Siesta Key FL Recently Sold Homes

CAN BE SOLD WITH MLS NUMBER: A4641964. A truly once-in-a-lifetime opportunity, this pristine Gulf-front parcel with naturally white sand along the breathtaking shores of Siesta Key’s exclusive northern tip. As one of the last remaining buildable Gulf-front lots on the island, this expansive property presents an unparalleled canvas to create a custom waterfront estate or an exceptional investment in luxury real estate. Positioned in one of Florida’s most coveted coastal enclaves, this direct beachfront lot provides a rare combination of privacy, prestige, and proximity. A short ride leads to the vibrant Siesta Beach and Village, yet the setting remains peacefully secluded, offering an idyllic retreat for those seeking both tranquility and convenience. Endless Possibilities on the Gulf! Creative Seller Financing Available! Consistently ranked among the world’s top beaches, Siesta Key is celebrated for its powdery sand, crystal-clear waters, and vibrant island culture. This exclusive Gulf-front property not only offers a rare chance to own a piece of this world-renowned paradise but also represents a sound long-term investment in one of Florida’s most sought-after luxury markets. Whether you seek to build a personal beachfront sanctuary or develop a estate that defines Gulf-front luxury, this extraordinary Siesta Key lot provides the perfect foundation for an unparalleled coastal lifestyle. Opportunities of this caliber are exceedingly rare—seize the chance to craft your dream on one of the most spectacular stretches of beachfront in the United States.

Solymar Drive, Sarasota

$599,000

2 Beds ⋅ 2 Baths ⋅ Boca Siesta SubDv. ⋅ 34242 Zip Code

PRICED TO SELL! Reduced Seller Motivated. Seize the opportunity to own a stunning slice of paradise located in the heart of Siesta Key, surrounded by flourishing trees and a tranquil boat basin. This well maintained fifth floor condo features two bedrooms/two bathrooms, offering breathtaking views of Little Sarasota Bay and the Intracoastal waterway. The kitchen and guest bedroom have partial Gulf views. Have your morning coffee on the screened lanai while observing the boats pass by. The condo features hurricane impact glass windows that provide strong protection against storms and high winds. The sliding hurricane shutters on the lanai is a practical solution making it easy to shield the outdoor area quickly when needed. The front entry door has also been recently updated. The guest bedroom's Murphy bed is a smart space-saving solution, allowing for versatile use of the room, complemented by built in book shelves. The custom bamboo closet systems enhance storage in every closet throughout the condo. The building is secure with keyless entry and video cameras. The marina was completely dredged in 2017 including the restoration of a new sea wall and boat slips. Enhancing the overall beauty and functionality of the marina, alongside the lovely landscaping with mature trees. Amenities are perfect for both relaxation and active living, with optional tennis court or pickleball play. The spacious clubhouse ideal for gatherings features a screened porch, fitness center and a full-size kitchen. Great for celebrations or meetings. The pools location by the Intracoastal Waterway adds a scenic touch, and having beach access across the street is a convenient perk. Enjoy a day on the Bay and launch your own kayak or paddle board from the community boat basin. Kayak & paddle board storage provided underneath the clubhouse. On site Maintenance Manager available Monday - Friday. Siesta Key is recognized as the #1 BEACH in the USA. Known for it's quartz sand and clear waters. Shop and dine at Siesta Key Village. The Breeze trolley is available on Midnight Pass Road and stops are designated where signs are posted in front of the complex. The Sunday drum circle at sundown at the public beach adds a unique cultural experience. The combination of comfort and relaxation makes this property an excellent choice for those who want to fully embrace coastal living. Siesta Key offers a blend of leisure and community that is truly special.

