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$2,695,000
3 Beds 4 Baths Bay Island SubDv. 34242 Zip Code
548 Siesta Drive is more than just a home—it’s a gateway to the best of Siesta Key living with unmatched flexibility, location, and waterfront luxury. Welcome to this luxury coastal retreat on North Siesta Key, perfectly positioned inside Sarasota city limits, making it a rare short-term rental–friendly opportunity. With deep water access just seconds from the Bay, two boat lifts, and a jet ski lift, this home is tailor-made for boaters, water enthusiasts, and investors seeking a strong rental return. Property Highlights • 3 bedrooms | 3.5 bathrooms | Bonus room • Over 4,300 sq. ft. of living space • Nearly 5,000 sq. ft. total under roof • Prime North Siesta Key location in city limits • Quick drive to Downtown Sarasota and Siesta Key Village • Short-term rental potential in one of Sarasota’s hottest markets Interior Features As you step inside, you’re greeted by soaring vaulted ceilings and gleaming oversized porcelain white tile floors that set the tone for the home’s regal, modern style. • Living Room: Expansive and open with dramatic volume ceilings • Bonus Room: Hidden retreat above the garage ideal for a quiet office, playroom, or guest space • First Suite: Convenient en suite bedroom on the main floor • Primary Suite: Oversized retreat with a private screened lanai, spacious walk-in closets, and a beautifully remodeled spa-style shower • Third Bedroom: Private en suite with direct access to the pool deck The chef’s kitchen and entertaining area have been fully remodeled with high-end finishes, blending function and style for both everyday living and gatherings. Outdoor Living Step outside to your large lap pool with water views, framed by paver decking and multiple lounging areas. With direct boating access, two boat lifts, and a jet ski lift, the water is truly an extension of your backyard. Key Upgrades This home has been renovated from top to bottom, ensuring a move-in-ready experience with timeless finishes and thoughtful design details.

548 Siesta Drive, Sarasota

$985,000
3 Beds 3 Baths Twitchell Ralph S Siesta Key Prop SubDv. 34242 Zip Code
One or more photo(s) has been virtually staged. Tucked away at the end of quiet Estrada De Costa, a single lane road with just three homes, this unique and spacious Siesta Key 3 bedroom/3 bath lakefront property offers rare privacy, flexibility, and charm. The home was expanded in 2001, the property includes a 2 bedroom/2 bath main house, and a fully equipped one bedroom/one bath separate suite with its own private entrance, cozy living room, kitchen, walk-in closet, and screened porch with tranquil water views. Ideal for multigenerational living, guest accommodations, or income potential. Saltillo(Mexican) tile flooring flows throughout both living spaces and adds character and charm to every room, while the open layout flows seamlessly for comfortable everyday living. Sliding glass doors on the water side fill the rooms with natural light. The house did have water in the home after Hurricane Helene, so the owner completed some thoughtful and stylish renovations such as Shaker cabinets, quartz counters, subway tile backsplash, all new LG stainless steel appliances, new AC, and hot water heaters in both living spaces, and solid paneled doors throughout. New roof in 2022, and drain pipes lines in 2024. Located on Lake Rittwood, a serene neighborhood pond teeming with tilapia, turtles, ducks and birds, this home is a retreat. Stroll into Siesta Key Village, or catch sunset views at the Big Pass/Gulf public access at the West end of Givens St. and Ocean Blvd. This home offers the end-of-the-road seclusion, but still close to the wonderful activities of Siesta Key and Sarasota. Whether you're hosting guests, housing extended family, or exploring rental potential, this unique layout offers flexible living options rarely found on the Key.

4830 Estrada De Costa, Sarasota

$2,000,000
3 Beds 4 Baths Hamilton Club SubDv. 34242 Zip Code
Exquisite waterfront townhome in private gated community with architectural detail in the Bermuda tradition. Lush tropical landscaping , dramatic pool area with view of lagoon and fountain and overhanging Oaks. Tennis and Pickleball Court. Deeded deep water protected dock with lift, electric and water at dock provided by the Association. No bridges to the intercoastal. This home has enchanting wide water views of the Bayou from almost every room. Mangroves make this body of water a beautiful environment for fish and other wildlife. A covered balcony overlooking the water is the perfect spot to sit and sip your cocktail. This home has been beautifully renovated with fine finishes and many artistic touches. Open gourmet kitchen witih large center island. Pantry, storage and corner sitting area with window seat. Impact glass windows throughout. Inviting great room with gas fireplace and charming ambiance. Three bedrooms with ensuite baths and large family room. Elevator from garage to second and third floor. Small enclosed yard on ground floor. Walk right out to your boat and enjoy all that Siesta Key has to offer. Located on the North end of Siesta, minutes to Shell Beach, Siesta Village and the famous white sand of Crescent Beach. Minutes by car to downtown Sarasota with endless cultural opportunities and fabulous shopping and restaurants.

