RANK #5 of 50 Ski
83% Diamond density • 97% Gold-or-better

Winter Park, ColoradoSTR Bonus Depreciation Market Profile · #5 in the DepreciMax Top 50

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.

Median Year 1 Deduction
$781,695
on a $3.00M STR · ~$289k federal tax savings at 37%
This market ranks #6 of 50 in our 2026 STR Bonus Depreciation Market Study.
Representative short-term rental home in the Winter Park market
Median STR Listing Price
$3.00M
Median across active STR-suitable listings. 1,000+ short-term rentals in market.
Diamond Density
83%
Share of Winter Park STR listings that hit Diamond tier (≥24% bonus-eligible % of purchase price).
Bonus-Eligible %
26.1%
Median % of purchase price classifiable as 5-yr or 15-yr property under §168(k).
Federal Savings @ 37%
$289k
Median federal tax savings on a $3.00M purchase.

Winter Park at a glance

Bonus depreciation (IRS §168(k)): a federal tax provision letting investors deduct 100% of qualifying property costs in the year the property is placed in service. For short-term rentals, the deductible portion is the 5-year (personal property) and 15-year (land improvements) components of the total purchase price. See what bonus depreciation is for short-term rentals for the full explainer.
Bonus-eligible %: a DepreciMax metric — the share of a property's purchase price that classifies as 5-year or 15-year property under §168(k), and is therefore 100% deductible in Year 1. Winter Park's market-median bonus-eligible % is 26.1% — meaning a typical $3.00M Winter Park STR generates ~$782k of Year-1 deduction.
The 7-day STR rule: to unlock the "STR loophole" — where bonus depreciation offsets W-2 and other ordinary income, not just passive rental income — the property must average a guest stay of 7 days or less and the owner must materially participate. See how to qualify for the STR loophole.
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Short-Term Rental Regulations — Restricted

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 →

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Colorado State Conformity — Full

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.

Why Winter Park ranks #5 for STR bonus depreciation

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.

What drives Winter Park's high bonus depreciation?

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%).

Does Colorado conform to federal §168(k) bonus depreciation?

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.

Common bonus-eligible amenities in Winter Park STRs

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):

Hot tub or spa
84%
Fire pit / fire feature
61%
Outdoor deck or wraparound porch
71%
Heated mudroom / ski storage
47%
Outdoor kitchen / BBQ area
32%
Sauna or steam room
21%

Winter Park, CO vs Lake Cumberland, KY vs Driggs, ID — bonus depreciation comparison

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 bonus depreciation calculator (by zip code)

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.

Winter Park zip code comparison

Zip Sub-market Land ratio Typical price Typical Year-1 deduction
80482Winter Park Village (highest)High$2995k$782k
80442FraserHigh$1650k$431k
80478TabernashModerate$1200k$313k
80459Kremmling (lowest)Moderate$875k$228k

Sample calculation: $3.00M Winter Park STR (median-priced Lake Harmony listing)

  1. Purchase price: $2,995,000
  2. Winter Park market median: 26.1% of purchase price classifies as bonus-eligible 5-yr + 15-yr property under §168(k)
  3. Year-1 §168(k) deduction: $782k
  4. Federal tax savings at 37% bracket: $64.1k

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.

Representative listings & deductions

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.

How to use this data to underwrite a Winter Park STR deal

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.

  1. Screen the deal against the market median. If a Winter Park listing is priced within the p25–p75 range ($512k–$1,010k) and looks like a typical cabin or lake-house STR, the market-median 26.1% bonus-eligible is a defensible screening estimate. That gives you a Year-1 deduction range you can plug into an initial underwriting model in about 60 seconds — before you invest CPA time or offer-drafting effort.
  2. Adjust up or down based on amenity signals. Winter Park properties with a full outdoor stack (hot tub + fire pit + wraparound deck + outdoor kitchen + pergola) trend toward the Diamond tier at 24–30% bonus-eligible. Properties with minimal outdoor amenities — condos, indoor-only cabins, or properties without lake access — trend toward the Bronze tier at 18–20%. Use the amenity checklist to categorize before you commit.
  3. Model the offer with the deduction baked in. Take the estimated Year-1 deduction × your federal marginal rate (typically 37% for high-earner STR investors) = federal tax savings. Add this to your effective Year-1 cash-on-cash return. On a $3.00M Winter Park STR at 26.1% bonus-eligible, that's ~$289k in federal savings — often 8–12% of purchase price flowing back into Year-1 cash. Colorado's partial conformity means state-level savings are minimal for PA residents, so pure-federal math dominates.
  4. Verify with a $99 property-level report before you sign. Once you're past screening and preparing to make an offer, run the specific property through DepreciMax's photo-analysis pipeline. The $99 report tightens the estimate to a single number, line-items the 5-year / 15-year / 39-year breakdown, and delivers a calibrated Year-1 number closely calibrated to a formal cost segregation study's bonus-eligible %. Your CPA can build the return directly from this output; a formal engineered study (typically $5,000–$8,000) is only necessary post-closing for IRS-defensible filing on very large deductions or high-scrutiny audit risk.

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.

Permit cap
—
Min stay
None
Owner-occupancy
No

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 →
Permit cap
—
Min stay
None
Owner-occupancy
No

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 →

How the rank is calculated

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.

Sources & verification:
Published: 2026-07-12  ·  Last updated: 2026-07-12
Sample listings are real active for-sale listings — actual addresses shown. Bonus depreciation outcomes vary by individual property; this page estimates ranges for typical purchases. Not tax advice — consult your CPA before making investment decisions.

Score live Winter Park properties — for your specific deal

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.

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