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There’s much to be done in the months before you retire — determining how much you can safely withdraw from your retirement accounts, researching your Social Security claiming options, and stress testing your budget to ensure that your projected income will cover your monthly bills. (Learn more: What to do one year before you retire)
But financial professionals suggest it may also be prudent to prepay for certain items before you leave the workforce, which can help reduce your future expenses and potentially improve your retirement experience.
“I often encourage clients to look at big-ticket or predictable expenses while they still have earned income, because it’s generally easier to handle them when cash flow is higher and borrowing capacity is stronger,” said Jason Sebell, a wealth management professional with Baystate Financial in Boston. “The key may be to avoid entering retirement with unnecessary financial strain or high-interest debt.”
Things to consider paying for before you retire include:
- Your house — or vacation home.
- Dental and vision services.
- Elective surgeries, including hip or knee replacements.
- Major home repairs and age-in-place upgrades.
- A low-maintenance car (or RV) that you pay in full.
- Bucket list expenses.
Your house — or vacation home
If you dream of downsizing to a more accessible home, relocating to a tax-friendly state, or buying a vacation property when you retire — and you need a mortgage to do it — it may be wise to close on the property before you retire. Why?
You’ll find it easier to qualify for a loan when you’re still employed. You may also be able to borrow more. Indeed, lenders reserve their most favorable interest rates for borrowers with a proven income stream and solid credit history. (Learn more: Why boomers should get a mortgage while they’re still working)
“The time to move isn’t when you have to, it’s when you want to — and still have the income to make it seamless,” Sebell said.
Homeowners who plan to stay put, on the other hand, and are still chipping away at their loan, may instead choose to pay off their mortgage before they exit the workforce, especially if their monthly payment would tax their projected retirement income stream.
“Retirees typically want as little financial stress as possible,” said Paul Tokarz, co-managing partner of WestPoint Financial Group in Chicago, Illinois. “The ability to plan appropriately before you actually pull the trigger on retirement can allow you to have less worries.”
Keep in mind that there are potentially good reasons to maintain a mortgage too.
For example:
- You might earn more by keeping those dollars invested in the market, although that involves risk.
- You may also wish to offset your taxable income with the mortgage interest deduction.
- Or, you may wish to retain liquidity. Stocks can be easily sold if you experience a financial hardship, unlike real estate, which can take months or years.
A financial professional can offer guidance tailored to your unique financial goals on whether it might be wise to pay off your home or maintain a mortgage as you head into retirement. (Related: Should I be retiring with a mortgage?)
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Dental and vision services
The cost of dental and vision care can add up fast, even for those with health insurance.
Medicare (Part A and Part B) typically does not cover dental services, such as cleanings, fillings, tooth extractions, or items like dentures and implants, although some Medicare Advantage (Part C) plans may help foot the bill.
Medicare is the federal health insurance program covering those age 65 and older, certain younger people with disabilities, and those with end-stage renal disease.
Dentures alone can range from $450 for a low-cost set to $6,500 for a premium set, which may be partly covered by separate dental insurance or a Medicare Advantage plan.1
And dental implants can cost far more — between $3,000 and $4,500 per tooth. Those who need a mouthful of implants may be facing a bill of anywhere from $60,000 to $90,000, according to Forbes.2
As for vision care, including routine eye exams, eyeglasses, contact lenses, and laser eye surgery, original Medicare doesn’t cover that either.3 It may, however, cover certain eye care services if you have cataracts or glaucoma. Medicare Advantage plans may offer additional benefits.
LASIK eye Surgery alone to correct vision costs from $1,500 and $5,000 per eye.4
In some cases, your employer-sponsored health insurance plan may offer more comprehensive coverage and potentially lower out-of-pocket costs, not to mention paid leave during your recovery.
While you are working, you may be able to reduce the cost of health care services further still by using your workplace flexible spending account or health savings account, which are pretax accounts funded with payroll deductions, to pay for that care.
“Medicare is excellent for many things, but not comprehensive; dental, vision, and elective surgeries are blind spots people tend to forget until it’s too late,” said Sebell.
Elective surgeries — including knee or hip replacements
For the same reasons, you may wish to consider knee or hip replacement surgery before you retire if your doctor has suggested it is imminent.
But first compare your current health insurance benefits with your future coverage under Medicare to determine which may offer better benefits. Those with Medicare coverage can expect to pay roughly $2,000 in out-of-pocket costs for knee or hip replacement surgery, according to the Centers for Medicare & Medicaid Services.
