Real Estate Investing in Winona, Missouri (65588)

Everything the listing leaves out — vacancy, rent trend, cap rate, landlord climate. All free.

Shannon County • Population: 2,025 • Data updated: September 2026

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Should you buy in 65588 (Winona, MO)? Our answer, based on the numbers below.

🏠 For Homebuyers
MIXED
Grade C (57/100)

Mixed signals — some positives, some negatives. Worth considering but not a slam-dunk.

📈 For Investors
MIXED
3.0 / 5 (52/100)

A cash-flow market — rent-to-price math works from day one, though value growth is modest. Great for income-focused investors.

⚠️ Risks to Know
2 flags
  • High vacancy: 17.4% of homes vacant — above national norms.
  • Lower household income: $38,365 median — tenant affordability is tighter.

• Modeled rent — no observed market rent for this ZIP; the figure is estimated from HUD fair-market rent.

What’s happening in Winona, MO (65588)?

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3.0/ 5

Investability

Overall investment appeal

2.0/ 5

Appreciation

Long-term value growth

4.0/ 5

Cashflow ROI

Rental yield potential

Avg Home Value $146,697
Avg Monthly Rent $846
1% Rule ✗ Does Not Meet
Median Income $38,365
% Renters 15.8%

Market Analysis: 65588 Winona

Put differently, ZIP 65588 has challenges — vacancy pressure, softer price growth, and tenant stability concerns sit alongside the $147K median. It rewards specialists, not generalists.

The investment case in 65588 is notable only for operators who understand what they are buying. A $147K median suggests accessibility, but management intensity, vacancy drift, and capex surprises are real.

Nearby ZIPs in Winona have seen price recovery that 65588 has not matched. Shannon County data supports the view that the spread is structural rather than temporary.

Resident income in 65588 sits below the county median. That reality colors rent collection, vacancy, and reinvestment math in ways that outside investors often underestimate.

Experienced landlords with local relationships tend to find 65588 workable. Turnkey investors from out of state usually find the numbers do not hold up in practice.

Explore the Data — Click a Tab Below
🏦 Current 30-yr Fixed Mortgage Rate: 6.76% as of Sep 10 Source: Freddie Mac PMMS

Here's what matters if you're considering buying a home in Winona:

C Below Average
Buy Confidence Score: 59/100
Affordability
15/25
Appreciation
14/25
Stability
7/20
Timing
8/15
Rental backup
15/15
Affordability
Moderate
Homes cost 3.8× the median income
Value Trend
Declining (-1.1%)
How home values changed in the past year
Rental Backup
Strong
Could rent for $846/mo if you need to move
Market Conditions
BALANCED
Even conditions for buyers and sellers
Bottom Line: This market may be challenging for buyers. Consider your timing and budget carefully.

Market Trends

Home Value History (with trend line)

$169K$153K$137K$120K$104K$88KJun 2016Jul 2021Jul 2026

📊 How Does 65588 Compare?

Metric 65588 Winona Missouri
Home Value $146,697 $146,697 $254,657
5-Year CAGR 2.6% 2.6% 7.0%
Avg Rent $846 $846 -
Cap Rate 4.5% 4.5% -
💡 Why Invest in 65588? Click to expand

With a 3/5 investability rating, this ZIP shows solid fundamentals for buy-and-hold investors.

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Landlord Ground Truth

Real numbers from people who own or manage rentals in ZIP 65588 (Winona, MO). Anonymous, moderated, never written by AI.

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Investability
Good
Cap Rate
4.5%
Fair
5yr Growth
+2.6%
Slow

📊 Market Snapshot

Home Value $146,697
Monthly Rent $846
Price-to-Rent 14.5:1
1% Rule ✗ Fails

💰 Return Metrics

Gross Yield 6.9%
Cap Rate 4.5%
5-Year IRR 7.1%

📈 Home Appreciation

1-Year -1.1% ▼
3-Year CAGR -1.9% ▼
5-Year CAGR +2.6% ▲
10-Year CAGR +3.8% ▲

🏠 Rent Trends

1-Year N/A
3-Year CAGR N/A
5-Year CAGR N/A
Negative Leverage — IRR / Tax Play Cap Rate: 4.5%  |  30yr Rate: 6.8%
Leverage reduces cash returns at current rates.

