Courtesy: PREMIER SOTHEBY'S INTERNATIONAL REALTY
941-364-4000
Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet, and two full baths. The spacious great room includes living and dining areas, elegant crown moldings, tray ceilings, built-ins and plantation shutters for timeless style. The open kitchen offers a breakfast bar, Corian countertops, and a bright breakfast nook with bay windows ideal for casual dining. Go outside to enjoy a large, fenced-in backyard with exotic palm and fruit trees, and a screened-in lanai featuring roll-down sun protection and westerly exposure, ideal for relaxing sunsets or entertaining guests. Recent updates include new roof and paint from July 2023 (transferable warranty) and a new air conditioner in May 2024. Well for irrigation. Woodlands at Rivendell is in Osprey near the top-rated Pine View School, the Legacy Trail, shopping, dining, Casey Key, kayaking, boating, and the beautiful Gulf beaches. In a preferred X flood zone with low HOA dues (only $721 semi-annually), and no CDD fees.
Courtesy: MICHAEL SAUNDERS & COMPANY
941-951-6660
Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 32.5L x 9.7W x 8H. With valet boat service, full-time staff, wash, fuel, and pump-out stations, fish cleaning tables, a bait and tackle shop, maintenance racks, picnic tables, restrooms, an on-site restaurant, deli, and ship store, it's a boater's dream. Call ahead for splash, fueling, and even have your deli order waiting when you arrive. Enjoy quick access to Midnight Pass and the Venice Inlet, along with the peace of mind that comes from hurricane-safe indoor storage that could even reduce your insurance costs. Skip the storm prep, protect your investment, and enjoy effortless boating with first-class service at Osprey Harbor Village.
Courtesy: PREMIER SOTHEBY'S INTERNATIONAL REALTY
941-364-4000
This condominium has it all! Fantastic water views along the Intracoastal. Amazing sunsets from the large balcony. A private two-car garage. Three bedrooms, three full baths and 2,000 square feet of living area. The building has a new roof, the elevator was just replaced, and yet the condo dues were just reduced by $500 a quarter! The spacious screened-in balcony overlooks greenery and the Intracoastal Waterway and offers room for dining and relaxing. The gated resort-style community Hidden Bay offers a heated pool and spa, a grass-thatched tiki hut with grilling stations, a lighted tennis court plus two lighted pickleball courts. For water lovers, there is a kayak launch and a 500-yard elevated boardwalk that winds through lush mangroves. The beautifully renovated clubhouse features a catering kitchen with countertop seating, a fully stocked reading library and a fitness room. The location combines a peaceful, gated waterfront community with convenient access to nearby shopping, dining, recreation and only eight miles to Siesta Key, consistently ranked as one of the best beaches in the U.S. For cycling enthusiasts, the nearby Legacy Trail offers 20-plus miles of scenic, paved biking trails.
Courtesy: COLDWELL BANKER REALTY
941-383-6411
Experience Unmatched Luxury in this Meridian Penthouse! Welcome to the epitome of luxury living at Meridian at The Oaks Preserve. This stunning 3 bedroom, 2.5 bath penthouse offers a private 2-car garage and is designed for the discerning buyer who values quality, elegance, and an unparalleled location. From sunrise to dramatic color-drenched sunsets over the Gulf, your days will be filled with the joy of elegant country club living. The moment you enter, you'll be captivated by the classic appointments and meticulous attention to detail. This expansive 3,700 square foot residence features beautiful Travertine marble floors, inlaid wood paneling, and a private elevator that opens directly into your home. The gourmet kitchen is a home chef's dream, boasting panel-ready appliances, maple cabinets, Miele double ovens, a Thermador induction range, and two Fisher Paykel dishwashers. The spacious master suite is a true sanctuary, featuring a luxurious bathroom with a steam shower, Onex counters, a large, jetted tub and his-and-hers closets. The third bedroom is currently set up as an office and has built-in features. With a soundproof media room, Lutron lightening system, customer millwork and a Sub Zero wine storage system, you’d think you couldn’t ask for more! Yet there is! This unit has a TWO CAR PRIVATE GARAGE, retractable screens on the balcony, and motorized hurricane shutters and, for Meridian residents only, your own community pool, spa and fitness center. Offering all this plus everything that being a member of The Oaks, Sarasota’s finest golf and country club, has to offer: two 18-hole championship golf courses, pickleball and 12 HAR TRU tennis courts, a regulation-size croquet lawn, state-of-the-art Wellfit Center, an inspired culinary program, and celebrated social calendar. Membership is required with homeownership.
