The Oaks Homes with Private Pool type

The Oaks Homes with Private Pool type

Welcome to The Oaks, an exquisite subdivision nestled in the heart of Osprey/Nokomis, Florida—an area renowned for its stunning landscapes, vibrant community, and proximity to the beautiful Gulf Coast. This charming enclave offers an idyllic lifestyle where luxury meets comfort, making it the perfect place for families and retirees alike.

The Oaks is a meticulously planned community that boasts an array of elegant homes, many of which feature private pools to enhance your outdoor living experience. Imagine stepping outside your door to your own personal oasis, where you can soak up the Florida sun, host summer barbecues, or unwind with a good book by the water. These homes are designed with both style and functionality in mind, offering spacious layouts, modern amenities, and lush landscaping that creates a serene retreat from the hustle and bustle of daily life.

Residents of The Oaks enjoy access to a wealth of community amenities, including picturesque walking trails, tennis courts, and a clubhouse perfect for social gatherings. The neighborhood’s prime location also means you’re just a stone’s throw away from the pristine beaches of Nokomis and Osprey, where you can indulge in sun-soaked days by the shore or enjoy water sports and fishing.

Living in The Oaks means embracing a lifestyle of leisure, luxury, and community. Whether you're looking to raise a family, retire in style, or simply enjoy the best that Florida has to offer, this enchanting subdivision provides the perfect backdrop for your dream home. Come discover the charm of The Oaks—where every day feels like a vacation!

Newest The Oaks Homes with Private Pool type

3 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Custom built by Emerald Homes, this beautifully updated 3 bedroom + bonus room, 3 bath residence, offers a bright, inviting layout with generous living spaces and thoughtful design throughout. Behind the gates of The Oaks Bayside, it is beautifully situated, set back on a lot that offers peace and privacy. The open kitchen is a home chef’s dream and serves as the centerpiece of the home. Showcasing custom cabinetry, expansive counter space, and high-end appliances, the layout is ideal for both everyday cooking and effortless entertaining. There is a breakfast bar, dinette that is flooded by filtered sunshine through the tinted aquarium window, as well as a formal dining room. The living spaces flow seamlessly, enhanced by abundant natural light and refined finishes that elevate the home’s incredible appeal. The master suite has extra insulation between the great room and the master bedroom wall, ensuring a quiet, private sanctuary. The room is spacious and features a spa-like master bath with a tub, large separate walk-in shower, dual sinks and an abundance of mirrors and lighting. Step outside to a lovely lanai, with pool, spa and outdoor kitchen. This space is perfectly designed for relaxing, hosting gatherings, or enjoying the tranquil Florida lifestyle year-round. This gorgeous home offers so much, you truly must see it to fully appreciate it! Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

141 Sugar Mill Drive, Osprey

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Located behind the gates of The Oaks Clubside, and just moments from the clubhouse, this 3 bedroom plus office, 4.5 bath home offers over 3,500 square feet of quiet elegance and beautifully updated living space. Set along the 4th hole of the Eagle Course, the property enjoys sweeping golf and lake views, along with the community’s signature bridge, adding a picturesque focal point to the landscape. Inside, the formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The beautifully updated kitchen has been redesigned with modern finishes and generous workspace providing both style and functionality for everyday living. It opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus there is a formal dining room and breakfast bar for flexible entertaining. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located 3rd bathroom. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. With no house on one side, this exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership. There is currently NO WAITING LIST for either Golf or Sports/Social membership.

362 Macewen Drive, Osprey

4 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34746 Zip Code

Virtually Staged. Welcome to this beautifully renovated home offering the perfect blend of luxury, comfort, and resort-style living! This move-in ready home features a brand-new roof installed in 2025, stylish tile flooring throughout, a fully updated interior, new appliances, and a built-in wine cooler that’s perfect for entertaining. Step outside to your private backyard oasis featuring a stunning screened-in pool completed in 2021, a fully equipped outdoor kitchen, and built-in speakers, creating the ideal space for relaxing or hosting family and friends. As a resident, you’ll also enjoy access to the community’s boating dock, tennis courts, and playground, providing endless opportunities for recreation and outdoor enjoyment. With modern upgrades, exceptional amenities, and a fantastic lifestyle, this home is one you won’t want to miss!

