Dukes County

Dukes County is Martha's Vineyard, and the numbers reflect exactly what you'd expect from one of the most expensive resort markets in the country. The median home price sits at $1,559,624, which is nearly double the next most expensive neighbor in this dataset, and the year-over-year appreciation of 3.1% is steady rather than explosive. The cash flow score is 0 and the cap rate comes back at 0, meaning the model cannot produce a workable yield at this price point against prevailing rents. The overall score of 47 and a national percentile of 17 confirm what the raw numbers already show: this is not a market where you buy for income. It is a pure appreciation and asset-preservation play, and even on that axis, you need to be comfortable parking $1.56 million in a market with a population of roughly 20,500 permanent residents.

The investor this market suits is narrow and specific. If your thesis is income, stop here; the cash-on-cash return is effectively zero at the modeled purchase price and a 6.85% rate on a $1.56 million asset. The debt service alone on an 80% LTV loan is a number that no realistic long-term rental on the Vineyard will cover. The appreciation score of 80 is the only compelling figure in the dataset, and it speaks to a market where price appreciation has historically been driven by constrained land supply, ferry-limited access, and high-net-worth demand, not by local employment or household income growth. The buyer who belongs here is someone deploying equity, not leverage, someone who can hold without relying on rent to service the asset and who values low-volatility appreciation in a physically constrained geography over annual yield.

The economic context for Dukes County is unlike any other county in Massachusetts. A permanent population of just 20,543 means the rental demand pool is thin and highly seasonal. There are no economicAnchors provided in the data, which is itself telling; the county's economy is tourism-dependent and service-oriented, without the kind of institutional employment base, university system, or corporate anchor that generates year-round rental demand in mainland Massachusetts markets. That seasonality cuts both ways: short-term rental income from summer visitors can be substantial, but that is a different underwriting model than the buy-and-hold analysis this tool is built around. A long-term residential tenant base this small carries real concentration risk; you are not operating in a deep market.

On carry costs, the monthly tax and insurance figure of $1,937 is material even before you touch mortgage, maintenance, or vacancy. That reflects the state-average effective property tax rate of 1.23%, which the model flags as normal, combined with a 0.26% insurance rate on a $1.56 million asset. Critically, 1.23% is a state-average estimate from Tax Foundation 2024 data, and actual rates at the county or township level on Martha's Vineyard may differ. On a property of this value, a modest variance in the effective rate, up or down, moves the annual tax figure by thousands of dollars, so pulling the actual assessed value and current bill from the Dukes County assessor's office is a non-negotiable step in any underwrite here. At $1,937 per month just for tax and insurance, the carrying cost floor is high enough that even a well-priced rental leaves you feeding the asset every month if you are leveraged.

The specific risk that deserves the most attention here is market depth and liquidity. A permanent population of 20,543 in an island market with no bridge access means that if you need to exit, you are selling to a narrow buyer pool, mostly second-home and resort buyers whose demand is sensitive to broader wealth effects and interest rates. The 3.1% YoY appreciation number is positive but not so high that it compensates quickly for transaction costs and illiquidity. Regulatory risk around short-term rentals is a real concern in resort-dependent Massachusetts markets, though the data does not provide Vineyard-specific ordinance detail. Any investor considering STR income as a bridge to break-even should verify current and pending local STR rules before closing.

Against the neighboring counties in the dataset, Dukes is in a different category entirely. Bristol County at a $524,317 median and a gross rent-to-price ratio of 0.0466 is the most accessible entry point in the comparison set. Suffolk County, which includes Boston, posts the strongest rent-to-price ratio at 0.0531 and a median of $747,013, making it the most income-oriented option among the neighbors listed. Middlesex, Essex, and Norfolk all cluster between $698K and $790K with ratios in the 0.044 to 0.046 range, and all three score 46 versus Dukes at 47, essentially a wash on overall score but at less than half the capital outlay. You choose Dukes over any of these neighbors only if your primary goal is capital preservation and appreciation in a supply-constrained, trophy geography, and only if you can carry the asset without meaningful rental income offsetting the debt. If yield matters at all in your model, every other county in this comparison set offers a better entry point.