Osprey Single Family Homes For Sale - 69 homes

Remarks: Classic and cool, this Sorrento Shores beauty blends true Old Florida charm with all the modern updates you actually want, perfectly positioned West of the Trail near the sparkling Intracoastal Waterway. What’s been at the top of your list — move-in ready, a spacious lot, no flood zone, boat/RV parking, optional low HOA, no CDD fees, community marina access, an A+ school district, or quick access to beaches and dining? The good news? You don’t have to choose. This home truly checks every box. Inside and out, everything has been thoughtfully renovated since 2022, including a new roof (2023 w 25yr warranty), septic, central air, impact windows and doors (with the exception of the Florida room), updated electrical panel, irrigation equipment, soffits, water heater, impact garage door, pavers, and beautifully redesigned kitchen and baths. Luxury vinyl plank flooring runs throughout, complemented by fresh paint and abundant natural light. The split floor plan provides privacy, while the open living spaces make everyday living and entertaining effortless. The kitchen is both functional and inviting, featuring shaker cabinetry, quartzite countertops, stainless steel appliances, a generous island, and a charming coffee bar that flows seamlessly into the family room and dinette. One of the standout features is the 336-square-foot air-conditioned sunroom with pocket sliders — incredible flex space for a home office, gym, playroom, or second living area — all overlooking the expansive backyard. The screened lanai and paver patio create easy indoor-outdoor living year-round. The only real decision left? Whether you’ll sip coffee on the welcoming front porch as neighbors pass by or unwind in your private backyard oasis listening to the whispering waves. Sorrento Shores is just minutes from Nokomis Beach (4 miles) and Venice Beach (6.5 miles), close to Oscar Scherer State Park and the Legacy Trail (1.5 miles), near the renowned Pine View School (2.9 miles), with convenient access to I-75, historic City of Venice (5.5 miles) and vibrant downtown Sarasota (12 miles). Here, functional updates, classic charm, location and lifestyle all come together — schedule your showing today!

Listing is courtesy of: COLDWELL BANKER SARASOTA CENT. (941-487-5600)

Listing Agent: Lauren Sisco (904-652-9387)

Remarks: Multigenerational living behind the gates of The Oaks Golf & Country Club. Set on a rare double lot at the end of a quiet cul-de-sac, this exceptional home is perfectly positioned on the 1st hole of the Heron Course, capturing sweeping golf course and clubhouse views—just minutes from Siesta Beach and Casey Key. The main residence offers 4,700+ square feet, complemented by a private 1,500+ square foot guest house—ideal for extended family or long-term guests. Outdoor living is elevated with a pool and spa, outdoor kitchen, private guest laundry, and some of the most captivating views in the community. At The Oaks, coastal sophistication unfolds across 36 championship fairways, tennis and pickleball courts, with endless opportunities for recreation, dining, and connection. Membership required.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)

Listing Agent: Karin Watt (941-773-1273)

Remarks: **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home showcases timeless architecture with a thoughtful layout and extensive 2023–2025 updates throughout. From its striking curb appeal to its serene outdoor living spaces, every detail has been meticulously curated. Inside, the home offers 4 EN SUITE BEDROOMS, 5.5 BATHS, and a 3-CAR GARAGE that’s been freshly painted and upgraded with a new epoxy floor. Walls of glass fill the home with natural light, complemented by plantation shutters and new motorized window shades throughout. Major updates include a new tile roof (August 2025), two new HVAC units, new LED lighting, and new outlets and light switches across the home. The entire interior and exterior were freshly painted in 2023, giving the home a bright and modern aesthetic. The primary suite is a private retreat, featuring new flooring, a spacious bath, and a bonus office/dressing area for added versatility. A separate office or sitting room, also with new floors, provides ideal space for remote work or quiet relaxation. The three additional bedrooms feature new carpeting, creating a cohesive and comfortable atmosphere. The chef’s kitchen is equipped with new stainless-steel appliances (refrigerator, dishwasher, – all 2025) and flows seamlessly to the main living areas and outdoor entertainment space. There is a new 2025 washer and dryer as well. Step outside to your private Florida oasis — a covered lanai with a full outdoor kitchen and a large motorized Sunbrella shade for comfort and convenience. The property’s two fountains (one new) and professionally graded, elevated landscaping create a lush and tranquil environment perfect for al fresco dining or quiet reflection. The Oaks is a distinguished, 24hr guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)

