Osprey Homes with Pool

Osprey Homes with Pool

Welcome to Osprey, Florida—a hidden gem nestled along the stunning Gulf Coast in Sarasota County. This charming community seamlessly blends the tranquility of a small town with the vibrancy of coastal living. With its picturesque landscapes, lush greenery, and proximity to the sparkling waters of the Gulf of Mexico, Osprey offers an idyllic setting for those seeking a serene lifestyle.

Osprey is known for its rich history and natural beauty, featuring attractions such as the historic Spanish Point, where you can explore the area's Native American heritage and beautiful gardens. The nearby Nokomis Beach is just a stone's throw away, inviting residents to bask in the sun, swim, and enjoy breathtaking sunsets. Outdoor enthusiasts will appreciate the numerous parks and nature trails, perfect for hiking, biking, and birdwatching.

One of the highlights of living in Osprey is the abundance of homes with pools. Imagine stepping out into your private oasis on a warm Florida day, where you can relax by the poolside or host unforgettable gatherings with family and friends. These homes often feature spacious backyards, making them ideal for both relaxation and entertainment. Whether you’re looking for a cozy retreat or a luxurious estate, Osprey’s real estate market offers a diverse selection of properties to suit your lifestyle.

In Osprey, you’re not just buying a home; you’re investing in a lifestyle defined by comfort, community, and coastal charm. Discover the beauty of Osprey and find your dream home with a pool today!

Newest Osprey Homes with Pool

$3,700,000
4 Beds ⋅ 4 Baths ⋅ A4707301 MLS
This custom-built 2024 masterpiece was thoughtfully designed to deliver the perfect balance of luxury, functionality, and effortless indoor-outdoor living. Positioned to capture sweeping views of the 6th and 7th holes of the Heron Course, the home showcases exceptional craftsmanship and attention to detail at every turn. From the moment you arrive, the impressive 10 foot hurricane-rated steel front door, circular driveway, and beautiful exterior create a lasting first impression. Inside, wood-look tile flooring flows throughout. The expansive open concept layout seamlessly connects the main living spaces while still offering dedicated rooms for privacy and everyday comfort. The designer kitchen is a true showpiece, featuring a custom range hood, pot filler, oversized refrigerator, and premium finishes that cater to both casual family meals and formal entertaining. The large master suite is a study in elegance. The luxurious master bath is the pinnacle of luxury, with dual sinks, a lighted stand alone make up table, claw foot tub, huge steam shower, expansive countertop and storage space along with custom lighting. The upstairs loft is a great addition for those who love to entertain and host guests. It has a bedroom, bathroom, and living area with a bar and a balcony providing lovely views over the pool. Step outside to a truly exceptional outdoor retreat where luxury and tranquility come together in a breathtaking setting. The resort-style pool and spa serve as the centerpiece of the home's outdoor living experience. Designed for both relaxation and entertaining, this private oasis features expansive lounging areas, an incredible outdoor kitchen, and seamless indoor-outdoor connectivity through hurricane-rated bifold sliders that open the home to the stunning golf course backdrop. Built not only for beauty, but also for convenience and peace of mind, the home is equipped with premium hurricane-rated windows and bifold sliders, spray foam insulation, central vacuum, automated lighting and climate control systems, and wiring for a generator. Everyday functionality is enhanced by a dedicated mudroom, spacious laundry room, climate-controlled storage, and a four-car garage complete with epoxy floors, custom storage solutions, and additional space for a gym or workout area. shaded dining, and a sun-splashed pool and spa area under a screened enclosure. With mandatory membership, this home offers access to all of the amenities being a member of The Oaks has to offer. There is currently no waiting list for either Golf or Sports/Social membership.

