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WILLOWBEND PH 1 - A4687822 - 1348 THORNAPPLE DR, OSPREY, FL 34229 6 Days on yellowkey
$535,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Beautiful lakefront pool home in Willowbend showcases one of the wider, more open water views in the community, framed by an expansive three panel sliding glass door that fills the home with natural light. This three bedroom plus den, two bath residence offers over 2,100 square feet with a functional split floor plan and spacious living areas designed for comfortable everyday living and effortless indoor - outdoor flow. The private screened lanai overlooks the expansive lake and includes a pool, creating a peaceful setting to relax and enjoy Florida’s outdoor lifestyle. Many homes in the community are positioned along narrower sections of the lake, making this view especially appealing. The primary suite offers two walk-in closets, along with a bath featuring both a soaking tub and separate shower. The interior is original and presents an opportunity for a new owner to update and customize to their personal style. Recent improvements include a five year old air conditioning system and one year old water heater. Willowbend is a maintenance-free community with lawn care, landscaping, and irrigation included, conveniently located near the Legacy Trail, Oscar Scherer State Park, Nokomis Beach, and Pine View School. Residents enjoy living in a beautifully established setting surrounded by lakes, preserves, and mature landscaping. Willowbend offers a community pool and spa, tennis and basketball courts, fitness center and playground. This property offers strong value for its location, view, and private pool, and is ready for its next owner to make it their own.
Listing is courtesy of: COLDWELL BANKER REALTY
SOUTHBAY YACHT & RACQUET CLUB - A4688266 - 1527 BUOY LN, OSPREY, FL 34229 8 Days on yellowkey
$1,199,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2026 AC unit, 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large covered outdoor living space overlooking the large lanai with tv, private tanning area, and room to entertain. A split bedroom design, game room with space for billiards table, and separate dining area, and great room surround the private courtyard layout designed to entertain. Ample storage throughout including an air conditioned, secure 12x7 storeroom. Southbay Yacht and Racquet Club offers a clubhouse, tennis, pickleball, basketball, shuffleboard, playground, and low fee, exclusive dockage for residents in the deep water marina. Frequent community activities provide opportunities for an active social atmosphere from cruises to sports.
Listing is courtesy of: BRIGHT REALTY
SOUTHBAY YACHT & RACQUET CLUB - A4688995 - 313 LOOKOUT POINT DR, OSPREY, FL 34229 8 Days on yellowkey
$5,999,999 | Single Family Home | 4 beds | 4.5 baths | 5 gar
Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY
SORRENTO SHORES REP OF 2 - A4688006 - 353 S SHORE DR, OSPREY, FL 34229 14 Days on yellowkey
$1,200,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Welcome to Sorrento Shores—where location, lifestyle, and waterfront living come together beautifully. Perfectly positioned on a generous .36-acre canal-front lot, this 3-bedroom, 2-bath pool home offers direct access to the Intracoastal Waterway just a few homes down the canal. A true boater’s dream, your private dock provides quick and easy access to some of the area’s most beloved waterfront destinations. Cruise north to Casey Key Fish House, or the newly reopened Midnight Pass. You could also head south toward Venice to enjoy Pop's Sunset Grill and Pelican Alley. Spend your days at Snake Island, or venture through the jetties to the open waters of the Gulf of Mexico —where the possibilities for exploration are endless. Inside, the home features a spacious and flexible floorplan with a kitchen, dining room, living room, and den, along with an indoor laundry room. Two of the three bedrooms are private ensuites, offering ideal comfort for guests or multi-generational living. The home is being offered turnkey (with select personal exclusions), making it move-in ready for immediate enjoyment or seasonal use. Step outside to your impressive 27x40 enclosed lanai with pool, creating an expansive outdoor living space perfect for entertaining or unwinding in your own private tropical setting. In addition to the 2-car garage, a large storage shed provides added convenience, and there is dedicated space to park your boat trailer right on the property—no off-site storage needed. Major updates provide peace of mind: New roof (2025) A/C (2018) Sewer pipes lined (2024) Water heater (2024) New pool heater (Dec 2025) Sorrento Shores is a hidden gem offering a voluntary HOA of just $125/year and no CDD fees, delivering a relaxed coastal lifestyle without the burden of high community costs. Whether you’re searching for a winter retreat, full-time residence, or investment opportunity, this property stands out with its rare combination of quick Intracoastal access, expansive lot size, private dock, and prime location.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT.
