385 Barnes Rd, Oak Bluffs, MA 02557
Property image
Property image
PENDING
0.98 ACRES

$5,295,000

  • 3 Beds
  • 5.5 Baths
  • 3,608 sqft (on 0.98 acres)

385 Barnes Rd, Oak Bluffs, MA 02557

Est. Mortgage $30,520/mo*
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Home Highlights

Single-Family Home
Built in 2004
0.98 acre lot
$1,468/sqft

Local Information

  • Map ViewExplore the area around 385 Barnes Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

SPECTACULAR WATERFRONT ESCAPE WITH POOL AND UNFORGETTABLE SUNSETS. Set along a coveted stretch of Lagoon frontage, this beautifully designed waterfront home captures the essence of relaxed luxury on Martha’s Vineyard. With 125 feet of private sandy beachfront and over 5,400 square feet of living space across three levels, the property is thoughtfully oriented to maximize light, views, and connection to the outdoors. The main living spaces are both dramatic and inviting, with high ceilings, skylights, and walls of glass that frame the ever-changing water views. A central staircase and classic columns define the space, with a decorative stone fireplace providing a natural focal point and warmth. A true chef’s kitchen is equipped with stainless steel appliances, expansive stone counter space, custom cabinetry and an oversized island. A wet bar featuring a beverage refrigerator and ice maker enhances the entertaining flow, while a more casual dining area provides a comfortable setting for hosting. The home includes three spacious ensuite bedrooms. The primary suite is privately situated and enjoys water views, direct access to the pool terrace, and a luxurious bath with soaking tub, double vanity, and glass-enclosed shower. Two additional en suite bedrooms are located on the second level, along with an open sitting area that overlooks the main living room below. Designed with entertaining in mind, the lower level features a billiards/game room, den, bonus room, kitchenette, wine storage, and flexible room for a gym or additional use. Outdoor living is a highlight of this fabulous property, with a heated pool and spa set within a bluestone terrace, and an outdoor kitchen area ready for your custom design and choice of appliances. This space is perfect under the open sky with multiple areas for lounging. The calm Lagoon waters are just steps away and offer ideal conditions for swimming, paddling, boating, and clamming, with the ability to secure a mooring. The Lagoon is known for some of the best steamers, littlenecks, and cherry stones on the Island. In fact, there is a huge clam bed in the Lagoon right behind the house off the private beach. Offered furnished, with a proven strong rental history, this property also enjoys a 2-car garage and is a rare offering combining privacy, comfort, and exceptional waterfront living.
Last check for updates: about 9 hours ago
Listing courtesy of Stephanie Roache
Donnelly + Co
Source: LINK, MLS#42465
Also Listed on MLS PIN, MLS PIN, LINK.

Home Details for 385 Barnes Rd

Interior Features

Interior Details
Basement: Designed for entertaining, the walk-out lower level features a den, kitchenette, and wine cellar, complemented by a billiards/game room, bonus room, and direct outdoor access.Number of Rooms: 11
Beds & Baths
Number of Bedrooms: 3Main Level Bedrooms: 1Number of Bathrooms: 7Number of Bathrooms (full): 4Number of Bathrooms (half): 3
Dimensions and Layout
Living Area: 3608 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Viking Gas 4-burner Range and Double Wall Ovens; Thermador Microwave, Washer: Whirlpool Duet Washer
Heating & Cooling
Heating: GFHANo CoolingHas HeatingHeating Fuel: GFHA

Exterior Features

Exterior Home Features
Other Structures: There is a detached two-car garage with a full second floor for storage space.Exterior: WViews, Porch, Patio, P/Pool, H/Tub, PvtBchFoundation: Poured Concrete
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Pea stone driveway
Frontage
WaterfrontWaterfront: WaterfrontFrontage Type: WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Days on Market: 136

Property Information

Year Built
Year Built: 2004Year Renovated: 2016
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence

