Location: Osprey
Do Not Show Listings
408 YACHT HARBOR DR, OSPREY, FL 34229
$1,375,00032 Days on yellowkey MLS ID: A4691576
0 Days Off yellowkey (back on 4/28/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2624 Built: 1976Monthly Fee: $219 Tax: $9,482 (2025)Community: Southbay Yacht & Racquet ClubSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,482
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: 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)
854 MACEWEN DR, OSPREY, FL 34229
$3,690,000223 Days on yellowkey MLS ID: A4668918
REDUCED by $100,000 (2.6%) on 05/01/2026
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
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Tax Year: 2024
Middle School: Laurel Nokomis Middle
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)
650 CRANE PRAIRIE WAY, OSPREY, FL 34229
$799,990117 Days on yellowkey MLS ID: A4680121
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3183 Built: 2005Monthly Fee: $427 Tax: $8,138 (2025)Community: Willowbend Ph 3Spa: NoSingle Family
Taxes:$8,138
Remarks: Opportunities like this are increasingly rare in Willowbend. Offering over 3,180 square feet, this Lee Wetherington-built residence delivers exceptional scale, thoughtful architecture, and a preserve setting backing directly to Oscar Scherer State Park. With no rear neighbors and expansive natural views, the home offers privacy and tranquility while remaining minutes from beaches, dining, and cultural destinations. The interior lives large and light-filled, centered around a dramatic great room with a 12-foot double-tray vaulted ceiling that establishes an immediate sense of volume and architectural presence. The open floor plan allows spaces to flow comfortably for everyday living and entertaining, with generous room sizes, flexible living areas, and a second-floor bonus retreat that adds versatility while preserving the ease of main-level living. Built by Lee Wetherington in 2005, the home reflects enduring construction quality, balanced proportions, and a layout designed for longevity. This home stands out not by excess size, but by proportion, preserve setting, and livability—offering a strong foundation for personalization and long-term value within one of Willowbend’s most private settings. Located in the maintenance-free Willowbend community, the lifestyle is intentionally simplified. HOA services include landscaping, irrigation, cable, and internet, supporting a lock-and-leave approach without sacrificing space or privacy. Community amenities include a resort-style pool, fitness center, and recreational spaces within a well-established, deed-restricted neighborhood. For buyers who value build quality, natural views, and compelling price/square foot positioning, this residence presents a rare opportunity in Willowbend—best experienced in person.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Cheri Mazan Castro (941-400-3777)
324 BAYSHORE DR, OSPREY, FL 34229
$3,995,00095 Days on yellowkey MLS ID: A4683138
REDUCED by $255,000 (6.0%) on 04/29/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4389 Built: 2000 Tax: $23,356 (2025)Community: Bay Acres - ResubSpa: YesSingle Family
Taxes:$23,356
Remarks: Big bay views surround you from this exquisitely updated waterfront estate. Welcome to 324 Bayshore Drive, a property of nearly half an acre set on a large, open stretch of the bay with easy access to the Intracoastal Waterway. Even more spectacular is the beautiful water and natural beauty of Midnight Pass which is just to the north of this property and sandbar relaxation just a short boat ride away. This home features all the right spaces and updates- it features a smartly renovated main house comprised of three bedrooms, three and a half bathrooms and spacious office, as well as separate guest suite with full bathroom. From the moment you approach this property you can tell something is different about it. The large front yard features a wraparound drive with tasteful landscaping and as you approach the front door you are transported into true relaxation as you enter over a pool with footbridge to the front door. The immediate thing you will notice are unobstructed beautiful views, high ceilings and stunning architecture. As you take in the 36x36 tile updated flooring you’ll visit the kitchen and great room. The kitchen features upscale appliances from SubZero, Miele and Thermador, as well as sleek European style cabinetry. The main living space opens onto a screened, elevated patio with built-in summer kitchen. The primary is oversized with soaring ceilings and features a spa-like bathroom with free-standing tub, walk-in