View All Latest Osprey/Nokomis 7500+ Sq. Ft. Properties for Sale

4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Virtually Staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the lanai, where golf course views frame the heated pool, spa, and outdoor kitchen. The first-floor primary suite is a true retreat, featuring high ceilings, multiple closets, and a flexible sitting area that can serve as a nursery, gym, or private office. Upstairs, guests enjoy their own wing complete with a loft, theater, and screened terrace—ideal for relaxing or hosting in style. A split four-car garage, custom finishes, and generous room throughout reflect the craftsmanship expected in one of Sarasota’s most distinguished country club communities. The Oaks offers 24-hour security, two championship golf courses, an acclaimed racquets program, fitness and wellness facilities, and fine dining—all just minutes from the beaches and top-rated schools. Experience this home for yourself—take the 3D virtual tour and book your private showing today.

854 Macewen Drive, Osprey

$9,000,000

6 Beds ⋅ 7 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

WELCOME TO ONE OF THE FEW BRAND-NEW GULF FRONT HOMES FOR SALE ON THE WEST CENTRAL COAST OF FLORIDA. A rare opportunity, where cutting-edge design meets wide Gulf vistas. Nestled on the prestigious barrier island of Casey Key, this newly constructed Modern Coastal estate exemplifies modern beachfront living. Positioned directly on the sand with sweeping Gulf views, this striking residence offers elevated living space, showcasing the pinnacle of craftsmanship and architectural innovation. Built with block construction, pilings, impact-rated windows and doors, and a four-stop elevator, every detail of this home has been thoughtfully curated for style, function, and resilience. Inside, soaring 24-foot ceilings welcome you into the grand foyer and great room, anchored by a dramatic floating staircase and a 24-foot feature fireplace wall. With en-suite bedrooms, state-of-the-art home theater, lounge, bar, and a wine wall, this home offers both grand entertaining and serene retreat. The chef’s kitchen is a design showpiece, featuring European cabinetry, dual waterfall-edge islands clad in book-matched 3cm quartz, and premium Sub-Zero & Wolf appliances. Dual laundry rooms, breakfast nook, and custom built-in vanities provide elevated everyday living. The primary suite is a personal sanctuary, complete with a spa-like bathroom featuring a 71-inch freestanding tub, dual rainfall showers, a makeup vanity, and a large walk-in closet. Every bathroom throughout the home is appointed with bespoke cabinetry, quartz surfaces, and backlit mirrors. Designed to impress from every angle, the home is finished with smooth stucco, level 5 drywall, hardwood floors, imported tile, and integrated LED tray ceilings. A sleek rooftop terrace crowns the home, offering panoramic views of the Gulf and beyond. Step outside to your personal resort: an expansive terrace with an oceanfront pool, floating spa, sun decks, outdoor fireplace, and fully equipped kitchen. Lush, tropical landscaping, Zoysia grass, and a concrete drive with turf inlays complete the impeccable exterior design. Sleek metal railings accentuate balconies and the rooftop for a modern edge. Set on a half-acre of prime waterfront. This is coastal modern luxury at its pinnacle—a rare opportunity to own a brand-new, Gulf-front estate on one of Sarasota’s most desirable stretches of sand.

4005 Casey Key Road, Nokomis

$2,925,000

4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Sited at the end of a quiet cul-de-sac behind the gates of the prestigious Oaks Clubside in Osprey, Florida, this stately traditional custom estate offers refined living in one of Sarasota County’s most exclusive communities. Perfectly positioned on over three-quarters of an acre, the residence boasts serene preserve and fairway views, capturing the essence of Florida luxury living. Inside, discover graciously sized rooms, soaring ceilings, and abundant natural light that fills every space. The formal living room with gas fireplace and the formal dining room provide elegant spaces for entertaining. The open-concept kitchen and family room are the heart of the home, ideal for casual gatherings and everyday comfort. A large kitchen offers a generous walk-in pantry, plentiful storage, and a seamless flow into the family room and outdoor spaces. The primary suite is located on the main floor, offering a tranquil retreat with a spa-like bathroom, separate dressing room, and expansive walk-in closet. An office with fireplace is also on the main level, perfect for work-from-home privacy. Upstairs, two additional bedrooms and a bonus room provide a private haven for guests or multi-generational living. Step outside to the screened and covered outdoor living area, where a summer kitchen, cabana with full bath, and lush landscaping invite indoor-outdoor living year-round. It’s an entertainer’s dream, ideal for both intimate gatherings and grand events. Key features include wind-rated impact windows, new tile roof to be installed with a transferable 20-year workmanship warranty, $800,000+ in updates under current ownership, and situated on an oversized lot with ultimate privacy. As part of The Oaks Club, enjoy world-class amenities including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art WellFit Center, and exceptional dining at The Oaks Room, The Overlook, and The Tavern. This is more than a home—it's a lifestyle. Experience the timeless elegance, thoughtful design, and unmatched amenities of The Oaks Club in this remarkable estate.

550 Dove Pointe, Osprey

$2,315,000

4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Premier Waterfront Opportunity in The Oaks Bayside This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring ceilings, and dramatic architectural features, this residence was built to impress—and now invites a new owner to make it their own. The ground floor has been thoughtfully prepared for renovation, providing a blank canvas to bring your vision to life. Whether you imagine a guest or in-law suite, a luxury garage with a gaming lounge, a showcase for your fishing gear, or a green room for potting plants—the possibilities are endless. A private dock awaits your custom design, offering direct access to the open bay and Gulf of Mexico. Just steps from the home, the community dock—exclusively for Oaks Bayside residents—adds even more coastal charm. Fish, launch a kayak, relax and watch the sunset, or gather with neighbors in this serene waterfront setting. Ownership includes mandatory membership in The Oaks Club, unlocking an array of world-class amenities. Set across more than 1,000 acres, the club features two private 18-hole championship golf courses, 14 Har-Tru tennis courts, a croquet lawn, a junior Olympic swimming pool, state-of-the-art fitness center, and a stunning 34,000-square-foot Georgian-style clubhouse. A guest lodge and vibrant year-round social calendar complete this private country club experience. You're not just creating a home—you're curating a luxury lifestyle in one of Florida’s most prestigious coastal communities. This exceptional property is ready for your private tour at your convenience.