5911 Midnight Pass Road Unit 504, Sarasota

$375,000

1 Beds ⋅ 1 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code

Price Reduction! Beautifully renovated and turn key furnished with incredible views. Live the island life. Ready for immediate occupancy. The Pointe is surrounded by water on three sides allowing for stunning views of the bay and the gulf. Midnight Pass connecting the Gulf to the Bay, just south of The Pointe, has reopened as the result of the recent storms. This is great for estuaries, marine life, boating, and real estate values! The perfect place to watch a sunrise or a sunset and soak in the beauty of Neville Preserve and Little Sarasota Bay! This beautiful turn-key furnished 5th floor 1 bedroom, 1 bath unit has been fully remodeled, creating the ultimate retreat. The stunning kitchen features quartz countertops, beautiful cabinetry, stainless steel appliances, a breakfast bar and views of the ocean. The open floor plan creates a light and bright space that flows through to the large lanai with floor to ceiling sliders that stretch the back of the unit. The master suite was beautifully updated with a large walk-in closet, quartz countertops, dual sink, plenty of cabinets and storage, and a walk-in shower. The unit includes a washer/dryer in a closeted utility room off the lanai and a ground level storage unit which provides coveted space for beach and golf gear. An assigned covered parking space is conveniently located. A gated community, The Pointe is beautifully landscaped and features every amenity: a heated pool and spa, lighted tennis and pickle ball courts, private boat docks, kayak and paddleboard racks and launch, exercise rooms, men's and women's saunas, club house, a private island with gazebo and grills, and on site management and maintenance. This five plus acre property is conveniently located just a few minutes walk from Turtle Beach and three restaurants. Come live at the less traveled, more tranquil end of the Key and enjoy the walking and bike paths under tree-lined Midnight Pass Road. Boat docks are available!!

9393 Midnight Pass Road Unit 503, Sarasota

$650,000

2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code

Paradise awaits at Gulf & Bay Club Bayside on Siesta Key. FIRST-FLOOR, TURNKEY FURNISHED, 2-bedroom, 2-bathroom residence includes a deep one-car GARAGE. Flexibility of weekly rentals, perfect for personal enjoyment or as a lucrative income-producing property. Located in a popular gated community just steps from DEEDED BEACH ACCESS to world-famous Siesta Key and Crescent Beach. This home invites you to live like you’re on vacation. Tile flooring throughout allows for easy cleanup. Well-equipped kitchen with stainless steel appliances, pantry closet, breakfast bar seating and a dedicated dining area. The open-concept living room flows seamlessly to a covered and screened lanai overlooking a tranquil pond and tennis courts. Both bedrooms are generously sized, and the convenience of an in-unit washer and dryer (only 1 year old) adds to the home’s appeal. With no hurricane damage to the unit, peace of mind comes included. The community offers a true resort lifestyle with two heated pools, clubhouse with a full kitchen and fitness room, tennis and pickleball courts, BBQ grills, a newly renovated fishing dock, boat loading zones, and scenic walking paths. A dedicated on-site property manager makes rentals effortless. The location is unbeatable – just steps to the beach and a quick ride on the free Siesta Key trolley to explore the vibrant Village or South Siesta’s dining and shopping. Whether you're seeking a full-time residence, vacation home, or investment property, this is your chance to enjoy the best of island living on Siesta Key.