650 Oaks Creek Court, Osprey/Nokomis
$449,000
3 Beds ⋅ 2 Baths ⋅ A4706429 MLS ⋅ Heron Harbor BLDG.
Welcome to luxury coastal living in this exceptional 3rd-floor penthouse condo nestled in the secluded, resort-style waterfront community of Heron House in Osprey. Offering 1,883 sq. ft. of beautifully light-filled, fully furnished living space, this impressive 3-bedroom, 2-bathroom residence features high-end finishes, warm hardwood floors, plantation shutters, a decorative wood-burning fireplace, and a built-in wet bar perfect for entertaining. The gourmet kitchen is equipped with rich wood cabinetry, granite countertops, stainless steel appliances, and a cozy eat-in breakfast area. Unwind in the expansive primary suite boasting two walk-in closets, a spa-like bath with double vanities, a deep soaking tub, and a separate shower. Step outside onto multiple private balconies to take in tranquil views of lush tropical greenery and calm canal waters—an idyllic setting for outdoor dining or evening cocktails. Located directly on Jessie Harbor with bridge-free, direct access to the Intracoastal Waterway and the Gulf, this gated community offers extraordinary waterfront amenities, including a kayak launch, boat slips (available on a first-come, first-served basis), and frequent visits from local wildlife like otters and dolphins. Residents enjoy a highly active, beautifully maintained HOA complete with a newly installed entrance security gate, heated pool, water aerobics, tennis and pickleball courts, shuffleboard, clubhouse, fitness center, walking trails, locked storage, bike storage, and two assigned covered parking spaces under the building with elevator access. Situated just 10 minutes from Venice Beach, Nokomis Beach, and Casey Key, 20 minutes from world-famous Siesta Key, and minutes from I-75, Oscar Scherer State Park, the Legacy Trail, and Sarasota’s vibrant cultural hub, this hidden gem combines peaceful privacy with unbeatable access to Florida’s finest coastal living.

7303 Jessie Harbor Drive Unit 7303, Osprey/Nokomis
$695,000
3 Beds ⋅ 3 Baths ⋅ A4707057 MLS ⋅ Meridian I BLDG.
This exceptional 4th floor end unit is ideally positioned on the coveted south corner of Meridian I, offering a particularly desirable location with no neighboring buildings interrupting the expansive Preserve and water views. Floor-to-ceiling windows showcase the beautiful natural setting and fill the residence with abundant natural light. Featuring 3 bedrooms, 3 baths, plus a formal dining room that can easily serve as a den or home office, the spacious floor plan is equally well suited for everyday living and entertaining. Step directly from your private elevator into a warm and inviting interior, where beautiful cherry wood floors extend throughout most of the residence, adding richness and warmth while complementing the abundant natural light and picturesque views. The generously sized kitchen features white cabinetry and appliances, a breakfast nook and pantry, creating a bright, clean look with plenty of workspace and storage. Both the primary suite and great room open to the large, screened balcony, extending the living space outdoors and providing a wonderful setting to enjoy the peaceful Preserve and water views by day and spectacular sunsets in the evening. Meticulously maintained, the residence includes Hunter Douglas window coverings, a custom entertainment center with electric fireplace, remote-controlled storm shutters along the balcony enclosure, two assigned parking spaces in the covered garage and a private storage unit. Residents of Meridian enjoy a community pool, spa and fitness center, along with all the exceptional amenities of The Oaks Club, including two championship 18-hole golf courses, 12 Har-Tru tennis courts (4 lighted), 4 pickleball courts, the WellFit Center, three onsite restaurants, and an extensive calendar of social and recreational activities. Membership in The Oaks Club is required. There is currently no waiting list for either Golf or Sports/Social membership.

