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34229 - A4695211 - 4212 EXPEDITION WAY, OSPREY, FL 34229 1 Day on yellowkey
$2,390 | Townhouse | 3 beds | 2.0 baths | 1 gar
The property is available for rent starting JULY 1,2026. IMMACULATE, FURNISHED , POOL AND PALM TREES VIEW** Welcome to life in paradise! Here's your best opportunity yet! TURN-KEY FURNISHED "Ibis" floor plan at desirable Bay Street Village!This charming Florida condo is perfect for anyone seeking a full-time residence. This 3 Bedroom/2 Bathroom, modern, second story condo is impressive! The OPEN CONCEPT offers a spacious feel, yet the split bedroom design allows for privacy when your guests are visiting. Quality features include designer kitchen with great quality cabinets, granite counters, IMPACT windows, tile roofs, paver driveways, and solid BLOCK construction. Picture yourself at the RESORT STYLE POOL... or Relaxing on your SCREENED LANAI overlooking the pool and palm trees. Water and Sewer included in the very reasonable monthly rent. Bay Street Village is a maintenance-free gated community that includes a resort-style heated pool, fitness room, and club room. Close to shopping, dining, beaches, and and A+ Pine View School, a Niche, National, Top Ranked.! Easy access to 41 and I-75. Bay Street Village is also a Pet friendly community and is located directly across from the NEW Bay Street Dog Park and Bay Street Park/Playground. Schedule your showing today!!!
Listing is courtesy of: DALTON WADE INC (888-668-8283)Listing Agent: Claudia Dybala (773-318-5796)
34229 - A4694878 - 157 LOOKOUT POINT DR, OSPREY, FL 34229 2 Days on yellowkey
$875,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
This one is an impressive little gem located in sought after Southbay Yacht & Racquet Club. So many improvements, upgrades and updates all you need to do is bring your furniture and move right in. As we approach the hurricane season, you will enjoy the sense of security provided by the replacement of all windows, sliders and doors with hurricane impact glass. A secluded back yard retreat awaits you with a spacious covered lanai looking onto the updated heated self draining pool and the wooded back yard. Some of the home highlights are: UPDATED KITCHEN AND BATHS, PORCELAIN TILE IN THE MAIN LIVING AREAS, IMPACT WINDOWS ABOUT 11-12 YEARS AGO. The owners have continued with the updates including: NEW METAL ROOF 2023, REPLACED MAIN ELECTRICAL PANEL AND ADDED 220 OUTLET FOR FUTURE GENERATOR. ADDED WHOLE HOUSE AIR PURIFICATION 2022, NEW EPOXY GARAGE FLOOR 2020, A/C AND HEAT PUMP SYSTEM 2018, REPLACED 3 DOORS WITH IMPACT GLASS, REPLACED 3 SLIDING GLASS DOORS WITH IMPACT GLASS 2015, COMPLETE POOL AND LANAI RENOVATION INCLUDING HEAT PUMP AND DECK PAVERS 2017, REPLACED GARAGE DOOR WITH IMPACT RESISTANT DOOR AND VENTS. REPLACED APPLIANCES: MICROWAVE 2025, REFRIGERATOR AND WINE COOLER 2024, RANGE, WASHER, DISHWASHER, 2023, HOT WATER HEATER 2023, REPLACED CARPET WITH CERAMIC TILE 2021 AND CUSTOM PLANTATION SHUTTERS THROUGHOUT THE HOUSE. There are more items I haven’t mentioned but you need to come take a look for yourself. There is a detailed list of improvements available. The Southbay community has much to offer! One of the few neighborhoods with its own exclusive marina. Dock space is only available to residents and is offered at very reasonable rates and can accommodate almost any size boat. Southbay is an active community with many clubs and gatherings at the remodeled clubhouse overlooking the marina. The clubhouse features two kitchens, ballroom, fitness center, card room, even a “livingroom” with grand piano. There’s something for everyone! Pickleball courts, tennis courts, bocce ball, community pool, playground, kayak launch and storage. Southbay is also a golf cart community! The Southbay location is in easy reach of shopping, grocery stores, restaurants, main roads, downtown Sarasota and downtown Venice. Local beaches including Nokomis (5 miles away), Siesta Key (10 miles away), Venice (7 miles) are all within an easy drive. Local restaurants including the famous Casey Key Fish House and Tiki bar are close at hand. Come and see what makes this home and Southbay so special!
Listing is courtesy of: PAT WILLIAMS REALTY, LLC (941-289-6231)Listing Agent: Pat Williams (941-289-6231)
34229 - A4694716 - 101 OSPREY POINT DR, OSPREY, FL 34229 4 Days on yellowkey
$4,790,000 | Single Family Home | 4 beds | 5.5 baths | 3 gar
Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)Listing Agent: Joel Schemmel (941-587-4894)
34229 - A4694515 - 292 TURQUOISE LN, OSPREY, FL 34229 4 Days on yellowkey
$1,050,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
This stunning, updated home sits on a corner lot; the largest in Emerald Woods. Located behind the gates of The Oaks Preserve, this maintenance free residence features 3 bedrooms, 2 baths and a 2-car air conditioned garage along with premium finishes throughout. The updated kitchen, equipped with high-end stainless steel appliances, will delight any home chef. The spacious master suite includes a luxurious master bath, walk-in closets, and a sitting area with sliders to the lanai and pool. The expansive outdoor living area is designed for relaxation and entertaining, showcasing an impressive pool and spa, a new outdoor kitchen, new automated hurricane shutters and a view of a tranquil pond. Additional updates include a new roof, hurricane impact PGT windows and sliding doors, new quartz countertops throughout, a water softening and purification system and built-ins in the 3rd bedroom currently used as a combined study/bedroom. Residents of The Oaks enjoy unmatched amenities including two 18-hole championship golf courses, an award-winning tennis program, pickleball courts, a state-of-the-art fitness center and a junior Olympic, community pool as well as a celebrated social calendar, and incredible dining options.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)Listing Agent: Steve Abbe (941-400-3969)
34229 - TB8510971 - 314 S SHORE DR, OSPREY, FL 34229 5 Days on yellowkey
$1,649,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Rare Gulf-access waterfront opportunity in desirable Sorrento Shores in Osprey. This spacious residence is set on a generous 0.54-acre waterfront lot with a private dock, screened pool, outdoor kitchen/grill area, paver patio, mature landscaping, and peaceful canal views. The home offers 3 bedrooms, 3 full baths, 3,853 sq ft, and a large flex room currently used as a studio with possible 4th bedroom potential. The open ranch-style layout includes comfortable living, dining, and entertaining spaces filled with natural light. The updated kitchen and bar area feature Viking Professional double ovens, a Viking Professional gas stove, Sub-Zero refrigerator, newer dishwasher, and microwave. Additional spaces include a private office with built-in cabinetry, large flex room, and an air-conditioned tackle/hobby/storage room with an additional Sub-Zero refrigerator. Major system updates noted by seller include a newer roof, full-house generator, impact windows and doors, two AC systems, new central vacuum system, tankless water heater, fireplace, and propane service for the grill, stove, dryer, fireplace, tankless water heater, and full house generator. Located near Casey Key, Nokomis Beach, Venice, Sarasota, marinas, dining, shopping, golf, parks, and coastal amenities. Property is being sold As-Is with right to inspect. Seller exclusions include seller’s personal property, all potted plants, and the backyard swing.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)Listing Agent: Jonathan Minerick (888-400-2513)
34229 - A4694435 - 89 NAVIGATION CIR, OSPREY, FL 34229 8 Days on yellowkey
$345,000 | Condo | 2 beds | 2.0 baths | 1 gar
One or more photo(s) has been virtually staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of relaxation, comfort, and everyday convenience. From the moment you walk through the door, the tranquil pond views immediately draw your attention, creating a sense of calm that carries throughout the home. Imagine starting your mornings on the screened lanai with coffee in hand, overlooking the sparkling water feature while enjoying the warm Florida breeze and peaceful surroundings. With over 1,400 square feet of thoughtfully designed living space, this beautifully maintained 2-bedroom, 2-bathroom condo also features a versatile den, separate laundry room, and attached one-car garage. Rare first-floor units with water views and this level of convenience are highly desirable for full-time residents, seasonal owners, and investors alike. The open-concept floor plan was designed to maximize both comfort and entertaining. The kitchen showcases granite countertops, solid wood cabinetry, stainless steel appliances, stylish backsplash details, a spacious island, and breakfast bar seating that flows seamlessly into the bright and inviting living area. Crown molding, modern lighting, fresh neutral paint, and updated flooring throughout elevate the home with a clean and timeless feel. The spacious primary suite serves as a private retreat featuring peaceful water views, a large walk-in closet, linen closet, and an updated en-suite bathroom complete with dual sinks and a custom walk-in tile shower. A generously sized guest bedroom, beautiful guest bath, and flexible bonus room provide endless possibilities for guests, a home office, hobby space, or additional lounge area. Bay Street Village offers true maintenance-free living with resort-style amenities including a sparkling pool, fitness center, clubhouse, and beautifully maintained grounds. Centrally located between Sarasota and Venice, residents enjoy quick access to world-renowned Gulf beaches including, Nokomis Beach, and Venice Beach, along with downtown Sarasota, marinas, waterfront dining, shopping, golf, entertainment, Sarasota Bay, the Legacy Trail, and countless local restaurants and attractions. Located near the nationally recognized Pine View School and tucked away from the heavy tourist traffic while still remaining close to everything, this condo offers the perfect combination of convenience, comfort, and the relaxed coastal lifestyle that everyone dream about when moving to Florida. Whether you are searching for a primary residence, seasonal escape, or investment opportunity, this exceptional waterfront condo delivers location, lifestyle, and value all in one. Schedule your private showing today and experience firsthand why this hidden gem in Bay Street Village is the perfect place to call home.
