Homes For Sale in Osprey 34229 - 145 homes

Remarks: Perfectly positioned on the 9th hole tee box within the Oaks community, this meticulously appointed estate offers a rare opportunity for a premier Sarasota golf course lifestyle. Designed for the discerning enthusiast, the property features panoramic fairway views and western exposure for breathtaking sunsets. The interior is defined by soaring vaulted ceilings, refined crown molding, & finishes throughout. The heart of the home is a curated chef’s kitchen featuring a bespoke butcher block island, professional-grade Viking double ovens, and sleek quartz countertops. High-end functionality includes dual KitchenAid dishwashers and custom cabinetry. The primary living spaces flow seamlessly to a wet bar and wood-burning fireplace, ideal for post-round entertaining. An extraordinary floating staircase of hand-built Hungarian wood leads to a versatile upper level with a private balcony overlooking the course. The primary suite serves as a sanctuary, entered through exquisite hand-carved doors imported from Turkey. This retreat features French doors leading to a private courtyard, custom walk-in closets, and a whirlpool jacuzzi tub. Outdoor living is centered around the pool and an expansive lanai with a fully equipped summer kitchen. Notable infrastructure includes a 3-car garage, three AC units, and clear hurricane shutters. This residence offers an elevated Sarasota lifestyle with immediate proximity to world-class golf and the exclusive amenities of the Oaks community. Please note membership of The Oaks is required.

Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)

Listing Agent: Andrea Stultz (941-929-6529)

Remarks: Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.

Listing is courtesy of: PALM PARADISE REALTY GROUP (239-955-7256)

Listing Agent: Maria Domenech (978-204-3219)

Remarks: Tucked away on a quiet street within the prestigious Oaks Club in Osprey, Fl; This elegant residence overlooks the fairway of the Heron 14. This home sits on a Premium golf course lot with additional privacy view across the street . Designed by Toll Brothers, this one story, 3200 sq. Ft. home with 3 bedroom ( plus office ) offers gracious entertaining and comfortable everyday living. A well-appointed kitchen with newer appliances opens seamlessly to a family room for hosting family and friends. Step outside to your private oasis and serene backyard, a perfect place to read or host your Book Club. A new roof and pool cage(2023) have been added. This home has a 3-car garage with an electric car charger. Living in the Oaks Club means enjoying two Championship golf courses, 12 har-tu tennis courts, 4 pickleball courts, gorgeous croquet lawns and a State of the art fitness center with an outdoor heated pool. Membership is required for home ownership. In this premier Golf and Country Club. Enjoy the vibrancy of downtown Sarasota for culture, arts, dining, and shopping. Just a short distance to the world-renowned Siesta Beach and the Gulf coast of Florida. Stop by to learn about the active social calendar - a place to make wonderful memories.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Susan Pelton (941-321-1007)

Remarks: Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.

Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)

Listing Agent: Suki Scollo (941-587-2289)

Remarks: PENTHOUSE CONDO IN WATERFRONT COMMUNITY! Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for soaking up the Florida sunshine and enjoying great views. The gourmet kitchen is a chef’s dream, offering granite countertops, wood cabinetry, stainless steel appliances, and a cozy eat-in area for casual dining. The expansive master suite boasts a private balcony, two walk-in closets, double vanities, a soaking tub, and a separate shower for ultimate relaxation. Additional highlights include a wet bar for entertaining and three separate balconies for outdoor living. Enjoy resort-style amenities such as tennis courts, pickleball, shuffleboard, a heated pool, clubhouse, walking paths, a workout facility, and a convenient kayak launch for endless waterfront adventures. Bring your own boat and take advantage of your separately available assigned boat dock area! When you’re ready to explore, you’ll find yourself just 10 minutes from several Gulf Coast beaches, thousands of acres of parks and preserves, and world-class shopping, dining, and fishing. Quick connections to Sarasota’s vibrant arts scene, the new Mote Marine Aquarium, Spanish Point, the Legacy Trail, and Oscar Scherer State Park are all just minutes away. All of this and you will just be 5 minutes from I-75 where the rest of the world awaits you. Take the elevator to your nearby 2 assigned parking spots under the building. Don’t miss your chance to own this exceptional penthouse—schedule your private showing today!

