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758 Sarabay Road Unit 5, Osprey
$598,000
2 Beds ⋅ 2 Baths ⋅ Heron Bay Club SubDv. ⋅ 34229 Zip Code
Beautiful views of Little Sarasota Bay and a peaceful waterfront setting are just the beginning of what makes this updated villa in Heron Bay Club so appealing. Tucked along the shores of Little Sarasota Bay, this intimate waterfront community consists of just 25 single-story villas situated on approximately 10 acres across from the northern end of Casey Key. Surrounded by natural beauty and offering a quiet, private setting, Heron Bay Club captures the charm of Old Florida without sacrificing convenience. The villa enjoys beautiful views of the bay, along with the community pond and its decorative fountain, creating a picturesque backdrop. Interior improvements include updated electrical outlets and switches, a tankless water heater, newer appliances, and an A/C system replaced in 2021. A private courtyard offers additional outdoor living space, while the attached two-car garage is a particularly desirable feature not found in every residence within the community. The spacious attic with high ceilings provides even more storage, a welcome bonus in condominium living. For those who enjoy spending time on the water, Heron Bay Club has plenty to offer. Residents enjoy a heated swimming pool, tennis courts, and a fishing pier. Boating enthusiasts will especially appreciate the availability of boat dockage at no additional fee, providing convenient access to the Intracoastal Waterway and Gulf. Whether boating, fishing, or simply watching the dolphins, manatees, and coastal birds that frequent the area, the waterfront lifestyle is an everyday part of life here. The community's western exposure also provides a beautiful setting to enjoy sunsets over Little Sarasota Bay. Another standout feature of Heron Bay Club is just how much is included in the association fee. In addition to maintaining the beautifully landscaped grounds and community amenities, the fee covers water, high-speed internet, cable television, pest control, building flood insurance, exterior building maintenance and painting, roof maintenance and repairs, trash collection, and more. With so many services and expenses already included, residents can enjoy the benefits of a low-maintenance lifestyle with fewer individual bills and responsibilities. Unlike traditional multistory condominium buildings, Heron Bay Club's single-story villas offer the privacy and convenience of having no elevators or neighbors overhead. The community's small size and private courtyards create a more residential feel than what is typically found in larger waterfront condominium developments. Despite its peaceful setting, Heron Bay Club is conveniently located near beautiful Gulf beaches, shopping, restaurants, and the arts and cultural attractions of Sarasota. With its combination of water views, boating access, extensive association benefits, and intimate community atmosphere, this home offers a distinctive opportunity to enjoy Florida's Gulf Coast lifestyle.

758 Sarabay Road Unit 5, Osprey

455 Oak Point Road, Osprey
$600,000
4 Beds ⋅ 3 Baths ⋅ Blackburn Point Woods SubDv. ⋅ 34229 Zip Code
It’s always about the experience of living near Casey Key and the Intracoastal Waterway from this two-story town home in the maintenance-free community of Blackburn Point Woods. Nearby marina, waterfront park with boat ramp and trail for those seeking a lifestyle that celebrates the water, the wildlife, and the open spaces of Florida — nothing compares. A charming entry to the home leads to the inviting great room with soaring ceilings and a wood-burning fireplace. The first level features a private two-car garage and paver drive, French doors leading to a lanai and private pool area, and a secondary patio with an above-ground hot tub. With two bedrooms on the first level, one a generously sized primary with an en-suite bath, and two on the second, there is abundant space for everyone. Upper-level area for a den and a space for home fitness and an oversized closet. The chef's kitchen has solid wood cabinetry; topped in granite, there is kitchen dining as well as adjacent spacious formal dining. Thoughtful dry bar area for entertaining. Each floor/area of the residence has balconies for seamless indoor/outdoor living, the second-level 8-by-18 balcony has had wood replaced in 2026. Luxury Vinyl flooring throughout the living areas provides warmth and sophistication. Nearby are Publix, CVS, ice cream and coffee shops and numerous restaurants. This location is a short distance to Bayfront Park, tiki bar and two waterfront restaurants, a short scenic drive down Casey Key takes you to Nokomis Beach. The community amenities offer two heated pools, pickleball and tennis, a clubhouse and gym. This extraordinary home is the ideal frame for exceptional, easy living. Home is being offered turnkey furnished, excluding personal effects, some homeowner's decor, and staging decor.