Listing is courtesy of: KW COASTAL LIVING II (941-556-0500)Listing Agent: Jozefina Wells (941-993-3051)
34229 - A4694468 - 103 BISHOPS COURT RD, OSPREY, FL 34229 8 Days on yellowkey
$749,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)Listing Agent: Mark Lyda (941-586-2670)
34229 - A4691622 - 4424 CONCHFISH LN, OSPREY, FL 34229 10 Days on yellowkey
$615,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Situated in the highly sought-after community of Palms at Casey Key, this beautifully maintained 2017-built home offers the perfect blend of comfort, style, and location. With low HOA fees and no CDD fees, this property delivers exceptional value in one of Osprey’s most desirable areas. From the moment you arrive, the paver driveway and lush tropical landscaping create a warm and welcoming first impression. Inside, the home opens to a bright and airy great room where tray ceilings and expansive triple-panel sliding glass doors allow natural light to pour in, creating an effortless connection between indoor and outdoor living. Designed with both everyday living and entertaining in mind, the kitchen serves as the heart of the home with a large center island offering ample seating, white cabinetry, stainless steel appliances, and a spacious corner pantry for additional storage. The thoughtfully designed split-bedroom floor plan offers privacy and comfort, while the owner’s suite feels like a relaxing retreat with tray ceilings, a large walk-in closet, dual vanities, and a walk-in glass shower. Step outside to your private patio overlooking the in-ground spa — the perfect place to unwind after a beach day, enjoy a quiet evening under the stars, or cool off during warm Florida afternoons. Location is everything, and this home truly delivers. Ideally situated just minutes from nationally ranked Pine View School, less than a mile from the Casey Key boat launch and waterfront tiki bar, and only about 15 minutes to both Nokomis Beach and Siesta Key Beach, you’ll enjoy easy access to some of the area’s best boating, dining, shopping, golf, parks, and coastal lifestyle amenities. Whether you're looking for a full-time residence or the perfect Florida retreat, this home offers the lifestyle so many buyers are searching for.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)Listing Agent: Ashley Wallace (941-302-2586)
34229 - N6144418 - 341 BAYSHORE DR, OSPREY, FL 34229 10 Days on yellowkey
$3,200 | Single Family Home | 3 beds | 2.0 baths | 2 gar
This fully renovated classic-style residence blends Old Florida charm with modern finishes and spacious living areas throughout. Featuring 3 Bedrooms and 2 Bathrooms, the home offers a functional layout designed for comfort and privacy. Conveniently located near Blackburn Boat Ramp with plenty of on-site parking. Just under 1900 sqft of living space, the kitchen flows seamlessly into the dining and living areas, creating an ideal space for everyday living and entertaining. A rear door leads to a fenced yard with ample space for boat parking. Two Guest Bedrooms are located on the first floor and are nicely situated to the Guest Bathroom that features a walk-in shower. The expansive Primary Suite occupies the second floor that features a walk-in closet and access to the spacious balcony. The private Master Bathroom is equipped a large soaking tub, dual vanities, and a walk-in shower. Additional features include a private 2-car garage, generous storage space, and a peaceful patio area perfect for relaxing outdoors. Ideally located just 15 minutes from Siesta Beach, Nokomis Beach, and Historic Downtown Venice, residents enjoy convenient access to shopping, dining, entertainment, and some of the Gulf Coast’s most desirable beaches. This property offers a unique opportunity to enjoy Florida living in a highly sought-after and private community. ~Included in rent: Lawn Care. ~Pets: a Small Dog under 35lbs is considered.
Listing is courtesy of: COMPASS PROPERTY MANAGEMENT LLC (941-444-6185)Listing Agent: Jeremy Myers (941-444-6185)
34229 - A4692331 - 619 OAK RIVER CT, OSPREY, FL 34229 16 Days on yellowkey
$609,900 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. 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), 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.
Listing is courtesy of: FISHMAN GROUP REALTY LLC (763-443-1761)Listing Agent: Ross Fishman (763-443-1761)
34229 - N6144313 - 272 FOUR KNOT LN, OSPREY, FL 34229 17 Days on yellowkey
$1,095,000 | Single Family Home | 5 beds | 3.0 baths | 2 gar
Under contract-accepting backup offers. Welcome to this simply stunning, meticulously maintained 5-bedroom, 3-bath residence located in the highly sought-after Southbay Yacht & Racquet Club. Proudly offered by the original owner, this exceptional home showcases true pride of ownership throughout. Situated on a beautifully treed and lushly landscaped lot, the property offers privacy, elegance, and outstanding outdoor living. The sparkling inground pool and brand-new 2025 pool cage create the perfect setting for entertaining or relaxing in your own tropical retreat. The expansive lanai features gorgeous 24x24 pavers and enhanced outdoor electrical lighting for unforgettable evenings outdoors. Inside, the home has been thoughtfully updated with a beautifully renovated kitchen with custom tile work, double ovens, quartz countertops. All that bathrooms have been updated also. Hurricane-impact windows and doors have all been replaced, providing peace of mind and energy efficiency. Additional upgrades include new flooring, a new roof in 2025, updated house wiring and electrical service panel in 2019, and a complete camera security system. A unique bonus feature is the fully equipped caterer’s kitchen located in the garage — ideal for entertaining, large gatherings, or serious cooking enthusiasts. This home combines timeless care, extensive updates, and resort-style living in one of the area's premier boating communities that features tennis courts, clubhouse, pickleball courts, deep water marina, kayak storage and much more! This is a rare opportunity to own a meticulously maintained and beautifully upgraded home in one of the area’s most desirable waterfront communities.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)Listing Agent: Andrew Peterson (716-316-3145)
34229 - A4693374 - 347 BAYSHORE DR, OSPREY, FL 34229 18 Days on yellowkey
$739,000 | Single Family Home | 3 beds | 2.5 baths | 4 gar
This is your chance to live West of the Trail in the coveted Bay Acres community. This waterfront community has no deed restrictions so you can keep your boat or golf cart right on your property. With over 1400 Sq. Ft. of GARAGE SPACE the possibilities are endless here- use for your 4 plus antique cars, storage , recreational vehicles or jet skis. Part of the garage is air conditioned. The garage plus living space is over 4,000 Sq. Ft. The home itself has many nice features including a very nice large kitchen, dining room with tray ceiling, floors are gorgeous real Hardwood and wide planked. This custom built home has impact windows, a metal roof, a large covered porch, and a fenced back yard. Bay Acres has a waterfront park with boat slips that can be rented for a small yearly fee, Kayak storage and a kayak launch to be out in the Gulf waters in minutes. This home is ideally located right around the corner from the public Blackburn Point Boat Ramp, within minutes of many waterfront restaurants, and just 11 miles up the road is Downtown Sarasota. Come see why this friendly neighborhood and home can make your dreams a reality.
