A leased estate in Windermere rarely pays for itself. Houses worth $1.5 million or more listed for lease in Windermere, Dr. Phillips, Bay Hill and Winter Park in October 2026 asked a median 5.6% of their estimated value a year. On a $2,000,000 house bought with 20% down at 7.40%, that rent pays the tax, insurance and upkeep and about 32% of the mortgage. Over ten years the purchase makes money only if the house appreciates more than about 3.3% a year.
Every starting figure below can be changed, and each one says where it came from.
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Cap rate is the rent left after every operating cost, divided by the price, before the mortgage. When it sits below the mortgage rate, each borrowed dollar costs more than the house earns on it, and more debt makes the monthly number worse. At a 5.6% gross yield and a 7.40% rate, it is below the rate before a single cost comes out.
Rent to break even is the monthly rent at which the house covers its mortgage and every carrying cost. Compare it with leased comparables, not asking rents.
The hold-period figure is what you walk away with at the sale, plus or minus each year's cash flow, against the cash you put in. Outside Miami-Dade, Florida's deed stamps alone are 70 cents per $100 of the sale price, $14,000 on $2,000,000, before commission.
What it leaves out: income tax, depreciation, furnishing, and the months before the first lease. Owners who hold one of these houses as a rental usually want management built around preservation rather than rent roll.
On cash flow, rarely. On October 15, 2026, the 24 houses worth $1 million or more listed for lease on Redfin in Windermere, Dr. Phillips, Bay Hill and Winter Park asked a median 6.5% of Redfin's estimate of their value a year, and the six worth $1.5 million or more asked 5.6%. Those are asking rents, not signed leases. With 20% down at 7.40%, that rent on a $2 million house covers its carrying costs and about a third of the mortgage. Owners at this level hold for the land and the appreciation.
Usually, within the declaration. Under Fla. Stat. § 720.306(1)(h) a homeowners' association may amend its governing documents to prohibit or regulate leases shorter than six months and may prohibit renting a parcel more than three times in a calendar year; those two apply to every owner. Other rental restrictions enacted after July 1, 2021 apply only to owners who take title after they take effect, or who consent. A condominium falls under chapter 718 instead. Read the declaration before you price the lease.
A rental gets no homestead exemption, so the bill runs on the full assessed value, which for a recent purchase sits close to the price. The 2025 total millage was 15.2311 in the Town of Windermere (15.4839 inside the Water & Navigation district), 16.3894 on the Isleworth and Keene's Pointe parcels we checked, which sit inside that district, and 15.3615 in Winter Park: about $30,500, $32,800 and $30,700 a year on $2,000,000.
The 2025 average surplus-lines HO-3 premium in Orange County was $8,900 for a dwelling insured between $1 million and $5 million, Coverage A only (FSLSO). That is an owner-occupied form; a leased house is written on a landlord policy and priced separately. The band follows replacement cost, not price. Citizens cannot write a dwelling with a replacement cost of $700,000 or more outside Miami-Dade and Monroe, so a house with that replacement cost is placed privately. Flood is a separate policy.
Income tax, depreciation, furnishing, and the months before the first tenant moves in. Your CPA runs the tax side. The rent is the number most worth checking: send us the address and we price it against leased comparables in the MLS.
Nothing on this page is tax, legal or investment advice. The calculator runs before income tax and depreciation. The public data it starts from is linked below. The rent figure is the median asking rent on Redfin's October 15, 2026 listings, measured against Redfin's own estimate of each home's value; asking rents run above signed leases. Maintenance and commission are placeholders with no published source.
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