Tax Talk: Capital Gains Tax Rules for Wisconsin Second Home (2025)

Tax Talk: Capital Gains Tax Rules for Wisconsin Second Home (2025)

Investment & STR Eric Hegwer

Selling a luxury property in Door County often results in a significant profit, but without proper planning, a large portion of that equity can be swallowed by taxes. Second homes are treated differently than primary residences. You don’t automatically get the standard $250,000/$500,000 exclusion. This guide breaks down the current capital gains tax rules for Wisconsin second home sales, including the federal brackets and Wisconsin’s unique state-level deductions.

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Investor’s Guide to Sister Bay 4-Bedroom Limit STR Regulations

Investor’s Guide to Sister Bay 4-Bedroom Limit STR Regulations

Investment & STR Eric Hegwer

A common mistake new investors make in Sister Bay is assuming a large house means large income. You might buy a beautiful 5-bedroom waterfront home, only to discover your rental permit is limited to 8 people or fewer. This guide explains the difference between a home’s size and its legal rental occupancy, which is the key to maximizing your short-term rental (STR) income.

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The True Cost of Property Management Door County STR (Hidden Fees)

The True Cost of Property Management Door County STR (Hidden Fees)

Investment & STR Eric Hegwer

New investors often look at the gross rental income and think, “I’m going to be rich.” Then the monthly statement arrives. Between commissions, cleaning fees, and surprise maintenance markups, your profit margin can shrink fast. Understanding the true cost of property management is the difference between a profitable asset and a money pit. Learn more about the Cost of property management Door County STR in this article.

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Investment Niche: Why Little Sturgeon Bay waterfront investment property is the way.

Investment Niche: Why Little Sturgeon Bay waterfront investment property is the way.

Investment & STR Eric Hegwer

While most investors fight over million-dollar listings in Fish Creek, a quiet revolution is happening further south. Little Sturgeon Bay is quickly becoming the smart money play for waterfront investment. Why? It offers a lower entry price and a true 12-month rental season fueled by a massive ice fishing economy.  Learn all about Little Sturgeon Bay waterfront investment property.

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How to Win 5x Rental Income in Baileys Harbor Investment Homes

How to Win 5x Rental Income in Baileys Harbor Investment Homes

Investment & STR Eric Hegwer

Baileys Harbor offers a top chance to make strong rental income. Buyers call this town the “Quiet Side” of Door County. It sits on the powerful Lake Michigan shore. You find large, secluded homes here that tourists love. The town often has easier rules for rentals than other busy villages. We help you find the best Baileys Harbor Investment Homes that give you the highest return. Use this guide to learn how to make money from your high-end property.

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