39 Windemere Rd
Oak Bluffs, MA 02557
Studio
Studio
(on 0.33 acres)
Local Information
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Description
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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 39 Windemere Rd
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Property Type / Style Property Type: Single Family Home |
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Lot Area: 0.33 acres |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $495 |
| Assessment | $98,000 |
Home facts updated by county records
Comparable Sales for 39 Windemere Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $975,000 | 09/30/25 | 3 | 2 | 836 | |
0.24 | Single-Family Home | $1,310,000 | 08/18/25 | 3 | 2 | 1,964 | |
0.32 | Single-Family Home | $1,530,000 | 01/13/26 | 3 | 2 | 2,015 | |
0.32 | Single-Family Home | $1,530,000 | 01/13/26 | 3 | 2 | 2,015 | |
0.42 | Single-Family Home | $1,270,000 | 05/23/25 | 3 | 2 | 2,192 | |
0.39 | Single-Family Home | $1,600,000 | 05/22/25 | 3 | 2 | 1,594 | |
0.34 | Single-Family Home | $1,350,000 | 08/15/25 | 3 | 2 | 1,864 | |
0.55 | Single-Family Home | $1,850,000 | 08/04/25 | 3 | 3 | 2,210 | |
0.57 | Single-Family Home | $880,000 | 10/17/25 | 3 | 2 | 1,365 | |
0.50 | Single-Family Home | $1,865,000 | 12/04/25 | 4 | 4 | 2,820 |
Assigned Schools
These are the assigned schools for 39 Windemere Rd.
- Oak Bluffs Elementary School
- PK-8
- Public
- 390 Students
7/10GreatSchools RatingParent Rating AverageAn excellent school where students seem to be happy, learning and engaged. You can tell the teachers really care about and truly want the best for their students. The new principal is very energetic, involved and approachable and he seems very well-liked by students, parents and the staff (which is everything).Parent Review7mo ago - Martha's Vineyard Regional High School
- 9-12
- Public
- 703 Students
6/10GreatSchools RatingParent Rating AverageStandards for academic engagement are ON THE FLOOR at this school. The “c1” courses are equivalent to a special ed class in any other school, and an honors class to a typical c1 course. Very, very low expectations for C1 students, often no homework at all, or just one assignment per week, and very little in class work. Many teachers in the school are just blatantly bad at their jobs. The school is not able to address it due to a lack of new teachers, but also because they refuse to train teachers properly. I will admit, many teachers are incredible, but it is unacceptable that the academic standards are so incredibly low and how the administration allows teachers to get by without being able to teach the curriculum during the school year. Specifically, this school and the school system on the island in general is notorious for its awful math program. The school is now having to extend the math period for freshmen because of the amount of failing students (likely more changes to come). The administration has also consistently shown disregard for the opinions of students and families, particularly about the new phone policy. Many valid arguments were simply dismissed or never addressed or answered prior to the establishment of the policy. The administration is also very unaware of what is actually happening (particularly the former principal) in the student body, as a very, very small percentage of students are actually following the policy—the vast majority sticking to the old rule of just not having phones out in class, while the administration continually brags about how well the implementation of the policy has gone. Hopefully as the former principal is now gone some of these issues will be addressed, but it is important to note that there are many issues with this school.Student Review8mo ago 
Check out schools near 39 Windemere Rd.
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.
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39 Windemere Rd, Oak Bluffs, MA 02557 is a studio single-family home. This property is not currently available for sale. The current Trulia Estimate for 39 Windemere Rd is $785,200.