Osprey/Nokomis Homes with Private Pool type

Osprey/Nokomis Homes with Private Pool type

Welcome to the enchanting communities of Osprey and Nokomis, nestled in the heart of Sarasota County, Florida. These charming towns are not just a destination; they are a lifestyle filled with sun-soaked days, breathtaking natural beauty, and a welcoming atmosphere. Osprey, known for its rich history and vibrant arts scene, offers a blend of coastal charm and suburban tranquility, while Nokomis presents a laid-back, beach-town vibe, perfect for those seeking a peaceful retreat.

Living in Osprey and Nokomis means embracing a life of leisure with easy access to stunning Gulf Coast beaches, lush parks, and a plethora of recreational activities. Whether you're strolling along the picturesque shores of Nokomis Beach or exploring the serene waters of the nearby Oscar Scherer State Park, adventure awaits at every corner. The area is also rich in dining and shopping options, ensuring that residents enjoy the best of both worlds.

For those seeking a home that embodies the essence of Florida living, consider the exquisite properties with private pools available in these communities. Imagine spending your afternoons lounging by your own pool, soaking up the sun, or hosting delightful gatherings with friends and family in your backyard oasis. These homes offer the perfect blend of comfort and luxury, allowing you to unwind in style after a day of exploration.

In Osprey and Nokomis, you’re not just buying a home; you’re investing in a lifestyle filled with warmth, community, and endless sunshine. Discover your dream home today and embrace the idyllic Florida life!

Newest Osprey/Nokomis Homes with Private Pool type

854 Macewen Drive, Osprey
$3,670,000
4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Virtually Staged. Virtually Staged. Privacy, golf course views, and exceptional indoor-outdoor living come together in this updated estate on a private cul-de-sac in The Oaks. Light-filled interiors, soaring ceilings, and thoughtfully selected improvements create an inviting atmosphere, with spacious living areas that flow from the chef’s kitchen to the expansive lanai. Outside, enjoy the heated pool and spa, outdoor kitchen, and picturesque golf course views, creating the perfect setting for entertaining or unwinding at home. The first-floor primary suite offers a private retreat with high ceilings, multiple closets, and a versatile sitting area ideal for a home office, fitness space, or quiet escape. Upstairs, a separate guest wing provides added privacy, with a loft, theater room, and screened terrace offering plenty of room to relax and entertain. A split four-car garage, custom finishes, and generous living spaces complete this impressive property. The Oaks is one of Sarasota’s premier country club communities, offering 24-hour security, two championship golf courses, an acclaimed racquets program, fitness and wellness facilities, and fine dining. Beautiful Gulf Coast beaches, shopping, dining, and top-rated schools are all just a short drive away. Explore every detail with the 3D virtual tour and schedule your private showing to experience this exceptional home in person.

854 Macewen Drive, Osprey
102 Windward Drive, Osprey
$1,047,000
3 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Experience refreshed coastal living in Southbay Yacht and Racquet Club. This beautifully updated pool home pairs inviting interiors with outdoor spaces made for relaxing and entertaining. Fresh exterior paint and refreshed landscaping with new sod and palm trees create a welcoming arrival. Inside, new vinyl flooring flows through the living spaces and bedrooms, complemented by large format tile in the bathrooms. High ceilings and a decorative beam add character to the open living area. The redesigned kitchen features new cabinetry, quartz countertops with a waterfall detail, stainless steel appliances, a range hood, pendant lighting, illuminated shelving and a walk in pantry. The home offers three bedrooms, two full bathrooms and one half bathroom. The primary retreat offers two newly built closets and a beautifully remodeled bathroom with a spacious double vanity, freestanding soaking tub, separate shower, new fixtures and mirrors. The remodeled guest bathroom features a large double vanity, coordinating tile and updated shower fixtures. The layout features dual primary bedrooms, with the second offering a generous walk in closet, an attached half bathroom and exterior access. Practical updates complement the refreshed interiors, with hurricane rated windows throughout the home and hurricane shutters for added storm protection. New ceiling fans in the bedrooms, an interior laundry room with a new washer and dryer combo, and an oversized garage with an epoxy painted finish add everyday convenience. Step outside to the screened pool and covered lanai, with a new outdoor shower for rinsing off after a swim. An expanded paver area beyond the lanai with a built in outdoor fireplace offers another inviting space to relax and entertain. Enjoy Southbay Yacht and Racquet Club’s waterfront lifestyle, featuring a community marina with Intracoastal access, a community pool, tennis, pickleball, a fitness center and clubhouse. From time on the water to relaxing evenings by your own pool, this home brings together beautifully updated spaces and an active coastal lifestyle. No CDD.

