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Osprey

One of the most popular communities provided by The Graf Group of Coldwell Banker

Osprey

About Osprey

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.

One of the most popular communities provided by The Graf Group of Coldwell Banker
154
# of Listings
3
Avg # of Bedrooms
$521
Avg. $ / Sq.Ft.
$1,239,814
Med. List Price

Browse Osprey Real Estate Listings

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$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

5 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

8,050 Sq.Ft.

$10,750,000

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

Price reduced
Directly fronting the turquoise waters of the Gulf, this newly remodeled Spanish Mediterranean estate on North Casey Key offers the rare luxury of your own private beach just steps from the home. Set along one of Florida’s most exclusive barrier islands, the property captures sweeping sunset views and exceptional privacy while remaining minutes from the dining, shopping, and cultural attractions of Venice and Sarasota. Behind a gated entry, the residence features three bedrooms and three-and-a-half baths, thoughtfully remodeled to highlight its Gulf-front setting. Expansive windows and sliding glass doors frame breathtaking water views and fill the interiors with natural light and coastal breezes. Architectural details include wood beams and moldings, Mexican tile and wood floors, brick accents, hand-painted stair tiles, and hurricane-impact windows and doors. Recent updates include a new roof, new pool, and updated A/C and pool equipment. The gourmet kitchen features custom cabinetry and Wolf appliances, ideal for entertaining after a day on the private beach. The primary suite offers a sitting room, wet bar, soaking tub, walk-in closet, and a private balcony overlooking the Gulf. Two en-suite guest bedrooms provide comfort and privacy for visitors. A spiral staircase leads to a rooftop deck with panoramic views of the Gulf and Intracoastal Waterway. Outside, the courtyard-style pool and tropical gardens create a serene retreat just steps from the shoreline. Experience the privacy, beauty, and unmatched lifestyle of Gulf-front living on Casey Key.
#A4667263

OSPREY

121 N CASEY KEY ROAD

4 Beds

5 Baths

4,096 Sq.Ft.

$6,475,000

MLS#: A4667263

One or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf through nearby Midnight Pass. Positioned along 100 feet of Little Sarasota Bay frontage, it includes a private dock and 15,000-lb boat lift. Inside, the residence provides over 6,300 square feet of living space, soaring ceilings, walls of windows, and sweeping bay views. Wide-plank oak and floor-to-ceiling hurricane-impact windows frame generous living spaces designed for entertaining and an open-plan gourmet kitchen. The primary suite includes a spa-inspired bath and spacious walk-in closets. Upstairs, three en suite bedrooms feature views over the bay; an additional room offers flexibility as a sitting room or fifth bedroom. Outside, a large travertine terrace, resort-style pool and hot tub, propane fire pit, and broad bayside lawn showcase Sarasota’s brilliant sunsets. A four-car attached garage and air-conditioned, detached three-car garage offer space for car collectors, or for an artist’s studio or home gym. Ideally located between Sarasota and Venice, the home has easy access to Siesta Key and Nokomis beaches as well as to the many cultural attractions of Sarasota’s downtown. Additionally, the home has a documented history of no flooding, water intrusion, or hurricane damage, providing significant peace of mind. This bayfront estate is a unique combination of lush acreage, secure elevation, boating access, and luxury coastal living—a complete waterfront lifestyle.
#A4672618

OSPREY

730 SARABAY ROAD

4 Beds

5 Baths

6,308 Sq.Ft.

$5,495,000

MLS#: A4672618

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

5,087 Sq.Ft.

$5,000,000

MLS#: A4664424

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