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$2,950,000
4 Beds ⋅ 5 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
New price! Experience the epitome of Siesta Key living in this exquisitely crafted residence near Siesta Village and renowned pristine beaches, with every conceivable amenity nearby. On a generous one-third-acre lot, this 2019 custom masterpiece by award-winning John Cannon Homes epitomizes luxury and sophistication. Boasting four spacious bedrooms, an office, and five baths, this home is an entertainer's dream, designed to host large gatherings with ease and elegance. Built with an unwavering commitment to quality and luxury, every detail has been thoughtfully considered to offer unparalleled comfort and convenience. Innovative technology is seamlessly integrated throughout the home, allowing for remote control from your smartphone, a cutting-edge media system for immersive sound and visual experiences, a Lutron lighting and blind system, and a reliable backup generator, ensuring uninterrupted enjoyment. The open-concept floor plan offers soaring ceilings illuminated by natural light. The great room flows seamlessly to the dining area and the fabulous chef’s kitchen, which features sleek custom cabinetry, an expansive island with seating, and quartz counters. Top-of-the-line Thermador appliances include a six-burner natural gas range and a built-in Miele coffee system, ensuring culinary excellence. The primary suite is a sanctuary of relaxation, welcoming its occupants after a day filled with sun and fun. Guests are pampered with their own en-suite baths and access to bespoke entertainment options, ensuring privacy and luxury for everyone. The heart of this magnificent property is the expansive outdoor lanai, featuring a stunning pool set against the backdrop of silver travertine tile, a rejuvenating spa, and a fully equipped kitchen and bar area, living room and fireplace, promising unforgettable moments under the sun or stars. As the sun sets, the outdoor living space becomes a central gathering spot, where music, laughter, and culinary delights blend to create the perfect evening. An automated irrigation system maintains lush greenery. A high-ceiling garage with a two-car lift provides ample space for your luxury vehicles, while a comprehensive camera system, impact doors, windows, and garage door, and a natural gas-powered generator ensure security and peace of mind. The high-quality construction offers an added benefit with reasonable insurance rates. This home promises a life of exquisite luxury and unmatched convenience, where the car keys are forgotten. Enjoy the convenience of being near the vibrant Village, as well as the white quartz sands and azure waters of Siesta Beach. Welcome to your paradise on Siesta Key, where every day there is a testament to the beauty of island living.

4940 Peaceable Way, Sarasota
$775,000
4 Beds ⋅ 3 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Exceptional redevelopment opportunity in Bay Isles on Siesta Key—where short-term rentals are permitted! The current home experienced water intrusion and damage during recent storms. This property is being sold for land value only. This generously sized parcel is two lots totaling 16,200 square feet (.37 acres), 90 ft of frontage and 181 feet deep. The lot spans the entire block from Anglin Dr to Flamingo Dr along Siesta Dr. No other residence backs up to it. This offering is an ideal canvas for a sizable custom home, pool, and pool-home. Whether you're a builder looking to create a luxury island residence or an investor eyeing short-term rental potential, this location delivers. In a quiet, established neighborhood, just a short distance from Siesta Key Beach and Siesta Village. Easy access to the mainland via the north bridge. A true strategic build site on Siesta Key.

3480 Anglin Drive, Sarasota
$1,300,000
3 Beds ⋅ 2 Baths ⋅ Waterside East SubDv. ⋅ 34242 Zip Code
INCREDIBLE VIEWS!.....INCREDIBLE ISLAND LOCATION!....INCREDIBLE INDOOR/OUTDOOR LIVING!....Turnkey Furnished & Located on a Quiet Cul-de-Sac street along the GRAND CANAL with Long Water Views ..... YOU will be "Wowed" by this 3 Bedroom/ 2 Bath Bright and Spacious Open Floor Plan that Seamlessly Flows to Over-Sized Screened Lanai with Heated Salt Water Pool--- Excellent for Entertaining as well as Everyday Activities****Updated Kitchen and Baths; Quartz Countertops & Luxury Vinyl Plank Flooring Throughout****Enjoy your Morning Coffee Poolside, Dinners Al Fresco and Sunset Cocktails Relaxing by the Waterside Fire-pit..... Ideal Property for the Boating Enthusiast with 10,000# Boat Lift & ease of Egress along the Grand Canal and just 5 minutes to the Intracoastal with Quick Access to the Gulf....and for the "Beach Lover"--- a quick bike ride to the Powdery White Sands of Top-Rated SIESTA KEY BEACH....Perfect as Investment, Vacation/Seasonal Property or Primary Residence!

