Southbay Yacht & Racquet Club Real Estate, Homes, Condos for Sale in Osprey/Nokomis, FL - Ed Grabowski

3 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Welcome to this exceptional Southbay home featuring the rare and highly desirable 3 car garage! From the moment you step inside, you’ll appreciate the elegant finishes, soaring tray and vaulted ceilings with crown molding, and beautiful travertine flooring throughout. The entry opens to the spacious dining area and leads into the oversized Greatroom which flows seamlessly into the chef-inspired kitchen, offering an abundance of cabinetry, generous counter space, a center island, Thermador induction cooktop, two sinks, pull-out drawers, pantry, and a bright dinette highlighted by a stunning aquarium window. Just beyond the kitchen is an impressive butler’s pantry featuring extensive u-shaped cabinetry a second refrigerator, laundry room and a convenient third full bath. The adjacent den is warm and inviting with a fireplace and corner sliding glass hurricane rated doors leading to the lanai and outdoor kitchen. A unique office or craft room with wood-paneled sliding doors can be closed off for privacy or opened to expand the living space. The spacious primary suite offers two walk in closets and lanai access through sliding glass doors, while two additional bedrooms share a well appointed guest bath and privacy pocket door. Just inside from the garage, you’ll find a convenient drop zone and half bath. Major updates include: NEW TRANE A/C INSTALLED 4/25, HURRICANE RATED WINDOWS, AQUARIUM WINDOW WITH ACCORDION STYLE WRAP AROUND HURRICANE SHADE, COVERED LANAI AREA WITH REMOTE CONTROLLED ELECTRONIC HURRICANE METAL SHADE, H/W TANK 2 YEARS OLD, NEW LED POOL LIGHT, NEWER SALTWATER VARIABLE SPEED POOL PUMP (5 YEARS OLD), NEWER LANAI FANS, ROOF 2015/2017, OVERSIZED PAVER DRIVEWAY 2015, RE-PLUMBED 2015, NEW IRRIGATION 2015, ECO WATER SOFTENER & R/O SYSTEM, LEASED WATER FILTRATION SYSTEM. Located in the highly sought-after Southbay Yacht & Racquet Club, residents enjoy an active lifestyle with a private marina offering low dock fees exclusively for Southbay homeowners. Situated on the intracoastal Waterway, the marina accommodates boats of nearly every size. This golf cart-friendly community also features an updated clubhouse with ballroom, gathering room, two kitchens, fitness center, card room, and library. Outdoor amenities include a community pool, tennis and pickleball courts, kayak launch and storage, bocce court, basketball courts and playground. All this is perfectly located in desirable Osprey, just minutes from shopping, restaurants, Pineview School, major roadways, downtown Venice and Sarasota, and the beautiful beaches of Nokomis and Siesta Key. Don’t miss this incredible opportunity to own one of Southbay’s most feature-rich homes! Schedules your private showing today.

486 Yacht Harbor Drive, Osprey

$3,100,000

3 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Experience the epitome of waterfront living in the sought-after Southbay neighborhood. This 3 bedroom, 3.5 bath home is ideally positioned on a peninsula, providing sweeping panoramic water views. The moment you step inside, you will be mesmerized by the breathtaking bay views through a plethora of windows and sliding glass doors that flood the space with natural light. The open, main level is designed for both comfort and style, with vaulted ceilings, unobstructed water views from every room and hardwood floors. The kitchen is uniquely designed, featuring an extended breakfast bar, high end designer cabinets and stainless steel appliances. The great room, with wet bar, has views so perfect, they almost feel like artwork. The new clear view lanai screens provide a gorgeous tropical back drop to the pool and spa. Host friends and loved ones, using the outdoor kitchen and setting area for a fun-filled dinner, and watch the sun set, painting the sky with a golden glow. The first floor master suite consists of a spacious bedroom, a spa-like bathroom, and a separate area utilized as a private study. Upstairs you will find two additional en suite bedrooms. One opens to the new deck, has views over the Dryman Bay out to Casey Key, and is large enough to use as a second master suite. While the views and location of this home are drop-dead gorgeous, practical features also abound. This home has impact windows and doors, a brand new washer and dryer, and recently replaced roof, AC and tankless hot water heater. Southbay Yacht and Racquet Club has a seven-acre deep-water marina accommodating boats up to 55 feet with slips available to homeowners. It has an updated clubhouse and fitness center overlooking the bay, complete with a ballroom, catering kitchen, meeting room and library. Community amenities also include a geothermal heated pool, children’s pool, tennis, pickleball, shuffleboard, basketball and kayak storage. Residents enjoy 20 acres of lush common grounds and five miles of walking trails, plus a vibrant calendar of social events.

321 Lookout Point Drive, Osprey

$799,900

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Wow! What a great price for this 2,474 square foot home in the sought after neighborhood of Southbay Yacht and Racquet Club. Unique “U” shape design gives a unique courtyard feel to the pool and lanai area. Enter into the foyer with travertine flooring and look straight ahead to the pool courtyard. This home is perfect for entertaining with the living room used as a game room with your own pool table. Dining room offers a built in bar area. Nicely equipped cherry kitchen opens to family room with fireplace and sliding glass doors onto the courtyard. Travertine floors are also in the diningroom, kitchen and family room. The primary suite is located on one side of the home while the other two bedrooms are on the other side. The primary suite also looks onto the pool area. The large courtyard offers plenty of covered space for lounging plus solar heated pool, and an above ground hot tub! All furniture can be left with the home and is negotiable if you are looking to move right in and start enjoying the fabulous Florida lifestyle. OTHER BENEFITS OF THE HOME INCLUDE RECENTLY REPLACED A/C, A GENERATOR, ROOF APROX. 13 YEARS OLD, POOL RESURFACED IN 2009. Speaking of lifestyle…there is none finer than living in Southbay! The marina which is exclusive to Southbay residents offers low dock lease fees. Renovated club house has much to offer including a ballroom, casual “livingroom” areas, two kitchens, fitness center, card room, library, community pool, pickleball courts, tennis courts and activities galore! Picturesque views, walking trails, kayak launch, kayak storage, playground, bocce ball court and more. Come explore Southbay, you won’t be disappointed!

1495 Landview Lane, Osprey

$1,795,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Offering 3 bedrooms, 2 baths, den/office, 2,411 square feet under air, a spacious living room, a 2-car garage, and a private 14' x 37' heated pool centrally positioned as the focal point of the home. This beautifully updated, move-in-ready residence blends luxury, comfort, and the ultimate coastal lifestyle in the highly sought-after waterfront Southbay Yacht & Racquet Club - Marina Community. The thoughtfully designed split floor plan is ideal for indoor-outdoor living. Multiple rooms overlook and open directly onto the covered lanais and the private heated pool, which is framed on three sides by the home creating a stunning courtyard oasis. Dramatic floor-to-ceiling impact-rated windows and sliders (2020) frame beautiful pool views, while soaring ceilings and an abundance of natural light enhance the bright, open feel. The luxurious primary suite includes an adjoining office/den and an ensuite bath with soaking tub and custom cabinetry. Two guest bedrooms and an updated guest bath are located in a separate wing. A custom queen-size library-style Murphy bed adds flexibility for guests or workspace. Step inside to discover stunning 12” x 72” Ceramica Sant’Agostino Italian porcelain plank tile flooring (Barkwood Ash) throughout, soaring ceilings, custom millwork, new 8-inch baseboards, upgraded lighting and fans, and fresh interior and exterior paint (2025). The chef-inspired kitchen features all-new custom cabinetry, quartz countertops, a large center island with seating for 8-10, high-end 2025 GE Monogram appliances (including 48” refrigerator, induction cooktop, and wall oven/microwave), a built-in wine refrigerator, and excellent storage. The open dining area includes a beautifully integrated bar with custom cabinetry and a fireplace (ready for insert). Additional highlights include dual-zone A/C systems (new 2025), new Electrolux stackable washer and dryer (2025), spacious laundry room with utility sink and coffee/tea bar, new concrete tile roof (2020), re-plumbed (2007), oversized 2-car garage with epoxy floor and custom storage, mature tropical landscaping with irrigation, private outdoor shower, and room to add a 4th-bedroom with ensuite bath or additional garage storage. Located in the desirable Southbay Yacht & Racquet Club - Marina Community, this premier boating community features a private 172-slip deep-water marina that can handle vessels up to 58 feet for very reasonable fees. Residents enjoy low HOA fees and a wonderful social atmosphere with a clubhouse, fitness center, heated community pool, spa, tennis courts, pickleball, basketball, bocce, playground, kayak launch/storage, jet ski pads, and more. This golf cart-family friendly community offers easy access to Nokomis Beach, Casey Key, waterfront dining, shopping, Publix, Aldi, restaurants, and tiki bars. All interior and exterior furnishings, artwork, TVs, potted plants, and outdoor gas grill with pizza oven are available for purchase separately via bill of sale. This is a must-see, comprehensively updated home in Southbay.

