Oaks The Real Estate, Homes, Condos for Sale in Osprey/Nokomis, FL - Ed Grabowski

One of the last remaining opportunities to build a custom luxury estate in The Oaks Bayside, one of Sarasota’s distinguished private country club communities. Behind 24-hour staffed gates, this generous 25,735-square-foot homesite offers a rare chance to create a custom residence with the builder of your choice in a serene, established setting known for its stately oaks, winding streets, natural beauty and impressive estate homes. The Oaks Bayside is treasured for its peaceful, Old Florida character, with a neighborhood setting along Little Sarasota Bay and beautifully landscaped streets that reflect the elegance and privacy of this exclusive community. Design your dream home in a tranquil environment while enjoying access to the exceptional lifestyle The Oaks is known for. Club amenities include three restaurants, a ballroom, two 18-hole championship golf courses, award-winning racquet programs with 12 Har-Tru hydro-grid tennis courts, four pickleball courts, official croquet green, state-of-the-art fitness center, Junior Olympic heated community pool, bocce, basketball court and playground. The Oaks has earned recognition as a Platinum Club of America, Emerald Club of the World, Distinguished Club of the World and one of America’s Healthiest Clubs. Ideally near nationally ranked Pine View School, the Legacy Trail, world-famous Siesta Key, shopping, dining, cultural venues, entertainment and Gulf Coast beaches, this exceptional homesite offers a rare opportunity to enjoy privacy, prestige and the full country club lifestyle in one of Sarasota’s premier gated communities.

216 Osprey Point Drive, Osprey

$1,900,000

5 Beds ⋅ 7 Baths ⋅ Oaks The SubDv. ⋅ 34229 Zip Code

Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a spacious 3-car side-load garage. Stately columns welcome you to the grand double-door entry, where you’ll step inside to find gleaming marble floors, soaring ceilings, and plantation shutters that set the stage for timeless sophistication. The thoughtfully designed floor plan includes a private office with built-ins and French doors, and a flexible open space with a dramatic backlit tray ceiling—ideal for a formal dining room, music room, or library. The formal living room features a stunning picture window that brings the outdoors in, along with a cozy fireplace and direct access to the luxurious pool area. The chef’s kitchen is a true showstopper, complete with an aquarium window breakfast nook, expansive breakfast bar, dual sinks, center island, double wall ovens, and a butler’s pantry. It opens seamlessly into the family room, where sliding glass doors, a wood-burning fireplace, wet bar, and built-in desk create a warm and inviting space for everyday living and entertaining. The primary suite is a tranquil retreat with a sunlit sitting area, private access to the pool, and a spa-inspired en suite bath with a walk-in shower and soaking tub that overlook your private tropical paradise. Step outside to your own resort-style oasis, where a sparkling pool, separate spa, travertine deck, and covered patio offer the ultimate in outdoor living. With over 6,000 square feet of living space, this estate features 5 bedrooms, 5 full bathrooms, and 2 half baths, along with two newer A/C systems (2023). As a resident of The Oaks, you’ll have access to The Oaks Club’s world-class amenities, including two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center, and fine dining. Ideally located near top-rated Pine View School, Historic Spanish Point, Casey Key, and Oscar Scherer State Park, this home offers both tranquility and convenience. Don’t miss your chance to own this exceptional estate—schedule your private tour today and experience the luxury of life at The Oaks Bayside.

340 Osprey Point Dr, Osprey

$1,250,000

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

This 4 bedroom, 4 full bath luxury home overlooks the 14th hole of the Heron Course and is great for indoor and outdoor entertaining. The double door entrance opens to a bright and open living room with high ceilings and crown molding. Living room sliding glass doors open to the pool with a beautiful view of the golf course. The formal dining room have floor to ceiling windows. Crown molding and custom-made window treatments throughout the home. The primary bedroom suite occupies one side of the home with direct access to the pool. Custom his and her walk-in closets and beautiful wood floors throughout. Office with large window and wood floors. The family room is off the kitchen, with view of the extended covered Lanai, pool and golf course. Breakfast table off the kitchen and family room. The kitchen includes cherry wood cabinets, Stainless steel appliance, newer Refrigerator, Double oven, Built-in microwave, Countertop stove, Built-in wet bar with space for a Wine cooler Extra storage closets in the hall. Large sale water pool with jacuzzi, outdoor shower, laundry room with built-in cabinets, two zoned A/C (3 and 4 years old.)Electric hurricane shutters, NEW ROOF 7/24.

491 E Macewen Drive, Osprey

$1,885,000

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

**IMPRESSIVELY UPDATED, GOLF ESTATE WITH WATER VIEW in the Popular OAKS COUNTRY CLUB Community** situated on the 15th fairway of the interior, Heron Golf Course and with South-facing Pool/Lanai. Featuring 4BEDS Plus OFFICE/DEN, 4 FULL and 1 HALF BATHS, Magnificent Updates and Impeccable Design both inside and out! 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, 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. Equity OR Social Membership is required and available.