Courtesy: LOKATION
954-545-5583
Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.
Courtesy: FINE PROPERTIES
941-782-0000
Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in right away and make some upgrades as needed. YOU and your fellow homeowners will own the company that owns the park. it's a Co-Op park for over-55 owner residents. Therefore, everybody takes pride in keeping it wonderfully maintained and reasonably priced with low HOA dues. Better take a look before the bidding war starts.
Courtesy: GENEROUS PROPERTY
941-275-9399
**STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown moldings, volume ceilings, hardwood floors, wainscoting, plantation shutters, LED lighting accents and MORE! NEW ROOF (2020). The CHEF’s KITCHEN boasts Quartzite counters, hardwood cabinetry, NEW Appliances include SUBZERO Refrigerator, WOLF Range and built-in coffee station, etc. The Spacious primary bedroom suite entails a bonus sitting area and multiple walk-in closets while the primary bath offers dual vanities, elegant soaking tub and custom-tiled shower. Enjoy the utmost in Florida living in the expansive, screened Lanai with impressive pavered deck, ample covered sitting area and oversized, Heated, Saltwater, PebbleTec Pool and Spa. This desirable corner lot in Flood Zone “X” with lovely, manicured, lush landscape offers a tranquil and private setting. The nearby Community Day Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. 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 3 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.
Courtesy: COLDWELL BANKER REALTY
941-493-1000
GREAT NEW PRICE to live like you're on vacation every day in this beautiful one bedroom, one and a half bath, FIRST FLOOR condo in the popular community of Pine Run! Step inside and you'll find a welcoming, well-designed, floor plan that is beautifully decorated throughout. The primary bedroom has a beautiful UPDATED ensuite bathroom with a new hurricane window, dual closets and a private sliding patio door to the back lanai that lets the natural light in. The half bath is also UPDATED and has granite countertops. The UPDATED kitchen has plenty of cabinets for storage, beautiful granite countertops, a pass through counter to the dining area and a new hurricane impact sliding patio door letting in more natural light and opening to a cozy private patio. The screened-in lanai runs almost the entire length of the back of the condo and is a perfect space to enjoy the warm tropical breezes and views of the lush tropical landscaping. Lovely tile flooring in every room. Two pets are welcome here! A/C and water heater new in 2021. Plus you have your own brand new in 2025 stackable washer and dryer inside this unit. This condo comes with a covered one car carport and TWO outdoor storage closets; a perfect place to store your beach chairs and bicycle! Pine Run is a resort-style community in a fabulous location in Osprey with beautiful tropical landscaping and all kinds of amenities to enjoy from the two heated community pools, pickleball and tennis courts, club house with fitness room and outdoor kayak storage racks! During the season there are plenty of fun events to fill up your calendar. Close to Nokomis beach, in a great location between Sarasota and Venice where you will find delicious waterfront restaurants, boutique shoppes, festivals golfing, fishing, boating and more. This wonderful condo is ready right NOW for you to move in, relax and start having fun!