206 Four Knot Lane, Osprey

$1,400,000

4 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Under contract-accepting backup offers. Elevated luxury throughout this Southbay beauty! Step inside this one of a kind two story home and you will feel like you are at a top resort! You will enter the foyer overlooking the living room and dining room area, just perfect for entertaining highlighting a built-in buffet with wine cooler. Open the sliding glass doors ahead and enter the exquisite out door living area, heated salt water pool, spa, outdoor kitchen and dining area, all adding up to the feeling of relaxed elegance. The kitchen is a dream! Top of the line Thermador appliances including a smooth induction top stove, built in oven and microwave and for the ultimate in extravagance - a built in Thermador coffee maker. Quartzite counter tops, over sized island, custom pantry, sliding glass doors to exterior help complete this gathering spot. Located on the first floor is the spacious master suite with triple sliding doors looking onto the lanai area. Master bath with tub and an oversized window looking onto a private zen garden. The spacious second bedroom currently used as an office features corner windows and has a full luxury guest bath right out side its door. The oversized family room with vaulted ceiling and wood beam accents will be a great family retreat with a built in new state of the art fireplace and TV. Unique pebbled wallpaper adorns one wall to help maintain the resort feel. First floor laundry with built in cabinets is also on the first level. Upstairs you will find two nice sized bedrooms plus a full bath with double bowl sinks. The upstairs bonus room is a fun hideaway for a play room, office, or workout room, featuring glass French doors. Plenty of storage in this home with several attic accesses. Other important features include plantation shutters through-out, one new A/C unit in 2025, attic TAP insulation installed 2025, stackable washer and dryer 2024, new GAF coating on TPO flat roof (lanai), interior painted 2024, extensive landscaping 2025 including addition of a side private patio, and lanai wood ceiling 2025 and new hurricane rated glass in double front door. All the beautiful furnishings and decor items in the home are negotiable as well. So many more details you will just have to come and see for yourself. The Southbay Yacht and Racquet Club is a vibrant community with many amenities, activities and offers it’s own marina to residents. The marina dock fees are low and has space for most boat sizes. Also in the marina is a kayak launch and storage on site. The renovated clubhouse offers a fitness center, 99 person ballroom, livingroom, two kitchens, pool, bocce balls, tennis and pickleball. Centrally located between Sarasota and Venice, area beaches, restaurants and shopping. The local favorite restaurant, Casey Key Fish House & Tiki Bar is right down the road! Southbay is a fabulous place to live and play - and as they say, come and buy your boat a home!

1474 Landview Lane, Osprey

$875,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Under contract-accepting backup offers. 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!

157 Lookout Point Drive, Osprey

$1,105,000

5 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

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.

272 Four Knot Lane, Osprey

$850,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Don't miss this opportunity to own a home in a desirable private marina community. This spacious 3-bedroom, 3-bath home features high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. An amazing Value! A combination of 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. Southbay Yacht & Racquet Club is a highly sought-after Marina community offering a clubhouse, resort-style amenities and 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.

204 Windward Drive, Osprey

$1,250,000

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

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.

408 Yacht Harbor Drive, Osprey

$1,165,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

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.

1527 Buoy Lane, Osprey

$5,999,999

4 Beds ⋅ 5 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

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.

313 Lookout Point Drive, Osprey

$1,265,000

4 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

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

1471 Shoal Way, Osprey

$565,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Price was dropped $50,000 on 5/7! Survey and pool quote are available! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been professionally painted in 2025, and there is tons of natural light that flows through the many windows of this home. The kitchen is open to the family room and dinette for easy entertaining. There is also a HUGE bonus room toward the back of the home. Next to the family room is entrance to the hallway leading to the two guest bedrooms and guest bathroom. On the opposite side of the home, past the dining room is the spacious primary suite with generous walk-in closet and ensuite bath. The laundry room is located near the family room. Entrance to the attached 2 car garage is near the foyer. Roof was replaced in 2022 & AC was installed in 2016. The entire house has also been replumbed! Southbay Yacht & Racquet Club is an active lifestyle community with many social, boating, and sports activities. The clubhouse has recently been renovated and features a community pool, fitness center, ballroom, two kitchens, card room, game room, and an elevator! Additional amenities include 3 tennis courts, 4 pickle ball courts, basketball, playground, bocce, shuffleboard, and miles of walking trails and green space. The community-owned marina—with residents-only boat slips—provides direct Intracoastal Waterway access with no fixed bridges to the Gulf. The community is welcoming and lively—perfect for families and those who enjoy an active, coastal lifestyle. This community is in the perfect location with several warm gulf beaches, Downtown Venice & Downtown Sarasota close by. The famous Casey Key Fish House and Tiki Bar are just a golf cart ride away! Oscar Scherer State Park is across Tamiami Trail and Pine View (#1 school in the state) is about 5 minutes away. This home is ready for you to start living the elevated Southbay lifestyle! **The street behind this house (Blackburn Point Rd.) is a fairly quiet two lane Rd. That's the road you can take your golf cart to Casey Key Fish House & Tiki Bar!**As of Jan 2026, there is marina space available immediately (no wait list) and fees range between $169-$705 per quarter depending on what size you require.This is subject to change.**This listing went pending in March. When the buyers couldn't secure their financing, it went back on market. No inspections have been done.**

186 Windward Drive, Osprey

$1,065,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Relax, you can move right in this one! This Southbay home has been updated beautifully with so many quality and custom features. A complete interior remodel was done in 2016 including all new underground PVC piping. A well thought out floor plan offers plenty of entertaining area including a living room with vaulted ceiling and open dining room. The new custom kitchen (2016) showcases custom cabinetry with Cambria quartz counter tops, glass backsplash, plenty of cabinet drawers plus roll out shelves in pantry. High end appliances including an induction stove. The primary bedroom and bath offer many updates with the highlight being the high tech whirlpool tub with controls for multi-colored mood lighting and a radio! The guest bedrooms each offer designated bathrooms with pocket doors to close off the bedroom and bath making two private guest suites. An office with closet features an original hardwood floor with inlaid wood design. You’ll enjoy the low electric bills with 3 types of solar power. Solar power for hot water, solar power for pool were both added in 2013. In 2014 solar electric was added to power the house. A complete lanai renovation in 2019 includes new screen enclosure and enlarging the entire lanai, the addition of a spa, and the pool resurfaced with pebbletec, new travertine pavers, light, fan and pool heat pump. In 2020 a new Lennox air conditioner was installed. Other interior updates in 2016 include: travertine flooring in living room and dining rooms, Brazilian teak in kitchen and family room, Acacia engineered hardwood in bedrooms and porcelain tile in all baths and laundry room. All interior doors replaced, all new baseboards and crown molding in all bedrooms, diningroom and kitchen. The family room with vaulted ceiling has the addition of a wet bar area with sink, beverage refrigerator with ice maker, custom cabinets and quartz counter. The fireplace with propane gas was refaced and custom shelves and cabinetry complete the look. Several large sliding glass doors fully extend and open onto the lanai. All new remodeled bathrooms with custom cabinets, custom tiled showers and new fixtures. Quartz counter tops in primary bath and one of the guest bedroom baths. The third bath doubles as a pool bath and has a granite counter top. New impact glass double front door was also added. 2017 a new hurricane rated garage door was added. You’ll have to come and see for yourself all the upgrades and updates and enjoy the livability of this home. The always popular. Southbay Yacht & Racquet Club is a vibrant, active community with a beautifully renovated clubhouse which o holds many social events and clubs. Other amenities include a community pool, pickleball and tennis courts, bocce ball, playground, basketball, kayak launch and storage. The marina with leased boat slips for most boat sizes are available only to residents of Southbay and opens onto the Intercoastal waterway. Convenient location close to the local favorite, Casey Key Fish House and Tiki Bar, with other shopping and dining near by. Just a quick drive to local beaches, downtown Sarasota and Venice. Isn’t it time to treat yourself to this fabulous new home and start living the Southbay lifestyle?

1235 Yacht Harbor Drive, Osprey

$565,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

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.

