Osprey Property Search

Osprey, Florida Real Estate

Osprey is part of the extended Bradenton, Sarasota, Venice metropolitan area.  It is a peaceful, blissful, yet socially conscious town, offering areas of interest including the Historic Spanish Point made up of 30 acres, and including a museum and an environmental complex with a shell mound and a late 19th century pioneer homestead museum.

Find Homes for Sale in Osprey

Browse current listings for property for sale in Osprey below. Use our search widgets to dig deeper and find other real estate for sale in the area including homes, condos, land and waterfront property. 

Osprey Property Search

$6,500,000
5 Beds 3 Baths Casey Key SubDv. 34229 Zip Code
Rarely available Gulf to Bay estate size property with 175 feet of Gulf frontage, 175 feet of Bay frontage and encompassing 1.5 acres is located on the exclusive North End of Casey Key. Casey Key, distinguished for its absence of high-rises, traffic congestion, and private beaches, is one of the most esteemed barrier islands of Sarasota and Florida’s Gulf Coast. Positioned amidst exclusivity and privacy, this property presents a prime canvas for luxurious coastal living. Opportunity to build a spectacular new residence with no barriers to removing the current structure; or embrace “Old Florida” and restore the original house built in 1916. This building is the first and oldest structure built on Casey Key and was utilized as a “Fishing Lodge”. Uniquely the front of the house is oriented to Little Sarasota Bay because when it was built there were no bridges and the guests arrived and departed on boats from the mainland! Numerous infrastructure items have been completed facilitating a seamless progression for prospective owners. Most noteworthy is the successful approval and issuance of the permit by the State of Florida Department of Environmental Protection Agency to build west of the coastal construction line, which allows for a 6600+ square foot two-story single-family residence, a 1600+ square foot one-story detached accessory structure with bonus suite, swimming pool, and a reflecting pond at the entrance of the main residence. This is significant because the State EPA permit is the most difficult permit to obtain; also, the Sarasota County building permits are currently in process. The impressive new dock is constructed with premium composite decking and sturdy pilings, which accommodates various vessel sizes, including a 40,000-pound boat lift for vessels over 40 feet, a 17,000-pound lift for boats ranging from 25 to 37 feet, plus a double wave runner lift. Extending 162 feet into the bay, the dock offers power and water access throughout its length, alongside amenities like a fish cleaning station and other conveniences. Additionally, the newly drilled 4-inch and 400-foot-deep irrigation well assures that the estate grounds will be a lush and tropical environment. Embracing the island lifestyle, residents relish the warm Gulf breezes by day and breathtaking sunsets at dusk. A favorite transportation choice by residents is often Golf Carts with easy access to nearby tiki bars, restaurants, grocery store, pharmacy and more. The property's strategic location just north of the historic Blackburn Point bridge facilitates excellent proximity to the mainland with top-rated schools, fine dining establishments, Downtown Sarasota, St Armand’s Circle, The Island of Venice, and world-class medical facilities. Notably, Casey Key is the ONLY barrier island in the region with an expressway from Tamiami Trail to I75 creating easy access to all area international airports, plus private air travel options within ten minutes. The allure of this locale is undeniable, as Casey Key Road was recently acclaimed as the most impressive street nationwide, underscoring the unparalleled status of this magical barrier island.

608 N Casey Key Road, Osprey

$6,500,000
Casey Key SubDv. 34229 Zip Code
Rarely available Gulf to Bay estate size property with 175 feet of Gulf frontage, 175 feet of Bay frontage and encompassing 1.5 acres is located on the exclusive North End of Casey Key. Casey Key, distinguished for its absence of high-rises, traffic congestion, and private beaches, is one of the most esteemed barrier islands of Sarasota and Florida’s Gulf Coast. Positioned amidst exclusivity and privacy, this property presents a prime canvas for luxurious coastal living. Numerous infrastructure items have been completed facilitating a seamless progression for prospective owners. Most noteworthy is the successful approval and issuance of the permit by the State of Florida Department of Environmental Protection Agency to build west of the coastal construction line, which allows for a 6600+ square foot two-story single-family residence, a 1600+ square foot one-story detached accessory structure with bonus suite, swimming pool, and a reflecting pond at the entrance of the main residence. This is significant because the State EPA permit is the most difficult permit to obtain; also, the Sarasota County building permits are currently in process. The impressive new dock is constructed with premium composite decking and sturdy pilings, which accommodates various vessel sizes, including a 40,000-pound boat lift for vessels over 40 feet, a 17,000-pound lift for boats ranging from 25 to 37 feet, plus a double wave runner lift. Extending 162 feet into the bay, the dock offers power and water access throughout its length, alongside amenities like a fish cleaning station and other conveniences. Additionally, the newly drilled 4-inch and 400-foot-deep irrigation well assures that the estate grounds will be a lush and tropical environment. Embracing the island lifestyle, residents relish the warm Gulf breezes by day and breathtaking sunsets at dusk. A favorite transportation choice by residents is often Golf Carts with easy access to nearby tiki bars, restaurants, grocery store, pharmacy and more. The property's strategic location just north of the historic Blackburn Point bridge facilitates excellent proximity to the mainland with top-rated schools, fine dining establishments, Downtown Sarasota, St Armand’s Circle, The Island of Venice, and world-class medical facilities. Notably, Casey Key is the ONLY barrier island in the region with an expressway from Tamiami Trail to I75 creating easy access to all area international airports, plus private air travel options within ten minutes. The allure of this locale is undeniable, as Casey Key Road was recently acclaimed as the most impressive street nationwide, underscoring the unparalleled status of this magical barrier island. Please note the original house built in 1916, which is the first and oldest homestead built on Casey Key, is still on the property; however, there are no barriers to removing the structure.