Courtesy: DOUGLAS ELLIMAN
941-867-6199
Newly Remodeled Gulf-Front Mediterranean Villa on Casey Key Framed by the pristine natural beauty of North Casey Key, this Spanish Mediterranean beachfront estate is perfectly positioned along one of Florida’s most exclusive barrier islands — an unspoiled, eight-mile stretch of tropical coastline. Just minutes from the cultural and dining destinations of Venice and Sarasota, the residence offers unrivaled privacy, architectural beauty, and Gulf Coast living beyond compare. Behind a gated entry, the main residence features three bedrooms and three-and-a-half baths, thoughtfully remodeled with no detail spared. Distinctive design elements include wood beams and moldings, Mexican tile and wood floors, brick accents, hand-painted stair tiles, and hurricane-impact windows and doors. Additional enhancements include a new roof, new pool, and updated A/C and pool equipment, ensuring comfort and peace of mind. The gourmet kitchen showcases custom cabinetry, Wolf appliances, and elegant finishes — ideal for entertaining or everyday living. Expansive windows and sliding glass doors bathe the interiors in natural light and frame breathtaking Gulf views. The master suite serves as a private sanctuary featuring a sitting room, wet bar, soaking tub, dual sinks, walk-in closet, and balcony overlooking the pool. Two en suite guest bedrooms provide comfort and privacy for family or visitors. A spiral staircase leads to a rooftop deck offering panoramic Gulf and bay vistas. Reflecting the romance of classic Spanish design, the home radiates warmth and character with arched doorways, pecky cypress ceilings, wrought-iron detailing, and timeless brickwork — blending old-world craftsmanship with modern luxury. The courtyard-style pool area and lush tropical gardens with winding walkways provide a serene setting for outdoor living and entertaining, while the guest quarters above the garage — complete with a full bath — can be used as an art studio, office, or fitness room. Experience the serenity, seclusion, and sophistication of Casey Key — a rare Gulf Coast haven where architectural elegance meets the natural beauty of Florida’s most celebrated barrier island.
Courtesy: PREMIER SOTHEBY'S INTERNATIONAL REALTY
941-364-4000
One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a six-foot depth at mean low tide, the marina can accommodate 175 boats owned by its residents. In Southbay, the HOA fees are only $612 per quarter and it’s also affordable to keep your boat in a slip that includes water and electric. With the Southbay neighborhood in your backyard and the marina in your front yard, this beautiful, completely renovated waterfront home features three bedrooms, four full baths, a flex-space office and it’s on one of only two waterfront streets in the community. The residence, which has stunning views of water from many of its rooms, boasts a tray ceiling inside the front entry, porcelain plank tile flooring, spacious open rooms, an abundance of impact-rated windows and sliding glass doors, a lovely entertainment kitchen that includes a breakfast area, along with spacious family room and dining room areas. The expansive outdoor pool space, with a newly built custom pool and spa, is framed with a panoramic, clear-span pool cage that features an expansive stone-tiled sundeck, along with ample covered areas for outdoor dining and entertaining. The primary suite offers privacy and boasts a double-door entry to the pool and spa. The primary bath features a deep soaking tub, a frameless glass shower, dual vanity sinks, large-format floor and wall tile, and two walk-in custom closets with organization systems. There are two guest bedrooms with en-suites, one with marina views and the other opens to the pool area, and both feature custom reach-in closets. This home is move-in ready with a three-car garage, brick paver driveway and mature landscaping. The home overlooks the Southbay Yacht & Racquet Club Marina, which features a newly renovated clubhouse that offers grand views of the marina. Inside is a 99-person ballroom with a catering kitchen and dance floor, a community room with a kitchen, piano and entertainment area, a fitness room with aerobic and strength training equipment, a card room, library and a meeting room. The community also has a geothermal-heated pool, a youth pool, covered outdoor patios with furniture, three tennis courts, four pickleball courts, a bocce ball court, two shuffleboard courts, a basketball court, a kayak storage area, a waterfront park, 20 acres of common ground and five miles of meandering sidewalks. The development is golf-cart friendly and the community hosts weekly, monthly and multiple annual events, plus there’s even a Power and Sail Club. You’ll love living in this waterfront home and this special community. Be sure to request a copy of the 50-page digital property catalog, along with viewing the property film.
Courtesy: EXP REALTY LLC
800-486-1794
Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and surrounded by lush tropical landscaping, this property offers exceptional privacy and tranquility. This home has been completely renovated and is being sold turnkey. It has been successfully used as an investment property with substantial rental income. Recent updates include: interior renovation, new roof and pool cage rescreened (2021), pool pump (2022), HVAC (2023), water heater, well pump, and garage door opener (2024), plus automated pool cleaner and septic flush (2025). Enjoy the spacious layout, modern finishes, and resort-style outdoor living with a heated pool and screened lanai. The location is ideally situated between downtown Sarasota and Venice, with a short drive to area beaches, parks, restaurants, and shopping. Oscar Scherer State Park is directly across the street, offering birdwatching and nature trails. The Legacy Trail (Osprey Junction Trailhead) is just 3 minutes away, making this a very bike-friendly area. With no HOA and ample parking, you can bring your boat, RV, or other recreational toys-there's plenty of room to store them comfortably on the property. This property is the perfect combination of updated comfort, natural beauty, and an unbeatable location. Ideal as a full-time residence, seasonal retreat, or income-producing investment.
