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(954) 789-3186 Helena.Grossberg@outlook.com
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(954) 789-3186
Helena.Grossberg@outlook.com
MLS# A4676382 - 5100 JESSIE HARBOR DRIVE OSPREY, FL 34229
This meticulously maintained, waterfront residence is nestled in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths, and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid appliances, custom cabinet pull-outs, and the kitchen’s showstopper is the exquisite stone counter surfaces, which wow and make everyday cooking—or your gourmet meal preparation—a joy. Plantation shutters and remote-controlled blinds grace many of the windows. The views from your master retreat Vye for your attention thanks to the shimmering intracoastal front and center. Generous in size, the master retreat delights with a walk-in shower, large soaking tub, double vanities, a separate makeup area, private water closet, and dual walk-in closets. The second bath features a recently installed walk-in tub, designed for enhanced comfort, ease, and safety. Enjoy expansive water views from your fourth-floor balcony, where nesting birds, jumping fish, and dazzling sunsets create a stunning backdrop for your daily pleasure. The inside laundry room and your two assigned parking spaces are located under the building and out of the elements, add to the opportunity. The lifestyle amenities in this friendly community include recently resurfaced tennis and pickleball courts, a heated swimming pool, a clubhouse with fitness area, kayak storage and launch, fishing. Boat slips are available on a first come basis for an additional fee. Enjoy a waterfront picnic under the gazebo, complete with grills, a walking path, and pretty greenspace areas. Ideally located close to shopping, dining, the crystal sand beaches, and the famed Oscar Scherer State Park—which offers biking, birdwatching, geocaching and over 15 miles of scenic hiking trails, and a natural lake for swimming—the best part is the proximity, located just across the street. Come be enchanted, as this slice of Florida paradise is one you won’t want to miss.

PREMIER SOTHEBY'S INTERNATIONAL REALTY is the brokerage office representing the owner for this listing.
© Copyright 2026, My Florida Regional MLS DBA Stellar MLS. all rights reserved.
The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional MLS DBA Stellar MLS distributed by MLS GRID. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.
ALM Realty & Services, Inc. is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of ALM Realty & Services, Inc., a broker participant of the My Florida Regional MLS DBA Stellar MLS. Stellar MLS data last updated at 12/31/2025 11:57:00 PM.

This meticulously maintained, waterfront residence is nestled in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths, and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid appliances, custom cabinet pull-outs, and the kitchen’s showstopper is the exquisite stone counter surfaces, which wow and make everyday cooking—or your gourmet meal preparation—a joy. Plantation shutters and remote-controlled blinds grace many of the windows. The views from your master retreat Vye for your attention thanks to the shimmering intracoastal front and center. Generous in size, the master retreat delights with a walk-in shower, large soaking tub, double vanities, a separate makeup area, private water closet, and dual walk-in closets. The second bath features a recently installed walk-in tub, designed for enhanced comfort, ease, and safety. Enjoy expansive water views from your fourth-floor balcony, where nesting birds, jumping fish, and dazzling sunsets create a stunning backdrop for your daily pleasure. The inside laundry room and your two assigned parking spaces are located under the building and out of the elements, add to the opportunity. The lifestyle amenities in this friendly community include recently resurfaced tennis and pickleball courts, a heated swimming pool, a clubhouse with fitness area, kayak storage and launch, fishing. Boat slips are available on a first come basis for an additional fee. Enjoy a waterfront picnic under the gazebo, complete with grills, a walking path, and pretty greenspace areas. Ideally located close to shopping, dining, the crystal sand beaches, and the famed Oscar Scherer State Park—which offers biking, birdwatching, geocaching and over 15 miles of scenic hiking trails, and a natural lake for swimming—the best part is the proximity, located just across the street. Come be enchanted, as this slice of Florida paradise is one you won’t want to miss.

PREMIER SOTHEBY'S INTERNATIONAL REALTY is the brokerage office representing the owner for this listing.
© Copyright 2026, My Florida Regional MLS DBA Stellar MLS. all rights reserved.
The data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of My Florida Regional MLS DBA Stellar MLS distributed by MLS GRID. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.
ALM Realty & Services, Inc. is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of ALM Realty & Services, Inc., a broker participant of the My Florida Regional MLS DBA Stellar MLS. Stellar MLS data last updated at 12/31/2025 11:57:00 PM.