Listing is courtesy of: COLDWELL BANKER REALTY (941-739-6777)Listing Agent: Sharon Sprow (813-817-9931)
34229 - A4692490 - 320 TROPIC DR, OSPREY, FL 34229 19 Days on yellowkey
$195,000 | Manufactured Home | 2 beds | 2.0 baths | 1 car
One or more photo(s) has been virtually staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an existing beautiful gazebo and lighting. The possibilities are endless as this space can be kept for leisure or used to build an additional home. The seller invested $28,000 in fundamental upgrades, includin g: New subflooring and moisture barrier, Laminate flooring throughout main living areas and bathrooms, and Fresh carpeting in bedrooms and the Florida Room. The interior features an open floor plan with two bedrooms. The primary suite includes dual walk-in closets and a ensuite bath. This home is light and bright with a comfortable Florida Room—perfect for morning coffee or evening relaxation. A large outdoor shed offers abundant storage and includes a washer and dryer. This desirable lot is located in the pet-friendly section of the park. Monthly dues include an impressive list of amenities: access to the clubhouse, heated community pool, lawn service, water, garbage pickup, sewer, cable TV, and internet. The Seller recently spent $28,000 on a new sub floor, new moisture barrier, New laminate flooring in kitchen, dining, great room, bathrooms, and hallway. New carpet in both bedrooms and Florida room. There’s even an on-site storage area for your boats, RVs, or kayaks for a small fee! The location is unbeatable—close to Casey Key, the Legacy Trail, Walmart, shopping, restaurants and the Nokomis and Siesta Key Beaches. You’re also just a short drive from historic downtown Venice and the lively attractions of downtown Sarasota. The community also offers an active clubhouse, heated pool, dog run, shuffleboard, exercise area, and regular social events.
Listing is courtesy of: RE/MAX PALM (941-929-9090)Listing Agent: Susan Retzke (941-544-5558)
34229 - A4693277 - 260 HIDDEN BAY DR #401, OSPREY, FL 34229 19 Days on yellowkey
$4,850 | Condo | 3 beds | 2.5 baths | 2 gar
6 Month Minimum Lease Available. Experience the beauty of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking Little Sarasota Bay. Thoughtfully designed for both comfort and flexibility, the home includes a private den or home office, convenient in-unit laundry, and generous living spaces perfect for relaxing or entertaining. Nestled within Hidden Bay, a private 14-acre waterfront community, residents enjoy a peaceful coastal setting directly on the bay—just across from the pristine beaches of Casey Key and the Gulf of Mexico. At the heart of the community is a beautifully renovated clubhouse featuring elegant gathering spaces, a catering kitchen, fitness center, reading library, and dining room. Outside, unwind by the heated pool and spa, gather with friends at the Tiki hut grilling area, or relax beside the tranquil pond with cascading water features. For recreation and adventure, Hidden Bay offers tennis and pickleball courts, a kayak launch, pet park, and car wash station. A scenic elevated boardwalk winds through lush mangrove preserves, leading to a long fishing pier where residents can enjoy peaceful water views, cast a line, or simply take in the area’s breathtaking sunsets. Hidden Bay offers more than a home—it offers a true waterfront lifestyle. Rental rate includes basic cable, internet (expanded services available), water, trash, and pest control. Call for a private tour today. 6-12 month lease period
Listing is courtesy of: GULF COAST REALTY & MANAGEMENT (941-782-1559)Listing Agent: Jaime Barcelo (941-275-3233)
34229 - A4693139 - 204 WINDWARD DR, OSPREY, FL 34229 19 Days on yellowkey
$1,050,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Spacious 3-bedroom, 3-bath home featuring high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. This home combines comfort and style with light-filled living spaces. Enjoy Florida living at its best with a private pool and amazing lanai area with plenty of covered patio. The oversized two car garage provides plenty of space for a golf cart. Located in a highly sought-after Marina community offering a clubhouse and resort-style amenities. There are recreational activities for all ages, tennis, pickleball, bocce ball, playground, kayak launch and storage, jet ski pads, fishing & boating. Southbay Yacht & Racquet Club is a community like no other in that it has a private 172 boat slip Marina with deep water able to accommodate boats up to 58 feet. Walk, bike or take your golf cart to beaches, shopping, restaurants & tiki bars.
Listing is courtesy of: GOLF & BAY PROPERTIES LLC (941-539-8400)Listing Agent: Sharon Lewis (941-966-5400)
34229 - A4690813 - 280 HIDDEN BAY DR #302, OSPREY, FL 34229 19 Days on yellowkey
$749,000 | Condo | 3 beds | 2.0 baths | 1 gar
Move right in and enjoy refined coastal living in this brand-new condominium at Edgewater at Hidden Bay. Offering 1,937 square feet, this thoughtfully designed home features three spacious bedrooms, two stylish bathrooms, and a versatile office—perfect for work or creativity. The sleek kitchen is the heart of the home, complete with premium LG appliances, solid wood cabinetry, and elegant quartz countertops. Sun-filled living spaces are enhanced by large windows with partial views of Little Sarasota Bay, creating a calm and inviting atmosphere. Well-appointed bedrooms and beautifully finished bathrooms provide comfort and style throughout, with high-end details and a seamless, modern layout. Set in the desirable Edgewater community, this home combines upscale living with easy access to scenic waterways and green spaces—offering the perfect balance of luxury and relaxation.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)Listing Agent: Jim Xarras, Jr (978-870-7412)
34229 - A4693150 - 754 PINE RUN DR #754, OSPREY, FL 34229 19 Days on yellowkey
$269,000 | Condo | 2 beds | 2.0 baths | 1 car
One or more photo(s) has been virtually staged. Rarely available and truly one-of-a-kind, this beautifully updated ground-floor 2-bedroom, 2-bath residence offers an exceptional combination of privacy, architectural character, and an unbeatable location. Designed around a stunning private open-air atrium, the home features 8-foot glass doors on three sides, flooding the interior with natural light and creating a seamless indoor-outdoor connection rarely found in condominium living. The thoughtfully designed floorplan delivers a tranquil, nature-inspired experience—particularly from the south bedroom wing, where walls of glass frame peaceful wooded views, offering a remarkable sense of serenity and privacy. Beautifully modernized for today’s lifestyle, the kitchen and living spaces have been opened into a sophisticated great-room design, ideal for entertaining and everyday comfort. Timeless Saltillo Mexican tile flooring runs throughout, adding warmth, texture, and character. Additional conveniences include covered carport parking, a large private storage closet, and tasteful updates that make this residence completely move-in ready. Residents enjoy an impressive collection of resort-style amenities, including two heated pools—one dramatically overlooking a wildlife-filled lagoon—along with two cedar saunas, a fitness center, a Florida-style clubhouse, scenic walking trails, BBQ gas grills, an outdoor gas fireplace, kayak storage, and tennis and pickleball courts. Perfectly positioned for an active coastal lifestyle, this premier location places you just minutes from Nokomis Beach, Oscar Scherer State Park, multiple kayak launches, a public boat ramp, and the Legacy Trail, offering miles of biking and recreation connecting Venice and Sarasota. Nearby favorites include Casey Key Fish House, Historic Spanish Point, waterfront dining, medical facilities, and endless local conveniences. Everyday living couldn’t be easier—walk to Publix, CVS, Ace Hardware, shops, restaurants, fitness centers, Walmart, and the Post Office, or enjoy quick access to everything the area has to offer without needing a car. Families will appreciate proximity to the highly acclaimed Pine View School for the Gifted—the only standalone public gifted school in Florida and consistently ranked among the state’s best. Combining exceptional privacy, thoughtful design, resort-style amenities, and unmatched convenience, this is a rare opportunity to own a distinctive, beautifully updated home in one of the area’s most desirable locations—perfect for those seeking the ideal balance of nature, accessibility, and modern coastal living.