1226 Siesta Bayside Drive Unit 1226C, Sarasota

$1,090,000

2 Beds ⋅ 2 Baths ⋅ Siesta Towers SubDv. ⋅ 34242 Zip Code

Welcome to Siesta Towers on Siesta Key, where breathtaking Gulf views meet luxurious modern living. Positioned high above on the 9th floor, this stunning 2-bedroom, 2-bath residence showcases sweeping vistas of the Gulf waters, Big Sarasota Pass, and Downtown Sarasota from its expansive private lanai. Completely remodeled with no expense speared, from the studs out in 2024. This 1,440 sq. ft. condo is brand new in every sense of the way. Updates include all new drywall, texture and paint, new plumbing, new electrical, new electrical panel, new hurricane-rated impact windows and sliding glass doors, new air conditioner, and a new hot water heater. Inside new high-end interior finishes, with no expense spared. The chef's inspired kitchen is equipped with custom cabinetry with soft close doors and drawers, beautiful quartz countertops, large island, undermount single bowl kitchen sink, designer tile backsplash, top-of-the-line GE stainless steel appliances, built-in island microwave, and a wine/beverage refrigerator. All new interior doors, closet doors, all new interior millwork to include crown molding, all new lighting and fixtures, new luxury vinyl flooring throughout. Beautifully re-designed bathrooms to include high-end porcelain tile, custom cabinetry with soft close doors and drawers, lighted mirrors, and glass enclosure showers, create a sophisticated yet inviting coastal ambiance. Also, a new in-unit full size washer & dryer with folding table, for ultimate convenience. This beautiful residence comes completely turnkey-furnished with designer-quality furnishings and carefully curated décor, kitchenware, bedding, bathroom linens, and even high-end "Art Frame" TVs making it move-in ready for you to enjoy the Siesta Key lifestyle immediately. Siesta Towers itself has been thoughtfully updated throughout the building and grounds, offering resort-style amenities, including a state-of-the-art club room, fitness center, heated waterfront swimming pool, fishing pier, and a social pier perfect for sunset cocktails. Additional conveniences include storage room for beach equipment, bike storage and a very secure building environment. Whether you're seeking a full-time residence or a perfect beachside retreat, this pristine condo delivers the best of island living. Modern luxury, panoramic views, and resort-style amenities, all just minutes from the world-famous white sands of Siesta Beach. And with Siesta Key Village dining, shopping, and entertainment just a short walk away, this condo truly offers it all.

4822 Ocean Boulevard Unit 9D, Sarasota

$550,000

2 Beds ⋅ 2 Baths ⋅ Twin Oak Pond SubDv. ⋅ 34242 Zip Code

Opportunity knocking loudly! Here it is the least expensive pool home on Siesta Key. You will approach under a charming, canopy lined street. This 2BR/2BA is ready for someone to put their finishing touches on it after hurricane damage. Walls have been removed from 4 ft down, kitchen cabinets and counter removed. Nice Crown molding. Electrical was rewired and raised. Replumbed in 2020. Tankless water heater is 1 year old. A/C was new in 2023. Ductwork was replaced. Great Lap pool has new pool pump. Roof was patched and not leaking. This fabulous quiet location is a half a mile to the #1 Siesta Key Beach, this is your new place in the sun. Island living at its best.

5222 Winding Way, Sarasota

$975,000

3 Beds ⋅ 3 Baths ⋅ Harbour Towne SubDv. ⋅ 34242 Zip Code

RARELY AVAILABLE THREE BEDROOM THREE BATH WITH 10,000 POUND BOAT LIFT AND SLIP THAT ACCOMMODATES UP TO A 45’ BOAT! Have you heard? Big Pass Is Open! You can now access the open waters of the Gulf from Big Pass, located between south Siesta Key and Casey Key! Enjoy the intracoastal waterway North and South in protected waters. This condo has beautifully updated kitchen and baths, quartz countertops, newer appliances, beautiful flooring throughout and soaring 20’ ceilings. Relax in the glassed and screened lanai overlooking the deep-water boat basin. The second story offers additional living space, a private bedroom and bath and a spacious 12’ x 13’ storage room. Harbour Towne has a clubhouse, pool, spa, four pickleball courts and a tennis court. Enjoy the world-famous Siesta Key Beach right across the street. If you love beach life, boating, pickleball and tennis, this is the condo for you! You may especially like the Siesta Key Village vibe with an easy walk, cycle or free trolley ride to enjoy great restaurants, live music, and shopping. It’s all here for the resort get-away feeling!

1233 Dockside Place Unit 207, Sarasota

$632,500

2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code

Rarely available PENTHOUSE! Whether it's the shimmering city lights at night or a dazzling sunset that paints the sky with hues of orange and pink, this penthouse's vantage point provides a breathtaking backdrop for everyday living. Direct beach access, 2 bedroom/2 bathroom unit, fully furnished with everything you need. Just bring a suitcase. This bright unit features stainless steel appliances, porcelain tile flooring, crown molding, and elegant bathrooms. With plenty of storage, in-unit laundry, newer impact windows (2013), and A/C (2012), you can relish the Gulf breezes or stay cool during the summer heat. Peppertree Bay is an exceptional Beach to Bay complex that covers 16 acres, offering private deeded beach access, a fishing pier, two heated pools, two clubhouses, a fitness center, saunas, tennis/pickleball courts, and BBQ areas. Ideally located near Siesta Key Village, you'll have easy access to trolleys, frog hopper transportation, shopping, dining, and entertainment. Downtown Sarasota and its vibrant arts scene are just a short drive away. Contact us today to schedule a showing and discover the luxury of beachside living on Siesta Key.