3925 Hamilton Club Circle Unit 7, Sarasota

$1,450,000
3 Beds 3 Baths Shells On Siesta Key SubDv. 34242 Zip Code
The stunning three-bedroom, two-bathroom Spanish-style villa stands as a testament to resilience and quality. Experience peace of mind knowing this beautiful home endured no storm damage, standing high and dry with top-notch construction that allowed for zero impact from recent storms. Purchase with confidence, as this beachside sanctuary continues to shine. Nestled on a serene, private lane just off Beach Road, this enchanting villa offers unparalleled access to Sista Key Beach, with no roads to cross before your toes touch the soft, white sands and tranquil Gulf waters. Recent updates include a newer roof and air conditioning system, ensuring modern comfort for years to come. With its elegant Mediterranean charm and modern touches, the home invites you through a private gate and features luxurious glazed Spanish tile flooring, beautiful curved archways, and timeless bathroom accents. The villa boasts a a spacious layout with natural light flowing through every room, creating a warm and welcoming atmosphere. The thoughtful design includes an elevator for easy access across the levels and a charming open air terrace off the dining room, perfect for enjoying Florida's gentle breezes. A garden entry provides additional character, while partial Gulf views from the bedroom allow you to wake up to serene, coastal views every day. Parking is convenient with a spacious garage for tandem parking, complementing the vill's many desirable features. The low HOA fees (just $125 per month) and the flexibility of using the villa as a private residence or a desirable rental make this property a rare find. Plus, access to a pool is available if managed by Beachside Management. Don't miss the opportunity to own this elegant Mediterranean villa, perfectly positioned for beachside living on Siesta Key. Whether as a primary residence or investment, this property promises a life of luxury, tranquility, and unmatched Gulf-side beauty.

221 Tenacity Lane, Sarasota

$1,475,000
3 Beds 3 Baths Siesta Towers SubDv. 34242 Zip Code
Perched high above the shoreline, Residence 8C at Siesta Towers delivers nearly 360-degree views spanning the Gulf, Big Pass, Sarasota Bay, and the twinkling downtown skyline. From glowing sunsets to sparkling city lights, this vantage point is among the most extraordinary on Siesta Key. Rarely available, this three-bedroom, three-bath residence has just undergone a complete, top-to-bottom remodel. Every detail was thoughtfully curated with today’s luxury buyer in mind—offering the ease of brand-new finishes within an iconic Siesta Key location. Designed with a sleek, modern aesthetic, the open floor plan showcases impact-rated windows and sliding glass doors, wide-plank luxury flooring, custom recessed lighting, and a seamless indoor-outdoor flow. The all-new designer kitchen is appointed with quartz countertops, custom soft-close cabinetry, premium stainless-steel smart appliances, and a striking island ideal for entertaining. Each of the three en-suite bathrooms has been fully redesigned with spa-level finishes, frameless glass showers, elegant tilework, and contemporary fixtures. The spacious primary suite is a retreat in itself, featuring a tranquil en-suite bath and panoramic water views. Siesta Towers is a secure, well-managed waterfront community offering an enviable lifestyle. Building amenities include secure access-controlled entry, 24/7 security, a remodeled club room, fitness room, heated waterfront pool, BBQ grills, fishing dock, social dock, bike storage, and more. Just beyond your door, Siesta Village’s restaurants, shops, and nightlife are a short stroll away, with the powdery sands of world-renowned Siesta Beach minutes from home. This residence combines the rarity of a three-bedroom layout with a brand-new, complete remodel and nearly all-around views—an exceptional opportunity to own one of Siesta Key’s most striking vantage points.

4822 Ocean Boulevard Unit 8C, Sarasota

$1,400,000
3 Beds 3 Baths Siesta Isles SubDv. 34242 Zip Code
JUST REDUCED!! SIESTA ISLES Waterfront Gem. Experience the best of Siesta Key living in this well maintained 3-bedroom + den, 3-bath pool home with 135+ feet of frontage on the Grand Canal. Situated on an oversized 15,269 sq ft /.35-acre lot, this residence offers the perfect blend of privacy, upgrades, and waterfront lifestyle. Situated well back from the street, the home opens with a welcoming foyer and expansive great room featuring vaulted ceilings, impact windows and impact sliding glass doors flooding the space with natural light while framing serene garden and waterway views. Two bedrooms feature en-suite baths and direct access to the back yard, while the primary suite’s bath connects conveniently to the pool area. Enjoy the privacy of this tropical retreat, swim in the sparkling pool, rinse off in the outdoor shower, or launch kayaks and paddleboards from the floating dock. With space to add a full dock or lift, boaters will love the water access via one fixed bridge to the Intracoastal Waterway. Practical updates bring peace of mind, including a durable metal roof and maintenance contracts for irrigation, AC, pest control, and alarm systems. The home has county water and sewer and there's a shared irrigation well that sustains the mature landscaping. The home experienced NO WATER INTRUSTION during last year’s storms and is truly move-in ready. A winding walkway through lush landscaping leads to the waterfront patio, while an extended brick paver driveway offers ample guest parking. Just minutes from Siesta Key’s world-famous beaches and The Village’s varied dining and shopping options, this home is ideal as a full-time residence or lucrative rental investment. Don’t miss your chance to own a slice of paradise on the Grand Canal—schedule your private showing today!