102 Windward Drive, Osprey

$2,199,900

5 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Virtually Staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary residence taken fully down to the studs and reimagined as a like-new, luxury smart home. Set on a .4-acre lot in Flood Zone X (no lender-required flood insurance), this never-lived-in five-bedroom, 3.5 bath, 3,236-square-foot home blends solid block construction with high-end design and cutting-edge technology. No detail was overlooked, including a standing seam metal roof, all new high-velocity impact windows, hurricane-rated garage doors and fully integrated Alexa features throughout. Wide-plank wood floors lead through a thoughtfully designed layout featuring custom built-ins including a kitchen desk, mudroom storage, dining room bar with wine refrigerator and living room shelving with glass doors. The kitchen is a showstopper with two large quartz islands, top-of-the-line Thermador appliances, a microwave drawer, concealed refrigerator, gas range with double ovens and a custom glass-door butler’s pantry. French doors at the entry feature Alexa-controlled electronic glass for your choice of instant privacy or transparent green views, while oversized sliders in the main living area fully retract for seamless indoor-outdoor living. The massive laundry room is a dream with two washers, two dryers, abundant storage and countertop space. Outside, enjoy a stunning new saltwater pool with cage, paver decking, and a state-of-the-art outdoor kitchen including storage and pullout drawer refrigerators, ideal for entertaining. The oversized garage offers excellent storage and the home’s elevation offers added peace of mind. Southbay is one of Sarasota County’s desirable waterfront communities with an updated clubhouse and fitness center overlooking the bay, complete with a ballroom, catering kitchen, meeting room and library. Community amenities also include a geothermal heated pool, children’s pool, tennis, pickleball, shuffleboard, basketball, kayak storage and a seven-acre deep-water marina accommodating boats up to 55 feet. Residents enjoy 20 acres of lush common grounds and five miles of walking trails, plus a vibrant calendar of social events. Near SR 681, with easy access to downtown Sarasota, Venice, beautiful beaches and A-rated schools including Laurel Nokomis, Sarasota Middle, Venice High, Pine View and the European Academy. This is a rare opportunity to own a turnkey, top-tier home in an unmatched boating community.

180 Lookout Point Drive, Osprey

$3,500,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Ahhh…you have finally found “the one”! This home is a one of a kind property with one of the best water front lots in Southbay! Features of this spectacular home include not only a lagoon style pool with waterfall, but a lagoon with a winding deck bridge walkway taking you past another waterfall, to the intracoastal water way! Imagine your morning coffee or evening sunsets “sitting by the dock of the bay”. Inside, this home is filled with character. Etched glass panels tell a story in the master bedroom. The office has built-in cabinetry and etched glass panels. The master bathroom has sliding glass doors to outdoor shower and zen area…just to name a few. One of the many exciting features of this home is the 4th car garage, the auto atrium! Car enthusiasts, you now have a place to show off your pride and joy! This home was built with quality and the kitchen shows that off. Glossy high end cabinetry and built-in luxury appliances have a timeless beauty. The roof was replaced in 2022 and 3 new air conditioners were installed in October, 2025. The community of Southbay offers a deep marina to handle just about any size boat. Southbay is an active community with many social, sports and boating activities. The remodeled clubhouse is the heartbeat of the community including a fitness room, game room, two kitchens, card room, ball room, elevator, even a baby grand piano! Southbay is located in a convenient and central location just a short drive to several area beaches, shopping, restaurants, downtown Venice or Sarasota. The famous Casey Key Fish House and Tiki Bar are close by - an easy golf cart ride away. This home is ready for you to start living the vibrant Southbay lifestyle!

431 Yacht Harbor Drive, Osprey

$817,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Experience refined waterfront living in Southbay, one of the area’s most coveted boating communities. This impeccably maintained three-bedroom pool residence offers a thoughtful, split-bedroom design that balances privacy with seamless flow—ideal for both relaxed everyday living and sophisticated entertaining. A comprehensive renovation in 2017 elevated the home with cohesive flooring throughout, fully redesigned spa-inspired bathrooms with custom vanities, updated ceilings, recessed lighting, and interior shaker doors. The home was also re-piped for water and sewer, offering both modern comfort and long-term peace of mind. The light-filled living room, accented with elegant shiplap detail, opens effortlessly to the lanai, creating a graceful indoor-outdoor connection. Outside, a private retreat awaits with a resurfaced pool, new screen enclosure, and marble pavers. Generous covered space accommodates lounging, dining, and entertaining, while sliding doors from the primary suite, living room, and family room invite the outdoors in and enhance the home’s open, airy ambiance. The primary suite is a serene escape, thoughtfully positioned for privacy and direct access to the lanai. Custom closet systems throughout the home provide elevated functionality, while the epoxy-finished garage with built-in cabinetry delivers a polished, organized finish. Mature tropical landscaping and six-foot pitch apple plantings create a secluded backyard sanctuary, complemented by stately palms that frame the home with unmistakable Florida elegance. Southbay offers a distinguished, resort-style lifestyle with a newly renovated waterfront clubhouse featuring a grand ballroom, catering kitchen, and state-of-the-art fitness center overlooking the marina. Residents enjoy a heated pool, youth pool, tennis and pickleball courts, shuffleboard, bocce, basketball courts, walking trails, and an Intracoastal waterfront park. For boating connoisseurs, the community-owned deep-water marina provides direct Intracoastal access with no fixed bridges to the Gulf. Exclusive, low-fee boat slips accommodate vessels up to 55 feet and are available only to Southbay owners. A vibrant social calendar and golf-cart-friendly streets make it effortless to enjoy community events, nearby boutiques, waterfront dining, and local beaches. Ideally located near Pine View School—Florida’s #1 charter school and one of the nation’s premier gifted programs—this residence presents a rare opportunity to enjoy luxury living within an active, waterfront enclave. A sophisticated coastal retreat where lifestyle, privacy, and boating converge—welcome to Southbay.

1486 Landview Lane, Osprey

$1,100,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

**IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** offers 3 BEDS, 2 FULL and 1 HALF BATHS plus STUDY/DEN – and is nearly 100% SOLAR-POWERED (details available)! This Custom and Updated home offers many premium features including elegant Bolivian woodwork, beautiful tile floors throughout, Expansive Kitchen with Hardwood Cabinets, Granite Counters and Stainless Steel Appliances. The Spacious primary bedroom suite offers multiple walk-in closets and even a BONUS ROOM (possible Gym, Nursery, etc.) while the primary bathroom includes dual sinks, spa tub and custom-tiled shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Solar-Heated Pool (Resurfaced in 2021) and ample entertaining space in a private and serene setting. With its HIGH ELEVATION (and NO FLOODING concerns during recent hurricanes and NO storm Damage), this residence is situated on an Oversized, Cul De Sac Lot with Circular Driveway, has wonderful curb appeal and an Ideal SOUTHERN Rear Exposure! Recent UPDATES include NEW ROOF, NEW HURRICANE IMPACT WINDOWS & SLIDING DOORS, NEW LANAI CAGE and Much More! SOUTHBAY YACHT & RACQUET CLUB is a BOATING COMMUNITY with a 170 Boat MARINA, Clubhouse, Tennis and Pickleball Courts! SOUTHBAY is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

219 Keel Way, Osprey

$925,000

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

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.

1602 Southbay Drive, Osprey

$1,025,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Attention water lovers... take a look at this home in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball courts, and kayak storage. Residents also enjoy a waterfront park and nearly 20 acres of common grounds with miles of walking trails. A true highlight is the gorgeous geothermal pool, which showcases stunning marina views and is a must-see when visiting Southbay! Now that you’ve fallen in love with the community, are you ready to explore this spectacular home that’s waiting to be yours? This spacious residence, spanning over 3,000 square feet, welcomes you with a brick-paver driveway and lush, mature landscaping along the front walkway. Continue through the gated entry to discover the tranquil sound of a soothing water feature before stepping inside. The interior boasts beautiful views of the pool and lush green landscape, hard flooring throughout, and a layout designed for both everyday living and effortless entertaining. The floor plan includes two distinct family rooms, one with a cozy fireplace, wet bar, and beverage refrigerator, and the other offering beautiful views of the pool. The primary bedroom includes an additional room with pool views, ideal for an office or exercise space...the choice is yours. A spacious laundry room, complete with a double desk and abundant storage, adds to the home’s functionality. Outside, the large lanai features a beautiful pool and provides generous covered areas, and plenty of open space for sunbathing under the clear blue sky. Recent updates include a new roof installed in 2023 and a recently refinished and resurfaced pool. The location is equally appealing, just minutes from a variety of restaurants and shopping, convenient highway access, and the soft, powdery sands of Southwest Florida's Gulf Beaches. I welcome you to visit this home... come see, come sigh, and make it your own!