Courtesy: KELLER WILLIAMS ON THE WATER S
941-803-7522
Tranquil Coastal Living in Pine Run 244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown Sarasota. Step inside to discover light-filled spaces, a warm neutral palette, and a welcoming open layout. The kitchen stands out with stainless-steel appliances, a stylish glass backsplash, and playful custom cabinetry that adds personality and character. A cozy breakfast nook sits beside a large window overlooking lush greenery, creating the perfect spot to start your day. The spacious living and dining areas flow naturally toward a screened lanai with vaulted wood ceilings, where you can sip coffee in the morning or unwind at sunset to the sounds of nature. Both bedrooms are roomy and inviting, with the primary suite opening directly to the lanai for that indoor-outdoor lifestyle Florida is famous for. Pine Run offers resort-style amenities in a natural, park-like setting two heated pools, tennis and pickleball courts, a fitness center, clubhouse, and kayak storage. With 20+ acres of native trees, walking trails, and tropical landscaping, this community feels worlds away yet sits moments from Tamiami Trail, dining, marinas, and the Gulf’s turquoise waters. Highlights: • 2 Bedrooms, 2 Bathrooms, 1,325 Sq Ft • Open, light-filled interior with stylish kitchen and breakfast nook • Vaulted, wood-ceiling lanai with peaceful treetop views • Primary suite with private lanai access • Full laundry, ample storage, and designated carport parking • Low-maintenance living with exceptional amenities • Minutes to Nokomis Beach, Casey Key, and downtown Sarasota Live easy. Breathe deep. Welcome home to Pine Run.
Courtesy: WILLIAM RAVEIS REAL ESTATE
941-867-3901
PRICE IMPROVEMENT! This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bathrooms have also been updated. Natural light fills the home through replaced windows and elegant French doors, all of which are provided with hurricane protection for peace of mind. Crown molding and plantation shutters on all windows add a refined touch throughout, and engineered wood flooring enhances the living room and bedrooms, while ceramic tile flooring is featured in the kitchen and cozy family room complete with a charming wood-burning fireplace. Additional highlights include: a spacious utility room with ample cabinet storage, a new roof and fresh exterior paint in 2024 and new A/C system, dishwasher and garbage disposal in 2025. Florida-friendly landscaping with an abundance of fruit trees and native vegetation surrounding the home are perfect for the gardening enthusiast. Southbay Yacht & Racquet is a golf cart community that offers an array of community features and exceptional lifestyle with a recently remodeled 10,000 sq. ft. clubhouse featuring a well equipped fitness center, adjacent swimming pool, and expansive patio. The community-owned marina with residents only boat slips offers direct access to the Intracoastal Waterway with no fixed bridges to hinder your journey to the Gulf. Enjoy a wide range of amenities, including: pickleball and tennis courts, bocce and shuffleboard court, scenic walking and biking paths throughout the community and playground. Ideal location conveniently nestled between downtown Sarasota and downtown Venice, this home is close to top-rated dining, shopping, and entertainment. You’re just a short drive from world-renowned Siesta Key and Nokomis Beach, the Legacy Trail, and the nationally ranked Pine View School. Don’t miss this opportunity to own a beautiful home in one of the Gulf Coast’s most desirable boating communities
Courtesy: MICHAEL SAUNDERS & COMPANY
941-966-8000
One of the largest homes in Bay Oaks Estates, 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 landscaping, 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, 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.
