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$5,350,000
6 Beds ⋅ 5 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code
ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS ! Welcome to 622 Bayshore Drive - where coastal luxury meets modern sophistication on one of the most sought-after stretches of Little Sarasota Bay. Tucked away on a rare and expansive .78-acre gated estate, this custom-built, contemporary masterpiece offers 90 feet of pristine waterfront, unmatched privacy, and a lifestyle defined by serenity, style and seamless connection to the water. Designed for those who crave the extraordinary, this six-bedroom, five-bath residence is a showpiece of elevated design and quality craftsmanship, built just three years ago with the finest materials and storm-resilient features. Boaters will delight in the direct bay access just minutes from Midnight Pass and the open Gulf - a true water lover's paradise. Step through the grand entrance and into a world of light, space and unobstructed bay views. The soaring 14-foot bifold glass wall in the great room opens fully to a spectacular lanai, inviting indoor-outdoor living year-round. Imagine entertaining here – sunset cocktails by the saltwater pool and spa, laughter echoing across the water and every moment framed by nature's beauty. At the heart of the home lies a chef's dream kitchen, anchored by an oversized 7'X8' waterfall edge island and outfitted with top-tier Wolf, Cove, and Sub-Zero appliances. A walk-in pantry with second refrigerator/freezer ensures effortless hosting and everyday convenience. This home is as strong as it is stunning: constructed entirely of block and stucco, equipped with Category 5 impact-rated windows and doors, and elevated above flood level - a rare combination that provides peace of mind and impressively low insurance premiums. A whole-house generator ensures uninterrupted comfort. With its expansive yard, and panoramic water views, 622 Bayshore Drive is not just a home- it's a legacy property. Perfectly positioned between Sarasota and Venice, it offers the best of both worlds: quiet natural beauty with easy access to world-class dining, shopping and culture. DON'T JUST VISIT PARADISE - OWN IT. Schedule your private tour of this extraordinary waterfront estate today.

622 Bayshore Drive, Osprey
$3,650,000
4 Beds ⋅ 5 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code
Big bay views surround you from this exquisitely updated waterfront estate. Welcome to 324 Bayshore Drive, a property of nearly half an acre set on a large, open stretch of the bay with easy access to the Intracoastal Waterway. Even more spectacular is the beautiful water and natural beauty of Midnight Pass which is just to the north of this property and sandbar relaxation just a short boat ride away. This home features all the right spaces and updates- it features a smartly renovated main house comprised of three bedrooms, three and a half bathrooms and spacious office, as well as separate guest suite with full bathroom. From the moment you approach this property you can tell something is different about it. The large front yard features a wraparound drive with tasteful landscaping and as you approach the front door you are transported into true relaxation as you enter over a pool with footbridge to the front door. The immediate thing you will notice are unobstructed beautiful views, high ceilings and stunning architecture. As you take in the 36x36 tile updated flooring you’ll visit the kitchen and great room. The kitchen features upscale appliances from SubZero, Miele and Thermador, as well as sleek European style cabinetry. The main living space opens onto a screened, elevated patio with built-in summer kitchen. The primary is oversized with soaring ceilings and features a spa-like bathroom with free-standing tub, walk-in shower, dual vanities, and walk-in closet. The real fun begins outside- it’s hard to beat the outdoor living space- private sandy beach, heated pool and spa, and large fenced backyard to enjoy. The boating enthusiast will enjoy dual 16k and 10k boat lifts, fish cleaning station, water and electrical service. This home features its own video security system, solar panels with battery backup, a full complement of hurricane shutters, and is located in flood X, indicating no flood insurance required. The roof was replaced in 2025, the structure is built strong with ICF concrete block construction, and the attic insulation is spray foam for energy efficiency. This special estate must truly be seen in person to grasp- schedule your private showing today.

324 Bayshore Drive, Osprey
$650,000
2 Beds ⋅ 3 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code
This custom built home is located in the Osprey subdivision Bay Acres, west of the trail, in an established neighborhood along Little Sarasota Bay between Sarasota and Venice. This location allows easy access to I-75, top rated schools to include the magnet school Pine View , and Nokomis and Siesta Key Beaches, and all amenities of both cities. This home includes over 4000 sq ft of total space that includes a garage with over 1400 Sq. Ft. of space- part of the garage having a large open area previously used as a hobby room that can be converted to an area to meet your needs-possible extra car storage, boat storage, jet ski storage. The interior of the home has many nice features including a very nice large kitchen , dining room with tray ceilings, floors are gorgeous-real hardwood and wide planked. This well-built home has impact windows, a metal roof, a large covered porch and fenced yard. This small waterfront community will allow you to keep your Boat/Trailer or RV on your property. Property is in Flood Zone X. The Community Park of Bay Acres also has some boat slips upon availability and Kayak storage for a small fee. You can be out in Gulf waters through midnight pass in minutes. Around the corner is Blackburn Point Boat Ramp, and many waterfront restaurants. Looking for the perfect place to put down roots? Come see why this friendly neighborhood and home can make your dreams a reality. Easy to show