1218 Yacht Harbor Drive, Osprey

$649,000

Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Do not miss your opportunity to build your dream home in the amenity-rich, waterfront community of Southbay Yacht and Racquet Club! This lot is only a short walk away from 10,000 square foot newly renovated clubhouse that overlooks the Southbay marina. The Power & Sail Club hosts events like potlucks, lunch cruises, and picnics. Boat life not for you? At Southbay Yacht and Racquet Club, you will find pickleball, tennis, bocce and shuffleboard courts, plus the Southbay Social Committee hosts and organizes block parties, holiday parties and more. When you build here, you will be conveniently located between downtown Sarasota and downtown Venice giving you multiple options dining and entertainment. Don't miss out on this unique opportunity for a new construction build in Southbay Yacht and Racquet Club.

Four Knot Lane, Osprey

$1,200,000

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coast’s most coveted communities—where every day feels like a vacation! Southbay boasts a world-class private marina with 172 deep-water slips, accommodating yachts up to 55 feet, along with personal watercraft and kayaks. Slip rentals are available and offered at a highly competitive rate, making this an exceptional value for boating enthusiasts. This remarkable residence is one of the largest in the community and offers a rare 3-car, side-load garage with a dedicated workshop—perfect for collectors, creatives, or anyone in need of additional space. Step outside to your private oasis: a peaceful lanai overlooking a sparkling, heated pool and spa—ideal for both lavish entertaining and quiet moments of retreat. Inside, every detail has been meticulously curated. A recent, designer-led renovation has transformed the home into a sophisticated showplace. The interiors reflect a timeless elegance, with a high-contrast black and white palette that creates a dramatic yet harmonious flow throughout the home. Clean lines, thoughtful textures, and classic materials elevate each space with effortless style. A reimagined front entrance welcomes you into soaring ceilings and a stunning great room filled with natural light. The gourmet kitchen is equally impressive, featuring white solid wood cabinetry with soft-close drawers, stainless steel appliances, and gleaming granite countertops—all designed with both beauty and functionality in mind. With two expansive living areas, oversized bedrooms, two en-suites, and multiple storage options, this home provides ample space for elegant living and entertaining. Southbay also offers a newly renovated clubhouse, resort style heated community pool, tennis courts, pickleball courts, miles of walking trails & green space, and a full calendar of vibrant social events year-round. The community is warm, welcoming, and lively—perfect for families and those who enjoy an active, coastal lifestyle. Conveniently located next to Publix, shops & restaurants. Across the street from Oscar Scherer State Park, and only 5 minutes to the number 1 school in the state-Pine View. This is not just a home; it is a statement of style, comfort, and grace. Come and experience the elevated lifestyle that only Southbay Yacht & Racquet Club can offer.

1484 Seafarer Drive, Osprey

$1,100,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

This meticulously cared for John Cannon home is an exceptional opportunity to enjoy the desirable Southbay lifestyle in a newer 2013 built home. With raised, 10-foot tray ceilings, crown molding, millwork, plantation shutters, wood plank style tile floors, and a whole house Sonos sound system, this well-designed split floor plan includes 3 bedrooms (2 en-suite and a separate 3rd bath) and a study with built-in shelving. New interior and exterior lighting and fresh interior paint updates this home. The outdoor kitchen area is directly plumbed to the 500 gallon buried propane tank. Peace of mind features: This home has had annual roof inspections, maintenance and cleanings, twice a year whole house generator inspections, regular HVAC and pool, irrigation and tree maintenance. It has hurricane impact-rated windows, a whole house Generac generator, wireless, monitored security, concrete block construction, a barrel tile roof, paver deck and driveway, and high elevation which is not in a flood zone. Recent updates in 2022: New salt cell for pool and spa, new carpet in bedrooms. New in 2023: Trane HVAC system, automatic filler for pool, and Wi-Fi controllers added for pool & spa, irrigation, thermostat. New in 2024: Pool pump, Rinnai circulating on-demand hot water heater, rescreened lanai, refreshed landscaping. Southbay Yacht & Racquet Club is a remarkable community offering unrivaled, yet affordable, amenities. The stunning three level clubhouse features a fitness room, card room and two kitchens for private events. Residents enjoy a heated community pool overlooking the deep-water marina with boat docks, for the exclusive use of Southbay owners, pickleball & tennis courts, shuffleboard courts, bocce ball, basketball courts, kayak storage, a waterfront park and nearly 20 acres of common grounds with miles of walking trails. All of this, in a super convenient location near shopping, restaurants, beaches and the vibrant cities of Venice and Sarasota. Everything the Florida lifestyle has to offer can be found right here!

229 Lookout Point Drive, Osprey

$1,050,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Southbay Yacht & Racquet Club, The waterfront Community with Resort-Style Amenities. Welcome to this beautiful three-bedroom two-bathroom home featuring a private pool and spa, perfect for relaxing or entertaining year-round. Located in a highly sought-after waterfront community, this property offers access to a private marina, clubhouse, community pool and scenic park-ideal for enjoying the coastal lifestyle! Whether you're boating, swimming, or just soaking up the sun, this home brings the vacation living to your front doorstep. Walk, bike, or take your golf cart to restaurants, shopping, tiki bars and parks which are all nearby. Don't miss your chance to own a piece of Paradise! Professional photos coming soon.

142 Dory Lane, Osprey

$1,020,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Welcome to the much sought after Southbay Yacht and Racquet Club!!! You can be on vacation all year long with the private marina that has 172 boat slips that can accommodate yachts up to 55 feet. This one of a kind private marina will also accommodate personal water crafts and kayaks too!!. Our boat slip rentals are based on availability with a very attractive quarterly fee as compared to other boat basins. This lovely 2909 sq. foot 3 bedroom home, with an office or bonus room and 3 full baths are mere steps away from the marina and intercoastal waterway along with our lookout point park. The new owner will love this 3 car oversized side load garage! Beautiful private lanai with large heated pool and spa. The home has many new appointments. (More detailed information will be in the home.)...For example, hurricane rated windows and hurricane rated double front doors. The rear french doors are protected with pull accordian shutters that will also protect your lanai furniture, without moving it. Many new upgrades, High ceilings in great room and kitchen. Newly installed flooring in great room , dining room, and bedrooms. Gourmet kitchen with many cabinets and 36" Southbend 6 burner professional gas range and oven. In addition a built in Bosch convection oven. You must see this home to appreciate all of the extras. In addition, Southbay has a lovely updated clubhouse with pool, tennis and pickle ball courts, bocci ball and shuffleboard. We have mens and womens, groups activities along with many social parties thru out the year. And we haven't forgotten the young ones! A very social and friendly neighborhood or private if you like.

284 Lookout Point Drive, Osprey

$1,150,000

2 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

In the sought-after Southbay Yacht & Racquet Club, one of the premier boating communities on the southwest coast of Florida, this stunning home offers the ultimate in luxury living. With a community-owned marina and an expansive open layout, this property creates an ideal setting for relaxation and entertaining. This updated residence boasts volume ceilings, two fireplaces, built-in cabinetry and PPG tempered glass windows, all adding to its impressive design. The expansive covered lanai and pool area, accessible from the living room, primary suite and family room, is the space for outdoor entertaining, grilling and enjoying Florida’s beautiful weather. The kitchen features elegant stone countertops and a charming breakfast area that flows seamlessly into the family room. Travertine tile throughout adds an extra touch of sophistication, while the spacious rooms have comfortable, inviting atmosphere. The primary suite serves as a retreat, with a sitting area that overlooks the pool, a walk-in closet and a reach-in closet. The en-suite main bath offers a walk-in shower, dual vanity sinks and plenty of space for relaxation. The guest bedroom is equally spacious and provides a private, welcoming space for family or guests. The home is complete with a two-car garage, brick-paver circular driveway and mature landscaping, enhancing its curb appeal. Move-in ready and full of potential, the home also offers the opportunity to expand, consider adding a second floor to capture stunning water views or personalize it to fit the needs of a growing family. Southbay Yacht & Racquet Club is an exceptional community offering unrivaled amenities. The newly renovated clubhouse features a fitness room, card room and two kitchens for events. Residents can enjoy a geothermal pool with marina views, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball courts, kayak storage, a waterfront park, and nearly 20 acres of common grounds with miles of walking trails. This home provides a blend of luxurious living and an active, vibrant lifestyle in one of Florida’s sought-after communities. Don't miss your opportunity to make it yours!