572 Commonwealth Lane, Sarasota
$2,900,000
3 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Stunning Waterfront Home on Siesta Key with Spectacular Bayou and Bay Views. Welcome to this exceptional waterfront property located on the serene and sought-after Siesta Key. Situated on a quiet dead-end street, this gorgeous home offers breathtaking views of the bayou and open bay, along with direct access to protected sailboat waters, just 100 yards from the open bay. With a 16,000lb boat lift, you'll have the perfect setup for boating enthusiasts. This expansive residence boasts 3,400 square feet of luxurious living space upstairs and an additional 2,000 square feet of air-conditioned space downstairs (currently used as storage). Built with concrete block construction and impact windows, this home offers both durability and peace of mind. Step inside to discover a spacious, open-concept living area featuring beautiful real wood floors throughout. The gourmet kitchen is a chef's dream, equipped with an 8-burner gas range, double ovens, and top-of-the-line appliances. Perfect for entertaining, the kitchen flows into the living and dining areas, all of which offer panoramic water views. The oversized primary suite is a true retreat, offering ample space, stunning views, and a spa-like ensuite bathroom. A private den/office provides a quiet place for work or relaxation. The home also includes vaulted, beamed ceilings that add character and elevate the airy feel of the living spaces. Enjoy the Florida lifestyle with your own outdoor oasis, featuring a heated saltwater pool and spa, ideal for year-round enjoyment. The upstairs front balcony provides a perfect spot to unwind and take in the spectacular sunsets over the water. With an elevator for added convenience and tons of storage throughout, this home combines functionality with luxury. Located just minutes from Siesta Village and the world-famous Siesta Beach, you'll have access to vibrant local dining, shopping, and the best sandy shores on the Gulf Coast. Don’t miss the opportunity to own this incredible waterfront property on Siesta Key, where every detail has been thoughtfully designed for comfort, style, and waterfront living at its finest.

875 Siesta Key Circle, Sarasota
$3,200,000
4 Beds ⋅ 6 Baths ⋅ Miramar SubDv. ⋅ 34242 Zip Code
Major price reduction for immediate sale. Construction just completed on this new residence on the south end of Siesta Key. Located on Heron Lagoon offering breathtaking sunset views from various vantage points of the home’s major rooms. The best news: it’s totally FEMA compliant to the latest standards. High and dry from recent storms with NO water in the home and only a minor amount in garage. There is a sealant on perimeter from foundation to 1st level. The perfect solution for island lovers who want the protection of an elevated new home. The interior of this exceptional residence features an expansive and inviting atmosphere and its architectural charm is enhanced by trayed volume ceilings. The open and spacious Great Room and kitchen perfectly poised for entertaining. The kitchen is a culinary haven, featuring custom solid wood cabinets with painted shaker doors and quartz counters. State-of-the-art stainless steel appliances include a 6-burner gas range top with a griddle, a combination microwave/wall oven with dual fan convection, and a glass-door beverage refrigerator. The home boasts 7-1/2" wide European White Oak Hardwood plank flooring with a wire brush texture and polyurethane finish throughout,. The bathrooms showcase porcelain floor and wall tiles, custom solid wood cabinets, and either quartz or quartzite counters. The second floor of this residence features a splendid owner’s suite with a balcony, captivating water views, a luxurious master bath, a spacious loft, and three additional en-suite bedrooms. Pool-side is the expansive covered patio with pool bath, outdoor kitchen equipped with a natural gas grill creating the perfect setting for al fresco dining. Kick off your shoes and grab your paddle board or kayak and enjoy the afternoon on waters of Heron Lagoon from your private dock. Nestled in this peaceful locale, away from the hustle and bustle of daily life, the property remains conveniently close to the Stickney Point bridge, ensuring easy access on and off the island. Turtle Beach is a mere half-mile away, along with a marina for boaters. Easy to show.

8030 Midnight Pass Road, Sarasota
$650,000
3 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Home did have water intrusion and significant damage during the storms. The value is in the land as it Can Be Divided into 2 Parcels. Great opportunity to build 1 or 2 homes in quiet neighborhood near Siesta Key Beach. Short bike ride away to the beach. Located within one mile of Siesta Village! Easy access to the mainland via the North Siesta Bridge to enjoy Southside Village, Downtown, Marie Selby Gardens ad the Bayfront.

813 Plymouth Street, Sarasota
$1,625,000
4 Beds ⋅ 4 Baths ⋅ Sara Sands SubDv. ⋅ 34242 Zip Code
Tucked away at the end of a quiet cul-de-sac on Siesta Key, this well-kept four-bedroom, three-and-a-half-bathroom pool home offers an easygoing waterfront lifestyle with access to the Gulf of Mexico. Set on a corner canal lot with water on two sides and 286 feet of frontage, the property feels private and peaceful, surrounded by the calm beauty of the water. With 2,927 square feet of living space, the home has been carefully maintained by only two owners and has NEVER experienced flooding. Inside, wide windows frame the shimmering canal views, filling the living spaces with soft, natural light. The layout is open and welcoming, offering plenty of room to gather or spread out and enjoy quiet days at home. At the heart of the home, the kitchen connects easily to the dining and living areas and opens to the screened lanai and pool deck. Outside, an outdoor kitchen and a large 9-foot deep pool invites long afternoons in the sun, with water views in every direction. Just off the pool, a private spa room and bathroom offer a quiet retreat after a day on the boat or beach. The master bedroom is tucked away for privacy, featuring a spacious bathroom with double vanities, a step-up soaking tub, and two separate closets. The guest bedrooms are thoughtfully placed, offering comfort and easy access to well-appointed bathrooms. The home's setting along two sides of the water creates a feeling of openness. Whether you’re heading out for a day on the water, casting a line from your backyard, or simply watching the boats go by, this property brings the natural beauty of Siesta Key right to your doorstep. Just minutes from the world-renowned white sands of Siesta Beach and a short distance to the shops, cafes, and restaurants of Siesta Village, the location offers the perfect balance of island living and everyday convenience. Downtown Sarasota, with its farmers' markets, theaters, and waterfront dining, is just over the bridge when you feel like exploring beyond the island. This is a home for someone who wants the rare combination of space, privacy, and water access, all set in one of Florida’s most beloved coastal communities. Come see what life could be like at the water’s edge.

