Highest-priced ski market on the Top 50 — Winter Park STRs command a $3M median because they're trophy-tier mountain homes with deep amenity stacks. Colorado's full §168(k) conformity plus a 83% Diamond density on high-basis properties means the absolute-dollar Year 1 deduction ($782k median) is one of the largest on the list. Ski-resort amenity mix drives the 15-year improvement basis.
Winter Park requires STR registration under Chapter 10 of the Town Code plus a mandatory East Grand Fire District Life & Safety Inspection every 12 months (Ordinance 624); a $400-per-bedroom annual affordable-housing surcharge (Ord. 605) applies on top of the $150 base fee. Permit: Yes · Cap: — · Min stay: None · Owner-occ.: No. Verified 2026-08-16 against primary jurisdiction sources — read the full regulations profile →
Colorado fully conforms to federal §168(k). Investors capture the entire Year-1 federal deduction plus Colorado state-level tax savings against Colorado's income tax. The state layer is additive, not subtractive.
Strongest Diamond-density STR profile in the Northeast — a third of Winter Park short-term rentals hit ≥24% bonus-eligible % of purchase price. Cabin and lake-house amenity stack drives the 15-year improvement basis; state conformity state conformity reduces state-level benefit slightly, but federal Year 1 deduction is among the strongest on the list.
Winter Park STRs lean heavily on the amenity categories the IRS classifies as 15-year land improvements: hot tubs, fire pits, outdoor kitchens, pergolas, and lake docks — all 100% bonus-eligible in Year 1 under §168(k). That amenity density pushes market-median bonus-eligible % to 26.1%, second only to Lake Cumberland KY (26.9%).
Only partially. Colorado allows federal bonus depreciation to flow through, but adds back a portion at the state level and spreads it over a longer recovery period. The federal Year-1 deduction is unaffected — this is still a strong federal market — but the state portion of the savings is smaller than in fully-conforming states. PA-resident investors should model the state-federal split with their CPA before purchase.
Prevalence of 15-year land improvements we typically see across Winter Park short-term rentals — all 100% bonus-eligible in Year 1 under IRS §168(k):
The three markets share a similar bonus-eligible % profile in the DepreciMax Top 50 — the differentiation is rank, price point, and state §168(k) conformity.
| Market | Rank | Diamond Density | Median Bonus % | Median Y1 Deduction | State Conformity |
|---|---|---|---|---|---|
| Winter Park, CO | 5 | 83% | 26.1% | ~$782k on $3.00M STR | Full |
| Lake Cumberland, KY | 1 | 92% | 27.1% | ~$94k on $347k STR | Full |
| Driggs, ID | 6 | 83% | 26.1% | ~$343k on $1.31M STR | Full |
Deeper comparative reading: Smoky Mountains vs. Blue Ridge vs. Winter Park: STR bonus depreciation showdown.
Winter Park spans 4 primary sub-markets with materially different STR economics. The calculator below has a zip dropdown — switch it to your area. The bonus-eligible percentage (Winter Park's market-typical 26.1%) stays constant across zips because it reflects the property type, not the location. state conformity — federal deduction is the primary benefit.
See IRS Publication 946 for §168(k) rules. Use the interactive calculator below to model your specific deal.
Looking for a deeper read on your specific property, not just the market median? Run the $99 Winter Park property report — our AI analyzes 7–9 listing photos against the IRS classification rules and returns a line-item §168(k) estimate closely calibrated to a formal $5K–$8K cost seg study.
Three live Winter Park listings spanning entry, mid, and high price tiers. Year 1 deduction is estimated as a range around the Winter Park market bonus-eligible average (26.1% ± 3 percentage points). Click any card to run a full property report to tighten to one exact number.
The market-median numbers on this page are a screening tool, not a final answer. Here's how STR investors and their CPAs actually convert a market rank + median bonus-eligible % into an underwriting number for a specific offer.
For further reading on the pre-offer bonus-depreciation workflow, see how to use §168(k) before closing on a short-term rental. To catch missed prior-year bonus depreciation using Form 3115, see the Form 3115 catch-up guide.
Verified as of 2026-08-16 against primary jurisdiction sources. See the full Winter Park STR regulations page for jurisdiction breakdown, ordinance section numbers, and 5-question FAQ.
Read the full Winter Park STR regulations profile →Verified as of 2026-08-16 against primary jurisdiction sources. See the full Winter Park STR regulations page for jurisdiction breakdown, ordinance section numbers, and 5-question FAQ.
Read the full Winter Park STR regulations profile →Winter Park's #5 rank comes from the DepreciMax Top 50 methodology: we score every active STR-suitable listing across the nation's most-watched STR markets on land value, state §168(k) conformity, and amenity mix, then rank markets by the median bonus-eligible % of their active listings. Individual property estimates are closely calibrated to a formal cost segregation study.
More detail in the Top 50 Markets methodology section.
Run any active Winter Park listing through the DepreciMax property scorer. Free market search shows you every listing ranked by bonus depreciation potential. $99 per detailed AI report on a specific property — closely calibrated to a formal cost seg study.
Score Winter Park Properties →All 50 markets ranked by bonus depreciation score, with category filters and the full methodology.
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