Listing is courtesy of: KW COASTAL LIVING (941-473-7399)

Listing Agent: Toy Coxey (941-662-0010)

Remarks: Welcome to Bay Street Village in Osprey, gorgeous gated community where maintenance-free living awaits. This immaculate end-unit condo freshly painted with new LVP stairs and flooring features 2 bedrooms, 2 bathrooms, garage, located beneath the unit and offers a private interior stairway leading to your second-floor residence. Open-concept living and dining area are perfect for entertaining beautiful kitchen with center island, walk-in pantry and stainless steel appliances. The primary suite offers a walk-in closet and an ensuite bathroom with dual sinks, a makeup vanity, and a walk-in shower. Bay Street Village provides resort-style amenities, including a sparkling pool and a fitness center, along with plenty of guest parking. The community is dog-friendly, with a fantastic dog park just a short walk outside the gate. Outdoor enthusiasts will appreciate the easy access to the Legacy Trail right on Bay Street. Pine View School for the Gifted (grades 2-12) is conveniently located on the next street. Bay Street offers easy access to Nokomis Beach and the world-famous Siesta Key Beach. Close to shopping and restaurants.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Pamela Kurpiewski (941-952-8159)

Remarks: Calling all WATER enthusiasts! BOATERS DREAM IN SORRENTO SHORES! Just FOUR houses from the Intracoastal Waterway with NO bridges to the Gulf, this beautifully updated waterfront pool home delivers the lifestyle buyers come to Florida searching for. Welcome to Sorrento Shores — a hidden gem perfectly positioned between Venice Island and Siesta Key, where every day feels like a vacation. Situated on an oversized canal-front lot, this move-in ready 3-bedroom, 2-bath home offers quick deep-water access to the Intracoastal and Gulf beyond. Bring your boat, your paddleboards, your fishing gear, and start living the coastal lifestyle immediately. This home is Offered TURNKEY (minus select personal items), has a Private dock with quick open-water access, a 27x40 screened lanai with resurfaced pool for plenty of lazy pool days, and sits on an Oversized .36-acre lot. No need to store your boat trailer off site, there is ample parking for your boat trailer right on your own property. No CDD fees + voluntary HOA only $130/year And the Big-Ticket items have been taken care of: NEW ROOF 2025, NEW SEPTIC SYSTEM 2024, NEW POOL CAGE 2025 SEWER PIPES RELINED 2023-2024, IMPACT WINDOWS 2018, NEW POOL HEATER 2025, NEW WATER HEATER 2024 Newer A/C 2018 Updated baths + fresh interior finishes 2025 Cruise by boat to Casey Key Fish House, Pops Sunset Grill, Snake Island, Midnight Pass, Venice waterfront restaurants, and the Gulf of Mexico — all from your own backyard. This is not just a home… It’s the waterfront lifestyle buyers dream about!

Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)

Listing Agent: Phyllis Coviello (941-408-3265)