5181 Sandy Shore Avenue, Sarasota
$1,250,000
4 Beds ⋅ 4 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Here's the opportunity you have been waiting for. Incredible floor plan with this concrete block home. Large bedrooms with three on one side and the owner's suite on the other. Large in-home laundry, oversized garage and a corner lot. Wonderful private waterfront living with a pool, dock and easy access to Siesta Beach. The existing floor plan makes it easy to update and if you love terrazzo floors, they are under the carpet ready to come back alive. No water or hurricane damage sustained during last year's events, according to the owner. The owner’s suite and one of the guest suites have sliding doors to the pool lanai. Two bedrooms share a Jack and Jill bath. There's even a private outdoor shower. This is a solid home waiting for someone to update and begin creating memories. Schedule your showing today.

1014 Contento Street, Sarasota
$1,400,000
3 Beds ⋅ 2 Baths ⋅ Siesta Manor SubDv. ⋅ 34242 Zip Code
Location and excellence combined....Don't miss the opportunity to own this stunning 3 bedroom, 2 bath pool home with 75 ft. of canal access. The home is located steps from the vibrant village of Siesta Key and the #1 Beach in the USA and # 4 in the world! The property has been remediated and restored to the highest standards post hurricane Helene. The large private front courtyard welcomes you to the professionally decorated and designed tropical oasis to maximize the ultimate living experience. The large rear lanai overlooking the heated pool and spa provides a resort style atmosphere to both owners and guests. Quality finishes include travertine flooring throughout, impact windows and doors, completely renovated kitchen and baths and more. Easy access to downtown Sarasota to enjoy the arts district, theater, fine dining and shopping at St. Armands Circle. Continue the excellent rental opportunities or call it home, this property is a must see. Schedule your showing today.

309 Avenida Milano, Sarasota
$370,000
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
PRICED TO SELL SELL SELL! BEAUTIFUL VIEWS FROM MOST ROOMS OF THE CANAL AND INTRACOASTAL WATERWAY! END UNIT, 2 BED, 2 BATH, ARTICALLY DONE! IMPACT WINDOWS AND DOORS THROUGH OUT! TILE FLOORS! OPEN FLOOR PLAN PRICED TO SELL! SIESTA HARBOR OFFERS A FISHING DOCK ON THE WATERWAY, BEACH ACCESS RIGHT ACROSS THE STREET, WALK TO ALL SHOPS, RESTAURANTS ETC, EASY ON AND OFF THE KEY! THE SCAT AND TROLLEY RIGHT OUTSIDE YOUR DOOR! BEAUTIFUL HEATED POOL NAD OUTDOOR SPA-FITNESS ROOM= UPDATED CLUBHOUSE WITH FULL KITCHEN, BARBEQUE AREA, SHUFFLEBOARD AND SO MUCH MORE!

1350 N Portofino Drive Unit 310, Sarasota
$1,200,000
3 Beds ⋅ 3 Baths ⋅ Summer Cove On Siesta SubDv. ⋅ 34242 Zip Code
Imagine the perfect island getaway with gorgeous water views, just a short walk away from Siesta Beach. Positioned on the first floor of Summer Cove, this pristine three-bedroom condominium overlooks Sarasota’s sparkling Intracoastal waterway. The home’s unique setting includes not only a private elevator entry but a private staircase leading directly from your terrace to the scenic pool area and waterfront. Kick off your sandals in the spacious living room, with high, tray ceilings and sliding glass doors to the view, connecting you to the terrace and delightful sea breezes. The kitchen includes a breakfast bar, stainless steel appliances, granite countertops, and plenty of cabinets for storage. The primary bedroom boasts water views, access to the terrace, and features an en-suite bathroom with soaking tub, separate walk-in shower, and dual sinks. Host visitors with two additional bedrooms or use one as your personal yoga/music/art studio. A separate laundry room includes built-in cabinets and a sink. A refreshing swim in the Gulf or an evening in the clubhouse is just a quick stroll away. For architecture lovers, the Summerhouse clubhouse is an iconic addition to the Sarasota School of Architecture by esteemed architect Carl Abbott. You’ll also cherish the community amenities including heated pool, deluxe fitness center, kayak launch, and deeded beach access. The property comes with full time on-site management, two secured assigned parking spaces with storage in the parking garage. Take a trip to the mainland and downtown Sarasota – just a short drive away – for epicurean dining experiences and world-class arts and culture. Find out why Sarasota has been named the A Favorite Beach Town, the Cultural Capital of Florida, and No. 1 Place to Retire, time and time again.

