29 and 33 Lagoon Pond Road, Tisbury MA 02568
Tisbury, MA 02568 • Vineyard Haven
$3,295,000
Est. $17,791/month
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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.
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Property History
Property Timeline
Listed for Sale
Jul 23, 2026
$3,295,000
Original listing
Agent: Madelyn Silvia
Office: Wallace & Co. Sotheby's International Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 07/23/2026 | 🏠 Listed for Sale | $3,295,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $11,151 | $1,502,800 |
Financial Details
Annual Property Tax
$11,151
Tax Year 2026
Assessed Value
$1,502,800
Facts & Features
2 Car Garage
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
2025
Living Area
2,330 sq ft
Lot Size
0.28 acres
Bedrooms
5
Full Baths
4
Total Rooms
11
Interior
Heating
Heat Pump
Cooling
Heat Pump
Flooring
None
Appliances
Electric Water Heater
Fireplace
None
Basement
Partial, Bulkhead
Laundry
None
Features
None
Exterior
Construction
None
Architecture
Other (see Remarks)
Roof
None
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Garage Spaces
2
Has Garage
Yes
Features
Attached, Under
Total Spaces
12
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$11,151
Assessed Value
$1,502,800
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Sq Ft Disclosures
#29 has 650 SF (Built in 1950 and renovated in 2020) and #33 has 1,680 SF
Documents
None
County
Dukes
Total market time (incl. prior listings)
4 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
2025
Bedrooms
5
Full Bathrooms
4
Living Area
2,330 sq ft
Total Rooms
11
Floor Layout
Interactive room guide
Floor Layout
Finished Area
2,330 sq ft above grade
FeaturesYes
Display Options
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Appliances:
Electric Water Heater
Interior Features:
Windows:
Basement:
Partial, Bulkhead
Laundry:
Security:
Construction & Materials
Style:
Other (See Remarks)
Year Built:
2025
Structure Type:
Exterior Materials:
Roof:
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Heat Pump
Cooling:
Heat Pump
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Road Surface:
Parking & Garage
Garage Spaces:
2
Garage Type:
Attached
Total Parking Spaces:
12
Parking Features:
Attached, Under
Special Features
View:
Yes
View Type:
Scenic View(s)
Community Amenities:
Public Transportation, Shopping, Park
Nearby Schools
School information not available for this location.
Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$929
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
Vineyard Haven
29 and 33 Lagoon Pond Road, Tisbury MA 02568
Tisbury, MA 02568
Listing Information
Listing Agent
Madelyn Silvia
Listing Office
Wallace & Co. Sotheby's International Realty
Office Phone
508-627-3313
Agent MLS ID
CN262477
Office MLS ID
AN9542
Listing Data Updated
Jul 27, 2026 3:05 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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