1200 E Peppertree Lane Unit 607, Sarasota

$1,761,000

3 Beds ⋅ 2 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Welcome to your Siesta Key waterfront retreat—radiant with natural light and perfectly positioned on the Grand Canal. Elevated for peace of mind and crafted for coastal living, this three-story, 3-bedroom home with den/guest room celebrates time on the water from the moment you arrive. The main level opens to a large canal-view balcony and features a bright living room with a 22 ft ceiling, a defined dining area, and a chef’s oasis kitchen anchored by a center island—offering abundant storage, wood cabinetry, stainless-steel appliances, and expansive prep surfaces for effortless entertaining. Upstairs, the private primary suite spans the top floor with an adjacent office, a generous walk-in closet, and a spacious bathroom with dual sinks, soaking tub, and walk-in shower. Sliders open to your own third-floor balcony with beautiful canal views. The ground level offers a 2-car garage plus 700 sq ft of air-conditioned flex space (not included in main living area) with sliders to the pool and boat dock—ideal for a gym, rec lounge, or entertaining space. A private elevator connects all three levels—from the garage to the main living space and top-floor suite. Outside is a boater’s dream: deep-water frontage on the Grand Canal with quick access to Roberts Bay, Sarasota Bay, and the Gulf; composite decking, a 10,000-lb lift, and a seawall with turn-backs (all new as of Nov 2021). A clever two-level dock allows easy tide-height boarding and effortless kayak launches. This elevated Grand Canal home is perfect for boating, kayaking, paddle boarding, and daily dolphin/manatee watching. Lush, mature landscaping (on an irrigation well) wraps the property in privacy. All a short bike ride or walk to Siesta Key Village dining/shopping and world-famous Siesta Beach.

4929 Oxford Drive, Sarasota

$1,550,000

5 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Exceptional Investment Opportunity on Siesta Key – Turnkey 5-Bedroom Home with Strong Rental Income Potential Unlock the full potential of coastal luxury with this expansive 5-bedroom, 4-bathroom residence offering over 3,700 square feet of casually refined living space. Perfectly situated on an oversized, private lot just minutes from the world-famous Siesta Key Beach, this property is a rare find for savvy investors or those seeking a dual-purpose personal retreat and income-generating asset. Designed with both comfort and functionality in mind, the home features flexible living spaces, an abundance of natural light, a home office, and luxuriously updated kitchen and bathrooms. The kitchen is equipped with high-end stainless steel appliances, custom cabinetry, and ample prep space—ideal for entertaining guests or catering to vacationing families. Step outside to your own tropical oasis: a heated pool and spa, expansive patio, and lush, mature landscaping provide the perfect backdrop for relaxation and outdoor gatherings. The detached 3-car garage offers generous storage for vehicles, beach equipment, and water sports gear—an essential amenity for short-term rental guests. With a 7-night minimum rental policy, this property is perfectly positioned to generate premium vacation rental income year-round. The home's size, layout, and resort-style features make it an ideal choice for large families or groups, significantly increasing its desirability and earning potential in Siesta Key’s thriving short-term rental market.