2912 Boating Boulevard, Kissimmee

5 Beds ⋅ 8 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota’s leading golf and country club.

916 Macewen Drive, Osprey

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property encompasses two buildable lots and includes a charming guest house, creating a rare and versatile estate setting. A grand foyer measuring approximately 12 feet wide by 19 feet long welcomes guests and leads to an impressive great room featuring soaring vaulted ceilings, a gas fireplace, and a dramatic bay window with built-in seating overlooking the beautifully landscaped grounds. Architectural details abound, including 14-inch crown molding, Palladian windows, wainscoting, skylights, custom lighting, and distinctive craftsmanship throughout. The home offers four bedrooms and four full bathrooms, thoughtfully designed to blend elegance, comfort, and timeless architectural character. Throughout the residence, quality construction and meticulous attention to detail reflect the vision of its celebrated designer. Step outside to discover a tranquil, resort-inspired setting featuring a sparkling pool, lush landscaping, and a separate guest house ideal for visitors, extended family, or a private office. In the evening, landscape lighting transforms the grounds into a serene retreat unlike anything else in the community. Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

75 Osprey Point Drive, Osprey

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless luxury residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac in Bishops Court, an intimate gated enclave within The Oaks Preserve in Osprey, Florida. Framed by lush conservation views and a canopy of mature oaks, the property blends classic architectural character with thoughtfully curated updates in one of the Sarasota area’s most prestigious private country club communities. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Crown molding, hardwood flooring, custom millwork, vaulted ceilings, plantation shutters, and two fireplaces create a warm yet elevated aesthetic throughout. The great room opens effortlessly to the screened Florida room and private outdoor living areas, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen. Custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting define the space. A Sonos sound system extends throughout the residence. The primary suite is a private retreat featuring vaulted ceilings, a bay-window sitting area, outdoor access, and a fully renovated, spa-inspired bathroom completed in 2023. Dramatic marble-look tile, a frameless glass shower, dual vanities, and a freestanding soaking tub positioned beneath a skylight create a serene, resort-like experience. The additional bathrooms have also been extensively renovated with elevated finishes and designer fixtures. In the laundry room, custom storage, shiplap detailing, and functional built-ins boast a refined aesthetic. Upstairs, a spacious bonus room, freshly painted in 2026, features a fireplace and opens directly to a newly renovated second-story deck overlooking the treetops. Complete with a full bathroom, this highly versatile level can serve as private guest accommodations, a recreation or media room, home office, art studio, creative retreat, or secluded lounge. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and peaceful preserve views with no rear neighbors. Recent improvements include a new pool heater, filtration system, pump and motor; new lanai screening and aluminum framing; exterior paint completed in 2025; a new main-level air-conditioning system; and a new second-story flat roof with a warranty. Ownership in The Oaks Preserve provides access to The Oaks Club. The Oaks offers an exceptional club-centered lifestyle just south of Sarasota, with two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active year-round social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has earned recognition as a Platinum Club of America, a Distinguished Emerald Residential Country Club, and an Audubon International Certified property, reinforcing its standing as a premier private residential club. The Oaks delivers an exceptional lifestyle in Osprey between Sarasota and Venice. Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota, and historic Venice are all within easy reach.

156 Bishops Court Road, Osprey

5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.

