265 S Highland StWinchesterKY40391



INVESTMENT ANALYSIS
Investment Verdict
Appreciation PlayInvestors who prioritise long-run asset value over immediate income should consider 265 S Highland St, Winchester, KY, 40391 in Winchester. Rental yield 3.87%. At $505,000 with 3.87% gross yield, current distributions are modest, but the 5% appreciation rate projects $139,522 in new equity by year five, complemented by $4,651/yr in principal paydown. Ziffy Mortgage's DSCR loan (0.72) allows non-U.S. residents to acquire without W-2s or domestic credit. Total projected five-year cumulative return: $98,269.
| This Property | City Avg | |
|---|---|---|
| Gross Rental Yield | 3.9% | 8.0% |
| Monthly Cash Flow | $(1,445) | $150 |
City averages based on Winchester market data in our database. Property projections are estimates.
DSCR Loan Qualification
| Monthly Rental Income | $1,628 |
| Total Monthly Debt Service | $2,873 |
| DSCR Ratio | 0.57x |
Ziffy Mortgage typically prefers a DSCR of 1.0+, but in some cases you may qualify with a DSCR below 1. To explore if this deal qualifies for an investment mortgage, book time with your loan officer →
Estimates assume 6.0% rate / 30-yr fixed, 30% down, 1% tax, 0.5% insurance. Not a commitment to lend.
Multi Family
Built in 1940
6,098 sqft lot
$N/A/sqft
No HOA
Neighborhood Data
Neighborhood data shown for ZIP Code: 40391, Winchester, KY area.
Housing Distribution
Housing Statistics
| Category | Value |
|---|---|
| Total HU (Housing Units) | 16,374 (100%) |
| Owner Occupied HU | 10,285 (62.8%) |
| Renter Occupied HU | 4,824 (29.5%) |
| Vacant Housing Units | 1,265 ( 7.7%) |
| Median Home Value | $223,867 |
| Average Home Value | $258,919 |
Housing Distribution
Address Breakdown
Residential
15,316
Single Family
15,081
Multi-Family
235
Businesses
872



Nearby investment properties with comparable rents
Nearby investment properties with comparable prices

Ziffy AI Summary
A quick, investor-focused snapshot highlighting income strength, yield potential.
| Key metrics | Value |
|---|---|
| Price | $399,900 |
| Est. Rent | $3,200/mo |
| ROI | 18% |
- Attractive rent-to-price ratio for income stability
- Good fit for DSCR financing with healthy coverage


Multi Family
Built in 1940
6,098 sqft lot
$N/A/sqft
No HOA
Neighborhood Data
Neighborhood data shown for ZIP Code: 40391, Winchester, KY area.
Housing Distribution
Housing Statistics
| Category | Value |
|---|---|
| Total HU (Housing Units) | 16,374 (100%) |
| Owner Occupied HU | 10,285 (62.8%) |
| Renter Occupied HU | 4,824 (29.5%) |
| Vacant Housing Units | 1,265 ( 7.7%) |
| Median Home Value | $223,867 |
| Average Home Value | $258,919 |
Housing Distribution
Address Breakdown
Residential
15,316
Single Family
15,081
Multi-Family
235
Businesses
872
Nearby investment properties with comparable rents
Nearby investment properties with comparable prices



Listed by: N/A • N/A
Mls Name: Imagine MLS
Mls ID: #26004961








