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$685,000
4 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv.
Stunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in the heart of Osprey, showcasing over $250,000 in high-end upgrades. Every detail has been thoughtfully curated, beginning with the spectacular gourmet kitchen featuring an 11-foot quartz waterfall island with abundant storage, Bosch appliances including an induction cooktop and counter-depth refrigerator, 42-inch white shaker cabinetry, wet bar, and wine cooler. The expansive living area impresses with approximately 15-foot vaulted ceilings and a dramatic 15-foot custom built-in fireplace. Both bathrooms have been luxuriously remodeled with floor-to-ceiling tile, rainfall showers with modern glass enclosures, floating vanities, upgraded shower fixtures with handheld sprayers, Kohler toilets, Bluetooth smart fans with built-in speakers, ambient lighting, and a free-standing soaking tub. The primary suite features a sleek barn door, and interior pocket doors have been updated throughout. The fourth bedroom, currently used as an office, features 12-foot ceilings and a custom Murphy bed with an integrated, tailor-made IKEA PAX closet system. Durable, stylish LVP flooring runs throughout the home. Step outside to your brand-new 36' x 12' saltwater pool and spa (completed in 2024) featuring a sun shelf, heating and cooling system, top-of-the-line Jandy equipment, variable-speed pump, and sandblasted marble decking. Pre-installed footers allow for a future pool cage if desired. Maintaining a lush, "envy-of-the-neighborhood" lawn is effortless and cost-effective thanks to the private irrigation well, which has been completely overhauled with brand-new wiring, new pipes, and new sprinkler heads. Significant structural and mechanical upgrades include a new AC system in 2018, updated CPVC plumbing, LED can lighting, and multiple hurricane-impact upgrades, including the front, pool bath, and garage side doors. The air conditioned garage has an upgraded side mount garage opener with smart video door bell, plus a premium impact-rated garage door. All openings except windows have been storm-reinforced. The property is fully enclosed with white vinyl fencing and offers an irrigation well for low-cost landscape watering. This meticulously renovated residence blends modern luxury, functionality, and exceptional craftsmanship; offering a truly move-in-ready home just moments from the highly desired Legacy Trail, perfect for biking, walking, and outdoor recreation.

597 Oak River Court, Osprey/Nokomis
$665,000
3 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv.
Step into your dream home in the sought-after Bay Oaks Estates where comfort, functionality and location come together in perfect harmony. From the moment you arrive, you'll be captivated by the curb appeal and the welcoming presence that instantly feels like home. Beautifully designed, this split-plan residence offers space, style and seamless flow. The double-door entry opens into a foyer, flanked by a formal dining area and a dedicated office. At the heart of the home lies the updated kitchen, with custom solid wood cabinetry, granite countertops, a glass tile backsplash, stainless steel appliances, and a spacious eat-in area with open sightlines to the great room. Oversized sliding doors lead to your private outdoor oasis with a gorgeous new heated saltwater pool and spa on a large, screened lanai that’s a perfect space for relaxing or hosting family and friends. Fully fenced-in backyard, plus the property backs up to a lush nature preserve and the Legacy Trail for a serene backdrop. The primary suite features walk-in closets and a generously-sized updated bath with dual vanities, a soaking tub, separate shower and stylish finishes that elevate your daily routines. Additional highlights include ample natural light, a new garage door with opener in 2025, newer roof, AC and hot water heater. While the home itself is a sanctuary, you’re also in a quiet well-maintained community, just minutes away from world-renowned Siesta Key Beach, historic downtown Venice, the Legacy Bike Trail, countless shopping and dining options and so much more.

563 Pine Ranch East Road, Osprey/Nokomis
$625,000
3 Beds ⋅ 3 Baths ⋅ Bay Oaks Estates SubDv.
Discover this beautifully maintained 3-bedroom, 2-bathroom home nestled in a peaceful, private community just steps from the scenic Legacy Trail. Surrounded by mature trees and vibrant birdlife, this property offers the perfect blend of tranquility and convenience. Step inside to a spacious split floor plan featuring luxury vinyl plank flooring, crown molding, 5½” baseboards, and granite countertops in the kitchen and bathrooms.. The home is also equipped with a tankless propane water heater and a new A/C system installed just 1.5 years ago. Entertain with ease in the expansive lanai or take a dip in the resurfaced pool (2021), surrounded by new pavers and energy-efficient LED lighting. The backyard offers ample space and privacy, making it ideal for gatherings or relaxing evenings. The roof, in excellent condition, was replaced in 2016. Located just 2 miles from the Gulf of Mexico, this home is a short drive to Nokomis Beach, Siesta Key, Casey Key, and a nearby inlet perfect for kayaking or jet skiing. Enjoy proximity to shopping, dining, and top-rated schools including Laurel Nokomis, Venice High, and the renowned Pine View School. Oscar Scherer State Park is also nearby for nature enthusiasts. Schedule your Showing today!