BAYSIDE - A4687847 - 3936 WAYPOINT AVE, OSPREY, FL 34229 14 Days on yellowkey
$1,039,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Under contract-accepting backup offers. Discover coastal-inspired living at its finest in this exquisite lakefront home nestled within **Bayside**, an exclusive Taylor Morrison-built community of just 49 meticulously landscaped, maintenance-free residences. As you step inside, your eyes are immediately drawn through the expansive great room to breathtaking water views that capture the essence of waterfront living. The great room offers generous space for both elegant entertaining and relaxed everyday enjoyment, enhanced by tray ceilings and elegant crown molding—among the many thoughtful upgrades found throughout the home. The gourmet kitchen is a standout, featuring quartz countertops, a large closet pantry, premium GE Monogram appliances, an LG refrigerator, and a spacious island with counter seating and dual sided cabinets. This space overlooks the lanai and pool, creating a seamless indoor-outdoor flow. Outside, the lanai is truly exceptional—an entertainer’s dream with a fully equipped outdoor kitchen, a cozy gas fireplace, both covered and open seating areas, and a sparkling saltwater pool and spa with gas heater. All of this is beautifully framed by a brand-new 2025 panoramic screen enclosure, offering sweeping views of the lake and abundant wildlife. The primary suite is a private retreat with stunning lake views with a luxurious bath featuring a spacious walk-in shower and a full wall vanity with dual sinks. The expansive walk-in closet includes custom built-ins for maximum storage and organization. A thoughtful split-bedroom plan ensures privacy, with Bedroom 2 offering an ensuite bath, Bedroom 3 conveniently located near the main bath, and a spacious den/office providing flexible living options. Additional practical features include a well-appointed laundry room with ample cabinetry and a garage equipped with its own split HVAC system. Bayside residents enjoy exclusive access to a private waterfront park overlooking the Intracoastal Waterway, with panoramic views of Casey Key and spectacular sunsets. This open space includes a day dock, kayak and paddleboard launch, fire pit, and generous lawn area—perfect for relaxing or gathering with friends. Located west of the trail with direct water access, this rare combination of lifestyle and location is nearly impossible to find. Homes like this don’t last long. Don’t let this one get away!
Listing is courtesy of: RE/MAX ALLIANCE GROUP
OAKS 2 PH 3 - A4687368 - 434 MACEWEN DR, OSPREY, FL 34229 16 Days on yellowkey
$1,465,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Meticulously maintained and updated with care, this 3 bedroom, 3 bath + den/study home in The Oaks Clubside offers beautiful views. A mixture between clean modern lines and cottage chic this house feels cozy. Yet it has an open floor plan, soaring ceilings and every room in the house is light and bright. The formal living room opens to the large lanai and pool with Southern exposure. The view over the lake to the Eagle #6 is simply gorgeous! It is one of the most stunning views in the neighborhood. There is plenty of room to host friends and loved ones. Serve a meal in the formal dining room, have a causal lunch in the kitchen nook or at the breakfast bar, or dine al fresco under the large, covered area overlooking the pool. From the luxurious master suite to the guest bedrooms, this home is beautifully appointed and showcases the finest of details and improvements, including a new roof, impact windows and doors and pretty, updated landscaping. The Oaks, Sarasota’s premier golf and country club, offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center.
RIVENDELL UNIT 5 THE WOODLANDS - A4687161 - 1016 SCHERER WAY, OSPREY, FL 34229 17 Days on yellowkey
$950,000 | Single Family Home | 4 beds | 3.0 baths | 3 gar
Under contract-accepting backup offers. BEAUTIFUL INSIDE and exceptionally well maintained, this Rivendell home offers the kind of upgrades, efficiency, and outdoor living that are becoming increasingly hard to find. This Luxurious home is situated on a large beautifully landscaped, lake front lot with a Southeast Exposure overlooking Oscar Scherer State park! The interior layout is spacious and functional, featuring tile flooring throughout the main living areas and carpet in the bedrooms for comfort. A dedicated front office connects directly to the primary suite, creating a flexible space ideal for working from home, a sitting room, or even a private retreat. High ceilings and an open flow between the living spaces enhance the overall feel, while the home’s condition reflects true pride of ownership. Step outside and the property truly separates itself. The heated pool has been resurfaced with Pebble Tec and features a solar heating system that was just replaced in 2024, providing year-round enjoyment with energy efficiency. The outdoor space is further enhanced with hurricane roll-down protection, an outdoor stereo system, and a removable baby safety fence—offering both entertainment and peace of mind. Major updates have already been handled, including a BRAND NEW ROOF in 2025 with a transferable 20-year warranty and TWO NEW A/C systems installed in 2025. The home also benefits from an irrigation well, helping maintain the lush landscaping while keeping water costs zero. Total electric costs have remained under $2,400 annually for the entire property, showcasing impressive efficiency for a home of this size. Additional features include a mini-split A/C system in the garage paired with an insulated garage door—perfect for a workshop, gym, or climate-controlled space—as well as a large safe that conveys with the sale. Rivendell residents enjoy a well-rounded lifestyle with low HOA fees that include a heated community pool, playground, and scenic recreational trails—all with no CDD fees. The community offers a rare private path directly to Pine View School and borders Oscar Scherer State Park along with over 200 acres of preserved land, creating a unique blend of convenience and natural surroundings. The home is near both Siesta and Nokomis Beaches, Costco, and loads of shopping and restaurants. Home is situated less than a mile from the Legacy Bike Trail. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. This is a rare opportunity to own a move-in-ready home where the major expenses have already been taken care of—offering a combination of condition, upgrades, and outdoor lifestyle that is hard to match. Book your private showing now to see this property for yourself!
