Welcome to the Jessie Lee Harris Legacy House in Oak Bluffs, a home named to honor a beloved matriarch whose personal dwelling was a place where love blossomed, family gathered, and nurturing was assured. We invite you to experience the same safe, nurturing, and restorative experience while staying here.
Located just 0.7 miles from Circuit Avenue, 1 mile from Inkwell Beach, and 5-7 minutes from Tony's convenience store. This home offers the perfect balance of accessibility and retreat.
Living & Gathering Areas
At the heart of the home is a large, open-concept living space designed for togetherness. The living room is generously sized and comfortably furnished with plush couches, a flat-screen TV, and plenty of room for lounging, movie nights, or post-beach relaxation. An open overlook from the upstairs landing adds to the airy, connected feel of the home, making it easy for everyone to feel part of the moment even across floors.
Adjacent to the living room is a dedicated dining area, perfect for shared meals, game nights, or lingering conversations after a day exploring the island.<br />
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Kitchen & Dining<br />
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The fully equipped kitchen features stainless steel appliances, ample counter space, and everything needed to prepare family-style meals, beach-day breakfasts, or fresh local seafood dinners. Whether you’re cooking together or grabbing something quick before heading out, the kitchen is designed to be both functional and welcoming.<br />
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Bedrooms & Sleeping Arrangements<br />
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The home comfortably sleeps up to 8 guests, with flexible sleeping options that work well for families and groups:<br />
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Primary Bedroom (En-suite):<br />
A peaceful retreat with a comfortable bed and private full bathroom; perfect for unwinding at the end of the day.<br />
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Second Bedroom:<br />
Bright and inviting, ideal for couples, kids, or additional guests.<br />
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Third Bedroom:<br />
Cozy and versatile, offering comfortable accommodations for restful nights.<br />
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Additional Sleeping:<br />
A pullout couch provides extra flexibility for larger groups.<br />
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Bathrooms<br />
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Primary en-suite bathroom<br />
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Second full bathroom conveniently located for shared use<br />
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Outdoor shower, a Vineyard favorite! Perfect for rinsing off after the beach and enjoying warm summer evenings under the open sky<br />
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Outdoor Living<br />
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Step outside and enjoy a full backyard designed for relaxation and connection. While understated, the outdoor space offers room to unwind, dine, or simply enjoy the fresh island air. Patio furniture creates a comfortable setting for morning coffee, evening conversations, or casual outdoor meals after a day at the beach.<br />
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Location Highlights<br />
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Walkable to Tony’s Market (5–7 minutes) for snacks, essentials, and quick bites<br />
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Easy access to Oak Bluffs Harbor, Circuit Ave shops, dining, and nightlife<br />
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Close to Inkwell Beach, one of the island’s most iconic shorelines<br />
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Whether you’re biking into town, heading to the beach, or spending the day together at home, everything you need is close by.<br />
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Why Guests Love It<br />
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Spacious, family-friendly layout<br />
Open-concept living ideal for gathering<br />
Outdoor shower + backyard space<br />
Walkable, central Oak Bluffs location<br />
Designed for relaxation, connection, and Vineyard memories<br />
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The Experience<br />
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Inspired by a legacy of hospitality, the Jessie Lee Harris Legacy House was created to feel like more than a rental; it’s a place to slow down, reconnect, and feel at home. From shared meals and late-night conversations to sun-soaked beach days and quiet evenings, this home invites you to experience Martha’s Vineyard in a way that feels authentic, comfortable, and restorative.<br />
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Book your stay and make the Legacy House part of your Vineyard story. read more show less