Siesta Key Homes with Bay/Harbor Frontage

Siesta Key Homes with Bay/Harbor Frontage

Welcome to Siesta Key, Florida, a picturesque barrier island renowned for its stunning beaches, vibrant culture, and laid-back lifestyle. Nestled in Sarasota County, Siesta Key is a tropical paradise that offers residents and visitors alike an unparalleled experience, characterized by its powdery white sand beaches and crystal-clear waters. The island is a haven for outdoor enthusiasts, providing ample opportunities for boating, fishing, and water sports, all while basking in the warm Florida sun.

One of the most alluring aspects of Siesta Key is its exclusive homes with bay and harbor frontage. Imagine waking up to breathtaking views of the shimmering waters, where the gentle lapping of the waves sets the tone for a serene day. These waterfront properties offer not only a luxurious lifestyle but also direct access to the bay, making it easy to embark on a sunset cruise or simply enjoy a quiet afternoon by the water. The homes here are designed to capture the essence of coastal living, featuring open floor plans, expansive decks, and lush landscaping that seamlessly blend indoor and outdoor spaces.

Siesta Key is not just about picturesque views; it’s a vibrant community with an array of dining, shopping, and entertainment options. From charming boutiques to gourmet restaurants, there’s something for everyone. Whether you’re looking for a seasonal retreat or a permanent residence, Siesta Key’s waterfront homes offer a unique opportunity to live in a slice of paradise. Embrace the coastal lifestyle and explore the enchanting allure of Siesta Key today!

Newest Siesta Key Homes with Bay/Harbor Frontage

8773 Midnight Pass Road Unit 504G, Sarasota
$615,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
Welcome home to your tropical retreat at Island Reef on south Siesta Key! Island Reef is a Gulf to Bay resort style community. Amenities include: 2 heated pools, private beach, pickleball, tennis, clubhouse and docks. There is an active social calendar and in-house rental management as well. This beautiful penthouse unit has a wonderful pool and courtyard view. 504G is being offered Turnkey Furnished. This beachy condo has been extensively upgraded including the kitchen, both bathrooms, a laundry with full-size washer and dryer, and a raised ceiling in the dining area. The knotty pine floors and doors are reminiscent of a coastal cottage. Indirect lighting can be dimmed to suite your needs. A new AC was installed in Oct 2026 and the warranty will be transferred to the new owners. The kitchen and bathrooms have solid wood paneled cabinets, granite countertops, and subway tile bath and shower surrounds. In the kitchen the lighted cabinets allow for a beautiful display of dishes, glassware, and favorite collectibles. The living room and dining area have comfortable coastal furniture. The large dining table holds 6-8. Glass sliding doors open to a garden style lanai with slate tile flooring. Enjoy the tropical breeze and pool view while sipping your morning coffee on this wonderful lanai. Throughout the condo there are several unique antique wood chests and other furniture pieces., which are perfect for additional storage. The coastal artwork and knick-knacks are included in the purchase of this home. From the primary bedroom, you can also access the lanai through sliding glass doors. There is a large walk-in closet and an ensuite bathroom with dual sinks and large shower. The guest bedroom has a three-piece full wall shelving /desk unit. There is also a full wall built-in closet. Across the hallway is a laundry and storage room. If you are ready to make a move to paradise, please call for a private showing. When you see 504G you will fall in love! Buy now and enjoy winter on Siesta Key!