102 Windward Drive, Osprey
327 Roberts Road, Nokomis
$2,150,000
4 Beds ⋅ 4 Baths ⋅ Roberts Sub SubDv. ⋅ 34275 Zip Code
Striking from the moment you arrive, this 2022-built contemporary residence combines the scale and quality of a custom coastal retreat with a design created for the way Florida is meant to be lived. Set at 327 Roberts Road in Nokomis, the 4-bedroom, 3.5-bath home offers approximately 3,300 square feet under air and nearly 6,000 square feet in total, offering multiple levels of living, expansive balconies, oversized garages, a resort-style backyard, and no HOA. Built by OMKAL Construction and occupied since completion by its builder/owner, the property reflects a thoughtful approach to both design and construction. The three-story layout creates a natural separation between entertaining, everyday living, and private retreat. Elevated above the ground level, the main living floor is bright and open, with abundant natural light, added privacy, and a dramatic two-story great room framed by oversized picture windows and a custom linear fireplace. The kitchen opens seamlessly to the living and dining areas, pairing sleek modern cabinetry with an oversized center island designed for gathering. Expansive balconies extend the living spaces outdoors, capturing coastal breezes, elevated surroundings, and changing evening skies. The primary suite and two additional bedrooms are located on the main level, while the upper floor offers a private fourth suite and spacious loft, ideal as an office, lounge, library, or additional living area. From here, elevated balconies capture views toward the Intracoastal Waterway and offer a quiet vantage point for sunset. The arrangement provides exceptional flexibility for everyday living, extended family, and overnight guests. The finished lower level opens directly to the pool and backyard, creating a relaxed extension of the home's entertaining spaces. With room for a media lounge, fitness area, game room, or casual gathering space, it connects effortlessly to one of the property's most memorable features: its private outdoor retreat. A large heated saltwater pool with spa and tanning ledge anchors the backyard, surrounded by tropical landscaping, custom fencing, accent lighting, tiki torches, porcelain feature walls, and a fire pit. A covered pergola and grilling area provide another inviting place to gather, while generous deck space allows for dining, lounging, and entertaining. Private and beautifully composed, the entire setting functions as a true outdoor living environment rather than simply a backyard. The quality extends well beyond what is immediately visible. Built to newer Florida Building Code standards, the home features hurricane-impact windows and doors, an elevated stem-wall foundation, energy-efficient construction, a flat tile roof, synthetic stucco, large-format porcelain surfaces, and Level 5 smooth drywall, details chosen with Florida's climate, longevity, and ease of ownership in mind. And despite the sense of privacy at home, the best of the Gulf Coast remains remarkably close. Venice, Sarasota, Casey Key beaches, the North Jetty, boating, dining, and recreation are all within easy reach. Modern, substantial, and refreshingly individual, 327 Roberts Road offers something increasingly difficult to find near the coast: newer construction, exceptional indoor and outdoor space, no HOA, and the freedom to enjoy it all on your own terms.

