Siesta Harbor Real Estate

Siesta Harbor Real Estate

Welcome to Siesta Harbor, a hidden gem nestled in the heart of Siesta Key, Florida. This charming waterfront subdivision offers an idyllic blend of coastal living and vibrant community spirit, making it the perfect destination for those seeking both relaxation and adventure.

Situated in Sarasota County, Siesta Harbor boasts an enviable location just minutes from the world-renowned Siesta Key Beach, known for its powdery white sand and crystal-clear waters. Residents enjoy easy access to a variety of water activities, from paddleboarding and kayaking to fishing and sailing. The serene canals that weave through the neighborhood provide a picturesque backdrop for leisurely strolls or bike rides, while also serving as a gateway to the Intracoastal Waterway.

Siesta Harbor is not just about stunning natural beauty; it’s also a thriving community. With a mix of single-family homes and condos, the subdivision caters to a diverse range of lifestyles, whether you're a full-time resident, a seasonal visitor, or an investor seeking rental opportunities. The friendly atmosphere is enhanced by community events and social gatherings, fostering connections among neighbors and creating a true sense of belonging.

In addition to its charming residences, Siesta Harbor is conveniently located near an array of dining, shopping, and entertainment options. From casual beachside eateries to upscale restaurants, you’ll find plenty of choices to satisfy your culinary cravings.

Experience the best of coastal living in Siesta Harbor, where every day feels like a vacation. Whether you’re watching the sunset over the water or exploring the vibrant local culture, life here is nothing short of extraordinary. Come and discover your slice of paradise!

Newest Listings in Siesta Harbor

1300 N Portofino Drive Unit 105, Sarasota
$399,900
1 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
YOU DESERVE PARADISE! MOVE RIGHT IN TO THIS PRISTINE DOLLHOUSE! BEACH ACCESS! BOATING! PERECT ONE BEDROOM WITH 2 FULL BATHS! GRANITE COUNTERTOPS, TOP OF THE LINE SHOWER ENCLOSURE, IMPACT/HURRICANE WINDOWS!! THIS HAS IT ALL!, WALK RIGHT OUT FROM YOUR LANAI TO YOUR BOAT DOCK, HEATING SWIMMING POOL, HOT TUB, SAUNA, SHUFFLEBOARD, DOCK ON THE INTRACOASTAL FOR MEETING WITH YOUR FRIENDS, FISHING OR JUST RELAXING! SIESTA HARBOR IS IN A PRIME LOCATION ON THE KEY, WALKING DISTANCE TO SHOPS, RESTAURANTS, CATCH THE TROLLEY RIGHT OUTSIDE YOUR DOOR, BEACH ACCESS RIGHT ACROSS THE STREET TO BEAUTIFUL SIESTA KEY BEACH WITH QUARTZ CRYSTAL SAND! THIS UNIT IS HOME OR A RENTAL, UP TO YOU! MOVE RIGHT IN, NEW HVAC, TILE FLOORS, CROWN MOLDING, PLANTATION SHUTTERS, FULL GLASS ENCLOSURE ON THE LANAI THAT BRINGS IN THE SUNSHINE, WATCH THE DOLPHINS, BOATING.. EVERYTHING UPGRADED WITH THOUGHT, NO POPCORN ON THE CEILINGS, ALL REDONE! ALL UNDER $400,000! YOU DESERVE PARADISE!

1300 N Portofino Drive Unit 105, Sarasota
1300 N Portofino Drive Unit 103, Sarasota
$449,500
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
Welcome to your own piece of paradise on world renowned Siesta Key! This beautifully updated and freshly painted 2 bedroom, 2 bathroom residence in the highly desirable Siesta Harbor 55+ community is clean, bright, inviting, and ready for its next owner. Just steps from the soft, powdery sands of Siesta Beach, this is the perfect opportunity to enjoy the laid back island lifestyle you've been dreaming about. From the moment you walk in, you'll appreciate the fresh coastal feel and thoughtful updates throughout. The residence features beautiful luxury vinyl flooring, a renovated kitchen, updated bathrooms, a brand-new vanity in the guest bath, and new and newer appliances. The open and comfortable floor plan is filled with natural light and designed for easy everyday living. Adding even more peace of mind, a brand new air conditioning system was installed in October 2026, so the next owner can enjoy the comfort of a brand-new system from day one. One of the true highlights is the spacious all season's lanai, where you can sit back, relax, and take in the fantastic waterfront views. Watch boats cruise along the shimmering saltwater canal as you enjoy your morning coffee or unwind with a glass of wine in the evening. The canal leads directly to the Intracoastal Waterway and Gulf of Mexico, creating a beautiful backdrop and a constant reminder that you are living on Siesta Key. Siesta Harbor is an active and welcoming 55+ community with an incredible selection of amenities and activities. Enjoy the heated pool and spa, fitness center, sauna, clubhouse, shuffleboard courts, private Intracoastal pier, and a wonderful social calendar filled with community events and activities. Fishing enthusiasts will love the private waterfront pier, while boaters have the opportunity to lease dock space on a first come, first served basis. Residents also enjoy deeded beach access through Crescent Arms, beautifully maintained tropical grounds, on site management, private storage, and same floor laundry. With the free trolley stop conveniently located just outside the community, Siesta Key Village, local shops, restaurants, and entertainment are all easily accessible. The South Bridge provides convenient access to mainland Sarasota, downtown, and the area's many cultural attractions. Whether you're looking for a full-time home, a seasonal escape, or your own island retreat, this residence offers an incredible combination of location, thoughtful updates, waterfront views, amenities, and lifestyle. With the brand-new air-conditioning system, freshly painted interior, updated kitchen and baths, and beautiful waterfront setting, so much has already been taken care of for you. Just move in, relax and enjoy everything Siesta Key has to offer. Come see why life is better on the Key!