594 Pine Ranch East Road, Osprey/Nokomis
$620,000
3 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv.
Virtually Staged. Back on the market due to buyer financing. Move-in ready Bay Oaks pool home featuring a beautifully renovated kitchen, stunning spa-inspired primary bath, updated flooring, and a huge private fenced backyard. Situated on an oversized 0.38-acre corner lot, this home offers the perfect combination of modern updates, privacy, and outdoor living. Welcome to this thoughtfully renovated pool home in sought-after Bay Oaks Estates, perfectly positioned on an oversized 0.38-acre corner lot in the heart of Osprey. Featuring 3 bedrooms plus a dedicated office, 10-foot ceilings, a huge fenced backyard, and extensive modern updates throughout, this move-in-ready residence offers a rare blend of style, comfort, and effortless indoor-outdoor living. One of the home’s standout features is the oversized fenced backyard, offering a rare combination of space, privacy, and flexibility. The screened lanai, private pool, and expansive outdoor area create the perfect setting for entertaining and year-round enjoyment. Framed by mature landscaping and a newer concrete tile roof (2021), the home creates a welcoming first impression from the moment you arrive. A large driveway and covered parking area provide abundant convenience. New flooring throughout (2025), brand new electrical panel, updated lighting, fresh interior paint, and carefully selected finishes create a clean, cohesive modern aesthetic rarely found in the neighborhood. Inside — 10-foot ceilings, abundant natural light, and a thoughtfully designed layout create an elevated sense of space and openness. Smart-home features include an ecobee thermostat, keypad entry, and a Samsung all-in-one smart washer and dryer. At the center of the home, the fully remodeled kitchen combines style and function with granite countertops, white shaker cabinetry, stainless steel appliances, modern finishes, and an expansive breakfast bar that opens seamlessly to the main living areas. The spacious primary suite serves as a true retreat with two walk-in closets and a beautifully remodeled bath featuring quartz countertops, dual vanities, a freestanding soaking tub, and a frameless glass walk-in shower. Perfectly positioned between The Oaks Club and Stoneybrook Golf & Country Club, Bay Oaks offers the feel of luxury golf-course living without the fees. Families will especially appreciate being just 3 miles from Pine View School, consistently ranked among the top public schools in the nation. Just 6 miles from Siesta Key and 4 miles from Casey Key, this prime Osprey location places you near marinas, golf courses, the Legacy Trail, shopping, dining, and Sarasota’s coastal lifestyle.