327 Roberts Road, Nokomis
1716 Casey Key Road, Nokomis
$12,650,000
4 Beds ⋅ 4 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code
Spanning nearly an acre from the Gulf of Mexico to Blackburn Bay, this one-of-a-kind Casey Key residence pairs 140 feet of private Gulf frontage with 130 feet of protected bayfront, offering private beach access, boating and sweeping water views from sunrise to sunset. Designed by Jerry Sparkman, AIA, NCARB, of Sweet Sparkman Architecture and completed in 2021, the residence blends architecture and nature, land and water, and linear and curved forms. Its elevated "split-level hugger" design combines a split-level floor plan with a modified courtyard concept, creating intimate gathering spaces and a seamless indoor-outdoor connection. Flowing rooflines, curved walls and broad overhangs form a sculptural silhouette, while warm wood ceilings and walls of glass fill the interiors with natural light and frame the Gulf, Blackburn Bay and tropical landscape in nearly every direction. The light-filled interior is centered around an open great room, dining room and kitchen, where soaring wood ceilings, oversized windows and expansive glass doors open to an elevated waterfront terrace. A separate lounge with a bar offers an inviting space for entertaining, while a waterfront fitness space opens directly to the lawn and bay. Upstairs, the primary suite is wrapped in floor-to-ceiling glass and features a private terrace with uninterrupted Blackburn Bay views. Its spa-inspired bath includes a floating dual vanity, freestanding soaking tub, glass-enclosed shower and corner windows overlooking the water. Three additional bedrooms accommodate family and guests, while the loft provides flexible living space. An elevator connects the home's levels for added convenience. Designed for coastal living, the residence unfolds around a private oasis with a resort-style pool, expansive terraces and shaded lounge areas. Curved stairways and elevated walkways wrap through the architecture, offering changing perspectives of the pool, lawn, bay and Gulf. Covered entertaining spaces provide comfortable places to gather out of the sun, while the open lawn extends toward the bayfront and private dock. From morning on the water to sunset over the Gulf, the property offers a seamless waterfront lifestyle. The residence has also earned NGBS Emerald certification, the highest tier under the National Green Building Standard, along with a RESNET HERS Index rating of -28, a score below zero means the home produces more energy than it consumes, powered in part by on-site solar. It's a rare combination of coastal luxury and true net-positive energy performance. The Gulf-to-Bay setting is essential to the experience. The private dock and boat lift provide direct access to Blackburn Bay, the Intracoastal Waterway and the Gulf. On the west, sunset views are just steps from the beach. A refined palette of stucco, glass, wood and concrete balances architectural sophistication with coastal durability. Native beach grasses, sea grapes and palms soften the transition between the home and its island landscape. Elevated to meet FEMA floodplain requirements and coastal-resiliency standards, the residence responds thoughtfully to its barrier-island setting. Located on Casey Key, it offers exceptional seclusion without sacrificing convenience. The property is positioned between Sarasota and Venice, near historic downtown Venice, Nokomis Beach and waterfront dining, with convenient access to Sarasota International Airport and downtown Sarasota.

1716 Casey Key Road, Nokomis
366 S Creek Court, Osprey
$1,049,000
4 Beds ⋅ 3 Baths ⋅ South Creek SubDv. ⋅ 34229 Zip Code
Welcome to 366 South Creek Court, located in the highly sought-after gated waterfront community of South Creek in Osprey, Florida. Nearly completely renovated, this beautiful 4-bedroom, 3-bathroom home offers 2,775 square feet of thoughtfully designed living space, combining elegant finishes, comfortable living spaces, and exceptional indoor-outdoor living. The open and bright floor plan features separate living and dining areas, a spacious family room, and a charming dinette overlooking the lanai and backyard. Luxury details throughout include tray ceilings, crown molding, rounded wall edges, plantation shutters, 8-foot doors, arched doorways, and engineered hardwood flooring. Fresh interior paint and expansive windows and doors fill the home with natural light. At the heart of the home is the beautifully renovated kitchen, featuring 42-inch shaker-style soft-close cabinetry with crown molding, deep drawers, stainless steel appliances, induction cooking, a hood vent, dual-bowl sink, and quality hardware. Vibrant quartz countertops and an oversized island with seating create an inviting space for everyday living and entertaining. The front living area provides a welcoming setting for conversation or relaxing with a book beside the electric fireplace with solid wood mantel. Adjacent to the living space is a dedicated dining area with a wet bar and wine chiller, ideal for entertaining family and guests. The spacious primary suite offers abundant natural light and direct access to the screened lanai. The ensuite features dual vanities, a dedicated makeup counter and seat, generous counter space, dual walk-in closets, and a brand-new oversized custom walk-in shower. Three additional guest bedrooms offer excellent closet space and natural light. The first guest bath combines a large walk-in shower with a conveniently located laundry area featuring a stackable washer and dryer. The second guest bath offers a dual vanity, tub/shower combination, and adjacent linen closet. Outdoor living takes center stage with a covered and screened paver lanai featuring a heated pool and spa. The lush, mature landscaping and areca palm-lined backyard provide a private and tranquil setting. An additional exterior patio has been designed to accommodate a 72-inch outdoor kitchen, creating an ideal space for entertaining. The home welcomes guests with a paver driveway and sidewalk leading to a charming country-style front porch. The oversized two-car extended garage features ceiling storage racks, a side-entry door, and a hurricane-rated garage door. Additional exterior improvements include fresh paint, new lighting, security cameras, beautiful landscaping, an irrigation system, and hurricane storm panels for every opening. South Creek offers a low HOA fee and an exceptional collection of amenities, including a kayak launch, tennis and pickleball courts, basketball court, and community boat and fishing dock on the South Creek saltwater canal. Ideally located near Casey Key, Nokomis and Siesta Key beaches, Pine View School, shopping, restaurants, a dog park, and the Legacy Trail. Located in an X flood zone, flood insurance is optional. This beautifully renovated South Creek home offers the perfect combination of style, privacy, amenities, and coastal Florida living.