455 Oak Point Road, Osprey

232 Hidden Bay Drive Unit 303, Osprey
$569,000
2 Beds ⋅ 2 Baths ⋅ Baypointe Vista SubDv. ⋅ 34229 Zip Code
Waterfront resort-style living is behind the gates of Hidden Bay, set along the shores of the Intracoastal Waterway, Little Sarasota Bay, and a tranquil preserve and park in the heart of Osprey. This third-floor residence, accessible by elevator, has been tastefully remodeled and offers two full bedrooms, each with en-suite baths, a spacious den and a three-car garage. The lanai’s exterior sliders open to an all-season, tiled living area where you can enjoy birdwatching and wildlife in the mangroves, observe passing boats, feel gentle bay breezes and take in spectacular sunsets. The wonderfully efficient kitchen features Corian countertops, a breakfast bar with seating for four, new (2025) LG stainless steel appliances and abundant pantry storage within newly outfitted cabinetry, complete with pullout drawers in the kitchen and baths. This beautifully appointed home showcases Acacia engineered flooring, high ceilings, a generous laundry room with newer GE appliances, a sink, tile flooring and ample storage, plus a den or office off the breakfast area. This condominium features a rare three-car garage which includes a private single garage, allowing this space to be used as art studio workshop, or the ever-elusive onsite storage unit along with a separate and spacious two-car garage on the first level. A new roof and updated elevator motor were added in 2025, along with completed Milestone and Reserve studies. Many of the attractive furnishings are available under a separate bill of sale. This exceptional gated waterfront community features a 1,500-foot elevated wooden boardwalk winding through lush landscaping and palm-lined grounds, leading to a private bay front fishing pier. Residents enjoy a renovated clubhouse offering a full kitchen, with granite bar and graciously appointed social area which can be used for private events. Owners also enjoy a fully stocked library, a professional fitness center, and an entertainment and media area. Outside the clubhouse, there is a heated pool, hot tub and tiki hut for additional social gatherings. Hidden Bay is conveniently near restaurants, shopping, Legacy Trail and Nokomis Beach. Osprey is a lovely area between Sarasota and Venice featuring old Florida vibes, peaceful surroundings, and an easy, quiet, lifestyle. Seller willing to lease back.

232 Hidden Bay Drive Unit 303, Osprey

250 Hidden Bay Drive Unit 301, Osprey
$695,000
3 Beds ⋅ 3 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Enjoy sweeping water views and stunning sunsets over Little Sarasota Bay from this spacious third-floor corner residence in the gated waterfront community of Edgewater at Hidden Bay. Built in 2017 and moved into in January 2018, this three-bedroom plus den, 2.5-bath condominium offers nearly 2,200 square feet of living space with easy elevator access and one assigned parking space in the building. The attractive open floor plan features soaring ceilings, impact-rated windows and sliding doors, easy-to-maintain tile plank flooring and abundant natural light throughout. The kitchen includes granite countertops, solid wood cabinetry, stainless steel appliances and custom storage with pullout drawers. The living area opens to a large, screened-in terrace with privacy screens and expansive bay views. The primary suite includes dual walk-in closets and a luxurious bath with dual quartz vanities, decorative tile flooring, a makeup vanity and a walk-in shower. Additional features include a private den/office, an in-unit laundry room, two full baths and a powder room, and air conditioner from 2023. Edgewater at Hidden Bay is a gated, resort-style community set on 14 acres along Little Sarasota Bay and the Intracoastal Waterway, directly across from Casey Key. Community amenities include a waterfront clubhouse with a kitchen and quartz bar, a heated pool and spa, a fitness center, a library, a tiki hut with grilling stations, pickleball and tennis courts, a kayak launch, a fishing pier, a dog play area, and an elevated boardwalk through mangroves and palm-lined grounds. Hidden Bay is conveniently in Osprey, just south of Sarasota, near area beaches, shopping and dining and only minutes from Venice.

250 Hidden Bay Drive Unit 301, Osprey

14041 Bellagio Way Unit 315, Osprey
$640,000
3 Beds ⋅ 2 Baths ⋅ The Villas At Bellagio Harbor Village SubDv. ⋅ 34229 Zip Code
There is something extraordinary about living on the water, where passing sailboats, coastal breezes, and the beauty of the marina become part of everyday life. Welcome to Osprey Harbor Village, an intimate waterfront community perfectly positioned between Sarasota and Venice, where timeless elegance meets the relaxed sophistication of Southwest Florida living. From the moment you enter, the welcoming foyer introduces a thoughtfully designed residence that balances comfort, elegance, and effortless entertaining. The spacious kitchen features rich upgraded wood cabinetry, granite countertops, stainless steel appliances, and a generous breakfast bar where family and friends naturally gather. An inviting dining area transitions into the comfortable living room, with access to the expansive terrace that truly sets this home apart. Whether entertaining guests, enjoying a quiet evening, or simply watching the activity along the waterfront, this outdoor living space is destined to become one of your favorite places. The generously sized primary suite offers a peaceful retreat with a spacious walk-in closet and an ensuite bath featuring dual vanities, a soaking tub, separate shower, and private water closet. Two additional bedrooms provide wonderful flexibility for visiting family and friends, a home office, or whatever suits your lifestyle. Beyond the residence, Osprey Harbor Village offers an exceptional waterfront experience. This boutique community of just 54 condominiums showcases distinctive Italian-inspired architecture and was constructed in 2006 to hurricane building standards. Boating enthusiasts will appreciate the marina setting and approximately 7-foot draft channel, providing access to the beautiful waterways that make Florida's Gulf Coast a boating paradise. Whether you enjoy sailing, cruising, fishing, kayaking, or simply admiring the boats from your terrace, life here revolves around the water. The community amenities create an atmosphere that feels more like a private waterfront resort. Enjoy a newly renovated, fully equipped fitness center, sparkling community pool, poolside grilling area, relaxing spa, sauna, steam room, fishing dock, and kayak launch. Spend your afternoons poolside, take a peaceful paddle along the waterways, or gather with friends after a day of exploring the coast. Additional conveniences include two assigned garage parking spaces, onsite management, and a pet-friendly environment welcoming up to two large dogs. And the location? It's one of the best parts. Imagine being able to stroll to waterfront dining at Deep Lagoon Seafood & Oyster House or the beloved Casey Key Fish House, enjoy the casual atmosphere of a nearby tiki bar, or explore the waterfront park just across the street. The beautiful beaches of Casey Key are only a short drive away, while Publix, shopping, restaurants, medical facilities, and the endless attractions of Sarasota and Venice are all conveniently nearby. From boating adventures and beach days to waterfront dining and peaceful evenings at home, the possibilities are endless. What makes Osprey Harbor Village truly special isn't simply the architecture, the amenities, or even the spectacular marina setting. It's the lifestyle that comes with it. Spend more time outdoors, entertain the people you love, and enjoy the beauty of coastal living in a community that feels both exclusive and welcoming. Discover the waterfront lifestyle waiting for you at Osprey Harbor Village today!

