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Rare downtown Vineyard Haven compound offering! A unique opportunity to own two separate properties offered together just moments from the ferry, harbor, restaurants, and shops. 33 Lagoon Pond Road is a newly built 3BR/3BA home featuring an open floor plan, designer kitchen with quartz countertops, custom tile baths, water views, private backyard, spacious deck, attached two-car garage, and strong rental history. Complementing 33 Lagoon Pond Road, is 29 Lagoon Pond Road originally built in 1950 and beautifully renovated in 2020. This 2BR/1BA cottage with a private patio and outdoor shower, is ideal for guests, extended family, employee housing, or additional rental income. A rare highlight is the oversized rear parking lot accommodating approximately 10 vehicles--an exceptional amenity in downtown Vineyard Haven. Whether you're seeking a family compound, investment property, or luxury in-town retreat with unmatched flexibility and income potential, this one-of-a-kind offering is not to be missed. Note: Tenants in place, showings are only during turnovers. First opportunity to see both properties is 7/26.

Property Details of 29 & 33 Lagoon Pond Road

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Listed by Madelyn Silvia of Wallace & Co. Sotheby's International Realty

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This site was last updated July 24, 2026 7:52 AM UTC. All properties are subject to prior sale, changes, or withdrawal.

Premier Commercial has chosen to display only certain towns and/or types or styles of properties. This site may not show all listings that are available through the Cape Cod & Islands Multiple Listing Service, Inc.

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