366 S Creek Court, Osprey
2166 Sonoma Drive E, Nokomis
$685,000
3 Beds ⋅ 4 Baths ⋅ Mission Estates SubDv. ⋅ 34275 Zip Code
Prime location! Nestled between charming Venice and the cultural hub of Sarasota, the highly sought-after community of Mission Estates serves as an exclusive haven for those seeking a harmonious blend of elegance and nature. This spectacular three-bedroom, three-and-a-half-bathroom pool home is framed by gorgeous mature landscaping, cand boasts a truly premium lot, backing up directly to the pristine fairways of the Mission Valley Golf Course! Step inside to discover a beautifully appointed, enthusiastic interior centered around a modern kitchen complete with a large island, perfect for culinary adventures and entertaining guests. The expansive living space is enhanced by a striking fireplace and ceiling fans throughout, ensuring absolute comfort year-round. Relax in the luxurious owner's suite, which offers cozy carpeting and a convenient private entrance leading directly to the outdoor oasis. Family and visitors will feel right at home, as every single bedroom features plush carpeting and its very own private ensuite bathroom, providing unparalleled comfort and privacy that is perfectly complemented by an additional half-bath in the main living area. Embrace the ultimate Florida lifestyle on the spacious screened lanai, where you can lounge by your private sparkling pool while enjoying the serene, private surroundings. Situated in a truly fantastic location, this home provides effortless access to pristine Gulf beaches, the lush fairways of Mission Valley Country Club and Calusa Lakes Country Club, and the scenic biking and walking paths of the Legacy Trail. Experience the exceptional lifestyle you deserve in this breathtaking Mission Estates home!

2166 Sonoma Drive E, Nokomis
2009 Tocobaga Lane, Nokomis
$630,000
3 Beds ⋅ 3 Baths ⋅ Calusa Lakes SubDv. ⋅ 34275 Zip Code
Welcome to Calusa Lakes, a sought-after gated golf course community in Nokomis, just 4.2 miles from the beach and a short drive to historic Downtown Venice. Meticulously maintained by the same owner since 1997, this spacious 3 bedroom, 2.5 bath pool home with 2,466 square feet of living area offers generous room sizes, a thoughtful split floor plan and a beautiful golf course setting. The Montego model by Lincoln Homes features formal living and dining rooms accented by crown molding, along with pocket sliding doors that open the living area to the lanai, perfect for enjoying Florida’s beautiful weather. The comfortable family room is located just off the kitchen and also opens to the pool area through sliding glass doors. An inviting breakfast nook features an aquarium window overlooking the pool and lush outdoor setting. The kitchen has been tastefully refreshed with creamy raised-panel wood cabinet fronts accented with a warm glaze and complemented by GE Profile appliances. The spacious primary suite offers direct access to the pool, room for a sitting or reading area, dual closets including a walk-in, and an ensuite bath with an updated vanity, garden tub and separate walk-in shower. A generously sized office features an attractive washed-oak built-in system with abundant space for books, files and a comfortable work-from-home setup. Two additional bedrooms and a shared bath are privately positioned away from the main living areas, enhancing the home’s desirable split-plan design. Step outside to the screened pool and spa surrounded by a pavered patio and charming garden areas. A convenient private pool bath is accessed directly from the pool deck, keeping wet feet out of the main living areas and making entertaining especially easy. Mature landscaping currently provides a wonderful privacy buffer from the golf course, while offering the opportunity to selectively open the landscaping for a more expansive golf course view. Additional highlights include a roof replaced in 2017 and A/C replaced in 2019. Lovingly cared for and exceptionally well maintained, this Calusa Lakes home offers space, privacy, a pool and spa, golf course surroundings and an outstanding Nokomis location convenient to Gulf beaches, shopping, dining and Downtown Venice.