1660 Summerhouse Lane Unit 102, Sarasota
$880,000
2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code
Reduced VILLA in Crystal Sands is the best Gulf-front community where the fine powdery quartz sands of Siesta Key are just steps away. Siesta Key is rated #1 beach in the USA! You found it! This turnkey furnished 2-full bedroom, 2-full bath villa is a great beach house. Enjoy the desirable split floor plan with 2 bathrooms and large closets. A separate attached garage allows for extra space if you want to convert it into a rec room. Enjoy sunsets and white sandy powdery beach views just steps away from your villa. The one car attached parking garage allows for direct access to your villa. Crystal Sands, an iconic resort on the Gulf of Mexico, is also pet-friendly with 2 heated pools, beach chairs & barbecue grills. Join the onsite rental office which offers rental services if you are looking to rent out this lovely villa when you are not enjoying it. Enjoy all the fun of restaurants and activities on Siesta Key and still be just 5 miles away from the heart of Sarasota’s downtown area.Expansive views with award- winning sunsets. As you take in the beautiful Gulf waters near your villa it is just as what you need. Convenient access to Siesta Village where plenty of shopping and dining choices await.

6300 Midnight Pass Road Unit 20, Sarasota
$700,000
Siesta Beach SubDv. ⋅ 34242 Zip Code
2 minute Stroll to Beautiful Siesta Key Beach! 2 Bed 1 Bath on each side. Seller pays quarterly for access to the inground pool just a few feet away as well. Nearby eating and shopping also walking distance. Lenny'z Pizza & Island Bar just a few feet away. No insurance claims or FEMA claims were made on the property. Just paid to mitigate for water damage and remove all damaged surfaces. Terrazzo floors and room for a courtyard area in the back. Indoor laundry hook up in between both units. Membership to Calini Beach club is optional but is what allows for the private beach access and the use of the pool.

1138 Sun N Sea Drive, Sarasota
$1,200,000
Sarasota By The Sea SubDv. ⋅ 34242 Zip Code
Welcome to your dream investment opportunity! This stunning duplex, ideally situated in a highly sought-after vacation destination, offers an exceptional chance to own a lucrative income-producing property. With modern amenities, stylish interiors, and a prime location, this property is perfect for vacation rentals, ensuring high occupancy rates and excellent returns. This exceptional property, featuring two newer A/C units (2022), a new water heater (2025), and a durable metal roof, promises both comfort and peace of mind. This turnkey duplex has been extensively renovated in 2025, featuring brand-new kitchens with modern cabinetry, countertops, and appliances, as well as updated electrical and plumbing systems for worry-free ownership. The metal roof has been professionally inspected and maintained, ensuring its durability and optimal condition for long-term reliability. Additional upgrades include stylish contemporary furnishings, making this property a fully equipped, move-in-ready investment opportunity. The one-bedroom, one-bath residence exudes charm with its contemporary kitchen and bath, tile floors, washer and dryer outside, and cozy living space, making it perfect for a single occupant or couple. The two-bedroom, two-and-a-half-bath townhome-style residence, spread over two levels, offers spacious living with wood floors upstairs, updated bathrooms, a modern kitchen, tile floors downstairs, and a laundry room for additional washer and dryer, ideal for families or larger groups. Outdoor living is a delight with low-maintenance landscaping, a generous patio area, and a private, gated backyard. The shared screened porch entry adds to the property's charm and functionality, while outside parking accommodates up to five cars. Residents could enjoy the heated pool and deeded beach access just one block away, offering the ultimate in convenience and leisure. Positioned within close proximity to shopping and restaurants, this property ensures that all your needs are met. With a proven rental history, this duplex is perfect for vacation rentals, promising excellent returns for the savvy investor. Experience the best of Siesta Key living at 6630 Midnight Pass Rd, where every detail has been curated for an exceptional coastal lifestyle. This duplex is a proven income producer with an established rental history and strong demand from vacationers year-round. The current owner has also used the property for family stays, suggesting that even higher income could be achieved with more dedicated rental availability. Don’t miss this rare opportunity to own a piece of paradise with outstanding income potential.

6630 Midnight Pass Road, Sarasota
$1,000,000
3 Beds ⋅ 2 Baths ⋅ Bay Isles SubDv. ⋅ 34242 Zip Code
Coastal Living Meets Elevated Views in Siesta Key Discover this unique waterfront retreat nestled on a saltwater canal in one of Siesta Key’s most sought-after neighborhoods. Featuring a 3-car garage and a main-floor primary suite, this home offers a flexible layout ideal for full-time living or a vacation getaway. The third floor boasts two additional bedrooms, a full bath, and a lofted overlook with views of the second floor’s open design. But the true showstopper? A rooftop observation deck with sweeping views of Big Pass and the Gulf of Mexico — the perfect sunset perch. Located on a street undergoing transformation with multiple new luxury builds, this property is a rare opportunity to enjoy now or reimagine later. At the end of the road, you’ll find a hidden beach enclave, offering a peaceful escape just steps from home. Whether you're drawn by the boating lifestyle, redevelopment potential, or panoramic rooftop vistas, this Siesta Key gem delivers coastal charm with untapped upside.