621 N Macewen Drive, Osprey

$3,000,000

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

How to describe a masterpiece?! This home was completed in February 2023, and is ready for a new owner to enjoy the breathtaking features it offers. This home is still under the builders warranty! It’s like getting a new home without the two year wait for a custom built home! This gem is truly a one of a kind in The Oaks Country Club Community. The Oaks is considered to be the pinnacle in country club living and best of all THE SELLERS ARE OFFERING TO PAY THE $100,000 CAPITAL CONTRIBUTION ON BEHALF OF THE BUYER! (With acceptable contract.) The owners have painstakingly thought out each detail from purchasing the lot, drawing up plans with an architect to having the home custom built by Henson Contractors, to making sure every item was of the finest quality. The home is situated on one and a half lots, making for a grand appearance with a circular paver drive and a side paver drive leading to the oversized 3 car garage with epoxy floors and built-in cabinetry. The interior exudes quality from the minute you arrive at the custom 4 foot wide solid mahogany front door. Entering the home you will come upon the great room with expansive 24’ ceiling height and a chandelier that is one of the focal points. Other features of the greatroom include built-in bookcases, fireplace and coffered ceiling. Open to the great room is a wet bar enclave just perfect for entertaining. Another breakfast bar area opens to the kitchen. Ah, the kitchen! Every detail is of highest quality including a Miele steam/convection built-in oven, two kitchen sinks (a third sink in the bar enclave), propane gas Wolfe range, custom cabinetry, Sub-zero 42” wide refrigerator, a pantry with sliding ladder and more! The master suite is a dream come true! Two walk in closets that should satisfy those looking for the ultimate in closets. A triple mirrored dressing area in also a unique feature. The master bath is exceptional with large double headed shower and plenty of cabinet and counter space. Currently used as an office, the fourth en-suite bedroom has rich wainscoting, and a private bath. The den is currently used as a piano room and offers floor to ceiling book cases. Upstairs is the loft large loft, another bedroom and bath. Doors lead to the second floor balcony with retractable awning. Other features include an AV closet, a drop zone room for a future elevator. The outdoor living space is outstanding! Large covered lanai with two seating areas, in-wall gas fireplace, plus 3 remote controlled hurricane shutters, travertine flooring, 18x32’ salt water, heated pool with sun shelf and spa. Expansive clear view screening, outdoor shower, outdoor kitchen. Other features are impact windows throughout, “Lutron” programmable light switches, 3 air handlers, dream laundry room, powder room with Murano vessel sink, two tankless recirculating hot water heaters, Generac 38 kw whole-house standby generator, whole house water filter, “control4” home automation (security, lighting and comfort/temperature)and extensive landscaping gives a well established look. Reading a list of features is nothing compared to coming to see this showplace! If you are in the market for a classic and timeless new home, you will not find anything finer on the market! HOA fees do not include mandatory Country Club Fees. Check pricing schedule for details. Come take a look at The Oaks Country Club and if your are not familiar with The Oaks it is a historic landmark community - where luxury lives!

350 Sugar Mill Drive, Osprey

$2,200,000

5 Beds ⋅ 7 Baths ⋅ Oaks The SubDv. ⋅ 34229 Zip Code

Introducing The Grand Estate at The Oaks Bayside! Roof is brand New 1 year old. Step into a world of opulence and tranquility, nestled within the exclusive gates of The Oaks Bayside. This remarkable residence stands as a testament to luxury living, enveloped by lush greenery, majestic oak trees, and vibrant tropical flora that set the stage for an extraordinary retreat. As you approach, a captivating driveway adorned with elegant pavers leads to the 3-car side-load garage, ensuring ample space for your vehicles. Welcoming you to the front porch are stately columns that frame the grand double-door entry, hinting at the lavish interior that lies beyond. Upon crossing the threshold, be prepared to be awed by the lavish details that define this residence. Marvel at the pristine marble flooring that gleams under the abundant natural light that bathes the space. The exquisite plantation shutters grace every window, inviting you to discover the myriad of exceptional features. To the left, an exquisite office awaits, replete with built-in bookshelves and a desk, ideal for productivity and focus. Pocketing doors provide an oasis of quiet when needed. To the right, an expansive open space with a backlit tray ceiling presents endless possibilities—a perfect enclave for your grand piano, a library of cherished books, or an elegant formal dining room. Ahead lies the formal living room, where a window of grand proportions transforms the outdoors into an integral part of your living experience. Towering ceilings, a crackling fireplace, and seamless access to the private pool area create an ambiance of comfort and sophistication. Prepare to be enamored by the kitchen's design, where a charming breakfast nook overlooks the pool through an aquarium window. A sprawling breakfast bar, dual sinks, an island for culinary creativity, a double wall oven, and a butler's pantry define the culinary haven. This space seamlessly transitions into the family room, where sliding glass doors open to the pool, accompanied by a wood-burning fireplace, a wet bar, and a convenient built-in desk—a haven for family togetherness. The master suite beckons with its spaciousness, complete with a cozy sitting area bathed in sunlight and pool access through sliding glass doors. The en suite bath boasts a walk-in shower and a garden tub with picturesque windows framing your private tropical haven. Outside, discover the ultimate private oasis—your pool area. A resplendent pool and separate spa take center stage, embraced by a travertine deck and a covered patio, making every day feel like a vacation. With 6000 square feet of living space, 5 bedrooms, 5 full bathrooms, and 2 half baths, this estate is a realm of comfort and luxury. 2 AC systems are 2 years old, And that's just the beginning! As a resident of The Oaks, you gain access to The Oaks Club, offering two golf courses, tennis courts, pickleball courts, a croquet court, a well-equipped fitness center, and exceptional dining. Conveniently situated near esteemed institutions like Pine View School, Historic Spanish Point, Casey Key, and Oscar Sherer State Park, you'll enjoy the best of both worlds—tranquility and accessibility. Your dream home is waiting. Schedule your private showing today and embrace a life of timeless elegance!

