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$1,001,000
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
Discover coastal-inspired living at its finest in this exquisite lakefront home nestled within **Bayside**, an exclusive Taylor Morrison-built community of just 49 meticulously landscaped, maintenance-free residences. As you step inside, your eyes are immediately drawn through the expansive great room to breathtaking water views that capture the essence of waterfront living. The great room offers generous space for both elegant entertaining and relaxed everyday enjoyment, enhanced by tray ceilings and elegant crown molding—among the many thoughtful upgrades found throughout the home. The gourmet kitchen is a standout, featuring quartz countertops, a large closet pantry, premium GE Monogram appliances, an LG refrigerator, and a spacious island with counter seating and dual sided cabinets. This space overlooks the lanai and pool, creating a seamless indoor-outdoor flow. Outside, the lanai is truly exceptional—an entertainer’s dream with a fully equipped outdoor kitchen, a cozy gas fireplace, both covered and open seating areas, and a sparkling saltwater pool and spa with gas heater. All of this is beautifully framed by a brand-new 2025 panoramic screen enclosure, offering sweeping views of the lake and abundant wildlife. The primary suite is a private retreat with stunning lake views with a luxurious bath featuring a spacious walk-in shower and a full wall vanity with dual sinks. The expansive walk-in closet includes custom built-ins for maximum storage and organization. A thoughtful split-bedroom plan ensures privacy, with Bedroom 2 offering an ensuite bath, Bedroom 3 conveniently located near the main bath, and a spacious den/office providing flexible living options. Additional practical features include a well-appointed laundry room with ample cabinetry and a garage equipped with its own split HVAC system. Bayside residents enjoy exclusive access to a private waterfront park overlooking the Intracoastal Waterway, with panoramic views of Casey Key and spectacular sunsets. This open space includes a day dock, kayak and paddleboard launch, fire pit, and generous lawn area—perfect for relaxing or gathering with friends. Located west of the trail with direct water access, this rare combination of lifestyle and location is nearly impossible to find. Homes like this don’t last long. Don’t let this one get away!

3936 Waypoint Avenue, Osprey
$2,995,000
3 Beds ⋅ 4 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.

14401 Masthead Drive, Osprey
$900,000
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
A beautiful story book home of Coastal living with mainland conveniences is ready for your discovery. Come see Bayside on Little Sarasota Bay a peaceful and friendly gated Intracoastal community of 49 landscape maintenance-free residences. Bayside residents enjoy access to a private waterfront park overlooking the intracoastal waterway view of Casey Key...oh the sunsets we have for you. Under rebuild is its day dock, kayak launch, fire pit, and event lawn with Adirondack chairs. Your new home is in model condition, and meticulously maintained by one homeowner. Built new in 2018 by Taylor Morrison homes, this Lazio floor plan is professionally decorated in a lighter Florida Coastal theme and has all the luxury features and conveniences you expect. Private preserve view over a heated south facing pool and spacious covered lanai for outdoor dining and living on a travertine deck (outdoor kitchen pre-plumbed). The split-plan design has three ensuite bedrooms, and a large den with French doors. Three stepped ceilings with crown molding, smartly placed recessed lighting, and wide plank laminate floors in all the active living areas. Your show kitchen has quartz countertops with designer accented backsplash, premium raised-panel cabinetry, a 117”x 60” island kitchen with prep sink, GE Café series stainless steel appliances, natural gas 5-burner cooktop, professional exhaust hood, wall microwave and convection oven. Owners’ suite has a large bay window, spa-like bath with walk-in shower, twin vanity sinks, well organized cabinet drawers and large 10’ x 11’ walk-in closet. Guest bedrooms 2 & 3 have their own wings and have ensuite baths. Convenient to shopping, great schools, and the gifted Pine View School, we are minutes to Siesta Key, Nokomis, and Venice beaches, the Legacy Bike Trail junction at Bay Street, Historic Spanish Point, the charming Venice Island Downtown District of quaint shops & restaurants, waterfront dining, Blackburn Pt. Park, and many restaurants. Two tours for you to explore this home: 3-D and a narrated tour.