185 Faubel Street, Sarasota

$4,700,000

4 Beds ⋅ 6 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. Welcome to a brand-new coastal masterpiece that redefines luxury living on world-renowned Siesta Key. Designed with both sophistication and comfort in mind, this waterfront retreat blends timeless architecture with modern amenities, all just moments from Siesta Village and the powdery sands of Siesta Beach. Inside, soaring ceilings and walls of glass bathe the home in natural light, while light wood floors bring warmth and elegance throughout. The heart of the home is a double-island chef’s kitchen, complete with premium appliances, custom cabinetry, and a generous walk-in pantry—perfect for both intimate family meals and grand entertaining. This residence offers four en suite bedrooms, including two primary suites (one upstairs and one downstairs), providing flexibility and privacy for family or guests. An additional private office and 600± SF of unfinished space above the garage present endless possibilities for customization. Seamlessly integrated indoor and outdoor living spaces create a true resort-style atmosphere. Step outside to enjoy multiple balconies, a pool and spa overlooking the water, a fully equipped outdoor kitchen, and a dedicated pool bath. For the boating enthusiast, this property features two boat lifts and quick access—just five minutes by water to the open bay. The location at the end of a quiet dead-end street ensures both serenity and privacy, with the added bonus of no homes directly across the canal, offering wide and peaceful views. This is more than a home; it’s a statement of waterfront luxury and the perfect canvas for your Siesta Key lifestyle. Days on market shows from pre construction. Certificate of occupancy issued September 2025.

4544 Woodside Road, Sarasota

$450,000

2 Beds ⋅ 2 Baths ⋅ White Sands Village SubDv. ⋅ 34242 Zip Code

Welcome to your own slice of paradise on stunning Siesta Key! This turnkey-furnished 2-bedroom, 2-bathroom condo is perfectly situated in the sought-after White Sands Village—just 367 steps from the world-renowned Siesta Key Beach, proudly ranked the #1 beach in the U.S. Whether you're seeking a full-time residence, a sun-soaked vacation getaway, or a high-performing income property, this condo has it all. Step inside to a bright, open living space that's been tastefully updated with stylish tile flooring, a fully equipped kitchen featuring sleek stainless-steel appliances, and modern bathrooms, and crown molding throughout. Both the living room and bedrooms are comfortably furnished and move-in ready—just bring your flip-flops! Unwind on your private screened lanai, where you can soak in the tropical breeze and peaceful sounds of nature. Recent updates include a new A/C Unit (2023) and Hot Water Heater (2019), adding peace of mind to your investment. Community perks include, Heated swimming pool & sauna, Boat docks (available for annual rental, first-come basis), Clubhouse for social events, BBQ grills & picnic spots, Multiple laundry facilities, Covered parking + plenty of guest parking. Directly across the street, Siesta Key Public Beach offers tennis, pickleball, volleyball, and a playground—perfect for active beach days. When the sun sets, hop on the free trolley or Frog Hopper and head to Siesta Village for live music, fantastic dining, shopping, festivals, and the weekend farmer's market. With a pet-friendly policy, flexible 2-week rental terms, and an on-site rental manager to handle everything, this condo offers not only a relaxing beach lifestyle but also excellent rental income potential. Don’t miss your chance to own a piece of paradise in one of the world’s most beloved beach destinations. Live the laid-back Siesta Key lifestyle—your coastal oasis is waiting!

5669 Midnight Pass Road Unit 308, Sarasota

$660,000

3 Beds ⋅ 4 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code

Buyer’s agent to verify all information, including all room, dock, property dimensions. Please use ShowingTime to schedule all showings. Property is highly distressed – proceed with caution during walkthroughs. Stay off the dock. Home is left unlocked with windows and doors open at all times. Exercise care when entering and walking through the property. Property is being sold "AS IS"

4725 Gleason Avenue, Sarasota

$735,000

2 Beds ⋅ 2 Baths ⋅ Siestas Bayside Waterside SubDv. ⋅ 34242 Zip Code

Looking for the perfect slice of Siesta Key paradise to make your own? This 2 bed/2 bath home is situated on just over ¼ acre lot with majestic trees offering shade, privacy and tons of character. The newly carpeted living room opens up to the Florida Room for the perfect marriage of indoor/outdoor living. An oversized screened patio just off the kitchen provides the perfect opportunity for alfresco dining. Both bedrooms are ensuite with fresh new carpeting while the primary has the added benefits of a walk-in closet, dual sinks with a vanity and maximum privacy due to the split floor plan. There is a dedicated laundry room with cabinetry and a desk if office space is needed. The circular driveway and 2 car garage provide plenty of parking. For families the highly rated Out-Of-Door Academy is just a few blocks away for Pre-K through Grade 5. The #1 Siesta Key Beach is located approximately 1 mile from the front doorstep. And the popular Siesta Village with a variety of dining and shopping options is even closer!