8773 Midnight Pass Road Unit 504G, Sarasota

7535 Midnight Pass Road, Sarasota
$4,500,000
5 Beds ⋅ 2 Baths ⋅ Sub Of Us Lt 7 Of 20-37-18 SubDv. ⋅ 34242 Zip Code
For the first time since 1925, the same Sarasota family is bringing 7535 and 7539 Midnight Pass Road to market, offered together as nearly one acre on Siesta Key. The two parcels total 0.95 acres, with 7535 offering over 100 feet of direct waterfrontage on Little Sarasota Bay, a reinforced concrete seawall, and access to the Intracoastal Waterway. The main home was designed by Jack West, a celebrated architect of the Sarasota School of Architecture. The charming second home on the adjoining parcel was designed by his onetime partner, Elizabeth Boylston, the first woman in Florida elected to the American Institute of Architects. This second residence offers two bedrooms, one bathroom, and 1,016 square feet, in addition to the MLS-listed totals. A detached two-car garage provides additional parking and storage. Walls of sliding glass and graceful midcentury lines open the main house to the garden and the water. Framed by lush tropical greenery, the combined site presents a rare opportunity to create a waterfront compound with a main residence, guest house and gardens. An additional adjacent 0.53-acre lot may also be available for purchase at an additional price, offering an opportunity to expand the property even further. A 2016 dock with a 13,000 lb boat lift provides access to the Intracoastal Waterway, where mornings begin with soft golden light over Little Sarasota Bay. Turtle Beach, Crescent Beach, and the powder-soft white sand of Siesta Beach are minutes away, with Siesta Key Village, downtown Sarasota, and Sarasota Bradenton International Airport all within easy reach. For the buyer who has been waiting for the right piece of Siesta Key, this is it: nearly an acre of land with direct bayfrontage, a seawall, dock and lift already in place, complemented by an architectural legacy and history that cannot be replicated. Create the waterfront home you have always imagined on land that has been cherished by the same family for over a century and is now ready for its next chapter.

7535 Midnight Pass Road, Sarasota

1260 Dolphin Bay Way Unit 203, Sarasota
$1,150,000
2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Discover the relaxed elegance of waterfront living at Dolphin Bay, one of Siesta Key’s desirable gated condominium communities. Enjoy beautiful views of Sarasota Bay from this spacious two-bedroom, two-bath residence offering 1,915 square feet of thoughtfully designed living space, complemented by multiple outdoor areas that invite you to embrace the coastal lifestyle. Bright, welcoming interiors feature an expansive living and dining area, a separate family room, and a beautifully refreshed kitchen with white quartz countertops, freshly painted cabinetry and an inviting breakfast bar. A unique and thoughtful feature is the remote-controlled privacy screen that separates the family room from the kitchen, creating a comfortable, temporary guest retreat when needed. This versatile space offers added flexibility for visiting family and friends while preserving the home's open, inviting design. Hard-surface flooring flows throughout, while the split-bedroom floor plan provides privacy and comfort, with both bedrooms featuring en-suite baths. The generous covered rear lanai extends the living space outdoors, offering peaceful views of the tropical grounds and sparkling bay beyond. A covered front terrace and additional sunning deck provide even more opportunities to enjoy Siesta Key's beautiful weather. Additional highlights include a private one-car garage beneath the building, ample guest parking, and a new HVAC system and water heater installed in 2024. Dolphin Bay offers an exceptional combination of waterfront beauty and resort-style amenities, including a clubhouse, swimming pool, spa, tennis courts, fitness center and day dock. This gated, pet-friendly community enjoys a convenient location near Siesta Key's celebrated beaches, with the island trolley just outside the entrance connecting you to the restaurants, shopping and entertainment of Siesta Village. Whether enjoying a quiet morning overlooking the water, entertaining friends or spending the afternoon at the beach, this inviting residence captures the comfort, versatility and effortless enjoyment of the Siesta Key lifestyle.

