Windemere Rd
Oak Bluffs, MA 02557
- Studio
Studio
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
About this House
This single-family home is located at Windemere Rd, Oak Bluffs, MA. Windemere Rd is in Oak Bluffs, MA and in ZIP code 02557. This property has a lot size of 10018 sqft.
Windemere Rd, Oak Bluffs, MA 02557 is a studio single-family home. It is currently off market. The Trulia Estimate is $791,400, with a rent estimate of $5,709/month.
Home Details for Windemere Rd
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Property Type / Style Property Type: Single Family Home |
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Lot Area: 10018 sqft |
Market trends in Oak Bluffs
Last updated June 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
54
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $501 |
| Assessment | $99,300 |
Home facts updated by county records
Comparable Sales for Windemere Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.10 | Single-Family Home | $975,000 | 09/30/25 | 3 | 2 | 836 | |
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 | |
0.33 | Single-Family Home | $1,350,000 | 08/15/25 | 3 | 2 | 1,864 | |
0.24 | Single-Family Home | $1,310,000 | 08/18/25 | 3 | 2 | 1,964 | |
0.43 | Single-Family Home | $1,865,000 | 12/04/25 | 4 | 4 | 2,820 | |
0.53 | Single-Family Home | $1,090,000 | 01/16/26 | 3 | 2 | 1,428 | |
0.55 | Single-Family Home | $650,000 | 09/10/25 | 2 | 0.5 | 759 | |
0.38 | Single-Family Home | $705,000 | 04/16/26 | 4 | 2 | 2,123 | |
0.24 | Single-Family Home | $1,000,000 | 10/02/25 | 2 | 1 | 1,176 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 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.
LGBTQ Local Legal Protections
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Apartments for Rent
Homes for sale near Windemere Rd
Off Market Homes Near Windemere Rd
Frequently asked questions about Windemere Rd
- What is Windemere Rd estimated to be worth?Trulia's estimated value for Windemere Rd in Oak Bluffs, MA is $791,400.
- 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 Windemere Rd?The closest schools to 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 Windemere Rd?The lot at Windemere Rd in Oak Bluffs, MA is about 0.23 acres (10,018 sq ft).