3737 Bayou Louise Lane, Sarasota
$1,259,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
** PRICE IMPROVEMENT! ** Welcome to this beautifully REMODELED 2 bed/2 bath GULF FRONT residence, where quiet luxury meets modern comfort! Breathtaking FULL GULF VIEWS. *FURNITURE INCLUDED.* Exceptionally light and bright, this is a rare, highly desirable END UNIT featuring an extra window with sunny southern exposure. Step inside to a spacious OPEN CONCEPT layout, featuring brand NEW 2025 LUXURY VINYL PLANK flooring, crown molding, beautifully textured walls and ceilings, and NEW 2025 designer overhead fandeliers and balcony ceiling fans. 5 panel interior doors throughout add an elegant touch. The living room offers deep elegant built-ins, perfect for displaying collectibles from your travels. Two NEW complete sets of 2024 floor to ceiling hurricane impact sliders open from the living room and primary bedroom into to your own 25’ private open air balcony overlooking 800’ of PRIVATE BEACH and the shimmering Gulf. After sunset, open the glass doors, pull the screen sliders across, and take in the gentle Gulf breeze as you drift off to the soothing sound of the waves. Wake up to breathtaking water views and the cheerful calls of the seagulls as you sip your morning coffee. The bright chef’s kitchen is designed for both functionality and style, with granite countertops extending into a built-in corner desk, a large breakfast bar, and premium KitchenAid, Bosch, and GE Profile stainless appliances. Thoughtful details include an Avallon 32-bottle wine refrigerator, warming drawer, soft close drawers, deep pull-out drawers for pots and pans, and an appliance garage, while dimmable recessed lighting adds ambiance to the space. The primary suite includes a custom walk-in closet and an ensuite bath featuring dual vanities and a glass enclosed travertine tiled shower. A set of French doors opens to the versatile guest bedroom, which is large enough to accommodate two queen beds or it can function as a home office or den. Ideally located just around the corner from Siesta Key Village, his extraordinary coastal retreat is waiting for you!

20 Whispering Sands Drive Unit 406, Sarasota
$535,000
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ph 1 & 2 SubDv. ⋅ 34242 Zip Code
This beautifully maintained first-floor 2-bedroom condo offers an exceptional opportunity to own a retreat on fabulous Siesta Key. Located in the highly desirable Midnight Cove II community, this condo is across from Crescent Beach and just steps away from world-renowned Siesta Key Beach. It boasts picturesque views of the Intracoastal Waterway from the screened lanai, creating a serene and inviting atmosphere. The property has fully funded reserves and has passed SIRS inspections, providing peace of mind for the new owner. Designed for both comfort and convenience, the condo features resort-style amenities, including a marina with dock space available for rent or purchase, a heated pool, fitness center, basketball court, pickleball and tennis courts, fishing piers, and on-site management. Midnight Cove II is pet-friendly and allows one-week rentals, offering excellent short-term rental income potential. For added convenience, the on-site office can manage rentals on your behalf. Enjoy direct deeded beach access and proximity to the vibrant South Village, with its fine dining, shopping, and entertainment options. This condo is a perfect choice for investors or anyone seeking a relaxing retreat in one of Florida’s most sought-after locations. Best of all, this home has remained untouched by hurricanes, with no water intrusion, giving you peace of mind in your coastal retreat. Everything in this residence is ready and waiting for your personal touch.

1700 Cove Ii Place Unit 311, Sarasota
$650,000
Ocean Beach SubDv. ⋅ 34242 Zip Code
No HOA! Neighboring property also for sale, so you could potentially double the lot size. Land is a short walk to beach and Siesta Village and Patriot's Pier. Has Newer pool and this lot is 10,651 SF. Appointment required if buyer wishes to enter the home.

4510 Banan Place, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
ONLY 2 BLOCKS TO SIESTA KEY BEACH WITH NO HOA!!! This location is the best. Come and see the possibilities of this home and it's location. This 2 bed 2 bathroom house, with a one car garage, and screened porch. Could be built back or have the opportunity to have a home of your own built.On this over sized lot that is in the heart of Siesta Key. Along with a Short walk or Bike ride into the village. Or just 20 minutes to Downtown Sarasota. Book a showing today. (Home took on water, but has had Remediation, but not built back)

5522 Calle Del Verano, Sarasota
$2,800,000
4 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Price improvement! Discover your coastal retreat in the heart of Siesta Key, where lush gardens create a relaxing oasis near the Gulf. This stunning four-bedroom, three-and-a-half-bath coastal contemporary home offers a blend of luxury and convenience, perfect for full-time living or as your ideal vacation residence. Just .2 miles from the pristine, powdery white sands of Siesta Beach and only a half mile from the charming shops and restaurants of Siesta Village, this home offers an unbeatable location. With everything you need nearby, you can park your car and unwind in paradise. The moment you step inside, you are greeted by a color palette inspired by the sea and nature, creating a bright and welcoming atmosphere. The open-concept floor plan features a great room with built-in cabinetry and fireplace, a dining area, and a chef’s kitchen and breakfast bar, which boasts custom cabinetry, quartz countertops and a suite of GE Café appliances, including a smart 5-in-1 oven, wall convection oven and a five-burner range with a pot filler. New pendant lighting and dining chandelier add to the inviting feel. The new, custom-designed bar room is the perfect place to gather and enjoy a cup of coffee in the morning with the new Miele coffee system, as well as watch sporting events with family and friends. Entertaining will be a pleasure with the two Uline wine refrigerators and freezer drawer. A private balcony overlooks the pool, with direct access to the expansive backyard via a curved staircase. A bedroom on the main floor doubles as a second primary suite, offering a luxurious en-suite bath, complete with stone countertops, custom cabinetry, glass subway tiles, and river stone floors—a convenient half bath rounds out the main level. Upstairs, the home offers even more space with a bonus room equipped with a mini kitchen and a west-facing balcony for those unforgettable, mango and fuchsia Siesta Key sunsets. The primary suite includes a private balcony overlooking the pool, while two additional guest bedrooms and a shared bath complete the upper level. Throughout the home, you'll find high-quality touches, including crown molding, transom windows, tray ceilings, and wide-plank wood and bamboo flooring. Go outside and discover the gem of this home, the professionally landscaped gardens. Tropical and lush, the private oasis offers ample space to sunbathe, swim in the large freeform saltwater pool, or relax under covered areas designed for entertaining, dining, and lounging. After a day at the beach, the outdoor shower will quickly become a favorite. In the evenings, gather around the fire pit to stargaze or unwind with family and friends. This home also boasts numerous upgraded amenities, including a new three-floor elevator from the garage, metal roof (2023), Lennox five-ton HVAC (2024), fresh exterior paint, wood balcony ceilings, garage doors (2022), newly renovated great room and bar room with custom built-ins, a whole-house gas generator, irrigation well and eco-friendly faux turf. With Hardie board siding, a paver driveway, and extensive landscape lighting, this home is both functional and beautiful. Ideally located on Siesta Key, close to Out-of-Door Academy and only 15 minutes from downtown Sarasota’s vibrant shopping, dining, and cultural attractions, this home is move-in ready. Don’t miss out on the opportunity to own a piece of paradise; your dream home awaits!