1260 Dolphin Bay Way Unit 203, Sarasota

4196 Roberts Point Circle, Sarasota
$10,890,000
6 Beds ⋅ 8 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code
Set on 1.34 waterfront acres in one of Sarasota’s most extraordinary settings, 4196 Roberts Point Circle presents a rare opportunity to own a private residential compound surrounded by water, mature tropical vegetation and sweeping views across Sarasota Bay. With over 400 feet of waterfront and an exceptional sense of privacy, the property offers a setting that is increasingly difficult to replicate on Siesta Key or anywhere in the Sarasota area. For a buyer drawn to architecture with history and individuality, the existing compound offers an opportunity for renovation and transformation. For those envisioning something entirely new, the acreage and waterfront position provide an exceptional canvas for creating a landmark Sarasota estate. The property also has the potential to be divided into multiple parcels and redeveloped as incredible bayfront homes. Most compelling is the location on the coveted north end of Siesta Key, an area prized for its privacy, larger properties and peaceful residential character while remaining close to everything that makes the island so desirable. The structures encompass approximately 8,500 square feet of living space with six bedrooms and eight baths. Distinctive architecture, extensive use of natural wood, vaulted and beamed ceilings, expansive walls of glass and wraparound outdoor living areas give the residence a character entirely its own. The main residence features generous gathering spaces framed by windows and French doors, warm wood flooring, a dramatic open staircase, and an expansive primary suite with vaulted ceilings. Multiple living and entertaining areas provide flexibility for reimagining the interiors while preserving the property’s architectural personality. The guest house is perfect for guests, extended family, private offices, studios, or multigenerational living. Outdoors, the expansive grounds unfold toward the shoreline with a swimming pool, mature landscaping and multiple docking options providing direct access to the water. From the shoreline and elevated living spaces, broad views stretch across Roberts Bay to the mainland while the scale of the 1.34-acre parcel creates a remarkable sense of openness and seclusion. Siesta Key is celebrated for its laid-back coastal lifestyle, vibrant Siesta Key Village and extraordinary beaches, including Siesta Beach, renowned for its powdery white quartz sand and previously named the No. 1 beach in the United States by Tripadvisor. From this private waterfront retreat, downtown Sarasota’s dining, shopping, and cultural attractions are also just minutes away, creating an exceptional combination of island seclusion and mainland convenience. This is a rare opportunity without compare on the Gulf Coast.

4196 Roberts Point Circle, Sarasota

4196 Roberts Point Circle, Sarasota
$10,890,000
Roberts Point SubDv. ⋅ 34242 Zip Code
An extraordinary land opportunity without compare on the Gulf Coast to create a legacy waterfront estate, multi-residence compound or two distinctive estate homes on 1.34 acres along Sarasota Bay. Located at 4196 Roberts Point Circle, this expansive Siesta Key property offers over 400 feet of waterfront, remarkable privacy, and sweeping views across the bay in a setting rarely available at this scale. The size and configuration of the property present compelling possibilities for its next chapter. Envision a singular custom waterfront estate surrounded by lush grounds or explore the potential to divide the property and create multiple residences—an exceptional opportunity for a private family compound where generations can live independently while sharing one extraordinary waterfront setting. Any subdivision or redevelopment would be subject to applicable zoning, permitting, and governmental approvals. The property currently contains approximately 8,500 square-foot of living space among two structures, allowing a future owner to consider incorporating existing improvements into a new vision or pursuing a more comprehensive redevelopment of the site. Mature tropical vegetation surrounds the property, creating a natural sense of seclusion, while the expansive shoreline opens to panoramic water views. Multiple existing dockage options provide direct access to the surrounding waterways, further enhancing the property’s connection to Sarasota’s coveted coastal lifestyle. The 1.34-acre site offers substantial space to thoughtfully orient residences and outdoor living areas around the water, with possibilities for resort-style amenities, gardens and gathering spaces that take full advantage of the property’s scale and setting. Whether preserved as one expansive homesite or reimagined for multiple residences, the property represents an increasingly rare opportunity to create something entirely personal on the water. Its location on the coveted north end of Siesta Key makes the opportunity even more exceptional. Known for its privacy, established residential character and sense of seclusion, this quieter end of the island offers a distinctly different experience while keeping Siesta Key Village, mainland Sarasota, and the island’s celebrated beaches within easy reach. Siesta Beach is renowned for its powdery white quartz sand and has previously earned Tripadvisor’s distinction as the No. 1 beach in the United States. Downtown Sarasota’s acclaimed dining, shopping, arts, and cultural destinations are just minutes away, as is Sarasota-Bradenton International Airport. It is a rare convergence of significant acreage, waterfront, privacy, and the unmistakable lifestyle of Siesta Key.