14041 Bellagio Way Unit 315, Osprey

335 Park Trace Boulevard, Osprey
$739,000
3 Beds ⋅ 2 Baths ⋅ Park Trace Estates SubDv. ⋅ 34229 Zip Code
Virtually Staged. Welcome to 335 Park Trace Blvd, an exceptional residence in the sought-after Park Trace Estates of Osprey, close to Pineview Education Center and The Legacy Trail where refined interiors, custom craftsmanship, and spectacular water views come together to create an elegant Florida retreat. From the moment you enter, the home makes a statement with its open living and dining spaces, dramatic triple tray ceilings, custom woodwork, and beautifully detailed wainscoting. A custom electric fireplace serves as a striking focal point, while the private den is enhanced by custom built-in shelving and handsome bookcases—an ideal setting for a home office, library, or quiet retreat. The kitchen features a Viking gas range, a Bosch dishwasher and refrigerator, offering both style and functionality for everyday living and entertaining. Designed for an exceptional indoor-outdoor lifestyle, the home opens to an extraordinary 44' x 39' screened lanai, featuring a gas-heated saltwater pool and approximately 32' x 24' of covered outdoor living space. Whether hosting an elegant gathering or enjoying a quiet evening at home, the expansive outdoor setting provides a front-row seat to the beautiful water views. The residence offers three generously proportioned bedrooms, each complemented by plantation shutters and an updated Jack & Jill Bath. The luxurious primary suite is a private sanctuary, featuring a spacious bath with a walk-in shower, soaking tub, and large walk-in closet. Important updates provide added peace of mind, including a new flat tile roof installed in 2026, plus an updated A/C system and hot water heater, both replaced in 2022. A large two-car garage adds valuable functionality, complete with a workbench and impact-rated garage door, providing ample space for vehicles, storage, and projects. With its remarkable water views, extensive custom millwork, designer-quality details, resort-style pool and lanai, updated systems, and exceptional outdoor living space, this home is waiting for you.

335 Park Trace Boulevard, Osprey

120 Villa Drive Unit 120, Osprey
$455,000
2 Beds ⋅ 2 Baths ⋅ Sorrento Villas SubDv. ⋅ 34229 Zip Code
FULLY FURNISHED WATERFRONT VILLA • PRIVATE DOCK WITH 10,000-LB BOAT LIFT • NO FIXED BRIDGES • DIRECT ACCESS TO THE INTRACOASTAL WATERWAY & GULF OF AMERICA! BRING YOUR BOAT AND START LIVING THE FLORIDA WATERFRONT LIFESTYLE! Welcome to this fully furnished, 2-bedroom, 2-bath waterfront villa in Sorrento Villas, offering an exceptional boating opportunity with NO FIXED BRIDGES between your private dock and the Intracoastal Waterway! Featuring a private dock, 10,000-lb boat lift and unobstructed bridge clearance to the ICW, this property is especially appealing to boating enthusiasts seeking convenient access for larger vessels. Cruise the Intracoastal Waterway, head into the Gulf of America, explore Siesta Key and Midnight Pass, or spend the afternoon discovering waterfront restaurants and nearby coastal destinations. With your boat just steps from your back door, the Florida boating lifestyle is yours to enjoy! Inside, discover 1,404 square feet of inviting living space, offered FULLY FURNISHED for a convenient, turnkey transition to waterfront living. The open floor plan features tile flooring, a spacious living area and an updated kitchen with wood cabinetry, granite countertops, stainless steel appliances, a large island and an extended breakfast bar. A natural stone accent wall adds character, while expansive windows and glass doors fill the living areas with natural light and showcase the waterfront setting. Outdoor living is where this property truly shines! Step onto your screened lanai and enjoy peaceful canal views, tropical landscaping and the coastal breeze. Just beyond the lanai, a limestone walkway leads to your waterfront patio and private dock, creating an inviting setting for morning coffee, afternoon relaxation or evening conversations overlooking the water. Boating enthusiasts will appreciate the updated dock, 10,000-lb boat lift, dedicated fish-cleaning station and updated water and electrical connections. The dock approach has also been raised with additional cement. Numerous improvements include a new electrical panel and breakers, new lanai screening, rain gutters, updated landscaping, a new garage door motor, track and keypad, luxury vinyl plank flooring in the primary bedroom and an updated kitchen faucet. Additional features include hurricane shutters, a tile roof installed in 2009, an A/C system installed in 2015 and an attached garage. Ideally located in Osprey between Sarasota and Venice, this waterfront retreat offers convenient access to Siesta Key, Nokomis Beach, Oscar Scherer State Park, shopping, dining and outdoor recreation. FULLY FURNISHED AND READY FOR YOUR NEXT CHAPTER! With no fixed bridges to the Intracoastal Waterway, direct boating access to the Gulf of America, a private dock and a 10,000-lb boat lift, this property offers the freedom to explore Southwest Florida's waterways right from your backyard. YOUR BOAT. YOUR DOCK. YOUR GATEWAY TO THE GULF!