Courtesy: FLATFEE.COM
954-965-3990
Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms. Constructed with concrete block on both floors and encompassing 6,254 square feet under roof, this home was built for strength, safety, and peace of mind. The main living area is elevated to 18 feet, well above flood levels. Inside, you’ll find an open-concept design with soaring 14-foot coffered ceilings, crown molding, and LED lighting. Expansive sliders lead to a private lanai and wraparound balconies to enjoy serene sunrises and glowing sunsets. The kitchen offers a large granite island, ample counter space, and a gallery window framing the water. Each of the three bedrooms features a private ensuite bathroom. The master suite includes three closets, balcony access, and a spa-like bath with jetted tub, dual vanities, makeup desk, and oversized shower. One secondary bedroom also has balcony access. The first level provides space for cars, toys, and storage with hurricane-impact glass throughout. Closed-cell insulation enhances efficiency, and concrete stairs and elevator shaft add durability. The home sustained no damage or flooding during recent hurricanes. The expansive paved patio overlooks canals frequented by manatees and dolphins.
Courtesy: DOUGLAS ELLIMAN
941-867-6199
A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances architectural distinction with thoughtful updates that ensure comfort and livability. An oversized circular drive paved in granite tile leads to a stately double-door entrance. Inside, the foyer sets the tone with soaring ceilings, hand-crafted moldings, chandeliers, and a white onyx floor with marble inserts. Spaces include an oversized living room with dual fireplaces, a crystal chandelier, and multiple sets of French doors opening to the lakefront patio. The dining room, anchored by another fireplace and framed by custom casings and built-in shelving, is ideal for grand entertaining. A domed ceiling sitting room with French doors to the patio adds an intimate space for cocktails or conversation, while the custom bar and wine room, with etched glass cabinetry, stone counters, and display shelving, enhances the home’s appeal for gatherings. The kitchen, completely remodeled in 2019, is a showcase of craftsmanship with UltraKraft® cabinetry, custom soffit lighting, Corian countertops, and a center island with breakfast bar. Luxury appliances include a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, microwave, warming drawer, two KitchenAid dishwashers, and a Frigidaire wine fridge. A butler’s pantry provides additional storage, while the sunny breakfast nook overlooks lush gardens. Family and gathering rooms carry the same sense of scale, with dramatic fireplaces, intricate moldings, and detailed ceiling treatments that flow seamlessly for everyday living or large-scale entertaining. The primary suite is a true retreat with a spacious sitting area, custom closets, and a well-appointed bathroom that was newly remodeled in 2025 with spa-inspired finishes. Three guest suites, each with updated full baths (2021 and 2025), provide privacy and comfort. One is a suite with a bathroom near the laundry room, which offers flexibility for live-in staff or extra accommodation. Outdoors, the home embraces its setting with an open pool, expansive deck, and cabana surrounded by manicured hedges and mature landscaping. The views are equally compelling, with mature gardens and community reflecting pond in the front and sweeping lake vistas in the back. Additional highlights include a three-car garage, refinished hardwood floors (2020), and a new Daikin 5-ton AC system installed in 2022. Ownership at The Oaks Club brings an unmatched lifestyle, with two championship golf courses, tennis and pickleball courts, croquet, a fitness center and spa, three on-site restaurants, and a community dock on Little Sarasota Bay. Elegant yet inviting, 101 Osprey Point Drive stands as a rare opportunity to enjoy lakefront living with resort-style amenities in one of Sarasota’s most established private enclaves.
Courtesy: COLDWELL BANKER REALTY
941-383-6411
Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with leaded glass and step into the light-filled interior. Here you will find everything you need for comfortable Florida living. There is a dedicated home office off the entryway, with plantation shutters and a ceiling fan. The formal dining area features a lovely decorative ceiling, and a beautiful built-in buffet with glass-fronted cabinetry. The great room features another gorgeous piece of built-in furniture; floor to ceiling sliding glass doors connect the screened lanai and this room, making it bright and airy. The open kitchen, with breakfast bar, features beautiful new granite counters, stainless appliances, a chef’s desk, built-in wine and beverage cooler. The adjoining breakfast nook is flooded with natural light that streams through the aquarium window and offers an amazing view over the pool and spa. The master suit is huge and has a sitting area with a built-in window seat and large walk-in closets with glass front storage. The spacious master bedroom has been updated with granite countertops, and features dual sinks, a tub and separate shower and has marble wall accents. The two guest bedrooms are good sized and offer ample closet space. The second bathroom has been tastefully updated with granite counter and marble accents. The 2 car garage, with epoxy floor, is air conditioned with plentiful storage. Situated in the Bishopscourt neighborhood, behind the secure gates of The Oaks Preserve, this beautiful home backs a lush, tropical preserve providing privacy for the sparkling pool and spa. The lanai has two separate areas surrounding the pool. A large, covered area with an outdoor kitchen and ceiling fan, the perfect place for al fresco dining in the shade, and pool and spa area, covered by a cage, allowing for frolicking in the sunshine. Or meet your neighbors for a dip in the Bishopscourt community pool. The Oaks Club amenities include two championship golf courses, an award-winning tennis program, pickle ball and croquet courts, and a state-of-the-art fitness center. With three outstanding restaurants, and a wide variety of social and recreational options, there is no need to look any further than here for the perfect place to enjoy the best of Florida country club living. Club membership is required with homeownership.