The current 30-yr mortgage rate (6.8%) exceeds the estimated cap rate (4.5%). Financing reduces your cash-on-cash return below the cap rate. Markets like this may still make sense as IRR plays — factoring in appreciation, depreciation, and a future refinance when rates drop.

Run an IRR Analysis →

⚠️ Risk Signals

Composite view of factors that can impact a ZIP's stability and your downside risk.

Vacancy
17.4%
Elevated risk
Landlord Climate
5.0/5
Friendly
Value Trend (5yr)
+2.6%
Stable
Eviction process: Fast Rent control: Favorable

Demographics in 65588

Population: 2,025

💰 Median Household Income
$38,365
This area
$38,365
State
$62,768
USA
$74,580
🏠 Renter Occupied
15.8%
This area
15.8%
State
23.7%
USA
34.0%
💼 Unemployment Rate
1.2%
This area
1.2%
State
-8.1%
USA
3.7%
🎓 College Educated
13.5%
This area
13.5%
State
8.6%
USA
33.7%
👤 Median Age
55.3 years
This area
55.3 years
State
20.4 years
USA
38.9 years
🏚️ Vacancy Rate
17.4%
This area
17.4%
State
18.8%
USA
10.5%
👥 Population by Ethnicity
White 88.9%
Other/Mixed 9.6%
Hispanic/Latino 1.2%
Asian 1.1%
Black/African American 0.3%
👶 Under 18
17.2%
This area
17.2%
USA
22.0%
👴 65 and Over
28.9%
This area
28.9%
USA
17.3%
📊 Poverty Rate
3.5%
This area
3.5%
USA
11.5%

Crime & Safety

🚧

Crime & Safety Data Coming Soon

We're integrating comprehensive crime statistics including violent crime rates, property crime, and safety scores to help you make informed investment decisions.

Expected: Q1 2025

🎓 Schools in 65588

B+ Avg School Grade
2 Schools
11.6:1 Avg Class Size
$11,423 Avg Per Pupil

Schools in This ZIP Code

B+ Above Average

WINONA ELEM.

📚 Pre-K – 08 School
👥
313 Students
👨‍🏫
12.6:1 Class Size
💰
$11,423 Per Student
B+ Above Average

WINONA HIGH

📚 09 – 12 High School
👥
127 Students
👨‍🏫
10.6:1 Class Size
💰
$11,423 Per Student
About Repit School Scores

Traditional school ratings rely heavily on standardized test scores, which often reflect family income more than school quality. Repit takes a different approach.

We evaluate schools based on factors that research shows actually impact educational outcomes:

  • Class Size — Smaller classes mean more individual attention
  • School Funding — Resources available for programs, staff, and facilities
  • Community Factors — Neighborhood characteristics that influence student success
  • School Environment — Size, type, and structure

Scores are updated annually using federal education data.

Frequently Asked Questions

Is rental property easy to operate in Winona, MO?

For rental operators, Winona, MO rates as landlord-friendly. The regulatory environment standard buy-and-hold operations.

What is the typical renter like in Winona, MO?

The tenant pool in Winona, MO is solid, supported by local employment and population fundamentals. Rents of $846/mo are well-absorbed by the market.

What are home prices like in Winona, MO?

Expect median prices around $147K in Winona, MO. The market has run at a 0.0% 5-year CAGR, so entry costs have been stable.

Can I live-in-and-rent in Winona, MO?

House hacking in Winona, MO is reasonable to execute. Prices around $147K and rents of $846/mo solid owner-occupant economics.

Is Winona, MO a good market for buy-and-hold investors?

The 3.0/5 investability rating in Winona, MO reflects its $147K prices and $846/mo rents. Investors generally consider it a solid option within MO.

You know 65588 now. You don’t know where it ranks.

This page stays free — all of it. What one page can’t tell you is how 65588 compares to every other market. Investor ($19/mo) screens every U.S. ZIP by cap rate, the 1% rule, vacancy and landlord climate, and exports your shortlist.

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