385 N Point Road Unit 401, Osprey/Nokomis
$629,400
3 Beds ⋅ 3 Baths ⋅ A4707579 MLS ⋅ Meridian Vi BLDG.
Virtually Staged. EXCEPTIONALLY SPACIOUS CORNER CONDO – NEARLY 3,200 SF – NO WAITLIST FOR GOLF MEMBERSHIP! Ideally situated behind the gates of the highly sought-after Oaks Preserve, this elegant and beautifully appointed corner residence offers an impressive combination of space, privacy, and resort-style living. The nearly 3,200 SF open floorplan features 3 en-suite bedrooms and 3 baths, providing exceptional comfort and flexibility. Light and bright throughout, the residence showcases crown molding, engineered hardwood flooring, and an expansive kitchen with granite countertops and stainless-steel appliances. Enjoy the serene, private preserve setting from multiple screened balconies, enhanced by convenient remote-controlled automatic hurricane shutters. Additional features include 2 assigned parking spaces, including 1 under-building space, plus climate-controlled storage. A rare opportunity to enjoy substantial living space, privacy, and the exceptional lifestyle of The Oaks! This NEWEST Tower (built in 2007) in the Meridian Condo Complex features Hurricane Impact Windows and Doors and is conveniently located next door to the condo residents’ private Amenity Center featuring Heated Pool & Spa, Fitness Room and outdoor grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS 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. 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. **A MUST SEE**

3603 N Point Road Unit 202, Osprey/Nokomis
$679,000
2 Beds ⋅ 3 Baths ⋅ A4707242 MLS ⋅ Na BLDG.
**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living area entails an inviting great room that opens to serene water views framed by palms and natural greenery while the European-style kitchen is thoughtfully designed with premium SubZero, Wolf and Bosch appliances, modern wood cabinetry, polished granite countertops, and durable ceramic tile flooring—ideal for both everyday living and entertaining. Architectural details add warmth and character throughout, including hand-plastered walls with art niches, graceful archways, plantation shutters, and sisal carpeting. Just off the entry foyer, you’ll find a convenient powder room and a separate laundry room. A private brick balcony provides ample space for outdoor dining or relaxing while enjoying the peaceful surroundings. The primary suite overlooks the lake and includes two walk-in closets and a spacious bathroom featuring dual vanities, walk-in shower, jacuzzi tub and appointed with upscale finishes. The guest suite is equally comfortable, complete with built-in shelving and ample storage. 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 lighted), 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.

33 Bishops Court Road Unit 118, Osprey/Nokomis
$1,399,000
3 Beds ⋅ 3 Baths ⋅ A4707187 MLS
This beautifully appointed residence sits on a private, well-maintained lot surrounded by grand, colossal oaks and palm trees, delivering the privacy and curb appeal today's buyers are searching for. Step through the front door and feel the difference - soaring tray ceilings, rich crown molding, and tons of natural sunlight set an elegant tone throughout. The gourmet kitchen is the true showstopper, with gleaming stone countertops, solid wood cabinetry, and an open flow into the living and dining areas — perfect for entertaining or unwinding after a day at the club. Retreat to the luxurious owner's suite complete with dual walk-in closets and a private sitting area, while two additional bedrooms offer guests or family their own well-appointed space. Move-in ready and meticulously maintained, this home features updated salt pool equipment, a refreshed kitchen area, and an updated 3-car garage with maintenance-free epoxy flooring. The compulsory membership in The Oaks Club unlocks an unbeatable lineup of amenities. Schedule a viewing today!

256 Sugar Mill, Osprey/Nokomis
$165,000
2 Beds ⋅ 2 Baths ⋅ A4706691 MLS
Welcome home to this charming fully furnished 2-bedroom, 2-bath mobile home, built in 2001 and located in the friendly and active Arbors Mobile Home Park in beautiful Osprey, Florida. Featuring an inviting open floor plan, this home offers comfortable living spaces filled with natural light from an abundance of windows. Luxury vinyl plank flooring flows throughout the living areas, creating a clean and cohesive look. The kitchen opens seamlessly to the living and dining areas, making entertaining and everyday living easy. The dining room features a built-in buffet with both lower and upper-glass-front cabinets, providing attractive display space and convenient storage. The primary suite includes a single vanity and walk-in shower, while cathedral ceilings add to the home's open and airy feel. An interior laundry area adds everyday convenience. Outside, a charming shed provides additional storage, and the newer carport, added in 2025, offers covered parking. The AC was replaced in 2024 for added peace of mind. Enjoy the Florida lifestyle in The Arbors, a welcoming 55+ community with a variety of amenities and an active social calendar offering plenty of opportunities to meet neighbors and stay involved. Enjoy the clubhouse, swimming pool, shuffleboard courts and fitness area. Ideally situated between Sarasota and Venice, you’ll have easy access to boutique stye shopping, multiple dining options, theaters, performing arts venues, and stunning Gulf beaches. Everything you love about the Florida lifestyle just minutes away. This is relaxed, low-maintenance living in a welcoming community. Come see why so many love calling The Arbors home!