Remarks: One or more photo(s) has been virtually staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of relaxation, comfort, and everyday convenience. From the moment you walk through the door, the tranquil pond views immediately draw your attention, creating a sense of calm that carries throughout the home. Imagine starting your mornings on the screened lanai with coffee in hand, overlooking the sparkling water feature while enjoying the warm Florida breeze and peaceful surroundings. With over 1,400 square feet of thoughtfully designed living space, this beautifully maintained 2-bedroom, 2-bathroom condo also features a versatile den, separate laundry room, and attached one-car garage. Rare first-floor units with water views and this level of convenience are highly desirable for full-time residents, seasonal owners, and investors alike. The open-concept floor plan was designed to maximize both comfort and entertaining. The kitchen showcases granite countertops, solid wood cabinetry, stainless steel appliances, stylish backsplash details, a spacious island, and breakfast bar seating that flows seamlessly into the bright and inviting living area. Crown molding, modern lighting, fresh neutral paint, and updated flooring throughout elevate the home with a clean and timeless feel. The spacious primary suite serves as a private retreat featuring peaceful water views, a large walk-in closet, linen closet, and an updated en-suite bathroom complete with dual sinks and a custom walk-in tile shower. A generously sized guest bedroom, beautiful guest bath, and flexible bonus room provide endless possibilities for guests, a home office, hobby space, or additional lounge area. Bay Street Village offers true maintenance-free living with resort-style amenities including a sparkling pool, fitness center, clubhouse, and beautifully maintained grounds. Centrally located between Sarasota and Venice, residents enjoy quick access to world-renowned Gulf beaches including, Nokomis Beach, and Venice Beach, along with downtown Sarasota, marinas, waterfront dining, shopping, golf, entertainment, Sarasota Bay, the Legacy Trail, and countless local restaurants and attractions. Located near the nationally recognized Pine View School and tucked away from the heavy tourist traffic while still remaining close to everything, this condo offers the perfect combination of convenience, comfort, and the relaxed coastal lifestyle that everyone dream about when moving to Florida. Whether you are searching for a primary residence, seasonal escape, or investment opportunity, this exceptional waterfront condo delivers location, lifestyle, and value all in one. Schedule your private showing today and experience firsthand why this hidden gem in Bay Street Village is the perfect place to call home.

Listing is courtesy of: KW COASTAL LIVING II (941-556-0500)

Listing Agent: Jozefina Wells (941-993-3051)

Remarks: Spacious 3-bedroom, 3-bath home featuring high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. This home combines comfort and style with light-filled living spaces. Enjoy Florida living at its best with a private pool and amazing lanai area with plenty of covered patio. The oversized two car garage provides plenty of space for a golf cart. Located in a highly sought-after Marina community offering a clubhouse and resort-style amenities. There are recreational activities for all ages, tennis, pickleball, bocce ball, playground, kayak launch and storage, jet ski pads, fishing & boating. Southbay Yacht & Racquet Club is a community like no other in that it has a private 172 boat slip Marina with deep water able to accommodate boats up to 58 feet. Walk, bike or take your golf cart to beaches, shopping, restaurants & tiki bars.

Listing is courtesy of: GOLF & BAY PROPERTIES LLC (941-539-8400)

Listing Agent: Sharon Lewis (941-966-5400)

Remarks: One or more photo(s) has been virtually staged. Exceptional Waterfront Estate on North Casey Key. Set along the coveted shores of North Casey Key, this exceptional waterfront residence presents a rare opportunity to experience the very best of coastal Florida living. Nestled within the sought-after Palmer neighborhood and lovingly maintained by the same discerning owners since 1999, the home reflects a true sense of pride, care, and thoughtful stewardship throughout. Positioned on an expansive 0.68-acre parcel with 131 feet of Sarasota Bay frontage and two deeded private beach access points, the property is surrounded by lush tropical landscaping and majestic oaks, creating a serene setting defined by timeless Old Florida charm. From tranquil mornings to vibrant evenings, enjoy both sunrises and sunsets from your own private waterfront retreat. Designed for both everyday comfort and effortless entertaining, the residence offers a traditional yet spacious layout featuring formal living and dining rooms, a generous family room, private office, bonus room, and a serene first-floor primary suite. Three additional guest bedrooms provide ample space for family and visitors, each with access to the outdoors to capture bay breezes and water views. Outdoor living is equally inviting, with a screened-in pool, covered boathouse accommodating vessels over 25 feet, and direct bay access for kayaking or boating. Whether entertaining poolside, gathering dockside, or enjoying quiet moments along the shoreline, the setting is both versatile and inviting. Meticulously updated over time, the home includes a metal roof, two new HVAC systems, PGT impact windows, re-piping, new dock, and much more...offering peace of mind while preserving its character. With no storm damage and move-in-ready condition, the opportunity to begin enjoying the waterfront lifestyle is immediate. Ideally located just 15 miles south of downtown Sarasota and moments from Pine View School, shopping centers, nature parks, and the Legacy Trail, this property offers a unique balance of privacy and accessibility. A truly special home, thoughtfully cared for and ready for its next chapter...where generations can gather, relax, and create lasting memories. Private tours available available with notice.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Brandy Sheldon (941-724-0469)