717 Treasure Boat Way, Sarasota

$900,000

3 Beds ⋅ 3 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code

Experience the ultimate in luxury living in this stunning 3-bedroom, 3-bath residence in the exclusive Dolphin Bay community on Siesta Key. With its expansive 2200 square feet of interior living space, multiple outdoor areas, and beautifully appointed features like plantation shutters and a gourmet kitchen, this property is the epitome of elegance. Enjoy breathtaking views of the Intracoastal from the expansive 45-foot wrap-around screened lanai, perfect for sipping morning coffee or evening cocktails. As a resident of Dolphin Bay, you'll have access to a range of exceptional amenities, including Har-Tru clay tennis courts, a heated pool and spa, fitness center, and private pier and dock. With its serene and private setting, abundant storage, and pet-friendly policy, this incredible property is the perfect haven for those seeking a luxurious island lifestyle. Take advantage of the Siesta Key Trolley to explore the vibrant Main Village, with its array of dining, shopping, and entertainment options. This residence also comes with a private 2 car garage which is hard to come by on Siesta Key.

1240 Dolphin Bay Way Unit 304, Siesta Key

$1,450,000

3 Beds ⋅ 3 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code

PRICE REDUCED $100,000 — FULLY FURNISHED* Whether you are looking for the IDEAL SECOND HOME that's furnished, has a pool and low maintenance grounds, or a PERFECTLY APPOINTED, remodeled with DESIGNER LIGHTING, 3 bedroom home, this fits the bill. Welcome to Roberts Point Road, one of the most desirable streets on Siesta Key—just steps to Shell Beach and minutes to the North Bridge for easy mainland access. This coastal residence blends island charm with smart, modern updates and is offered fully furnished for immediate, effortless enjoyment. Enter through a tranquil, private courtyard—perfect for quiet mornings or intimate evenings—into a dramatic, sunlit interior with soaring 22' ceilings and grand windows. The open-concept living area is anchored by a beautifully appointed, REMODELED KITCHEN with a center island, high-end fixtures, and dining space. Seamless indoor-outdoor living extends to a front courtyard patio with a HEATED POOL and a conveniently fenced, turfed backyard space that’s both low-maintenance but perfect for a dog run. The first-floor primary suite offers direct access to the courtyard balcony, dual walk-in closets, and a REMODELED dual vanity LUXURIOUS BATH. Enjoy two laundry rooms for ultimate convenience—one downstairs adjacent to the primary suite and a second laundry upstairs. The upper level provides two flexible bonus areas—ideal for a MEDIA LOFT and a DEDICATED OFFICE SPACE with built-in cabinetry. Signature updates include: NEW 2024 ROOF (big-ticket item complete), NEW POOL HEATER, NEW PAVER DRIVER and NEW PRIVACY LANDSCAPING—all enhancing comfort, curb appeal, and peace of mind. Bike to Siesta Key Beach, or head to Siesta Key Village, Southside Village, and downtown in minutes. CALL TODAY TO VIEW this the perfect, fully-furnished* island home—freshly updated, beautifully appointed, and ready now. (*staged items n/a).

