The Oaks Real Estate

The Oaks Real Estate

Welcome to The Oaks, a stunning subdivision nestled in the heart of Florida! This enchanting community offers a perfect blend of luxury, comfort, and natural beauty, making it an ideal place for families, retirees, and everyone in between.

Located in the picturesque landscape of Florida, The Oaks is renowned for its lush greenery and beautifully designed homes that cater to a variety of tastes and lifestyles. The subdivision features a diverse range of architectural styles, from modern masterpieces to charming traditional designs, ensuring that every resident finds their perfect sanctuary.

One of the standout features of The Oaks is its commitment to community and outdoor living. Residents enjoy access to meticulously maintained parks, walking trails, and recreational facilities that encourage an active lifestyle. The community is also home to a sparkling swimming pool, playgrounds, and picnic areas, making it a fantastic place for families to gather and create lasting memories.

Conveniently located, The Oaks provides easy access to nearby shopping centers, dining options, and entertainment venues, ensuring that everything you need is just a stone's throw away. Additionally, the subdivision is situated within a highly-rated school district, making it an attractive choice for families looking to provide their children with an exceptional education.

Whether you’re seeking a peaceful retreat or an active community, The Oaks has something for everyone. Experience the charm of Florida living in this vibrant subdivision where neighbors become friends and every day feels like a vacation! Come explore The Oaks today and discover your dream home in this delightful community.

Newest Listings in The Oaks

$1,900,000
5 Beds ⋅ 8 Baths ⋅ A4698153 MLS
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/Nokomis

Listing courtesy of PREMIER SOTHEBY'S INTERNATIONAL REALTY. 941-364-4000
$499,900
5 Beds ⋅ 3 Baths ⋅ 2154584 MLS
Spacious true 5-bedroom, 3-bath, 3,178 sq ft one-story in The Oaks at Oakleaf Plantation. Stone-and-stucco curb appeal on a large lot with a side-entry garage, fenced rear yard, covered lanai, and an expansive deck--perfect for Florida indoor-outdoor living. Inside, a triple-split, open floor plan offers both elegance and flexibility. The formal living room features crown moldings, while the formal dining room is finished with wainscoting and crown moldings for standout entertaining. The family room centers on a cozy fireplace framed by three graceful arched windows, flowing to a sunny breakfast area. The large kitchen is a true gathering space with a walk-in pantry, stainless steel appliances, breakfast bar, and generous prep areas and storage. The massive primary suite is a private retreat with a huge custom closet. The primary bath includes a relaxing garden tub, separate shower, and double vanity. Four additional bedrooms are thoughtfully placed for privacy

3738 Cardinal Oaks Circle, Orange Park

Listing courtesy of WATSON REALTY CORP.

$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
$179,500
2 Beds ⋅ 3 Baths ⋅ 2150493 MLS
MAINTENANCE FREE, Fully FURNISHED! END UNIT, GOLF Course Views. RELAX AND UNWIND! Newer HVAC, Newer Tankless Water Heater. Completely REMODELED! Close to the SPACE CENTER and the Port. Year-round residence, Investment Income, or a Seasonal Retreat, ENJOY MORE and worry less! Nestled along the Fairways of the PRIVATE Rockledge Country Club, this charming END UNIT offers the perfect blend of PEACEFUL GOLF COURSE LIVING and convenient access to everything the Space Coast has to offer! Start your mornings with coffee on the SCREENED PORCH as the sun rises over the lush greens and natural surroundings. Spend your afternoons enjoying the community POOL, playing a round of GOLF, exploring nearby BEACHES, or dining at one of the area's favorite local RESTURAUNTS. In the evenings, unwind in the comfort of your SPACIOUS home while taking in the tranquil views and gentle Florida BREEZES. Inside, you'll find a welcoming Open Layout designed for both RELAXATION and ENTERTAINING, with bright living spaces, a cozy fireplace, and 2 PRIVATE bedroom SUITES that provide comfort and flexibility for guests or family. Located in the heart of Rockledge, you're just minutes from waterfront parks, the Indian River, Cocoa Village, world-famous beaches, Kennedy Space Center, and easy access to Orlando. Embrace a LIFESTYLE FILLED WITH SUNSHINE, recreation, and the laid-back charm of FLORIDA LIVING. Come experience golf course living, natural beauty, and everyday convenience all in one exceptional Space Coast location!