120 Villa Drive Unit 120, Osprey

145 Edgewood Drive, Osprey
$175,000
2 Beds ⋅ 2 Baths ⋅ Arbors SubDv. ⋅ 34229 Zip Code
Discover comfortable Florida living in this charming 2-bedroom, 2-bath manufactured home ideally located in Osprey’s popular Arbors community. Positioned on a spacious corner lot, this inviting residence features a bright, open layout with the living room flowing naturally into the dining area and kitchen. A standout feature is the beautifully renovated enclosed front porch, complete with hurricane-impact windows—an ideal spot for morning coffee, relaxing, or enjoying the Florida sunshine year-round. The updated light and bright kitchen adds a fresh, clean feel, while a covered one-car carport and convenient storage shed provide practical storage and parking. Residents of The Arbors enjoy an active community lifestyle with a clubhouse, swimming pool, shuffleboard courts, outdoor fitness area, and a variety of social activities. Conveniently located between Sarasota and Venice, you’re close to shopping, dining, entertainment, performing arts, and the Gulf beaches. A great opportunity to enjoy an easygoing Florida lifestyle in a welcoming Osprey community!

145 Edgewood Drive, Osprey

717 Pine Run Dr. Unit 717, Osprey
$159,900
1 Beds ⋅ 1 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Ready for your own slice of Florida paradise? This fully furnished, turnkey one-bedroom condo in Osprey’s Pine Run community is ready to welcome you home. Its second-floor setting offers a charming treehouse feel, surrounded by the community’s lush, natural landscape. Well cared for and thoughtfully updated, this condo features BRAND-NEW A/C (SEPTEMBER 2026), A NEW TANKLESS WATER HEATER (2025), AND A NEW HURRICANE-RATED SLIDING GLASS ENTRY DOOR (2022). Soaring ceilings and three sliding glass doors fill the open living and updated kitchen area with natural light, creating a bright, airy atmosphere. The screened balcony is an inviting spot for morning coffee or relaxing at the end of the day. A carport space directly below the condo provides convenient covered parking, along with an oversized storage closet. Whether you’re purchasing your first Florida home, downsizing, or looking for a winter retreat, this condo offers comfortable, easy living and includes a second sleeping area with a pull out sleeper sofa in the livingroom. Shopping and restaurants are within easy walking distance, with the local favorite Casey Key Fish House and Tiki Bar just down the street, along with the Intracoastal Waterway. Nearby Blackburn Point Park and its boat launch offer even more ways to enjoy the outdoors. Pine Runs’ amenities include pickleball and tennis courts, two pools, a community clubhouse, and a fitness area - all nestled within a lush, natural setting. Come take a look and picture yourself enjoying the Florida Lifestyle!

717 Pine Run Dr. Unit 717, Osprey

7303 Jessie Harbor Drive Unit 7303, Osprey
$449,000
3 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
Welcome to luxury coastal living in this exceptional 3rd-floor penthouse condo nestled in the secluded, resort-style waterfront community of Heron House in Osprey. Offering 1,883 sq. ft. of beautifully light-filled, fully furnished living space, this impressive 3-bedroom, 2-bathroom residence features high-end finishes, warm hardwood floors, plantation shutters, a decorative wood-burning fireplace, and a built-in wet bar perfect for entertaining. The gourmet kitchen is equipped with rich wood cabinetry, granite countertops, stainless steel appliances, and a cozy eat-in breakfast area. Unwind in the expansive primary suite boasting two walk-in closets, a spa-like bath with double vanities, a deep soaking tub, and a separate shower. Step outside onto multiple private balconies to take in tranquil views of lush tropical greenery and calm canal waters—an idyllic setting for outdoor dining or evening cocktails. Located directly on Jessie Harbor with bridge-free, direct access to the Intracoastal Waterway and the Gulf, this gated community offers extraordinary waterfront amenities, including a kayak launch, boat slips (available on a first-come, first-served basis), and frequent visits from local wildlife like otters and dolphins. Residents enjoy a highly active, beautifully maintained HOA complete with a newly installed entrance security gate, heated pool, water aerobics, tennis and pickleball courts, shuffleboard, clubhouse, fitness center, walking trails, locked storage, bike storage, and two assigned covered parking spaces under the building with elevator access. Situated just 10 minutes from Venice Beach, Nokomis Beach, and Casey Key, 20 minutes from world-famous Siesta Key, and minutes from I-75, Oscar Scherer State Park, the Legacy Trail, and Sarasota’s vibrant cultural hub, this hidden gem combines peaceful privacy with unbeatable access to Florida’s finest coastal living.

