The Oaks Real Estate

The Oaks Real Estate

Welcome to The Oaks, a stunning subdivision nestled in the heart of Florida, where luxury meets tranquility. This picturesque community is perfectly situated to offer residents the best of both worlds—serene living with convenient access to vibrant city life. The Oaks is renowned for its beautifully designed homes, lush landscapes, and a strong sense of community that makes it an ideal place for families, retirees, and everyone in between.

As you enter The Oaks, you'll be greeted by tree-lined streets and meticulously manicured lawns that create an inviting atmosphere. The subdivision features a variety of architectural styles, from modern masterpieces to classic Florida designs, ensuring that there’s a perfect home for every taste. Residents enjoy spacious lots, offering ample outdoor space for family gatherings, gardening, or simply soaking up the sun.

Community amenities are abundant in The Oaks. Enjoy leisurely strolls or bike rides along scenic paths, or take advantage of the community clubhouse, which is perfect for social events and gatherings. The subdivision also boasts a sparkling pool, tennis courts, and playgrounds, making it easy to stay active and engaged with neighbors.

Location is key, and The Oaks doesn't disappoint. Just a short drive away, you'll find shopping, dining, and entertainment options that cater to all lifestyles. Plus, with easy access to major highways, commuting to nearby cities or exploring Florida's beautiful beaches is a breeze.

Discover the charm and warmth of The Oaks, where every day feels like a vacation in paradise. Come and experience the lifestyle that awaits you in this exceptional community!

Newest Listings in The Oaks

642 Trenton Way, Osprey
$2,150,000
4 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
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
141 Sugar Mill Drive, Osprey
$1,700,000
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
2912 Boating Boulevard, Kissimmee
$470,000
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
6519 W Newberry Road Unit 108, Gainesville
$114,900
2 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 32607 Zip Code
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
75 Osprey Point Drive, Osprey
$1,595,000
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
156 Bishops Court Road, Osprey
$1,289,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
One or more photo(s) has been virtually staged. An expansive double lot, a quiet cul-de-sac setting and preserve views with no rear neighbors make this Bishops Court residence an exceptional private retreat. Mature oaks and lush landscaping frame the property, creating a sense of space and seclusion within this intimate gated enclave of The Oaks Preserve. Designed by renowned architect Frank Folsom Smith, the home pairs timeless architectural character with thoughtfully curated updates. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths and inviting spaces that make the most of its natural surroundings. Hardwood floors, custom millwork, crown molding, vaulted ceilings, plantation shutters and two fireplaces bring warmth and character throughout. The great room flows into the screened Florida room and outdoor living areas, keeping the peaceful setting in view. A built-in serving bar and wine chiller enhance the dining room, while the updated kitchen features custom white cabinetry, granite countertops, stainless steel appliances, an oversized island and designer lighting. A Sonos sound system extends throughout the home. The primary suite offers its own quiet retreat, with vaulted ceilings, a bay-window sitting area and direct outdoor access. Renovated in 2023, the spa-inspired bathroom features marble-look tile, a frameless glass shower, dual vanities and a freestanding soaking tub beneath a skylight. The additional bathrooms have also been extensively renovated with designer fixtures and finishes. Custom storage, built-ins and shiplap detailing bring the same considered style to the laundry room. Upstairs, a spacious bonus room with a fireplace opens to a newly renovated second-story deck overlooking the treetops. Freshly painted in 2026 and complete with a full bathroom, this versatile level can serve as guest accommodations, a media room, home office, art studio or secluded lounge. Outside, the generous lot gives the pool area a remarkable sense of privacy. A seven-foot-deep heated pool and spa are surrounded by brick pavers and tropical landscaping, with tranquil preserve views beyond. 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, where Golf or Social Membership is required with homeownership. Club amenities include two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a fitness center, fine and casual dining, and a year-round social calendar. The Oaks Club has been recognized as a Platinum Club of America, a Distinguished Emerald Residential Country Club and an Audubon International Certified property. Located in Osprey between Sarasota and Venice, the home places Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota and historic Venice within easy reach.

156 Bishops Court Road, Osprey
97 Sugar Mill Drive, Osprey
$1,950,000
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
6519 W Newberry Road Unit 204, Gainesville
$89,000
2 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 32605 Zip Code
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
51 Mac Ewen Drive Unit 14, Osprey
$285,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
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
51 Macewen Drive Unit 5, Osprey
$235,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
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
410 Blue Garden Lane, Osprey
$699,000
The Oaks SubDv. ⋅ 34229 Zip Code
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
Sebastian Drive, Spring Hill
$85,000
The Oaks SubDv. ⋅ 34609 Zip Code
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
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