4108 Roberts Point Road, Sarasota

$460,000

2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code

***PROJECTED GROSS REVENUE UPWARDS OF 45,000 PER YEAR***Experience the best of Siesta Key living in this light-filled, south-facing 2-bedroom, 2-bath condo at The Anchorage on Siesta Key. This spacious unit features a large, private balcony with tranquil views of the canal and Intracoastal Waterway, buffered by lush mangroves for added privacy. Enjoy balcony access directly from the main bedroom a perfect spot for morning coffee or evening sunsets. The second bedroom also features an ensuite bathroom, offering comfort and privacy for guests or family. Offered fully turnkey furnished just bring your suitcase and move right in! Stylish new furniture from 2024 complements the open layout, while recent updates include fresh interior paint and durable life-proof flooring in the primary bedroom. Additional upgrades such as a newer water heater installed in 2020. Originally remodeled in 2010, the condo seamlessly blends modern convenience with timeless coastal charm. Enjoy deeded private beach access to the world-renowned #1-rated Siesta Key Beach, just a short stroll across the street. The Anchorage is a highly desirable waterfront community offering resort-style amenities: a heated Olympic-size pool, fitness center, his-and-hers saunas, lighted tennis court, two pickleball courts, BBQ grills, shuffleboard, and beautifully maintained gardens along the water. Boating enthusiasts will appreciate the first-come, first-served boat slips with direct Intracoastal access, available to owners for just $10/month. Perfect for both personal use and investment, this property allows weekly rentals year-round (1-week minimum), offering excellent income potential. The on-site professional management team makes ownership and guest rentals effortless. Additional features include an elevator in the building, ample parking, and a secure, welcoming community environment. Ideally located near the Stickney Point Bridge for easy access to the mainland, and just minutes from shops, restaurants, Siesta Key Village, and downtown Sarasota’s vibrant arts and culture scene. Whether you're seeking a full-time residence, seasonal retreat, or high-performing rental property, this condo delivers the best of coastal living on Siesta Key.

6415 Midnight Pass Road Unit 205, Sarasota

$482,000

2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code

Now available at the lowest price per square foot with a full bay view on South Siesta Key! Behind the gates to the southernmost tip of Siesta Key lies The Pointe, a quiet community that, by it’s own words, supports and enriches it’s owners quality of life. This fourth-floor unit offers the largest footprint available with engaging amenities. Start your day with a gaze over glimmering waters as the sun rises or soak up warm Florida sunsets as day fades to dusk. A clean, bright space, this beautiful space will accept your most personal aesthetic. A large kitchen with white cabinets and stainless appliances is where you can craft your creative cuisine. Abundant windows provide views from every room while allowing cheerful Florida sunshine to fill the generous, open concept living and dining room. Your primary suite is spacious with en-suite bath and access to the adjacent screened lanai. A second bedroom will comfortably accommodate your family or guests with a second bath that will nicely suit their needs. The lanai serves as a perch to drink in the view while considering your upcoming day or relaxing and counting your blessings after sunny Siesta Key adventures. An oversized laundry room is beyond convenient, as well as the premier parking spot for this unit just steps from the front of the building. Situated on over 5 acres of premier and gated Siesta Key property, find yourself immersed in an elevated lifestyle featuring exceptional amenities including a heated lap pool & spa, clubhouse, tennis & pickleball courts, fitness center, BBQ grills, boat docks and kayak storage, as well as onsite management. Every Siesta Key day offers local adventures including Turtle Beach, Crescent Beach, the lively Siesta Key public beach & park, the vibrant Siesta Key village, along with a plethora of shops and eateries. Venture a bit further and experience the lively cultural scene of downtown Sarasota, any number of barrier islands and their beaches, historical Venice, or one of the many gorgeous golf courses in and around the area. The quintessential Florida lifestyle can be yours here at The Pointe!