2009 Tocobaga Lane, Nokomis
Nokomis
$705,000
2 Beds ⋅ 2 Baths ⋅ Waterfront Estates SubDv. ⋅ 34275 Zip Code
Welcome to your own slice of Florida paradise! This beautifully renovated canal-front home in Nokomis has been thoughtfully updated from top to bottom and is truly turn-key move-in ready and has the option of being fully furnished. Enjoy peace of mind with a durable metal roof, along with a completely renovated kitchen featuring a gas range and new appliances. The beautifully updated bathrooms showcase oversized walk-in showers and modern finishes throughout. Designed for the Florida lifestyle, the home features a heated pool, three screened-in lanais, a spacious Florida room, and a private fishing dock right on the canal. With multiple indoor and outdoor living spaces, there’s plenty of room to relax, entertain, and enjoy life on the water year-round. Best of all—NO HOA! A rare opportunity to enjoy a fully renovated waterfront home with a pool, private dock, and incredible outdoor living in beautiful Nokomis

Nokomis
2116 Casey Key Road, Nokomis
$6,850,000
4 Beds ⋅ 4 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code
Virtually Staged. Imagine the possibilities of Gulf-to-Bay living on Casey Key, where deeded private beach access, deep-water boating and a resort-style bayfront setting create the foundation for an extraordinary coastal retreat. Set on more than half an acre with frontage on Blackburn Bay, 2116 Casey Key Road offers more than 5,500 square feet and an exceptional opportunity to enjoy a substantial island residence around one of Sarasota County’s most coveted waterfront lifestyles. The exterior has been thoughtfully enhanced for enjoying life on the water. Along the bayfront, a multi-level tropical setting unfolds through expansive pavered terraces, covered lounge areas and a gazebo-style dining pavilion with a fully equipped summer kitchen and built-in grilling station. At the center is a heated swimming pool and spa finished in PebbleTec, creating a private resort environment framed by mature tropical surroundings and the waters of Blackburn Bay. A screened second-level bayfront terrace provides another inviting place to relax. For boaters, the property is equally compelling. The extended dock, updated in 2018, includes a lift and provides deep-water access, accommodating both powerboats and sailboats. Deeded private beach access places the Gulf’s turquoise waters and spectacular sunsets just steps from home—creating the increasingly rare opportunity to enjoy both boating and the beach from a single property. Inside is where the next chapter begins. Soaring cathedral ceilings, generous room proportions and walls of oversized impact windows and sliders establish an impressive framework, filling the residence with natural light while capturing sweeping views across Blackburn Bay. The home’s substantial footprint and flexible two-level configuration offer tremendous potential for a thoughtful renovation tailored to today’s coastal lifestyle. Select virtually staged images illustrate just one vision for how the existing spaces could be transformed with a more contemporary aesthetic. The first level provides exceptional flexibility for family and guests, with a family room, game room, two guest bedroom suites, an office with built-ins that can also function as a fourth bedroom, and a convenient kitchenette. This arrangement lends itself beautifully to extended family, visiting guests or the creation of private living quarters within the home. Upstairs, the main living spaces take full advantage of the elevated bayfront setting. The living and dining rooms are joined by a kitchen with granite countertops, center island, informal dining area and stainless steel appliances, along with a wet bar and wine cooler. The primary suite is also located on this level, allowing the principal living spaces to share the home’s expansive water views. A three-stop elevator and interior staircase connect the levels. Considerable improvements include a 2022 metal roof, multiple A/C replacements from 2017–2024, replacement of non-impact windows with Andersen impact windows, updated dock and lift pilings, new ductwork, electrical upgrades and re-piping. Located on the quieter southern end of Casey Key, the property feels wonderfully removed while remaining convenient to Nokomis, Venice and Sarasota. Nearby destinations include Nokomis Beach, the restaurants and boutiques of Venice Island, area marinas and the Legacy Trail, while Downtown Sarasota’s dining, performing arts, cultural attractions and waterfront are within comfortable reach.