4196 Roberts Point Circle, Sarasota

609 Norsota Way, Sarasota
$8,500,000
Bay Island SubDv. ⋅ 34242 Zip Code
An extraordinary opportunity to create a custom waterfront estate on coveted Norsota Way, where spectacular panoramic views stretch across Sarasota Bay to the downtown skyline and Ringling Bridge. Positioned on an exceptional 0.57-acre homesite in the prestigious Bay Island neighborhood of Siesta Key, this rare property offers an impressive 370 feet of combined water frontage, including approximately 168 feet directly on Sarasota Bay and 202 feet along the protected yacht basin. With expansive open-water views, a generous homesite, and exceptional boating access, this is a remarkable setting for a one-of-a-kind Sarasota waterfront residence. The property's distinctive configuration offers the best of both worlds: sweeping, unobstructed views across the open bay and the convenience of protected water frontage along the adjoining yacht basin. Boating enthusiasts will appreciate direct access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico, with multiple waterways and destinations within easy reach. The extensive water frontage creates exceptional possibilities for designing a residence that embraces Sarasota's boating lifestyle. Spanning approximately 25,040 square feet, the cleared homesite provides an expansive canvas for a thoughtfully designed custom estate. Its generous dimensions and remarkable waterfront setting offer opportunities to incorporate substantial indoor and outdoor living spaces, expansive terraces, a resort-style pool, and beautifully landscaped grounds. Imagine walls of glass framing panoramic bay views, generous entertaining areas overlooking the water, and a private outdoor retreat designed around Sarasota's spectacular coastal scenery. The property's concrete seawall, irrigation well, and available public utilities add to its appeal as a premier waterfront building opportunity. Located on coveted Norsota Way within the established Bay Island neighborhood, the property is just moments from the mainland and the beaches of Siesta Key. This distinctive waterfront enclave is known for its beautiful homes, mature landscaping, and convenient access to Sarasota's finest amenities. Enjoy nearby Southside Village, with its popular restaurants, boutiques, and neighborhood charm, as well as convenient access to Sarasota Memorial Hospital, Marie Selby Botanical Gardens, and Downtown Sarasota's vibrant dining, shopping, theaters, galleries, and cultural attractions. The world-renowned white sands of Siesta Key Beach, Siesta Key Village, and Sarasota's picturesque bayfront are also just a short drive away.

609 Norsota Way, Sarasota

1313 Dockside Place Unit 120, Sarasota
$1,090,000
2 Beds ⋅ 2 Baths ⋅ Harbour Towne SubDv. ⋅ 34242 Zip Code
RARE BOATER’S OPPORTUNITY! 45' BOAT SLIP with NEW 27,000-lb IMM/Quality Platinum Series boat lift on deep, sailboat water! Completely renovated waterfront townhouse-style residence with the slip directly behind the unit—a highly desirable and rarely available location. Ultimate Beach lifestyle with easy access to Siesta #1 Beach & Siesta Village, just a few minutes' walk away. Enjoy mornings on the beach, afternoons on the boat, and evenings sunsets & exploring the Village. With many restaurants, music & shops. Fully remodeled down to the block walls with new plumbing, electrical, HVAC and ductwork, drywall, raised ceilings, LED lighting, and beautiful wood-look porcelain tile throughout. Gourmet kitchen features custom cabinetry, GE Profile appliances, natural quartzite, and abundant storage. Both baths offer easy-entry showers, and the primary suite includes a walk-in closet with custom organization. Private one-car garage, additional parking, attic storage, and newly screened lanai for entertaining. Elevated to 11.5' floor level remained free of stormwater during the 2024 storms. The dock features new pilings, full-length finger pier, fresh water, 30-amp/120V service, remote-controlled lift with auto-stop, and approximately 7' of water depth. Protected harbor approximately 100 yards from the ICW and just 10 minutes to Sarasota Big Pass. HOA permits boats up to 45' feet. Complex is getting a look and remodel! See photos Beach. Boating. Village life. All from one exceptional Siesta Key location. Community is going through a major face lift!! Scope of renovations • Siding/Trim/Facia with Stain-paint • Railings • Stairs • Gutter/Downspouts • Lighting

