The Most Important Difference Is Character, Not Price
Both islands have a 2% Land Bank transfer fee. Both require ferry or air access from the mainland. Both draw high-net-worth buyers from Boston and New York. The meaningful differences are in scale, community composition, architectural regulation, and price per square foot.
| Factor | Nantucket | Martha's Vineyard |
|---|---|---|
| Size | 50 sq mi, one community | 87 sq mi, six distinct towns |
| Entry price | $2.5M+ | $600K+ (Oak Bluffs) / $2M+ (Edgartown) |
| Land Bank fee | 2% buyer-paid | 2% buyer-paid |
| Architectural control | HDC (strict, covers most of town) | Varies by town, no island-wide HDC |
| Ferry departure point | Hyannis only | Woods Hole, Falmouth, Hyannis, New Bedford |
| Per sq ft vs. comparable | Higher (30-60% above MV) | Lower |
| Community character | Uniform grey-shingle identity | Diverse town-by-town |
Choose Nantucket If:
The island's specific social register and community homogeneity appeal to you. You want the most supply-constrained market with the clearest structural case for long-term value protection. You are drawn to the grey-shingle architectural vocabulary and the HDC's role in preserving it. You are comfortable with the additional logistical complexity of 30-miles-off-Cape island ownership.
Choose Martha's Vineyard If:
You want town-by-town character variation. You value a more robust year-round community. You are specifically drawn to one of the Vineyard's distinct communities in a way that has no Nantucket equivalent: Edgartown's yacht culture, Chilmark's land and privacy, Oak Bluffs' historic and cultural significance. You want more ferry access options from different mainland points.
Analyst note: The buyers who are unhappy with their island choice almost always chose on price or logistics rather than character. The right approach is to spend meaningful time on both islands before committing to either.