23 Siesta Circle W, Osprey/Nokomis
$3,700,000
5 Beds ⋅ 5 Baths ⋅ A4706333 MLS
Welcome to extraordinary living! This completely private oasis is perfectly positioned along North Creek in The Oaks Bayside, one of the most sought-after communities in South Sarasota. Situated on a lot and a half, the view is peppered with lush foliage, creating total seclusion and the feel of a luxury retreat. One of the most desirable floor plans in the community, with open flow and complete separation from the master suite and guest accommodations, creates a comfortable and highly functional living space. The casita provides the perfect separate space for an office, a studio or long-term guest accommodations, with stunning views from the second floor. Fine finishes and quality craftsmanship are showcased throughout this home, custom built by renowned contractor Baron Construction. Features include French oak flooring, quartz countertops, premium appliances, and numerous custom details. The combined living and dining area provides an ideal setting for entertaining, opening directly to the outdoor pool and spa. For more casual gatherings, the spacious kitchen and breakfast nook flow seamlessly into the family room and out to the covered outdoor living space. This screened area is beautifully designed with a pool and spa, and grill. The covered areas and ceiling fans provide comfort for al fresco dining. The lots’ site is spectacular, with great water views, and areas to launch your kayak or paddleboard. Add in the practical features like a newer roof, oversized three car garage and huge pantry and you have found a home of distinction with no peer. The Oaks Bayside is a gated bayfront community within The Oaks. The distinguished private club offers 2 championship golf courses, pickleball and tennis courts, a state-of-the-art WellFit Center, exquisite dining options and a celebrated social calendar. The location provides convenient access to downtown Sarasota, dining, nightlife, and the cultural amenities of the Gulf Coast. Club membership is required with home ownership. There is currently no waiting list for either Golf or Sports/Social membership.

324 Osprey Point Drive, Osprey/Nokomis
$1,295,000
3 Beds ⋅ 2 Baths ⋅ A4706711 MLS
Impeccable is the only way to describe this charming property! This stunning 3 bedroom, 2 bathroom residence has been completely remodeled to create a luxurious yet comfortable, livable home. No detail has been overlooked in the complete renovation, making it truly gorgeous and unique. The interior is incredible and has so many high-end features; tile flooring designed to look like wood, quartzite countertops, a stylish coffee bar, and a beautifully crafted hood vent. The recent addition of an entire deck off to the side of the home enhances the outdoor living space. The deck includes a canopy that extends to cover part of the area, providing shade for the dining table, swinging chair, and grill. Additionally, a hot tub has been added for your relaxation. The home boasts three bedrooms, with one currently being used as an office. The previously enclosed Florida room has been transformed into a spacious family room, perfect for gatherings. The interior design, crafted by a professional, ensures that no detail no matter how big or small has been missed. The property also features a huge yard, the largest in the neighborhood, providing ample space for outdoor activities, and the pièce de résistance, a dreamy view of the pond. Residents enjoy access to a community pool and clubhouse, both within walking distance from the house. Plus, landscape maintenance is included, making it a hassle-free living experience. With mandatory membership, residents can enjoy all the amenities The Oaks offers. There is currently no waiting list for either Golf or Sports/Social membership.

