39 Windemere Rd, Oak Bluffs, MA 02557
OFF MARKET

39 Windemere Rd
Oak Bluffs, MA 02557

  • Studio

$824,000

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $4,624/mo*
Refinance Your Home

$824,000

Trulia Estimate
as of Aug 16, 2026
Est. Refi. Payment $4,624/mo*
Refinance Your Home
Studio
(on 0.33 acres)

Home Value

Trulia Estimate
$824K
Since last month
Increased$20K (+2.5%)
Since last year
Increased$143K (+20.3%)
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 decreased by -11% in the last 10 years
MonthEstimated value
2026
August 2026$845K
July 2026$831K
June 2026$824K
May 2026$788K
April 2026$712K
March 2026$875K
February 2026$736K
January 2026$795K
2025
2024
2023

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
32 Beach Rd, Oak Bluffs, MA
0.07
Single-Family Home
$975,000
09/30/25
3
2
836
35 E Side Rd, Oak Bluffs, MA
0.24
Single-Family Home
$1,310,000
08/18/25
3
2
1,964
48 Vineyard Avenue Ext, Oak Bluffs, MA
0.32
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
48 Vineyard Ave, Vineyard Haven, MA
0.32
Single-Family Home
$1,530,000
01/13/26
3
2
2,015
5 Johns Way, Oak Bluffs, MA
0.57
Single-Family Home
$880,000
10/17/25
3
2
1,365
71 Netock Ave, Oak Bluffs, MA
0.50
Single-Family Home
$1,865,000
12/04/25
4
4
2,820
13 County Rd, Oak Bluffs, MA
0.30
Single-Family Home
$1,000,000
10/02/25
2
1
1,176
44 Carole Ave, Oak Bluffs, MA
0.38
Single-Family Home
$705,000
04/16/26
4
2
2,123
9 Bay View Ave, Oak Bluffs, MA
0.54
Single-Family Home
$1,090,000
01/16/26
3
2
1,428
25 Oak Ave, Oak Bluffs, MA
0.61
Single-Family Home
$650,000
09/10/25
2
0.5
759

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
34 Windemere Rd, Oak Bluffs, MA 02557
0.05
$2,579,000
4
2
1,399
For Sale
45 Windemere Rd, Oak Bluffs, MA 02557
0.02
$1,719,700
2
1.5
676
Off Market
32 Beach Rd, Oak Bluffs, MA 02557
0.07
$998,800
3
2
836
Off Market
28 Beach Rd, Oak Bluffs, MA 02557
0.08
$3,675,000
4
2.5
1,800
For Sale
27 Beach Rd, Oak Bluffs, MA 02557
0.10
$2,995,000
5
1.5
1,713
For Sale
11 Beach Road, Oak Bluffs, MA 02557
0.16
$1,745,000
2
1
561
For Sale
111 Eastville Ave, Oak Bluffs, MA 02557
0.21
$2,600,000
6
4
2,400
For Sale
76 Eastville Ave, Oak Bluffs, MA 02557
0.24
$1,003,800
2
1.5
1,032
Off Market
68 Eastville Ave, Oak Bluffs, MA 02557
0.24
$1,197,600
3
2
1,411
Off Market
35 E Side Rd, Oak Bluffs, MA 02557
0.24
$1,346,200
3
2
1,964
Off Market
34 Shirley Ave, Oak Bluffs, MA 02557
0.25
$1,606,100
3
3
2,305
Off Market
30 Shirley Ave, Oak Bluffs, MA 02557
0.28
$1,847,900
3
3.5
2,900
Off Market

Local Information

  • Map ViewExplore the area around 39 Windemere Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Lot Size
0.33 acres

About this House

This single-family home is located at 39 Windemere Rd, Oak Bluffs, MA. 39 Windemere Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has a lot size of 0.33 acres.
39 Windemere Rd, Oak Bluffs, MA 02557 is a studio single-family home. It is currently off market. The Trulia Estimate is $824,000, with a rent estimate of $6,243/month.

Home Details for 39 Windemere Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 0.33 acres

Price and Tax history

YearProperty taxTax assessment
2025
$495
$98,000
Home facts updated by county records

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
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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

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Apartments for Rent

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Homes for sale near 39 Windemere Rd

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Off Market Homes Near 39 Windemere Rd

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Frequently asked questions about 39 Windemere Rd

  • What is 39 Windemere Rd estimated to be worth?
    Trulia's estimated value for 39 Windemere Rd in Oak Bluffs, MA is $824,000.
  • 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.
  • What are the closest schools to 39 Windemere Rd?
    The closest schools to 39 Windemere 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 39 Windemere Rd?
    The lot at 39 Windemere Rd in Oak Bluffs, MA is about 0.33 acres (14,374 sq ft).