Sarasota's Premier Homes
One of the most popular communities provided by {{page_data.agentName}}

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
146
# of Listings
3
Avg # of Bedrooms
$404
Avg. $ / Sq.Ft.
$981,910
Med. List Price

Browse Osprey Real Estate Listings

All listings

Under $250,000

$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

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

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.

$6,790,000

MLS#: A4660004

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.
#A4657777

OSPREY

622 BAYSHORE DRIVE

6 Beds

5 Baths

6,627 Sq.Ft.

$5,700,000

MLS#: A4657777

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

Buyers resources
7 Reasons to Work with a Realtor
7 Principles For Home Buying Success
Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
Questions When Buying a Condo
Questions When Choosing a Realtor
Sellers resources
8 reasons to work with a realtor
Calculating Capital Gains
Checklist for Better Showing
Cleaning Home For Sale
Improving Odds Of an Offer
Preparing Home for photoshoot
Selling Your Home for More $$

properties found. properties found. Page of .

- property

Send a message

Message successfully sent.

Your message

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to receive some additional information on this specific property or similar properties?

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here