Courtesy: FLORIDA HOME TEAM LLC
941-486-0012
PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in Florida, or for anyone looking to downsize without sacrificing comfort or style. Residents enjoy the best of the Florida lifestyle, with close proximity to beautiful beaches-just 2 stoplights away. Additionally, the community is near parks, arts venues, shopping, and restaurants, making it perfect for both active living and peaceful retreat. This home has been thoughtfully updated with new porcelain "wood-look" tile throughout most of the living space, a renovated guest bathroom featuring a walk-in shower, fresh interior paint, and a new roof installed in 2021. The neighborhood is located in one of Sarasota County's top school districts, with Pine View School just a few minutes away. Just a short walk up the street, the community clubhouse offers a generously sized pool, perfect for swimming and social gatherings. Whether you're seeking tranquil relaxation or active outdoor adventures, this exceptional property and community provide the perfect balance. Notice- Some photos of the property have been Virtually Staged.
Courtesy: RE/MAX ALLIANCE GROUP
941-486-8686
One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and entertaining. Elegant tray ceilings, crown molding, and 9-foot ceilings enhance the first floor living space. The flooring is a beautiful wood look tile and LVP throughout the home. Upstairs, you’ll find both bedrooms, including the primary suite with a walk-in closet. As an extra bonus, there is a two-car garage. There is a community pool where you can enjoy a refreshing swim or relax poolside. Venture out to nearby Gulf beaches, shopping, dining, Oscar Sherer State Park and the Legacy Trail. Whether you’re looking for a year-round residence or a seasonal retreat, this home is the perfect fit. Don’t miss this opportunity—schedule your showing today!
Courtesy: OWN SRQ LLC
941-400-4084
One or more photo(s) has been virtually staged. Custom Home located in the exclusive gated community of The Oaks Bayside with a private pool and spa. Just across the street from Sarasota Bay. Recent improvements include updated bathrooms and a newer kitchen (with Thermador appliances) and all freshly painted. This 4 bedroom, 3 bathroom plus bonus room house is in ideal size to maintain while fully enjoying with your family and guests. All rooms overlook the pool area with large windows allowing lots of natural light yet still completely private. The large primary bedroom has two walk-in closets and meanders into a master bath paradise. Large dining room, over-sized two car garage, laundry located next to the kitchen. The Oaks Bayside private security gate and 24-hour guard service. The Oaks has two golf courses; one was designed by Arthur hills and the other designed by Frye Stratka. A 40,000 sq. foot clubhouse offers three outstanding dining venues. Rounding out the resort are twelve HAR-TRU tennis courts, main pool and playground. Membership to Sarasota's finest country club, The Oaks, is available and required with property purchase. The Oaks Club is close to a wealth of natural and cultural amenities, dining and shopping, centers of learning, and a thousand and one ways to enjoy the great outdoors. Make this home yours today! A little TLC will go a long way! Easy to show!