OAKS - A4687195 - 448 E MACEWEN DR, OSPREY, FL 34229 18 Days on yellowkey
$2,100,000 | Single Family Home | 4 beds | 3.5 baths
**IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4 BEDROOMS plus a STUDY/DEN, 3 FULL and 1 HALF BATHS. Inside, you’ll find high ceilings, elegant crown molding, a cozy fireplace, plantation shutters, custom built-ins, and rich hardwood flooring throughout. The spacious kitchen is designed for both functionality and style, showcasing granite countertops and black stainless KitchenAid appliances. The expansive primary suite is a true retreat, complete with multiple walk-in closets, dual vanities, a soaking tub, and a custom-tiled shower. Enjoy Florida living at its finest on the screened lanai, featuring a heated pool and spa, travertine marble pool deck, and a large covered entertaining area—all overlooking tranquil golf course and garden views for ultimate privacy. Additional highlights include a 3-car garage and thoughtfully designed indoor-outdoor living spaces perfect for entertaining or relaxing. 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
Listing is courtesy of: GENEROUS PROPERTY
SORRENTO SHORES - N6143587 - 437 S SHORE DR, OSPREY, FL 34229 21 Days on yellowkey
$525,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry about. Discover the possibilities in this home that sits on a generous 19,500 (ALMOST ½ ACRE) square foot lot, providing ample space to stretch out, play, and grow. Step outside and enjoy the expansive, enclosed over-sized lanai and host gatherings all while overlooking your own backyard paradise. Inside, multiple large sliding glass doors effortlessly blend the indoor and outdoor spaces, inviting the sunshine to fill your home. The home features three spacious bedrooms, 2 bathrooms, multiple living spaces, and 2-car attached garage. Recent updates bring peace of mind: NEW ROOF (2025) and HVAC SYSTEM (2025). Also, enjoy the IRRIGATION SYSTEM that runs off a private well to keep your lawn green. This home is also perfectly positioned to enjoy the best local amenities. You’ll find the stunning Oscar Scherer State Park just moments away, offering miles of trails for hiking and birdwatching. The famous Legacy Trail is nearby, ideal for cycling or a leisurely stroll through the scenic landscape. When you're ready to soak up the sun, Nokomis Beach is just a short drive away, perfect for sand, surf, and sunsets. And when it’s time to dine out, you’re surrounded by a variety of waterfront restaurants offering delicious meals with views to match. It’s the ultimate blend of peaceful living and easy access to everything you need for relaxation and adventure.
Listing is courtesy of: EXIT KING REALTY
OAKS 2 PH 2 - A4686927 - 642 TRENTON WAY, OSPREY, FL 34229 21 Days on yellowkey
$2,150,000 | Single Family Home | 4 beds | 4.5 baths
Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically situated on a half-acre corner lot surrounded by beautiful landscaping with views of the lake and the 14th Fairway of the Heron Course. This 4 bedroom residence has 4 full baths, 1 half bath, a formal living room with pool views, a separate formal dining room, and an open gourmet kitchen with gas cooktop, stainless appliances, two wall ovens, a breakfast bar, an adjoining dining area and two pantries. The kitchen opens to an expansive family room overlooking the pool. The spacious master suite features a large luxury bath, two large his-and-hers closets and a lovely sitting area overlooking the pool. All three additional bedrooms are en suite. A dedicated office with built ins and a versatile bonus room/game room adds valuable flexibility for a wide variety of lifestyles. The large and lovely lanai includes an outdoor grill and bar, covered seating, awnings, and a freeform pool and spa overlooking the water and golf course. With a four car garage, abundant storage and numerous updates, including a new roof installed in December 2024 (with warranty), a new pool heater installed in 2024, new central air conditioning (2 units, 2 zones) in 2022, freshly painted interior and exterior, this home is the perfect choice for those who want to live in comfort and luxury. A complete list of updates is available. The mandatory Membership to The Oaks Club will provide everything for living a country club lifestyle; two championship golf courses, tennis and pickleball courts, a regulation croquet lawn, state-of-the-art wellness center and a wide array of dining and social options.
OAKS - A4683382 - 230 OSPREY POINT DR, OSPREY, FL 34229 23 Days on yellowkey
$2,495,000 | Single Family Home | 3 beds | 3.5 baths
Designed by Las Casitas Architects, this Spanish-style residence, featuring 3 bedrooms, 3.5 baths, a den/study with built-in Murphy bed and a 3-car garage, sits on an oversized .59-acre preserve lot with circular drive and courtyard entry. The light-filled, open floorplan features wood and marble flooring, crown molding, tray ceilings, and custom built-ins throughout. The chef’s kitchen is a standout with solid wood cabinetry, granite countertops, a large island with prep sink, counter seating, and premium appliances including Thermador and Bosch. The expansive master suite includes multiple walk-in closets and a luxurious bath with dual vanities and a large custom-tiled shower. Guest bedrooms are generously sized and well-appointed. Enjoy exceptional Florida outdoor living on the spacious screened lanai with heated saltwater pool, outdoor kitchen, and ample covered seating—all overlooking the tranquil North Creek Coastal Preserve. This home is equipped with Control4 automation, Lutron lighting, whole-house water filtration and softener, NEW generator with 500-gallon propane tank, hurricane-impact windows and doors, and two tankless water heaters. A rare combination of quality construction, modern systems, privacy, and natural beauty—this home is truly move-in ready.