shower, dual vanities, and walk-in closet. The real fun begins outside- it’s hard to beat the outdoor living space- private sandy beach, heated pool and spa, and large fenced backyard to enjoy. The boating enthusiast will enjoy dual 16k and 10k boat lifts, fish cleaning station, water and electrical service. This home features its own video security system, solar panels with battery backup, a full complement of hurricane shutters, and is located in flood X, indicating no flood insurance required. The roof was replaced in 2025, the structure is built strong with ICF concrete block construction, and the attic insulation is spray foam for energy efficiency. This special estate must truly be seen in person to grasp- schedule your private showing today.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Drew Russell (941-993-3739)
909 MACEWEN DR, OSPREY, FL 34229
$1,595,000624 Days on yellowkey MLS ID: A4621683
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4241 Built: 1991Monthly Fee: $133 Tax: $9,867 (2023)Community: Oaks 2 Phase 2Spa: YesSingle Family
Taxes:$9,867
Tax Year: 2023
Remarks: **STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, etc. 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. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Mark Lyda (941-586-2670)
25 SUGAR MILL DR, OSPREY, FL 34229
$1,550,000128 Days on yellowkey MLS ID: A4678423
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3066 Built: 1998Monthly Fee: $483 Tax: $7,845 (2025)Community: OaksSpa: NoSingle Family
Taxes:$7,845
Middle School: Sarasota Middle
Remarks: METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite Bedrooms, 3 Full and 1 Half Baths. The Updated Kitchen features Quartz countertops, custom hardwood cabinetry, and premium appliances, including Sub-Zero and Wolf. A cozy family room with a wood-burning fireplace provides an inviting gathering space, while impressive Brazilian cherry hardwood flooring enhances the living and dining areas. The spacious primary suite includes a walk-in closet and a luxurious bath with dual vanities, a custom-tiled shower, and a soaking tub. Outdoor living is highlighted by a large screened and covered entertaining area, along with a stunning open-air pool overlooking the tranquil preserve. Additional features include a circular driveway and a peaceful, private setting. RECENT UPDATES include Hurricane IMPACT Windows (2019), HVAC (2021), ROOF (2014), Flooring (2020), Etc. 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. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**
61 BAYHEAD LN, OSPREY, FL 34229
$1,185,00045 Days on yellowkey 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)
113 BURNEY RD, OSPREY, FL 34229
$999,50037 Days on yellowkey MLS ID: A4690672
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2502 Built: 2020 Tax: $10,455 (2025)Community: Bel-AirSpa: YesSingle Family
Taxes:$10,455
Elementary School: Pine View School
High School: Pine View School
Middle School: Pine View School
Remarks: **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**
313 LOOKOUT POINT DR, OSPREY, FL 34229
$5,999,99953 Days on yellowkey MLS ID: A4688995
Bed: 4 Bath: 4.5 Gar: 5 Liv Area Sq Ft: 5337 Built: 2016Monthly Fee: $219 Tax: $20,559 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$20,559
Remarks: 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 Agent: Natalie Gutwein (941-993-2660)
642 TRENTON WAY, OSPREY, FL 34229
$2,150,00066 Days on yellowkey MLS ID: A4686927
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 3939 Built: 2002Monthly Fee: $142 Tax: $16,068 (2025)Community: OaksSpa: YesSingle Family
Taxes:$16,068
Remarks: Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically situated on a half-acre corner lot surrounded by beautiful landscaping with views of the lake and the 14th Fairway of the Heron Course. This 4 bedroom residence has 4 full baths, 1 half bath, a formal living room with pool views, a separate formal dining room, and an open gourmet kitchen with gas cooktop, stainless appliances, two wall ovens, a breakfast bar, an adjoining dining area and two pantries. The kitchen opens to an expansive family room overlooking the pool. The spacious master suite features a large luxury bath, two large his-and-hers closets and a lovely sitting area overlooking the pool. All three additional bedrooms are en suite. A dedicated office with built ins and a versatile bonus room/game room adds valuable flexibility for a wide variety of lifestyles. The large and lovely lanai includes an outdoor grill and bar, covered seating, awnings, and a freeform pool and spa overlooking the water and golf course. With a four car garage, abundant storage and numerous updates, including a new roof installed in December 2024 (with warranty), a new pool heater installed in 2024, new central air conditioning (2 units, 2 zones) in 2022, freshly painted interior and exterior, this home is the perfect choice for those who want to live in comfort and luxury. A complete list of updates is available. The mandatory Membership to The Oaks Club will provide everything for living a country club lifestyle; two championship golf courses, tennis and pickleball courts, a regulation croquet lawn, state-of-the-art wellness center and a wide array of dining and social options.