327 Sea Anchor Drive, Osprey

$945,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

New to the market, your dream home awaits in the exclusive private marina community of Southbay Yacht and Racquet Club. For boating enthusiasts, this is the opportunity you’ve been waiting for! In the sought-after Southbay Yacht and Racquet Club, this stunning residence combines spacious design with the best of Florida living, just steps from your boat. Imagine waking up and stepping out onto your two-story screened lanai, where you can unwind beside your oversized pool and watch the boats sail by. Inside, natural light fills the open-plan living spaces, highlighting high ceilings and expansive windows that create a warm, inviting atmosphere. The open kitchen and family room are ideal for preparing meals and enjoying quality time with family and friends, while the large dining room and sunken living room provide an elegant setting for special occasions. The main floor also offers two bedrooms and baths, ideal for family or guests. The private second-floor primary suite is your personal retreat, with a quiet library and balcony offering serene views of the pool and surrounding nature. Recent updates in 2025 include a new roof, GE Monogram refrigerator and a new air-conditioning system. Whether you're lounging by the pool or relaxing in your screened lanai, this home is move-in ready. As a resident of this boater's paradise, you'll have access to a private marina, clubhouse, fitness room and community pool. The community park offers stunning waterfront views, and you're just minutes from top-rated schools, shopping, dining and a state park. Don't miss the chance to experience this exceptional waterfront lifestyle.

128 Sea Anchor Drive, Osprey

$670,000

4 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Within the much sought after community of Southbay Yacht & Racquet Club, you will find this wonderfully maintained home that features classic Florida details often missing in new builds today. This home, spanning 2,513 square feet, is a testament to the traditional Florida lifestyle with a touch of modern convenience. The property boasts 4 spacious bedrooms, 3 full bathrooms, ensuring ample space for family and friends. The true split floorplan ensures maximum privacy for the owner and their visitors. Upon stepping through the grand double door entry, you are immediately greeted by tall ceilings that create an expansive and airy ambiance. The formal dining room sets the stage for elegant dinners and gatherings, while a welcoming view straight out to the lanai space and the grand freshwater pool captures your attention. The family room is a central point of the home, featuring bright vaulted and beamed ceilings that draw your eye to the working gas fireplace. This area flows seamlessly into the breakfast area and the kitchen, which is equipped with new stainless-steel appliances, making it an ideal space for culinary enthusiasts. The home's layout is thoughtfully designed, with 2 bedrooms and a shared bathroom with pool access situated in one wing. This wing also offers 2 sets of sliders that lead to your outdoor wet bar and kitchen area, perfect for entertaining. On the opposite wing, you will find the owner's suite. This private retreat features sliding doors to the pool area, an ensuite bathroom with soaring ceilings, a spa tub, a glass-enclosed shower, and dual vanities. The entire home has been freshly painted, including the interior of the 2-car attached garage. Numerous extras contribute to the home's appeal, such as storm shutters, tinted windows for energy efficiency, and a full-home Generac Generator installed in 2022. Southbay Yacht & Racquet Club is a community known for its exceptional amenities. The 7-acre deep-water basin accommodates kayaks, jet skis, sailboats, powerboats, catamarans, and yachts up to 55 feet, making it a boater's paradise. Additional amenities include a geothermal heated pool, a youth pool, a covered outdoor patio, three tennis courts, four pickleball courts, two shuffleboard courts, a youth basketball court, a playground, kayak storage, and a waterfront park. The community also boasts 20 acres of common ground with five miles of winding sidewalks in a picturesque, park-like setting. With its prime location, traditional Florida charm, and modern amenities, this home in Southbay Yacht & Racquet Club offers a unique blend of comfort and luxury. It is more than just a place to live; it is a lifestyle waiting to be embraced.

1426 Landview Lane, Osprey

$880,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

A Southbay Yacht & Racquet Club beauty! This home has been given meticulous care and offers an abundance of updates and upgrades. Popular Southbay community features a boating marina on the Inter coastal Waterway, making this one of the most sought after locations west of the trail! This airy and open floorplan is sure to please! There are so many delightful updates and improvements, I'll try to list them all...here goes! HURRICANE IMPACT WINDOWS, FRONT ENTRY DOOR WITH SIDE GLASS PANELS, SLIDIN GLASS DOORS AND GARAGE DOOR INCLUDING INTERIOR DOOR LEADING TO THE GARAGE AND THE SIDE DOOR LEADING OUT! THE SPACIOUS GREATROOM OPENS TO UPDATED KITCHEN WITH QUARTZ COUNTERTOPS AND OVERSIZED QUARTZ PENINSULA * INDUCTION COOKTOP * RANGEHOOD* CUSTOM BACSPLASH * BUILT-IN STAINLESS STEEL OVEN, MICROWAVE AND WARMING DRAWER * S/S REFRIGERATOR * NEW S/S DISHWASHER IN 2022 * NEW DUAL ZONE WINE REFRIG IN 2022 * KITCHEN SINK EQUIPPED WITH PENTAIR EVERPURE WATER FILTRATION SYSTEM. UPDATED BATHROOMS WITH NEW SINKS, FAUCETS, VANITIES, TOILETS AND MIRRORS * MASTER BATH WITH OVERSIZED SHOWER WITH CUSTOM TILING AND FRAMELESS SHOWER DOOR * GUEST BATHROOM WITH NEW FRAMELESS SHOWER DOOR AND NEW BUILT IN LINEN CABINET * CUSTOM HUNTER DOUGLAS WINDOW TREAMENTS THROUGHT THE HOME WITH ROOM DARKENING SHADES IN THE PRIMARY BEDROOM * MOTORIZED SHADES IN THE GREATROOM * NEW MINKA AIRE REMOTE CONTROLLED CEILING FAN IN THE PRIMAY BEDROOM * NEW CUSTOM CLOSET SYSTEMS * ALL SOLID CORE BEDROOM AND CLOSET DOORS * NEW A/C UNIT IN 2022 WITH ALL AIR VENTS SANITIZED AND ALL NEW VENT REGISTERS INSTALLED * ROOF WAS INSTALLED IN 2005 SO THE SELLER JUST HAD THE ROOF HIPS AND RIDGES REINFORCED WITH TILE ROOF MORTAR IN DECEMBER 2024 WITH A ONE YEAR WOKMANSHIP WARRANTY * NEW ELECTRICAL PANEL INSTALLED 2021 * THE HOME WAS REPLUMBED AND WATER HEATER REPLACED IN 2012 * THE OVERSIZED POOL WAS INSTALLED IN 2021 * CUSTOM HEATED SALT WATER POOL HAS GLASS TILES WITH CASCADING WATER FEATURE AND OVERSIZED SPILL OVER SPA WITH TURBO JETS, REMOTE CONTROLLED HAYWARD POOL EQUIPMENT * TRAVERTINE TILE LANAI FLOOR * POOL CAGE WITH OVERSIZED GUTTERS AND DOWNSPOUT * FRESHLY PAINTED AND NEW MINKA REMOTE CONTROLLED CEIING FAN * PRIVACY LANDSCAPING AND LANDSCAPING STONE, PAVERS AND ACHITECTURAL ROCKS. EPOXY/POLYASPATIC GARAGE FLOOR * BLOWN IN R-38 INSULATION IN HOUSE AND GARAGE ATTIC * 5" SEAMLESS GUTTERS WITH FRENCH DRAINS * NEW LED CEILING LIGHTS WITH DIMMER SWITCHES * STYLISH PORCELAIN TILE THROUGHOUT. Wow! That is a lot of updates making this home ready to move right into and start enjoying the Florida lifestyle and all that Southbay has to offer. Community features include tennis and pickleball courts, clubhouse with fitness center, card room, ballroom, community pool and marina, playground, bocce ball courts, kayak launch. Boat slips and PWC slips are available for residents only with a low lease fee making Southbay a very desirable boating community. No boat - no problem! Southbay is a very active community with many clubs and social events for all ages. Conveniently located between Sarasota and Venice with shopping, dining, beaches and more, close a hand.

1237 Flying Bridge Lane, Osprey

$645,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Peace of Mind & Prime Location! Nestled in the sought-after Southbay Yacht & Racquet Club—a premier waterfront community with its own 170-slip marina on the Intracoastal—this high-elevation home (18+ ft, Flood Zone X – no flood insurance required!) offers exceptional value and lifestyle. Impact-Rated Windows, New Roof (2023). Priced Below Recent $780K Appraisal (available on request), this 3-bed, 2-bath corner-lot home with southern exposure features numerous upgrades: new roof, gutters/downspouts (2023), impact windows, impact-rated garage door, fresh exterior paint, refinished garage floor, and whole-home re-plumbed. Inside: tile flooring throughout, stainless steel appliances, large primary suite with custom shower, and spacious guest rooms. Outside: mature tropical & exotic fruit trees. Community amenities include clubhouse, tennis & pickleball, and proximity to Pine View School, Legacy Trail, beaches & more!