17 Bayhead Lane, Osprey/Nokomis
$700,000
3 Beds ⋅ 3 Baths ⋅ A4705730 MLS ⋅ 3621 BLDG.
Embrace an active lifestyle with comfort and luxury in this beautifully situated residence at Meridian at The Oaks Preserve. Located in Building 5, this lovely condo is just steps from the Meridian residents-only pool, spa, and fitness room, making it easy to start your day with a workout or swim just outside your door. Afterward, you will come home to your condo with secure entry, private elevator and a great floor plan for comfortable living. Offered turn-key furnished, the light-filled interior provides generous storage and has beautiful, open views overlooking the Preserve and pool. With 3 bedrooms, 3 baths, a great room with dining room, kitchen with breakfast nook and a private, screened balcony, there is plenty of room for you and visiting guests to enjoy. As a member of The Oaks, you can take advantage of everything the club has to offer, including two championship golf courses, tennis and pickleball courts, a Junior Olympic community pool, recreational and social events, and incredible culinary options. Located in the heart of South Sarasota the location provides close proximity to the area’s beautiful Gulf beaches, dining and shopping venues and a wide range of cultural and recreational offerings. With its convenient location, inviting floor plan, and resort-style amenities, this is an exceptional opportunity to enjoy the Florida lifestyle at its finest. Club membership is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership.

3621 N Point Road Unit 403, Osprey/Nokomis
$655,000
3 Beds ⋅ 3 Baths ⋅ O6442446 MLS
Welcome to 700 Shadow Bay Way, an impressive 3-bedroom, 2.5-bath pool home with a den, 3-car garage and more than 2,500 square feet of living space in the highly desirable Woodlands at Rivendell. Set on an oversized corner lot, this spacious home offers a bright, open and functional floor plan with high ceilings, crown molding, a generous great room and a separate dining area ideal for both everyday living and entertaining. The den provides valuable additional space for a home office, library or possible fourth bedroom. The spacious eat-in kitchen offers abundant cabinetry and counter space, a breakfast bar, walk-in pantry and an open connection to the main living areas. The private primary suite includes direct access to the lanai, two walk-in closets and an ensuite bath with dual vanities, soaking tub and separate shower. Step outside to an expansive screened lanai surrounding the pool and spa, with a covered seating area and plenty of room to relax or entertain. Additional highlights include a split-bedroom layout, inside laundry, brick-paver driveway and walkway, mature landscaping and an attached 3-car garage. Rivendell is known for its tree-lined streets, lakes and natural surroundings, with a convenient Osprey location near Pine View School, Oscar Scherer State Park, shopping, dining, Gulf beaches, Venice and Sarasota. A wonderful opportunity to enjoy generous living space, a private pool and the Florida lifestyle in one of Osprey's established communities.

700 Shadow Bay Way, Osprey/Nokomis
$255,000
2 Beds ⋅ 2 Baths ⋅ A4705745 MLS ⋅ 2 BLDG.
TURNKEY Furnished 2 bed, 2 bath two story condo in the lifestyle rich community of Pine Run! Outdoor enthusiasts will love this 20 Acre mature landscaped neighborhood. Nearby, you will find nature parks, walking and biking trails, boat ramps, waterfront dining and minutes to beaches and downtown Venice! Within the community, you can enjoy TWO community pools, pickleball and tennis courts, clubhouse, fitness center and saunas in the community bathrooms. HOA includes Water, Sewer Trash and Pest control. Included with the unit is an assigned outdoor carport space and storage closet. Enjoy the natural lighting and privacy this unit greets you with as you walk through the door. The soaring ceilings bring in natural lighting all day. Updated kitchen with newer, barely used modern appliances and updated cabinetry and countertops. Reverse Osmosis Water softener has been installed to provide the top quality water. On the main floor, you will find a light and bright living room that leads to the oversized screened-in private lanai. Enjoy the wildlife whilst sitting up in the mature trees. The dining area also has a breakfast bar for additional entertaining space. Down the hallway you will find the primary bedroom with two closets, balcony access and entrance to the hallway renovated full bathroom. Also on the main floor is a stackable washer and dryer and large storage closet. Take the serial staircase to the secondary bedroom loft with full bathroom and two closets. The oversized closet is ideal for a walk-in or year round storage. The community is full of life and energy, especially in the winter seasons, and with all of the waterfront dining, parks and attractions nearby, you will always have something to do! Conveniently located near shopping, dining, downtown Venice, Sarasota, major roadways and schools.

109 Woodland Place, Osprey/Nokomis
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