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Steve Abbe (941-400-3969)
362 MACEWEN DR, OSPREY, FL 34229
$2,249,000138 Days on yellowkey MLS ID: A4676567
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4117 Built: 1998Monthly Fee: $142 Tax: $10,742 (2025)Community: The OaksSingle Family
Taxes:$10,742
Remarks: Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with a workspace, overhead storage, and cabinets. Ideally positioned as the closest residence to the clubhouse on MacEwen, the home overlooks the 2nd and 3rd holes of the Eagle Course. Manicured landscaping offers complete privacy. Beyond are breathtaking golf course and lake views. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. The renovated kitchen opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus a formal dining room and breakfast bar for flexible entertaining. This exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership.
312 YACHT HARBOR DR, OSPREY, FL 34229
$1,995,000239 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.
1602 SOUTHBAY DR, OSPREY, FL 34229
$974,900256 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 is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Thomas Kiessling (941-920-1678)
472 PARK TRACE BLVD, OSPREY, FL 34229
$609,000120 Days on yellowkey MLS ID: A4680326
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2217 Built: 2002Monthly Fee: $58 Tax: $5,925 (2025)Community: Park Trace EstatesSingle Family
Taxes:$5,925
Remarks: Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for both everyday living and entertaining, with seamless indoor-outdoor flow to the private SALT WATER POOL. Enjoy mature landscaping on the large corner lot providing added space and privacy, with plenty of room to enjoy the beautiful surroundings. Park Trace Estates has low HOA fees, and is in a prime location close to top-rated schools, shopping, restaurants, Legacy Trail, Oscar Scherer State Park, and Gulf Coast beaches.
Listing is courtesy of: SUNDANCE REAL ESTATE SERVICES (941-780-6710)
Listing Agent: Damon Zuchelli (941-448-5686)
32 BAY AVE, OSPREY, FL 34229
$415,000231 Days on yellowkey MLS ID: N6140978
2 Days Off yellowkey (back on 4/9/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2148 Built: 1962Monthly Fee: $13 Tax: $3,612 (2024)Community: Bay Acres - ResubSingle Family
Taxes:$3,612
Remarks: Under contract-accepting backup offers. Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless steel appliances—all completed in 2022. Yard was completely fenced in 2024. With ample square footage, there’s even potential to add a third bedroom, offering flexibility for your needs. All major systems have been upgraded; now this home is waiting for your personal touch. The oversized garage with over 500 SF has sliding doors leading to the backyard and side-yard. Large 15,500 SF of land there is ample space to add a pool. This home has a split bedroom layout and 2 bathrooms (one en-suite; other could be made en-suite). Not located in a high risk flood zone. The Bay Acres community features a private waterfront park on a protected bay with dockage for boats up to 22 feet, a kayak launch, and storage for kayaks and paddleboards. There’s also a shaded picnic area for relaxing or entertaining. Boaters will love the direct access to the water from the 12-slip community boat basin, with slips available by waitlist. For larger vessels, Blackburn Point Park Boat Ramp is just 1.5 miles away. Located just minutes from Casey Key, Siesta Key, and the A+ rated Pine View School, this property is ideal for boaters, beachgoers, and families alike. Nearby attractions include Oscar Scherer State Park, Selby’s Historic Spanish Point, and The Legacy Trail, while Downtown Sarasota and Venice have plenty of shopping, dining, and entertainment options. Bay Acres is a non-deed-restricted neighborhood, giving you the freedom to park your boat, trailer, or RV without the hassle of HOA restrictions. All the hard work has been done—now it’s time to make this your own piece of paradise.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Michelle Richardson (954-683-1002)
