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Winter Park

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⭐ STR Status in Winter Park

Orange County unincorporated rules apply; residential zones restrict STR below 30 days

Applicable Rules — Layer by Layer

CASABROVA shows all 4 regulatory layers

1

National

No federal STR law — regulated at city/county level

2

Regional

State frameworks vary — Texas permissive, New York restrictive

3

City

No specific city-level rules — national rules apply

4

District

Orange County unincorporated rules apply; residential zones restrict STR below 30 days

Property Data

Price range/m²

$3,732–$4,633 (₪11,168–₪13,863)

* Exchange rates shown for illustration only, based on ECB mid-market rate. Actual transactions may be subject to conversion fees.

STR Yield

6%–8.5%

STR Status

STR Restricted 🟡

Properties in Winter Park

45 for sale

1

🏠

USD 525K

Winter Park

3 bd194m²

6%–8.5% STR

2

🏠

USD 1.6M

Winter Park

5 bd326m²

6%–8.5% STR

3

🏠

USD 1.9M

Winter Park

5 bd348m²

6%–8.5% STR

4

🏠

USD 470K

Winter Park

3 bd117m²

6%–8.5% STR

5

🏠

USD 1.1M

Winter Park

4 bd255m²

6%–8.5% STR

6

🏠

USD 3.6M

Winter Park

5 bd503m²

6%–8.5% STR

7

🏠

USD 1.8M

Winter Park

4 bd322m²

6%–8.5% STR

8

🏠

USD 799K

Winter Park

6%–8.5% STR

9

🏠

USD 518K

Winter Park

2 bd129m²

6%–8.5% STR

10

🏠

USD 517K

Winter Park

2 bd129m²

6%–8.5% STR

11

🏠

USD 1.1M

Winter Park

3 bd218m²

6%–8.5% STR

12

🏠

USD 487K

Winter Park

3 bd104m²

6%–8.5% STR

13

🏠

USD 517K

Winter Park

2 bd129m²

6%–8.5% STR

14

🏠

USD 2.0M

Winter Park

5 bd391m²

6%–8.5% STR

15

🏠

USD 399K

Winter Park

3 bd175m²

6%–8.5% STR

16

🏠

USD 720K

Winter Park

4 bd221m²

6%–8.5% STR

17

🏠

USD 1.9M

Winter Park

4 bd330m²

6%–8.5% STR

18

🏠

USD 1.4M

Winter Park

5 bd322m²

6%–8.5% STR

19

🏠

USD 650K

Winter Park

3 bd215m²

6%–8.5% STR

20

🏠

USD 633K

Winter Park

3 bd179m²

6%–8.5% STR

21

🏠

USD 687K

Winter Park

3 bd155m²

6%–8.5% STR

22

🏠

USD 199K

Winter Park

6%–8.5% STR

23

🏠

USD 695K

Winter Park

4 bd157m²

6%–8.5% STR

24

🏠

USD 650K

Winter Park

4 bd195m²

6%–8.5% STR

25

🏠

USD 1.6M

Winter Park

3 bd229m²

6%–8.5% STR

26

🏠

USD 560K

Winter Park

3 bd180m²

6%–8.5% STR

27

🏠

USD 615K

Winter Park

3 bd181m²

6%–8.5% STR

28

🏠

USD 589K

Winter Park

2 bd176m²

6%–8.5% STR

29

🏠

USD 525K

Winter Park

3 bd111m²

6%–8.5% STR

30

🏠

USD 338K

Winter Park

2 bd74m²

6%–8.5% STR

31

🏠

USD 2.0M

Winter Park

4 bd343m²

6%–8.5% STR

32

🏠

USD 1.6M

Winter Park

5 bd301m²

6%–8.5% STR

33

🏠

USD 1.1M

Winter Park

4 bd254m²

6%–8.5% STR

34

🏠

USD 870K

Winter Park

3 bd211m²

6%–8.5% STR

35

🏠

USD 105K

Winter Park

6%–8.5% STR

36

🏠

USD 715K

Winter Park

3 bd175m²

6%–8.5% STR

37

🏠

USD 1.6M

Winter Park

4 bd332m²

6%–8.5% STR

38

🏠

USD 385K

Winter Park

3 bd102m²

6%–8.5% STR

39

🏠