497 Island Circle, Sarasota
$370,000
2 Beds ⋅ 2 Baths ⋅ Inlet Apts SubDv. ⋅ 34242 Zip Code
Million Dollar Views at Half the Price.. Two Bedroom, Two Bathroom Corner End Unit... Discover the ultimate coastal retreat on the serene southern end of Siesta Key. This top-floor end-unit condo offers gorgeous partial Gulf views with coveted western exposure—perfect for soaking in breathtaking sunsets over the water. Just a short stroll to Turtle Beach and nestled along the picturesque Blind Pass saltwater canal, this hidden gem presents a rare opportunity to create your dream getaway. Though this unit is a fixer-upper, its unmatched location and incredible potential make it one of the best values on Siesta Key. Whether you’re seeking a personal sanctuary, a year-round residence, or a smart investment property, this condo offers the ideal foundation to bring your vision to life. Community Highlights: Boat-Friendly Living: Rentable boat slips available to owners and tenants on a 30-day rotation. Water Access: Dedicated kayak and paddleboard launch with secure storage. Peace of Mind: New seawall installed in 2022—proven resilient through the 2024 hurricane season. Resort-Style Pool: Recently resurfaced with new furniture, pump, and equipment. Outdoor Living: Brand-new community grill area, perfect for entertaining. Updated Exterior: Freshly painted in 2023 with a new roof added in 2024. Step into the laid-back charm of island living. Enjoy white-sand beaches and calm Gulf waters just minutes away. Explore local favorites in Siesta Village—home to vibrant restaurants, casual bars, and charming boutiques—all within walking or biking distance. Don’t miss this opportunity to own a slice of paradise. You can renovate the space to your taste, but this spectacular location is truly one-of-a-kind. Schedule your private showing today and start envisioning your future on Siesta Key!

9200 Midnight Pass Road Unit 30, Sarasota
$1,125,000
2 Beds ⋅ 2 Baths ⋅ Crescent Siesta Key SubDv. ⋅ 34242 Zip Code
FULL, exquisite Gulf views from this top floor, corner unit located directly on beautiful Siesta Key beach. Immerse yourself in luxury and relaxation while you soak up the sunsets from this turn-key furnished condo. You'll enjoy the well appointed living and dining room combo with large sliding glass doors that invite you to your private, screened lanai. The updated kitchen features granite countertops, new stainless steel dishwasher and microwave as well as all new dishes, drinkware, cooking ware and utensils. You'll appreciate the fact that the furniture, towels, linens, televisions and décor items are all new along with the newly installed water heater 2024. The spacious primary bedroom boasts a walk-in closet, while the guest room also features stunning water views. Crescent Arms is a gated community with an on-site manager, beautiful pool and clubhouse. This community is just steps away from shopping, fine dining, fishing charters, bike and jogging paths just to name a few, which means you won't run out of activities to enjoy. This unit is an active vacation property with a fantastic rental history and proven income. Very rarely does a unit become available here! Discover the Siesta Key lifestyle and find out why it is voted the #1 Beach in the USA. Experience paradise in your own backyard.

6312 Midnight Pass Rd Unit 702S, Sarasota
$1,135,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Surf & Racquet SubDv. ⋅ 34242 Zip Code
BEACHFRONT RESORT. Sarasota Surf and Racquet Club. Rarely available. This 2 bedroom, 2 bath gem in the highly desired Tower Building boasts an impressive rental history, with bookings through May 2025 offering excellent future income. Wonderfully updated and being sold turnkey furnished with travertine flooring throughout, granite counters in the kitchen and baths, all new stainless steel appliances in 2023, a split-bedroom plan, and convenient ground-floor access. A spacious storage room off the kitchen doubles as an owners' closet allowing you to come and go with ease between rentals. This exceptional resort community offers over 300 feet of sugar-white beachfront for you and your guests to enjoy. Staying true to the resort lifestyle, owners and guests may rent canopies, cabanas, tents and umbrellas for use on the beach. Other amenities at Sarasota Surf and Racquet Club include two heated swimming pools, multiple pickleball and tennis courts, a fitness center, and beachside and poolside barbecue grills. With stellar onsite owner and rental services and a three-night minimum rental policy, this property has it all!