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)Listing Agent: Sasha Volosevych (971-703-0307)
34229 - N6144275 - 4219 FRONTIER WAY #105, OSPREY, FL 34229 20 Days on yellowkey
$2,400 | Condo | 2 beds | 2.0 baths | 1 gar
2 bedrooms. 2 baths, 1 car garage. Condo Unfurnished. Available July 1, 2026. Tenant Occupied until June 22, 2026. 2nd floor. Close to Beaches! Located 10 minutes to Nokomis Beach/Casey Key Beach or 15 minutes to Siesta Key Beach. Minutes by bike to Legacy Trail and Casey Key. Water, Sewer & trash included in the rent. This maintenance free community includes gated entry, resort style community pool, cabana, fitness room, and club room. The construction is concrete block, impact resistant glass windows, tile roof, and paver driveway. The community is conveniently located to Sarasota, Venice, Casey Key, the beaches, dining, shopping, the Legacy Trail, Oscar Scherer Park, and A+ Pineview School! Beautiful unit! $2400 per month 12 month minimum. Tenant Occupied until June 22, 2026.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)Listing Agent: Tim Weller (941-221-0155)
34229 - A4691664 - 156 BISHOPS COURT RD, OSPREY, FL 34229 22 Days on yellowkey
$1,289,000 | Single Family Home | 3 beds | 3.5 baths | 2 gar
One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional lawn care and irrigation are covered by the monthly fees. Designed for both everyday comfort and effortless entertaining, the residence offers 3 bedrooms, 3.5 baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Inside, refined architectural elements, including crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces, create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living spaces, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen featuring custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting. A Sonos sound system extends throughout the residence. The primary suite serves as a retreat with vaulted ceilings, a bay window sitting area, outdoor access, and a fully renovated spa-inspired bath completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. Additional baths have also been extensively renovated with elevated finishes and designer fixtures, while the updated laundry room introduces custom storage, shiplap detailing, and functional built-ins with a refined coastal aesthetic. Upstairs, a spacious bonus room with a fireplace opens directly to a newly renovated second-story deck. With a full bathroom, the second floor is an exceptional flex space ideal for guests, recreation, or private lounging among the treetops. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and serene preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor, new lanai screening and aluminum framing, exterior paint completed in 2025, and a new second-story flat roof with a warranty. Located within the gated community of Bishops Court inside The Oaks Preserve, residents enjoy 24 hour guarded gates, maintenance-free living alongside access to one of the region’s premier private club lifestyles, featuring two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has been awarded the Platinum Clubs of America, Distinguished Emerald Residential Country Club, and Audubon International Certified designations. Located between Sarasota and Venice, Osprey is known for its natural beauty, waterfront lifestyle, and easy access to everyday conveniences. Residents are just moments from Siesta Key, downtown Sarasota’s dining and cultural attractions, marinas, shopping, Legacy Trail, and the renowned Pine View School, creating an ideal setting for both year-round living and seasonal enjoyment.
34229 - TB8504427 - 222 GLENWOOD AVE, OSPREY, FL 34229 24 Days on yellowkey
$275,000 | Single Family Home | 2 beds | 2.0 baths | 1 gar
Take advantage of a RARE OPPORTUNITY in real estate with the current owners ASSUMABLE MORTGAGE at 2.75%! Step out your french doors and wake up to the songs of birds, as you sip coffee in your lanai. The day ahead is whatever you want! What"s your pleasure? Beach? Siesta Key (#1 in US multiple times) is minutes away. Nature Hiking? Oscar Scherer State Park is even closer to your front door. The same goes for Restaurants, Shopping, Golfing and even Tiki Bars. Or maybe a day in Sarasota, at the Ringling Museum, Mote Marine Laboratory, or Jungle Gardens. And that night you can catch a show at the Van Wezel, Asolo Reperatory, or Florida Studio Theater. Afterwards return home to the charm of your bungalow in the sun. Beautiful rosewood floors sparkle to welcome you as you head to a stainless steel decked kitchen for a snack to bring into the open living/dining room and once again visit the french doors. NEWER A/C 2018. NEW LONG LASTING METAL ROOF AND NEW BEAUTIFUL GARAGE DOOR (2025). This home is surrounded by everything you could ever want at an AMAZING Price!
Listing is courtesy of: JAY ALAN REAL ESTATE (855-529-2526)Listing Agent: Zalysia Kaczmarczyk (813-853-3536)
34229 - A4690540 - 51 MACEWEN DR #12, OSPREY, FL 34229 25 Days on yellowkey
$275,000 | Condo | 1 beds | 1.0 baths
Situated in Windsor Lodge in The Oaks Clubside, this updated second floor condo has a kitchenette with quartz countertops, a modern bath, a bonus space set up as a small office area and in-unit laundry. An end unit, it has more windows than the typical interior location, filling the interior with wonderful natural light and offering sweeping views of Eagle #18 and lake. This immaculate condo is perfect for hosting out of town visitors, or for you to use as a weekend get-a-way. And, when you are not using it, the flexible rental policy allows you to easily lease the unit. Offered turnkey furnished and with the convenience of the Windsor Lodge pool and clubhouse just steps away, there is no better way to experience The Oaks with little effort and a lot of comfortable, maintenance-free enjoyment.
34229 - A4692366 - 135 TINA ISLAND DR, OSPREY, FL 34229 25 Days on yellowkey
$3,295,000 | Single Family Home | 3 beds | 4.5 baths | 4 gar
**EXCEPTIONAL WATERFRONT RESIDENCE with 210 ft CANAL FRONTAGE** in desirable Sorrento Shores, offering Deep Water access with No Bridges to the Bay/Gulf. Privately situated on a quiet cul-de-sac, the property enjoys tranquil water and palm views from nearly every room, with canals often visited by manatees and dolphins. Built in 2011 with solid concrete block construction on both levels and encompassing 6,254 sq ft under roof, this residence is designed for durability and peace of mind. The elevated main living level at an 18 ft elevation, features Double-insulated Hurricane-Impact windows and sliding doors on the main level, hurricane impact windows on the lower level, and wraparound balconies with a private lanai to take in sunrise and sunset views. The open-concept interior is designed for comfort and entertaining, highlighted by 14 ft coffered ceilings, crown molding, custom built-ins, LED lighting, and abundant natural light. The kitchen is beautifully appointed with a large granite island, generous counter space, and a gallery window framing the water. The home offers 3 Bedrooms (all En Suite), 3 Full and 1 Half Baths on main level and an additional Full Bath on the lower level. The spacious primary suite includes balcony access, three custom closets, and a spa-style bath with dual vanities, makeup counter, jetted tub, and oversized tiled shower. The lower level includes a 4-Car Garage and provides extensive space for storage and recreational equipment. Construction features include energy-efficient closed-cell insulation, interior metal framing, Hardie/cement board on lower level, concrete stairway, elevator shaft (currently used as a safe room), freshly painted exterior. Enjoy the large paved patio with ample room to add a Pool. Ideally located near world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School.
34229 - A4692408 - 127 PARK TRACE BLVD, OSPREY, FL 34229 26 Days on yellowkey
$795,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Under contract-accepting backup offers. Flawless from top to bottom, this beautifully maintained Florida home offers over 3,000 sq. feet of indoor and outdoor living space, perfect for casual or elegant entertaining. With more than $175,000 in recent upgrades, this stunning water view property blends luxury with peace of mind. Highlights include a new roof, a refinished pool and spa with new heater, and built in Char Broil grill for the ultimate backyard escape. Lush tropical landscaping surrounds the front and back, adding year-round beauty and privacy. Inside, you will find a renovated gourmet kitchen, wood cabinetry, sleek porcelain tile floors, double tray ceilings, and remote-controlled Hunter Douglas blinds. The primary suite is a private getaway with a luxury spa style bath and custom bespoke closet, while six rooms boast gorgeous water views and natural light. In addition you will find an oversized garage with additional overhead storage and built-in work bench Located in the coveted Park Trace Estates in Osprey, you're just 6.5 miles from Siesta Key Beach, a short walk to the Legacy Trail, and jump on a kayak near-by at Oscar Scherer State Park. Adding even more appeal, it is also a short walk to the nationally acclaimed Pine View School. This move-in ready luxury home blends lifestyle, location, and exceptional quality in a beautiful community with HOA's of only $58 a month!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)Listing Agent: Kim Azar-Calka (239-216-6205)
34229 - A4692249 - 184 EXPLORER DR, OSPREY, FL 34229 27 Days on yellowkey
$294,900 | Townhouse | 2 beds | 2.0 baths | 1 gar
Luxury Corner Residence in Osprey | Top-Rated Pine View School District. Welcome to an exceptional opportunity in the heart of Osprey, one of Sarasota County’s most desirable and rapidly growing locations. This beautifully maintained corner-unit residence in Bay Street Village offers an elevated lifestyle just moments from world-class amenities. This FULLY FURNISHED 2-bedroom, 2-bathroom home with a private garage showcases light-filled, open-concept interiors, enhanced by hurricane-impact windows and elegant finishes throughout. The spacious layout is designed for both comfort and entertaining, featuring an oversized kitchen island, stainless steel appliances, and generous storage. Step outside to your private screened lanai, perfect for relaxing mornings or unwinding in the evening in a peaceful, tropical setting. Highlights include: Highly sought-after corner unit for added privacy and natural light Private garage + additional parking Resort-style community with pool Pet-friendly neighborhood Meticulously maintained, move-in ready condition Ideally located just minutes from Siesta Key Beach, Nokomis Beach, dining, shopping, and the Legacy Trail, this property also offers proximity to the nationally recognized Pine View School, consistently ranked among the top public schools in Florida. Whether you are looking for a primary residence, seasonal retreat, or investment property, this home delivers both lifestyle and long-term value. Luxury, location, and top-tier education—this is Osprey living at its finest.
