Find Rentals in Osprey

Houses For Rent

Apartments For Rent

Explore Listings

Property Managers

Listings Quality Policy

Renter Resources

Avoid Scams & Fraud

Rent vs. Buy Calculator

Rent Affordability Calculator

Help & Support

10 photos

Verified

Refrigerator

Dishwasher

- Save listing search
- Report this listing

5100 Jessie Harbor Dr

Osprey, FL 34229 - Sarasota County

Condo

2 beds

2 baths

2,143 sqft

About 5100 Jessie Harbor Dr

Enjoy luxury waterfront living in this beautifully updated 6th-floor condo at Blackburn Harbor Residences, overlooking the Blackburn bay. This 2-bedroom, 2-bath unit includes a den/flex room and offers panoramic water views from the main rooms. The fully remodeled kitchen features quartz countertops, stainless steel appliances and two refrigerators-perfect for entertaining. From the living room the glass sliders open to a private covered balcony that overlooks a gorgeous view of the Blackburn Bay. The Master Bedroom is spacious with private sliders that lead to the balcony and equipped with 2 walk-in closets. The Master Bathroom features dual vanity sinks, a private vanity and a spacious walk-in shower. The Guest bedroom is nicely situated to the Guest Bathroom that features a tub and shower combination. The flex room is ideal as a home office or can easily accommodate guests with a comfortable sofa sleeper. The community offers an impressive array of amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, shuffleboard, scenic walking trails, a kayak launch, boat dock, fishing pier and several outdoor grilling areas with a gazebo-perfect for embracing the Florida lifestyle. Ideally located just minutes from Nokomis Beach, Casey Key, Venice Beach and the world-famous Siesta Key. Residents also enjoy convenient access to Oscar Scherer State Park, historic Downtown Venice and lively Downtown Sarasota-offering premier shopping, dining and entertainment options. Provided by Compass Property Management - Your direction to Annual and Seasonal Living. Association: Application & Fee are Required. Utilites: None. Pets: No, sorry....

RentalSource last checked: July 17, 2025 at 4:32 PM ET

Last updated: July 10, 2025 at 4:30 PM ET

Listed by: Compass Property Management, (941) 444-6185

Property Summary

Property Type:	Condo
Rental Fee:	$3,950
Bedrooms:	2 beds
Bathrooms:	2 baths

Size:	2,143 sqft
Pet Friendly:	No
Listing Status:	Active
ID:	81773670

Property Amenities

• Balcony/Patio

• Dishwasher

• Microwave

• Refrigerator

• Waterfront Property

• Washer/Dryer In Unit

• Walk-in Closets

Community Features

• Boating

• Clubhouse

• Fitness Center

• Pool

• Tennis Court

Additional Details

Condo for rent in Osprey for $3,950 with 2 beds, 2 baths, 2,143 sqft and located at 5100 Jessie Harbor Dr in Osprey, FL 34229. The rental price of $3,950 is 149.8% ($2,369) higher than the average rent of $1,581 for a 2 bedroom condo in Osprey, FL and 94.2% ($1,916) higher than the average rent of $2,034 for a 2 bedroom condo in Sarasota County. 5100 Jessie Harbor Dr was advertised by Compass Property Management on July 10, 2025 at 9:11 AM ET and last checked yesterday at 4:32 PM ET.

Affordability Calculator

Can I afford to live at 5100 Jessie Harbor Dr?

Bedrooms

2 bedrooms

Rent-to-income ratio

30%

10% Recommended 50%

Move the slider to select the percentage of your monthly income you're comfortable spending on rent. Typically, it's advised to spend about 30% or less on housing.

Recommended income

$158,000 /year

With your chosen rent-to-income ratio, an annual income of $158,000 is recommended to comfortably afford this 2-bedroom rental priced at $3,950 per month.

For more information on rent affordability, visit our rent calculator or rent vs. buy calculator.

Condo for rent

$3,950

Rent Affordability Calculator

Interested in 5100 Jessie Harbor Dr?

Find out more about this property & see if it's available now.

Property managed by:

Compass Property Management
(941) 444-6185

Avoid rental scams - Situations involving wire transfers or a landlord who can't meet you in person can be red flags.