5920 Midnight Pass Road Unit 104, Sarasota
$2,550,000
4 Beds ⋅ 3 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Welcome to 601 Avenida De Mayo, a stunning waterfront home nestled in the heart of Siesta Key. This exquisite property offers a rare opportunity to live in one the most coveted locations on the island, just a short walk from the the Village, powdery sands and crystal-clear waters that Siesta Key is renowned for. This exceptional property features a spacious double lot, offering ample outdoor space and a beautifully landscaped garden that enhances the home's curb appeal. Privacy is a paramount, with a private gate leading you into your own tropical oasis. The expansive grounds provide a perfect setting for relaxation or entertaining, with a sparkling pool and dock complete with a new 16,000 pound boat lift. Inside, the home boasts three levels of beautifully designed living spaces. The first floor features a spacious playroom and movie room, perfect for family gatherings and entertaining guests, with easy access to the screened lanai and pool area. The second floor is dedicated to comfort and privacy, with a luxurious master bedroom, a well-appointed en-suit bath, two master closets. Two additional bedrooms and one more bathroom complete this level, providing plenty of space for family and guests. The third floor is a true highlight, offering an open-concept kitchen, living room, and large bedroom, bathroom. The bright, airy space is perfect for both relaxation and entertaining, and the terrace provides an ideal setting to enjoy sunsets. For those who love to entertain or simply enjoy the beauty of Siesta Key, this waterfront retreat offers a unique compination of luxury, privacy, and unparalleled access to the Gulf and the vibrant life in Siesta Village. Don't miss your chance to own this incredible property-your piece of paradise on Siesta Key.

601 Avenida De Mayo, Sarasota
$725,000
Ocean Beach SubDv. ⋅ 34242 Zip Code
Take a Look!...This Unique Opportunity on Siesta Key JUST REDUCED...One of the Few Properties of Its Kind, Offering an Expansive 0.30-Acre Lot Overlooking a Serene Pond...Just a Short Stroll to the World-Famous White Sands of Siesta Key Beaches and the Vibrant Village, Full of Fine Dining, Boutique Shopping, and Entertainment...The Existing 4/3 Home Sustained Hurricane Damage, Making it an Ideal Prospect for a Custom Build or Inspired Renovation of the Locally Designed Classic...Unlike Most Tear-Downs, This Property Boasts a Coveted Natural Setting with Stunning Water Views and Breathtaking Sunsets Over the Water...Perfectly Positioned a Short Drive from Downtown Sarasota, St. Armands Circle, Longboat Key, Lakewood Ranch, and Sarasota-Bradenton International Airport...Surrounded by the Azure Coastal Waters of the Gulf...Floor Plan Concepts are Available for New Construction or Renovation...4710 Gleason Avenue is an Extraordinary Location with Endless Potential, and a Lifestyle That Elevates Your Living Experience...Opportunities Priced Right Like This Don’t Last on Siesta Key...Seize It Now and Live a Fuller Life!

4710 Gleason Avenue, Sarasota
$725,000
4 Beds ⋅ 3 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code
Take a Look!...This Unique Opportunity on Siesta Key JUST REDUCED...One of the Few Properties of Its Kind, Offering an Expansive 0.30-Acre Lot Overlooking a Serene Pond...Just a Short Stroll to the World-Famous White Sands of Siesta Key Beaches and the Vibrant Village, Full of Fine Dining, Boutique Shopping, and Entertainment...The Existing 4/3 Home Sustained Hurricane Damage, Making it an Ideal Prospect for a Custom Build or Inspired Renovation of the Locally Designed Classic...Unlike Most Tear-Downs, This Property Boasts a Coveted Natural Setting with Stunning Water Views and Breathtaking Sunsets Over the Water...Perfectly Positioned a Short Drive from Downtown Sarasota, St. Armands Circle, Longboat Key, Lakewood Ranch, and Sarasota-Bradenton International Airport...Surrounded by the Azure Coastal Waters of the Gulf...Floor Plan Concepts are Available for New Construction or Renovation...4710 Gleason Avenue is an Extraordinary Location with Endless Potential, and a Lifestyle That Elevates Your Living Experience...Opportunities Priced Right Like This Don’t Last on Siesta Key...Seize It Now and Live a Fuller Life!