34229 - A4690969 - 6100 JESSIE HARBOR DR #202, OSPREY, FL 34229 27 Days on yellowkey
$850,000 | Condo | 3 beds | 3.5 baths | 1 gar
One or more photo(s) has been virtually staged. Experience elevated coastal living in this beautifully appointed waterfront residence, ideally located within the sought-after Blackburn Harbor community in Sarasota County. Situated on the second floor (building with elevator), this elegant and spacious 3BR + den / 3BA condominium offers over 3,700 SF of a harmonious blend of style and comfort, complemented by serene water views. The open-concept layout features expansive living and dining spaces bathed in natural light, perfect for both everyday living and effortless entertaining. Sliding glass doors lead to a generous wrap-around lanai, creating a seamless indoor-outdoor setting to relax and enjoy tranquil water views, refreshing coastal breezes and spectacular sunsets. The gourmet kitchen is as functional as it is inviting, showcasing rich wood cabinetry, granite countertops, stainless steel appliances, a center island for culinary enthusiasts, and a cozy dinette. A convenient breakfast bar opens to the main living area, ideal for casual dining and social gatherings. The primary suite serves as a peaceful retreat, complete with ample closet space and a well-appointed en-suite bath. Each additional bedroom features its own en-suite bathroom and walk-in closets, offering comfort and privacy for guests or versatility for a home office. Residents of Blackburn Harbor enjoy an array of resort-style amenities, including a heated pool, fitness center, clubhouse, tennis and pickleball courts, kayak storage and launch, and a gazebo with grilling areas. Boating enthusiasts will appreciate the protected deep-water dockage with power and water, and direct access to the Intracoastal Waterway with no bridges. Surrounded by natural beauty, the community provides a front-row seat to Florida’s coastal wildlife, including dolphins and manatees. Just across the street, Oscar Scherer State Park offers scenic trails and outdoor recreation, while nearby waterways invite kayaking adventures to local favorites like Casey Key. Perfectly positioned between Venice (10 minutes) and Sarasota (25 minutes), this location offers convenient access to shopping, dining, and cultural attractions, as well as world-renowned Gulf beaches, including Siesta Key Beach just 15 minutes away. Whether you’re seeking a seasonal escape or a year-round residence, this exceptional property captures the essence of Florida waterfront living.
Listing is courtesy of: CORCORAN DWELLINGS REALTY (941-200-4663)Listing Agent: Angelic Tassos (917-450-0316)
34229 - O6404307 - 212 WASHINGTON AVE, OSPREY, FL 34229 27 Days on yellowkey
$427,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
One or more photo(s) has been virtually staged. Welcome to your private poolside retreat in the desirable coastal community of Osprey— perfectly situated on a premium corner lot with NO HOA and NO CDD fees! This beautiful 3-bedroom, 2-bath home offers a bright, open-concept layout designed for both everyday comfort and effortless entertaining. The spacious living area features sliding glass doors that lead directly to your screened-in lanai and sparkling inground pool, creating seamless indoor-outdoor living. The well-equipped kitchen boasts abundant cabinetry and generous counter space, making it ideal for preparing meals and hosting gatherings. Each of the three bedrooms includes a walk- in closet, providing ample storage and convenience. Retreat to the primary suite, where you’ll find a spa-like jetted tub—perfect for unwinding after a long day. Step outside and enjoy the added bonus of an outdoor shower, ideal for rinsing off after a swim. Additional highlights include a two-car garage, functional layout, and a yard that offers both privacy and potential. With its corner lot location and private pool this home delivers the ultimate Florida lifestyle. Opportunities like this don’t last—schedule your private showing today and make this Osprey gem yours!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)Listing Agent: Jeff Jones (205-902-3584)
34229 - A4691789 - 97 SUGAR MILL DR, OSPREY, FL 34229 29 Days on yellowkey
$1,950,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.
Listing is courtesy of: PALM PARADISE REALTY GROUP (239-955-7256)Listing Agent: Maria Domenech (978-204-3219)
34229 - A4689967 - 4429 CONCHFISH LN, OSPREY, FL 34229 29 Days on yellowkey
$535,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Beautiful residence located in The Palms of Casey Key community, offering a thoughtfully designed layout ideal for everyday living and entertaining. The home spans approximately 2,000+ square feet and features updated flooring throughout all bedrooms and closets, along with tile in the main living areas for durability and easy upkeep. A spacious great room anchors the interior, creating a natural gathering space for family and guests, while the private primary suite is set apart at the rear of the home and includes dual sinks, a soaking tub, walk-in shower, and generous closet space. Outdoor living is highlighted by a covered lanai overlooking a private backyard, ideal for relaxing or entertaining. Additional features include a two-car garage and a well-maintained neighborhood setting with HOA oversight and community amenities nearby. Positioned just steps from Pine View School, it also provides convenient access to US-41 and I-75, placing top-rated schools, beaches, marinas, dining, and shopping just minutes away.
Listing is courtesy of: EXP REALTY, LLC (941-462-3321)Listing Agent: Jennifer Kenna (941-253-3003)
34229 - A4692034 - 254 BURNEY RD, OSPREY, FL 34229 29 Days on yellowkey
$4,500 | Single Family Home | 5 beds | 4.5 baths | 2 gar
Brand-new construction single-family home available for rent in a prime Osprey location! This spacious residence offers 5 bedrooms + 2 dedicated office/study rooms + 4.5 bathrooms + a 2-car garage, also All windows are impact-rated, eliminating the hassle of putting up hurricane shutters while providing extra security, energy efficiency, and storm protection. and ideal for large families or those working from home. Enjoy an open-concept layout with a modern kitchen, high-end finishes, and abundant natural light throughout. The flexible floor plan provides ample space for living, working, and entertaining. Conveniently located just minutes from Pine View School, shopping, dining, and the beautiful Gulf beaches including Siesta Key Beach. Easy access to U.S. Route 41 and I-75 makes commuting simple. Move-in ready. Don’t miss this exceptional rental opportunity!
Listing is courtesy of: FLORIDA MORNING REALTY LLC (941-441-5990)Listing Agent: Phoebe Zhang (727-458-5188)
34229 - A4692030 - 246 BURNEY RD, OSPREY, FL 34229 29 Days on yellowkey
34229 - A4691576 - 408 YACHT HARBOR DR, OSPREY, FL 34229 32 Days on yellowkey
$1,375,000 | Single Family Home | 4 beds | 4.0 baths | 2 gar
Under contract-accepting backup offers. Renovated throughout, this stunning four-bedroom, four-bath residence is in one of the West Coast of Florida's premier marina communities, Southbay Yacht and Racquet Club. This sought-after waterfront community features a community-owned marina with 172 boat slips accommodating vessels up to 55 feet, all within a protected deep-water basin. Enjoy low quarterly HOA fees, $656, for a resort-style atmosphere. This home features a beautifully updated chef's kitchen with a gas cooktop, double ovens and a large island with ample seating. A spacious dining room and wet bar provide an ideal setting for gatherings, while the split bedroom floor plan offers privacy for family and guests. Recent upgrades include a newer roof, hurricane-rated windows, appliances and updated plumbing and electrical. Osprey is between Sarasota and Venice, just 20 minutes to the famous Siesta Key Beach. A quarter mile away, the Legacy Trail offers miles of scenic biking and walking paths, along with easy access to Oscar Scherer State Park. The area has an abundance of waterfront dining options and shopping just a walk or golf cart ride away. Osprey is home to Pine View School for the gifted, consistently ranked the number one school in Florida and among the top in the nation.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)Listing Agent: Thomas Netzel (941-539-0633)
34229 - N6144070 - 14021 BELLAGIO WAY #404, OSPREY, FL 34229 33 Days on yellowkey
$1,175,000 Reduced | Condo | 3 beds | 3.0 baths | 2 gar
This beautifully remodeled waterfront condominium in Osprey offers a blend of luxury, comfort and coastal living, set directly on Little Sarasota Bay with sweeping tranquil bay views from the fourth floor. The residence features three spacious bedrooms and three baths all thoughtfully redesigned with high-end finishes. The modern kitchen has been completely renovated and outfitted with new appliances, Hickory cabinetry and elegant Cambria countertops ideal for everyday living and entertaining. Natural light fills the open living spaces, enhanced by hurricane-rated windows and doors throughout for peace of mind. Go onto the north-facing balcony, equipped with automatic hurricane screens and enjoy serene water views year round. A charming Juliet balcony off the guest bedroom adds an extra touch of architectural character and fresh air access. This unit includes two underground parking spaces, conveniently right outside the elevator for effortless access. Boating enthusiasts will appreciate the included 50-foot boat slip accommodating vessels 44 feet, ideal for exploring the Intracoastal Waterway and beyond. Residents enjoy an array of resort-style amenities including a fully equipped fitness center, heated pool, hot tub, sauna and beautifully maintained outdoor spaces. Gather with friends at the outdoor cooking areas, relax by the fire pit, or take advantage of the kayak launch and sunset dock for unforgettable evenings on the water. A welcoming clubhouse provides additional space for socializing and events. Ideally between Sarasota and Venice, this property offers quick and easy access to pristine beaches, scenic parks, the Legacy Trail, top tier medical facilities, a wide selection of fine dining and shopping. This is a rare opportunity to own a move-in ready waterfront condominium that captures the essence of Florida Gulf Coast living. Schedule your private showing today!