Courtesy: PREMIER SOTHEBY'S INTERNATIONAL REALTY
941-364-4000
This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings, architectural details like arches and insets, sconce lighting, crown molding, tray ceilings and shutters. The layout promotes a refined atmosphere where the subtle color palette, which is newly painted, fosters a seamless transition between indoor and outdoor spaces, ideal for enjoying Florida's unique climate. Stylish den at front of the home while the living and dining areas flow into a spacious family room adjacent to the open kitchen. The kitchen is functional and stylish, equipped with solid wood cabinets, granite, ample storage options and a breakfast room with tranquil pool views. Natural gas cooking for the chef of the residence. A practical entry from the garage leads to a large laundry room that includes additional storage. The owner’s suite is a retreat, featuring dual closets, a separate linen closet, a luxurious walk-in shower, glass brick accents, dual sinks with separate vanities and a relaxing soaker tub. Convenient direct pool access as well. Guests will appreciate the two-bedroom suite with its dedicated hallway and bath, which allows for privacy from the owner’s suite. The community boasts low fees that cover ground maintenance, irrigation, access to the pool and spa, gym facilities, pickleball courts, and high-speed internet and DirecTV streaming. Families will benefit from the nearby top-rated Pine View School, while the Intracoastal Waterway, beautiful beaches, Legacy Trail, shopping, dining, grocery stores, coffee shops and vibrant tiki bars are all just minutes away. New water heater in 2025, Interior freshly painted in 2025, storm shutters on lanai in 2020 and accordion storm shutter on front door.
Courtesy: KELLER WILLIAMS ON THE WATER S
941-803-7522
Attention water lovers... take a look at this home in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball courts, and kayak storage. Residents also enjoy a waterfront park and nearly 20 acres of common grounds with miles of walking trails. A true highlight is the gorgeous geothermal pool, which showcases stunning marina views and is a must-see when visiting Southbay! Now that you’ve fallen in love with the community, are you ready to explore this spectacular home that’s waiting to be yours? This spacious residence, spanning over 3,000 square feet, welcomes you with a brick-paver driveway and lush, mature landscaping along the front walkway. Continue through the gated entry to discover the tranquil sound of a soothing water feature before stepping inside. The interior boasts beautiful views of the pool and lush green landscape, hard flooring throughout, and a layout designed for both everyday living and effortless entertaining. The floor plan includes two distinct family rooms, one with a cozy fireplace, wet bar, and beverage refrigerator, and the other offering beautiful views of the pool. The primary bedroom includes an additional room with pool views, ideal for an office or exercise space...the choice is yours. A spacious laundry room, complete with a double desk and abundant storage, adds to the home’s functionality. Outside, the large lanai features a beautiful pool and provides generous covered areas, and plenty of open space for sunbathing under the clear blue sky. Recent updates include a new roof installed in 2023 and a recently refinished and resurfaced pool. The location is equally appealing, just minutes from a variety of restaurants and shopping, convenient highway access, and the soft, powdery sands of Southwest Florida's Gulf Beaches. I welcome you to visit this home... come see, come sigh, and make it your own!
Courtesy: EXP REALTY LLC
888-883-8509
LIVE THE ULTIMATE COASTAL LIFESTYLE on the coveted Casey Key barrier island at this vibrant 3-bed, 3.5-bath waterfront retreat, perfectly positioned along the Intracoastal Waterway with dazzling, front-row views. Designed for unforgettable days on the water, this home features a stunning Aqua-Tech infinity edge heated pool with therapy jet ledge, where you can unwind while watching boats, jet skis, kayaks, and the occasional dolphin glide by. Set on a generous .49-acre lot with lush tropical landscaping, fresh exterior lighting, brand-new shell driveway, and beautifully re-stained cedar siding (2025), the home blends island charm with modern updates. A shared, deeded boat slip offers quick access to the Intracoastal—perfect for sunset cruises, fishing trips, or lunch runs to nearby waterfront restaurants. Step inside to soaring ceilings and sun-filled living spaces anchored by gorgeous engineered hardwood floors. The open-concept great room flows effortlessly to an expansive composite deck designed for entertaining, complete with multiple lounge zones, a grilling area, and panoramic water views that make every gathering feel like a vacation. The chef's kitchen shines with sleek cabinetry, premium stainless appliances, a dramatic stone island, and a glass tile backsplash. A stylish dry bar with leaded glass barn door adds an extra touch of coastal chic. All three bedrooms with their own private ensuites, while the loft provides flexible space for an office, den, or artist’s perch overlooking the main living area. The metal tile roof provides long-term durability, and the optional HOA (only $400) adds neighborhood security without CDD fees. Enjoy peaceful island living with the convenience of Blue Lagoon Restaurant, Mariner Jack Marina, boat and jet ski rentals, fishing spots, and Sarasota’s vibrant dining and cultural venues just minutes away. Private aviation is close by, making travel effortless. THE SELLER IS HIGHLY MOTIVATED AND OPEN TO SERIOUS OFFERS, making this an exceptional opportunity for buyers looking to secure a foothold on Casey Key. Come experience waterfront living at its most energizing and serene way on one of Florida’s most treasured islands. This is Casey Key—where every day feels like a getaway.