1212 Windward Drive, Osprey

$3,335,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a 6-foot depth at mean low tide, the marina can accommodate 175 boats owned by its residents. In Southbay, the HOA fees are only $612 per quarter, and it's so affordable to keep your boat in a slip, that includes water and electric. With Sarasota Bay in the backyard and the marina within walking distance of your front yard, this property is one of only 17 direct waterfront lots in the subdivision. And the property will allow for a new boat dock and lift to be installed. Inside this renovated home you’ll find three bedrooms, three full baths, a spacious living and family room, along with a heated pool and spa. Plus, there’s a large brick paved sundeck with dramatic views across Little Sarasota Bay and Casey Key. Although the residence has been updated and is move-in ready, you may also consider renovating the home and adding a second floor or building an entirely new home on the half-acre waterfront lot. Southbay Yacht & Racquet Club features a newly renovated clubhouse that overlooks the marina. Inside, there’s a 99-person ballroom with catering kitchen and dance floor, community room with kitchen, piano and entertainment area, a fitness room with aerobic and strength training equipment, a card room, library and meeting room. The community also has a geothermal heated pool, a youth pool, covered outdoor patios with furniture, three tennis courts, four pickleball courts, a bocce ball court, two shuffleboard courts, basketball court, kayak storage area, a waterfront park, 20 acres of common ground and three miles of winding paved walking trails. The development is golf-cart friendly and the community hosts weekly, monthly and multiple annual events, plus there’s even a Power and Sail Club. You’ll love living in this waterfront home and this special community where there’s something for everyone.

419 Yacht Harbor Drive, Osprey

$999,500

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. Updated with a spacious, open layout, this pool home boasts many features that set it apart from others. The great room is expansive with an attractive electric fireplace and ultra-high ceilings. Adjacent to it is a custom kitchen with quartz countertops and a large dinette area. The living room is also impressive, with high ceilings and sliding glass doors that open to the lanai. The dining room, which can accommodate a table for 10, overlooks the front patio. The primary bedroom offers sliding doors that open to a spacious lanai with a large inground pool. The primary bathroom features a soaking tub with jets, dual sinks, and a roomy walk-in closet. Southbay Yacht & Racquet Club is a premier marina community with a newly renovated clubhouse offering numerous amenities, including a fitness room, card room, and two kitchens for events. The community has a geo-thermal pool overlooking the marina, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball, kayak storage, a waterfront park, and nearly 20 acres of common grounds with miles of walking trails. This house is a unique treasure, perfect for someone wanting to live in an exceptional home within an exceptional community!

146 Yacht Harbor Drive, Osprey

$3,525,000

5 Beds ⋅ 5 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida’s Gulf Coast where boats are accommodated in a deep-water marina for low fees. Boasting over 135 feet of water frontage and surrounded by lush tropical landscaping and majestic Royal Palms. Its refined curb appeal sets it apart as a one-of-a-kind property. The custom John Cannon home features a grand double door entry that opens to breathtaking wide open bay views. Inside, the home showcases high-end finishes and upgrades, including impressive, vaulted ceilings reaching up to 21 feet. You'll find abundant crown molding, elaborate tray ceilings, and exquisite wall finishes adorned with artfully painted faux designs and plantation shutters throughout. The home is designed for entertaining, with a full bar and wine room for guests, as well as an upper-level wet bar. The chef's kitchen is a culinary dream, featuring a spacious granite island, a gas cooktop with a pot filler, and views overlooking the pool, patio and bay. An upper-level bonus room offers versatile space for play, music, movies or exercise, all while enjoying some of the best views in the house. The main level primary suite is a serene retreat with a sitting area, two large closets and a luxurious bath that includes a garden shower, large tub, dual sinks, and a separate toilet and bidet. The expansive outdoor living spaces, including main level and upper terraces, are ideal for enjoying sunsets and observing local wildlife such as ospreys, dolphins, manatees and a parade of boats. Private dock for sunset viewing and fishing. Ideally between Sarasota and Venice, this residence is just minutes from the pristine sands of Siesta Key and Nokomis Beach. Convenience abounds with nearby shopping, dining the Legacy Trail, private and commercial airports, and top-rated schools, including the renowned Pine View School. This exquisite home embodies the essence of Florida living. Southbay Yacht & Racquet Club lives up to its name with a newly renovated community clubhouse, geothermal pool, gym overlooking the marina, banquet rooms, three tennis courts, four pickleball courts, a bocce ball court, two shuffleboards, basketball, kayak storage area, a waterfront park, 20 acres of common grounds and miles of trails. Ideally in between culturally rich Sarasota and charming Venice, minutes to beaches, Legacy Trail, No. 1 rated Pine View School, shopping, waterfront restaurants and Oscar Scherer State Park. Walk to your boat or take your golf cart around the neighborhood. For those who seek an exceptional waterfront life, nothing compares.

275 Lookout Point Drive, Osprey

$1,050,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

No hurricane problems here! impact windows and storm curtains on the lanai helped to keep this home safe. Also located in an X flood zone! This beautiful home located in "west of the trail", Southbay Yacht and Racquet Club is a very sought after location. One of the few communities with it's own marina and very reasonable dock rental fees only available to homeowners in the community. This home as been renovated and updated inside and out and offers warmth and charm just perfect for a coastal community. Southbay offers a lively community with actives for all ages. Plus walking paths, playground, kayak launch and storage, community pool, jet ski slips, tennis and pickleball courts, bocci ball, fitness center and a renovated clubhouse perfect for all the activities that are offered. The large marina off the ICW will accommodate just about any size boat. Lookout Point Park is the perfect place to watch the sunset over the intracoastal waterway. the amenities in this home are plenty! HURRICANE RATED WINDOWS ON THE FRONT AND SIDE WERE INSTALLED 2007. HURRICANE SHADES IN LANAI PROTECT ALL REAR SLIDING GLASS DOORS, The expansive LANAI RENOVATED IN 2022 and features a 4" extension on the back and side, new screen enclosure with full-view, new pavers and pool tiles along with custom waterfall bowls. Plus an outside patio area perfect for your grill. Inside the home renovations include decorated coffered ceiling in the greatroom and dining room, bump-out bay in the greatroom, custom kitchen including Fisher Paykel double dishwasher, Sub-zero refrigerator, Wolfe cooktop, built in oven and microwave, wine cooler, breakfast bar area plus a center island. Plenty of room for casual dining opens to the greatroom plus a formal dining room with sliding glass doors o the lanai. Two of the three sliding glass doors have full extension pockets lining glass doors - perfect for letting the outdoors in and make for a large entertaining area. The kitchen window also telescopes back to open completely - another great entertaining feature. Just off the master bedroom is an extra large bonus room currently used a s a music room. This space has endless possibilities such as a quiet retreat for an office and private lounge area, a workout room, extra sleeping are for guests...just use your imagination and enjoy the extra space! Also included is a spacious 12x11 utility room with epoxy floor, a great space that is your Florida basement! The wide double doors from the utility room lead to the outdoors and make a separate entry into the bonus room. or could be used as a golf cart storage area. MAIN LIVING AREA PAINTED 2023, UNDERGROUND SEWAGE PIPES RE-LINED 2022. FULL HOUSE HVAC REPLACED 2010 AND REFURBISHED IN 2020. MOST OF THE ROOF REPLACED 2010, located on a cut-de-sac street with the walking path behind the property. The sellers have taken meticulous care with the landscaping and is a delight to see! The Southbay location is convenient to both downtown Venice and Sarasota, shopping, restaurants and major roads. No CDD fee! Also close to renowned Pineview School. Come take a look for yourself and see why this home in Southbay may be just what you are looking for!

