Location: Osprey
Do Not Show Listings
665 CRANE PRAIRIE WAY, OSPREY, FL 34229
$719,000197 Days on yellowkey MLS ID: A4666718
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2306 Built: 2003Monthly Fee: $420 Tax: $4,513 (2025)Community: Willowbend Ph 2Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,513
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2025
Middle School: Laurel Nokomis Middle
Remarks: Discover a blend of comfort and sophistication in this meticulously maintained home in the desirable Willowbend community. The striking architecture of the Ashley floor plan makes it a favorite. Go into a serene oasis featuring breathtaking wide lake views overlooking a sparkling pool, complemented by desired western exposure that invites an abundance of natural light and showcases vibrant sunsets. Gourmet kitchen with natural gas range, stainless dishwasher and refrigerator (new 2026). The interior boasts custom features, including crown molding and elegant tray ceilings. This spacious four-bedroom, three-bath home includes a chef's kitchen outfitted with natural gas cooking, as well as a cozy eat-in area with an aquarium window that beautifully frames the pool and lake views. The owner's suite serves as a sanctuary, offering two walk-in closets and a luxurious bath complete with dual sinks, a walk-in shower, a soaker tub and a separate toilet for added privacy. Thoughtfully designed with a split floor plan, the home ensures guests enjoy ample separation from the owner's suite for optimal comfort. A full-size laundry room adds to the home’s convenience. This exceptional residence is a blank canvas for an extraordinary lifestyle, conveniently near downtown Venice and Sarasota, beautiful beaches, Pine View School and the Legacy Trail. With no CDD fees and in a preferred X flood zone, the low community fees cover ground maintenance, irrigation and access to a community pool and spa, gym, pickleball courts, as well as high-speed internet and DirecTV streaming. Embrace the lifestyle you’ve always dreamed of in this stunning Willowbend home.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Todd Currey (941-402-6000)
61 BAYHEAD LN, OSPREY, FL 34229
$1,185,000Listed 04/15/2026 5:23PM MLS ID: A4685559
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3180 Built: 1993Monthly Fee: $458 Tax: $4,573 (2025)Community: OaksSpa: YesSingle Family
Taxes:$4,573
Elementary School: Gulf Gate Elementary
High School: Riverview High
Middle School: Brookside Middle
Remarks: 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)
664 CRANE PRAIRIE WAY, OSPREY, FL 34229
$887,00054 Days on yellowkey MLS ID: A4681662
REDUCED by $10,000 (1.1%) on 04/08/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2870 Built: 2003Monthly Fee: $437 Tax: $5,460 (2025)Community: Willowbend Ph 2Spa: YesSingle Family
Taxes:$5,460
Remarks: It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wetherington-built Paloma floorplan designed to the highest standards, offering spectacular views and seamless indoor-outdoor living. On one of the community’s most desirable lots, it features unobstructed shimmering views of a wide lake and the natural beauty of the park, creating an extraordinary backdrop for an exceptional lifestyle. The idyllic setting includes a sparkling heated pool and spa. Summer kitchen has sink and stainless beverage refrigerator with large bar entertaining area. The exterior boasts a three-car garage and a double-door that welcomes you into an inviting, spacious interior. The home’s open floor plan includes living/dining with views to the natural beauty, tile on diagonal, crown molding and vaulted ceilings. Handsome office/den to the front of residence. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, including built-in gas range and custom hood. Large walk-in pantry with oversized adjacent laundry room that has an additional deep closet. Dinette area features an aquarium window to take in the natural beauty. Family room is spacious with a corner pocket door that opens wide to let in Florida’s finest weather. The primary suite offers bamboo wood floors, double-tray ceiling and sitting area with French doors. California-style walk-in closets and a luxurious bath with dual sinks, a tub, walk-in shower and separate toilet. Each guest bedroom is generous in size with full bath in between. Additionally, it is a bonus living space with wood floors overlooking the serene setting. Third bath serves as pool bath. On a practical note, new water heater in 2026 and pool pump in December 2025. An amazing lifestyle awaits, all overlooking serene waterfront views teeming with wildlife such as eagles, osprey, otters, turtles and deer. The home is ideally near downtown Venice, Sarasota, Siesta Key, Nokomis Beach and Legacy Trail, offering easy access to cultural attractions, shopping, dining and recreational activities. Short distance to nationally ranked Pine View School. The community’s low fees include internet, Direct TV streaming, yard maintenance, irrigation, pool and spa, gym and pickleball, making this a harmony of luxury, comfort and stunning beauty.
