Crime & Safety Report for 14755 Masthead Landing Cir, Winter Garden, FL 34787

Review crime and safety information near 14755 Masthead Landing Cir, Winter Garden, FL 34787. HoodScore summarizes nearby reported incidents, registered sex offenders, and neighborhood safety indicators to help buyers and renters perform better location due diligence.

Generated At — 2026-07-27

$580,000 | 4 bd | 2 ba | 2,258 sqft

Distance rings: 1 mi and 2 mi from the property.

PropertyIncidentsOffenders

Unlock the full safety report before making a decision about this neighborhood.

Full report contains 37 offenders within 5 miles and 886 crime incidents in the last 12 months.

37 Registered Sex Offenders within 5 miles Near 14755 Masthead Landing Cir, Winter Garden, FL 34787

37 Registered Offenders Nearby
4 Rape
18 Child Involved
6 Assault
15 Other
Photo Name / Age / Tags Arrest / Conviction Address Distance Risk
Offender photo

WILLIARD, ROBERT KENT

53 years old

Violent

SEX OFFENSE, OTHER STATE (SEXUAL BATTERY)

2024-09-02T17:06:34

16740 STATE ROAD 50 CLERMONT, FL, 34711
4.4 Medium
Offender photo

BURGESS, JOSEPH

70 years old

Lewd or lascivious molestation victim 12-15 years old offender 18 or older; F.S. 800.04(5)(c)(2) (PRINCIPAL)

2024-09-02T17:06:34

300 E LAFAYETTE ST APT 1 WINTER GARDEN, FL, 34787
2.9 Medium
Offender photo

CHEEVER, RICHARD LANE

68 years old

Child Involved

LEWD,LASCIVIOUS CHILD U/16; F.S. 800.04 (PRINCIPAL)

2024-09-02T17:06:34

1055 N WEST CROWN POINT RD WINTER GARDEN, FL, 34787
4.7 Medium
Offender photo

CHIMNEY, ANTHONY JEROME

61 years old

Child Involved

Violent

SEX OFFENSE, OTHER STATE (ATTEMPT TO COMMIT SEXUAL ASSAULT OF A CHILD)

2024-09-02T17:06:34

14568 SIPLIN RD WINTER GARDEN, FL, 34787
1.2 Medium
Offender photo

COOKS, EDDIE JAMES

63 years old

Child Involved

107 COPELAND COVE CT WINTER GARDEN, FL, 34787
1.4 Medium

886 Crime & Incidents in the Last 12 Months

886 Crime & Incidents by Severity
88 Severe
44 Medium
46 Low
708 Other
Crime Location (Approx.) Severity Description

Medical Emergency

07/16/2026 10:10 PM

Maguire Rd, Ocoee, FL 34761

 Unknown

As discussed during the dispatch call, medical teams responded to a report of a conscious and breathing 73-year-old female near Maguire Road and West Colonial Drive who may need hospital transport.

Medical Emergency

07/16/2026 09:46 PM

Beldonshire Ln, Winter Garden, FL 34787

 Unknown

As discussed during the dispatch call, a medical emergency was reported near McKinley Square, close to the intersection of Beldonshire Lane and Promenade Alley. Fire and rescue units responded.

Medical Emergency

07/16/2026 09:45 PM

McKinnon Sq, Winter Garden, FL 34787

 Unknown

As discussed during the dispatch call, medical call for a 77-year-old female who fell and bumped her head and right shoulder near McKinnon Square. She is conscious and breathing but has difficulty breathing. Emergency units dispatched to the scene.

Medical Emergency

07/16/2026 09:07 PM

N Cross St, Oakland, FL 34760

 Unknown

As discussed during the dispatch call, medical responders dispatched for an 83-year-old woman who fell near Cross and Drive. She is conscious, breathing, and has a forearm injury. Patient contact confirmed.

Medical Emergency

07/16/2026 06:04 PM

North St, Winter Garden, FL 34787

 Unknown

As discussed during the dispatch call, emergency units responded to a medical call near North Denny's Drive, apartment number (number withheld), involving a 51-year-old female with a nosebleed.

Nearby Schools

Schools within 2 miles of this property, nearest first.

SchoolDistance
WHISPERING OAK ELEMENTARY0.7 mi
SUNRIDGE MIDDLE1.0 mi
SUNRIDGE ELEMENTARY1.0 mi

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Frequently asked questions

Is 14755 Masthead Landing Cir in a low-crime area?

The current report summarizes crime-related incidents within 5 miles during the last 12 months. HoodScore compares these records with relevant benchmarks, but no report can guarantee future safety.

Why are traffic and medical calls shown separately from crime?

Traffic, medical and fire records are public-safety incidents but are not necessarily crimes. HoodScore separates them to avoid overstating the crime count.

How often is this HoodScore report updated?

The report displays its generated date. Update frequency varies by source and is explained in the HoodScore methodology.

How is the HoodScore calculated?

HoodScore combines nearby crime and offender data into a neighborhood safety score. Visit https://www.hoodscore.com/hoodscore-calculator.html to see how the calculation works.