Remarks: Tucked behind the private gates of The Oaks Club side, in one of Sarasota’s most prestigious and sought-after country club enclaves, this exquisite residence captures the essence of refined Florida living. Ideally situated just moments from the clubhouse and overlooking the manicured fairways of the Eagle Course, the home offers a rare blend of privacy, scale, and serene golf course vistas that stretch endlessly from the expansive screened lanai. Spanning over 3,500 square feet, this beautifully appointed single level home features three generously sized bedrooms, a dedicated office, and three-and-a-half baths, all thoughtfully designed to balance sophistication with everyday comfort. From the moment you enter, a sense of understated elegance unfolds—gracious formal living spaces anchored by a statement fireplace, soaring tray ceilings, intricate crown molding, and an abundance of natural light that enhances every architectural detail. The primary suite serves as a true retreat, offering impressive proportions, a substantial walk-in closet, and a spa-inspired bath designed for relaxation. Additional living spaces flow effortlessly, including a well-equipped laundry room with custom built-in workspace, ideal for modern living. Every inch of the home reflects careful attention to detail, from the finishes to the functional layout. Outdoors, the residence truly shines. The screened lanai becomes a private sanctuary, complete with a sparkling pool and spa, perfectly positioned to capture sweeping views of the 4th hole. Whether entertaining guests or enjoying quiet evenings, this space delivers an elevated indoor-outdoor lifestyle synonymous with luxury coastal living. Enhancing both comfort and peace of mind, the home is equipped with a whole-house generator, and Security Camera's outside and the oversized three-car side entrance garage and circular paver driveway provide both convenience and impressive curb appeal. Quick notes to take away: Roof - 2023 / A/C (both units) - 2024 Ownership within The Oaks grants access to an unparalleled private club experience. Residents enjoy two championship 18-hole golf courses, impeccably maintained HAR-TRU tennis courts, newly introduced pickleball facilities, and a state-of-the-art Wellness and Fitness Center exceeding 7,500 square feet. Complemented by an exceptional culinary program and a vibrant calendar of curated social events, The Oaks offers a lifestyle defined by elegance, activity, and connection. Club membership is required, within this distinguished Sarasota community.

Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)

Listing Agent: Steven Kepecz, Pa (941-376-6411)

Remarks: One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and entertaining. Elegant tray ceilings, crown molding, and 9-foot ceilings enhance the first floor living space. The flooring is a beautiful wood look tile and LVP throughout the home. Upstairs, you’ll find both bedrooms, including the primary suite with a walk-in closet. As an extra bonus, there is a two-car garage. There is a community pool where you can enjoy a refreshing swim or relax poolside. Venture out to nearby Gulf beaches, shopping, dining, Oscar Sherer State Park and the Legacy Trail. Whether you’re looking for a year-round residence or a seasonal retreat, this home is the perfect fit. Don’t miss this opportunity—schedule your showing today!

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-486-8686)

Listing Agent: Kimberly Werla, Pa (941-979-2757)

Remarks: Beautifully Maintained 3-Bedroom Home with No HOA or Deed Restrictions Welcome to this immaculate 3-bedroom, 2-bath home, newly built in 2021 and perfectly located just minutes from top-rated beaches, shopping, dining, and entertainment. This move-in-ready home offers a clean, modern design with a spacious open floor plan that’s ideal for both relaxing and entertaining. Enjoy cooking in the stylish open kitchen, complete with granite countertops and ample cabinet space. Luxury vinyl flooring runs throughout the home, adding durability and a sleek, contemporary feel. With no HOA, CDD, or deed restrictions, this property provides true freedom and flexibility—bring your boat, RV, or other recreational vehicles with ease. The generous lot offers plenty of room for parking and outdoor enjoyment. Don’t miss this rare opportunity to own a centrally located, low-maintenance home in a highly desirable area!

Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-923-5835)

Listing Agent: Kano Keller (941-915-1297)

Remarks: This one is an impressive little gem located in sought after Southbay Yacht & Racquet Club. So many improvements, upgrades and updates all you need to do is bring your furniture and move right in. As we approach the hurricane season, you will enjoy the sense of security provided by the replacement of all windows, sliders and doors with hurricane impact glass. A secluded back yard retreat awaits you with a spacious covered lanai looking onto the updated heated self draining pool and the wooded back yard. Some of the home highlights are: UPDATED KITCHEN AND BATHS, PORCELAIN TILE IN THE MAIN LIVING AREAS, IMPACT WINDOWS ABOUT 11-12 YEARS AGO. The owners have continued with the updates including: NEW METAL ROOF 2023, REPLACED MAIN ELECTRICAL PANEL AND ADDED 220 OUTLET FOR FUTURE GENERATOR. ADDED WHOLE HOUSE AIR PURIFICATION 2022, NEW EPOXY GARAGE FLOOR 2020, A/C AND HEAT PUMP SYSTEM 2018, REPLACED 3 DOORS WITH IMPACT GLASS, REPLACED 3 SLIDING GLASS DOORS WITH IMPACT GLASS 2015, COMPLETE POOL AND LANAI RENOVATION INCLUDING HEAT PUMP AND DECK PAVERS 2017, REPLACED GARAGE DOOR WITH IMPACT RESISTANT DOOR AND VENTS. REPLACED APPLIANCES: MICROWAVE 2025, REFRIGERATOR AND WINE COOLER 2024, RANGE, WASHER, DISHWASHER, 2023, HOT WATER HEATER 2023, REPLACED CARPET WITH CERAMIC TILE 2021 AND CUSTOM PLANTATION SHUTTERS THROUGHOUT THE HOUSE. There are more items I haven’t mentioned but you need to come take a look for yourself. There is a detailed list of improvements available. The Southbay community has much to offer! One of the few neighborhoods with its own exclusive marina. Dock space is only available to residents and is offered at very reasonable rates and can accommodate almost any size boat. Southbay is an active community with many clubs and gatherings at the remodeled clubhouse overlooking the marina. The clubhouse features two kitchens, ballroom, fitness center, card room, even a “livingroom” with grand piano. There’s something for everyone! Pickleball courts, tennis courts, bocce ball, community pool, playground, kayak launch and storage. Southbay is also a golf cart community! The Southbay location is in easy reach of shopping, grocery stores, restaurants, main roads, downtown Sarasota and downtown Venice. Local beaches including Nokomis (5 miles away), Siesta Key (10 miles away), Venice (7 miles) are all within an easy drive. Local restaurants including the famous Casey Key Fish House and Tiki bar are close at hand. Come and see what makes this home and Southbay so special!

Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)

Listing Agent: Pat Williams (941-289-6231)

Remarks: One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional lawn care and irrigation are covered by the monthly fees. Designed for both everyday comfort and effortless entertaining, the residence offers 3 bedrooms, 3.5 baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Inside, refined architectural elements, including crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces, create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living spaces, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen featuring custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting. A Sonos sound system extends throughout the residence. The primary suite serves as a retreat with vaulted ceilings, a bay window sitting area, outdoor access, and a fully renovated spa-inspired bath completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. Additional baths have also been extensively renovated with elevated finishes and designer fixtures, while the updated laundry room introduces custom storage, shiplap detailing, and functional built-ins with a refined coastal aesthetic. Upstairs, a spacious bonus room with a fireplace opens directly to a newly renovated second-story deck. With a full bathroom, the second floor is an exceptional flex space ideal for guests, recreation, or private lounging among the treetops. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and serene preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor, new lanai screening and aluminum framing, exterior paint completed in 2025, and a new second-story flat roof with a warranty. Located within the gated community of Bishops Court inside The Oaks Preserve, residents enjoy 24 hour guarded gates, maintenance-free living alongside access to one of the region’s premier private club lifestyles, featuring two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has been awarded the Platinum Clubs of America, Distinguished Emerald Residential Country Club, and Audubon International Certified designations. Located between Sarasota and Venice, Osprey is known for its natural beauty, waterfront lifestyle, and easy access to everyday conveniences. Residents are just moments from Siesta Key, downtown Sarasota’s dining and cultural attractions, marinas, shopping, Legacy Trail, and the renowned Pine View School, creating an ideal setting for both year-round living and seasonal enjoyment.

Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)

Listing Agent: Joel Schemmel (941-587-4894)

Remarks: A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical landscaping on a quiet cul-de-sac in The Oaks Bayside. Double entry doors open to a marble foyer and wood floors that set the tone for quality throughout. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook overlooking the pool and waterfall feature. The elegant primary suite offers marble floors, soaring ceilings, plantation shutters, and private access to the pool for an early swim or late-night dip. A glamorous dressing area leads to the spa-like bath with soaking tub, walk-in shower, and marble finishes. Two additional oversized en suite bedrooms provide comfort and privacy for guests. A large laundry room with ample cabinetry and an adjacent private sauna complete the interior. Outdoors, the free-form pool with rock outcroppings and waterfall is a showstopper, surrounded by both shaded and open areas for dining and relaxing. With two adjoining lots preserved as gardens, this home offers rare seclusion in a natural setting. Ownership includes membership in The Oaks Club, Sarasota’s premier golf and country club, featuring two championship courses, tennis, WellFit center, fine dining, and a vibrant year-round social calendar—all in the heart of South Sarasota.

Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)

Listing Agent: Steve Abbe (941-400-3969)

Remarks: One or more photo(s) has been virtually staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey— perfectly situated on a premium corner lot with NO HOA and NO CDD fees! This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed for both everyday comfort and effortless entertaining. The spacious living area features sliding glass doors that lead directly to your screened-in lanai and sparkling inground pool, creating seamless indoor-outdoor living. The well-equipped kitchen boasts abundant cabinetry and generous counter space, making it ideal for preparing meals and hosting gatherings. Each of the three bedrooms includes a walk- in closet, providing ample storage and convenience. Retreat to the primary suite, where you’ll find a spa-like jetted tub—perfect for unwinding after a long day. Step outside and enjoy the added bonus of an outdoor shower, ideal for rinsing off after a swim. Additional highlights include a two-car garage, functional layout, and a yard that offers both privacy and potential. With its corner lot location and private pool this home delivers the ultimate Florida lifestyle. Opportunities like this don’t last—schedule your private showing today and make this Osprey gem yours!

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Jeff Jones (205-902-3584)

Remarks: Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting. Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to the dining, shopping, and cultural attractions of Venice and Sarasota. Behind a gated entrance, the home features three bedrooms, a private office, and three-and-a-half baths, all thoughtfully updated to celebrate its extraordinary Gulf-front setting. Expansive windows and sliding glass doors frame breathtaking water views while filling the interiors with natural light and coastal breezes. Rich architectural details reflect its hacienda-inspired design, including wood beams and moldings, barrel-brick ceilings, Mexican tile and wood floors, brick accents, artisanal mosaic tile, and hand-painted stair risers. Hurricane-impact windows and doors, a new roof, a new pool, and updated air-conditioning and pool equipment provide both peace of mind and modern comfort. The gourmet kitchen is beautifully appointed with custom cabinetry and Wolf appliances, creating an ideal setting for entertaining after a day on the beach. The primary suite is a private retreat with a sitting room, wet bar, soaking tub, walk-in closet, and private balcony overlooking the Gulf. Two additional en-suite guest bedrooms provide comfort and privacy for family and visitors. A spiral staircase leads to the rooftop deck, where panoramic views stretch from the Gulf to the Intracoastal Waterway. Outside, the courtyard-style pool, fountain, tiled terraces, and lush tropical gardens create a tranquil setting for authentic alfresco living. This is an exceptional opportunity to experience the privacy, beauty, and effortless lifestyle of Gulf-front living on Casey Key.

Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)

Listing Agent: Lisa Napolitano (941-993-0025)

Remarks: This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Boating enthusiasts will appreciate the included 50-foot boat slip accommodating vessels 44 feet, ideal for exploring the Intracoastal Waterway and beyond. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!

Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)

Listing Agent: Megan E. George, Pa (941-726-1998)

Remarks: **STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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.

Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)

Listing Agent: Mark Lyda (941-586-2670)