3957 Waypoint Avenue, Osprey
$975,000
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
This stunning Taylor Morrison Lazio floor plan residence offers an exceptional blend of luxury and tranquility in a desirable West of Trail gated bayfront community. With breathtaking views of the sparkling lake and direct access to the bay, residents can enjoy picturesque sunsets and serenity of daily wildlife sightings. Newer sparkling pool and spa surrounded in pavers. The home features a modern design with meticulous attention to detail, highlighted by rich landscaping, landscape lighting and a tandem three-car garage with paver driveway. A private courtyard with a soothing trickling fountain welcomes you through the double-side light leaded door entry. Inside, a neutral palette and travertine flooring grace the main living areas, enhancing the home's elegance. With an impressive 2,344 square feet, the layout includes vaulted ceilings, three spacious bedrooms and three baths, all designed with an open concept in mind. An additional den/office provides flexibility for work or relaxation. Plantation shutters throughout. The chef-inspired kitchen is a culinary dream, featuring granite countertops, a single-level island with a breakfast bar, natural gas cooking and high-end GE Monogram stainless steel appliances, complemented by a dedicated bar area with a wine refrigerator. The owner's suite is a retreat, boasting a large, outfitted walk-in closet and a luxurious bath complete with a walk-in shower, dual sinks with wide vanities, and a separate toilet for added privacy. The home is equipped with impact windows and sliders, ensuring safety and energy efficiency, and there is a whole-house generator. This residence exemplifies indoor and outdoor living at its finest, making it ideal for entertaining or enjoying quiet moments in a fabulous setting. Maintenance-free landscaping included in low HOA fee, without a CDD fee and in a preferred X flood zone. In Bayside, you have access to a private waterfront park along Little Sarasota Bay, with fishing, a day dock for your boat, a kayak and paddle board launch, and a seating area with gas firepit, making it an ideal spot to capture magnificent Florida sunsets. With its prime location on a quiet cul-de-sac, this home promises an incredible lifestyle enriched by the natural beauty of its surroundings.

3904 Waypoint Avenue, Osprey
$1,210,000
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
Welcome to the epitome of luxurious and hassle-free living in the coveted community of Bayside, a gated waterfront community of 49 homes on Little Sarasota Bay. This immaculate, like-new home, built in 2016 on an oversized lot with serene, private preserve views, has been meticulously maintained and offers a host of premium features that discerning buyers will appreciate. Upon arrival, you’ll be impressed by the home's striking curb appeal. The spacious oversized three-car tandem garage is flanked by maintenance-free landscaping and irrigation, ensuring your exterior always looks its best. Enjoy the peace of mind of knowing all windows and doors are impact wind-rated to weather the worst of storms. On rare occasions the power may go out, a generator is on standby and ready to supply all your electrical needs for uninterrupted comfort. Step inside and you'll immediately notice the quality craftsmanship and thoughtful upgrades that set this home apart. Three spacious bedrooms and a dedicated office provide ample space for guests and room to work. The large great room seamlessly flows into the open kitchen, creating space for easy living, gatherings and entertaining. Speaking of entertaining, the amazing, screened lanai comes complete with a covered outdoor kitchen with grill and vented hood, granite countertops, sink, refrigerator and bar seating along with an additional dining area, gas fireplace, flat-screen TV and awe-inspiring heated pool/spa combo which includes a sun shelf. The kitchen is a chef's dream, featuring upgraded 42-inch cabinets with crown molding, soft-close drawers, under-cabinet lighting and quartz countertops. The island with pendant lighting and bar seating is ideal for casual dining and includes a secondary prep sink and additional front cabinets to provide ample storage. A tile backsplash and walk-in pantry add to the kitchen's charm, while top-of-the-line stainless steel appliances, including a gas cooktop, cater to your culinary desires. The great room features an octagon tray ceiling with crown molding, adding a touch of elegance to the space. The primary suite is an oasis, boasting an enormous custom-designed walk-in closet and a luxurious en-suite bath with quartz countertops, double sinks and a walk-in shower with frameless glass. A private water closet adds convenience and privacy. The guest rooms are on opposite sides of the house for added privacy, with one offering an en-suite bath. Throughout the home you’ll appreciate the wood-look plank ceramic tile flooring, 10-foot ceilings, 5¼-inch crown molding and 8-foot doors, creating an ambiance of luxury and sophistication. The laundry room is efficiently designed with numerous 42-inch upper cabinets, a built-in laundry sink with tile backsplash, and high-efficiency washer and dryer, making chores a breeze. Natural gas powers various amenities while a tankless water heater and water softener provide convenience and peace of mind enhancing your daily living experience. In Bayside, you have access to a private waterfront park along Little Sarasota Bay, with fishing, a day dock for your boat, a kayak and paddle board launch, and a seating area with gas firepit, making it an ideal spot to capture magnificent Florida sunsets. You are just minutes from Siesta Key Beach, Nokomis Beach, Legacy Trail, restaurants and shopping. Don’t miss out on this rare opportunity to experience Sarasota living at its finest!