1313 Dockside Place Unit 120, Sarasota

894 Freeling Drive, Sarasota
$3,695,000
Bay Island Shores SubDv. ⋅ 34242 Zip Code
Zoning confirmation letter in from City of Sarasota. Ready for permitting and your custom dream home. This waterfront gem fronts Roberts Bay, facing Edwards Island, and offers unobstructed 180-degree views of dolphins, various bird species, and manatees. It's a perfect canvas for creating your customized residence. Located on the prized northern tip of Siesta Key, nestled on the Freeling Drive peninsula, this exquisite parcel blends sophistication with coastal living. Bay Island is renowned for its admired homes and architectural beauty, redefining island luxury along one of the area’s most pristine waterways. The oversized homesite is just under 15,000 square feet and features an impressive 155 feet of brand-new two-foot-elevated seawall, offering stunning panoramas. This location is ideal for boating and fishing enthusiasts, or for simply enjoying breathtaking sunrises and sunsets in unmatched natural beauty. Access on and off the island is easy, with Siesta Key Village's vibrant shops and restaurants, as well as the world-renowned Siesta Key Beach, just minutes away. Downtown Sarasota, with its galleries, theater, and fine dining, is also a short drive. Opportunities like this are rare, making this property a true gem for anyone seeking the ultimate waterfront address where privilege and prestige are embedded in an affluent lifestyle. I highly recommend experiencing the magic of this property for yourself. Choose any architect or builder to make your dreams come true. Owner will consider financing.

894 Freeling Drive, Sarasota

9393 Midnight Pass Road Unit 606, Sarasota
$649,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
Live your dream in this light and bright 6th-floor 2-bedroom, 2-bath condo with spectacular views of both the Gulf and the Bay! This unit is the perfect place to watch a sunrise or a sunset and soak in the beauty of Neville Preserve, Little Sarasota Bay, and the Gulf! Gorgeous bay views are showcased along the back of the unit through floor-to-ceiling sliders that span the entire space. The open kitchen features quartz countertops, white cabinetry, stainless steel appliances, and full Gulf views. The large master bedroom overlooks the Bay and features abundant closet space and an en-suite bath. A second bedroom and hall bath are ideal for family and/or guests. Additional conveniences include a washer/dryer in a closeted utility area and a ground level storage unit—perfect for beach and golf gear. An assigned covered parking space is conveniently located near the building entrance. Furnished and move-in ready!. The stack pipe replacement work for this unit has been completed and all association projects are paid for and there are no outstanding assessments. The Pointe, a unique community located at the southernmost end of Siesta Key, is surrounded by water on three sides. Just south of The Pointe, recently reopened Midnight Pass connects the Bay and Intracoastal Waterway to the Gulf - enhancing boating, estuaries, marine life, and real estate values! A gated property, The Pointe is beautifully landscaped and features every amenity: a heated pool and spa, lighted tennis and pickle ball courts, private boat docks, kayak and paddleboard racks and launch, exercise rooms, men's and women's saunas, a beautiful club house with a fireplace and a full kitchen, a private island with gazebo and grills, and on site management and maintenance. This five plus acre property is conveniently located just a few minute's walk from Turtle Beach and three restaurants. Come live at the less traveled, more tranquil end of the Key and enjoy the walking and bike paths under tree-lined Midnight Pass Road. Boat docks are available!!

9393 Midnight Pass Road Unit 606, Sarasota

Midnight Pass Road, Sarasota
$1,200,000
34242 Zip Code
PRICED FOR A QUICK SALE This rare and coveted 1-acre flag lot extends down to the Little Sarasota Bay Waterfront in one of the most desirable locales on the sandy barrier island of Siesta Key, across the street from the prestigious Sanderling Club. Imagine a canopied driveway leading to your secluded dream home, with immediate access to all that Siesta Key and the emerald green waters of the Gulf of America and the Intercoastal Waterway have to offer. You will enjoy your personal gateway to endless aquatic adventures, including boating, fishing, kayaking, paddleboarding, and shelling, or just relaxing on the beach. Stroll to your private dock extending approximately 235 feet into the bay waters, capable of docking a boat, jet skis, and kayaks. Walk or cycle 0.3 miles to the limited access Point of Rocks beach, a unique snorkeling and scuba diving spot, at the southern end of the world-renowned Siesta Key Beach, famous for its powdery white sands and calm, crystal clear waters. The Key’s South Village, adjacent to the island’s south bridge to the mainland, is a mere 1/2 mile from your front door. In addition to Siesta Key’s Best Beach Bars, South Village has a shopping area, grocery store, restaurants, fish market, and beach rentals, as well as a Marina, where your recreational boating needs abound. You won’t want to leave your new digs, but there is a lot more to this area. A tropical paradise married to a clean, vibrant city with a historic downtown is a rare combination, but it’s yours, only 7 miles up the coast in Sarasota, making it the epitome of Florida’s Sun Coast Living! In addition to its charming feel, Sarasota boasts a world-class Arts and Entertainment scene, with an array of upscale shops, gourmet restaurants, and vibrant nightlife venues to lure you out of your beach home for a “night on the town.” Indulge in a performance of a classic opera at the internationally acclaimed Sarasota Opera House, or catch a live blues show in a waterfront bar. Come claim your piece of Paradise! DRONE VIDEO ATTACHED TO THE LISTING! ***Also being offered as a Land Home Package! (See Photo #26) Call for additional information.