7303 Jessie Harbor Drive Unit 7303, Osprey

385 N Point Road Unit 401, Osprey
$695,000
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
This exceptional 4th floor end unit is ideally positioned on the coveted south corner of Meridian I, offering a particularly desirable location with no neighboring buildings interrupting the expansive Preserve and water views. Floor-to-ceiling windows showcase the beautiful natural setting and fill the residence with abundant natural light. Featuring 3 bedrooms, 3 baths, plus a formal dining room that can easily serve as a den or home office, the spacious floor plan is equally well suited for everyday living and entertaining. Step directly from your private elevator into a warm and inviting interior, where beautiful cherry wood floors extend throughout most of the residence, adding richness and warmth while complementing the abundant natural light and picturesque views. The generously sized kitchen features white cabinetry and appliances, a breakfast nook and pantry, creating a bright, clean look with plenty of workspace and storage. Both the primary suite and great room open to the large, screened balcony, extending the living space outdoors and providing a wonderful setting to enjoy the peaceful Preserve and water views by day and spectacular sunsets in the evening. Meticulously maintained, the residence includes Hunter Douglas window coverings, a custom entertainment center with electric fireplace, remote-controlled storm shutters along the balcony enclosure, two assigned parking spaces in the covered garage and a private storage unit. Residents of Meridian enjoy a community pool, spa and fitness center, along with all the exceptional amenities of The Oaks Club, including two championship 18-hole golf courses, 12 Har-Tru tennis courts (4 lighted), 4 pickleball courts, the WellFit Center, three onsite restaurants, and an extensive calendar of social and recreational activities. Membership in The Oaks Club is required. There is currently no waiting list for either Golf or Sports/Social membership.

385 N Point Road Unit 401, Osprey

3603 N Point Road Unit 202, Osprey
$629,400
3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code
Virtually Staged. EXCEPTIONALLY SPACIOUS CORNER CONDO – NEARLY 3,200 SF – NO WAITLIST FOR GOLF MEMBERSHIP! Ideally situated behind the gates of the highly sought-after Oaks Preserve, this elegant and beautifully appointed corner residence offers an impressive combination of space, privacy, and resort-style living. The nearly 3,200 SF open floorplan features 3 en-suite bedrooms and 3 baths, providing exceptional comfort and flexibility. Light and bright throughout, the residence showcases crown molding, engineered hardwood flooring, and an expansive kitchen with granite countertops and stainless-steel appliances. Enjoy the serene, private preserve setting from multiple screened balconies, enhanced by convenient remote-controlled automatic hurricane shutters. Additional features include 2 assigned parking spaces, including 1 under-building space, plus climate-controlled storage. A rare opportunity to enjoy substantial living space, privacy, and the exceptional lifestyle of The Oaks! This NEWEST Tower (built in 2007) in the Meridian Condo Complex features Hurricane Impact Windows and Doors and is conveniently located next door to the condo residents’ private Amenity Center featuring Heated Pool & Spa, Fitness Room and outdoor grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished 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. **A MUST SEE**

3603 N Point Road Unit 202, Osprey

1346 Thornapple Drive, Osprey
$540,000
3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code
Welcome to Willowbend, where quiet meandering streets of manicured lawns live, and so can you! Well respected Builder, Lee Wetheringon built sturdy homes and this one will not disappoint! Every bell and whistle upgrade! Open your double stained glass front door to the foyer. Views of a peaceful lake and enormous great room greet you! Double tray ceiling has optional lighting feature and adds layers to the already extra, high quality custom built-ins. Taller doors grace the rooms throughout... Dining room is spacious enough for a large dining table. Convenient custom built-in sideboard for seasonal storage or serving pieces! Great room is 'just that', it's big! Sliding doors open to caged lanai and lakeside views. Kitchen is expansive and has a broom closet and pantry! Southern exposure and extremely high ceilings keep this house light and bright. Breakfast area has 3 panels of aquarium glass windows. Take a peek! But wait, there's much more! The master suite is substantial! More than spacious, it offers a peaceful sitting area also overlooking the lake and lanai. There are two walk-in closets! Double sinks in the master bath, along with a garden tub and water closet. Once again, light and bright! The 3rd bedroom, (has a closet), has been turned into an office! Get a lot of work done here! State of art custom cabinetry! Lovely... Bedroom #2 has its own wing with a full bath. This home has gas in place for the water heater, laundry, etc. The laundry room features a gas Fisher-Paykel laundry set and deep sink! Garage also has lots of storage! Community pool and small clubhouse close by! HOA provides all lawn services, to include care of shrubbery. Conveniently located close to both Sarasota and Venice. Willowbend is a short distance to Nokomis Beach, the wonderful waterfront restaurants off Blackburn Point and Laurel Road, Legacy Bike Trail and Historic Marie Selby Spanish Point! Costco is close and so will be the Trader Joes and Whole Market, both of which are being built! This home is special...

1346 Thornapple Drive, Osprey

33 Bishops Court Road Unit 118, Osprey
$679,000
2 Beds ⋅ 3 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living area entails an inviting great room that opens to serene water views framed by palms and natural greenery while the European-style kitchen is thoughtfully designed with premium SubZero, Wolf and Bosch appliances, modern wood cabinetry, polished granite countertops, and durable ceramic tile flooring—ideal for both everyday living and entertaining. Architectural details add warmth and character throughout, including hand-plastered walls with art niches, graceful archways, plantation shutters, and sisal carpeting. Just off the entry foyer, you’ll find a convenient powder room and a separate laundry room. A private brick balcony provides ample space for outdoor dining or relaxing while enjoying the peaceful surroundings. The primary suite overlooks the lake and includes two walk-in closets and a spacious bathroom featuring dual vanities, walk-in shower, jacuzzi tub and appointed with upscale finishes. The guest suite is equally comfortable, complete with built-in shelving and ample storage. 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 lighted), 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.