479 SOUTH CREEK DR, OSPREY, FL 34229
$2,495,000135 Days on yellowkey MLS ID: N6141722
0 Days Off yellowkey (back on 4/15/2026)
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4261 Built: 1995Monthly Fee: $150 Tax: $11,095 (2024)Community: South CreekSpa: YesSingle Family
Taxes:$11,095
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Positioned on South Creek just off the Intracoastal Waterway with beautiful views and over 130 FEET of WATERFRONT, this 5-bedroom, 5.5-bath coastal estate offers over 4,261 square feet of refined waterfront living anchored by a truly spectacular backyard oasis. The heated saltwater PebbleTec pool, featuring an impressive 10-FOOT DEPTH, is paired with a separate spa and framed by elegant travertine pavers, with a covered dining area providing a perfect setting for shaded entertaining. An expansive waterfront deck extends beyond the screened lanai for lounging and alfresco dinners overlooking the water. Steps lead to a private dock with a 7,000-pound boat lift and a DEDICATED KAYAK LAUNCH, creating seamless access to the Intracoastal lifestyle. Inside, five generously sized bedrooms each feature ensuite baths and large walk-in closets, with two bedrooms conveniently located on the first floor along with a dedicated office, den, or bonus room. The renovated kitchen is designed for both beauty and function with a Thermador cooktop, Jenn- Airconvection and built-in ovens, a large island, and a passthrough window for effortless outdoor entertaining. The dining area overlooks the pool and includes hurricane-impact sliding doors, a coffee or dry bar with mini-fridge, and additional custom cabinetry for storage. The living room is highlighted by soaring ceilings, transom windows, additional hurricane impact sliding glass doors, and charming shiplap ceiling details, creating a light-filled coastal ambiance. Upstairs, three additional bedrooms and a loft gathering area overlook the living space below, with the true primary suite on the second level along with two waterfront-view bedrooms, all featuring ensuite baths and generous closets, plus a second-floor laundry hookup for added convenience. A spacious three-car garage and elegant U-shaped driveway complete the home. This home has been replumbed and features new lift motors (2025). Located within a gated community offering a basketball court, day dock, playground, and low HOA fees, this property is just 5 miles to Nokomis Beach on Casey Key, 15 miles to downtown Sarasota, 6 miles to the Island of Venice, and 6 miles to Sarasota Memorial Hospital, with Oscar Scherer State Park right nearby for nature lovers and outdoor enthusiasts.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
402 MACEWEN DR, OSPREY, FL 34229
$1,750,0001 Day on yellowkey MLS ID: A4690018
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3565 Built: 1999Monthly Fee: $142 Tax: $13,800 (2025)Community: OaksSingle Family
Taxes:$13,800
Middle School: Sarasota Middle
Remarks: 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)
1348 THORNAPPLE DR, OSPREY, FL 34229
$535,0006 Days on yellowkey MLS ID: A4687822
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2171 Built: 2003Monthly Fee: $397 Tax: $4,051 (2025)Community: Willowbend Ph 1Spa: NoSingle Family
Taxes:$4,051
Remarks: Beautiful lakefront pool home in Willowbend showcases one of the wider, more open water views in the community, framed by an expansive three panel sliding glass door that fills the home with natural light. This three bedroom plus den, two bath residence offers over 2,100 square feet with a functional split floor plan and spacious living areas designed for comfortable everyday living and effortless indoor - outdoor flow. The private screened lanai overlooks the expansive lake and includes a pool, creating a peaceful setting to relax and enjoy Florida’s outdoor lifestyle. Many homes in the community are positioned along narrower sections of the lake, making this view especially appealing. The primary suite offers two walk-in closets, along with a bath featuring both a soaking tub and separate shower. The interior is original and presents an opportunity for a new owner to update and customize to their personal style. Recent improvements include a five year old air conditioning system and one year old water heater. Willowbend is a maintenance-free community with lawn care, landscaping, irrigation and internet included, conveniently located near the Legacy Trail, Oscar Scherer State Park, Nokomis Beach, and Pine View School. Residents enjoy living in a beautifully established setting surrounded by lakes, preserves, and mature landscaping. Willowbend offers a community pool and spa, tennis and basketball courts and playground. This property offers strong value for its location, view, and private pool, and is ready for its next owner to make it their own.
