The Oaks Real Estate

The Oaks Real Estate

Welcome to The Oaks, a picturesque subdivision nestled in the heart of Florida, where serene landscapes meet a vibrant community spirit. This enchanting neighborhood is a hidden gem, offering residents a perfect blend of tranquility and convenience.

The Oaks is renowned for its lush greenery and beautifully manicured lawns, providing a serene backdrop for family life. As you stroll through the tree-lined streets, you’ll discover an array of charming single-family homes, each exuding unique character and warmth. With spacious layouts and modern designs, these homes cater to a variety of lifestyles, whether you’re a growing family or seeking a peaceful retirement retreat.

One of the standout features of The Oaks is its commitment to community living. Residents enjoy access to a wealth of amenities, including a sparkling community pool, playgrounds, and walking trails that invite outdoor adventures. The neighborhood fosters a strong sense of camaraderie, with regular events and gatherings that bring neighbors together, creating lifelong friendships.

Conveniently located, The Oaks offers easy access to major highways, making commutes a breeze. Nearby, you’ll find top-rated schools, shopping centers, and dining options, ensuring that everything you need is just a stone's throw away.

Whether you’re looking to settle down in a welcoming community or seeking a vibrant lifestyle, The Oaks in Florida is the perfect place to call home. Come experience the charm and warmth of this delightful subdivision – where your dream home awaits!

Newest Listings in The Oaks

452 Blue Garden Lane, Osprey/Nokomis
$1,925,000
3 Beds ⋅ 4 Baths ⋅ A4711003 MLS
Experience exceptional luxury and privacy in this Updated, custom Bo MacEwen residence, ideally situated on a beautifully landscaped cul-de-sac homesite in the prestigious gated community of Oaks Bayside. A welcoming approach features a long paver driveway, side-entry garage, and generous guest parking. Inside, architectural details take center stage with a dramatic two-story domed foyer, 11-foot ceilings, custom millwork, crown molding, tray ceilings, travertine flooring, abundant natural light, and oversized doors throughout. Designed for both elegant entertaining and comfortable everyday living, the open great room features a fireplace and flows seamlessly into a chef-inspired kitchen appointed with custom wood cabinetry, granite countertops, induction cooktop, double wall ovens, microwave drawer, and premium built-in appliances, including a wine cooler. The expansive primary suite offers a private retreat with ample sitting space, generous walk-in closets, and a beautifully appointed bath featuring dual vanities, dressing area, soaking tub, and glass-enclosed shower overlooking a secluded garden. Two additional guest suites, each with private en-suite baths, are thoughtfully positioned on the opposite side of this split floor plan. Outdoors, a recently renovated private courtyard creates an exceptional setting for relaxation and entertaining, featuring more than 1,500 square feet of covered and open-air space, a heated pool and spa, and convenient access to the main living areas and pool bath. Additional features include central vacuum, zoned HVAC with enhanced air filtration, hardwired security, integrated pool controls, and a Sonos/Sonance theater system. A distinctive combination of craftsmanship, architectural character, and private outdoor living in one of The Oaks' most desirable neighborhoods. The nearby, Private Dock on the Intracoastal Waterway is a cherished amenity of the Oaks-Bayside residents. 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**

452 Blue Garden Lane, Osprey/Nokomis

Listing courtesy of GENEROUS PROPERTY. 941-275-9399
642 Trenton Way, Osprey/Nokomis
$2,150,000
4 Beds ⋅ 5 Baths ⋅ A4709515 MLS
Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically situated on a half-acre corner lot surrounded by beautiful landscaping with views of the lake and the 14th Fairway of the Heron Course. This 4 bedroom residence has 4 full baths, 1 half bath, a formal living room with pool views, a separate formal dining room, and an open gourmet kitchen with gas cooktop, stainless appliances, two wallovens, a breakfast bar, an adjoining dining area and two pantries. The kitchen opens to an expansive family room overlooking the pool. The spacious master suite features a large luxury bath, two large his-and-hers closets and a lovely sitting area overlooking the pool. All three additional bedrooms are en suite. A dedicated office with built ins and a versatile bonus room/game room adds valuable flexibility for a wide variety of lifestyles. The large and lovely lanai includes an outdoor grill and bar, covered seating, awnings, and a freeform pool and spa overlooking the water and golf course. With a four-car garage, abundant storage and numerous updates, including a new roof installed in December 2024 (with warranty), a new pool heater installed in 2024, new central air conditioning (2 units, 2 zones) in 2022, freshly painted interior and exterior, this home is the perfect choice for those who want to live in comfort and luxury. A complete list of updates is available. The mandatory Membership to The Oaks Club will provide everything for living a country club lifestyle; two championship golf courses, tennis and pickleball courts, a regulation croquet lawn, state-of-the-art wellness center and a wide array of dining and social options. There is currently no waiting list for either Golf or Sports/Social membership.

642 Trenton Way, Osprey/Nokomis

Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411
4662 The Oaks Drive, Marianna
$389,000
4 Beds ⋅ 3 Baths ⋅ 796431 MLS
Welcome to 4662 The Oaks Dr, where space, comfort and flexibility come together in an inviting one story brick ranch situated on a spacious lot in an established Marianna neighborhood. Offering approximately 2400 sq ft, 4 bedrooms and 3 full baths, this home features a generous living room with fireplace, a comfortable dining area and functional kitchen with plenty of room for everyday living and entertaining. A recently added second primary suite is a standout feature, offering added privacy along with a beautifully appointed bath featuring a double-entry walk-through tiled shower and freestanding soaking tub - creating the perfect private retreat or an ideal option for multigenerational living. Outside, enjoy a fenced backyard, mature trees, additional storage and plenty of space for entertaining, pets, gardening or recreation. The established neighborhood offers a convenient location near Marianna's schools and local sports complex, plus an easy drive to Alabama. With it's flexible floor plan, abundant indoor and outdoor space, and welcoming setting, this home is ready for its next chapter.