USD 615K

Winter Park

3 bd133m²

6%–8.5% STR

40

🏠

USD 1.4M

Winter Park

5 bd218m²

6%–8.5% STR

41

🏠

USD 875K

Winter Park

3 bd248m²

6%–8.5% STR

42

🏠

USD 730K

Winter Park

4 bd164m²

6%–8.5% STR

43

🏠

USD 660K

Winter Park

3 bd169m²

6%–8.5% STR

44

🏠

USD 350K

Winter Park

3 bd154m²

6%–8.5% STR

45

🏠

USD 715K

Winter Park

3 bd236m²

6%–8.5% STR

Properties in Winter Park

45 listings found

Showing 1–12 of 45 listings

4-Bed Villa · 322 m² in Winter Park

$1,750,000(₪5,619,061)

4-Bed Villa · 322 m² in Winter Park

Winter Park, Orlando

villaBuilt 2004

3-Bed Apartment · 194 m² in Winter Park

$525,000(₪1,685,718)

3-Bed Apartment · 194 m² in Winter Park

Winter Park, Orlando

apartmentBuilt 1950

5-Bed Villa · 326 m² in Winter Park

$1,650,000(₪5,297,972)

5-Bed Villa · 326 m² in Winter Park

Winter Park, Orlando

villaBuilt 2026

5-Bed Villa · 348 m² in Winter Park

$1,875,000(₪6,020,423)

5-Bed Villa · 348 m² in Winter Park

Winter Park, Orlando

villaBuilt 2026

3-Bed Apartment · 117 m² in Winter Park

$470,000(₪1,509,119)

3-Bed Apartment · 117 m² in Winter Park

Winter Park, Orlando

apartmentBuilt 1953

4-Bed Villa · 255 m² in Winter Park

$1,150,000(₪3,692,526)

4-Bed Villa · 255 m² in Winter Park

Winter Park, Orlando

villaBuilt 1963

5-Bed Villa · 503 m² in Winter Park

$3,650,000(₪11,719,756)

5-Bed Villa · 503 m² in Winter Park

Winter Park, Orlando

villaBuilt 2008

Apartment in Winter Park

$799,000(₪2,565,503)

Apartment in Winter Park

Winter Park, Orlando

2-Bed Apartment · 129 m² in Winter Park

$517,500(₪1,661,637)

2-Bed Apartment · 129 m² in Winter Park

Winter Park, Orlando

apartmentBuilt 2025

2-Bed Apartment · 129 m² in Winter Park

$516,570(₪1,658,649)

2-Bed Apartment · 129 m² in Winter Park

Winter Park, Orlando

apartmentBuilt 2025

3-Bed Apartment · 218 m² in Winter Park

$1,095,000(₪3,515,927)

3-Bed Apartment · 218 m² in Winter Park

Winter Park, Orlando

apartmentBuilt 1947

3-Bed Apartment · 104 m² in Winter Park

$487,000(₪1,563,704)

3-Bed Apartment · 104 m² in Winter Park

Winter Park, Orlando

apartmentBuilt 1949

Discussions — Winter Park

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Important Legal Disclaimer

The information presented on CASABROVA is for general informational purposes only and does not constitute legal, financial, tax, or investment advice. This information is not binding and should not be relied upon as the basis for any decision. Before executing any transaction or investment in overseas real estate, consult with a qualified lawyer, accountant, tax advisor, and/or any other relevant professional in the relevant territory.

Tax, regulatory, and yield data change frequently. CASABROVA makes efforts to update information weekly from primary sources, but is not responsible for the accuracy of the information or for changes not yet reflected. All figures presented are indicative only.