5215 Cape Leyte Drive, Sarasota

$1,595,000
3 Beds 3 Baths Siesta Beach SubDv. 34242 Zip Code
Just minutes from the powdery white sands of Siesta Beach and the vibrant energy of Siesta Key Village, yet tucked away on a quiet, oak-shaded street, 5121 Oxford Drive is a 3-bedroom, 3-bath waterfront pool home. Located on the coveted Grand Canal, with 50 feet of deep-water frontage, you’ll be on the bay in just minutes. A brand-new dock and 10,000 lb. lift (2025) are ready for your boat, and the property is golf cart–friendly, allowing you to cruise easily to the Village or beach. For the right buyer, furnishings, the golf cart, and even the boat are negotiable, creating a truly turnkey opportunity. Every major upgrade has been completed so you can enjoy the home from day one. Impact-rated low-e sliders and exterior doors (2025) fill the space with natural light and security. The durable metal roof is built to last, while all-new HVAC systems (2025), a whole-home dehumidifier (2025), and a tankless water heater (2023) ensure modern comfort. The garage features hurricane-rated insulated doors (2020), a mini-split A/C (2025), and epoxy flooring (2025)—perfect for keeping your toys protected in style. The gourmet kitchen, fully renovated in 2023, boasts quartz counters, high-end stainless steel appliances, custom solid wood cabinetry and a sleek coastal design. The master bath (2024) feels like a spa retreat, and even the fireplace area was refreshed in 2021, adding a warm focal point to the living space. The living area flows onto wraparound balconies made from Cumaru Brazilian teak, overlooking the sparkling new saltwater pool (2024) with electric heater, marble travertine pavers, and all-new equipment. This property is made for the lifestyle you’ve been dreaming about - morning coffee as boats glide by, afternoons on the water, and evenings walking or taking the golf cart to dinner in the Village. Whether you’re seeking a full-time residence, a vacation getaway, or a high-demand rental, 5121 Oxford Drive delivers it all - turnkey option, fully upgraded, and ready for you to enjoy.

5121 Oxford Drive, Sarasota

$1,577,000
3 Beds 2 Baths Sara Sands SubDv. 34242 Zip Code
***SELLER FINANCING AVAILABLE*** Tucked away on a quiet dead-end street, this exceptional waterfront estate on Siesta Key offers the perfect balance of seclusion and accessibility. Situated on an oversized 0.40-acre corner lot with 260 feet of water frontage and coveted western exposure, the property provides direct access to the Intracoastal Waterway—ideal for boating enthusiasts and water lovers. Just one mile from Siesta Key Village and the beach, the location allows for effortless enjoyment of island life while offering a private retreat. Move-in ready and untouched by flood damage, the estate includes two separate structures: a 2,000-square-foot main residence featuring an updated kitchen, and a versatile 280-square-foot detached building with a full bath—perfect for a guest suite, office, or creative studio. A newer metal roof and hurricane-impact windows and doors ensure lasting protection and peace of mind. Designed for outdoor living, the home features a spacious pool area with a large paver lanai, ideal for entertaining or relaxing. The property also includes a brand-new 10,000 lb boat lift, a double jet ski lift, and a newly installed well for efficient irrigation. After a day on the water or at the beach, unwind on the rooftop terrace and enjoy stunning sunset views over the water. This is a great opportunity to own a thoughtfully enhanced property in one of Siesta Key’s most desirable locations—offering the best of coastal living with modern amenities, luxury features, and sustainable upgrades.