1300 N Portofino Drive Unit 103, Sarasota
1300 N Portofino Drive Unit 305, Sarasota
$467,000
1 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
STUNNING TURNKEY ONE-BEDROOM, TWO-BATH CONDO AT SIESTA HARBOR! Welcome to your own slice of paradise on Siesta Key! This spacious, turnkey one-bedroom, two-full-bath condo features a bright, open floor plan and a fabulous private lanai overlooking the canal, with beautiful views toward the Intracoastal Waterway. Enjoy resort-style amenities including a heated pool, outdoor spa, poolside shower, shuffleboard, barbecue area, and clubhouse. The clubhouse offers a full kitchen, fitness room, sauna, and library. Boat slips are also available for rent through the Harbor Master. Located directly on the main Intracoastal Waterway, the complex and fishing pier provide the perfect setting for relaxing evenings, entertaining, and watching dolphins and manatees pass by. Best of all, beach access is directly across the street through Crescent Arms, making it easy to enjoy the world-famous Siesta Key beaches. The trolley and SCAT bus stop right outside the complex, while restaurants, shops, and other conveniences are just a short walk away. With easy access on and off the Key, this is the perfect beach retreat, vacation home, or investment opportunity. Come experience the Siesta Key lifestyle—you deserve paradise!

1300 N Portofino Drive Unit 305, Sarasota
1250 N Portofino Drive Unit 202, Sarasota
$469,900
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
This second floor 2-bedroom, 2 bath condo is located in the Marlin House in the 55+ community of wonderful Siesta Harbor! This unit offers an open floor plan with plenty of light. Step out onto one of the balcony’s to view the peaceful water, boats going by and you may see dolphins playing while you are enjoying your morning beverage. This community offers more than just serene water views. Included in the many amenities are a heated pool, shuffleboard, library and a fitness area. Feel free to participate in movie night, Tai Chi and Happy Hour along with many other activities offered at the clubhouse. Are you a boater? Siesta Harbor is one of the few condos on Siesta Key that offers a boat dock with deep water, for those interested in this bonus extra. If you wish to walk to the beautiful Siesta Key beach, voted best beach in the USA and the world, private access right across the street through a deeded access. Siesta Harbor keeps its grounds and buildings well maintained, recently updated with new roofs and updated common areas. This unit is a must have, with the deep water of the Intracoastal Waterway right in your backyard, the peaceful and serene atmosphere of the area, the beautiful beach just a shore walk away and it can be an income producer should that be something you want to consider.

1250 N Portofino Drive Unit 202, Sarasota
1257 S Portofino Drive Unit 104, Sarasota
$429,900
1 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
Bring your boat and dock steps from your back door.. Turnkey living in Siesta Harbor, a 55+ waterfront community, with beautiful canal water views and private beach access. This fully renovated 1-bedroom, 2-bath condo offers an open floor plan, updated kitchen and bathrooms, newer impact sliding doors, and a newer HVAC system (2021). Enjoy peaceful water views from the enclosed lanai as boats pass by. Boat slips are available for vessels up to 30’, with dockage approximately $1,000 annually (buyer to verify with Harbor Master). This property is also investment-friendly, allowing monthly rentals, and has a strong rental history (buyer to verify current rental restrictions and income). Community amenities include a heated waterfront pool, fishing pier, fitness center, clubhouse, shuffleboard, and busy social calendar. Additional features include assigned covered parking and private storage. Located just steps to beach access through Crescent Arms and close to dining, shopping, and the Siesta Key trolley. Ideal as a full-time residence, seasonal retreat, or income-producing property.