OAKS 2 PH 1 - A4686681 - 228 SAINT JAMES PARK, OSPREY, FL 34229 26 Days on yellowkey
$1,695,000 | Single Family Home | 3 beds | 2.5 baths | 2 gar
Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors and gleaming mahogany floors. Extensively improved, the home has been repainted inside and out, with refurbished flooring throughout (including the garage), new carpeting, a newly renovated laundry room, new pool equipment with a saltwater system, a new driveway, updated fencing, and refreshed landscaping. The open kitchen has been updated and offers quartz countertops, Sub-Zero refrigeration, a wine fridge, beverage drawers, custom cabinetry, walk-in pantry and an island that serves as a breakfast bar. The great room opens to the lanai with pool, spa, and golf views. The split plan provides privacy with a remodeled master suite featuring a spa-like bath and custom walk-in closet. The south side includes an en suite guest room and a third bedroom/office with lanai access and golf views. Additional features include a 2-car garage with epoxy floor and storage, plantation shutters, a newer roof (2020), hurricane shades and new Pella bay windows. Saint James Park offers easy access to all of The Oaks Club’s offerings: tennis. Pickleball courts, croquet lawn, a state-of-the are WellFit Center, and golf facilities. Members enjoy a wide variety of dining options and a robust social calendar.
OAKS - A4684805 - 140 SUGAR MILL DR, OSPREY, FL 34229 36 Days on yellowkey
$1,695,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
BEST PRICED 4 BED IN THE OAKS - MAJOR UPDATES ALLOW IMMEDIATE MOVE IN - NO REMODELING NEEDED! FRESH STYLE....FRESH PRICE! Behind the gates of The Oaks - Bayside, this beautifully redesigned estate presents a rare opportunity to enjoy refined country club living at a compelling new value. Updated and thoughtfully improved with designer transitional style - 140 Sugar Mill Drive offers ultimate privacy with lush landscaping, elegant interiors and resort living. Thoughtfully created for refined entertaining and everyday comfort, you'll enjoy 4 bedrooms and 4 full baths - all on one level - within a bright, open floor plan with custom architectural details throughout. The impressive chef’s kitchen is both stylish and functional, featuring Silestone countertops, premium Sub-Zero and Wolf appliances, an expansive island with seating and a striking bar—perfect for hosting gatherings or enjoying relaxed mornings at home. Separate dining and living spaces allow room for dedicated entertaining - making any occasion a treat! The private primary suite is "magazine worthy" - a sublime but peaceful retreat complete with a tremendous walk-in closet, custom built-ins and a beautifully appointed bath showcasing dual vanities, quartz countertops and a seamless walk-in glass shower. The home is truly a split plan - offering privacy with three additional suites - perfect for guests, a study or exercise/hobby room. The home takes every advantage of space and storage - and you'll be the envy of the neighborhood with the "thought of everything" laundry room and spacious garage. Step outside to exceptional outdoor living - designed for year-round Florida enjoyment. The expansive screened lanai features a heated pool and spa, elegant travertine pool deck, turfed yard with putting-green surface (only home in the Oaks) and new remote-controlled hurricane screens. Surrounded by mature, lush landscaping and a privacy wall, you'll feel the design intent for ultimate seclusion and relaxation. The home not only looks beautiful - it's been maintained to provide peace of mind with a newer roof (2021); impact-rated windows & doors (2021); 2 new HVAC units with UV purification (2021); motorized exterior hurricane shutters (2025); air conditioned garage and hurricane doors; 500 gallon propane tank (2022); electrical service panel (2021); rear yard golf turf (2025) and fresh interior & exterior paint. The Oaks - Bayside is a gated neighborhood with a private day dock on Little Sarasota Bay - perfect for launching kayaks or simply enjoying the sunset. The Oaks is one of the region’s most prestigious 24-hour guard-gated country club communities, residents enjoy an extraordinary lifestyle that includes: two championship 18-hole golf courses; three dining options and ballroom; tennis with 12 Har-Tru Hydro-Grid tennis courts; four pickleball courts; croquet lawns; fitness center and Junior Olympic heated pool; bocce, basketball, playground and extensive social opportunities. Perfectly located west of the trail in Osprey, you're just minutes from Sarasota's outstanding dining and cultural offerings, gorgeous beaches, Legacy Trail and Pine View School for the Gifted. A wonderful opportunity to enjoy Florida's ideal county club lifestyle! (Club membership is required with no waitlist at the current time.)