4662 The Oaks Drive, Marianna

Listing courtesy of Chipola Realty.

2912 Boating Boulevard, Kissimmee
$450,000
4 Beds ⋅ 2 Baths ⋅ TB8540714 MLS
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

Listing courtesy of MARK SPAIN REAL ESTATE. 855-299-7653
6519 W Newberry Road Unit 108, Gainesville
$114,900
2 Beds ⋅ 2 Baths ⋅ GC541198 MLS ⋅ 100 BLDG.
Fully updated 2 bed 2 bath in The Oaks. Great location near the University of Florida, Santa Fe College, and walking distance to North Florida Hospital. This second floor condo has every update imaginable. As you enter you are greeted with a large living room flowing to a screened patio with new tile flooring throughout. Both bedrooms are spacious, with plenty of closet space and room for a desk or additional seating. Bathrooms feature tile flooring and new vanities. Upgrades include new kitchen cabinets, wood countertops, flooring, freshly painted walls, trim, vanities, HVAC, and appliances. Community amenities include a pool, fitness center, and clubhouse. Perfect for primary residence or renting out while your son or daughter goes to school at UF or Santa Fe. Airbnb and short term rentals are allowed. Direct bus routes on Newberry Rd.

6519 W Newberry Road Unit 108, Gainesville

Listing courtesy of WATSON REALTY CORP- TIOGA. 352-274-2600
75 Osprey Point Drive, Osprey/Nokomis
$1,595,000
4 Beds ⋅ 4 Baths ⋅ A4695145 MLS
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/Nokomis

Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411
97 Sugar Mill Drive, Osprey/Nokomis
$1,950,000
5 Beds ⋅ 6 Baths ⋅ A4691789 MLS
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/Nokomis

Listing courtesy of PALM PARADISE REALTY GROUP. 239-955-7256
6519 W Newberry Road Unit 204, Gainesville
$89,000
2 Beds ⋅ 1 Baths ⋅ GC539890 MLS ⋅ 200 BLDG.
Attention Investors! Prime Location on Newberry Road Excellent opportunity in a highly desirable area—directly across from HCA Florida North Florida Hospital with easy access to I-75. Just a short walk to the Oaks Mall and minutes from restaurants, shopping, Santa Fe College, the University of Florida, and public transportation—making this an ideal rental property. Located in Building 200 on the first floor, this 2-bedroom, 1-bath unit features an open-concept floor plan, new refrigerator and stove, and in-unit laundry for added convenience and tenant appeal. The community offers great amenities, including a clubhouse, pool, fitness center, sidewalks, and ample open parking. Move-in ready with strong rental potential—an excellent addition to any portfolio!

6519 W Newberry Road Unit 204, Gainesville

Listing courtesy of COLDWELL BANKER M.M. PARRISH REALTORS. 352-335-4999
51 Mac Ewen Drive Unit 14, Osprey/Nokomis
$285,000
1 Beds ⋅ 1 Baths ⋅ A4690371 MLS ⋅ 51 BLDG.
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey/Nokomis

Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411
51 Macewen Drive Unit 5, Osprey/Nokomis
$235,000
1 Beds ⋅ 1 Baths ⋅ A4689838 MLS ⋅ Windsor Lodge BLDG.
Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey/Nokomis

Listing courtesy of 342 REAL ESTATE. 941-685-0509
410 Blue Garden Lane, Osprey/Nokomis
$699,000
A4679677 MLS
Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasota’s most prestigious gated golf and country club communities. Situated on a rare cul-de-sac lot, this generous parcel offers privacy, mature landscaping, and an ideal canvas for a custom residence. Enjoy convenient access to world-class amenities including championship golf, tennis and pickleball facilities, a WellFit fitness center, swimming, croquet, dining venues, and an active year-round social calendar (club membership required). The Oaks’ prime location places you minutes from the renowned beaches of Siesta Key, upscale shopping, fine dining, cultural venues, and the vibrant lifestyle of downtown Sarasota. Don’t miss this rare opportunity to build in one of the Gulf Coast’s most coveted addresses. Lot size approximately 0.55 acres. Membership in The Oaks Club mandatory with homeownership. Buyer to verify all information.

410 Blue Garden Lane, Osprey/Nokomis

Listing courtesy of ELITE PROPERTIES LLC. 941-924-5935
Sebastian Drive, Spring Hill
$85,000
TB8467322 MLS
Welcome to The Oaks subdivision convenienty Located on Florida's Nature Coast. This beautiful HALF ACRE lot boasts GREAT ELEVATION, NO FLOOD ZONE, HOA only $50 ANNUALLY, and only minutes from SHOPPING, DINING, and ENTERTAINMENT at Cortez Blvd/Mariner, ACCESS TO THE SUNCOAST PKWY , LOCAL HOSPITALS , SPORTS COMPLEX and PARK. Florida's Nature Coast boasts a Florida lifestyle like no other. Local boat ramps offer access to both the Gulf of Mexico and Pristine rivers, nearby tens of thousands of acres of State Forests offer endless recreation, and Charming Downtowns that offer Dining and Entertainment, something for everyone. Enjoy the pictures and call today !!!

Sebastian Drive, Spring Hill

Listing courtesy of DENNIS REALTY & INV. CORP.. salesmanager@dennisrealty.com
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