5164 Windward Avenue, Sarasota

$700,000
3 Beds 2 Baths Whispering Sands SubDv. 34242 Zip Code
One or more photo(s) has been virtually staged. Welcome to this rare, NEWLY REMODELED 3 bed/2 bath, 1,562 SF freestanding villa with attached 2 CAR GARAGE in the premiere GULF FRONT Siesta Key property of Whispering Sands! NEW 2025 VILLA ROOF. Updated and completely move-in ready, this residence offers the ideal blend of privacy, modern updates, and coastal convenience—all just a two-minute stroll to your own private quartz sand beach on the Gulf! Every detail of this remodel has been carefully considered by its current owners. You’ll find NEW luxury vinyl plank flooring, NEW paint, interior doors & trim, and even NEW remote-controlled ceiling fans. The bright NEW kitchen is a standout with its soft close white cabinetry, modern backsplash, granite counters, and GE and Bosch stainless appliances. A set of handsome French doors leads from the dining area into your own private, gated and fenced brick paver patio, perfect for morning coffee, quiet evenings under the stars, or entertaining at the grill. The spacious primary suite features a valuable SECOND, custom walk-in closet. Both bathrooms have been refreshed with NEW granite topped vanities and fixtures. The rare 3rd bedroom could serve as either a guest bedroom or office or both. The star of the show might be the oversized 2-car garage which boasts an entire wall of valuable built-in cabinets, NEW full sized washer & dryer, epoxy floor, and sink. Window treatments include plantation shutters, shades, and blinds. Additional features include a tankless water heater, water softener, textured ceilings, recessed lighting & tubular skylights. Don’t miss this opportunity to own a newly remodeled move-in-ready villa in one of Siesta Key’s most desirable Gulf front communities!

104 Whispering Sands Drive Unit V27, Sarasota

$1,800,000
3 Beds 4 Baths Tiffany Sands SubDv. 34242 Zip Code
Gulf-front luxury townhome with private beach access on Siesta Key! Soak in the breathtaking, unobstructed views of the Gulf and iconic Siesta Beach from every level of this three-story, turnkey-furnished townhouse-style condominium. Just a short distance from the sand in the intimate, nine-residence enclave of Tiffany Sands, this rare Siesta Key offers blends relaxed beachside living with elegant design and modern comforts. Spanning 2,611 square feet, this three-bedroom, 3.5-bath residence welcomes you with an open-concept main floor that seamlessly connects the kitchen, dining and living areas—all framed by floor-to-ceiling impact-rated sliding glass doors and panoramic Gulf vistas. The living room is anchored by a cozy wood-burning fireplace and enhanced by crown molding, recessed lighting and sleek ceramic tile flooring. Go onto the expansive Gulf-front balcony, an ideal setting for alfresco dining or sunset lounging. The kitchen is stylish and functional, featuring solid-surface countertops, stainless steel appliances, modern cabinetry with pullout shelving, under-cabinet lighting and a breakfast bar for casual meals. Upstairs, the spacious Gulf-front primary suite offers postcard-worthy views, a private balcony, sitting area, double closets and a luxurious en-suite bath with jetted soaking tub, double vanity, separate shower, bidet and two skylights. Two additional guest bedrooms—flexibly configured with a retractable dividing wall—are also on the third floor along with a full guest bath and a well-equipped laundry room. The oversized ground-floor bonus room opens via sliding glass doors to a covered patio just steps from your private beach path. A full bath with walk-in shower was stylishly updated in 2024, making this level ideal for guests, a home gym or media lounge. Additional highlights include a one-car attached garage with extra storage, newer water heater (2024), HVAC (2022), roof and skylights (2017), hurricane shutters and flexibility of 30-day minimum rentals. Just .4 miles from Siesta Village’s vibrant shops and dining, and Siesta Beach Park, this exceptional home delivers the ultimate island lifestyle—whether you’re seeking a serene personal retreat, a seasonal escape or a savvy investment property.

546A Beach Road Unit A544, Sarasota

$1,850,000
3 Beds 2 Baths Midnight Harbor Sub SubDv. 34242 Zip Code
Siesta Key Waterfront Canal Home - Experience the best of waterfront living on Siesta Key with this charming canal-front home, just one house from the open bay and offering quick, easy access to the Intracoastal Waterway. Nestled in a tranquil and highly desirable location, the property enjoys a private setting on an expansive lot with a wide canal and stunning views of Sarasota Bay. This well-designed 3-bedroom, 2-bath residence sits high and dry, featuring an open floor plan perfect for entertaining. The spacious living and dining rooms flow seamlessly into the kitchen and family room, all enhanced by high ceilings and natural light. The master suite includes a cozy sitting area—ideal for a home office, den, or hobby room. On cooler evenings, relax by the wood-burning fireplace in the family room while watching boats drift by the bay. Outdoor living is equally inviting, with a sparkling pool and spa that provide the perfect retreat on warm Florida days. For boating enthusiasts, the property includes a dock equipped with a boat lift, water, electricity, swim ladder, and sundeck. Enjoy fishing, swimming, kayaking, or paddle-boarding right from your backyard. Upgrades include Roof (5 years old), A/C (3 years old). All hurricane impact windows & sliders and a 2 Car Garage. This home offers a rare opportunity to own a piece of Siesta Key waterfront—where every day feels like a vacation.

