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Osprey

One of the most popular communities provided by Michael Graf

Osprey

About Osprey

<p>Osprey is a tranquil coastal community tucked between Sarasota and Venice, offering a perfect blend of natural beauty and upscale living. Known for its peaceful vibe, top-rated schools, and access to the Intracoastal Waterway, Osprey is ideal for nature lovers and boaters. Residents enjoy quick access to parks like Oscar Scherer State Park, waterfront dining, and nearby beaches. With elegant neighborhoods, quiet streets, and a strong sense of community, Osprey is a hidden gem on Florida’s Gulf Coast.</p>
One of the most popular communities provided by Michael Graf
140
# of Listings
3
Avg # of Bedrooms
$420
Avg. $ / Sq.Ft.
$955,580
Med. List Price

Browse Osprey Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

6 Properties Found. Page 1 of 1.

This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family and guests, this is a residence that inspire togetherness and embodies the art of waterfront living. Crafted with luxury finishes and modern conveniences, the property is built to exacting coastal standards with dramatic focus on stunning water views. Formal and casual spaces unite elegantly, including the living room with cypress beamed ceilings, overlooking the bay. A deluxe kitchen, wine, butler’s pantry and wet bar provide a canvas for culinary exploration and entertaining elegance. A grand media room for screening films provides the ideal place to unite music and culture. The expansive primary bedroom features a sitting room, lavish bath, dual closets, a breakfast nook and expansive views over the water. Three additional bedroom suites provide privacy, views and spacious accommodations. The fifth bedroom suite is equipped for a home gym, steam room and sauna. The office and library, next to the grand marble staircase, features leaded glass doors, hand crafted, built-in shelving, a coffered ceiling and beautiful views of the Gulf. Additional space for recreation and relaxation has been accomplished to make use of every inch of the estate. Arched hallways and French doors line the living room, open to the dazzling outdoor spaces and stone terraces lead to the infinity pool. Elevator access and garages for six vehicles add ultimate convenience. Enjoy boating from the deep-water dock which features a rare and grandfathered-in covered boat lift. North Casey Key is a haven of exclusivity and serenity, minutes from shopping, world-class golf, tennis and dining.
#A4643654

OSPREY

1216 N CASEY KEY ROAD

5 Beds

6 Baths

15,522 Sq.Ft.

$11,750,000

MLS#: A4643654

Property Type: Commercial Land with Existing Office Building Property Size: 10 Acres Discover this exceptional opportunity with over 900 feet of frontage on Tamiami Trail/US41 in Osprey, FL! This is one of the last substantial parcels available in Sarasota County with a Tamiami address. Positioned directly in the path of progress, this 10-acre parcel is ready for development with all entitlements in place. Property Features: Existing Office Building: 4,000 SF Freestanding Office Building with water, sewer, and electricity Development Potential: Density for Assisted Living Facility/Memory Care at 9 units to an acre Office Space Allowable: Up to 46,000 SF of office space Prime Location: Directly across from the new Publix and adjacent to massive new developments, including shopping plazas, restaurants, apartments/condos, and single-family homes Infrastructure: Electric, water, and sewer in place, making the property shovel-ready Accessibility: Easy access to Tamiami Trail from both ends of the property with simple median cuts at Southbay Drive/Luminary Blvd Strategic Positioning: Located at the northeast side of the intersection of Luminary Blvd and Tamiami Trail in Osprey, FL
#A4616676

OSPREY

505 LUMINARY BOULEVARD

None Beds

None Baths

4,000 Sq.Ft.