Listing Agent: Mark Lyda (941-586-2670)

Remarks: This beautifully updated, 1,284-square-foot, mid-century home sits on over one-third of an acre and has been thoughtfully renovated with distinctive Sarasota modern flair by HGTV Design team. Go through the vibrant turquoise door into a light-filled interior featuring gleaming terrazzo floors and clean mid-century lines. Sliding walls of glass create seamless indoor-outdoor living, opening from the living room, dining room, kitchen and primary bedroom to a spacious screened porch that overlooks a scenic pond and expansive yard. Whether entertaining guests or enjoying a quiet morning coffee, the outdoor living space extends your home beautifully. The kitchen is stylish and functional, offering gently used stainless KitchenAid Gallery appliances, space-saving self-closing cabinetry, and a generous open breakfast bar ideal for casual dining and gathering. Baths have been tastefully modernized with updated cabinets, countertops, fixtures and lighting. Major improvements provide peace of mind, including 2025 sewer pipes relined, a 2022 air-conditioning system, 2015 re-roof, 2015 hurricane-impact windows, 2015 gutters plus interior and exterior paint, and refreshed landscaping. Additional highlights include a two-car attached garage, dedicated workshop space and access to boat docks (Contact HOA for details). Ideally West of the Trail between Sarasota and Venice, with convenient access to Highway 681 and Interstate 75, this home places you close to everything. Top-rated schools nearby include Pine View School for gifted and Venice High School, known for strong sports and arts programs. Outdoor enthusiasts will love being just 5 to 10 minutes from Nokomis Beach, Blackburn Point Park kayak and boat launch, Oscar Scherer State Park, offering hiking, camping, cycling, kayaking, boating and fishing, and the Legacy Trail, which is ideal for biking with family or friends. Dining options abound, including waterfront favorites nearby. This is Florida living at its finest, with modern design, natural beauty, boating access and an unbeatable location.

Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-412-3323)

Listing Agent: Crystal Cosby, Llc (941-882-0070)

Remarks: **STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, etc. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)

Listing Agent: Mark Lyda (941-586-2670)

Remarks: Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)

Listing Agent: Natalie Gutwein (941-993-2660)

Remarks: On the quiet and coveted stretch of North Casey Key, where century-old oaks meet the shoreline, and the land unfolds uninterrupted from Gulf to bay, this extraordinary 1.5-acre estate offers a rare opportunity to steward one of the island’s most incredible homesites. With 180 feet of private Gulf frontage and exceptional depth across to the intercoastal, the property is defined by its scale, privacy, and quiet permanence—offering a setting that feels both expansive and deeply secluded beneath a canopy of mature coastal forest. Here, the rhythm of the water and the natural beauty of the land create an environment that cannot be replicated. The existing improvements include a Gulf-facing main residence, originally constructed in the early 1970s, thoughtfully positioned to capture sweeping views in both directions. The two-bedroom, two-bath home features elevated ceilings, expansive windows, and a sunlit central courtyard designed to bring light and the surrounding landscape into everyday living. A separate guest house, completed in 2002, provides two additional bedrooms and baths, bamboo flooring, Bahama shutters, a versatile bonus room, and an oversized two-car garage—offering flexible accommodations for guests, or interim use while renovating or building. A recently installed private dock completes the property’s rare Gulf-to-Bay lifestyle and provides immediate access to boating and waterfront recreation. While the existing structures offer renovation potential and immediate livability, the true and enduring value lies in the land itself. Homesites of this magnitude—spanning Gulf to bay with this level of frontage, privacy, and natural beauty—are rarely available. Conceptual plans by Potter Homes envision a timeless coastal estate exceeding 6,500 square feet under air, thoughtfully designed to preserve the character of the land while capturing panoramic water views and creating a residence of lasting architectural significance. Whether preserved, renovated, or reimagined entirely, this is more than a homesite—it is the foundation for one of Casey Key’s next great estates, and an opportunity to create something that will endure for generations.

