Considering Buying a Second Home? Things to Consider

As the seasons change, many Portlanders start daydreaming about a getaway: a cabin tucked in the trees, a spot near the slopes, or a peaceful coastal retreat.  A second home offers more than just a personal escape – it can be a smart real estate investment. Before taking the plunge, it’s worth considering your goals, budget, and the practical realities of owning multiple properties. Most second homes near Portland fall into one of three broad categories:

Mountain Properties Direct access to world-class skiing at Mt. Hood resorts plus summertime hiking and pristine alpine lakes make this area a prime destination.

Resort Communities like Sunriver, Black Butte Ranch, Bend: These offer built-in amenities like golf courses, bike paths, and community pools. Expect HOA fees and community guidelines, but also professional management options and established rental markets.

Coastal Properties: From beachcombing in the summer to stormwatching in the winter, coastal homes offer year-round appeal in numerous towns with unique character.

CLARIFY YOUR GOALS

Before choosing a second home, clarify your main objective- your priorities will shape the location, property type, and features. Are you primarily interested in a retreat for family and friends, or do you want to rent the property and build equity? When weighing your goals, consider:

Travel Time: Will you realistically make the trip often, or will the home end up sitting empty? If the home will be vacant a significant portion of the time, it may make sense to buy a property with rental potential.

Seasonal Challenges: Will snow, coastal storms, or wildfire smoke impact your ability to access and enjoy the home?

Activities: What activities do you enjoy most and want to be closest to?

Community & Amenities: Do you need a home with reliable access to groceries, dining, and healthcare, or are you okay with hauling supplies each visit?

Financial Considerations: Some lenders require a higher down payment and offer less favorable interest rates on second homes- make sure to shop around. At the same time, renting the home can offer potential tax benefits, including deductions for mortgage interest, property taxes, maintenance, and depreciation. Consult a tax professional to understand how these rules apply to your specific situation.

RENTAL POTENTIAL AND RULES

If rental income is part of your plan for your second home, it is important to consider potential regulations regarding short-term rentals as well as generating realistic income projections.

• Are short term rentals permitted? Many Oregon cities and counties have strict rules and permits always check before you buy.
• Consider your target rental rate- is it realistic for the area, season, and property type?
• Will projected rental income cover expenses or just help defray expenses, as this will influence your budgeting and financing.
• If you won’t manage it yourself, factor in property management fees, which can run as high as 25-30% for short-term rentals.

UPKEEP AND MAINTENANCE

Like any house, vacation homes still need year-round attention, and coastal and mountain properties can require special maintenance A property manager can help you keep on top of seasonal maintenance needs as well as ongoing chores like snow removal or yard work.

THINKING LONG TERM

Ask yourself: Is this a forever retreat or a shorter-term investment? Your answer will affect everything from how much you spend, to whether you prioritize turnkey convenience, rental potential, or long-term appreciation.

• Think beyond your current lifestyle- how will you use the property in 5, 10, or 15 years? Will changing family dynamics affect usage?
• Is long-term appreciation part of your strategy? If so, popular recreation areas like Bend, Hood River, and established coastal communities tend to maintain consistent buyer interest due to their amenities and lifestyle appeal.
• If you want a property that could eventually become your primary home, how does that affect choices about location, size and price?

A vacation home in Oregon can give you the best of both worlds- your own retreat plus potential rental income- but it’s important to look at the full picture before making the leap. I’m here to help you navigate the options and regulations, and would be happy to discuss your second home goals and explore what’s currently available in today’s market.