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Offered at $3,295,000Active
beds
5
baths
4
sq ft
2,330
Built
2025

29 and 33 Lagoon Pond Road

Tisbury, MA 02568

About this home

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.

Listing last checked: Listing updated:

Listed by Madelyn Silvia · Wallace & Co. Sotheby's International Realty · MLS #73554212

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Details at a glance

Interior4 property facts
Rooms
11
Heating
Heat Pump
Cooling
Heat Pump
Basement
Yes · Partial, Bulkhead
Building5 property facts
Style
Single Family Residence
Year built
2025
Garage
2
Parking
12
Foundation
Concrete Perimeter
Land & utilities5 property facts
Lot size
0.28 acres
Water
Public
Sewer
Public Sewer
Pool
Not reported
Zoning
COMM
Financial2 property facts
Annual taxes
$11,151
Assessment year
2026

Location

Estimated monthly cost

Explore costs at the $3,295,000 asking price. Adjust the assumptions to your situation.

Known monthly costs$17,591 / monthAdjust
Principal & interest
$16,661
Property tax
$929
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $11,151. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

More property insights

Automated value estimate $2,994,198

Estimated range $2,759,145–$3,229,250.

Automated estimates are not appraisals or guarantees of market value.

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Photo-based condition insights

Overall presentation: excellent

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About 29 and 33 Lagoon Pond Road

Can I request a private showing?

Request a tour of 29 and 33 Lagoon Pond Road and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.