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)Listing Agent: Megan E. George, Pa (941-726-1998)
34229 - A4690387 - 562 OAK BAY DR, OSPREY, FL 34229 33 Days on yellowkey
$530,000 Reduced | Single Family Home | 3 beds | 2.5 baths | 2 gar
Under contract-accepting backup offers. One or more photo(s) has been 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!
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)Listing Agent: Julianna Burns (941-800-7653)
34229 - A4691525 - 354 PINE RUN DR, OSPREY, FL 34229 33 Days on yellowkey
$1,695 | Condo | 2 beds | 2.0 baths
This is an unfurnished 2 bedroom, 2 bathroom condo located in the Pine Run community in Osprey! This upper-level unit features vaulted ceilings, a mix of hardwood and tile flooring, and a distinctive courtyard-style layout that brings the outdoors inside. The kitchen features granite countertops, maple shaker-style cabinets with glass-front uppers, stainless steel appliances, a tile backsplash, and a peninsula with additional counter space. An eat-in area sits adjacent to a sliding glass door that opens to the private courtyard. The living room has wood-grain flooring, vaulted ceilings, and sliding glass doors opening to a balcony with treetop views. The dining area is open to the living room and shares the same vaulted ceiling. A hallway lined with sliding glass doors overlooks the private courtyard, filling the interior with natural light. The master bedroom has vaulted ceilings, sliding glass doors to a balcony, and a walk-in closet with built-in shelving. The master bathroom has a single vanity with a granite countertop and a tub/shower combination. The spare bedroom also features vaulted ceilings, sliding glass doors to a balcony, and custom built-in cabinetry with dresser drawers and upper storage. The spare bathroom has a pedestal sink and a walk-in shower. A laundry closet contains a stacked washer and dryer. The condo also features a private enclosed courtyard with a wood deck, accessible from both the kitchen and the hallway via sliding glass doors. Pine Run is set on over 20 acres of native Florida landscape in Osprey. Community amenities include two heated swimming pools, four tennis courts, pickleball courts, a fitness center, a clubhouse, and shell-covered walking trails that wind through the grounds. A community grilling area and fire pit overlooking a lake provide additional gathering spaces. Pine Run is located on Blackburn Point Road just west of U.S. 41, situated between Sarasota and Venice. The Legacy Bike Trail and Oscar Scherer State Park are nearby, and Blackburn Point Park with a kayak launch is close by. Casey Key and Nokomis Beach are a short drive away, and restaurants such as the Casey Key Fish House are nearby. Downtown Sarasota and downtown Venice are both easily accessible for shopping, dining, and cultural attractions. Please allow up to 30 days after lease signing for community approval before move-in. We score every application. If an application doesn't score high enough, the resident may be required to place the equivalent of two months' rent in a security deposit. Please be aware that leasing this property includes a non-optional Home Assistant Services Package that will cost an additional $39 per month. These services and their cost are separate from Tenant's monthly rent payment and all other payments described in the Lease or any separate Lease addendums. The Home Assistant Services offered are described in the Resident Welcome Packet which can be viewed on Sarasota Management's website.
Listing is courtesy of: SARASOTA MANAGEMENT & LEASING (941-377-8400)Listing Agent: Todd Roughton (941-377-8400)
34229 - A4691036 - 1361 NEW FOREST LN, OSPREY, FL 34229 36 Days on yellowkey
$550,000 | Single Family Home | 3 beds | 2.0 baths | 2 gar
Exceptional opportunity in highly sought-after Rivendell, one of Osprey’s most desirable communities known for its scenic lakes, preserves, walking trails, and beautiful natural surroundings. Ideally located just steps from top-rated Pine View School, offering the rare convenience to walk or bike to one of Florida’s most acclaimed schools. This beautifully maintained home features a durable tile roof, tranquil lake views, and a spacious lanai overlooking the water, perfect for relaxing or entertaining. Enjoy stunning lake views from the dining room, creating a bright and inviting everyday setting. HOA maintained lawn care adds convenience and low maintenance living. The backyard is a tropical retreat with fruit trees including sugar apple, guava, and plum. Prime location near Oscar Scherer State Park, Casey Key beaches, shopping, dining, and the Legacy Trail. Rare combination of location, lifestyle, views, and school district appeal.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)Listing Agent: Linh Pham (941-900-6789)
34229 - A4690672 - 113 BURNEY RD, OSPREY, FL 34229 37 Days on yellowkey
$999,500 | Single Family Home | 3 beds | 2.5 baths | 3 gar
**DON’T WAIT TO BUILD!! NEWER, CUSTOM-BUILT HOME (2020) IS MOVE-IN READY AND PACKED WITH UPGRADES** Situated on a generous 0.52-acre lot near the end of a quiet cul-de-sac, the property offers a private backyard and NO HOA fees/restrictions. Bring Your Toys! Oversized circular driveway provides ample parking for a BOAT, RV, and additional vehicles. This Impressive Residence with 2502sf of heating living space, features 3 Bedrooms plus Study/Den, 2 Full and 1 Half Baths, and a 3-car tandem garage. The Light and Bright, Open Floor Plan is enhanced by tile flooring throughout, tray ceilings, Hurricane Impact Windows and Sliding Doors, plantation shutters, etc. The expansive kitchen is designed for both everyday living and entertaining, featuring a large island, hardwood cabinetry, and premium stainless-steel appliances including Thermador, Bosch, etc. The owner’s suite offers a large, divided walk-in closet and a luxurious en-suite bath with dual vanities and a custom-tiled shower. A spacious, screened lanai provides a beautiful view of the expansive, landscaped and private backyard while showcasing a Heated/Cooled, Saltwater Pool/Spa, along with a large, covered seating area and an Outdoor Kitchen BBQ, Quartzite countertop/sink —perfect for enjoying Florida’s outdoor lifestyle. The Ideally located with easy access to US-41 (Tamiami Trail), this home is just a short drive to world-renowned beaches including Nokomis Beach and #1 rated Siesta Beach, shopping, dining, cultural attractions, and the highly rated Pine View School. **Please Enjoy Viewing the 3D VIRTUAL TOUR**
34229 - A4690942 - 5100 JESSIE HARBOR DR #304, OSPREY, FL 34229 38 Days on yellowkey
$735,000 | Condo | 2 beds | 2.0 baths | 2 gar
Experience effortless coastal living in this stunning third-floor FURNISHED waterfront residence, perfectly positioned for boaters and kayakers in protected waters just off Blackburn Bay and minutes from the Intracoastal Waterway and Gulf. Watch dolphins, manatees, otters, and breathtaking sunsets from your private balcony. Your water views continue inside, flowing through the living room, dining area, kitchen, and primary suite. This spacious, designer-furnished home showcases quartz surfaces, tile and luxury vinyl flooring, a primary suite with balcony access, oversized shower, jacuzzi tub, and three closets. This unit includes a beautifully appointed second bedroom and a versatile den that is currently used as a 3rd bedroom. There is ample storage inside and out- including a first-floor storage unit ideal for all your water toys. Use the community kayak launch for access to Blackburn Harbor and Oscar Scherer State Park. Enjoy the rare opportunity to keep your boat in your backyard with dockage currently available. Your home is set within an 11-acre gated community featuring walking trails, tennis and pickleball courts, a resort-style pool, waterside grill, clubhouse, and fitness center, all just minutes from Nokomis Beach, the Legacy Trail, and vibrant dining and shopping—this is truly the ultimate Florida waterfront lifestyle you’ve been waiting for.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)Listing Agent: Suki Scollo (941-587-2289)
34229 - A4690812 - 409 NORTH POINT RD #401, OSPREY, FL 34229 39 Days on yellowkey
$625,000 | Condo | 3 beds | 3.0 baths
Nestled at treetop level, in Meridian behind the gates of The Oaks Preserve, you will find this elegant residence waiting for you to make it your own. With a spacious master suite, two guest bedrooms (one en suite) and a den, this condo lives large, with room for comfortable, gracious living. Beautifully appointed, every special touch you would want can be found here, Italian ceramic tile, crown molding, ceiling fans and custom lighting. The expansive kitchen features granite countertops and stainless-steel appliances and has a cozy breakfast nook. Practical concerns are addressed by things like electric hurricane shutters in addition to impact windows and doors, and a large laundry room. Meridian residents have use of their own pool, spa and workout room. And can take advantage of all the Oaks Club has to offer, two championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings.
