*
Refinance Your Home

Home Value

Trulia Estimate
$3.09M
Since last month
Increased$114K (+3.8%)
Since last year
Increased$207K (+7.1%)
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 +122% in the last 10 years
MonthEstimated value
2026
September 2026$3.14M
August 2026$3.06M
July 2026$3.03M
June 2026$3.14M
May 2026$2.99M
April 2026$2.91M
March 2026$3.02M
February 2026$2.98M
January 2026$2.87M
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
309 Barnes Rd, Oak Bluffs, MA
0.07
Single-Family Home
$2,875,000
06/15/26
3
2
1,569
5 Bayes Hill Circle, Oak Bluffs, MA
0.44
Single-Family Home
$1,600,000
01/20/26
4
2.5
2,855
57 Hines Point Rd, Tisbury, MA
0.61
Single-Family Home
$5,000,000
06/04/26
3
2.5
2,589
58 Weaver Ct, Tisbury, MA
0.61
Single-Family Home
$1,250,000
09/25/25
4
3
2,210
126 Border Rd, Tisbury, MA
0.70
Single-Family Home
$1,685,000
10/09/25
3
3
2,251
96 Pond View Dr, Oak Bluffs, MA
0.56
Single-Family Home
$1,600,000
11/07/25
4
2.5
2,115
12 Park Avenue, Tisbury, MA
0.67
Single-Family Home
$975,000
03/30/26
3
2
1,469
Grovedale Rd, Oak Bluffs, MA
0.45
Single-Family Home
$1,450,000
01/15/26
3
4
2,376
44 Tiffany Dr, Oak Bluffs, MA
0.57
Single-Family Home
$1,600,000
01/06/26
4
4.5
4,023
28 Grovedale Road, Oak Bluffs, MA
0.49
Single-Family Home
$1,450,000
01/15/26
3
3.5
2,376

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
309 Barnes Rd, Oak Bluffs, MA 02557
0.07
$2,875,000
3
2
1,569
Recently Sold
285 Barnes Road, Oak Bluffs, MA 02557
0.07
$3,463,500
4
3.5
3,403
Off Market
32 Double Ox Rd, Oak Bluffs, MA 02557
0.17
$1,604,100
2
2
1,716
Off Market
267 Barnes Rd, Oak Bluffs, MA 02557
0.16
$4,395,000
3
5.5
4,046
For Sale
31 Double Ox Rd, Oak Bluffs, MA 02557
0.19
$1,945,300
3
3.5
2,407
Off Market
27 Double Ox Rd, Oak Bluffs, MA 02557
0.23
$3,400,000
3
4.5
3,260
For Sale
2 Hope'S Way, Oak Bluffs, MA 02557
0.26
$665,000
3
3.5
1,716
Recently Sold
8 Hope'S Way, Oak Bluffs, MA 02557
0.26
$2,001,100
3
3.5
2,407
Off Market
4 Hope'S Way, Oak Bluffs, MA 02557
0.27
$1,985,900
2
2.5
2,407
Off Market
30 Double Ox Rd, Oak Bluffs, MA 02557
0.31
$1,150,000
-
-
-
For Sale
3 Hope'S Way, Oak Bluffs, MA 02557
0.37
-
2
2.5
2,407
Off Market
34 Double Ox Rd, Oak Bluffs, MA 02557
0.37
$1,560,400
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 299 Barnes Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2000
1.2 acre lot
1,989 sqft
$1,553/sqft

About this House

This single-family home is located at 299 Barnes Rd, Oak Bluffs, MA. 299 Barnes Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has 3 bedrooms, 3 bathrooms and approximately 1,989 sqft of floor space. This property has a lot size of 1.20 acres and was built in 2000.
299 Barnes Rd, Oak Bluffs, MA 02557 is a 3 bedroom, 3 bathroom, 1,989 sqft single-family home built in 2000. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,089,100.

Home Details for 299 Barnes Rd

Interior Features

Heating & Cooling
Heating: GasHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 2000Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 1.20 acres

Price and Tax history

YearProperty taxTax assessment
2025
$14,153
$2,802,500
Home facts updated by county records

Market trends in Oak Bluffs

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
72
14MoM

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 299 Barnes Rd

  • What is 299 Barnes Rd estimated to be worth?
    Trulia's estimated value for 299 Barnes Rd in Oak Bluffs, MA is $3,089,100.
  • Is Oak Bluffs a buyer's or seller's market?
    Oak Bluffs is currently a seller'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.
  • What are the closest schools to 299 Barnes Rd?
    The closest schools to 299 Barnes Rd in Oak Bluffs, MA are Martha's Vineyard Regional High School (rated 6/10), Oak Bluffs Elementary School (Pre-K/Middle, rated 7/10).
  • How big is the lot at 299 Barnes Rd?
    The lot at 299 Barnes Rd in Oak Bluffs, MA is about 1.2 acres.

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