1236 Port Lane, Sarasota

$975,000
3 Beds 3 Baths Siesta Bayside SubDv. 34242 Zip Code
Price Improvement! Don’t Miss This Waterside East Gem in Siesta Key! Amazing opportunity to own a pool home with a seawall and dock—ready for your creative vision. Whether you choose to renovate and update the existing home or build a brand-new waterfront retreat, this location is unmatched. Tucked away on a peaceful cul-de-sac just off the Grand Canal, the home features: • Large circular driveway for easy access and ample parking • Open floor plan with split-bedroom layout for added privacy • Sparkling pool just resurfaced with brand-new equipment installed • Private dock with direct water access for boating and water activities While the home is in need of some updates, the potential here is incredible—whether as an investment property or your dream residence. All this, just minutes from world-class beaches, shopping, dining, and entertainment. Property is being sold As-Is—buyer to verify all information.

568 Venice Lane, Sarasota

$1,700,000
3 Beds 2 Baths Siesta Isles SubDv. 34242 Zip Code
Designer waterfront retreat on Siesta Key. Welcome to your dream coastal getaway! Tucked away on a quiet cul-de-sac, just moments from the world-renowned, powdery quartz sands of Siesta Beach, this impeccably renovated and landscaped waterfront home captures the essence of laid-back luxury and island living. Boaters will delight in the deepwater Grand Canal access—just one fixed bridge to Sarasota Bay and the Intracoastal Waterway, with direct Gulf of Mexico access. This fabulous single-level, three-bedroom, two-bath residence offers an open and airy floor plan filled with natural light, making it ideal for both full-time residence and an exceptional vacation retreat. A stunning 2023 designer renovation has infused the home with texture, warmth, and playful sophistication. From natural materials and artistic wallpaper to colorful accents and layered finishes, every detail is thoughtfully curated. Upgrades include new flooring, kitchen, bathrooms, plumbing, lighting, electrical systems, and front and garage doors. Enter through the statement front door into a welcoming foyer that opens to the expansive living room, featuring sleek, floating built-ins. The heart of the home is the striking kitchen and dining space, featuring a custom terrazzo island, quartz counters, Wolf and Miele appliances, and handcrafted cabinetry that offers generous storage. The island’s induction cooktop, drop-down exhaust fan, and bar seating blend form and function beautifully. A dedicated bar area with a wine cooler enhances the entertaining experience. The wide plank engineered oak flooring flows throughout, uniting each space with warmth and elegance. The spacious waterfront primary suite is a serene escape, complete with a spa-inspired bath, dual sinks, and a walk-in shower with private access to the pool. A thoughtful split floor plan provides privacy for two guest bedrooms and a second full bath. Even the laundry room is a showpiece, featuring art tile, a stacked washer and dryer, a beverage cooler, and whimsical details. Additional features include remote-controlled blinds, reverse osmosis in the kitchen, impact glass doors, windows, and garage door, an air-conditioned two-car garage with a paver driveway and walkways, Leaf Guard gutters, a 2023 HVAC system, 2023 attic and exterior insulation, and a 2020 roof. Seamless indoor-outdoor living begins with sliding impact glass doors that lead to the covered lanai and an oversized paver deck. Enjoy alfresco dining by the heated saltwater pool, resurfaced and retiled in 2022 with a sun shelf and spa also added for lounging. The lush, tropically landscaped backyard is fully fenced with faux turf, a putting green, and a fenced dog run, making it ideal for relaxation or play. Boating and water activities are a breeze from your private dock with a 14,000-pound remote-controlled lift, kayak launch, and seawall (2022). Just 15 minutes to open water, you'll savor days of fishing, paddleboarding, and Gulf cruising—right from your backyard. Ideally located near Siesta Village’s charming shops and restaurants, yet just minutes from mainland amenities, top-rated schools, and vibrant downtown Sarasota. Grab your flip-flops and sunscreen; this one-of-a-kind home offers the complete island lifestyle.

1031 Contento Street, Sarasota

$900,000
3 Beds 2 Baths Siesta Isles SubDv. 34242 Zip Code
OWNER IS MOTIVATED! PLEASE BRING A REASONABLE OFFER. WATERFRONT HOME HALF A MILE TO SIESTA BEACH. Welcome to 5572 Shadow Lawn Drive on Siesta Key. This 3 Bedroom, 2 Bath home sits on a 14,300 SQ. FT. LOT, has a private dock and features 102 FEET OF FRONTAGE ON THE GRAND CANAL. Only one fixed bridge at Midnight Pass Rd means GREAT BOATING ACCESS to Sarasota Bay and the Gulf. Or take a short bike ride or walk to SIESTA BEACH, the #1 beach in the US. This spacious home has over 2,000 Sq. Ft. of living area. It had minor flooding during Hurricane Helene. The water and carpet were quickly removed. Removal of the carpet revealed Terrazzo Floors in the main part of the house. THE PRIME WATERFRONT LOCATION CLOSE TO THE BEACH makes this property an excellent candidate to use as your MID-CENTURY STYLE beach retreat, or to BUILD YOUR DREAM HOME. The existing home has a split bedroom plan that wraps around the LARGE SCREENED LANAI. Pocketing sliding doors lead to the spacious lanai from four rooms. From there, you will enjoy privacy, nice water views and quick access to your boat at YOUR PRIVATE DOCK. All three bedrooms are a good size. The Family Room is off the kitchen. This spacious room has its own mini split AC system and great storage space. The Inside Laundry Room has convenient built-ins and a small workshop area. An exterior door leads to the private outdoor shower. Very handy when you come back from the beach or boating. Small storage shed in back. In addition to the unbeatable beach and boating, this excellent Mid-Key location offers convenient access to the shops and restaurants of Siesta Village. Downtown Sarasota is a short drive away where you can enjoy various Theaters, Art Galleries, The Farmer's Market and fine dining. Motivated owner has made this the LOWEST PRICED WATERFRONT HOME IN SIESTA ISLES!