247 Keel Way, Osprey

$1,300,000

3 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Welcome to BOATERS PARADISE and this stunning OVERSIZED CORNER-LOT pool home with breathtaking WATER VIEWS of the private deep-water marina in the highly sought-after Southbay Yacht & Racquet Club. This expansive residence boasts three bedrooms, a possible FOURTH bedroom (currently used as a den), four bathrooms, and a bonus room, all situated on a corner lot with a circular drive and a side-entry garage with a second driveway. Step inside to a spacious foyer that leads to a voluminous living room featuring a gas fireplace and marina views. The open floor plan seamlessly connects the living area to a large dining room, making the marina view a focal point of every gathering. The kitchen is a chef’s dream, equipped with a custom Godin gas range with a warming drawer and hood, granite countertops, Brazilian wood cabinetry, and a large center island with a breakfast bar. The adjacent family room and eat-in kitchen area provide multiple access points to the lanai, blurring the lines between indoor and outdoor living. The master suite is a private retreat with lanai access, a walk-in closet with custom wood built-ins, and an ensuite bathroom featuring dual split vanities, granite countertops, and a large step-in shower. The additional bedrooms are equally spacious, with ample storage and natural light. Bedroom two features a built-in wall unit and double closets. Bedroom three features an ensuite bathroom, walk-in closet, and an additional room that has endless possibilities. The den, with its wall of windows overlooking the marina, is perfect as a man cave with a custom bar area that enhances its entertaining potential, can be used as a home office or easily converted into a fourth bedroom. This room also has direct access to bathroom four. Outdoor living is redefined in the pavered patio area, complete with a tiki entertainment center, cozy firepit, and lush tropical landscaping for ultimate privacy. The home is designed for family living and is ideal for multi-generational living. Recent updates include a new roof and pool solar panel system (2023) and freshly painted interiors in neutral tones, making this home worry-free and energy-efficient. Southbay Yacht & Racquet Club is an exceptional boating community with slips available on a first-come, first-serve basis at a LOW RENTAL FEE. The community offers a LOW HOA, NO CDD, and a wealth of amenities including a kayak launch and storage area, updated clubhouse, tennis, pickleball, community pool, shuffleboard, bocce ball, basketball, playground, and miles of scenic walking paths. Located just minutes from top-rated schools, beaches, the Legacy Trail, and the best of Sarasota and Venice. Don’t miss this rare opportunity to own a slice of paradise in one of the most desirable waterfront communities!

322 Yacht Harbor Drive, Osprey

$975,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

This quintessential Spanish Mediterranean mini estate will immediately wow you as you drive up the bricked driveway, open the wrought iron gated entry to the exquisite arched Roman front door creating the old world ambience. Entertain in this meticulously maintained home with a light & bright open floor plan where cathedral ceilings showcase the dining & living areas, the stunning kitchen with wood cabinetry, granite tops & ceramic tile floors. Or choose to entertain around the covered space where the heated pool & spa are surrounded by attractive arches & a bricked border with fruit trees. The ensuite primary bedroom has engineered hardwood flooring & a walk-in cedar lined closet. The bathroom has a marble lined shower & marble countertop with dual sinks & elegant fixtures. The split plan includes the primary bedroom at one side of the home & the 2 large guest bedrooms with walk-in, cedar lined closets at the opposite side. One guest bedroom has a half bath. The main bathroom is filled with natural light that brings the outside in yet maintains privacy. You will find ample storage throughout. A large wet bar provides another special entertainment area! The enormous family room inclusive of cathedral ceilings with wood beams & a fireplace adds to that old world ambience & spacious feel. There is a large bonus room that inspires imagination & endless possibilities! The home is equipped with a whole house Generac generator to be assured you will be safe, secure & always have the amenities you need. This residence is located in the convenient & sought after community of Southbay Yacht & Racquet Club where you are able to dock your sailboat, powerboat, catamaran or yacht up to 55 feet in the 7 acre deep water basin. You can drive your golf cart to the attractive newly renovated fully equipped clubhouse including a state of the art fitness room with aerobic & strength training equipment. Other amenities include a geothermal heated pool, sports courts, and so much more. There are 20 acres of common ground with 5 miles of winding sidewalks in a park-like setting. Some of the close proximity local attractions are nearby beaches, golf, shopping center, Pine View School, Oscar Scherer State Park, Legacy Trail, waterfront restaurants, cultural attractions & easy access to US 41 and I 75. And...Historically low HOA fees! Make sure to see the attached video (make sure to turn the volume on) of the community Southbay Yacht & Raquet Club where this lovely home is located.

209 Keel Way, Osprey

$900,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

This is an outstanding Southbay residence, the best-kept secret on the Gulf Coast where boats are accommodated in a deep-water marina for low fees. Numerous recent upgrades and finishes. Inviting paver drive, oversized 22-by-24-foot garage and double-door entry welcomes you to a home that is simultaneously tranquil and energizing. Custom crafted throughout with a wood fireplace that is centered on the great room with 10-foot beamed/vaulted ceilings and new luxury vinyl floors. Overlooking the sparkling newly resurfaced heated pool and the lanai with so many areas to perfect the art of outdoor living. The sleek-modern galley kitchen is stainless and granite. Spacious main level owner's suite has patio access, a walk-in closet, dual sinks, soaker tub, toilet and shower. Additional rooms on the main level include den/office (which easily could be a 4th bedroom) with patio access, large storage room or use as an additional office and powder room. The upper level has an ideal layout with two bedrooms, a bonus room and full bath, which has their own private stairway to the pool below. There is a 10-by-8-foot balcony which overlooks the park, tennis courts and marina. Roof was replaced in 2016 and both air conditioners in 2023. Southbay Yacht & Racquet Club lives up to its name with a newly renovated community clubhouse, geothermal pool, gym overlooking the marina, banquet rooms, three tennis courts, four pickleball courts, a bocce ball court, two shuffleboards, basketball, kayak storage area, a waterfront park, 20 acres of common grounds and miles of trails. Ideally in between culturally rich Sarasota and charming Venice, minutes to beaches, Legacy Trail, No. 1 rated Pine View School, shopping, waterfront restaurants and Oscar Scherer State Park. Walk to your boat or take your golf cart around the neighborhood. For those who seek an exceptional waterfront life, nothing compares.

1321 Southbay Drive, Osprey

$875,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Priced below bank appraisal of $1,000,000! Located in the premier neighborhood of Southbay Yacht and Racquet, this home has been thoughtfully updated leaving you with minimal maintenance so you can truly enjoy all that fun there is to have with the many amenities this development has to offer. This property is move-in ready. With a newer roof, hurricane impact windows and all up to date plumbing, you have little to worry about. Rest easy knowing that the property is located out of the flood zone. Enjoy the privacy of the backyard created by lush landscaping and a privacy wall. The elevated ceiling and many windows provide an open, airy feel. The layout of the home offers a split floor plan with the Primary suite on one side of the house and two bedrooms and another bath on the other side. One of the few deep water marinas on the west coast of Florida is the heart of Southbay. Dock slips are available at very low rates for Southbay homeowners. Current rates are between $45-188/Mo. (paid quarterly). The Marina accommodates boats up to 65' including Sailboats. Play until your heart’s content with a myriad of opportunities that Southbay has to offer: boating with neighbors, pickleball, tennis, kayaking, bocce ball, shuffleboard or participate in the many social events hosted at the newly renovated clubhouse. Move in, hop on your boat and enjoy a sunset cruise any night of the week. Southbay offers the active Florida lifestyle you'll love.

1251 Windward Drive, Osprey

$725,000

3 Beds ⋅ 2 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

As you enter a welcoming courtyard, you will feel at home. Perfectly situated on a quarter acre elevated lot, this 3-bedroom 2-bath residence has been beautifully maintained. A large foyer leads you to the spacious Great room with fireplace. A large dining room adjacent with sliders leading to a private fenced courtyard. The updated kitchen offers wood cabinets, stainless appliances, pass through and French door to lanai. The primary suite has an updated bath with large tiled walk-in shower, double vanities, wood cabinets, and granite counters. Large walk-in closet and sliders to pool. Two generous size additional bedrooms, one with built in murphy bed and custom built in desk area. New pavers accent the sparkling resurfaced pool. A large covered screened lanai provides a wonderful place to welcome your guests for entertaining. Large two car garage w/ built in cabinets. Lush tropical landscaping. 7-acre marina accommodating up to 55’ sails to power boats. A newly renovated 10,000 sq ft clubhouse with ballroom & catering kitchen, fitness center, card room, library, heated pool, 3 tennis courts, 4 pickle ball courts, 2 shuffleboard courts, a bocce court, playground, waterfront park, & kayak storage with over 5 miles of walking trails. On site management. Truly a boater’s paradise. Come live your dream in one of Sarasota’s best communities.