1600 Woodland Drive Unit 8201, Rockledge

Listing courtesy of UNITED REAL ESTATE GALLERY.

$1,649,000
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
$4,790,000
4 Beds ⋅ 6 Baths ⋅ A4694716 MLS
Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey/Nokomis

Listing courtesy of DOUGLAS ELLIMAN. 941-867-6199
$1,289,000
3 Beds ⋅ 4 Baths ⋅ A4691664 MLS
One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac within The Oaks Preserve. The property is framed by lush conservation views and mature oak canopies and blends classic architectural character with thoughtfully curated updates. Professional lawn care and irrigation are covered by the monthly fees. Designed for both everyday comfort and effortless entertaining, the residence offers 3 bedrooms, 3.5 baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. Inside, refined architectural elements, including 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 spaces, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen featuring custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting. A Sonos sound system extends throughout the residence. The primary suite serves as a retreat with vaulted ceilings, a bay window sitting area, outdoor access, and a fully renovated spa-inspired bath 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. Additional baths have also been extensively renovated with elevated finishes and designer fixtures, while the updated laundry room introduces custom storage, shiplap detailing, and functional built-ins with a refined coastal aesthetic. Upstairs, a spacious bonus room with a fireplace opens directly to a newly renovated second-story deck. With a full bathroom, the second floor is an exceptional flex space ideal for guests, recreation, or private lounging among the treetops. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and serene 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, new air conditioning for the main floor, and a new second-story flat roof with a warranty. Located within the gated community of Bishops Court inside The Oaks Preserve, residents enjoy 24 hour guarded gates, maintenance-free living alongside access to one of the region’s premier private club lifestyles, featuring two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has been awarded the Platinum Clubs of America, Distinguished Emerald Residential Country Club, and Audubon International Certified designations. Located between Sarasota and Venice, Osprey is known for its natural beauty, waterfront lifestyle, and easy access to everyday conveniences. Residents are just moments from Siesta Key, downtown Sarasota’s dining and cultural attractions, marinas, shopping, Legacy Trail, and the renowned Pine View School, creating an ideal setting for both year-round living and seasonal enjoyment.

156 Bishops Court Road, Osprey/Nokomis

Listing courtesy of DOUGLAS ELLIMAN. 941-867-6199
$259,900
3 Beds ⋅ 2 Baths ⋅ GC539443 MLS
THIS property has it ALL! A solid concrete block home , 3 bedrooms / 2 bathrooms with a Den on 1 full acre in the quiet countryside with NO restrictions, minutes to the Manatee Springs State Park, Clay Landing public boat ramp to the Suwannee River and our local Golf and Country Club. A massive 40x20 RV Carport with a 30amp hookup, a 24x24 barn/workshop, a utility shed with private bathroom and insulated/enclosed perfect for a man cave or craft room or can be made into a guest house. A huge 62x40 pole barn with workshop, 50 amp RV hookup with power and dump station. This serene property is fully fenced with dual gates. Solid gorgeous home that has had every cell of every block drilled and pumped with new insulation around the house as well as re blown in insulation in the attic. Nice open living room, kitchen with wood cabinetry , dining room, laundry room with additional space perfect for storage or pantry , a den perfect for additional family gatherings. Each bedroom offers ample space and 2 bathrooms, one with a combo shower/tub and master bathroom has a walk in shower. New LVP laminate wood flooring, solid metal roof, AC approx 10 years old AND brand new generac ONLY One year old. Convenient location to town for all your dining, shopping and medical needs. Call today for YOUR tour! Accepting ALL loans!

8731 Nw 127th Place, Chiefland

Listing courtesy of LPT REALTY, LLC. 877-366-2213
$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
$99,000
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
$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
$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
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