5572 Shadow Lawn Drive, 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

$900,000
3 Beds 4 Baths Siesta Beach SubDv. 34242 Zip Code
One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer | BEACH VIBES? Check, PRIME LOCATION? Check, HIGH END RENOVATIONS all completed in 2025? Check, check & check! Welcome to the ultimate in Florida living – whether you are looking to settle in full time or score an amazing SHORT TERM RENTAL/VACATION HOME, this one is a MUST SEE! Located in the heart of Siesta Key, this single story POOL HOME puts you just a 10 minute stroll to Siesta Key Village, and 5 minutes past that you are on the powdery sands of the world-famous beach. Nestled in a quiet, tree lined, no HOA community, you are living large with easy access to US-41, SR-72, and I-75. It’s the best of laid back island living with every modern convenience at your fingertips! Looking for CURB APPEAL? It’s through the ROOF (which was replaced in 2020)! With lush tropical landscaping, a circular paver driveway, covered portico, and an EV CHARGING STATION, the tone is set before you ever step inside. The covered front entry features a charming glass-inset front door that opens into an adorable foyer with immediate beach house energy. Inside you will find porcelain WOOD LOOK TILE FLOORS throughout and a living area full of personality – think vaulted TONGUE & GROOVE WOOD SLAT/BEAM CEILINGS, a cozy WOOD BURNING FIREPLACE, and CUSTOM BUILT-INS! You will appreciate the seamless flow into the light filled dining area, where sliding glass doors paired with a large window connects the interior to your outdoor oasis and includes a built-in bar and extra storage. The kitchen is a showstopper – a 2025 renovation with on trend TWO-TONE CABINETRY, stylish TILED BACKSPLASH set in a modern herringbone pattern, sleek QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, and a window over the sink so you don’t miss a second of the party outside. Enjoy idyllic indoor/outdoor living with a COVERED LANAI and the recently resurfaced SALT WATER POOL, complete with ceiling fans and new screens in the enclosure for maximum comfort, and convenient outdoor/pool bath access. The fenced backyard is both low maintenance and private – perfect for soaking up the Siesta Key sunshine! Last but certainly not least, your PRIMARY SUITE is a peaceful hideaway with a huge WALK-IN CLOSET, French door access to the lanai, and a spa-like en-suite bath featuring DUAL SINKS under LIGHTED MIRRORS, and a custom tiled walk-in shower behind seamless glass. Need space for guests, a home office or additional rental potential? The PRIVATE MOTHER-IN-LAW-SUITE is a game changer - delivering its own entrance off the pool area for endless versatility with additional pavered parking close by. Also take note of the NEWER A/C, UPDATED PLUMBING & WATER HEATER (2025), partial ELECTRICAL UPDATES, IMPACT GLASS/DOUBLE PANE STORM WINDOWS (most under 5 years old), and extra storage cabinets in the garage – to sum up Saint Albans Ave… The vibe? Fresh, modern and full of character! The location? Out of this world! The lifestyle? Pure Siesta Key magic! Call today!