1257 S Portofino Drive Unit 104, Sarasota
1215 S Portofino Drive Unit 406, Sarasota
$410,000
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
AMAZING NEW PRICE! Escape the winter chill and claim your endless summer in the lowest-priced 2-bedroom, 2-bathroom condo in Siesta Harbor — a meticulously maintained, fully turn-key furnished gem perfect for anyone ready to embrace the relaxed Siesta Key lifestyle. This charming 4th-floor residence offers a peaceful harbor view with direct canal frontage, ideal for morning coffee on the balcony with a gentle waterfront breeze or quiet sunset dinners. Enjoy the convenience of a very inexpensive boat slip right here in the community — a rare and affordable perk for those who love leisurely days on the water. Step into a home that’s truly move-in ready. Lovingly cared for by the current owners, this turn-key furnished condo means you can leave the hassle of packing and decorating behind. Simply arrive with your suitcase and start living the Florida dream. Low HOA fees, worry-free maintenance, and the peace of mind that makes this an easy, low-stress choice. Siesta Harbor is an active 55+ community designed for the lifestyle you deserve. Enjoy deeded beach access via Crescent Arms, a fishing pier on the Intracoastal, a heated community pool, onsite management, and a full calendar of social activities with friendly neighbors. You’re just minutes from downtown Sarasota’s excellent restaurants, shops, medical facilities, and cultural attractions — everything you need is close at hand.This is more than a condo. It’s your opportunity to own an affordable slice of the laid-back tropical paradise on Siesta Key. Don’t miss this chance to lock in the lowest-priced 2/2 in the community at an amazing new price. Your endless summer is waiting.

1215 S Portofino Drive Unit 406, Sarasota
1300 N Portofino Drive Unit 406, Sarasota
$487,500
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
GORGEOUS NEW KITCHEN NEVER BEEN USED & OWNER WILL GIVE A CREDIT FOR ALL NEW WINDOWS!WATER VIEWS FROM EVERY ROOM! WATERFRONT HEATED POOL, HOT TUB, SHUFFLEBOARD,GATHERING AREA,BOAT SLIP,BEACH ACCES- LIVE IN PARADISE EVERYDAY IN this STUNNING RENOVATED CANAL-FRONT condo designer 2 bedroom, 2 bathroom condo nestled within the coveted Siesta Harbor community, offering private beach access to world-famous Siesta Key Beach just across the street. Situated on the fourth floor with picturesque water views, this beautifully updated unit features gorgeous quartz countertops, gray shaker cabinetry, stainless steel appliances, and brand new ceramic tile flooring throughout. Enjoy peace of mind with the glass-enclosed lanai with sliding glass windows that provides a serene retreat year-round. The open-concept layout flows seamlessly from the modernized kitchen into a bright and welcoming living space, perfect for entertaining or relaxing. Both bathrooms have been tastefully renovated, including a fully remodeled primary and guest bath, and the entire unit was freshly painted. Additional features include a private storage closet, updated lighting, and high-speed fiber optic internet. Siesta Harbor is a vibrant 55+ waterfront community along the Intracoastal Waterway, offering a heated pool, spa, clubhouse, fitness center, shuffleboard, fishing dock, sauna, BBQ area, and boat slips for up to 30’ vessels. Whether enjoying your morning walk to the beach, walking to lunch just minutes away, catching the free trolley to Siesta Key Village, or heading over the nearby bridge to explore downtown Sarasota’s dining, shopping, and cultural scene, this location offers the ultimate in coastal convenience and lifestyle. With monthly rentals allowed 12 times a year, it’s ideal as a personal escape or investment property.

1300 N Portofino Drive Unit 406, Sarasota
1257 S Portofino Drive Unit 307, Sarasota
$419,900
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
WATERFRONT RENOVATED 2 bedroom 2 bath condo is Siesta Harbor! WATERFRONT HEATED POOL, HOT TUB, SHUFFLEBOARD,, GATHERING AREA...So many upgrades, granite counters, stainless appliances, ceramic tile, impact sliders, turnkey Furnished! Water views from the living room, main bedroom and lanai, screened in lanai, great active clubhouse, heated pool, outdoor spa, out door shower, shuffleboard, barbecue area and outdoor shower. Private Beach access directly across the street. Siesta Harbor is located on the deepest point of the main intracoastal. Deep canal, boat slip up to 30' boat (check for availability, reasonable annual pricing.) Stunning Dock for fishing or relaxing ..... walk to all, restaurants, shops, easy on and off the key, the Trolley and scat right outside your door! One of the best parts being on the intracoastal with Beach Access! This has it all, just bring your toothbrush and be in paradise! Or rent it out, its a 30 day rental 12 times a year!!

1257 S Portofino Drive Unit 307, Sarasota
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