1471 SHOAL WAY, OSPREY, FL 34229
$1,499,00096 Days on yellowkey MLS ID: A4683702
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2798 Built: 1985Monthly Fee: $219 Tax: $6,036 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$6,036
Remarks: One or more photo(s) has been virtually staged. This exceptional residence truly checks every box. Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the end of a quiet cul-de-sac and overlooking an expansive green space, the property feels even more open and serene. No expense has been spared in the home’s extensive upgrades, evident the moment you step inside. Eight-inch wide white oak flooring, custom cabinetry, and high-level quartz countertops create a refined yet inviting aesthetic throughout. A striking, oversized fireplace crafted from natural coral stone anchors the living space and is beautifully framed by solid iron double doors—an architectural feature unique to this home. The layout is equally impressive, offering two distinct living areas, four bedrooms, and three baths, thoughtfully designed to maximize both functionality and flow. The oversized garage includes a workshop area and a climate controlled storage space! With every detail already complete, this home allows you to fully enjoy the idyllic waterfront lifestyle Southbay is known for—whether boating, playing pickleball or tennis, or simply relaxing poolside. Boating in Southbay is made easy with its marina located in the center of the development. Peace of mind comes standard with a metal roof designed to resemble barrel tile, hurricane-rated windows, and a location outside of the flood zone, offering both resilience and long-term value. Pack your bathing suit and bring your boat – live the Florida lifestyle to the fullest. Exclusions: mounted tv/screens, potted plants Pool heater conveys as is
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Lauren Doyle (941-993-9733)
1527 BUOY LN, OSPREY, FL 34229
$1,199,00053 Days on yellowkey MLS ID: A4688266
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2830 Built: 1989Monthly Fee: $204 Tax: $8,555 (2025)Community: Southbay Yacht & Racquet ClubSpa: YesSingle Family
Taxes:$8,555
Middle School: Venice Area Middle
Remarks: 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)
1795 HIGHLAND RD, OSPREY, FL 34229
$385,00084 Days on yellowkey MLS ID: A4684679
3 Days Off yellowkey (back on 4/6/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1879 Built: 1999Monthly Fee: $150 Tax: $2,809 (2025)Community: Towns-End ShoresSpa: NoSingle Family
Taxes:$2,809
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in mind, the property features a unique two-level layout that allows you to live upstairs while renting the lower-level in-law suite, currently producing $1,500 per month on a month-to-month lease. The private suite includes its own entrance, bedroom, bathroom, kitchen, and living area, creating an ideal setup for rental income, guests, or multigenerational living. Upstairs, the two bedroom and two bathroom primary residence offers an open and inviting layout filled with natural light. The kitchen features granite countertops, solid wood cabinetry, and a functional layout that flows easily into the living and dining areas. Crown molding, tray ceilings, wood flooring, and thoughtful design elements add character and comfort throughout the home. Recent updates provide valuable peace of mind, including a new air conditioning system and water heater installed in 2024, while the air-conditioned garage adds versatility for storage, hobbies, or a workshop. Plus, NEW ROOF 2026 with 10 year warranty! NO FLOOD ZONE — meaning flood insurance is not required. Outdoor living is just as appealing. Residents enjoy low HOA dues and access to the sunny community pool, along with the rare convenience of a private kayak launch, allowing you to explore nearby waterways and mangroves with ease. The location truly sets this property apart. Bike to the beach, explore nearby Oscar Scherer State Park, or access the Legacy Trail just minutes away for miles of scenic biking and walking. You are also conveniently located near South Bay and the beautiful beaches of Casey Key, along with local dining, shopping, and coastal attractions. Whether you are seeking a primary residence with income potential, a coastal retreat, or an investment property in a prime west-of-the-trail location, this home delivers flexibility, lifestyle, and value all in one. Schedule your private showing today and experience the possibilities this unique property offers.