Midnight Pass Road, Sarasota

3200 Higel Avenue, Sarasota
$22,000,000
4 Beds ⋅ 7 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Welcome to 3200 Higel Avenue, an extraordinary new waterfront residence by Pham Development, nearing completion on one of North Siesta Key’s most exceptional stretches of shoreline, with construction anticipated to be complete within the next few months. Commanding approximately 190 feet of sailboat-water frontage along two sides, this two-story contemporary estate overlooks Sarasota Bay and Big Pass, with sweeping views toward South Lido Beach Park, Bird Key, and the Downtown Sarasota Skyline. Encompassing approximately 5,453 square feet under air and 6,852 square feet under roof, the residence features 4 bedrooms, 4 full baths, and 3 half baths, thoughtfully designed to embrace its spectacular waterfront setting. Rare Big Pass dockage, protected access along Bayou Louise, and private boating infrastructure—including a 30,000-pound boat lift for deep-water boating and a separate 10,000-pound jet-ski/kayak lift—provide effortless access to Sarasota Bay and the Gulf. Designed with a refined contemporary aesthetic, the interiors pair dramatic scale with refined materials and meticulous attention to detail. Soaring ceilings and expansive walls of glass frame the water and skyline, while engineered hardwood flooring, level-five finishes, and custom built-in walk-in closets elevate the home throughout. A striking glass elevator offers water views as it connects the home’s living spaces and rooftop level. The chef’s kitchen is centered around an oversized island and complemented by a walk-in pantry, high-end finishes, a Sub-Zero refrigerator, and Wolf oven, creating a beautifully appointed space for living and entertaining. The primary suite is a private waterfront sanctuary, capturing panoramic views and featuring a spa-inspired bath with dual vanities, a rain shower, and separate soaking tub. The primary-suite level also features its own private secondary living room, creating an intimate retreat separate from the main entertaining spaces, while a dedicated indoor gym provides space for wellness and fitness. Multiple balconies and covered lanais extend the living spaces outdoors, while a private saltwater pool and spa create a resort-inspired setting at the water’s edge. Crowning the residence, an expansive rooftop deck offers breathtaking panoramic views across Sarasota Bay, Big Pass, Bird Key, South Lido, and the downtown Sarasota skyline—an unforgettable setting for sunset cocktails and evening entertaining. Dolphins, manatees, fish, and native coastal birds are part of the remarkable natural setting almost daily, while the surrounding waterways invite paddleboarding, fishing, snorkeling, windsurfing, and boating directly from home. The residence remains just minutes from the powder sand of Siesta Key Beach and the restaurants, boutiques, and energy of Siesta Village. Downtown Sarasota’s acclaimed dining, galleries, performing arts, and cultural attractions are also easily accessible, providing a rare combination of privacy and proximity to the best of Sarasota. With approximately 190 feet of waterfront, exceptional deep-water boating capabilities, dedicated lifts for boating and watersports, a glass elevator with water views, an incredible rooftop deck, private wellness and living spaces, panoramic views spanning some of Sarasota’s most iconic landmarks, and a newly constructed residence just months from completion, 3200 Higel Avenue represents a rare opportunity to experience an elevated level of waterfront living on Siesta Key.

3200 Higel Avenue, Sarasota

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