34229 - A4690371 - 51 MAC EWEN DR #14, OSPREY, FL 34229 40 Days on yellowkey
$285,000 | Condo | 1 beds | 1.0 baths
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.
34229 - A4689838 - 51 MACEWEN DR #5, OSPREY, FL 34229 40 Days on yellowkey
$235,000 Reduced | Condo | 1 beds | 1.0 baths
Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.
Listing is courtesy of: 342 REAL ESTATE (941-685-0509)Listing Agent: Sabine Spycher (941-685-0509)
34229 - O6399774 - 759 FORDINGBRIDGE WAY, OSPREY, FL 34229 44 Days on yellowkey
$770,000 Increased | Single Family Home | 4 beds | 3.5 baths | 2 gar
Discover this stunning home located in the heart of Osprey, FL. Featuring a spacious layout, this residence boasts elegant finishes and ample natural light throughout. The modern kitchen is equipped with top-of-the-line appliances and give plenty of storage space. Enjoy the serene outdoor area with a beautifully landscaped yard, appropriate for relaxation and entertainment. Situated in a desirable neighborhood, this property provides easy access to Pineview Gifted School. Don't miss this exceptional opportunity to own this beautiful marvelous 4 bedrooms with a dent and 3 and 1/2 baths opportunity. The circle pool is beautiful and you can see it in Dinnig Room. The master bedroom is spacious with the beautiful marble Venetian team. There are 2 medium room next door. The washer and dryer are new in the laundry room. All the bathrooms are newly installed marble and high luxury tiles. The floor is beautiful with fancy travertine tiles for the whole downstairs floor and the upstairs are high end luxury plank vinyl all new floors and bathrooms
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)Listing Agent: Steven Koleno (804-656-5007)
34229 - A4685559 - 61 BAYHEAD LN, OSPREY, FL 34229 45 Days on yellowkey
$1,185,000 | Single Family Home | 3 beds | 3.0 baths | 2 gar
Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Features: 3 Extra Large Bedrooms, 3 Full Baths, Oversized Main Floor Master Suite w/Sitting Room and Door to Private Back Patio, plus a Wall of Sliders Looking out to the Court Yard Pool Area, Tall Ceilings, Large Walk-in Closet w/Built-ins, Brand New Carpeting plus a 5-Piece Master Bath w/Soaking Tub; Formal Living and Dining Room are Open w/Tall Ceilings, Slider to Pool plus a Den/Library Room off the Living Room and Solid Wood Plank Flooring throughout; Open Kitchen w/Granite Counters and Breakfast Room w/Slider to Pool joined by a Family Room w/Fire Place and Solid Wood Plank Flooring; Pool Bath w/French Door, Main Floor Laundry Room w/Sink, Fabulous Upstairs Suite perfect for Guests or Extended Family w/Bonus Room, 2 Guest Bed Rooms w/Jack and Jill Bath; Extensive Crown Molding, Plantation Shutters thoughout, (2026) New Interior Paint, Central Vac, Large Side Load 2 Car Garage w/Storage, Newly Resurfaced Pool and Spa in the Screened-in Court Yard Entertaining Area, Court Yard Entry Gate, (2025) Brand New Designer Flat Tile Roof, (2026) Painted Pool Deck, (2026) Brand New Paver Driveway. WITH A FEW SIMPLE TOUCHES YOU CAN MAKE THIS HOME ABSOLUTELY FABULOUS! Have VISITORS Coming? NO PROBLEM. THIS HOME MAKES THE PERFECT ENTERTAINING OR SEASONAL FLOOR PLAN OFFERING A PRIVATE UPSTAIRS GUEST SUITE! Neighborhood Community Features: Local Community Pool, 24-Hour Secured Guard Gate, Lush Florida Landscaping and Irrigation are all included in the Maintenance Free Living. The OAKS GOLF & COUNTRY CLUB IS ONE OF SARASOTA'S PREMIER EQUITY "Creme de la Creme" GOLF COMMUNITIES! This amazing COUNTRY CLUB Features: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World Golfing (One of America’s Healthiest Clubs), Three Restaurants, Ballroom, Two 18-Hole Championship GOLF Courses, Award-Winning RACQUET Program w/12 HAR-TRU Hydro-Grid TENNIS COURTS, 4 PICKLE-BALL Courts, CROQUET, State of the Art FITNESS Center, Junior Olympic Heated Pool, Bocce Ball and Basketball Court, Playground Area plus so much more! Located just Minutes to the Top Rated Pine View School, Legacy Bike Trail, Florida's Best Coastal Beaches, Restaurants, Shopping and Costco. THE OAKS CLUB EQUITY MEMBERSHIP IS REQUIRED w/NO WAIT-LIST for SOCIAL or GOLF Memberships. Buyer Bonus: Seller is offering $40,000 towards Buyer's Equity Club Membership!!! ***Most Furnishings are Available Under a Separate Contract.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)Listing Agent: Anne Thomas, Pa (941-993-7700)
34229 - A4690018 - 402 MACEWEN DR, OSPREY, FL 34229 46 Days on yellowkey
$1,699,000 Reduced | Single Family Home | 3 beds | 3.5 baths | 3 gar
Tucked behind the private gates of The Oaks Club side, in one of Sarasota’s most prestigious and sought-after country club enclaves, this exquisite residence captures the essence of refined Florida living. Ideally situated just moments from the clubhouse and overlooking the manicured fairways of the Eagle Course, the home offers a rare blend of privacy, scale, and serene golf course vistas that stretch endlessly from the expansive screened lanai. Spanning over 3,500 square feet, this beautifully appointed single level home features three generously sized bedrooms, a dedicated office, and three-and-a-half baths, all thoughtfully designed to balance sophistication with everyday comfort. From the moment you enter, a sense of understated elegance unfolds—gracious formal living spaces anchored by a statement fireplace, soaring tray ceilings, intricate crown molding, and an abundance of natural light that enhances every architectural detail. The primary suite serves as a true retreat, offering impressive proportions, a substantial walk-in closet, and a spa-inspired bath designed for relaxation. Additional living spaces flow effortlessly, including a well-equipped laundry room with custom built-in workspace, ideal for modern living. Every inch of the home reflects careful attention to detail, from the finishes to the functional layout. Outdoors, the residence truly shines. The screened lanai becomes a private sanctuary, complete with a sparkling pool and spa, perfectly positioned to capture sweeping views of the 4th hole. Whether entertaining guests or enjoying quiet evenings, this space delivers an elevated indoor-outdoor lifestyle synonymous with luxury coastal living. Enhancing both comfort and peace of mind, the home is equipped with a whole-house generator, and Security Camera's outside and the oversized three-car side entrance garage and circular paver driveway provide both convenience and impressive curb appeal. Quick notes to take away: Roof - 2023 / A/C (both units) - 2024 Ownership within The Oaks grants access to an unparalleled private club experience. Residents enjoy two championship 18-hole golf courses, impeccably maintained HAR-TRU tennis courts, newly introduced pickleball facilities, and a state-of-the-art Wellness and Fitness Center exceeding 7,500 square feet. Complemented by an exceptional culinary program and a vibrant calendar of curated social events, The Oaks offers a lifestyle defined by elegance, activity, and connection. Club membership is required, within this distinguished Sarasota community.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)Listing Agent: Steven Kepecz, Pa (941-376-6411)
34229 - A4690063 - 32 SIESTA CIR W, OSPREY, FL 34229 46 Days on yellowkey
$69,000 | Mobile Home | 1 beds | 1.0 baths | 2 car
Charming and affordable 1-bedroom, 1-bath mobile home in desirable Osprey, FL! Situated on a spacious corner lot, this cozy residence offers great potential with a price that reflects the opportunity to update and make it your own. The open living room flows seamlessly into the kitchen, with space for a small dining table—perfect for casual living. The primary bedroom features a convenient built-in desk or makeup area, adding both function and charm. Durable metal siding and roofing provide peace of mind, while the extra-wide carport offers ample covered parking, complemented by additional public parking along the side lot. Enjoy Florida living outdoors with tropical palm trees welcoming you home, a large screened lanai for relaxing or entertaining, and a handy storage shed. Washer and dryer are included for added convenience. A great opportunity to own in a prime location with plenty of potential—don’t miss it! Located in the desirable Arbors community in Osprey, this home is part of an active, friendly neighborhood featuring a clubhouse, swimming pool, shuffleboard courts, outdoor fitness area and a full calendar of social activities. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community.
Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)Listing Agent: Karen Geiger (941-928-8889)
34229 - A4689731 - 14041 BELLAGIO WAY #214, OSPREY, FL 34229 46 Days on yellowkey
$700,000 | Condo | 3 beds | 2.0 baths | 2 gar
Waterfront Sanctuary-Boater's Paradise at the Osprey Harbor Village- 3 Bedrooms | 2 Bathrooms | Direct Intracoastal Frontage Rare opportunity for direct Intracoastal living at Villas at Osprey Harbor Village (formerly Bellagio Harbor Village). This 3 bedroom, 2 bath residence offers approximately 1,862 sq. ft. of light filled living space with views of the canal, Little Sarasota Bay and Intracoastal Waterway. The open concept design features 9’5” tray ceilings, impact windows and doors, and solid wood cabinetry, granite countertops, kitchen island, and kitchen island bar—ideal for entertaining, anchored by a neutral, airy palette with timeless finishes. The split bedroom layout provides privacy, with a spacious primary suite featuring a spa style bath, separate tub and shower, and direct access to an oversized 270 sq. ft. waterfront balcony from the bedroom. Each window is a curated lens, framing the hues of the Bay and the sculptural silhouettes of architectural lines of Mediterranean inspired Villas. Days here are defined by the rhythmic play of light reflecting across the water and the silent flight of ospreys, eagles, and pelicans—a true haven for the bird watcher seeking a quiet refuge. Whether you are hosting a sunset gathering on your private balcony or entertaining your guests at the community terrace, the club room or embarking on a day of boat excursion to the newly opened Midnight Pass, the lifestyle here is one of effortless coastal elegance. Community amenities include a deep water harbor marina with wet and dry slips, resort pool, clubhouse, fitness center, hot tubs, kayak storage, and launch. Centrally located between Sarasota and Venice, and minutes from Venice, Nokomis, Siesta Key, and Casey Key, Oscar Scherer State Park, Spanish Point, Legacy Trail, and cultural and retail amenities of Sarasota. With new metal roof, exterior and interior paint completed in 2025, this property stands as a resilient sanctuary of enduring value. For the resident who values privacy, prestige, and the restorative power of nature, this is the definitive Osprey address. Schedule your private tour today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)Listing Agent: Veronica Lee (609-651-0305)
34229 - A4689541 - 4271 EXPEDITION WAY #103, OSPREY, FL 34229 50 Days on yellowkey
$280,000 Reduced | Condo | 2 beds | 2.0 baths | 1 gar
One or more photo(s) has been virtually staged. Live where everyday life feels simple, connected, and close to everything you love. Located in the gated community of Bay Street Village in Osprey, this beautifully maintained second-floor condo offers the perfect blend of comfort, convenience, and a relaxed Florida lifestyle. Just minutes from Nokomis Beach, Siesta Key, the Legacy Trail, Oscar Scherer State Park, and an abundance of shopping and dining options, everything you need is right at your fingertips. This 2-bedroom, 2-bathroom condo welcomes you with a private entry and interior stairway leading to a bright and open main living space. Positioned on the second floor, the home enjoys added privacy along with elevated views and an abundance of natural light. The layout lives effortlessly, with high ceilings and neutral finishes creating an inviting and airy feel throughout. An attached garage with direct interior access adds everyday ease and practicality. The kitchen is both functional and stylish, featuring granite countertops, stainless steel appliances, a large island with seating, and a walk-in pantry. It opens seamlessly to the dining and living areas, making it easy to host, relax, or simply enjoy day-to-day living without feeling closed off. The spacious primary suite offers a comfortable retreat with a large walk-in closet and an en-suite bathroom complete with dual sinks and a walk-in shower. A second bedroom and full bath provide flexibility for guests, a home office, or additional living space. Enjoy your morning coffee or unwind in the evening on the screened lanai, where you can take in the Florida breeze and peaceful surroundings from your elevated position. Whether you're heading out to the beach, meeting friends for dinner, or enjoying the nearby parks and trails, this location makes it all feel effortless. Bay Street Village enhances the lifestyle even further with resort-style amenities including a community pool, fitness center, scenic ponds, and beautifully landscaped grounds, all within a gated and well-maintained setting. **SELLER FINANCING AVAILABLE** **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)Listing Agent: Toni Zarghami (941-248-2147)
34229 - A4688266 - 1527 BUOY LN, OSPREY, FL 34229 53 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 (941-552-6036)Listing Agent: Matthew Lewis (651-746-4100)
34229 - A4689096 - 409 N POINT RD #1001, OSPREY, FL 34229 53 Days on yellowkey
$2,750,000 | Condo | 3 beds | 3.0 baths | 2 gar
Under contract-accepting backup offers. **STUNNINGLY RENOVATED, MOVE-IN READY 10th FLOOR PENTHOUSE CORNER RESIDENCE WITH GULF AND BAY VIEWS.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional, 3029sf condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. Residents enjoy private amenities including a heated pool and spa, fitness center, and outdoor grilling area, along with full access to The Oaks Club’s renowned lifestyle amenities. 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**
34229 - A4688995 - 313 LOOKOUT POINT DR, OSPREY, FL 34229 53 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 (941-951-6660)Listing Agent: Natalie Gutwein (941-993-2660)
34229 - C7524397 - 1202 JESSIE HARBOR DR #1204, OSPREY, FL 34229 53 Days on yellowkey
$599,000 | Condo | 3 beds | 2.5 baths | 2 gar
Welcome home! This GULF ACCESS, WATERFRONT condo w/ AVAILABLE BOAT SLIPS BEHIND THE UNIT, in the highly sought-after Blackburn Harbor community is ready for its new owners. Offering over 2,000 SQFT, this beautifully updated 3 BED, 2.5 BATH residence with an ATTACHED 2 CAR GARAGE is ideally positioned as a SECOND-FLOOR, END UNIT at the END OF A CANAL—delivering unmatched PRIVACY, VAULTED ceilings, and MILLION DOLLAR WATER & SUNSET VIEWS that feel like a daily postcard. Lush tropical landscaping welcomes you to a private side entrance, while the building’s exclusive setting—just four units total—places you in one of the most desirable locations within the community. Perfectly situated at the edge of the MARINA, you are just STEPS from your BOAT, making it effortless to enjoy GULF ACCESS and endless days exploring nearby WATERWAYS, waterfront DINING, and hidden gems like Snake Island. Inside, this residence blends comfort and coastal elegance with a thoughtfully designed SPLIT FLOOR PLAN for ultimate privacy. The home features warm COASTAL decor, NEUTRAL PAINT, NEW KITCHEN APPLIANCES, GRANITE COUNTERTOPS, SOLID WOOD CABINETRY, custom light fixtures, and window treatments throughout. The open-concept living space flows seamlessly to a LARGE SCREENED LANAI overlooking the water, community park, and glowing SUNSET skies. FURNISHINGS ARE OPTIONAL. Set within a GATED, FINANCIALLY SOUND community spanning approximately 11 acres, residents enjoy an amenity-rich, resort-style lifestyle including a HEATED POOL, CLUBHOUSE, FITNESS ROOM, TENNIS & PICKLEBALL COURTS, KAYAK LAUNCH & STORAGE, BBQ GAZEBO, and scenic walking paths surrounded by lush Florida foliage. The vibrant social calendar offers something for everyone—water aerobics, monthly happy hours, bingo/game nights, pickleball club, book club, and more. Ideally located near US-41, this home offers convenient access to Nokomis Beach, Oscar Scherer State Park, the Legacy Trail, Downtown Venice, Downtown Sarasota, I-75, and Sarasota Memorial Hospital Venice Campus—placing the very best of Florida living right at your fingertips. Whether you're boating to the Gulf, enjoying sunset views from your lanai, or embracing the active waterfront lifestyle, this is truly the Florida Dream come to life. Schedule your private showing today! PLEASE CLICK ON THE VIDEO OF THE UNIT.
Listing is courtesy of: DOWNING FRYE REALTY, INC. (239-261-2244)Listing Agent: Mackenzie Davis-Mahan (941-993-3272)