Listing is courtesy of: COLDWELL BANKER REALTY (941-487-1492)
Listing Agent: Margot Leonard (941-387-5050)
172 SEA ANCHOR DR, OSPREY, FL 34229
$895,000154 Days on yellowkey MLS ID: A4671745
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2283 Built: 1977Monthly Fee: $204 Tax: $8,870 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$8,870
Remarks: Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring, saltwater pool and newer cage, den, in home gym, new tile roof, new AC, hurricane impact windows and doors as well as an easy low maintenance open floorplan. Enjoy boating, fishing, biking, pickleball, tennis, bocci ball, kayak storage, jet ski pads and boat slips. Spend evenings sitting by the community pool looking out over the marina watching amazing sunsets. Walk, bike our take a golf cart to nearby shopping, restaurants and tiki bars. A definite value in an amazing community!
Listing is courtesy of: GOLF & BAY PROPERTIES LLC (941-539-8400)
Listing Agent: Sharon Lewis (941-966-5400)
102 WINDWARD DR, OSPREY, FL 34229
$690,000147 Days on yellowkey MLS ID: A4671793
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2134 Built: 1986Monthly Fee: $219 Tax: $3,540 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$3,540
Remarks: NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both full bathrooms, an outdoor shower, a generous laundry room with cabinetry, a practical kitchen with pantry and hurricane rated windows. The paver lanai with automated hurricane screen and expansive paver deck surrounding the swimming pool with solar heat provide substantial outdoor living space. A long driveway adds convenient additional parking. Southbay Yacht & Racquet Club is a golf-cart-friendly community featuring a recently remodeled 10,000 sq. ft. clubhouse with a fitness center, pool, and large patio. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. Additional amenities include pickleball and tennis courts, bocce, shuffleboard, walking and biking paths, and a playground. The community is ideally situated between Sarasota and Venice, close to dining, shopping, entertainment, beaches, the Legacy Trail, and Pine View School.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: David Cyr (941-400-4691)
403 LONGBOW TRL, OSPREY, FL 34229
$1,095,000149 Days on yellowkey MLS ID: A4672081
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2770 Built: 1978Monthly Fee: $42 Tax: $9,020 (2024)Community: Pine RanchSingle Family
Taxes:$9,020
Remarks: Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort, style, and Florida living. Step inside to find a bright, open interior with plenty of natural light, spacious living area, and a seamless connection between indoor and outdoor living. A newly remodeled kitchen with ample cabinetry and a seamless flow for entertaining. The primary suite provides a peaceful retreat with generous closet space and an en-suite bath and balcony with stunning views. Additional bedrooms are well-sized, making this home ideal for guests or a growing household. Enjoy Florida living at its best with an inviting private backyard inground pool framed by mature landscaping perfect for relaxing, gardening, or creating your own outdoor oasis. The backyard showcases a picturesque large pond, with a deck, making it an ideal spot for relaxing evenings. Additionally, this property features an in-law suite with one bedroom and one bathroom, ideal for guests or extended family. Whether you're seeking a full-time residence or a seasonal getaway, this Osprey gem delivers comfort, location, and value. With its prime Osprey location, easy access to Sarasota and Venice, and the natural beauty of the Gulf Coast just minutes away, this home offers exceptional value and an unbeatable lifestyle. A wonderful opportunity to own in one of Sarasota County's most desirable communities don't miss your chance to make 403 Longbow Trail your next home.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Edward Bieker, Pa (941-525-6473)