$7,499,000

MLS#: A4616676

Newly Remodeled Gulf-Front Mediterranean Villa on Casey Key Framed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastline. Just minutes from the cultural and dining destinations of Venice and Sarasota, the residence offers unrivaled privacy, architectural beauty, and Gulf Coast living beyond compare. Behind a gated entry, the main residence features three bedrooms and three-and-a-half baths, thoughtfully remodeled with no detail spared. Distinctive design elements include wood beams and moldings, Mexican tile and wood floors, brick accents, hand-painted stair tiles, and hurricane-impact windows and doors. Additional enhancements include a new roof, new pool, and updated A/C and pool equipment, ensuring comfort and peace of mind. The gourmet kitchen showcases custom cabinetry, Wolf appliances, and elegant finishes — ideal for entertaining or everyday living. Expansive windows and sliding glass doors bathe the interiors in natural light and frame breathtaking Gulf views. The master suite serves as a private sanctuary featuring a sitting room, wet bar, soaking tub, dual sinks, walk-in closet, and balcony overlooking the pool. Two en suite guest bedrooms provide comfort and privacy for family or visitors. A spiral staircase leads to a rooftop deck offering panoramic Gulf and bay vistas. Reflecting the romance of classic Spanish design, the home radiates warmth and character with arched doorways, pecky cypress ceilings, wrought-iron detailing, and timeless brickwork — blending old-world craftsmanship with modern luxury. The courtyard-style pool area and lush tropical gardens with winding walkways provide a serene setting for outdoor living and entertaining, while the guest quarters above the garage — complete with a full bath — can be used as an art studio, office, or fitness room. Experience the serenity, seclusion, and sophistication of Casey Key — a rare Gulf Coast haven where architectural elegance meets the natural beauty of Florida’s most celebrated barrier island.
#A4667263

OSPREY

121 N CASEY KEY ROAD

4 Beds

5 Baths

6,906 Sq.Ft.

$7,100,000

MLS#: A4667263

A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal with a 100-foot dock (built in 2019), dual 12,000-pound lifts, water, and electric, this property is an ideal destination for boating enthusiasts. Offered fully furnished upon request. The front elevation is framed by a raised lawn with a stone wall, a paver driveway and manicured landscaping. As you approach the home, the travertine steps lead you to the new custom front door, where dramatic water views of the bay immediately greet you through expansive windows on opposite side of the home, creating a seamless connection to the Gulf and Bay. Inside, the main level is anchored by a breathtaking great room with coffered ceilings, custom millwork, and a wall of windows and doors that open to the terrace, creating an indoor/outdoor living space. A two-sided fireplace adds warmth and ambiance to the great room and the adjacent terrace. The interior showcases a multitude of upgrades, including updated Palecek lighting, and new porcelain tile flooring throughout. The 2020-renovated gourmet kitchen showcases bay views, Cambria Skara Brae quartz countertops, subway tile backsplash, custom white cabinetry and premium stainless-steel appliances. A bar area includes a wine refrigerator and ice maker, while a built-in pantry corridor connects seamlessly to the dining room. The dining area features built-in cabinetry and enjoys stunning bay views from the terrace. The formal living room, with its tranquil blue and cream tones, provides a lovely space to enjoy Gulf views while welcoming guests for dinner. The home offers two spacious primary suites, each with walk-in closets and luxurious en-suite baths, offering serene bay views and access to their private travertine terrace. Two guest suites and an upstairs office also enjoy remarkable water views. The staircase to the upper level reveals an oversized picture window framing the Gulf views. A three-floor elevator provides convenient access to all levels. The ground level features a spacious three-car garage with a dedicated golf cart space. Abundant space is designed to accommodate a variety of uses, and a new glass custom door offers light and access to the backyard and patio. Impact-rated windows and doors, along with a whole-house generator, provide peace of mind. Outside, the resort-style backyard features a refinished pool (with new tile and resurfacing), lush tropical landscaping, an expanded travertine patio and tiered terraces with custom stonework, columns, and stone floors. A rooftop deck offers panoramic views of the Gulf and Bay. Water enthusiasts will appreciate seamless access to the Intracoastal and Gulf, ideal for effortless boating. Additional upgrades include a newly painted roof tile, full exterior and interior repainting (2023), new fencing for added privacy, and two new entry doors (2025), completing the home’s thoughtful transformation. 144 N. Casey Key Road presents a rare opportunity to own a private waterfront estate offering luxury, seclusion and convenient access to Sarasota’s shopping, dining, beaches and parks.
#A4660004

OSPREY

144 N CASEY KEY ROAD

4 Beds

5 Baths

10,722 Sq.Ft.