4710 Gleason Avenue, Sarasota
$925,000
2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Experience the natural Florida coastal environment from this extraordinary viewpoint and the one-of-a-kind walkout to a private beach nestled in mangroves on the Intracoastal Waterway—perfect for launching a kayak or paddleboard. A dynamic scene unfolds daily with visiting shore birds of every description, dolphins feeding in pods, jumping mullet, and manatee lazily cruising by—just outside your backdoor. Tie up a boat to the private dock, do some fishing, and enjoy the sunset illuminating towering clouds rising in the eastern sky. This condo is proven to be Hurricane resilient. This unit, the garage, and the building came through 2024 unscathed as water flowed harmlessly down the north-side swale and along the driveway into the Intracoastal Waterway. Even the electrical power remained on during all recent storm events thanks to the hardened electrical supply installed along Midnight Pass Road by FPL in 2022. This two-bedroom, two-bathroom condominium features a stunning water view, a shaded front patio bordering a tropical garden, a third room which serves as an office/den, or possibly a 3rd bedroom with a simple addition of a Murphy bed. A one-car garage equipped with heavy-duty restaurant-grade shelving, bicycle racks, beach chair hangers, and kayak-paddleboard storage makes for ideal storage for an active lifestyle on the nearby water. Unit updates include impact-resistant PGT WinGuard sliding-glass doors and main bedroom windows, Trane four-ton two-stage HVAC system, refrigerator, water heater, cooktop, dishwasher, Hunter-Douglas Duet cellular shades, and garage door make this bright and cheery home ready for comfortable living. Join the friendly, close-knit Dolphin Bay community where the condo association just completed major projects for building painting, new exterior lighting fixtures, elevator refurbishment, new roofs, rooftop ventilation fan replacement, and clubhouse interior renovation. View cinematic video on Youtube: at https://youtu.be/VrWxlGmQ2lc

1280 Dolphin Bay Way Unit 202, Sarasota
$950,000
3 Beds ⋅ 3 Baths ⋅ Paradise Island SubDv. ⋅ 34242 Zip Code
This solid three-bedroom three bath pool/canal front home is located on a quiet cul-de-sac just behind Siesta Key village, and a mere 5-minute stroll to its eclectic shops, cafes, and fabulous restaurants, not to mention the world-renowned powder-white sands of Siesta Beach! Two of the bedrooms are en-suite. The living room, family room and one bedroom have access to the lanai and caged pool. Additionally, the family room features a working fireplace. There is a docking area with davits for your boat, with easy access to the intercoastal waterway and ultimately the Gulf of Mexico. In short, this is a perfect opportunity for a savvy investor or someone looking to settle down in one of Florida’s most beautiful and beloved coastal communities! The home had water intrusion from Hurricane Helene and was immediately and professionally remediated and sanitized. Renovations began but health issues forced a halt; Meet me at the property to review what changes can be made to the existing floor plan to maximize your income potential or to finish restoration to make this property your own! Typical rental income on a monthly rental in this neighborhood is $85 to 125k annually depending on whether you want to block out time for yourself. Don’t miss out on this incredible waterfront home priced near land value! Schedule your showing today!

322 Avenida De Paradisio, Sarasota
$455,000
2 Beds ⋅ 2 Baths ⋅ Turtle Bay SubDv. ⋅ 34242 Zip Code
Endless Potential in a Prime Location! Located in the highly desirable Turtle Bay on South Siesta Key, this two-bedroom, two-bath condo is a blank canvas- original and ready for its new owner to bring their vision to life. With stunning views of Little Sarasota Bay from the living room and private balcony, this unit offers the perfect foundation to create your dream coastal retreat. Enjoy access to an updated fishing pier-ideal for casting a line or simply soaking in the stunning water views. Boaters will love the private boat dock with boat slips available for just $300 a year, making it easy and affordable to explore the waterways. Additional community amenities ensure every day feels like a vacation along with a deeded beach access just across the street at Tortuga Community for direct access to the sparkling Gulf of Mexico waters world-famous sunsets. Inside, you'll find an open-concept layout, generous natural light, spacious bedrooms, and private balcony where you can take in the tranquil waterfront scenery overlooking the pool. The spacious layout provides an ideal backdrop for your renovation and personalization. Whether you're dreaming of a modern beach-chic aesthetic or a cozy Florida getaway, the possibilities are endless. Residents enjoy deeded beach access across the street, providing easy entry to the gulf and gorgeous sunsets! Additional highlights include a private detached garage, plenty of guest parking, and located minutes away from Siesta Key Village, shopping, dining and entertainment. Enjoy all the amenities at Turtle Bay which include a heated pool, tennis and pickleball courts, clubhouse, and fishing pier with day dockage. With the beach just a short walk away, this is your chance to own and transform a piece of paradise on Siesta Key.

8701 Midnight Pass Road Unit 206A, Sarasota
$1,300,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Enjoy true Florida living on Siesta Key on this high & dry lot in beautiful Siesta Isles. This one level home offers nearly 1900 sf of living space set on a 104' wide deep-water canal lot with access to Roberts Bay, the Intracoastal, and the Gulf of Mexico. NO STORM DAMAGE during the recent hurricanes! Move right in and update it to make it your own. Offering a Split Plan of 3 bedrooms, two full bathrooms, office, art studio, and a spacious enclosed Florida Room with loads of natural light. Enjoy watching the boats cruise by from the private Gazebo overlooking 104 ft. of canal waterfront. Plenty of outdoor space in the large, fenced yard with a sweet Mango tree - this shade tree produces fruit every year and is surrounded by a brick paver patio and walkways. The home has been re-plumbed during a prior remodel along with a new roof. Bring your boat or kayak and enjoy waterfront living in Sarasota. The community with 4 miles of salt water canal front waterways and a short bike ride to the #1 rated Siesta Key Public Beach. Room for POOL and BOAT LIFT.

5402 Shadow Lawn Drive, Sarasota