1019 SCHERER WAY, OSPREY, FL 34229
$735,000102 Days on yellowkey MLS ID: N6142144
0 Days Off yellowkey (back on 1/13/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2498 Built: 2004Monthly Fee: $120 Tax: $6,107 (2025)Community: Rivendell The WoodlandsSpa: YesSingle Family
Taxes:$6,107
Remarks: Welcome to this beautiful 4 bedroom 3 full bath home situated in the desirable community of Rivendell. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. Open Floor plan boasts a 'Chef's Delight' kitchen with plenty of custom cabinets, quartz countertop, updated stainless steel appliance, under cabinet lighting and oversized aquarium window overlooking the lanai. Large living room with tray ceilings. Vaulted ceilings in the family room with a built-in as the focal point. Formal dining room with a palladium window allowing the sunlight in. Wow! describes the spacious screened lanai featuring a salt water heated in ground pool w/spa. Plenty of space for dining, entertaining and games. Backing to the preserve with additional fenced in yard area. Home is situated less than a mile from the Legacy Bike Trail, and nearby Oscar Scherer State Park, Nokomis beach, the Gulf historic downtown Venice, shopping, restaurants & schools. Freshly painted. Bright & Airy. One of the lowest HOA fees around. 3 car garage with EV charging station. Owned Tesla solar panels that keep the electric bills very low. The home checks all the boxes and a must see!
Listing is courtesy of: CENTURY 21 SCHMIDT REAL ESTATE (941-485-0021)
Listing Agent: Christine Appice (908-692-5062)
75 OSPREY POINT DR, OSPREY, FL 34229
$1,695,000147 Days on yellowkey MLS ID: A4672439
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4001 Built: 1983Monthly Fee: $967 Tax: $14,229 (2024)Community: OaksSpa: NoSingle Family
Taxes:$14,229
Remarks: **STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters… situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This former home of famed architect, Bo MacEwen, who also designed the breathtaking Oaks’ Clubhouse, boasts an impressive 253FT frontage along the highly sought-after Osprey Point Drive in the Bayside neighborhood often regarded as the “Park Avenue” of The Oaks Golf & Country Club. A gorgeous new 4ft x 4ft “Celini Agento Italian” tile accentuates the fresh color scheme throughout this well-appointed home complete with impressive fireplace, 14-inch crown moldings, wainscoting, palladium windows and much more! The nearby, private Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. The Oaks-Bayside is a truly 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 AERIAL VIDEO**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
312 YACHT HARBOR DR, OSPREY, FL 34229
$1,995,000194 Days on yellowkey MLS ID: A4667293
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2572 Built: 1978Monthly Fee: $219 Tax: $14,066 (2024)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$14,066
Remarks: One or more photo(s) has been virtually staged. Directly across the street from one of the most exceptional community-owned marinas on Florida’s west coast, this beautifully renovated waterfront residence offers remarkable views and an extraordinary boating lifestyle within Southbay Yacht and Racquet Club. Considered one of the finest private residential marinas in the region, Southbay’s seven-acre deep water boat basin accommodates kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet, with six feet of water at mean low tide and slips for 175 resident owned boats. Even more remarkable, Southbay’s HOA fees are only $218.87 per month and marina slips remain highly affordable, including both water and electric. With the marina quite literally in your front yard and the charming Southbay neighborhood stretching behind you, this fully renovated waterfront home sits on one of only two waterfront streets in the entire community and features three bedrooms, four full baths and a