$5,990,000

MLS#: A4660004

Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand-new custom estate captures the essence of coastal luxury. From the moment you arrive, you are greeted by sweeping water views and spectacular Casey Key sunsets, setting the stage for an extraordinary lifestyle. Designed for the boating connoisseur, the property boasts a new dock with water, electric, a 20,000 lb boat lift, and direct bay access—no bridges to the Gulf. For the automotive enthusiast, a 1,400 sq. ft. climate-controlled garage with 14-ft ceilings, professional-grade car lifts, epoxy floors, perfect showcase for your collection. Inside, the home flows across two levels with 3 ensuite bedrooms, 4.5 baths, an office, and a dramatic 24-ft coffered ceiling living room. The chef’s kitchen is an entertainer’s dream, featuring two massive islands, bespoke Yoder cabinetry with stainless steel inlays, and Bertazzoni appliances imported from Italy. The primary suite is a private retreat with a spa-inspired bath, custom walnut cabinetry, dual shower with body jets, and a grand walk-in closet. Each guest suite offers its own spa-like bath. Constructed with poured concrete walls coated in Styrofoam and stucco for superior soundproofing, this residence offers both durability and comfort. Additional features include two central A/C systems, top-of-the-line sound and camera security, hurricane-resistant 14-ft ASL garage door, computerized pool controls, custom floors, bar area, 1,000-gallon LP tank, and UV-protected screens. Outdoor living is nothing short of exceptional, a custom waterfall pool (oriented east–west for optimal sun), spa, fire bowls, LED-lit fountain, and a full pool bath create the ultimate entertaining environment with an unforgettable bayfront backdrop. The new fenced and paved driveway ensures privacy and curb appeal, while the turnkey condition makes it move-in ready. Located just minutes from Casey Key, Siesta Key Beach, and the A+ rated Pine View School, this estate is more than a home, it’s a statement of refined living, where boating, entertaining, and coastal elegance converge.
#A4662210

OSPREY

614 BAYSHORE DRIVE

3 Beds

4 Baths

6,347 Sq.Ft.

$5,500,000

MLS#: A4662210

A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double-door entrance. Inside, the foyer sets the tone with soaring ceilings, hand-crafted moldings, chandeliers, and a white onyx floor with marble inserts. Spaces include an oversized living room with dual fireplaces, a crystal chandelier, and multiple sets of French doors opening to the lakefront patio. The dining room, anchored by another fireplace and framed by custom casings and built-in shelving, is ideal for grand entertaining. A domed ceiling sitting room with French doors to the patio adds an intimate space for cocktails or conversation, while the custom bar and wine room, with etched glass cabinetry, stone counters, and display shelving, enhances the home’s appeal for gatherings. The kitchen, completely remodeled in 2019, is a showcase of craftsmanship with UltraKraft® cabinetry, custom soffit lighting, Corian countertops, and a center island with breakfast bar. Luxury appliances include a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, microwave, warming drawer, two KitchenAid dishwashers, and a Frigidaire wine fridge. A butler’s pantry provides additional storage, while the sunny breakfast nook overlooks lush gardens. Family and gathering rooms carry the same sense of scale, with dramatic fireplaces, intricate moldings, and detailed ceiling treatments that flow seamlessly for everyday living or large-scale entertaining. The primary suite is a true retreat with a spacious sitting area, custom closets, and a well-appointed bathroom that was newly remodeled in 2025 with spa-inspired finishes. Three guest suites, each with updated full baths (2021 and 2025), provide privacy and comfort. One is a suite with a bathroom near the laundry room, which offers flexibility for live-in staff or extra accommodation. Outdoors, the home embraces its setting with an open pool, expansive deck, and cabana surrounded by manicured hedges and mature landscaping. The views are equally compelling, with mature gardens and community reflecting pond in the front and sweeping lake vistas in the back. Additional highlights include a three-car garage, refinished hardwood floors (2020), and a new Daikin 5-ton AC system installed in 2022. Ownership at The Oaks Club brings an unmatched lifestyle, with two championship golf courses, tennis and pickleball courts, croquet, a fitness center and spa, three on-site restaurants, and a community dock on Little Sarasota Bay. Elegant yet inviting, 101 Osprey Point Drive stands as a rare opportunity to enjoy lakefront living with resort-style amenities in one of Sarasota’s most established private enclaves.
#A4664424

OSPREY

101 OSPREY POINT DRIVE

4 Beds

5 Baths

6,841 Sq.Ft.

$5,000,000

MLS#: A4664424

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