29 & 33 Lagoon Pond Road
Vineyard Haven, MA · $3,295,000
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📊 STR projections🏖️ Beach distances🌊 Flood-zone risk📄 Investment dossier💰 Cash-flow analysis

29 & 33 Lagoon Pond Road

Vineyard Haven, MA 02568
$3,295,000
2 days on market · Listed Jul 23, 2026
Data refreshed Jul 23, 2026
🌊 Not in FEMA SFHA
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Type
SF
Beds
5
Baths
4
Sq Ft
2,330
Acres
0.28
Year Built
2025
$ / Sq Ft
$1,414
Days on Market
2

Investment Snapshot

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Location & Nearby

Map of 29 & 33 Lagoon Pond Road, Vineyard Haven MA with nearby beaches and points of interest
HThis property
  • A
    🍽️ Ackee Tree Caribbean American Grocer
    0.07 mi
  • B
    🍽️ Vineyard Grill
    0.09 mi
  • C
    🍽️ ArtCliff Diner
    0.10 mi
  • D
    🍽️ Wolf's Den Pizzeria Tisbury
    0.11 mi
  • E
    🍽️ The Black Dog Water St. Bakery
    0.11 mi
  • F
    🍽️ 9 Craft Kitchen And Bar
    0.12 mi
  • G
    🛒 Vineyard Haven Stop & Shop
    0.13 mi
  • H
    Gannon & Benjamin Marine Railway
    0.14 mi

About this property

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.

📋 Vineyard Haven Short-Term Rental Rules
Registration, taxes, occupancy caps, and enforcement for STRs in Vineyard Haven
Listed by Madelyn Silvia, Wallace & Co. Sotheby's International Realty