608 N Casey Key Road, Osprey

$5,350,000
3 Beds 4.5 Baths Bay Acres Sub SubDv. 34229 Zip Code
Welcome to this exclusive 2024 waterfront estate by Pileggi Custom Homes—a boater's dream nestled on over half an acre with 116 feet of waterfront footage. This pinnacle of luxury offers showcase views of Little Sarasota Bay and Casey Key sunsets. Spanning over 2 floors, the home features 3 bedrooms, 4.5 bathrooms, an office, open floor plan and an exquisite outdoor area with a custom-built waterfall pool and fire pit. Enter through a grand 10-foot custom front door into the expansive living room area, featuring soaring 24-foot coffered ceilings. The gourmet kitchen is a culinary delight, showcasing custom cabinetry by Yoder Kitchen Corp, accented with stainless steel inlays and equipped with Bertazzoni appliances imported from Italy. A highlight of the kitchen is the central island, complemented by matching walnut wood grain pattern along the cabinetry and offering ample storage with upper and lower cabinets, including a stainless-steel inlaid China cabinet. The master bedroom suite is a sanctuary of elegance, featuring coffered ceilings and a generously sized walk-in closet. The ensuite master bath exudes luxury with custom walnut wood cabinetry, and a spacious walk-in shower with dual shower fixtures, including a handheld and body jets for a spa-like experience. The master bath is adorned with 24x36 large format tiles in the walk-in shower. Second and third bedrooms each feature ensuite spa-like bathrooms with walk-in showers and dual vanities. Second bedroom is further enhanced with tray ceilings, adding a sense of architectural detail. Italian tile floors in the second bathroom complement the overall elegant design of the home. Additional features include a high-end surround sound system, custom red oak staircase with LED lighting seamlessly connecting the first and second floors, solid core shaker style doors, recessed lighting and epoxy flooring on the first floor. Step onto the stunning pool area, perfect for enjoying mesmerizing sunsets over Little Sarasota Bay, complemented by a soothing hot tub. Enhance your evenings with fire bowls and columns, casting a warm glow against the backdrop of panoramic views. A custom fountain with mesmerizing LED laser lights adds to the ambiance, while an accessible full bath ensures convenience for guests. Seamlessly integrated with a wireless security and surround sound system, this outdoor retreat epitomizes coastal elegance and comfort. Enjoy direct access to the Bay from the estate's brand new dock with water and electric and 20,000 lbs boat lift. The dock features a water depth ranging from 1 to 7 feet at the bulkhead seawall, making it suitable for various watercraft activities with unobstructed high impact showcase views. Additionally, this home is constructed with poured concrete and insulated foam, maintaining temperatures significantly cooler than outside averages. Also, to ensure peace of mind, this property features hurricane-impact vinyl windows. The home is elevated over 13 ft with no flood insurance requirement. An expansive 5-car garage, featuring 14-foot ceilings and epoxy flooring is attached. The home features a 1,000 gallon propane tank & generator. Just minutes to Casey Key and prized Siesta Key beach. Proximity to the A+rated Pine View school. Easy access to US 41 for plentiful shopping, dining, & entertainment spots in downtown Sarasota and Venice. This meticulously designed brand-new home offers unparalleled elegance for the exclusive waterfront lifestyle.

