• Primary Photo - 5100 Jessie Harbor Dr
  • Building Photo - 5100 Jessie Harbor Dr
    Building Photo - 5100 Jessie Harbor Dr
  • Building Photo - 5100 Jessie Harbor Dr
    Building Photo - 5100 Jessie Harbor Dr
$1,995 / Month

5100 Jessie Harbor Dr Unit 302

,

Osprey, FL 34229

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5100 Jessie Harbor Dr Unit 302
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Beds Baths Average SF
2 Bedrooms 2 Bedrooms 2 Br 2 Baths 2 Baths 2 Ba 2,143 SF

Fees and Policies

The fees listed below are community-provided and may exclude utilities or add-ons. All payments are made directly to the property and are non-refundable unless otherwise specified.

  • Dogs Allowed
  • Fees not specified
  • Restrictions:
    small
  • Cats Allowed
  • Fees not specified
  • Restrictions:
    small

About This Property

BEAUTIFUL CONDO WITH LANAI ON THE INTER COASTAL WATER. 2 GARAGE SPOTS AVAILABLE. SMALL BOAT SLIP AVAILABLE FOR RENT ($.75 PER FOOT, PER MONTH) OPEN FLOOR PLAN, GREAT ROOM, PLUS A FORMAL DINNING ROOM AND A DEN IN ADDITION TO 2 BEDROOMS AND 2 BATHS. STORAGE UNIT AVAILABLE AS WELL AS KAYAK SLIPS.

5100 Jessie Harbor Dr is a condo located in Sarasota County and the 34229 ZIP Code. This area is served by the Sarasota attendance zone.

Condo Features

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Location
5100 Jessie Harbor Dr, Osprey,
FL 34229
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Edit Commute

Under 30 minutes

Commute Time is calculated at rush hour.
Neighborhood

The peaceful waterfront community of Venice and Englewood sits on Florida’s west coast overlooking the Gulf of Mexico. Originally established to provide lemon groves, the town retains a natural Old Florida feel with few buildings reaching higher than three or four stories. Fort Myers and Sarasota lie within commuting distance, and Sarasota Bradenton International Airport lies just 30 miles away.

Dotted with charming 50s-style beach homes and vibrant apartment rentals, the area is quintessentially Florida. Back on the mainland, you'll find plenty of golf courses and several parks where residents and visitors can enjoy outdoor activities such as fishing, cycling, and kayaking. With its stunning, unspoiled beaches and a pleasant year-round climate, you’ll feel as though you’re on a permanent vacation when you live in an Englewood/Venice apartment.

Learn more about living in Venice/Englewood 

Below are rent ranges for similar nearby apartments

Beds Average Size Lowest Typical Premium
Studio Studio Studio 570 Sq Ft $1,375 $1,644 $2,000
1 Bed 1 Bed 1 Bed 744-745 Sq Ft $775 $1,760 $4,750
2 Beds 2 Beds 2 Beds 1154 Sq Ft $1,300 $2,563 $18,000
3 Beds 3 Beds 3 Beds 1600-1601 Sq Ft $1,250 $3,309 $18,000
4 Beds 4 Beds 4 Beds 2478 Sq Ft $1,999 $5,402 $18,500
Amenities
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Education
Colleges & Universities Distance
Colleges & Universities Distance
SCF, Sarasota, Venice
Drive: 26 min 15.4 mi
Ringling Coll. of Art & Design
Drive: 28 min 15.8 mi
New College of Florida
Drive: 31 min 17.5 mi
SCF, Sarasota, Lakewood Ranch
Drive: 28 min 20.8 mi
5100 Jessie Harbor Dr Unit 302 is within 28 minutes or 15.8 miles from Ringling Coll. of Art & Design. It is also near SCF, Sarasota, Venice and New College of Florida.
Schools
Laurel Nokomis School
Public Elementary & Middle School
Grades PK-8
1,392 Students
Attendance Zone
Venice Senior High School
Public High School
Grades 9-12
2,727 Students
Attendance Zone
Auburn Road Presbyterian Academy
Private Elementary, Middle & High School
Grades K-12
Nearby
European Academy Of Early Education
Private Elementary School
Grades PK-5
64 Students
Nearby
Victory Baptist Academy
Private Elementary, Middle & High School
Grades K-12
68 Students
Nearby
School data provided by The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.

View GreatSchools Rating Methodology

Data provided by GreatSchools.org © 2026. All rights reserved.
Transportation

5100 Jessie Harbor Dr Unit 302 is near Sarasota/Bradenton International, located 18.4 miles or 33 minutes away, and Punta Gorda, located 40.4 miles or 51 minutes away.

Airports Distance
Airports Distance
Sarasota/Bradenton International
 Drive: 33 min 18.4 mi
Punta Gorda
 Drive: 51 min 40.4 mi

Walkability Near 5100 Jessie Harbor Dr Osprey, FL 34229

Getting Around
Somewhat Walkable
Walkability
30 / 100
Limited Public Transit
Transit
30 / 100
Exceptionally Drivable
Drivability
100 / 100
Fairly Bikeable
Bikeability
50 / 100

Scores provided by

What do Walkability, Transit, Drivability, and Bikeability mean? Walkability measures the walking distance to day-to-day needs. Transit measures access to public transportation. Drivability measures congestion, parking availability, and access to major roads. Bikeability measures the suitability for cycling. How It Works
-
Soundscore™
- / 100

Traffic

-

Airport

-

Businesses

-

Scores provided by

HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works
Points of Interest

Time and distance from 5100 Jessie Harbor Dr Unit 302.

Shopping Centers Distance
Shopping Centers Distance
The Shops at Casey Key
Drive: 3 min 1.2 mi
Osprey Plaza
Drive: 3 min 1.6 mi
Newton Plaza
Drive: 3 min 1.8 mi
5100 Jessie Harbor Dr Unit 302 has 3 shopping centers within 1.8 miles, which is about a 3-minute drive. The miles and minutes will be for the farthest away property.
Parks and Recreation Distance
Parks and Recreation Distance
Oscar Scherer State Park
 Drive: 3 min 1.2 mi
Laurel Park
 Drive: 5 min 3.0 mi
Pocono Trail Preserve
 Drive: 7 min 4.2 mi
Curry Creek Preserve
 Drive: 10 min 5.9 mi
Twin Lakes Park
 Drive: 16 min 11.4 mi
5100 Jessie Harbor Dr Unit 302 has 5 parks within 11.4 miles, including Oscar Scherer State Park, Laurel Park, and Pocono Trail Preserve.
Hospitals Distance
Hospitals Distance
Venice Regional Bayfront Health
Drive: 11 min 5.9 mi
Doctors Hospital of Sarasota
Drive: 17 min 13.2 mi
5100 Jessie Harbor Dr Unit 302 is 5.9 miles from Venice Regional Bayfront Health, and is convenient to other hospitals, including Doctors Hospital of Sarasota.
Military Bases Distance
Military Bases Distance
Governmental U.S. Coast Guard
Drive: 81 min 67.0 mi
MacDill Air Force Base
Drive: 97 min 75.7 mi
5100 Jessie Harbor Dr Unit 302 is 67.0 miles from Governmental U.S. Coast Guard, and is convenient to other military bases, including MacDill Air Force Base.

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