3933 Waypoint Avenue, Osprey
$1,180,000
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
Discover Coastal Living at its Finest in the Exquisite Home within the Gated and Secluded Bayside Community, Overlooking Little Sarasota Bay! This Enclave of 49 Homes offers Residents Exclusive Access to the Intercoastal Waterway Via a Community Day Dock, Fishing Pier with Cleaning Station, Kayak and Paddle Board Launch, and a Fire Pit, Perfect for Enjoying Breathtaking Sunsets. Boasting 3 Bedrooms, 3 Baths, Plus a Den/Office, and an Oversized 2 Car Garage, this Home Exudes Luxury and Sophistication! Designer Touches Abound, Including 7 1/4-inch Baseboards, Crown Molding with Trey Ceilings, and a Central Vacuum system. The Chef’s Kitchen is a Culinary Masterpiece, Featuring a 5-Burner Natural Gas Cooktop and Hood, Stainless Steel GE Appliances, Built-in Oven and Microwave, Granite Countertops with a Large Island, and Walk In Pantry. Kitchen Seamlessly Flows Into the Great Room and Formal Dining Room all of which are Adorned with Travertine Floors. The Primary Bedroom Retreat Offers Luxury Vinyl Plank Floors, a Spacious Walk-In Closet, and an En Suite Bathroom with Dual Sink Vanity Boasting Quartz Countertops, along with a Huge Walk-In Shower. Step Outside to the Serene Outdoor Living Space, with Panoramic Screen Enclosure which Highlights the Preserve Views and is Perfect for Birdwatching, or for Relaxing by the Heated Pool and Spa and Outdoor Fireplace. The Lanai is Equipped with an Outdoor Kitchen Featuring Designer Tiled Backsplash, Gas Grill, Beverage Cooler, and Bar with Granite Countertops. Additionally there is a Doggie Door and Fenced Dog Run for Furry Friends to Enjoy. This Home Perfectly Combines a Secluded Coastal Lifestyle with Proximity to all that Osprey, Sarasota, and Venice have to offer! With Numerous Options for Restaurants, Shops, Beaches, and Golf Courses just Minutes Away, this Pristine, Move In Ready Residence Offers the Ultimate in Florida Living!

3925 Waypoint Avenue, Osprey
$1,200,000
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
Nestled within the highly coveted haven of Bayside, a gated community of 49 homes located on Little Sarasota Bay, this gorgeous, immaculate pool home with serene preserve views enjoys the benefits of coastal living combined with mainland convenience. Maintenance-free and just steps from the community’s waterfront park, you will enjoy luxurious living in this Taylor Morrison home that offers three bedrooms, three full baths, and a den/office. The gourmet kitchen’s quartz island and countertops, along with GE Cafe appliances, presents the perfect setting for home chefs, and overlooks the spacious dining and great room. The Primary Suite features bay windows with inviting views of the lanai, pool, and lush preserve beyond. The primary bathroom, elegant with quartz countertops, double vanities, and a spacious walk-in shower with two shower heads, adjoins the oversized walk-in closet complete with luxurious custom cabinetry. Once back into the great room, step through the sliding glass doors and you will be greeted by the screened lanai, beautifully designed with ceiling fans, well-appointed outdoor kitchen, salt-water pool, and spa, and view of the three-acre tropical preserve beyond. With high ceilings, crown molding, 8 ft. doors, large laundry room with cabinets and granite countertops, this sophisticated home includes an endless array of upgrades, including ceiling fans, tankless water heater, hurricane shutters and deluxe garage flooring. Furnishings are negotiable. As a resident of Bayside, you will enjoy the community’s private waterfront park and its unique amenities, which include a kayak/paddleboat ramp, a pier with a dock, and a fire-pit complete with Adirondack chairs . . . the perfect place to relax with friends and toast the colorful sunsets overlooking Casey Key. Bayside is just minutes from Siesta Key Beach, Nokomis beach, Legacy Trail, restaurants, and shopping. Don’t miss out on this rare opportunity to experience Sarasota living at its finest!