Listing Agent: Rachel Tritschler (941-993-5892)
434 MACEWEN DR, OSPREY, FL 34229
$1,465,00061 Days on yellowkey MLS ID: A4687368
0 Days Off yellowkey (back on 4/5/2026)
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2414 Built: 1997Monthly Fee: $142 Tax: $11,162 (2025)Community: Oaks 2 Ph 3Single Family
Taxes:$11,162
Remarks: Meticulously maintained and updated with care, this 3 bedroom, 3 bath + den/study home in The Oaks Clubside offers beautiful views. A mixture between clean modern lines and cottage chic this house feels cozy. Yet it has an open floor plan, soaring ceilings and every room in the house is light and bright. The formal living room opens to the large lanai and pool with Southern exposure. The view over the lake to the Eagle #6 is simply gorgeous! It is one of the most stunning views in the neighborhood. There is plenty of room to host friends and loved ones. Serve a meal in the formal dining room, have a causal lunch in the kitchen nook or at the breakfast bar, or dine al fresco under the large, covered area overlooking the pool. From the luxurious master suite to the guest bedrooms, this home is beautifully appointed and showcases the finest of details and improvements, including a new roof, impact windows and doors and pretty, updated landscaping. The Oaks, Sarasota’s premier golf and country club, offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center.
1016 SCHERER WAY, OSPREY, FL 34229
$950,00062 Days on yellowkey MLS ID: A4687161
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2921 Built: 2003Monthly Fee: $115 Tax: $5,442 (2025)Community: Rivendell Unit 5 The WoodlandsSingle Family
Taxes:$5,442
Remarks: Under contract-accepting backup offers. BEAUTIFUL INSIDE and exceptionally well maintained, this Rivendell home offers the kind of upgrades, efficiency, and outdoor living that are becoming increasingly hard to find. This Luxurious home is situated on a large beautifully landscaped, lake front lot with a Southeast Exposure overlooking Oscar Scherer State park! The interior layout is spacious and functional, featuring tile flooring throughout the main living areas and carpet in the bedrooms for comfort. A dedicated front office connects directly to the primary suite, creating a flexible space ideal for working from home, a sitting room, or even a private retreat. High ceilings and an open flow between the living spaces enhance the overall feel, while the home’s condition reflects true pride of ownership. Step outside and the property truly separates itself. The heated pool has been resurfaced with Pebble Tec and features a solar heating system that was just replaced in 2024, providing year-round enjoyment with energy efficiency. The outdoor space is further enhanced with hurricane roll-down protection, an outdoor stereo system, and a removable baby safety fence—offering both entertainment and peace of mind. Major updates have already been handled, including a BRAND NEW ROOF in 2025 with a transferable 20-year warranty and TWO NEW A/C systems installed in 2025. The home also benefits from an irrigation well, helping maintain the lush landscaping while keeping water costs zero. Total electric costs have remained under $2,400 annually for the entire property, showcasing impressive efficiency for a home of this size. Additional features include a mini-split A/C system in the garage paired with an insulated garage door—perfect for a workshop, gym, or climate-controlled space—as well as a large safe that conveys with the sale. Rivendell residents enjoy a well-rounded lifestyle with low HOA fees that include a heated community pool, playground, and scenic recreational trails—all with no CDD fees. The community offers a rare private path directly to Pine View School and borders Oscar Scherer State Park along with over 200 acres of preserved land, creating a unique blend of convenience and natural surroundings. The home is near both Siesta and Nokomis Beaches, Costco, and loads of shopping and restaurants. Home is situated less than a mile from the Legacy Bike Trail. Minutes to the distinguished Pine View School, the #1 rated public gifted college-prep school in Florida. This is a rare opportunity to own a move-in-ready home where the major expenses have already been taken care of—offering a combination of condition, upgrades, and outdoor lifestyle that is hard to match. Book your private showing now to see this property for yourself!
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