Price & Status

Price
List Price: $5,295,000Price Per Sqft: $1,468

Active Status

MLS Status: PS

Location

Direction & Address
City: Oak Bluffs

Agent Information

Listing Agent
Listing ID: 42465

Building

Building Area
Building Area: 3608 Square Feet

Lot Information

Lot Area: 0.98 acres

Offer

Listing Agreement Type: E

Rental Terms, Policies & Fees

Furnished

Miscellaneous

BasementMls Number: 42465Projected Close Date: Mon Oct 05 2026

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

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

Home Value

Trulia Estimate
$4.8M
Since last month
Decreased$8K (-0.2%)
Since last year
Decreased$459K (-8.7%)
Since last sale
Increased$4M (+383.2%)
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 +103% in the last 10 years
MonthEstimated value
2026
September 2026$4.83M
August 2026$4.82M
July 2026$4.84M
June 2026$5.02M
May 2026$5.08M
April 2026$5.15M
March 2026$5.41M
February 2026$5.41M
January 2026$5.39M
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
44 Tiffany Dr, Oak Bluffs, MA
0.28
Single-Family Home
$1,600,000
01/06/26
4
4.5
4,023
126 Border Rd, Tisbury, MA
0.31
Single-Family Home
$1,685,000
10/09/25
3
3
2,251
5 Bayes Hill Circle, Oak Bluffs, MA
0.49
Single-Family Home
$1,600,000
01/20/26
4
2.5
2,855
12 Park Avenue, Tisbury, MA
0.51
Single-Family Home
$975,000
03/30/26
3
2
1,469
515 Edgartown Rd, Tisbury, MA
0.57
Single-Family Home
$1,500,000
03/03/26
6
3
5,418
63 Bayes Hill Rd, Oak Bluffs, MA
0.60
Single-Family Home
$2,900,000
03/30/26
4
4
5,169
309 Barnes Rd, Oak Bluffs, MA
0.36
Single-Family Home
$2,875,000
06/15/26
3
2
1,569
7 Upper Meadow Ln, Oak Bluffs, MA
0.86
Single-Family Home
$1,625,000
05/12/26
4
2.5
3,268
35 Tower Ridge Rd, Oak Bluffs, MA
1.07
Single-Family Home
$1,700,000
11/03/25
3
4
2,558
58 Weaver Ct, Tisbury, MA
0.90
Single-Family Home
$1,250,000
09/25/25
4
3
2,210

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
389 Barnes Rd, Oak Bluffs, MA 02557
0.03
$2,925,800
3
1
936
Off Market
391 Barnes Rd, Oak Bluffs, MA 02557
0.04
$3,067,700
3
2
1,910
Off Market
33 Old Oklahoma Rd, Tisbury, MA 02568
0.27
$3,535,900
3
3
2,417
Off Market
21 Old Oklahoma Rd, Tisbury, MA 02568
0.27
$2,723,100
3
2.5
1,657
Off Market
44 Tiffany Dr, Oak Bluffs, MA 02557
0.28
$2,595,000
4
4.5
4,023
For Sale
31 Double Ox Rd, Oak Bluffs, MA 02557
0.28
$1,945,300
3
3.5
2,407
Off Market
Old Oklahoma Rd, Vineyard Haven, MA 02568
0.31
-
-
-
-
Off Market
126 Border Rd, Tisbury, MA 02568
0.31
$2,252,600
3
3
2,251
Off Market
32 Double Ox Rd, Oak Bluffs, MA 02557
0.30
$1,604,100
2
2
1,716
Off Market
27 Double Ox Rd, Oak Bluffs, MA 02557
0.30
$3,400,000
3
4.5
3,260
For Sale
19 Tiffany Dr, Oak Bluffs, MA 02557
0.33
$1,986,200
4
2.5
2,585
Off Market
20 Sunnyside Ave, Tisbury, MA 02568
0.36
$5,995,000
3
3
2,280
For Sale

Price and Tax history

DateEventPrice
Sep 2, 2026
Source: MLS PIN #73496934
Pending
$5,295,000
Aug 19, 2026
Source: MLS PIN #73496934
Contingent
$5,295,000
Jul 7, 2026
Source: LINK #42465
PriceChange
$5,295,000
Price decreased by 4%
Apr 7, 2026
Source: LINK #42465
Listed For Sale
$5,495,000
Dec 15, 2025
Source: LINK #43040
ListingRemoved
$5,995,000

LGBTQ Local Legal Protections

Stephanie Roache, Donnelly + Co
© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-18 02:29:53 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.

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Frequently asked questions about 385 Barnes Rd

  • What is the estimated monthly payment for 385 Barnes Rd?
    Based on a $5,295,000 list price with 20% down at today's rates, the estimated monthly payment for 385 Barnes Rd in Oak Bluffs, MA is approximately $31,103 (about $28,822 principal & interest, $2,206 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Oak Bluffs?
    Residents describe Oak Bluffs, MA as dog-friendly, well-kept, and walkable to restaurants. See homes for sale in Oak Bluffs, MA.
  • What are the closest schools to 385 Barnes Rd?
    The closest schools to 385 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).
  • What is 385 Barnes Rd estimated to be worth?
    Trulia's estimated value for 385 Barnes Rd in Oak Bluffs, MA is $4,802,000.
  • Does 385 Barnes Rd have a pool?
    Yes, 385 Barnes Rd in Oak Bluffs, MA has a pool.
  • How big is the lot at 385 Barnes Rd?
    The lot at 385 Barnes Rd in Oak Bluffs, MA is about 0.98 acres (42,689 sq ft).
385 Barnes Rd, Oak Bluffs, MA 02557 is a 3 bedroom, 7 bathroom, 3,608 sqft single-family home built in 2004. This property is currently available for sale and was listed by LINK on Apr 7, 2026. The MLS # for this home is MLS# 42465.