5108 Saint Albans Avenue, Siesta Key

$965,000
3 Beds 2 Baths Ocean View SubDv. 34242 Zip Code
One or more photo(s) has been virtually staged. Incredible Value! Don't miss this one! Buy now and enjoy for season. Welcome to The Blue Lagoon... when you walk in it feels like new construction! A private modern coastal retreat perfectly positioned on Siesta Key’s tranquil Heron Lagoon... the ultimate vacation home or investment property. This exceptional, gated quarter-acre compound offers the rare combination of serenity, design, and functionality, ideally located between Turtle Beach and Crescent Beach, just moments from the iconic Point of Rocks. Enter through a secure electric gate framed by custom wood fencing and arrive under a majestic live oak canopy that sets the tone for the natural beauty and privacy within. Designed to maximize indoor-outdoor living, the home features two expansive screened lanais, a sparkling private pool, an extensive wood deck, lush tropical landscaping, and a private dock where you can launch a paddleboard, kayak, or canoe directly into the peaceful lagoon. The single-level custom residence offers a thoughtfully designed 3-bedroom, 2-bath layout with wide-plank wood-look tile flooring in soft white and gray tones, crisp white walls, black metal hardware, and premium wood and metal ceiling fans throughout. Soaring ceilings are clad in hand-cut cypress wood shiplap, adding both natural warmth and acoustic insulation. The gourmet kitchen is a chef’s dream, featuring high-gloss European cabinetry, quartz countertops, a striking wood-grain tile backsplash, and Café Series stainless steel appliances including a six-burner gas range with a double oven and a counter-depth French door refrigerator with filtered and instant hot water. A whole-home water filtration system ensures pure water at every tap. The spacious master suite is a true sanctuary with a double-closet hallway, soaring ceilings, and a large window and sliding glass door that open to the lanai. The spa-inspired en suite bath features floating dual white European vanities, a luxurious rainwater shower with Kohler gold fixtures, floor-to-ceiling “blue skies” tile, and organic gray cobbled stone flooring. The peaceful sound of rainfall on the metal roof at the rear of the home enhances the retreat-like experience. The guest bath offers equally sophisticated design, with iridescent honeycomb tile behind a deep soaking tub and rich gray tilework throughout. Every detail of this home has been carefully curated to reflect the essence of the Siesta Key lifestyle, luxurious, relaxed, and deeply connected to nature. Whether you’re looking for a full-time residence or a seasonal escape, The Blue Lagoon offers a once-in-a-lifetime opportunity to own a coastal property where water views, natural beauty, and modern comforts unite in perfect harmony. In addition to being a stunning private residence, this property is also ideal for seasonal use or as a high-performing vacation rental. Similar properties on Siesta Key routinely generate over $100,000 per year in rental income, making this an excellent opportunity to enjoy the home while having it support itself or even contribute toward paying it off. Use it as a vacation retreat while earning income and always have a beautiful place to stay on Siesta Key. And if your long-term vision includes building your dream home, please inquire directly about available building plans for the lot by Island Series with Yoder Homes. Visit the link for a 3D tour, video and floor plan. https://nextlevelmediasrq.hd.pics/8234-Midnight-Pass-Rd/idx

8234 Midnight Pass Road, Sarasota

$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

$700,000
3 Beds 2 Baths Siesta Isles SubDv. 34242 Zip Code
One or more photo(s) has been virtually staged. Siesta Key Beach Retreat – Now $829,000 Welcome to 5223 Shadow Lawn Dr, a 3-bedroom, 2-bath home in coveted Siesta Isles, just 1 mile from the sugar sands of Siesta Key Beach. Located on a quiet cul-de-sac with preserve views and mature palms, this 1,459 sq. ft. property blends lifestyle, privacy, and investment potential. Inside, you'll find a bright open layout, modern laminate flooring, neutral finishes, and a renovated kitchen with granite countertops, stainless steel appliances, and crisp light cabinetry. The living area opens to a spacious screened lanai with a fully restored pool (completed October 2025)—now crystal clear and ready to enjoy. The primary suite features an updated en-suite bath, while two additional bedrooms and a second bath provide flexibility for guests, family, or a home office. With no HOA, 30-day rentals permitted, and a prime location near Siesta Village and Downtown Sarasota, this property delivers both lifestyle and upside. Highlights: - 3 Beds | 2 Baths | 1,459 Sq. Ft. - Fully restored pool (Oct 2025) - Renovated kitchen with granite & stainless - Spacious screened lanai + private preserve backdrop - Quiet cul-de-sac location - No HOA | 30-day rentals allowed - 1 mile to Siesta Key Beach One of the best-priced homes in Siesta Isles.

5223 Shadow Lawn Drive, 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

$715,000
3 Beds 2 Baths Siesta Beach SubDv. 34242 Zip Code
One or more photo(s) has been virtually staged. Nestled in a tropical setting, this charming newly updated 3-bedroom 2-bath "beach retreat" located one mile from Siesta Key ‘s #1 ranked beach internationally …checks all the boxes! New roof, new doors & hurricane impact windows – check! Upon entering a fresh, airy feeling is welcoming. From the ceramic-tiled living room your eye travels beyond the den area to the tropical outside setting, fully fenced private and secure. The kitchen is quality with all stainless appliances, quartz counters and light cabinetry. A separate dining area has easy access to the outdoor deck. Primary bedroom with new en-suite bath and luxury wood vinyl floors is located for privacy from the 2 guest suites with same type floors and bath blending whites and beige palette with marble counter tops and tile floors. A spacious laundry room with washer and dryer opens to the single car garage. Indigenous plantings and a circular paver brick drive and walkway add to charm and curb appeal. Located in a great family neighborhood and nearby Out-of-Door Academy. Ready for immediate occupancy this is an ideal choice for a winter retreat or an investment with unlimited rental possibilities.

