Homes For Sale in Sarasota 34242 - 412 homes

Remarks: Under contract-accepting backup offers. Nestled in the quaint neighborhood along the Grand Canal on Siesta Key, this Key West style home offers the perfect blend of old-world charm and modern living. This well-appointed custom-built home has a spectacular open floor plan. The home's grand entrance welcomes you through a covered porch that leads to an oversized foyer. An abundance of natural light, beautiful canal views, soaring ceilings and gleaming hardwood floors create a bright and airy atmosphere throughout. You will then be charmed by the library with a sliding ladder, wood burning fireplace, walnut wood flooring, and cedar beams in the living room, all combined with modern style furniture. The open living area includes a kitchen, with cherry wood cabinets, and an Iron Elmira stove surrounded by Chicago brick, gorgeous dining room and a breakfast nook. Floor to ceiling windows and sliding doors seamlessly connect the grand living area to the outside covered deck, perfect for entertaining. The beautiful primary suite with canal views is on the main level and two generously sized bedrooms with their en-suite bathrooms are located on the upper level. A “basement room” between the two garages offers a huge amount of storage with built-in closets and cabinets. If interested to create an additional room/Office, a plan and design is available upon request.The house was not affected by any wind or flood damage thanks to its solid concrete block construction and 11ft elevation of living space. Some water intrusion on garage level, but did not cause any damage to building, or cabinets in storage area between the garages. The fenced-in backyard features a 35ft screened heated pool with a waterfall and Chicago brick deck. The 60ft IPE hardwood boat dock with a tropical over-the-water gazebo is equipped with a 10,000lb boat lift and offers plenty of space for all your outdoor toys. Boating just one mile through the deep-water canal brings you to the Intercoastal Waterway which leads right out into the open Gulf. In a market where quality counts more than ever, this home offers a rare blend of location, craftsmanship, and timeless appeal. Welcome home to Siesta Key - island living, breath-taking sunsets, boating and award-winning beaches, all at your doorstep.

Listing is courtesy of: CHARITY & WEISS INTERNATIONAL LLC (941-365-0022)

Listing Agent: Gabi Charity (941-685-6649)

Remarks: Welcome to Old World Siesta Key...this 1940s Bungalow Home was converted approx 40 years ago into a Triplex and a Cottage was added at the rear of the property. Siesta Key is World Renown for it's White Powdery Sand Beaches and is so convenient to the Mainland and all the Attractions Sarasota has to offer such as the Arts, St Armands and Unbelievable Shopping. The Property is located approximately three blocks behind Siesta Key Village, the Hub of Restaurants, Nightlife, and Shops, and there you will find this Graceful Triplex and Cottage. There are several Private Patios as well as Open Areas for Outdoor Entertainment and Relaxation both in the Front and Rear of the Triplex. There are Storage Units for Each Rental and there is a Shared Laundry Area in the middle of the Backyard. Convenience is really key for this Property as you can Walk to the Beach or the Village in 15 Minutes. Island Life is Unique, Exciting, Colorful but can also be Quiet and Slow, it's the perspective of the Offering and it's a sought after way of living. For the past 20 years the units have been long term rentals. Some of the tenants have been there for years and all four would like to stay and continue their Florida Island Lifestyle. Rents shown are the Expected rents that could be charged as the Owner currently charges less... just his way of doing business. There is one option that could change the dynamics and that would be to keep the Triplex as long term rentals and use the rear Cottage as an AirBNB and Owners Use unit. This would drastically change the income stream. The water and internet/cable is currently paid for by the Owner and the Electric is split between the Tenants based on unit size, of course all of this is subject to change based on the New Owner's intentions. This is an Amazing Opportunity to have both Income and Personal Enjoyment all wrapped up with a Special Place we call Siesta Key Living!

Listing is courtesy of: BLAKELEY & ASSOCIATES REALTY (941-567-3100)

Listing Agent: Lisa Blakeley (941-809-1647)

Remarks: Under contract-accepting backup offers. Welcome to Residence #201 at Halcyon Siesta Key—a rare opportunity within one of the island’s most exclusive boutique communities. With only six Gulf-front residences, Halcyon offers the ultimate in privacy, luxury, and architectural sophistication. This exquisite coastal retreat blends modern design with relaxed seaside living. Engineered hardwood floors, soft coastal hues, and floor-to-ceiling hurricane-impact windows frame sweeping views of the turquoise Gulf waters. Step off your private elevator into a bright, open floor plan designed for effortless entertaining. The gourmet kitchen features Wolf appliances, a wine fridge, and an oversized island flowing seamlessly into the dining and living spaces. The Gulf-front primary suite is a serene escape with a spa-inspired bath boasting dual vanities, a soaking tub, and a glass-enclosed shower. Two additional guest suites—each with private en-suite baths—offer exceptional comfort, while a versatile den/office provides flexibility for work or an additional bedroom. Unwind on your private Gulf-front terrace, where sunsets and sea breezes set the tone for everyday tranquility. Enjoy direct private beach access and the exclusive front amenity cabin, complete with a fitness center, bathrooms, comfortable lounge area, and an expansive deck ideal for entertaining or relaxing after a day by the water. A private two-car garage and resort-style amenities—including a beachfront pool and fire pit—complete this one-of-a-kind coastal lifestyle!

Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-321-5595)

Listing Agent: David Lehrman (941-321-5595)

Remarks: Owner Financing Available ~ Siesta Key ~ Siesta Key Beach - Private Beach Access ~ Gulf & Bay Bayside Community ~ Three Bedrooms ~ Two Bathrooms ~ Weekly Rental Property ~ Two Pools / Sauna's ~ Tennis ~ Pickleball ~ Day Dock ~ Garage (Deeded).This bright and serene two-story unit offers a welcoming second-floor entrance and is conveniently located just a short distance from the beach, making it truly move-in ready. As a weekly rental property, it is completely turn-key and situated within the desirable Gulf & Bayside Community. The residence features updates throughout and boasts an excellent layout designed for both comfort and style. Main Level Features: Upon entering, you are greeted by a light-filled kitchen equipped with a vaulted breakfast nook, stainless steel appliances, and a breakfast bar. The kitchen seamlessly flows into the dining room, which is enhanced by a wet bar and a beverage refrigerator, perfect for entertaining. The spacious living room, with its inviting vaulted ceiling, provides an ideal setting for gatherings and relaxation. The first-floor primary bedroom includes an ensuite bathroom that also serves as the guest bathroom. From here, you have access to the screened lanai, creating a seamless indoor-outdoor living experience. Tile flooring extends throughout the main level, except for the staircase leading to the upper floor. Upper Level and Additional Spaces: Upstairs, the home features a bright, multi-use loft area, as well as two luminous guest bedrooms. Each bedroom is complemented by a private Juliet balcony, and they share a bathroom with an enclosed shower. Additional conveniences include an in-unit stackable washer and dryer and a deeded, private one-car garage. Community Amenities: Residents of this community enjoy access to a variety of amenities, including private beach access, two pools, a sauna, a day dock, barbecue grills, tennis and pickleball courts, and a clubhouse. The property is beautifully showcased in photos and a drone virtual tour, inviting you to come and experience all it has to deliver. This is a weekly rental community, the management of which is at the discretion of the owner. Use the onsite management or one of your choosing. Easy to show even during active tenant stays.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)

Listing Agent: Robert T Anderson (941-350-8671)

Remarks: GET READY to experience breathtaking GULF-FRONT views unlike any other at this price! Completely remodeled with meticulous attention to detail, this exceptional two-bed, two-bath condo offers refined coastal living in one of Siesta Key’s most desirable areas…the heart of world-famous Siesta Key Village. From the moment you enter, panoramic Gulf views immediately capture your attention. Light-filled living and dining areas were thoughtfully designed to showcase the turquoise water, while neutral tones throughout create a relaxed coastal elegance. The kitchen blends style and function with granite countertops, a built-in desk, custom cabinetry, and all new Frigidaire Gallery appliances WITH induction cookware included. The master is a relaxing retreat with endless Gulf views, oversized walk-in shower, double vanity and spacious walk-in closet. The inviting guest bedroom and bath will have your guests planning their next visit before they even unpack. Architectural details include crown moldings, rounded corner walls, recessed lighting, and many designer finishes. Plus, newly installed 3-layer monolithic sliding doors with turtle tint, remote controlled solar shades, and 3 wall-mounted NEO LED TVs. This residence can also be sold turnkey furnished, allowing immediate enjoyment of the Siesta Key lifestyle. Amenities include 800ft of private beach, two pools, two clubhouses (one exclusively for tower residents), fitness center (coming soon) with new state-of-the-art equipment, beachfront tiki hut, BBQ grills, kayak/paddleboard storage, and beautiful new landscaping project underway soon. Few places combine this level of renovation, elevation, and Gulf views so close to Siesta Key Village—don’t miss this exceptional opportunity to own in one of Siesta Key’s most iconic beachfront settings. NOTE: Whispering Sands is considered a 55+ community; however, ownership is NOT age-restricted, making this an excellent option for anyone considering a vacation retreat or future home.

Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)

Listing Agent: Christa Spalding (941-529-6978)

Remarks: This charming one bed, one bath beach condo at the popular Palm Bay Club offers the perfect blend of comfort, style and coastal living. Perched on the gulf side of Midnight Pass Road, the Gulf of Mexico is just steps from your front door. With this prime location you’ll enjoy easy, private access to the powdered sugar sand of Siesta Key’s Crescent Beach, one of the gulf coast’s premier vacation destinations! The interior of the condo is thoughtfully designed and tastefully decorated to maximize space and function. The vinyl plank floors throughout are not only handsome but also afford a low maintenance foundation for the coastal décor. The kitchen offers bright white cabinets with bold black granite counters and attractive stainless appliances. The open concept living and dining room is nicely furnished and a welcoming space to recharge between sunny Siesta adventures. The lanai, which has been integrated into the living room, is enclosed with three glass sliders that permit abundant sunlight and can be opened for a refreshing saltwater breeze. The bedroom is a peaceful retreat with two beds for maximizing the guest allowance. An updated bath is not only attractive, but a pleasing space to refresh. A true beach to bay community, the Palm Bay Club delivers the ultimate Siesta Key owner opportunity with unlimited access to two heated swimming pools, a hot tub overlooking the peaceful intercoastal waterway, complimentary fitness center, lighted tennis courts with pickleball, boat docks (daily rental, 21 ft max), BBQ grills, and a fishing pier. A three night minimum rental policy and outstanding onsite management make this an enticing opportunity for the owner/investor!

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)

Listing Agent: Rudy Dudon (941-234-3991)

Remarks: Pre-Construction. To be built. Welcome to this newly imagined Siesta Key residence, a world curated for those with a sophisticated palate for modern architecture at the edge of the sea. Here, light dances across water and peers through your windows blending luxury, privacy and resort-style living within the exclusive enclave of Hidden Harbor. The journey begins as you approach this designer estate—a vision of coastal modernism, 4,900 square feet under air and meticulously crafted by TDI Coastal Homes, celebrated for precision, integrity, and elegance. Clean lines and natural textures blend with lush tropical surroundings, setting the stage for a life that lives like an endless retreat. The lower level invites you to linger outdoors surrounded by the scent of the saltwater breeze and the sounds of the cascading waters of the 65-foot infinity pool and spa. A covered living space blurs the line between home and horizon. A custom waterslide arcs playfully into the pool, while beyond, your private dock with a 20,000-pound lift awaits spontaneous voyages to Roberts Bay. Ascend by elevator or sculpted staircase to the heart of the home—spaces that feel both expansive and intimate. Walls of glass reveal shimmering water views, while the Meile appliance suite anchors a chef’s kitchen made for creating fine cuisine and lasting memories. Every detail and finish bears the signature of master craftsmanship. The home’s six bedrooms include two primary suites, each a retreat of its own with spa-inspired baths. Six full and three half baths offer both comfort and convenience for family and guests alike. A 700-square-foot bonus space stands ready to become whatever your imagination allows—a golf simulator, game lounge, or wellness studio. A three-car garage, new seawall, whole-home generator, and zero water intrusion during the 2024 storms provide unmatched peace of mind. As evening settles, the home transforms. Ambient lighting glows across the infinity edge and the hush of the bay replaces the day’s energy. You can almost hear the future stories unfolding here—laughter by the pool, sunrise swims, quiet coffee on the terrace. 5179 Hidden Harbor Road isn’t just a home; it’s a state of being—modern, effortless, and deeply connected to the water.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)

Listing Agent: Rudy Dudon (941-234-3991)

Remarks: Nestled behind the gates of the iconic Sanderling Club, widely regarded as one of Florida Gulf Coast’s only private, gated beachfront neighborhoods, this property offers a rare opportunity to establish a presence within one of Florida’s most storied coastal enclaves. Surrounded by multi-million-dollar estates and lush tropical landscaping, the homesite presents exceptional potential to capture sweeping Gulf views and create a truly remarkable coastal retreat. The existing residence is a charming 1953 beach house, distinguished by its original terrazzo floors and solid cast-in-place concrete construction, hallmarks of the durability and understated character that define mid-century coastal architecture. Offered as-is, the home provides a unique canvas for restoration, thoughtful renovation, or a visionary re-imagining that reflects the future owner’s architectural aspirations. Life within the Sanderling Club is defined by an unmatched Gulf-front lifestyle. Residents enjoy private access to pristine beaches, along with exclusive community amenities including tennis and pickleball courts set directly along the shoreline, a private marina, and the rare opportunity to swim in the clear Gulf waters alongside manatees and dolphins. Evenings often unfold beneath legendary Gulf sunsets, best experienced from the community’s historic clubhouse overlooking the water. Whether envisioned as a restoration of its mid-century charm, the site of a striking new architectural residence, or a long-term investment within one of Sarasota’s most coveted coastal neighborhoods, this property represents a compelling opportunity to become part of the enduring legacy of the Sanderling Club.

Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)

Listing Agent: Joel Schemmel (941-587-4894)

Remarks: Beaches, Boating & Bistros!!! Excellent Investment, 2nd Home or Build new. Island Style Canal Front Home on Siesta Key, steps to World Famous Siesta Village & the cool quartz sands of Siesta Beach. This Island Style 2 bed, 2 bath home in close proximity to all the food & exciting nightlife that Siesta Key has to offer. 1 car garage. This home on a Cul de sac is light & bright with Terrazzo floors for the laid-back Island lifestyle. New roof in 2022. Excellent rental potential with its ideal location makes this property a solid investment. Out back is a huge deck on the Canal that is perfect for waterfront get togethers. Updated kitchen with stainless steel appliances that opens up for entertaining with family & friends. Separate laundry room and a potting shed & workshop. After spending the day on your boat, either cook up your catch or stroll to your favorite Siesta Village establishment. Or, better yet, take a stroll on the Beach & enjoy Sunset.

Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)

Listing Agent: Dan Miller (941-376-7442)

Remarks: Charming mini-resort with lagoon-style pool and waterfall, sun decks, tropical landscaped gardens. Just steps from Siesta Key Public Beach. Free Trolley transports guests to Siesta Key Village for shopping, dining and a supermarket. Income Producing Property priced to sell at a Seven Cap. Two lots, 19 & 20 with 2 Duplexes.

Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)

Listing Agent: Tonna Gruber (941-232-8950)

Remarks: PRICE IMPROVEMENT. Exceptional Value on Siesta Key Rarely available and beautifully updated, this second-floor 1-bedroom, 1-bathroom residence in White Sands Village offers the perfect blend of coastal living and investment opportunity. Ideally located just across the street from Siesta Key Beach, the condo also enjoys a coveted view of the lush interior courtyard, providing a peaceful and serene setting. This turnkey furnished unit is move-in ready and features a bright, open floor plan with tasteful coastal updates throughout. The enclosed lanai adds valuable additional living space, ideal for relaxing or entertaining. The A/C system is serviced annually and is in excellent working condition, offering added peace of mind. White Sands Village is a hidden gem, known for its affordability, strong amenities, and rental flexibility. Residents enjoy a heated community pool, a newly renovated clubhouse with kitchen and gathering spaces, beautifully maintained grounds with paver roadways, and covered carports. Community boat docks are available on a first-come basis for a nominal fee. Small pets are welcome for both owners and tenants—an increasingly rare benefit on Siesta Key. With a two-week minimum rental policy and an on-site rental agent, this community supports steady income potential, making it equally attractive as a personal retreat or investment property. The nearby free Siesta Key trolley provides easy access to Siesta Key Village, dining, shopping, and downtown Sarasota’s cultural and dining scene. This price improvement enhances an already compelling opportunity to own in one of Siesta Key’s most desirable communities—where comfort, location, and income potential come together seamlessly.

Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)

Listing Agent: Jim Gammello (941-699-6283)

Remarks: Welcome to 450 Beach Rd Unit 4, a rare opportunity to own a completely remodeled 2025 coastal retreat just steps from the sugar-sand shoreline of world-famous Siesta Key Beach. Located within an intimate five-unit complex, this 3 bedroom, 2 bathroom condominium offers deeded beach access, sweeping Gulf views, and weekly rental flexibility. The interior was fully renovated in 2025 and features a bright, open layout designed for effortless coastal living, complete with sleek tile flooring, marble countertops, stainless steel appliances, and a seamless flow between the kitchen and living areas. Gulf views can be enjoyed from the kitchen, while the private balcony provides the perfect setting for morning coffee or sunset unwinding. Additional conveniences include one open parking space plus an enclosed one-car garage. Recent exterior improvements to the building and grounds include fresh paint, modern balcony railings, Italian terrazzo tile, contemporary privacy fencing, and luxury outdoor lighting, enhancing the curb appeal of this boutique property. Residents and guests enjoy a well-maintained shared pool and an entertainment area with a ping pong table, cornhole, and community poolside grilling area. Just a short stroll to Siesta Key Village, this property offers immediate access to dining, shopping, and nightlife while maintaining a private, resort-style atmosphere. Ideal as a full-time residence, second home, or high-performing investment, this property blends location, luxury, and income potential.

Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)

Listing Agent: Curt Ware (941-587-9122)