340 Osprey Point Dr, Osprey

$700,000

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

PRICE IMPROVEMENT! Inquire about INCENTIVES! Don't miss this chance to belong to this Top Rated Country Club! Welcome to "BISHOPS COURT" at The Oaks Preserve a MAINTENANCE-FREE gated neighborhood where the streets are lined with canopy trees, rich lush fauna is all abound and wonderful memories begin! This comfortable 3 bedroom, 2 bath home was custom designed by the highly regarded builder Lee Wetherington! It is Move-In Ready, freshly painted interior, new carpets in the bedrooms and freshly cleaned and sealed grout. Once you enter the front door your eyes are drawn to a beautiful view of the magnificent Preserve that the home backs up to. A very private oasis on an oversized lot and with almost 2,200 square feet there is wonderful living space inside and out. As you explore you will find a great room with high 14ft ceilings, tile floors, lots of light and an open floor plan. The architectural details are not to be missed. The master bedroom is a very spacious retreat with two walk-in closets and a huge window giving a picturesque view of the nature behind. The master bath features a separate walk-in shower with a soothing over-sized tub. The floor plan offers room and privacy for residents and their guests. Open the sliding glass pocket doors and listen to the tranquility of nature come to life with amazing birds and wildlife. The pristine pool is perfect for laps and the spa is a delight after a long day of fun Club life. It is your very own tropical oasis. Entertain your friends or relax and enjoy a quiet evening with a tapestry of stars above. The Oaks Preserve offers 24 hour gated security. Bishops Court residents also have use of the community pool & clubhouse and enjoy a quiet lifestyle among the 200 acres of lush natural beauty. The Oaks Club is Sarasota’s finest golf and country club community, with numerous accolades. The amenities include 2 world class golf courses, 12 HarTru tennis courts, croquet court, new fitness center, 4 pickleball courts, heated junior Olympic sized pool, fine dining and an abundance of social activities. You will live just minutes from the Legacy Bike Trail, a short drive to the nationally rated number “1” sandy beach on Siesta Key. Oscar Scherer State Park is just round the corner, cultural downtown Sarasota is 20 minutes away not to mention all the other activities and culture that the Gulf Coast living has to offer. Club membership is required and available with either golf equity or social. The Oaks Golf and Country Club is the only country club in Central Florida to be named a Distinguished Emerald Club of the World. Paradise awaits.

29 Bayhead Lane, Osprey

$1,525,000

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

**IMPRESSIVE COUNTRY CLUB ESTATE with WATER and GOLF COURSE VIEW on an OVERSIZED CORNER LOT** Located behind the Secure Gates of The Oaks-Clubside Country Club neighborhood, this Meticulously Maintained, Single Story Home with an Ideal Open Floorplan offers 3Beds + Office/Den + 3Baths + 3Car Garage and is situated on a LARGE 0.83 ACRE LOT with Expansive, Circular Driveway. MANY RECENT UPDATES including NEW HURRICANE IMPACT WINDOWS (2023), NEW ROOF (2021), COMPLETELY RENOVATED POOL & SPA + AUTOMATION (2022), HVAC + NEW DUCTWORK (2020-2021), FRESHLY PAINTED Inside and Out, WHOLE HOUSE WATER FILTRATION/SOFTENING, and MUCH MORE! High Ceilings, Crown Moldings, Tray Ceilings and Custom Built-In features are just a few of the many upgrades. The expansive owner’s suite with multiple walk-in closets is complemented by spacious guest bedrooms in a desirable, split floorplan. The Expansive Outdoor Living area offers distant water and golf course views in a private setting from your screened lanai with multiple covered areas and Gorgeous, Heated, Saltwater Pool & Spa. 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, 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 available. **ENJOY THE 3D VIRTUAL TOUR**

558 Dove Pointe, Osprey

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