97 Sugar Mill Drive, Osprey

4 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34746 Zip Code

Positioned along the 13th hole of The Oaks National Golf Course in Kissimmee, this golf-front residence offers elegant interiors, updated systems and a layout designed for comfort and entertaining. The four-bedroom, two-and-one-half-bath home features a flexible floor plan with high ceilings and abundant natural light throughout. The first-floor primary suite overlooks the course and private pool, with a spacious bath offering dual vanities, soaking tub, separate shower and walk-in closets. The kitchen includes granite countertops, wood cabinetry, decorative backsplash, accent lighting, reverse osmosis system and newly installed appliances. A wine storage feature adds to the home’s entertaining appeal. Upstairs, three generously sized bedrooms are joined by a double loft-style flex space, ideal for use as a media lounge, home office or playroom. Outdoor living is enhanced by a custom pool and spa with slate waterfall, surrounded by slate decking, mature landscaping and a double-height screened enclosure. A professionally designed irrigation system supports the landscaped grounds. Smart-home features include Alexa-enabled lighting and a Ring doorbell. Recent upgrades include a new roof and HVAC system in 2020, along with a fully paid-off solar system offering long-term energy savings. Community amenities include tennis courts, parks and playgrounds, with convenient access to local shopping, dining and attractions.

1524 The Oaks Boulevard, Kissimmee

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

49 Osprey Point Drive, Osprey

3 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath residence in The Oaks Preserve offers the perfect blend of comfort, style, and privacy. And you can BUY WITH CONFIDENCE — THE PROACTIVE SELLERS HAVE COMPLETED INSPECTIONS IN ADVANCE TO SHARE WITH BUYERS, GIVING YOU CLARITY FROM THE START. No guessing…what you see, and what you don’t see, is what you get! From the moment you arrive at the pavered driveway, the pride of ownership is unmistakable. Double leaded-glass front doors open to a light-filled interior designed for effortless Florida living. Just off the entry, a dedicated home office features plantation shutters and a ceiling fan. The formal dining room showcases a decorative ceiling and a beautiful built-in buffet with glass-front cabinetry. The open kitchen features new granite countertops, stainless appliances, a breakfast bar, chef’s desk, and built-in wine and beverage cooler. The adjoining breakfast nook with an aquarium window, overlooks the sparkling pool and spa. The master suite is exceptionally spacious, offering a sitting area with built-in window seat and large walk-in closets with glass-front storage. The updated en suite bathroom has granite countertops, dual sinks, a soaking tub, separate shower, and marble accents. Two well-sized guest bedrooms provide generous closet space, and the updated guest bath includes granite and marble finishes. The air conditioned 2-car garage with epoxy flooring offers abundant storage. This home backs to a lush, tropical preserve, ensuring privacy for the pool and spa. The lanai features two distinct areas: a large, covered space with outdoor kitchen and ceiling fan for shaded dining, and a sun-splashed pool and spa area under a screened enclosure. You can also enjoy the nearby Bishopscourt community pool. 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

21 Bayhead Lane, Osprey

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. ROOF (2015). 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**

852 Macewen Drive, Osprey

3 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered driveway, and hurricane-rated patio and bedroom doors. All living areas have wood floors or Italian porcelain tile. The kitchen features a gas stove, Waterworks faucet, quartz countertops, modern stainless appliances, and solid wood cabinetry. The breakfast nook adjacent to the kitchen has aquarium glass windows offering a view of the pool and foliage. The family room glass doors stack behind the wall, providing views of the pool and preserve, and they are hurricane-rated. The owner's suite includes two walk-in closets, a linen closet and space for a sitting area or office. Hurricane-rated glass doors overlook the pool. There is a separate study/office/bedroom with built-in wood cabinetry and space and wiring for a media room. The guest suite has an ensuite bath updated with Quartz counters and a vessel sink. Enjoy the utmost in outdoor living with a stunning, PebbleTec POOL with Travertine deck while there is ample space for a spa or additional seating within the spacious screened lanai. Connections for an outdoor kitchen are also available. A beautiful new pavered driveway adds that special curb appeal. In addition to the metal, roll down hurricane shutters, there is an electric hurricane protective screen spanning the lanai area to protect outdoor furniture. The extra deep two car garage affords additional storage options. A collection of unique bougainvillea and crepe myrtle rounds out the gardens. This lot is located outside the FEMA flood zone Bishops Court in The Oaks Preserve is a 24-hour guard-gated community with walking and biking paths. Additionally, there is a year-round heated community pool nearby. 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**

13 Bayhead Lane, Osprey

Start Your Search