versatile flex space office/fourth bedroom, with many rooms capturing beautiful water views. Inside, the residence welcomes you with an elegant tray ceiling entry, porcelain plank tile flooring and expansive open living spaces filled with natural light from an abundance of impact-rated windows and sliding glass doors. The beautifully designed entertainment kitchen with breakfast area flows seamlessly into the spacious family and dining rooms, creating a refined yet relaxed setting for everyday living and hosting guests. The outdoor living space is equally impressive, showcasing a newly built custom pool and spa framed by a panoramic clear span pool cage, an expansive stone tiled sun deck and generous covered areas for outdoor dining and entertaining. The private primary suite enjoys double door access to the pool and spa and features a luxurious bath with a deep soaking tub, frameless glass shower, dual vanities, large format tile and two custom walk in closets with built in organization systems. Two guest suites each include private en suites, with one offering marina views and the other opening directly to the pool terrace, both with custom closets. This move in ready residence also includes a three car garage, brick paver driveway and mature tropical landscaping. Just steps away, the newly renovated Southbay Yacht and Racquet Club clubhouse overlooks the marina and features a 99 person ballroom with catering kitchen and dance floor, a community gathering room with piano and entertainment area, fitness center, card room, library and meeting room. Residents also enjoy a geothermal heated pool, youth pool, covered waterfront patios, three tennis courts, four pickleball courts, bocce ball, shuffleboard, basketball court, kayak storage, a waterfront park, 20 acres of common grounds and five miles of scenic sidewalks. Southbay is golf cart friendly and offers an active social calendar with weekly gatherings, seasonal events and a vibrant Power and Sail Club. This is a rare opportunity to enjoy marina views, waterfront living and one of the Gulf Coast’s most beloved boating communities. Be sure to request the 50 page digital property catalog and watch the property film for a complete look at this exceptional residence.
Listing Agent: Thomas Netzel (941-539-0633)
730 SARABAY RD, OSPREY, FL 34229
$4,995,000147 Days on yellowkey MLS ID: A4672618
Bed: 4 Bath: 5.5 Gar: 7 Liv Area Sq Ft: 6308 Built: 2011 Tax: $47,200 (2024)Community: Sarabay AcresSpa: YesSingle Family
Taxes:$47,200
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf through nearby Midnight Pass. Positioned along 100 feet of Little Sarasota Bay frontage, it includes a private dock and 15,000-lb boat lift. Inside, the residence provides over 6,300 square feet of living space, soaring ceilings, walls of windows, and sweeping bay views. Wide-plank oak and floor-to-ceiling hurricane-impact windows frame generous living spaces designed for entertaining and an open-plan gourmet kitchen. The primary suite includes a spa-inspired bath and spacious walk-in closets. Upstairs, three en suite bedrooms feature views over the bay; an additional room offers flexibility as a sitting room or fifth bedroom. Outside, a large travertine terrace, resort-style pool and hot tub, propane fire pit, and broad bayside lawn showcase Sarasota’s brilliant sunsets. A four-car attached garage and air-conditioned, detached three-car garage offer space for car collectors, or for an artist’s studio or home gym. Ideally located between Sarasota and Venice, the home has easy access to Siesta Key and Nokomis beaches as well as to the many cultural attractions of Sarasota’s downtown. Additionally, the home has a documented history of no flooding, water intrusion, or hurricane damage, providing significant peace of mind. This bayfront estate is a unique combination of lush acreage, secure elevation, boating access, and luxury coastal living—a complete waterfront lifestyle.