TOWNS-END SHORES - A4684679 - 1795 HIGHLAND RD, OSPREY, FL 34229 39 Days on yellowkey
$385,000 | Single Family Home | 3 beds | 3.0 baths | 1 gar
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1,500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living. Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home. Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, NEW ROOF 2026 with 10 year warranty! NO FLOOD ZONE — meaning flood insurance is not required. Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease. The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions. Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one. Schedule your private showing today and experience the possibilities this unique property offers.
PARK TRACE ESTATES - A4685004 - 408 PARK TRACE BLVD, OSPREY, FL 34229 41 Days on yellowkey
$625,000 Reduced | Single Family Home | 3 beds | 3.0 baths | 2 gar
Welcome to your own private oasis in Park Trace Estates, a stunning 3-bedroom, 3-bath single-family home overlooking water with unobstructed views of the Legacy Trail and Oscar Scherer State Park. Located in a desirable community minutes from Pine View School, healthcare, and beaches, this residence is perfectly designed for indoor-outdoor living. The heart of the home is a beautiful central courtyard with a saltwater pool, around which the main living spaces are thoughtfully arranged. An en-suite guest bedroom with private courtyard access provides a secluded retreat perfect for visitors. The open-concept interior flows seamlessly from the kitchen, complete with a signature royal blue Hestan refrigerator, into an inviting living room ideal for entertaining. From there, step out to a screened patio overlooking the water to relax in total comfort. The spacious master suite features dual California Closets, a luxurious remodeled bathroom, and an adjoining room that serves as a private office or reading nook. Throughout the home, plantation shutters provide elegant light control and privacy. The property is finished with a side-entry two-car garage featuring custom California Closets storage and a Tesla charger. Positioned just steps from the pristine Legacy Trail for biking and recreation, this home provides the perfect combination of style and lifestyle. Home is available fully furnished. The home is exceptionally well-maintained, featuring a high-efficiency HVAC system (New AC 2017/Air Handler 2020) with a programmable thermostat, a central vacuum system, and an artistic hidden TV in the living room. Recent kitchen and laundry upgrades include a 2018 washer and dryer alongside newer appliances (2020–2022). The private courtyard is equally impressive, boasting a new pool screen (2022), new pool equipment (2024), and an Endless Pool Fastlane feature for a premium fitness experience. Property is located in Flood Zone X (flood insurance generally not required).
Listing is courtesy of: PREFERRED SHORE LLC
BAYSIDE - A4684834 - 14401 MASTHEAD DR, OSPREY, FL 34229 41 Days on yellowkey
$3,250,000 | Single Family Home | 3 beds | 3.5 baths
Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.
SORRENTO SHORES - A4684009 - 447 N SHORE DR, OSPREY, FL 34229 41 Days on yellowkey
$515,350 Reduced | Single Family Home | 3 beds | 2.0 baths | 1 gar
Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr warranty), septic, central air, impact windows and doors (with the exception of the Florida room), updated electrical panel, irrigation equipment, soffits, water heater, impact garage door, pavers, and beautifully redesigned kitchen and baths. Luxury vinyl plank flooring runs throughout, complemented by fresh paint and abundant natural light. The split floor plan provides privacy, while the open living spaces make everyday living and entertaining effortless. The kitchen is both functional and inviting, featuring shaker cabinetry, quartzite countertops, stainless steel appliances, a generous island, and a charming coffee bar that flows seamlessly into the family room and dinette. One of the standout features is the 336-square-foot air-conditioned sunroom with pocket sliders — incredible flex space for a home office, gym, playroom, or second living area — all overlooking the expansive backyard. The screened lanai and paver patio create easy indoor-outdoor living year-round. The only real decision left? Whether you’ll sip coffee on the welcoming front porch as neighbors pass by or unwind in your private backyard oasis listening to the whispering waves. Sorrento Shores is just minutes from Nokomis Beach (4 miles) and Venice Beach (6.5 miles), close to Oscar Scherer State Park and the Legacy Trail (1.5 miles), near the renowned Pine View School (2.9 miles), with convenient access to I-75, historic City of Venice (5.5 miles) and vibrant downtown Sarasota (12 miles). Here, functional updates, classic charm, location and lifestyle all come together — schedule your showing today!