112 Osprey Point Drive, Osprey

$8,631,000

Acreage & Unrec SubDv. ⋅ 34275 Zip Code

Escape Resort and Marina is a rare opportunity to purchase a profitable boutique resort that exudes a tropical sophistication that is rarely found. This tropical oasis is comprised of seven buildings with enormous suites that have very recently been thoughtfully reconstructed. This Casey Key resort is located on over one acre of lushly landscaped waterfront paradise that is only steps from the pristine sand and welcoming waves of the Gulf of Mexico and located near delicious waterfront restaurants and world class shopping. The lushly landscaped paver walkways lead to 14 expansive rooms each open onto the outdoor patios & balconies with many rooms having a waterfront view. All recently reconstructed rooms have been extensively renovated with features that include all new roofs, electrical and plumbing, HVAC and mechanical systems, new drywall with wall to ceiling finishes, new flooring throughout, new category 4 windows and doors and light fixtures. Each room offers new full-sized kitchens with high quality cabinetry, countertops and stainless-steel appliances, flat top stoves, microwaves, and dishwashers. Rooms range from 2 bedroom with den/3 baths to large one-bedroom suites. Onsite, guests enjoy a large pool and sundeck, hip, fun common areas including a beautiful waterfront clubhouse with full kitchen, a waterfront amphitheater with firepit, BBQ grilling areas, bicycle and kayak rentals, and workout facilities. The enormous modern rooms are styled to perfection and adorned with flat-screen TV’s, free Wi-Fi, and high-end furnishings. The attention to detail is awe inspiring as represented by the high guest review ratings and return clientele. This is a very profitable resort that has consistently experienced year after year increases in occupancy/ADR with very strong projections for 2024. The recently reconstructed 15 dock marina provides an additional generous steady stream of income. The marina is located on sailboat water and can accommodate boats up to 50 feet, contains up to 50-amp electric, water, nine 20-foot finger pipers as well as one covered boat slip with lift. Escape Resort is truly a premier year-round waterfront resort and marina. The demand for waterfront island Vacation Rentals is extraordinary and this resort stays consistently full. Escape Resort and Marina is located on coveted Casey Key Island nestled just south of world-renowned Siesta Key and quaint Venice Island and is a short drive into Sarasota, the cultural capital of the south. This island has very little accommodation competition and rooms can be rented nightly, weekly, or monthly. This Florida island beach lifestyle includes awe-inspiring sunsets and guests enjoy this amazing experience. With all of the upgrades recently completed, this is a turn-key investment for any entrepreneur or experienced hotelier that will bring tremendous cash flow while enjoying a true Island beach experience. Please DO NOT walk the property without permission and DO NOT disturb Seller or Employees.

212 Casey Key Road, Nokomis

$9,036,500

6 Beds ⋅ 7 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Auction Property. AUCTION PROPERTY: BID AUGUST 17-23. Previously listed for $18M. No Reserve. Showings every day through Tuesday August 22 from 1-4pm, Wednesday August 23 from 11-2pm & by appointment. Gulf-front paradise has never been sweeter than from exclusive Casey Key. A truly perfect location on 149±feet of pristine sandy walking beach meets its match with the six-bedroom estate of 2305 Casey Key Road. Inspire awe from the first look at the soaring architecture of the entry, where floor-to-ceiling, 12-inch windows and ornate double staircases frame dazzling views of the Gulf of Mexico. Both comfort and luxury are paramount here, with a careful balance between formal and casual entertaining spaces that welcome gatherings from intimate to grand. Gather for family brunch in the deluxe kitchen against a backdrop of Gulf views, or host a gourmet meal in the sumptuous octagonal formal dining room. Outdoors, treasures like the beachfront heated saltwater pool with heated spa and expansive sunset terrace promise a seamless experience no matter the venue. A deeded bayfront dock with 24,000-lb. lift ensures this estate’s splendor stretches beyond the private beach to the Gulf itself.

2305 Casey Key Road, Nokomis

$2,700,000

4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

**SPACIOUS, LUXURIOUS and BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE** Boasts OVER 9,000sf and is situated on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths + Office/Library + Home Theater + Game Room w/ Wet Bar, Loft, Balcony, etc. and even includes highly coveted, oversized and split 4-Car Garage(s). This MOVE-IN READY home has been tastefully updated and is ideal for indoor and outdoor entertaining! The elegant first level primary bedroom suite features high ceilings, multiple walk-in closets, garden tub, large custom walk-in shower and an adjacent nursery/fitness/den area. The sprawling, gourmet kitchen entails a generous island and counter seating area, premium stainless steel appliances, granite counters, solid wood cabinets, walk-in pantry and more. The upstairs loft leads to two vast bedroom suites, theater room and screened terrace/balcony. Enjoy the utmost in Florida outdoor living with a Heated Pool & Spa with Fire features and a large screened lanai with Outdoor Kitchen and seating areas while overlooking the serene interior, Heron Golf Course. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid tennis courts, 4 Pickleball Courts, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and available. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

854 Macewen Drive, Osprey

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