Listing is courtesy of: ROBERT SLACK LLC (352-229-1187)
Listing Agent: Debbie Baraona (941-350-8723)
522 LUMINARY BLVD, OSPREY, FL 34229
$647,00068 Days on yellowkey MLS ID: A4676528
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2320 Built: 2005Monthly Fee: $420 Tax: $4,456 (2025)Community: Willowbend Ph 3Spa: NoSingle Family
Taxes:$4,456
Remarks: This exquisite three-bedroom, three-bath-plus-den, Lee Wetherington built home exemplifies intelligent design and beauty in the community of Willowbend. This Ashley floor plan is thoughtfully oriented to the south, allowing for abundant natural light and stunning lakefront views. The residence features inviting curb appeal with a paver-accented driveway and walkway, leading to an impressive custom double-door entry. Inside, high-end upgrades and recent enhancements contribute to the home's timeless character. The sophisticated interior showcases clean lines, intricate tray ceilings and tile flooring throughout main living areas. Crown molding and impressive lighting fixtures add elegance to the space. The gourmet kitchen is a chef's dream, featuring solid wood cabinetry, Corian countertops and new stainless appliances in January 2026 with gas cooking. Even the laundry room is aesthetically pleasing. The split floor plan affords two guest bedrooms conveniently behind a pocket door, sharing a bath, providing privacy to family and guests alike. The den/study includes a built-in office with a sizeable desk overlooking the lake. The family room boasts a wall of sliding glass doors with an adjacent corner pocket slider that opens wide, seamlessly transitioning to the tranquil outdoor living space. The extended lanai features two covered areas, ideal for relaxation, while the custom pond with waterfall add to the ambience and enjoyment of the tropical surroundings. Water views from most rooms in the home! A well-appointed dinette offers picturesque views of the waterfall and lake through a large aquarium window as well. The luxurious owner’s suite includes dual walk-in closets, dual sinks, a walk-in shower and a tub for ultimate comfort. The home is equipped with high-speed internet and streaming television, with yard maintenance and access to community amenities such as a pool, spa, fitness center, pickleball court and playground all included in the low HOA fees. Convenient to beautiful gulf beaches, Oscar Scherer State Park, Legacy Trail, Pine View School and waterfront dining, this residence offers an unparalleled lifestyle.
121 N CASEY KEY RD, OSPREY, FL 34229
$6,475,000193 Days on yellowkey MLS ID: A4667263
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4096 Built: 1969Monthly Fee: $33 Tax: $37,172 (2024)Community: Casey KeySpa: NoSingle Family
Taxes:$37,172
Remarks: Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting. Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north end of Casey Key offers the rare privilege of a private beach just steps from the home. Set on one of Florida’s most exclusive barrier islands, the property enjoys sweeping sunset views, exceptional privacy, and convenient access to the dining, shopping, and cultural attractions of Venice and Sarasota. Behind a gated entrance, the home features three bedrooms, a private office, and three-and-a-half baths, all thoughtfully updated to celebrate its extraordinary Gulf-front setting. Expansive windows and sliding glass doors frame breathtaking water views while filling the interiors with natural light and coastal breezes. Rich architectural details reflect its hacienda-inspired design, including wood beams and moldings, barrel-brick ceilings, Mexican tile and wood floors, brick accents, artisanal mosaic tile, and hand-painted stair risers. Hurricane-impact windows and doors, a new roof, a new pool, and updated air-conditioning and pool equipment provide both peace of mind and modern comfort. The gourmet kitchen is beautifully appointed with custom cabinetry and Wolf appliances, creating an ideal setting for entertaining after a day on the beach. The primary suite is a private retreat with a sitting room, wet bar, soaking tub, walk-in closet, and private balcony overlooking the Gulf. Two additional en-suite guest bedrooms provide comfort and privacy for family and visitors. A spiral staircase leads to the rooftop deck, where panoramic views stretch from the Gulf to the Intracoastal Waterway. Outside, the courtyard-style pool, fountain, tiled terraces, and lush tropical gardens create a tranquil setting for authentic alfresco living. This is an exceptional opportunity to experience the privacy, beauty, and effortless lifestyle of Gulf-front living on Casey Key.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Napolitano (941-993-0025)