619 Oak River Court, Osprey/Nokomis
$620,000
5 Beds ⋅ 3 Baths ⋅ Bay Oaks Estates SubDv.
One of the largest homes in Bay Oaks Estates, with the second-largest floor plan in the community, this 5-bedroom, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush, well-established landscaping highlighted by a mature magnolia and fragrant gardenias, and a covered, columned entry with French double doors and an arched transom. Inside, high ceilings and an abundance of natural light set a welcoming tone. The formal living and dining rooms flow to the heart of the home – a well-appointed kitchen designed for everyday living and entertaining, featuring granite counters, tile backsplash, stainless appliances, a center island with raised breakfast bar, closet pantry, built-in desk and wine rack, recessed & pendant lighting, and a picturesque breakfast nook with wraparound windows. The kitchen opens to the spacious family room with a tray ceiling and mirrored media niche. A pocketing three-panel slider seamlessly extends the living space to the covered lanai and screened pool; additional sliders from the formal living room, the primary suite, and a secondary bedroom maintain the indoor–outdoor connection. Out back, the lanai enjoys a private, tranquil, tree-lined backdrop accented by a mature starfruit tree, overlooking a curved, free-form pool with twin arc fountain jets, a raised sun terrace for lounging, and generous space to relax or gather. A screen door leads to the lawn and a separate pergola patio with power – perfect for morning coffee or an evening grill. From the backyard you have direct access to the Legacy Trail, the popular paved, multi-use path linking Sarasota and Venice, for miles of biking and walking through nature. The private primary retreat offers lanai access, two closets (one walk-in), and a spa-like en-suite bath with a Jacuzzi jetted soaking tub framed by an arched window with plantation shutters, separate walk-in shower with wall body sprays, a long double vanity, and a private water closet. Thoughtful split-bedroom design places three secondary bedrooms and a full bath together in their own wing (one is oversized with lanai access that can flex as a game/media space), while a full 5th bedroom – currently used as an office – sits near the primary suite. An interior laundry room adds storage shelves, cabinets, and a utility sink. Major updates for peace of mind include: replumbed water lines, roof (2015), A/C (2019), new water heater (2024), new pool pump (2024), kitchen appliances (2021), washer and dryer (2023), polycarbonate storm panels, and irrigation. All in a well-kept, low-fee, pet-friendly Osprey community conveniently located just minutes from top-rated schools, including the prestigious Pine View School, and close to the Gulf beaches of world-renowned Siesta Key, Nokomis, and Venice, as well as Oscar Scherer State Park, and a variety of shopping, dining, entertainment, and everyday conveniences; the Gulf Coast lifestyle at its finest. Schedule your private showing today and fall in love with the lifestyle that 571 Pine Ranch East Rd has to offer.

571 Pine Ranch East Road, Osprey/Nokomis
$540,000
4 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv.
Welcome home to this beautifully maintained 3-bedroom + den, 2-bath pool home nestled on a desirable corner lot, in a cul-de-sac, in Osprey. This home has been impeccably maintained and is an unbeatable location, this is the effortless Florida lifestyle you've been searching for. Peace of mind comes standard here. The roof is less than 7 years old, the AC was replaced just 2½ years ago, and the hot water heater is under 3 years old... meaning the big-ticket items are already handled, so you can simply move in and enjoy. You will find vinyl plank flooring, tile and carpet throughout. The care and attention put into this home shows in every corner. This home offers space to rest, work, entertain and relax...The flexible den offers the perfect home office, creative studio, 4th bedroom or guest retreat, whatever your lifestyle calls for? along with two spacious bathrooms. Then, step outside to your private screened pool, where the corner lot provides extra breathing room, privacy, and that open, airy feel that's so rare to find. Positioned in the heart of Osprey, this home is only minutes from the beloved Legacy Trail? which is ideal for cycling, jogging, and morning walks through some of Florida's most scenic natural surroundings. Nature lovers will also enjoy the proximity to Oscar Scherer State Park, offering kayaking, wildlife watching, and over 15 miles of trails. And when the beach calls, it's answered quickly. Nokomis Beach is just a short drive away for a casual sunset stroll, while the world-famous Siesta Key Beach, home to some of the whitest, finest sand on the planet, is within easy reach for those perfect beach excursions. 523 Oak Bay Drive checks every box: updated systems, private pool, flexible living space, and access to the very best of Florida's Gulf Coast. People also love the access to top-rated schools, including the nationally acclaimed Pine View School and Laurel Nokomis Elementary, making this the complete package for anyone looking to plant roots in one of Sarasota County's most sought-after communities. Homes like this don't last long. Schedule your private showing today.