Money, of course, is not the only (or even primary) factor where health decisions are concerned. You should also consider your health, your age (replacement parts may only last 15 or 20 years), your pain level, and above all else, your doctor’s advice.
Major home repairs and age-in-place upgrades
Regardless of how active you are, you’ll be spending more of your time at home after you retire. Now is the time to complete costly repairs and updates that will help you age in place.
The average cost of a new roof is roughly $26,000 for a 2,000-square-foot home. However, costs can range from $9,858 to $41,822 depending on the materials, roof complexity, and your location, according to This Old House.
And modifications that specifically improve safety and functionality for seniors can set you back $10,000 to $50,000 … or more. According to AARP, those might include:5
- A first-floor bedroom with full bathroom.
- Step-free showers.
- Slip-resistant floors.
- An easy-access kitchen.
- No-step entries.
- Wider doorways for wheelchair access.
- Easy-grasp lever-style handles instead of doorknobs.
A low-maintenance car that you pay in full
Nearly-there retirees might also consider trading in their older car for a low-maintenance newer one that they pay in full, especially if their current vehicle is showing signs of wear and tear.
That’s especially true if your retirement plans involve road trips.
A paid-off car can simplify your finances, save you money on interest, and provide peace of mind as you transition into retirement. It also frees up disposable income that you can apply to other goals.
“Cars don’t last forever — better to buy one when your paycheck can qualify you than when your portfolio has to,” said Sebell.
That said, you should only consider paying off a car or RV if you can afford to do so without robbing your emergency fund, or leaving yourself financially vulnerable.
If you can’t afford to do so or wish to keep your current car until repairs become too costly, consider starting a separate account where you save every month for a future vehicle purchase.
Bucket list expenses
Hopefully, your retirement plans involve a little adventure.
Some dream of a full-family safari in Africa, renting a cabin for a summer to write a book, or realizing their dream of becoming a pilot. You may not be able to do it all, but you are far more likely to hit the highlights if you plan ahead.
Start by making a wish list and rank each experience by level of interest. Then, do some research to determine the projected cost.
Ideally, Tokarz said, retirement savers should begin setting discretionary money aside as early as possible, which will enable them to book those vacations guilt-free.
“This should be years in the making,” he said. “It takes time and discipline to properly create accounts that can fulfill future bucket list items. All the more reason to start planning well ahead of retirement.”
Sebell agrees.
“My mother is 76 and is checking off items on her bucket list without guilt or anxiety, funded by the cash value in her permanent life insurance policy, which she purchased when she was younger,” he said. “She used her tax-free withdrawals last year to visit Scandinavia, Jamaica, Mexico, and Italy.”6
Preretirees, he adds, should earmark savings for lifestyle goals as much as necessities: “Retirement isn’t just about paying bills — it’s about living the life you worked for. Allocating a ‘fun fund’ for bucket list items can ensure those dreams don’t get sidelined by day-to-day — or unplanned for — expenses.”
Conclusion
Getting a jump on your future expenses, both needs and wants, can help make your transition into retirement much less stressful and a lot more fun.
It may also provide clarity on how far your retirement savings may stretch and where your priorities lie. And that’s worth its weight in gold.
“In retirement, financial peace of mind can be worth a lot more than almost any return on investment,” said Sebell.
Discover more from MassMutual…
Health Savings Account for retirement planning: Pros and cons
The ideal retirement withdrawal rate
Need a financial professional? Find one here
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1 CareCredit.com, “How Much Do Dentures Cost? Average Price by Type and State,” Oct. 17, 2025.
2 Forbes, “How Much Do Dental Implants Cost in 2025,” Jan. 16, 2024.
3 Medicare.gov, “Eye exams (routine).”
4 LASIK.com, “How Much Does LASIK Cost in 2025,” Oct. 13, 2025.
5 AARP, “Universal Design Tips for Homeowners,” July 6, 2023.
6 While permanent life insurance policies can provide cash value that may be accessed for various purposes, it’s important to remember that the primary purpose of life insurance is to provide a death benefit to beneficiaries. Borrowing or taking withdrawals from cash value will reduce the policy's cash value and death benefit, increase the chance the policy will lapse, and may result in a tax liability if the policy terminates before the death of the insured. Withdrawals are only tax-free up to the cost basis of the policy