9397 Midnight Pass Road Unit 404, Sarasota

$6,600,000

4 Beds ⋅ 5 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code

* Pending. Accepting backup offers.* Nestled along the pristine northern shores of Siesta Key, this magnificent three-story waterfront retreat redefines coastal luxury and exclusivity. The home features 10,600 sq ft under roof with approximately 5,500sq ft under air. This exceptional home is crafted for grand entertaining and effortless relaxation. While Siesta Beach and Village are just minutes away by golf cart, the gated personal estate ensures total privacy, creating a secluded paradise where the rhythm of the waves and the beauty of the Gulf serve as the ultimate backdrop. As you approach, a sprawling driveway and state-of-the-art security gates provide both exclusivity and convenience, granting access to a four-car garage, perfect for luxury vehicles, watercraft, or additional storage. Stepping inside, you’re greeted by a grand entrance with a 34-foot-high foyer. Up the stairs you will find walls of glass showcasing unobstructed Gulf panoramas. Expansive retractable glass doors erase the line between indoors and out, immersing you in the stunning coastal setting from the moment you arrive. Descending to the main living level, a chef’s dream kitchen awaits, masterfully designed with thick quartz countertops, a spacious center island, and a custom eight-seat breakfast bar. Flowing seamlessly into sun-drenched living and dining areas, this space is enhanced by towering 12-foot ceilings, creating an atmosphere of grandeur and warmth. A hidden bonus room unveils a fully equipped outdoor kitchen and entertainment lounge, offering a seamless transition to alfresco dining and unforgettable gatherings under the stars. The upper levels of the home are dedicated to rest and rejuvenation, with four private bedroom suites, each offering breathtaking Gulf views, intimate balconies, and spa-inspired en-suite baths. The primary suite, a haven of tranquility, boasts 270-degree water views, expansive lounging terraces, and a marble-clad spa bath, designed to capture the essence of relaxation and indulgence. Beyond the home’s elegant interiors lies a spectacular tropical oasis. Designed by the renowned Lucas Lagoons, the lagoon-style pool and spa feature a cascading waterfall, offering the ultimate retreat for relaxation. A meandering stone pathway winds through the gorgeous landscape, passing a serene saltwater tidal pond, leading to a two-story Tiki retreat, an idyllic setting for sunset cocktails and ocean breezes. At the edge of the property, a Gulf-front fire pit, nestled into the immaculate white sands, invites you to unwind as the sky transforms into a breathtaking masterpiece of colors. Whether envisioned as a luxurious primary residence or an exceptional coastal retreat, this one-of-a-kind Gulf-front estate offers an unparalleled blend of seclusion, sophistication, and effortless luxury. With unrivaled beach frontage and panoramic water views, this property is more than just a home—it is a rare opportunity to own a true piece of paradise on one of the most coveted stretches of Siesta Key. This listing does not include the lot at 0 Solymar Dr. MLS number (A4642147). Creative Seller Financing Available!

3935 N Shell Road, Sarasota

$490,000

2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. Welcome to Island Reef, an amenity rich Gulf to Bay resort where living the dream meets reality. Located on the tranquil southern end of Siesta Key you are just steps away from enjoying boating activities on the Intercoastal, a day at leisure on the beach or taking in a beautiful sunset over the Gulf. Come see this BAYSIDE condo that has undergone a remodel to include raising the ceiling in the kitchen and dining room areas, retexturizing all ceilings in the condo and installing plank tile flooring in the dining, living and both bedrooms. The kitchen features solid wood cabinetry to the ceiling, granite countertops, stainless steel appliances and an enlarged pass through to the dining area. The final piece of the remodel includes a customized office nook with a built-in desk with overhead and adjoining storage cabinets. Meticulously cared for this light and bright condo with white/off white colors throughout provides a neutral pallet for all your furniture and decorating ideas. The spacious Primary Suite features sliders to the screened and glass enclosed lanai, a large walk-in closet, bathroom with dual sinks and a walk-in shower. A generous-sized guest bedroom with shower and bath is ideal for family or guests. With its open floor plan the focal point of this condo is the spacious living/dining room which flows into the east facing tiled screened lanai; a perfect place to enjoy the dawn of a new day or a shady respite in the afternoon. For your peace of mind, the A/C unit was replaced in May 2024 and the hot water heater in 2020. At Island Reef the vacation never ends with your choice of two heated pools, a remodeled clubhouse, fitness room, newly resurfaced lighted tennis and pickleball courts, barbeque patios with gas grills, deeded beach access, boat docks, fishing, a place to store your bike or kayaks and so much more. In true island fashion you can walk to the front entrance of the complex, hop aboard the free classic style Breeze Trolley and enjoy a fun and relaxing day venturing out to a wide variety of restaurants, bars, gourmet grocery stores and shops on the Siesta Key while your car is parked in the shade of your deeded carport space. If you’re looking for a seasonal refuge from our Northern winters, a full time residence or an investment with attractive rental possibilities you can’t go wrong at Island Reef.

8773 Midnight Pass Road Unit 205G, Sarasota

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