Listing is courtesy of: POTTER TRINITY (239-254-9319)

Listing Agent: Charlie Ruck, Pa (239-464-0191)

Remarks: Under contract-accepting backup offers. Located in the prestigious gated community of The Oaks Golf & Country Club in Osprey (Sarasota area), this elegant single-story residence at 530 N Mac Ewen Drive offers resort-style living with championship golf just steps away. Spanning 4,346 square feet under air and 5,837 square feet under roof on an oversized lot, the home features 4 bedrooms, 5 full bathrooms, 1 half bathroom, and a 3-car garage with built-in cabinets and the bonus of a car lift allowing for 4 cars in total. Presented fully furnished and turnkey, this meticulously maintained home is move-in ready and showcases exceptional craftsmanship throughout. Italian granite flows through the interiors, complemented by designer lighting and a whole-house water softener/filtration system. The custom handcrafted kitchen is a chef’s dream, complete with a hidden pantry, soft-close drawers and doors, spice drawers, double oven, and premium Viking Pro appliances. A custom built-in wet bar with ice machine and pull-outs adds convenience for entertaining, while a panoramic electric fireplace anchors the living spaces. A built-in sound system throughout the home and custom closets in every bedroom (including a Therma Sol steam shower in the primary suite) enhance daily comfort. Additional practical luxuries include a bolted-in safe. Step outside to an expansive lanai and backyard oasis featuring a custom-designed pool and hot tub with fire feature, plus a fully equipped outdoor kitchen—perfect for al fresco dining and year-round enjoyment. Industrial-grade landscape lighting (valued at $40K) beautifully illuminates the mature, oversized lot. Residents of The Oaks enjoy 24/7 gated security and world-class amenities including two 18-hole championship golf courses, tennis courts, pickleball, a state-of-the-art fitness center, and vibrant social events. This turnkey luxury home in one of Sarasota County’s most sought-after private communities is an exceptional opportunity for discerning buyers seeking refined coastal Florida living. Roof is 2017 (Tile) and A/C is newer (2023)

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Niall Phelan (941-914-8589)

Remarks: Under contract-accepting backup offers. **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPACIOUS 4-BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in-law or multi-generational suite. Featuring 3 full baths and a coveted 3-car garage, this reconfigured floor plan provides flexibility, privacy, and comfort for today’s lifestyle. Situated on an ideal corner lot, the home enjoys peaceful water views from the rear and a lovely park view from the front. Major updates include a brand-new kitchen with granite countertops and stainless-steel appliances, fresh interior and exterior paint, and new flooring throughout, including luxury vinyl plank, etc. Plantation shutters add timeless charm and style. Newer ROOF (2021). Located in the highly sought-after community of Rivendell, known for its tree-lined streets, serene lakes, and natural preserves spanning 380 acres adjacent to Oscar Scherer State Park. This home is just minutes from nationally ranked Pine View School, Sarasota’s nationally ranked gifted school, as well as The Legacy Trail for miles of biking, walking, and skating. Enjoy the best of Florida living just 6 miles from Nokomis Beach and approximately 20 minutes to Siesta Key Beach. Rivendell is a deed-restricted community offering residents a community pool, playground, park, and gazebo. This exceptional home combines location, lifestyle, and luxury—schedule your private showing today!

Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)

Listing Agent: Mark Lyda (941-586-2670)