SORRENTO SHORES - N6143210 - 107 SORRENTO DR, OSPREY, FL 34229 42 Days on yellowkey
$425,000 Reduced | Single Family Home | 2 beds | 2.0 baths | 2 gar
This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from the living room, dining room, kitchen and primary bedroom to a spacious screened porch that overlooks a scenic pond and expansive yard. Whether entertaining guests or enjoying a quiet morning coffee, the outdoor living space extends your home beautifully. The kitchen is stylish and functional, offering gently used stainless KitchenAid Gallery appliances, space-saving self-closing cabinetry, and a generous open breakfast bar ideal for casual dining and gathering. Baths have been tastefully modernized with updated cabinets, countertops, fixtures and lighting. Major improvements provide peace of mind, including 2025 sewer pipes relined, a 2022 air-conditioning system, 2015 re-roof, 2015 hurricane-impact windows, 2015 gutters plus interior and exterior paint, and refreshed landscaping. Additional highlights include a two-car attached garage, dedicated workshop space and access to boat docks (Contact HOA for details). Ideally West of the Trail between Sarasota and Venice, with convenient access to Highway 681 and Interstate 75, this home places you close to everything. Top-rated schools nearby include Pine View School for gifted and Venice High School, known for strong sports and arts programs. Outdoor enthusiasts will love being just 5 to 10 minutes from Nokomis Beach, Blackburn Point Park kayak and boat launch, Oscar Scherer State Park, offering hiking, camping, cycling, kayaking, boating and fishing, and the Legacy Trail, which is ideal for biking with family or friends. Dining options abound, including waterfront favorites nearby. This is Florida living at its finest, with modern design, natural beauty, boating access and an unbeatable location.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY
THE OAKS CLUB - A4684136 - 480 ORISKANY CT, OSPREY, FL 34229 44 Days on yellowkey
$1,599,000 Reduced | Single Family Home | 3 beds | 3.5 baths | 3 gar
Tucked away on a quiet street within the prestigious Oaks Club, this elegant residence overlooks the fairway of the Heron 14. This is a rare opportunity to find a home on a premium golf course lot and have the additional privacy of a preserve view across the street. Designed by Toll Brothers, this meticulous 3 bedroom; plus den home offers gracious, entertaining and comfortable everyday living. A well -appointed kitchen opens seamlessly to a family gathering areas, creating an effortless flow for hosting family and friends. Step outdoors to your private oasis and serene dream backyard. A new roof and pool cage (2023) have been added. Living in the Oaks Club means enjoying two championship golf courses,12 har-tru tennis courts, pickleball courts, gorgeous croquet lawns fitness amenities which Junior Olympic size heated pool and an active social calendar- all just minutes away from the cultural vibrancy of downtown Sarasota and the Gulf Coast's world renowned Siesta Beach. Membership in the Oaks Club, Sarasota's premier golf and Country club is required for home ownership.
RIVENDELL - N6143162 - 819 SHADOW BAY WAY, OSPREY, FL 34229 44 Days on yellowkey
$615,000 Reduced | Single Family Home | 4 beds | 2.0 baths | 2 gar
Welcome to this stunning 2,145 square foot pool home in the premier community of Rivendell where maintenance-free living meets tropical elegance. Positioned on a beautifully landscaped corner lot, this meticulously maintained residence offers timeless style and thoughtful updates throughout. Recent improvements include 2026 irrigation valves, 2025 roof replacement, 2024 pool pump and a 2017 air conditioning system, providing peace of mind for years to come. Go onto the inviting front porch, the ideal setting for morning coffee. Enter through the elegant glass front door into a bright, open foyer filled with natural light. The spacious split floor plan seamlessly connects the great room, formal dining room, kitchen, and cafe, creating an ideal layout for everyday living and entertaining. The chef’s kitchen is beautifully updated with granite countertops, stainless steel appliances, custom wine racks, rich cabinetry, a built-in desk, pantry and breakfast bar. The adjacent cafe features a stunning aquarium window overlooking the sparkling heated pool, an ideal spot for casual meals before heading to the beach. The generous primary suite is a private retreat, offering dual walk-in closets, sliding glass doors to the lanai, and a luxurious en-suite bath complete with solid wood cabinetry, granite countertops, dual sinks, a soaking garden tub, walk-in shower, linen closet, and private water closet. On opposite side of the home, guests will enjoy their own private wing with two bedrooms and a full bath separated by a pocket door. The third bedroom features built-in cabinetry and offers wonderful flexibility, easily functioning as an additional office, study, or peaceful reading retreat. The fourth bedroom at front of the home is suited as a den, office or playroom. The spacious laundry room offers a utility sink, additional cabinetry and ample storage. Outdoor living shines in the screened lanai and beautifully updated paver pool area. The fenced area is ideal for pets, and the expansive patio provides a backdrop for relaxing or hosting gatherings. Rivendell residents enjoy low HOA fees that include lawn and shrub care, a heated community pool, playground and scenic recreational trails all with no CDD fees. The irrigation system is connected to a private well, providing an efficient and cost-effective way to maintain the lush tropical landscaping year-round. This neighborhood offers a private path to Pine View School for the Gifted and borders Oscar Scherer State Park and 200 acres of preserved land. Outdoor enthusiasts will appreciate easy access to the Legacy Trail. Ideally in south Sarasota, this serene enclave offers convenient access to pristine Gulf beaches and sits between Sarasota and Venice for exceptional dining, shopping and cultural attractions. Furnishings are available for purchase!