3937 Waypoint Avenue, Osprey
$1,050,000
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
Discover Coastal Living and Casual Elegance at Bayside, Osprey Florida Nestled within the gated enclave of Bayside, limited to just 49 homes, this hidden gem on Little Sarasota Bay represents Florida living at its finest. The community harmoniously blends active outdoor amenities with tranquil relaxation spots. From kayaking and paddleboarding to evenings by the fire pit or strolling along the waterfront boardwalk, Bayside offers a lifestyle that caters to all your desires. Positioned on a premium lot, this 2018 Taylor Morrison home overlooks a lush preserve, inviting nature's serene beauty right to your doorstep. The custom heated pool and spa, complemented by a spacious travertine decked screened lanai, become your haven for relaxation or entertaining. The outdoor kitchen only adds to the allure, promising delightful alfresco dining experiences. Inside, the home unfolds as a testament to modern luxury. Three bedrooms, three bathrooms, and a versatile den space offer ample room for comfort and creativity. The chef-inspired gourmet kitchen, featuring a gas range, an oversized island, granite countertops, and premium stainless appliances, is a culinary dream. Unique to this home is the extended garage, providing tandem parking or extra space for your hobbies and passions. Conveniently located near the Legacy Trail, Marie Selby Botanical Gardens, and various pristine beaches, the home is a gateway to the best of Florida. Dining opportunities and cultural experiences are just a short drive away, adding to the allure of this exquisite property. Experience the blend of sophistication and natural charm at 3973 Waypoint. This unique opportunity awaits you.

3973 Waypoint Avenue, Osprey
$1,150,000
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
Escape to your coastal oasis nestled within the exclusive enclave of Bayside, where luxury living meets the tranquility of Little Sarasota Bay. This newly built 3-bedroom, 3-bathroom residence, boasting an additional den/office, is a testament to perfection with upgrades at every corner. As you enter, be captivated by the breathtaking view of the southeast-facing preserve area, alive with the sights and sounds of nature. Step outside to nearly 500 square feet of covered outdoor space, complete with a travertine-tiled patio, outdoor kitchen, and a heated saltwater pool and spa – the epitome of Florida living. Inside, the open-concept floor plan seamlessly connects the gourmet kitchen, featuring high-end quartz countertops and top-of-the-line GE Cafe appliances, to the spacious great room and dining area. Entertaining is a breeze with custom lighting, tray ceilings, and a plethora of upgrades throughout. Retreat to the oversized master bedroom, a private sanctuary overlooking the pool and preserve. Indulge in the spa-like ensuite bathroom, boasting a walk-in shower with three shower heads and double vanity sinks. Two additional bedrooms, each with upgraded bathrooms, offer ample space for family and guests. Work from home in the office, complete with pocket sliding doors and a convenient Murphy bed. And with a three-car tandem garage and tankless hot water heater, storage is never an issue. Recent updates, including a new gas pool heater, landscaping package, and generator, ensure your home is equipped for comfort and convenience. Plus, enjoy yard maintenance included, leaving you more time to explore the nearby waterfront dining options, schools, and attractions. With easy access to Siesta Key beach, the Legacy Trail, and downtown Sarasota, your waterfront adventures await. And as a bonus, move in and start exploring with two kayaks and two paddle boards included! Don’t miss your chance to secure your slice of paradise in Bayside – where coastal luxury meets everyday convenience.

3961 Waypoint Avenue, Osprey
$1,367,500
3 Beds ⋅ 3 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code
Under contract-accepting backup offers. Enjoy the Sarasota lifestyle at Bayside on Little Sarasota Bay, a gated Intracoastal community of only 49 homes! This Taylor Morrison model home has 3 bedrooms (plus a den/office), 3 full baths, and has all the upgrades. Upon entering your vision goes to the open floor plan that flows to the travertine lanai with saltwater pool & spa. The Clearview screen offers unobstructed water views of the lake and preserve. The lanai has a spacious covered area with TV and a full outdoor kitchen. The kitchen has quartz countertops, premium raised-panel cabinetry, an expansive island kitchen with dual sinks and ample breakfast bar seating, GE Café series stainless steel appliances, natural gas 5-burner cooktop, exhaust hood, and microwave and convection oven. The Master suite has a large bay window with water views, spa-like bath with walk-in shower, dual vanity sinks, and a 10 x 10.5 walk-in closet with built in shelving and drawers. The garage has a flexible tandem three-car design. The community is maintenance free - your landscaping is part of your HOA. The community has a recreation area on the bayfront - a fishing pier/day dock, seating with a firepit, and a kayak/paddleboard launch area; perfect for watching the sun set over Casey Key. Bayside is convenient to shopping, restaurants, either Siesta or Nokomis beaches, Pine View School, and all that Sarasota has to offer.

3932 Waypoint Avenue, Osprey