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29 & 33 Lagoon Pond Road, Vineyard Haven, MA, 02568

5beds
4baths
2,330sqft
$3,295,000
$1,414price/sqft
$20,132/moest. monthly cost
$805,280/yrincome needed

About This Home

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.

Getting Around

72
WalkingVery Walkable
0
TransitVery Limited Transit
58
BikeBikeable

Schools

4/10
Tisbury Elementary SchoolGrades PK-80.4 mi

Construction

Condition

  • Property condition: Actual
  • Year built: 2025

Materials

  • Foundation: Poured
  • Roof: Asphalt, Shingle, Pitched
  • Construction materials: Shingle Siding

Type & Style

  • Home type: SingleFamily
  • Architectural style: Other
  • Property subType: Single Family Residence

Interior

Appliances

  • Appliances included: Electric Water Heater

Basement

  • Has basement: Yes
  • Basement: Bulkhead Access,Interior Entry

Bedrooms & Bathrooms

  • Bedrooms: 5
  • Bathrooms: 4
  • Full bathrooms: 4

Features

  • Flooring: Hardwood,Tile,Vinyl

Heating

  • Heating features: Has Heating (Unspecified Type)

Interior Area

  • Total structure area: 2,330
  • Total interior livable area: 2,330 sqft

Property

Details

  • Parcel number: TISB M:009A B:0000 L:0014
  • Zoning: C
  • Special condition: None

Features

  • Stories: 2
  • Exterior features: Outdoor Shower

Lot

  • Lot size: 0.28 Acres

Parking

  • Total spaces: 10
  • Parking features: Basement
  • Has garage: Yes
  • Attached garage spaces: 2
  • Covered spaces: 2

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Coastal Flooding
    Coastal FloodingModerate
  • Hurricane
    HurricaneModerate
  • Tsunami
    TsunamiInsufficient Data

How This Home’s Risks Compare

Coastal Flooding
Hurricane
Tsunami

FEMA Declared Disasters Across Massachusetts Counties

Hurricane

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $16,661$199,932
Home Insurance *$1,749$20,988
Property Taxes $1,263$15,156
Electricity $459$5,513
Total$20,132$241,584
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$690,240/yr
40% on housing$603,960/yr
45% on housing$536,853/yr

Massachusetts FAIR Plan Programs

Massachusetts Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 213,928Commercial: 230
Total Premiums$400.85M
Total Exposure$115.57B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 8.7%
8.7%
0%30.0%
Electricity Growth Rate10-year average: 7.9%
7.9%
0%15.0%
Property Taxes Growth Rate2-year average: 2.7%
2.7%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$1,414This listing

vs Other Active Listings

Avg $/sqft

ZIP 02568$1,023
Dukes County$1,020

vs Homes Sold Last Month

Median $/sqft

ZIP 02568$665
Dukes County$616

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

Price History

DateEventPrice
2026-07-22Listed for sale$3,295,000

For Sale by Agent

AgentMadelyn Silvia
BrokerageWallace & Co. Sotheby's International Realty

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