614 Bayshore Drive, Osprey

$4,250,000
4 Beds 4 Baths Sorrento Shores SubDv. 34229 Zip Code
Nestled in the serene and highly sought-after Sorrento Shores community, this exceptional and breathtaking property offers unparalleled waterfront living on over an acre of land (1.19 acres) along the tranquil South Creek. Featuring 144 feet of water frontage, the home is tucked away on a secluded drive, providing both privacy and stunning water views. <br> <br> Completely renovated inside and out, this home boasts numerous modern upgrades, including three new TRANE A/C units (2020), a commercial-grade Kohler gas generator, a new metal roof, hurricane impact windows and doors, and an expansive concrete driveway. Two custom-built garages offer ample storage and versatile space—one, a 36x36 garage, includes over 1,100 sq ft of living area, perfect for an in-law suite, home gym, studio or hobby space, complete with a full bathroom and a separate A/C storage closet below. The second garage (30x40) is insulated and ideal for storing your recreational toys or having it be your work shop. <br> <br> Inside, the home is a masterpiece of design, featuring tile flooring throughout, custom trim, solid core doors, and luxurious bathrooms. The chef’s kitchen is equipped with white shaker soft-close cabinets, stainless steel appliances, custom countertops, and a spacious eat-in island. A floating open curved stairway leads to the second level, where two guest bedrooms and a secondary primary suite await. Enjoy the breathtaking water views from the second story with wall to ceiling windows and the overhang deck through the walk out slider doors. There is also a large walk-in closet with custom cabinets, and the spa-like bathroom with a freestanding bathtub and walk in shower. <br> <br> Architecturally unique, this home features curved brick walls, loft areas, two-story ceilings, and two fireplaces, adding character and charm. The two primary suites each offer walk-in closets and en-suite bathrooms, while modern touches like recessed lighting, custom ceiling fans, remote-controlled blinds, and 1x6 base trim ensure every detail is carefully considered. <br> <br> Outside, enjoy a large, heated saltwater pool with an outdoor shower, perfectly positioned to capture the sun all day. The lush, manicured lawn extends to the water, and a large dock equipped with water, electricity, and a new 13,000 lb Neptune boat lift makes boating a breeze. Additional outdoor features include soffit and solar lighting, privacy fencing, custom aluminum railings, composite decking, and multiple paver areas and walkways. Additional buried propane tank for the commercial sized Generator. <br> <br> This one-of-a-kind property offers luxury, privacy, and the ultimate Florida lifestyle—don’t miss the opportunity to make it yours!

412 Cezanne Drive, Osprey

$3,995,000
4 Beds 5.5 Baths The Oaks SubDv. 34229 Zip Code
**EXQUISITELY DESIGNED ESTATE BOASTS MODERN & CONTEMPORARY ELEGANCE** This FULLY UPDATED Residence features a MAIN HOUSE with 3Beds/4.5Baths plus GUEST HOUSE (1Bed/1Bath, Kitchen/Laundry, Living area) and is situated on an Oversized, Private and Serene DOUBLE LOT in the SECURE, OAKS BAYSIDE Country Club Neighborhood on Little Sarasota Bay. Finishes of the highest quality abound and include Custom Iron entry and interior doors, Italian Murano sconces and chandeliers, architectural recessed lighting, Marble and Porcelain Flooring, Iron and Glass custom Wine Cellar, Glass enclosed “Spirits” Showcase, luxury appointments and fixtures throughout and is a MUST SEE! The GOURMET KITCHEN is impressively equipped with top brands including SUBZERO, WOLF, 2 ASKO dishwashers, “Waterstone” gantry faucets, work-station sinks, custom range hood, MIELE Coffee Station, etc. In total, there are 2 kitchens and 3 laundry facilities. The Stunning OUTDOOR ENTERTAINING area features a spacious screened lanai with Gorgeous, Saltwater, Heated, Pebbletec 64ft Lap Pool and Spa, Marble deck, OUTDOOR KITCHEN with Twin Eagles Grill, 2 refrigerators, covered gathering area with fireplace, air-conditioned Pool Bath with Aromatherapy Steam Shower (New in 2024), storage room and Additional Open Air Patio with FIRE PIT. Extensive Home Automation (Control4: sound, lighting, etc.) and Mechanical system installations were thoughtfully executed and include a Generator, water treatment and purification systems, robust Wi-Fi throughout, Vivent video monitored security system, Air-Conditioned Garage with EV charging, resin coated floors and utility sink, etc. Impressive grounds with new landscaping, hardscaping & lighting. Newer ROOF, HVAC, Hurricane Impact Rated Windows and Doors. THE OAKS-BAYSIDE is a distinguished, 24hr Guarded, 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, wonderful CROQUET facility, 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 there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