33 Bishops Court Road Unit 118, Osprey

23 Siesta Circle W, Osprey
$165,000
2 Beds ⋅ 2 Baths ⋅ Arbors SubDv. ⋅ 34229 Zip Code
Welcome home to this charming fully furnished 2-bedroom, 2-bath mobile home, built in 2001 and located in the friendly and active Arbors Mobile Home Park in beautiful Osprey, Florida. Featuring an inviting open floor plan, this home offers comfortable living spaces filled with natural light from an abundance of windows. Luxury vinyl plank flooring flows throughout the living areas, creating a clean and cohesive look. The kitchen opens seamlessly to the living and dining areas, making entertaining and everyday living easy. The dining room features a built-in buffet with both lower and upper-glass-front cabinets, providing attractive display space and convenient storage. The primary suite includes a single vanity and walk-in shower, while cathedral ceilings add to the home's open and airy feel. An interior laundry area adds everyday convenience. Outside, a charming shed provides additional storage, and the newer carport, added in 2025, offers covered parking. The AC was replaced in 2024 for added peace of mind. Enjoy the Florida lifestyle in The Arbors, a welcoming 55+ community with a variety of amenities and an active social calendar offering plenty of opportunities to meet neighbors and stay involved. Enjoy the clubhouse, swimming pool, shuffleboard courts and fitness area. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community. Come see why so many love calling The Arbors home!

23 Siesta Circle W, Osprey

1328 Thornapple Drive, Osprey
$719,900
3 Beds ⋅ 2 Baths ⋅ Willow Bend SubDv. ⋅ 34229 Zip Code
Virtually Staged. **PRICE IMPROVEMENT BY $30K!** Welcome to your ultimate lakeside maintenance free sanctuary! This home is nestled in a premier community renowned for its top-rated gifted school district & the renowned high quality builder Lee Wetherington. This expanded floor plan in the Willowbend Community offers 2,183 square feet of meticulously designed, sun-drenched living space with high ceilings, crown molding, ceiling fans and window treatments. 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-impacted, 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

2046 Cordes Street, Osprey
$565,000
3 Beds ⋅ 2 Baths ⋅ Cordes Cove SubDv. ⋅ 34229 Zip Code
Virtually Staged. Nature Lovers Paradise! Tucked along a tranquil creek with direct water access to the Gulf of Mexico, this elevated 1,705 sq ft home sits on almost a 12,000 sq ft lot offering the perfect blend of coastal adventure and peaceful natural surroundings. Launch your paddle craft right from the yard and paddle out to open water, or cast a line from your private fishing dock. The fishing here is easy and the setting couldn't be more scenic. The home offers 3 bedrooms and 2 baths, with the primary suite privately situated on the entire second floor featuring a spacious walk-in closet and abundant storage. Downstairs, heart pine flooring flows through the living area, warmed by a cozy wood-burning fireplace on cooler evenings. A screened wraparound porch on the first level extends your living space outdoors, ideal for morning coffee or evening breezes off the creek. This home is ready for your personal touch and is an incredible opportunity to update and build instant equity in a location that can't be replicated. The elevated design offers peace of mind along with sweeping views of the creek and surrounding woods. Outside, the yard is a true nature lover's dream--idyllic and alive with birdsong, from herons to osprey, all just steps from your door.

2046 Cordes Street, Osprey

5100 Jessie Harbor Drive Unit 404, Osprey
$599,000
2 Beds ⋅ 2 Baths ⋅ Blackburn Harbor SubDv. ⋅ 34229 Zip Code
Sweeping water views, beautiful updates and an enviable waterfront lifestyle come together in this exceptional fourth-floor residence at Blackburn Harbor. Docking available on the premises for a very reasonable quarterly fee. Set along South Creek with direct access via canal to the Intracoastal Waterway and the Gulf, this spacious 2-bedroom, 2-bath home with a versatile den captures the essence of coastal Florida living, from spectacular sunsets and gentle sea breezes to easy access for kayaking and boating. Thoughtfully renovated, the residence offers a fresh, modern feel with laminate wood flooring throughout, plantation-style window shutters, updated lighting and new vertical drapery on the sliding doors. The open living and dining areas flow seamlessly to the spacious screened lanai, where expansive water views create a beautiful setting for morning coffee, afternoon relaxation or sunset entertaining. The updated kitchen features quartz countertops and backsplash, stainless-steel appliances replaced in 2022, a new faucet and disposal, and thoughtfully added cabinet drawers for enhanced storage and functionality. Both bathrooms were beautifully updated in 2022 with new cabinetry, sinks, granite countertops, backsplashes, faucets, mirrors and fresh paint. The spacious primary suite enjoys tranquil water views, three closets—including two walk-ins—and a generous ensuite bath. The guest bedroom features a walk-in closet and convenient access to the second bath, creating a comfortable private suite for guests. The den adds valuable flexibility as a home office, reading room or occasional third bedroom. Additional improvements include a new HVAC system in 2023, water heater, washer and dryer in 2022, and a new metal community roof installed in 2025. HOA fees include water, sewer, cable and Wi-Fi, leaving electric as the primary utility expense. Blackburn Harbor is an inviting gated waterfront community surrounded by lush tropical grounds and an active social atmosphere. Residents enjoy a heated pool, fitness center, tennis, pickleball, shuffleboard, clubhouse, walking paths, waterside gathering areas, grills and a kayak launch. Boat dockage is available for approximately $252 per month, offering the rare opportunity to keep your boat close to home and enjoy the waterways at your leisure. Located minutes from Nokomis Beach, the Legacy Trail, Oscar Scherer State Park, shopping and dining, this is a wonderful opportunity to enjoy the best of the Sarasota-area waterfront lifestyle—with the updates already done and nothing left to do but settle in and enjoy.