188 Dory Lane, Osprey

$1,350,000

5 Beds ⋅ 5 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Bring your boat and your large family to this beautifully remodeled, 5 bedroom, 5 full bath contemporary home located in sought after Southbay Yacht and Racquet Club. When you first walk in, you'll immediately notice how bright and vibrant the open plan is as natural light fills every space from the extensive windows and high ceilings. Your whole family can enjoy cooking together in the chef's kitchen with dual ovens. Stay in shape swimming laps in your expansive private SWIMMING pool. Then relax in your private outdoor jacuzzi while listening to the mature bamboo sway just outside your enormous pool cage. On the rare days that it's too chilly for a swim, come sit by your fully functional wood burning fireplace with a stunning two story coral chimney. The primary suite is upstairs for privacy and quiet so that you can enjoy your jetted, deep soaking tub in peace. There is so much to do here with out ever leaving your community, a deep water marina with slips for your boat, pickleball, tennis, a fitness center, a basketball court, a clubhouse, and walking paths for you and your pets. The cherry on top is that the nationally recognized Pine View School is just up the street from this amazing home.

337 Passage Way, Osprey

$1,275,000

4 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Picture yourself living in this spectacular home in one of the most highly sought after waterfront communities on the coast of southwest Florida. This is one of the larger homes in the neighborhood. Welcome your family and guests to experience a true Florida lifestyle. The first floor features a well-appointed kitchen, living room, dining room, family room with fireplace, kitchen, laundry room, primary bedroom, 2nd bedroom and two full baths. Two additional bedrooms, a full bath and bonus room occupy the second floor. The amazing Lanai is huge, featuring an inviting heated spa and lap pool, outdoor kitchen, pass thru window and bar top into the main kitchen and plenty of privacy! Southbay Yacht & Racquet Club is a well-established community featuring a private marina with 172 boat slips accommodating everything from jet skis to a 58-foot boat. The beautiful and active clubhouse hosts activities for young and old! Fitness room, heated community pool, library, and gathering areas upstairs and down. The private community park allows you to enjoy beautiful waterfront sunsets. Close to highly rated public schools, waterfront restaurants, shopping, Tiki bar, and a state park! This is a MUST SEE! Professional photos scheduled.

1474 Landview Lane, Osprey

$775,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

This your opportunity to live in Paradise! This home features a large Great Room / Kitchen area which looks out to the Resurfaced Pool and New Lanai Cage. Formal Living and Dining rooms, Three bedrooms, Three Full Baths and a Den! Hurricane Impact Windows. The Kitchen has been nicely updated. Come see all that Southbay Yacht & Racquet Club has to offer. Private Marina can accommodate Boats up to 58', Kayaks, & Jet Skies. Community Pool, Clubhouse, Fitness Room, Tennis and Pickle Ball Courts, Playground, Basketball Court and So much more! Walk or drive your Golf Cart to Restaurants and Shopping. Bedroom Closet Type: Walk-in Closet (Primary Bedroom).

172 Sea Anchor Drive, Osprey

$975,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

A Fantastic Home located in a Fabulous Neighborhood! Custom Designed with a Circular Driveway, Oversize Garage and room for your Golf Cart. Open Floorplan, High Ceilings which are 9'4"-10'8" throughout. Three Large Bedrooms, Three Full Baths plus a Designated Office. This home was custom built by the Seller with well thought out features. Lots of Natural lighting, 8' Sliding Glass Doors provide Beautiful views of the lush landscaping and private pool area. The Great Room offers a wood burning Fireplace, Wet Bar and Entertainment Center. Stereo Speakers throughout the home can be controlled through various Media Inputs. The Kitchen has all the space a cook could want and opens to the Dinette and screened pool deck. Southbay Yacht & Racquet Club is a Boater's Paradise. The Private Marina, Clubhouse, Playground, Fitness Facility, and Outdoor Recreation Choices are Unmatched! Walk, Bike or Drive your Golf Cart to Restaurants, Shopping, Pharmacy, Nail Salon, Hardware Store and Tiki Bars! Come Join the Fun in Southbay!

181 Lookout Point Drive, Osprey

$782,500

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

This is your rare chance to own a custom built home in the "One of a Kind" Marina Community of Southbay! Beautifully maintained three bedroom three bath home. Come enjoy the true Florida lifestyle. The circular driveway and double entry doors welcome you and your guests into this lovely piece of paradise. Features include, Formal Living and Dining rooms, a well appointed kitchen with adjoining family room with fireplace and fantastic view of the pool and privately walled back yard. Enjoy the Community Clubhouse with activities for the entire family. Private Community Marina, Playground, Community Park on The Intracoastal Waterway, Tennis Courts, Pickleball, Bocci Ball and so much more! Walk, Bike or Drive your Golf Cart to shopping, restaurants County Parks and Tiki Bars. This is a must see. You'll be so happy you found Southbay!

216 Windward Drive, Osprey

$905,000

3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Within the much sought after community of Southbay Yacht & Racquet Club, is this wonderfully maintained home featuring classic Florida details often missing in new builds today. Inside the 2,513 sqft home, are 3 bedrooms 3 full bathrooms and a den/office that could be used as a 4th guestroom, ensuring that there is room for everyone. A true split floorplan means privacy for the owner and their guests. Upon stepping through the double door entry, you are greeted by tall ceilings, the formal dining room, and a welcoming view straight out to the lanai space and the grand freshwater pool. Bright vaulted and beamed ceilings in the family room, draw your eye to the working gas fireplace, as well as the breakfast area and kitchen with new stainless-steel appliances. 2 bedrooms, a shared bathroom with pool access, and 2 sets of sliders leading to your outdoor wet bar/kitchen area, round out this wing of the home. Within the opposite wing of the home, you will find the owner's suite with sliding doors to the pool area, an ensuite bathroom boasting soaring ceilings, a spa tub, glass enclosed shower and dual vanities. The den/office is located on this side of the home as is the 3rd guest bathroom. This home has been freshly painted throughout, including the interior of the 2 car attached garage. Storm shutters, tinted windows for energy efficiency and a full home Generac Generator that was installed in 2022 are just a few of the extras in this home. Southbay Yacht & Racquet club is a family oriented community with a 7-acre deep-water basin that can accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet. Amenities include a geothermal heated pool, youth pool, covered outdoor patio, three tennis courts, four pickle ball courts, two shuffleboard courts, youth basketball court, playground, kayak storage and waterfront park. There are 20 acres of common ground with five miles of winding sidewalks in a park-like setting. Make your appointment today. You'll be glad you did!

1426 Landview Lane, Osprey

$820,000

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Under contract-accepting backup offers. "Calling all boaters and water lovers!" Come enjoy Southbay Yacht and Racquet Club and all the amenities the community offers. Nestled on the Inter-coastal waterway with access to the Gulf of Mexico, you can dock your boat in a 7-acre deep-water boat basin that accommodates sailboats and up to 55 foot yachts. Southbay residents also enjoy a clubhouse, heated pool, fitness center, pickle-ball, shuffleboard, fishing, kayak launch and 5 miles of walking trails. This split concept, 4 bedroom, 3.5 bath home with private pool offers a unique floor plan, with a living room, formal dining room and lots of space and privacy indoors and out. Whether you're hosting a family gathering or enjoying a quiet evening with loved ones, this spacious and inviting home offers the ideal setting for making cherished memories. Embrace the Florida lifestyle at its finest with access to the boating lifestyle, fantastic amenities and a vibrant community. Don't let this opportunity slip away – schedule a tour today and make this your own piece of paradise!

53 Landlubber Lane, Osprey

$1,050,000

4 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

This is "The One" Custom built with high end features, this home was built with the future in mind. High Ceilings, open floor plan, massive coral rock fireplace, four bedrooms and three full baths! Located on the end of a quiet cul de sac on an oversize lot with a wide open Greenbelt in the back for privacy. The roof is metal that looks like tile! The circular driveway welcomes you and your guests with open arms. Come make it your own. You will Love being part of this waterfront community with private marina, tennis, pickleball, community pool and active clubhouse. There is truly something for everyone. Drive your golfcart to nearby shopping, restaurants and parks.

1471 Shoal Way, Osprey

$?

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

BANK FORECLOSURE. PRICED TO SELL QUICKLY. GREAT HOME FOR A GROWING FAMILYWITH FOUR BEDROOMS AND THREE BATHS PLUS A COMPLETE GUEST SUITE WITH BATH.LARGE FAMILY ROOM WITH FIREPLACE. HEATED POOL WITH SPA . ZONED A/C.GREATLAUNDRY ROOM WITH CUSTOM BUILT-INS. LOCATED IN DESIREABLE SOUTHBAY WITHDEEP WATER BOAT DOCKAGE AND NO BRIDGES TO THE INTERCOASTAL.CLUBHOUSE AND

239 Sea Anchor Drive, Osprey

Browse All Southbay Yacht & Racquet Club Properties for Sale

Southbay Yacht & Racquet Club Real Estate & Homes