Buying a home is supposed to be one of the most exciting purchases of your life. You tour it, fall in love with the kitchen, imagine your future there and start mentally arranging furniture before making an offer. But sometimes what looks great on a sunny Saturday in July becomes what you complain about every Tuesday morning in January. We don’t always regret the homes we buy โ we regret what we didn’t think about first.
The house with everything โ and the terrible driveway
That steep driveway looked charming when you toured the house in 90-degree sunshine. โA little slope never hurt anybody.โ
Fast-forward to January. It’s 25 degrees, the driveway is covered in ice and you’re sitting at the bottom wondering whether your Subaru has enough traction to make it to the garage. Suddenly, that tile shower in the guest bathroom seems less important. A home needs to work for you in every season.
The nicest house on the block
It’s tempting to stretch your budget for the nicest home in the neighborhood. The problem is that you don’t control everything outside your property line. Maybe the house next door is a rental and the tenants treat it like one. Maybe the surrounding properties aren’t maintained the way yours is and that bothers you more than you expected. You may have bought the nicest house, but you’re still living in the neighborhood.
Sometimes the better investment โ and lifestyle โ is the least impressive house in a great neighborhood.
The yard you thought you wanted
A beautifully landscaped yard can sell a house in about 30 seconds. Green grass, mature trees, flower beds, a garden, maybe even a water feature. You picture summer barbecues and leisurely Saturday mornings.
Then you realize they probably hired a landscaping company to make it look that good โ and now you have to maintain it. Maybe you think you love yard work until it’s 90 degrees, you’re pulling weeds, and suddenly that landscaping company seems necessary. Buy the lifestyle you actually want, not the one you imagined while touring a property.
โWe can just tear that wall outโ
This is one of the great promises of homeownership: We’ll just remodel it. Maybe you’ve built the project into your budgetโuntil you move in, your ceiling starts leaking, and suddenly that remodel is on hold. That small house with a great lot might seem like the perfect compromiseโ until you have kids, a home office and approximately 400 more things than you owned five years ago. Suddenly, โwe’ll make it workโ becomes โwe need another bedroom.”
The house that’s a better dealโjust not where you want to live
Central Oregon makes this particularly relevant. Maybe you can get significantly more house in a surrounding town than you can in Bend. On paper, it’s hard to argue with the value. But a house isn’t just a house. It’s where you wake up, spend your evenings, grab coffee, meet friends and build your routine. If you moved to Central Oregon because you love Bend’s lifestyle, saving money may not feel like a bargain if you’re no longer enjoying it.
Buy the house for your life, not your imagination
The best home isn’t necessarily the biggest, newest, nicest or best deal. It’s the one that fits the life you actually live โ and the life you’re reasonably likely to live in the years ahead. The house that looks perfect on the day you buy it can look very different after a few winters, landscaping bills, kids and a few thousand trips up and down that driveway.
Low:

1930 SW 27th Street, Redmond
3 bed, 2 bath, 1,379 square feet, .31 acres lot
Built in 1992
$514,900
Listed by Vincent and Kimberly Bishop of Engel & Vรถlkers Bend | Sisters
Medium:

60965 Ward Road, Bend
3 bed, 2.5 bath, 2,080 square feet, 9.96 acres lot
Built in 2003
$999,999
Listed by James Kinney of Engel & Vรถlkers Bend | Sisters
High:

3154 NW Strickland Way, Bend
4 bed, 3 bath, 2,503 square feet, .18 acres lot
Built in 2023
$1,795,000
Listed by Natalie Nolte of Engel & Vรถlkers Bend | Sisters