Courtesy: COMPASS FLORIDA LLC
941-279-3630
Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle—enhanced by thoughtful recent updates including a new roof replaced in 2023, fresh interior paint, an updated kitchen, and a beautifully updated pool and jacuzzi. As you arrive, mature tropical landscaping and stately curb appeal immediately set the tone. Step inside to a generously sized home designed for both relaxation and entertaining. Open living areas, large windows, and high ceilings create an airy, welcoming atmosphere, while the refreshed interiors offer a clean, move-in-ready feel. The updated kitchen serves as the heart of the home, providing both style and functionality for everyday living and hosting guests. The interior flows seamlessly into the private outdoor oasis, where the recently updated pool and jacuzzi invite you to enjoy endless days under the Florida sun. Whether hosting friends for a casual barbecue, unwinding with a sunset soak, or enjoying your morning coffee poolside, this space perfectly embodies Florida’s indoor-outdoor lifestyle. Positioned on a corner lot, the home offers exceptional privacy, light, and space—ideal for family gatherings or a peaceful retreat. Spacious bedrooms provide comfort for both owners and guests. A washer and dryer convey with the sale, along with a brand-new pool table, adding both convenience and entertainment value. Life in Southbay Yacht & Racquet Club is more than just owning a home—it’s embracing a lifestyle. Enjoy access to the deep-water marina with Gulf access, tennis and pickleball courts, a vibrant social calendar, fitness amenities, and waterfront strolls. Just minutes away are the pristine beaches of Siesta Key and Nokomis, along with world-class dining and boutique shopping. Here, every day truly feels like vacation.
Courtesy: AUM FLORIDA REAL ESTATE LLC
855-286-3573
Live the quintessential Florida lifestyle at 455 N Shore Drive in Osprey! Located West of the Trail in desirable Sorrento Shores, this beautifully updated 2-bedroom, 2-bath home is perfect for entertaining, relaxing, or as a strong rental investment. Just minutes from Nokomis Beach, Venice Beach, and Siesta Key, residents can also join the Sorrento Shores Marina Association, offering 42 boat slips with direct access to the Intracoastal Waterway and Gulf of Mexico. With an HOA fee of only $95/year and no flood zone designation, it’s a rare value. Inside, enjoy an open-concept living and dining area, spacious kitchen with granite countertops, and utility room with washer and dryer. Upgrades include impact-resistant windows and doors, crown molding, granite baths, new ductwork, fire- and pest-retardant insulation, hurricane-rated garage door, whole-home surge protector, and a brand-new roof with gutters (2024). Outdoor highlights include a paver driveway, screened lanai with hot tub, large patio, and fully fenced backyard with room for a guest house, in-law suite, or ADU. Whether as a full-time residence, seasonal retreat, or rental, this home offers the ultimate Florida coastal lifestyle. Schedule your private showing today at 455 N Shore Drive!
Osprey is located in Florida. Osprey, Florida 34229has a population of 6,395. Osprey 34229 is less family-centric than the surrounding county with 14.92% of the households containing married families with children. The county average for households married with children is 17.15%.
The median household income in Osprey, Florida 34229 is $87,120. The median household income for the surrounding county is $69,490 compared to the national median of $69,021. The median age of people living in Osprey 34229 is 58.3 years.
The average high temperature in July is 90.8 degrees, with an average low temperature in January of 50.7 degrees. The average rainfall is approximately 54.3 inches per year, with 0 inches of snow per year.