523 Oak Bay Drive, Osprey/Nokomis
$540,000
4 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv.
One or more photo(s) has been virtually staged. WELCOME HOME!! THERE HAS BEEN NO FLOODING OR DAMAGE FROM RECENT STORMS!! RECENTLY APPRAISED at $560,000!! This is a Beautiful and Spacious 4 bed/2 bath Home in the Community of Bay Oaks Estates. It is just a Short Drive to 3 different Gorgeous Beaches including Nokomis Beach, Venice Beach and the World Famous Siesta Key! Easy Access to Tamiami Trail and I-75, Just Minutes away from Major Shopping Areas, Restaurants, City Parks, and The Popular Legacy Trail (biking/walking trail). When you walk in the front door you are greeted by a Large Living Area with High Ceilings. The Sliding Glass Doors lead you out to a Large 10x26 ft Covered and Screened Lanai with a Fully Fenced Back Yard that looks into a Heavily Wooded Preserve for Privacy. There are Tile Floors throughout the Entire House. The Master Suite has a Large Shower and Separate Garden Tub for Soaking your Cares Away. The Kitchen has Newer Stainless Steel Appliances from 2020 and lots of Counter Space. ROOF (2016). AC (2022). WATER HEATER (2020). NEW PAINT on the Interior. Whole House Water Filtration System installed by Water World in September 2023 The filter doesn’t need to be changed for 10 years! The House was RE-PLUMBED in 2016! The Laundry Room is inside under AC and has it's own Wash Sink. This Home is Perfect for Entertaining Guests. There is NO CDD and a LOW HOA FEE of only $270 PER YEAR. Bay Oaks is a Small, Quiet, Well Maintained Community where homes Rarely come available. It's Truly a Hidden Gem located in the Highly Desirable Osprey Area. Make an appointment to see it Today!

813 Oak Pond Drive, Osprey/Nokomis
$520,000
3 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv.
Seller is motivated! Welcome to Bay Oaks Estates—your quiet Florida retreat! This 3-bed, 2-bath + den home offers a true indoor-outdoor lifestyle with a private pool featuring a beautiful ocean-inspired mosaic. With no houses in front and none behind, you’ll appreciate the peace and privacy. Enjoy cozy winter nights with your wood-burning fireplace, and peace of mind with a new roof (2022) and newer water heater. You’re only 10 minutes from Siesta Key and Nokomis Beach and just steps from the Legacy Trail for biking and jogging. Shopping and dining are all close by as well! If you’ve been searching for a spacious pool home in a secluded neighborhood—this one checks all the boxes.

566 Oak Bay Drive, Osprey/Nokomis
$511,500
3 Beds ⋅ 3 Baths ⋅ Bay Oaks Estates SubDv.
Virtually Staged. Beautiful home in the desirable Bay Oaks neighborhood, known for its winding roads, mature landscaping, and minimal traffic. Perfectly situated between The Oaks Golf Course and Stoneybrook Golf & Country Club, this home offers the lifestyle and views without the high price tag or association fees. The property welcomes you with a circular driveway, new roof (2018), fenced yard, and freshly pressure-washed exterior(2026) with updated landscaping (2026). Double French doors open to a grand foyer with soaring ceilings and immediate views of the family room, pool, and backyard, creating a Florida grand entrance. The entire interior of the home was repainted (2026). A dedicated office with French doors and a formal dining room, both overlook the front yard. The spacious primary suite features new porcelain tile flooring, two walk-in closets, and pocket sliders that open to the newly rescreened lanai (2026), perfect for enjoying stunning west coast sunsets year-round. The primary bathroom includes a new double-sink vanity, a private water closet with a pocket door, and a separate tub and shower. The kitchen offers a built-in pantry, space for a breakfast table, and uniquely angled countertops and bar that maximize outdoor views. Enjoy peekaboo views of The Oaks golf course through the third set of sliding glass doors and corner windows. The second living area continues the vaulted ceilings and is filled with southwest-facing natural light. An updated half bath with direct pool access adds convenience. A pocket door separates the split floor plan, leading to two additional bedrooms and a full bathroom with tub/shower combo, new vanity, and porcelain flooring. At the heart of the home is the covered and newly rescreened lanai. The recently refinished pool (2025) pool pump (2026) with water features, completed by award-winning Platinum Pools, create a relaxed setting. The fenced backyard offers privacy, with the option to open up more golf course views at the owner’s request (through The Oaks Club and at no additional expense). Additional features include an interior laundry room with a sink, located just off the two-car garage with refinished floors (2026), an exterior access door, and whole house replumbed (2018). This home offers a highly functional layout, with many major updates already completed for peace of mind and quick move-in, while still allowing room for your personal touch. Located just 6 miles from Siesta Key (#1 beach in America), 4 miles to Casey Key, and close to multiple local marinas, golf courses, and the Legacy Trail. Also conveniently located near major shopping, including Costco, grocery stores, pharmacies, pet stores, restaurants, Starbucks, and Nordstrom Rack, as well as an upcoming development featuring Whole Foods, Chipotle, Sprouts, and more. This is a home you need to experience in person. Schedule your private showing today!

562 Oak Bay Drive, Osprey/Nokomis