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$749,900

Virtually Staged. Welcome to your ultimate lakeside maintenance free sanctuary! Nestled in a premier community renowned for its top-rated gifted school district, this expanded floor plan in the Willow Bend Community offers 2,183 square feet of meticulously designed, sun-drenched living space with high ceilings, crown molding, and ceiling fans. Boasting 50 feet of lakefront views, the property features a North-facing orientation, allowing you to bask in the desirable southern rear exposure from your covered lanai with a retractable awning, sparkling pool, or soothing spa with a cascading waterfall—all without the harsh glare of direct sun. Through the glass paned front doors into an open-concept haven defined by a neutral color palette that acts as a blank canvas for your personal decor. Porcelain tile floors flow seamlessly through the common areas, while beautiful, warm hardwood floors bring comfort and sophistication to the bedrooms. Flooded with natural light, the main living areas feature large windows equipped with remote-controlled custom Hunter Douglas blinds for effortless light management. Just beyond the formal living and dining areas is the heart of the home in the inspired kitchen that serves as the perfect entertainment hub and a breakfast dinette area that overlooks the pool and spa. It features a counter top that flows into the main living room and the vibrant pool deck, sleek quartz countertops, and premium stainless steel appliances. Cooking appliances are electric, but you do have the option of installing gas if preferred. Pantry shelving is equipped with pull-outs. Working from home is a luxury in the oversized office/study, completely outfitted with a custom built-in desk and extensive shelving and drawers. The primary suite is a true homeowner's retreat, generously scaled to comfortably fit a king-sized bed, nightstands, and a dedicated sitting area. It offers two spacious walk-in closets and a spa-like ensuite bathroom complete with a water closet, a deep soaking tub, a glass-enclosed shower, and two separate vanities packed with storage. The two additional bedrooms are equally impressive, each featuring large windows and substantial closet space. Peace of mind and efficiency are built right into this structurally sound property. The majority of the windows and doors are hurricane-rated, supplemented by heavy-duty accordion shutters for the lanai sliding doors. Living here means enjoying a low-maintenance, resort-style lifestyle. The comprehensive HOA fee conveniently covers lawn care maintenance, high-speed internet, basic cable TV, and irrigation water. Beyond your front door, the neighborhood provides access to fantastic family amenities, including tennis, pickleball and basketball courts, a fully equipped workout center, a community pool & spa, and a playground. Have a piece of mind with a HVAC installed in 2023, a gas water heater from 2018 and a washer and dryer from 2021, and a NEW pool heater installed September 2026, all well maintained and in perfect working order. The location of Willow Bend offers not only a top rated gifted school district, its proximity to shopping, top rated hospitals and medical care, you are also close to some of the most beautiful beaches of Osprey, Nokomis & Venice. This lakefront masterpiece perfectly combines luxury, safety, and community—that you can start enjoying today!

3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code

Virtually Staged. Welcome to your ultimate lakeside maintenance free sanctuary! Nestled in a premier community renowned for its top-rated gifted school district, this expanded floor plan in the Willow Bend Community offers 2,183 square feet of meticulously designed, sun-drenched living space with high ceilings, crown molding, and ceiling fans. Boasting 50 feet of lakefront views, the property features a North-facing orientation, allowing you to bask in the desirable southern rear exposure from your covered lanai with a retractable awning, sparkling pool, or soothing spa with a cascading waterfall—all without the harsh glare of direct sun. Through the glass paned front doors into an open-concept haven defined by a neutral color palette that acts as a blank canvas for your personal decor. Porcelain tile floors flow seamlessly through the common areas, while beautiful, warm hardwood floors bring comfort and sophistication to the bedrooms. Flooded with natural light, the main living areas feature large windows equipped with remote-controlled custom Hunter Douglas blinds for effortless light management. Just beyond the formal living and dining areas is the heart of the home in the inspired kitchen that serves as the perfect entertainment hub and a breakfast dinette area that overlooks the pool and spa. It features a counter top that flows into the main living room and the vibrant pool deck, sleek quartz countertops, and premium stainless steel appliances. Cooking appliances are electric, but you do have the option of installing gas if preferred. Pantry shelving is equipped with pull-outs. Working from home is a luxury in the oversized office/study, completely outfitted with a custom built-in desk and extensive shelving and drawers. The primary suite is a true homeowner's retreat, generously scaled to comfortably fit a king-sized bed, nightstands, and a dedicated sitting area. It offers two spacious walk-in closets and a spa-like ensuite bathroom complete with a water closet, a deep soaking tub, a glass-enclosed shower, and two separate vanities packed with storage. The two additional bedrooms are equally impressive, each featuring large windows and substantial closet space. Peace of mind and efficiency are built right into this structurally sound property. The majority of the windows and doors are hurricane-rated, supplemented by heavy-duty accordion shutters for the lanai sliding doors. Living here means enjoying a low-maintenance, resort-style lifestyle. The comprehensive HOA fee conveniently covers lawn care maintenance, high-speed internet, basic cable TV, and irrigation water. Beyond your front door, the neighborhood provides access to fantastic family amenities, including tennis, pickleball and basketball courts, a fully equipped workout center, a community pool & spa, and a playground. Have a piece of mind with a HVAC installed in 2023, a gas water heater from 2018 and a washer and dryer from 2021, and a NEW pool heater installed September 2026, all well maintained and in perfect working order. The location of Willow Bend offers not only a top rated gifted school district, its proximity to shopping, top rated hospitals and medical care, you are also close to some of the most beautiful beaches of Osprey, Nokomis & Venice. This lakefront masterpiece perfectly combines luxury, safety, and community—that you can start enjoying today!

1328 Thornapple Drive, Osprey

$4,790,000

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey

$275,000

Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.

1 Beds ⋅ 1 Baths ⋅ Windsor Lodge At The Oaks SubDv. ⋅ 34229 Zip Code

Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.

51 Macewen Drive Unit 12, Osprey

$235,000

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey

$2,399,000

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

49 Osprey Point Drive, Osprey