228 SAINT JAMES PARK, OSPREY, FL 34229
$1,695,00026 Days on yellowkey MLS ID: A4686681
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2425 Built: 1997Monthly Fee: $142 Tax: $10,787 (2025)Community: Oaks 2 Ph 1Spa: YesSingle Family
Taxes:$10,787
Remarks: Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors and gleaming mahogany floors. Extensively improved, the home has been repainted inside and out, with refurbished flooring throughout (including the garage), new carpeting, a newly renovated laundry room, new pool equipment with a saltwater system, a new driveway, updated fencing, and refreshed landscaping. The open kitchen has been updated and offers quartz countertops, Sub-Zero refrigeration, a wine fridge, beverage drawers, custom cabinetry, walk-in pantry and an island that serves as a breakfast bar. The great room opens to the lanai with pool, spa, and golf views. The split plan provides privacy with a remodeled master suite featuring a spa-like bath and custom walk-in closet. The south side includes an en suite guest room and a third bedroom/office with lanai access and golf views. Additional features include a 2-car garage with epoxy floor and storage, plantation shutters, a newer roof (2020), hurricane shades and new Pella bay windows. Saint James Park offers easy access to all of The Oaks Club’s offerings: tennis. Pickleball courts, croquet lawn, a state-of-the are WellFit Center, and golf facilities. Members enjoy a wide variety of dining options and a robust social calendar.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
76 OSPREY POINT DR, OSPREY, FL 34229
$1,590,000142 Days on yellowkey MLS ID: A4672843
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4364 Built: 1986Monthly Fee: $475 Tax: $13,509 (2024)Community: Oaks BaysideSingle Family
Taxes:$13,509
Remarks: OWNER SAYS SELL! No Reasonable offer refused on this home that is already the lowest price per Square foot on the market! COMPLETELY UPDATED IS NOT AN EXAGGERATION! This Bo MacEwen–designed 3-bedroom, 4.5-bath home has been updated from top (RE-TILED ROOF) to bottom, with new luxury flooring surfaces throughout and over $650,000 in renovations. No expense was spared in creating a refined, sophisticated residence that still feels warm and inviting. This home truly shows like new, and a full upgrade list is available upon request. Inside, the spacious layout includes a formal dining room, formal living room, and a cozy den with gas fireplace. Crown molding, tray ceilings, plantation shutters, and custom built-ins elevate the elegance throughout. Multiple sets of French doors open to the very private pool area, filling the home with natural light and enhancing indoor–outdoor living. The chef’s kitchen has been refreshed and features a six-burner Viking gas range with grill, Viking hood, Sub-Zero refrigerator/freezer, butler’s pantry, breakfast bar, and dining nook. The primary suite boasts two walk-in closets and a recent down-to-the-studs, resort-level bathroom remodel—one that would make even the Ritz envious. One guest suite occupies the west wing, while a spacious second-level suite adds comfort and flexibility. Significant structural upgrades include NEW low-E hurricane-impact windows and skylights, roll-down hurricane shutters (front and rear), and a whole-house generator for added peace of mind. Exterior enhancements include a NEW paver driveway and pool deck, extensive landscape lighting, and a very private pool area with new built-in grill and bar. Located in one of the Gulf Coast’s premier country club communities, The Oaks offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center. Club membership is required with homeownership.