5100 Jessie Harbor Drive Unit 404, Osprey

299 Turquoise Lane, Osprey
$699,000
3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Remarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled in the Oaks Preserve Neighborhood and offering a maintenance free lifestyle with 24 hour guarded gate. Features include; Beautiful Tray Ceilings, Crown Moldings, Plantation Shutters, Solid Surface Countertops, Tile flooring throughout living spaces, and an Spectacular Owner’s Suite with multiple walk-in closets and sitting area.The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of The Art Fitness Center, Junior Olympic Swimming Pool, Regulation Croquet Court, 4 Pickle Ball Courts, along with numerous dining, social and recreational options. Conveniently located near Florida's top rated Pine View School, the Legacy Bike Trail, and the world renowned beaches of Siesta Key, Casey Key, and so much more. Just a short distance from shops, restaurants, and the cultural offerings of downtown Sarasota. Membership to the club is mandatory. Some images may have been Virtually Staged/Edited...

299 Turquoise Lane, Osprey

1036 Oak Meadow Lane, Osprey
$630,000
4 Beds ⋅ 2 Baths ⋅ Rivendell SubDv. ⋅ 34229 Zip Code
Completely renovated St. Charles floor plan in the highly desirable Woodlands community of Rivendell. You must see to believe the upgrades! Just half a block to the community pool and less than five minutes to the renowned Pine View School for the intellectually gifted.Enjoy stunning brand-new granite countertops in the kitchen and bathrooms, plus beautiful ceramic tile flooring throughout the entire home for easy durability and maintenance. Gain total peace of mind with a new tile roof installed in 2023 and a new air conditioning system from 2024, making this home truly move-in ready. Located just minutes from world-famous Gulf beaches, shopping, and entertainment, this property features low HOA fees and an unbeatable location.

1036 Oak Meadow Lane, Osprey

780 Sarabay Road Unit 16, Osprey
$425,000
2 Beds ⋅ 2 Baths ⋅ Heron Bay Club SubDv. ⋅ 34229 Zip Code
Waterfront Villa w/BOAT SLIPS - Large Private Courtyard & 2- Car Garage - Maintenance Free Living. Single story home-like living. Fish off the Pier or sit on the dock & enjoy the sunsets! NEW DOCK & PIER Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay across from Casey Key. Enjoy carefree coastal living with maintenance-free grounds and an all-inclusive HOA that covers insurance, roof, exterior maintenance, landscaping, roads, pool and tennis facilities, docks/boat slips, cable TV, high-speed internet, water, trash and sewer. This spacious 2-bedroom, 2-bath villa features a versatile bonus room—perfect for a home office, den, or even a guest bedroom. Inside, you'll find a thoughtfully updated interior with a renovated kitchen featuring raised panel maple cabinetry and new countertop, The vaulted-ceiling living room offers tranquil lake views overlooking the bay, with many evenings capped by stunning sunsets over the Bay. STORAGE! in addition to the garage there is an interior attic! Outside, a 587 sqft courtyard with a hot tub invites outdoor relaxation and entertaining and expands the indoor-outdoor living space to 2,161 sqft Community amenities include a heated bayside swimming pool, tennis court, a fishing pier, kayak launch, and dockage for 10 boats—complete with electric and water—available to residents at NO COST. This is a very private location. Located directly on Little Sarasota Bay with no fixed bridges near MIDNIGHT PASS, residents enjoy the highly sought-after Osprey location close to Siesta Key and Sarasota’s rich cultural attractions. Nokomis beach is only a few miles away. Enjoy waterfront dinning at Casey Key Fish House, The Point and Deep Lagoon Oyster House. Highly-rated medical facilities, major airports, and shopping destinations are within close driving distance. You have arrived at your final destination.