ACREAGE & UNREC - N6143043 - 854 N CASEY KEY RD, OSPREY, FL 34229 48 Days on yellowkey
$4,750,000 | Single Family Home | 4 beds | 4.0 baths
On the quiet and coveted stretch of North Casey Key, where century-old oaks meet the shoreline, and the land unfolds uninterrupted from Gulf to bay, this extraordinary 1.5-acre estate offers a rare opportunity to steward one of the island’s most incredible homesites. With 180 feet of private Gulf frontage and exceptional depth across to the intercoastal, the property is defined by its scale, privacy, and quiet permanence—offering a setting that feels both expansive and deeply secluded beneath a canopy of mature coastal forest. Here, the rhythm of the water and the natural beauty of the land create an environment that cannot be replicated. The existing improvements include a Gulf-facing main residence, originally constructed in the early 1970s, thoughtfully positioned to capture sweeping views in both directions. The two-bedroom, two-bath home features elevated ceilings, expansive windows, and a sunlit central courtyard designed to bring light and the surrounding landscape into everyday living. A separate guest house, completed in 2002, provides two additional bedrooms and baths, bamboo flooring, Bahama shutters, a versatile bonus room, and an oversized two-car garage—offering flexible accommodations for guests, or interim use while renovating or building. A recently installed private dock completes the property’s rare Gulf-to-Bay lifestyle and provides immediate access to boating and waterfront recreation. While the existing structures offer renovation potential and immediate livability, the true and enduring value lies in the land itself. Homesites of this magnitude—spanning Gulf to bay with this level of frontage, privacy, and natural beauty—are rarely available. Conceptual plans by Potter Homes envision a timeless coastal estate exceeding 6,500 square feet under air, thoughtfully designed to preserve the character of the land while capturing panoramic water views and creating a residence of lasting architectural significance. Whether preserved, renovated, or reimagined entirely, this is more than a homesite—it is the foundation for one of Casey Key’s next great estates, and an opportunity to create something that will endure for generations.
Listing is courtesy of: POTTER TRINITY
SOUTHBAY YACHT & RACQUET CLUB - A4683702 - 1471 SHOAL WAY, OSPREY, FL 34229 51 Days on yellowkey
$1,499,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
One or more photo(s) has been virtually staged. This exceptional residence truly checks every box. Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the end of a quiet cul-de-sac and overlooking an expansive green space, the property feels even more open and serene. No expense has been spared in the home’s extensive upgrades, evident the moment you step inside. Eight-inch wide white oak flooring, custom cabinetry, and high-level quartz countertops create a refined yet inviting aesthetic throughout. A striking, oversized fireplace crafted from natural coral stone anchors the living space and is beautifully framed by solid iron double doors—an architectural feature unique to this home. The layout is equally impressive, offering two distinct living areas, four bedrooms, and three baths, thoughtfully designed to maximize both functionality and flow. The oversized garage includes a workshop area and a climate controlled storage space! With every detail already complete, this home allows you to fully enjoy the idyllic waterfront lifestyle Southbay is known for—whether boating, playing pickleball or tennis, or simply relaxing poolside. Boating in Southbay is made easy with its marina located in the center of the development. Peace of mind comes standard with a metal roof designed to resemble barrel tile, hurricane-rated windows, and a location outside of the flood zone, offering both resilience and long-term value. Pack your bathing suit and bring your boat – live the Florida lifestyle to the fullest. Exclusions: mounted tv/screens, potted plants Pool heater conveys as is
Listing is courtesy of: DALTON WADE INC
WILLOWBEND PH 2 - A4681662 - 664 CRANE PRAIRIE WAY, OSPREY, FL 34229 54 Days on yellowkey
$887,000 Reduced | Single Family Home | 3 beds | 3.0 baths | 3 gar
It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wetherington-built Paloma floorplan designed to the highest standards, offering spectacular views and seamless indoor-outdoor living. On one of the community’s most desirable lots, it features unobstructed shimmering views of a wide lake and the natural beauty of the park, creating an extraordinary backdrop for an exceptional lifestyle. The idyllic setting includes a sparkling heated pool and spa. Summer kitchen has sink and stainless beverage refrigerator with large bar entertaining area. The exterior boasts a three-car garage and a double-door that welcomes you into an inviting, spacious interior. The home’s open floor plan includes living/dining with views to the natural beauty, tile on diagonal, crown molding and vaulted ceilings. Handsome office/den to the front of residence. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, including built-in gas range and custom hood. Large walk-in pantry with oversized adjacent laundry room that has an additional deep closet. Dinette area features an aquarium window to take in the natural beauty. Family room is spacious with a corner pocket door that opens wide to let in Florida’s finest weather. The primary suite offers bamboo wood floors, double-tray ceiling and sitting area with French doors. California-style walk-in closets and a luxurious bath with dual sinks, a tub, walk-in shower and separate toilet. Each guest bedroom is generous in size with full bath in between. Additionally, it is a bonus living space with wood floors overlooking the serene setting. Third bath serves as pool bath. On a practical note, new water heater in 2026 and pool pump in December 2025. An amazing lifestyle awaits, all overlooking serene waterfront views teeming with wildlife such as eagles, osprey, otters, turtles and deer. The home is ideally near downtown Venice, Sarasota, Siesta Key, Nokomis Beach and Legacy Trail, offering easy access to cultural attractions, shopping, dining and recreational activities. Short distance to nationally ranked Pine View School. The community’s low fees include internet, Direct TV streaming, yard maintenance, irrigation, pool and spa, gym and pickleball, making this a harmony of luxury, comfort and stunning beauty.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY
OAKS 2 PH 4-C PT 3 - A4683029 - 530 N MAC EWEN DR, OSPREY, FL 34229 54 Days on yellowkey
$2,400,000 | Single Family Home | 4 beds | 5.5 baths
Under contract-accepting backup offers. Located in the prestigious gated community of The Oaks Golf & Country Club in Osprey (Sarasota area), this elegant single-story residence at 530 N Mac Ewen Drive offers resort-style living with championship golf just steps away. Spanning 4,346 square feet under air and 5,837 square feet under roof on an oversized lot, the home features 4 bedrooms, 5 full bathrooms, 1 half bathroom, and a 3-car garage with built-in cabinets and the bonus of a car lift allowing for 4 cars in total. Presented fully furnished and turnkey, this meticulously maintained home is move-in ready and showcases exceptional craftsmanship throughout. Italian granite flows through the interiors, complemented by designer lighting and a whole-house water softener/filtration system. The custom handcrafted kitchen is a chef’s dream, complete with a hidden pantry, soft-close drawers and doors, spice drawers, double oven, and premium Viking Pro appliances. A custom built-in wet bar with ice machine and pull-outs adds convenience for entertaining, while a panoramic electric fireplace anchors the living spaces. A built-in sound system throughout the home and custom closets in every bedroom (including a Therma Sol steam shower in the primary suite) enhance daily comfort. Additional practical luxuries include a bolted-in safe. Step outside to an expansive lanai and backyard oasis featuring a custom-designed pool and hot tub with fire feature, plus a fully equipped outdoor kitchen—perfect for al fresco dining and year-round enjoyment. Industrial-grade landscape lighting (valued at $40K) beautifully illuminates the mature, oversized lot. Residents of The Oaks enjoy 24/7 gated security and world-class amenities including two 18-hole championship golf courses, tennis courts, pickleball, a state-of-the-art fitness center, and vibrant social events. This turnkey luxury home in one of Sarasota County’s most sought-after private communities is an exceptional opportunity for discerning buyers seeking refined coastal Florida living. Roof is 2017 (Tile) and A/C is newer (2023)
Listing is courtesy of: LPT REALTY, LLC
BISHOPSCOURT AT THE OAKS PRESERVE - A4681468 - 156 BISHOPSCOURT RD, OSPREY, FL 34229 67 Days on yellowkey
$1,299,000 | Single Family Home | 3 beds | 3.5 baths | 2 gar
This stunning three-bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. This charming Cape Cod sets the stage for comfortable, gracious living, enjoying private preserve views. A Sonos sound system plays throughout this gorgeous home! Sit back and enjoy a peaceful afternoons and twilight dinners on the lovely newly screened Florida room. There is an additional private rooftop outdoor deck (732 sq.ft.) accessed directly from the second floor living and recreation rooms. Recent renovations in 2023 include two main floor bathrooms with exquisite high-end decorator wall tiles, as well as Italian floor tiles. Premium glass enclosures complement the premium fixtures. The spectacular master bathroom features an elegant standalone bathtub situated under a glass skylight for that Wow factor! The powder room has also been completely renovated and features shiplap accents. The laundry room features new ceramic tile floors, newer washer and dryer, extensive shiplap walls, and a sliding barn door for the generous pantry. Additional features include crown molding throughout the ground floor and in the elegant, wainscoted dining and living areas. The bedrooms have newer ceiling fans, and the master bedroom has an oversize 52-inch decorator windmill fan, just beautiful! The living room, with an enhanced whitewashed fireplace and large screen TV with surround sound, is the perfect space for relaxing or entertaining family and friends. The living room doors open to the Florida room that gives view to the secluded outdoor patio and pool area surrounded by the pristine preserve. The pool has undergone extensive updates, including a new heat pump pool heater and new filtration system. The second floor has a new flat roof (2025), installed by Curry Roofing and includes a warranty. Premium decorator light fixtures have been installed in the dining room, kitchen, and foyer. The entire exterior was painted in August 2025. This charming home, with its private setting on a double lot at the end of a cul-de-sac, is the perfect Florida retreat. Situated in the Oaks Preserve, Bishops Court features include 24 hour guarded gate access, and lawn and landscape maintenance with irrigation. Bishops Court residents can take advantage of the amenities of The Oaks Club, Sarasota's premier golf and country club. Membership, either social or golf, is required with the with home ownership. The Oaks Club has two distinctly unique 18-hole championship golf courses, 12 hartru lit tennis courts, croquet, and pickle ball courts. There is a state-of-the-art fitness center, fine and casual dining options, and many social events for you to enjoy the seasons at The Oaks.