2116 Casey Key Road, Nokomis
422 Blue Garden Lane, Osprey
$1,445,000
3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Discover incredible value and endless potential in this beautifully maintained 3 bedroom, 3.5 bath home, tucked into lush tropical landscaping, on a quiet cul-de-sac in The Oaks Bayside. A grand traditional residence, with generous sized rooms, flexible living areas, and a private outdoor setting, the possibilities here are limitless. Step into the marble entry through the double front doors, and you will love what you find inside. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook overlooking the pool. The elegant primary suite offers marble floors, soaring ceilings, plantation shutters, and private access to the pool for an early swim or late-night dip. A glamorous dressing area leads to the spa-like bath with soaking tub, walk-in shower, and marble finishes. Two additional oversized en suite bedrooms provide comfort and privacy for guests. A large laundry room with ample cabinetry and an adjacent private sauna completes the interior. Outdoors, the free-form pool with rock outcroppings and waterfall is a showstopper, surrounded by both shaded and open areas for dining and relaxing. With two adjoining lots preserved as gardens, this home offers rare seclusion in a natural setting. The Oaks Club features two 18-hole championship golf courses, an award-winning tennis program, pickleball courts, a state-of-the-art fitness center and a junior Olympic, community pool as well as a celebrated social calendar, and incredible dining options. There is currently no waiting list for either Golf or Sports/Social membership.

422 Blue Garden Lane, Osprey
3718 Sandspur Lane, Nokomis
$5,750,000
4 Beds ⋅ 8 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code
At the water’s edge of Sandspur Lane sits one of Casey Key’s best-kept secrets: a stunning estate offering unmatched privacy, tranquility, protected waterfront, and bespoke contemporary coastal architecture. A multi-year renovation completed in 2024 reimagined the property, adding more than 2,000 square feet of interior and exterior living space and transforming an already exceptional waterfront home into a truly distinctive residence. Tucked at the end of this quiet, private lane, the home’s structural features and sheltered location provide proven storm-resilient advantages. Ownership of both sides of the canal protects the mature trees and vegetation along the opposite shoreline, preserving natural privacy. The main level features vaulted ceilings and an open floor plan connecting the modern kitchen with dining, living, and family rooms, while wraparound aquarium glass windows and sliding glass doors flood the space with natural light and offer views of the water and the parcel’s expansive waterfront setting. A floating staircase rises through a circular glass stair tower to the primary suite, featuring a spacious bath, sitting room, and a private balcony with long water views. An adjoining casita with its own private entrance and water views provides luxurious accommodations for family, guests, or in-home staff. Two dedicated offices with built-in cabinetry and granite desks offer long ICW views, creating an inspiring setting for work or personal pursuits. A new elevator connects every level, from the garage to the rooftop deck. Designed for recreation and entertaining, the property features a cabana with bar and outdoor kitchen, a new waterfall spa and remodeled pool with water features, a home gym, firepit, indoor-outdoor Sonos sound system, and multiple balconies, terraces, and decks. After sunset the extensive outdoor lighting, including dock and underwater fish lights, transforms the property. The long driveway and motor court accommodate parking for 12–15 vehicles— a rarity on Casey Key. The 200 feet of protected waterfront includes a newly added 45-foot dock, 20,000-lb. boat lift, and two PWC lifts. And when the Gulf beckons, deeded beach access leads to its warm waters and shoreline. From sunrises over the ICW to Gulf sunsets from the rooftop deck and illuminated evenings poolside, the home embraces its waterfront setting from virtually every angle. This residence offers a package increasingly hard to find: extraordinary privacy, tranquility, and protected waterfront living—all wrapped in a beautifully reimagined contemporary coastal estate on one of Florida’s most exclusive islands.

3718 Sandspur Lane, Nokomis
275 Lookout Point Drive, Osprey
$4,590,000
5 Beds ⋅ 5 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code
Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.

275 Lookout Point Drive, Osprey
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