120 CANDYCE DR, OSPREY, FL 34229
$650,000161 Days on yellowkey MLS ID: A4667108
4 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 2103 Built: 1962 Tax: $10,123 (2024)Community: Sorrento ShoresSingle Family
Taxes:$10,123
Remarks: Under contract-accepting backup offers. This is your chance to own a true waterfront property in the highly desirable Osprey area and transform it into your dream coastal retreat. Situated on a canal with direct access to the Intracoastal Waterway, this home offers an unbeatable location for boating enthusiasts and anyone seeking the ultimate Florida lifestyle. The property itself needs some love, but that’s exactly what makes it such an incredible opportunity. Bring your vision, contractor, and creativity to design a space that’s entirely your own. Unlike many homes nearby, this property did not experience any flooding, offering peace of mind and a solid foundation for your renovation. Whether you’re an investor looking for your next project or a buyer eager to build sweat equity in a prime waterfront community, 120 Candyce Drive delivers both value and potential in one of Sarasota County’s most sought-after coastal neighborhoods. Ideally located just minutes from Nokomis Beach, Casey Key, and popular waterfront dining, this home combines location and opportunity with no HOA restrictions. Turn this waterfront fixer-upper into your stunning Florida escape.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Michelle Ward (941-920-2460)
1602 SOUTHBAY DR, OSPREY, FL 34229
$974,900211 Days on yellowkey MLS ID: A4665288
1 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2980 Built: 1986Monthly Fee: $204 Tax: $9,955 (2024)Community: Southbay Yacht & Racquet ClubSingle Family
Taxes:$9,955
Remarks: Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle—enhanced by thoughtful recent updates including a new roof replaced in 2023, fresh interior paint, an updated kitchen, and a beautifully updated pool and jacuzzi. As you arrive, mature tropical landscaping and stately curb appeal immediately set the tone. Step inside to a generously sized home designed for both relaxation and entertaining. Open living areas, large windows, and high ceilings create an airy, welcoming atmosphere, while the refreshed interiors offer a clean, move-in-ready feel. The updated kitchen serves as the heart of the home, providing both style and functionality for everyday living and hosting guests. The interior flows seamlessly into the private outdoor oasis, where the recently updated pool and jacuzzi invite you to enjoy endless days under the Florida sun. Whether hosting friends for a casual barbecue, unwinding with a sunset soak, or enjoying your morning coffee poolside, this space perfectly embodies Florida’s indoor-outdoor lifestyle. Positioned on a corner lot, the home offers exceptional privacy, light, and space—ideal for family gatherings or a peaceful retreat. Spacious bedrooms provide comfort for both owners and guests. A washer and dryer convey with the sale, along with a brand-new pool table, adding both convenience and entertainment value. Life in Southbay Yacht & Racquet Club is more than just owning a home—it’s embracing a lifestyle. Enjoy access to the deep-water marina with Gulf access, tennis and pickleball courts, a vibrant social calendar, fitness amenities, and waterfront strolls. Just minutes away are the pristine beaches of Siesta Key and Nokomis, along with world-class dining and boutique shopping. Here, every day truly feels like vacation.
Listing Agent: Thomas Kiessling (941-920-1678)
854 MACEWEN DR, OSPREY, FL 34229
$3,790,000178 Days on yellowkey MLS ID: A4668918
Bed: 4 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 9081 Built: 2003Monthly Fee: $133 Tax: $26,109 (2024)Community: Oaks 2 Ph 2Spa: YesSingle Family
Taxes:$26,109
Remarks: One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the lanai, where golf course views frame the heated pool, spa, and outdoor kitchen. The first-floor primary suite is a true retreat, featuring high ceilings, multiple closets, and a flexible sitting area that can serve as a nursery, gym, or private office. Upstairs, guests enjoy their own wing complete with a loft, theater, and screened terrace—ideal for relaxing or hosting in style. A split four-car garage, custom finishes, and generous room throughout reflect the craftsmanship expected in one of Sarasota’s most distinguished country club communities. The Oaks offers 24-hour security, two championship golf courses, an acclaimed racquets program, fitness and wellness facilities, and fine dining—all just minutes from the beaches and top-rated schools. Experience this home for yourself—take the 3D virtual tour and book your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Joe Murphy (941-780-3260)
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