601 Fernwalk Lane, Osprey

$3,990,000
4 Beds 3.5 Baths Casey Key SubDv. 34229 Zip Code
This mid-century modern luxury property includes approximately 100' of water frontage on the Gulf of Mexico with stunning unobstructed views and over half of an acre lot. Relax in the sun on the patio or take in the gorgeous sunsets from almost every room. This Gulf front beach home is located on one of the most serene and exclusive barrier islands on Florida's west coast. As you walk through the home, you'll love the open living area with large ceramic tiles throughout, vaulted exposed beam ceilings, fireplace and dining room that adjoins the beautiful kitchen. The kitchen features lovely quartz countertops and stainless appliances. The beach carries indoors with the charm and character of local beach shells crushed and floated in natural cement to create textured walls that brings the outside indoors. Listen to the waves as you fall asleep in your upper level primary suite with gorgeous water views and maximum privacy for both owners and guests. The peaceful bedrooms also include a second primary suite on the first floor. The gated entry onto the property brings you into complete privacy and seclusion with lush landscaping and large shade trees. Enjoy sitting in the shade of the magnificent live oak around the fountain on your over 1/2 acre lot. Take a walk or drive your golf cart to the famous Casey Key Fish House and Deep Lagoon upscale restaurant and marina, only a half mile to the supermarket, and a quick drive to all of the wonderful shops and restaurants Sarasota and Venice has to offer. Easy access to the mainland and I-75 via the iconic Blackburn Point Bridge nearby.

5 N Casey Key Road, Osprey

$3,350,000
5 Beds 6.5 Baths Oaks SubDv. 34229 Zip Code
Welcome to a sanctuary of elegance and comfort at 497 Webb's Cove, in The Oaks Country Club. This exceptional property blends sophistication and warmth, making it a true gem in Sarasota County, just a short drive from the renowned Siesta Key Beach. Situated in The Oaks, this updated residence showcases exquisite craftsmanship and meticulous attention to detail. From the inviting living spaces to the beautifully landscaped surroundings, every aspect of this home is designed to impress. You'll be greeted by landscaped grounds and lighting, complemented by a new irrigation system. Step into the grand entryway, featuring refinished stairs, tiled risers, custom hand-carved finials, moldings, and a striking chandelier. The formal living room boasts double doors, a retiled fireplace with a custom mantel, added lighting, and professionally hung wallpaper. The dining room features a showcase window, custom molding, double chandeliers, and exquisite wallpaper. The bourbon room includes exterior double doors, a squirrel cage fan, custom shelving, mirror tiles, custom beams, a painted cabinet, new fireplace tile, and a custom mantel with TV hookup. The wine closet features a cooling unit, moisture barrier insulation, redwood racks, an exterior door with a combination lock, and rope lighting. Downstairs, the guest bath has extra lighting and a new faucet. The kitchen is a chef's dream with French doors, a second island, glass pantry doors, a pot filler, Versace backsplash and wallpaper, additional lighting, a demoed wall creating a family room, and a second pantry. The family room has wood flooring and extra lighting. The guest house, converted from a 2/2 to a 1/1, now offers a more open floor plan and wood flooring, making space for the expanded family room. Outside, new lighting, landscape lighting, replaced pool tile, and an upgraded pool screen enhance the backyard oasis. Upstairs, laminate flooring and new lighting have been installed throughout. The movie theater features a blocked window, extra AC vents, a built step-up, surround sound, a concession stand, and Joy movie theater carpet. The primary bedroom is adorned with Vant panels and extra lighting. The gym has cork flooring and demoed closets, while the primary bathroom includes extra lighting and new skylights. The speakeasy has a custom wood ceiling, brick wall panels, a hidden brick door, new stairs, added lighting, and laminate flooring. The speakeasy bathroom is equally impressive with new tile, a painted cabinet, faucet, mirror, and extra lighting. Additional features include professional painting throughout, new water heaters, new garage openers, spray insulation, a speakeasy with two ducted ventilation systems, deep-cleaned and sealed tile, a home fragrance system, a shell-placed backyard, custom beams, and additional vents in the primary bath. Boasting 5 bedrooms, 6.5 bathrooms, and luxurious amenities, including a movie theater, guest house, bourbon room, speakeasy, outdoor kitchen, and home gym, 497 Webb's Cove is a luxurious retreat perfect for families and individuals. Experience the best of coastal living with access to world-class amenities, pristine golf courses, a vibrant community, and Siesta Key Beach. Make 497 Webb's Cove your new home and indulge in the epitome of Florida living at The Oaks Club. Schedule a viewing today and step into a lifestyle defined by comfort, elegance, and unparalleled beauty.

497 Webbs Cove, Osprey

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