
29 and 33 Lagoon Pond Road Tisbury — Photo 1 of 39
$3,295,000
29 and 33 Lagoon Pond Road, Tisbury, MA 02568
Tisbury, MA 02568 — Vineyard Haven
Beds
5
Baths
4
SqFt
2,330
Style
Single Family
Built
2025
Rare Downtown Vineyard Haven Compound Offering! An exceptional opportunity to own two separate properties being offered together in the heart of Vineyard Haven. Just moments from the ferry terminal, restaurants, shops, and the harbor, this unique package offers the ideal blend of luxury living, investment potential, and an amenity that is nearly impossible to find in town with expansive parking. 33 Lagoon Pond Road is a newly constructed, thoughtfully designed three bedroom, three bathroom home where luxury meets sophisticated coastal charm. Featuring an open floor plan, a designer kitchen with quartz countertops, custom tile bathrooms, and seamless indoor-outdoor living, the home enjoys water views from the living room, bedrooms, and inviting front porch. A private backyard, spacious rear deck, and attached two car garage provide both privacy and convenience, while the property's impressive rental history adds outstanding investment appeal. Complementing the main residence is 29 Lagoon Pond Road, a beautifully renovated two bedroom, one bath cottage offering its own private retreat with a charming rear patio and outdoor shower. Ideal for extended family, guests, employee housing, or additional rental income, the cottage provides flexibility for a variety of ownership opportunities. A true standout feature of this offering is the oversized rear parking lot at 29 Lagoon Pond Road, accommodating approximately ten vehicles. Parking of this scale is exceptionally rare in downtown Vineyard Haven and significantly enhances the property's versatility. Whether you're seeking a family compound, an income producing investment, or a premier in town property with unmatched flexibility, 29 & 33 Lagoon Pond Road represent a truly one of a kind opportunity in downtown Vineyard Haven. Tenants in place. Showings are limited to turnover days - please inquire with listing agent.
Market Value Analysis
* Analysis is based on 21 actively listed and recently sold comparable properties strictly within Tisbury, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Electric Water Heater
Neighborhood
Public Transportation • Shopping • Park
Geography
Population
9,412
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$115K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
21.5%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Dukes County
164 housing units permitted in the last 12 months (+80% vs the prior 12 months) — 35 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,330 sq ft principal dwelling). Lot size: 12,196 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Madelyn Silvia
Listing Office: Wallace & Co. Sotheby's International Realty
MLS® Number: 73554212
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