755 Edgemere Lane, 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

$1,970,000
3 Beds 3 Baths Palm Bay Club SubDv. 34242 Zip Code
BREATHTAKING amazing Gulf of Mexico views and ONCE IN A LIFETIME OPPORTUNITY for this ONE-OF-A-KIND condominium residence in the desirable Gulffront Tower building in the Palm Bay Club on the island of Siesta Key. This turnkey furnished residence is a combined 2-bedroom unit with the adjacent 1-bedroom unit, redesigned to create a fabulous 2-bedroom plus den/study, which could be converted back to a third bedroom. On the desirable southwest corner of the fifth floor, walls of glass allow for dramatic panoramic beach and Gulf of Mexico views. Every room has stunning views of the wide, white quartz-sand beach of #1 Siesta Key beach and the azure Gulf of Mexico. The spacious, light-filled living room has marble floors with a separate dining area. In the kitchen you will find a Subzero refrigerator, an eat-at breakfast bar, ample storage, a pantry room and a view overlooking the beach as you prepare your meals. The owner's suite boasts French doors, a sitting room, a boudoir bathroom with jetted tub, grass cloth wallcoverings and a view looking south down the beach. The guest bedroom is private with an incredible Gulf of Mexico view and ensuite bathroom. The study could be converted back to a third bedroom but currently has a wet bar, many built-ins, work desk and amazing views. This residence includes a powder room, 2 air conditioners, 2 water heaters, newer washer/dryer, surround sound, turnkey furnished and is just waiting for your personal touch and update to make it your own. Resort amenities include private deeded access to white-sand beaches and beach chairs, two heated swimming pools (one beachside), large hot tub and pool overlooking the Intracoastal waterway, barbecue grills, fishing pier, lighted tennis & pickleball courts, fitness center, complimentary wifi and 24-hour security. EXCELLENT RENTAL POTENTIAL as the Palm Bay Club offers an upscale rental program with a 3-day minimum rental policy which is an attractive opportunity as an investment, winter retreat or primary residence. Enjoy the island lifestyle only minutes from the boutiques, fun restaurants and entertainment in Siesta Village and a short drive to museums, theater, art galleries & restaurants in downtown Sarasota.

5966 Midnight Pass Road Unit G-51 & G-58, Sarasota

$2,190,000
3 Beds 2 Baths Crescent Siesta Key SubDv. 34242 Zip Code
Welcome to luxurious, maintenance-free beachfront living at prestigious Crescent Siesta Key Condominiums. This 1,800-square-foot turnkey-furnished unit offers three bedrooms, two full baths, a laundry room and two large balconies, one with beach views, and the other overlooking the second-level Crescent pool/courtyard. The inviting open floor plan includes a large dining room. The kitchen is open to the dining room and living room. Poggenpohl (luxury German-made) cabinets, stainless appliances, large breakfast bar and spacious pantry/storage cabinets line the hallway. It is near south Siesta Key Bridge with shopping, entertainment and dining across the street. The Crescent is a boutique complex of only 26 units and offers direct beach access, a gulf-view pool with whirlpool hot tub, as well as a single-lane lap pool, a gourmet poolside summer kitchen and a beautifully landscaped garden terrace with poolside seating. It includes well-appointed common areas, elevators to all floors, a clubhouse, a fitness room, reserved two-car covered parking, a car charging station, on-site manager and 24-hour video surveillance with common areas secured by keypad access. It is a pet-friendly community for owners only. Investors alert! The unit is on the vacation rental program with Beachside Management, and it attracts lots of bookings. This is must-see.

6512 Midnight Pass Road Unit 303, Sarasota

$913,500
3 Beds 2 Baths Sarasota Beach SubDv. 34242 Zip Code
Beachside Oasis with Income Potential – Just 2 Blocks from Siesta Key Beach! Welcome to your slice of paradise! This spacious 2,956 sq ft single-family home is perfectly positioned just two blocks from the world-famous Siesta Key Beach. With 3 bedrooms and 2 bathrooms on the upper level, plus a fully equipped 1-bedroom 1-bath apartment/in-law suite with private entrance on the lower level, this property offers flexibility for multi-generational living, guest accommodations, or short-term rental income (lower level is considered non-conforming living space and has been remediated from damage caused by 2024 hurricanes). The home boasts a private heated pool surrounded by lush landscaping and vinyl privacy fence down each side , ideal for relaxing or entertaining. Major upgrades provide peace of mind, including: New roof (2023), Re-piped plumbing (2021), Updated electrical panel (2021), New upper-level AC unit (2022), Pool pump replacement (2024), Impact windows in the main house. Enjoy open, airy living spaces with coastal charm, and take comfort knowing you're minutes from dining, shopping, and all the vibrant energy of Siesta Village. Whether you're looking for a forever home, a beachside getaway, or an investment with high rental appeal—this property has it all. Home is being sold furnished, with the exception of a few personal items.

5385 Avenida Del Mare, Sarasota