780 Sarabay Road Unit 16, Osprey

2309 Jessie Harbor Drive Unit 2402, Osprey
$480,000
3 Beds ⋅ 3 Baths ⋅ Blackburn Harbor Waterfront Villas SubDv. ⋅ 34229 Zip Code
Your screened lanai comes with a front-row seat to the sunset. This second-floor, 3-bedroom, 2.5-bath condo in Blackburn Harbor Waterfront Villas overlooks the canal, boat docks, and green space. Vaulted ceilings in the living, dining, primary suite, and kitchen areas, two sets of sliding glass doors opening to the screened lanai, and side windows keep the 2,006 square feet bright from morning to evening. Canal views carry from the main living and dining areas and into the primary suite, which offers a private lanai slider, dual closets, and an ensuite bath with dual sinks, a jetted garden tub, and a walk-in shower. A spacious second bedroom with its own ensuite bath and walk-in closet gives guests real privacy, and the third bedroom, with French doors, adapts easily as a home office or flex space. Solid wood cabinetry and granite countertops carry through the kitchen and ensuite baths, with newer stainless steel appliances completing the kitchen. The A/C (2016) and water heater (2021) add welcome peace of mind. Two pets are welcome, with a maximum of 30 pounds per pet. This well-maintained, gated, 11-acre waterfront community offers a heated pool, tennis and pickleball courts, BBQ gazebo, kayak storage and launch, and a boat dock rental program (subject to availability), with easy access to the Intracoastal Waterway and the Gulf of Mexico just beyond. Centrally located between Sarasota and Venice, you are minutes from Nokomis Beach, the Legacy Trail, downtown Venice, Oscar Scherer State Park, Sarasota Memorial Hospital Venice Campus, and the dining and shopping along US-41, with I-75 and the 681 connector minutes away as well. The Blackburn Harbor Waterfront Villas HOA fee is $980/month. A rare opportunity to live, entertain, and boat from the same address. Schedule your private showing today.

2309 Jessie Harbor Drive Unit 2402, Osprey

7204 Jessie Harbor Drive Unit 7204, Osprey
$395,000
2 Beds ⋅ 2 Baths ⋅ Heron House SubDv. ⋅ 34229 Zip Code
**BEAUTIFULLY UPDATED WATERFRONT CONDO WEST OF THE TRAIL! BRING YOUR BOAT & KAYAK FOR DIRECT ACCESS TO THE INTRACOASTAL WATERWAY AND GULF OF MEXICO.** Unlike many Blackburn Harbor residences, this thoughtfully renovated 2-bedroom, 2-bath, second-floor condo is move-in ready, allowing the next owner to immediately enjoy the coveted waterfront lifestyle without the time or expense of major updates. The fully renovated interior showcases an impressive kitchen with quartz countertops, solid wood cabinetry, stainless steel appliances, and CoreTec luxury vinyl flooring throughout (except the guest bedroom). The spacious owner's suite features custom built-in closets and cabinetry, complemented by an elegantly updated en-suite bath. Multiple sliding glass doors open to an expansive screened balcony, where peaceful Florida nature views create the perfect setting to relax and unwind. Located within the secure, gated community of Blackburn Harbor, residents enjoy an exceptional waterfront lifestyle with boat docks (subject to availability), kayak launch and storage, direct Intracoastal access, a community pool, tennis and pickleball courts, fitness center, clubhouse, gazebo with BBQ area, and abundant natural surroundings. Private covered parking and ground-level storage are also included. Ideally situated in Osprey between Sarasota and Venice, Blackburn Harbor is just minutes from nationally ranked Pine View School, the Legacy Trail, Gulf beaches, shopping, dining, and everything the Gulf Coast lifestyle has to offer. RECENT COMMUNITY IMPROVEMENTS INCLUDE: Asphalt paving, irrigation, walkways, walkway lighting, and upgraded lighting for the tennis and pickleball courts.

7204 Jessie Harbor Drive Unit 7204, Osprey

116 Woodland Place Unit 116, Osprey
$242,900
2 Beds ⋅ 2 Baths ⋅ Pine Run SubDv. ⋅ 34229 Zip Code
Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such as cabinetry and showers. Enjoy the spacious rooms with the master bedroom having a walk in closet plus another closet. Each bedroom features its own small balcony - perfect for your morning coffee. The lanai off the livingroom will become a focal point for easy living offering a private wooded back yard area. Kitchen features white cabinets with quartz countertops, tile backsplash and stainless steel appliances. A carport plus two exterior storage closets are also nice benefits. The Pine Run neighborhood is an active community offering many activities including pickleball and tennis. There are two pools - the main pool by the club house and fitness center offers gas grills and a scenic view. The second pool is just a short walk from this condo. Kayak storage is available in the neighborhood with a boat and kayak launch just up the street at the Blackburn Point park. This location offers the best of everything. Located between Sarasota and Venice, you are within easy reach of both. Nokomis Beach is 5 miles away, Siesta Key Beach is 9 miles away! The intracoastal waterway is just up the road leading to the ever popular Casey Key Fish House and Tiki Bar. Many other restaurants, shopping and major roads are close at hand. Come see for yourself what makes this condo and Pine Run so special!

116 Woodland Place Unit 116, Osprey

103 Bishops Court Road, Osprey
$699,000
3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. 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.

103 Bishops Court Road, Osprey

280 Hidden Bay Drive Unit 302, Osprey
$745,000
3 Beds ⋅ 2 Baths ⋅ Edgewater At Hidden Bay SubDv. ⋅ 34229 Zip Code
Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity. The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant quartz countertops. Sun-filled living spaces are enhanced by large windows with partial views of Little Sarasota Bay, creating a calm and inviting atmosphere. Well-appointed bedrooms and beautifully finished bathrooms provide comfort and style throughout, with high-end details and a seamless, modern layout. Set in the desirable Edgewater community, this home combines upscale living with easy access to scenic waterways and green spaces—offering the perfect balance of luxury and relaxation.

280 Hidden Bay Drive Unit 302, Osprey

51 Macewen Drive Unit 12, Osprey
$275,000
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

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