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Oceanfront Chilmark Homes

Direct access to Martha's Vineyard's most dramatic waterfront landscapes.

What Oceanfront Chilmark Homes Offer

What makes oceanfront living here distinctive.

Life on Chilmark's Waterfront

Two wooden Adirondack chairs on a grassy lawn overlooking a bay with forested shoreline and sandy cliffs

Dramatic Coastline

Martha's Vineyard's Most Striking Shores

Blue and gray shingled coastal house with stone retaining wall and manicured lawn under clear sky

Direct Beach Access

Steps to Sand and Water

Modern shingle-clad house with solar panels, wraparound deck, pool, and gazebo surrounded by trees

Island Character

Quiet, Unspoiled Waterfront

What Guests Say

Grace Hagerty Real Estate Inc.

4.89

176 reviews

We had a lovely stay and hope to return! Perfect location for walking to the ferry and other attractions in Vineyard Haven.

Lauren

Stayed in October 2026

We fully enjoyed our stay. This location was perfect for walking into town, and having a parking space was awesome. We were able to drive all over the island and explore. The place is beautifully decorated and was perfect for the two of us. We would definitely stay here again!

Matthew

Stayed in September 2026

Beautiful location and cozy, charming property. We had a great stay!

Daniel

Stayed in September 2026

The house is great and only a mile from Vineyard Haven.

Virginia

Stayed in September 2026

Get more when you book direct

Lower prices, every time

Pay less than you would anywhere else. No middlemen or platform fees.

Direct line, real care

Book with the team that actually runs the property. Faster answers, better service, real accountability.

Not just a transaction

We go further for direct guests. We’re building a relationship, not closing a booking.

Oceanfront Chilmark

Questions Before You Book