347 Bayshore Drive, Osprey
$640,000
Bay Acres Sub SubDv. ⋅ 34229 Zip Code
Exceptional Investment Opportunity – Profitable Remodeled Duplex in Prime Osprey Location! Updated in 2021 with a new roof, modern kitchens, contemporary appliances, stylish flooring, and upgraded electrical systems. This income-producing gem is currently generating $112,000 in gross annual short-term rental income, making it an unbeatable addition to your investment portfolio. Nestled on an oversized lot, the property is ideally positioned just a short walk from Little Sarasota Bay, only 1.8 miles from pristine Casey Key Beach, and a mere 5 miles from world-renowned Siesta Key, ensuring strong guest appeal and year-round rental demand. Each thoughtfully designed unit offers comfort, style, and functionality, creating an inviting retreat for guests or tenants. The duplex comes fully furnished and turnkey, perfect for immediate move-in or continuing as a lucrative short-term rental in a booming market. Residents enjoy the benefits of a voluntary community fee of just $75, providing access to a kayak launch for paid members. The community also boasts 12 dock slips, available on a first-come, first-served basis, adding to the allure of this unique waterfront lifestyle. This duplex represents more than just an investment—it’s your chance to own a piece of Florida’s coveted coastal lifestyle. Don’t miss this rare opportunity to secure a high-performing, income-generating property in one of the Gulf Coast’s most desirable communities. Contact us today to schedule your private showing and start enjoying the rewards of this exceptional property! Optional membership of $75.00 annually allows access to bay acres boat basin, park, kayak launch and picnic tables. First come first serve basis slips are $1,600 annually. There is a one time capital improvement fee for new boat slip lessees 50% of the annual rental fee. Max Boat length 22ft for the boat slips

6 Bay Acres Avenue, Osprey
$527,500
3 Beds ⋅ 3 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code
NEW PRICE • REAL OPPORTUNITY • SELLER READY. This is your chance to secure a West of the Trail pool home in the coveted Bay Acres community at an exceptional value. Welcome to Bay Acres—a quiet coastal enclave where classic Florida charm meets everyday livability. Positioned on a generous corner lot with a circular driveway, this 3-bedroom, 3-bath residence delivers space, privacy, and flexibility rarely found at this price point. Inside, the split floor plan is both functional and inviting, ideal for full-time living, hosting guests, or multigenerational needs. The heart of the home opens effortlessly through large double doors to an oversized screened pool retreat, creating that true indoor-outdoor lifestyle everyone wants but few homes actually deliver. Morning coffee, evening swims, weekend gatherings—this backyard was made for it. Each bedroom is thoughtfully placed for privacy, while the layout easily adapts to a home office, guest suite, or extended family living. The corner-lot setting enhances natural light, adds breathing room, and boosts curb appeal with mature Florida landscaping. Home was re-Plumbed 2 years ago. Bay Acres offers a rare West of the Trail lifestyle near the Intracoastal, with optional HOA membership providing access to the community dock—perfect for boating enthusiasts. You’re minutes to Nokomis Beach, Venice, Siesta Key, Pine View School, shopping, dining, and U.S. 41, making this location as practical as it is desirable. With a significant price improvement already in place, this home now represents one of the best opportunities in Bay Acres. Bring your vision, and make this coastal pool home your own.

315 Bayshore Drive, Osprey
$430,000
2 Beds ⋅ 1 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code
Welcome to this beautifully updated home on a half acre lot. Presenting a modern comfort in a county-like setting. Only 10 minutes from Siesta Key Beach, 8 minutes from Nokomis Beach, within a mile from a highly sought-after Pine View Elementary School, and close to shopping and dining! Inside you will find a fully remodeled interior featuring a custom kitchen with shaker cabinets, subway tile backsplash, and quartz countertops. You will also find new Samsung Bespoke appliances including a refrigerator, range, microwave, dishwasher, washer and dryer. High-end laminate flooring throughout, an updated bathroom with new tile, modern shower with a glass enclosure, and a custom vanity with a touch to illuminate mirror. Outside enjoy a 12x24 screened in lanai, a large yard for entertaining, gardening, or just room to relax. This property has generous parking with room for a RV, boat, and multiple additional vehicles, along with a 16x10 powered shed for storage, hobbies, or workshop.

328 E Bay Street, Osprey
$400,000
2 Beds ⋅ 2 Baths ⋅ Bay Acres Sub SubDv. ⋅ 34229 Zip Code
Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.

32 Bay Avenue, Osprey
$241,000
Bay Acres Sub SubDv. ⋅ 34229 Zip Code
One or more photo(s) has been virtually staged. Rare corner lot opportunity in the highly sought-after waterfront community of Bay Acres in Osprey. Zoned RSF-2, this oversized 0.32-acre homesite offers the flexibility to build a custom approximately 4,500 sq ft pool home or design a smaller primary residence with a detached guest cottage/ADU for guests, multigenerational living, or additional flexibility. Public water and sewer are available, and a private well is already in place for future irrigation. Survey available. Bay Acres is a hidden gem for boating and outdoor enthusiasts, offering optional HOA access to a private 12-slip marina, community boat ramp, paddleboard and kayak launch, with dockage available for qualifying vessels up to 22 feet. Surrounded by million-dollar homes and new luxury construction, this location blends lifestyle, boating access, and long-term value in one of Sarasota County’s most desirable coastal corridors. Ideally located near Nokomis Beach, Casey Key, Oscar Scherer State Park, Legacy Trail, Pine View School, Downtown Venice, and Downtown Sarasota’s dining, shopping, marinas, and arts scene. Walk the property, envision your future home, and experience why vacant land west of the Trail is becoming increasingly hard to find.

Sarabay Road, Osprey