The Oaks Homes for Sale

4 Beds ⋅ 3 Baths ⋅ B26061910 MLS ⋅ The Oaks BLDG.

Welcome to this beautifully updated Mirage model in the gated community of The Oaks of Hobe Sound. Ideally positioned on a private lakefront lot, this spacious home features impact windows & doors throughout, providing enhanced storm protection, energy efficiency, security, & peace of mind. The bright, inviting floor plan offers formal living & dining rooms, an open kitchen with a breakfast area, & a comfortable family room overlooking the backyard and lake. Upstairs, engineered hardwood flooring flows throughout. The expansive primary suite features a beautifully remodeled ensuite with a walk-in shower & elegant slipper tub. Three additional generously sized bedrooms provide plenty of space for guests or a home office. Custom Silhouette shades throughout the main floor. The interior was just freshly painted with new baseboards. HVAC was replaced in 2025. Enjoy tranquil lake views, exceptional privacy, and a spacious backyard with ample room to design a custom pool and outdoor retreat. Located in the gated community of The Oaks of Hobe Sound, residents enjoy lawn care, cable, internet, a resort-style pool and spa, a playground, and secure, gated entrances, all with low HOA fees. Just minutes from Hobe Sound Beach, Jimmy Graham boat and kayak launch, Gomez Preserve nature trails, and charming downtown Hobe Sound, this home offers the perfect blend of privacy, convenience, and Florida lifestyle.

7751 SE Heritage Boulevard, Hobe Sound

$995,000

4 Beds ⋅ 3 Baths ⋅ B26056435 MLS

Welcome to this stunning 2023 CBS-built home located in the highly desirable gated community of The Oaks in Palm City. Offering 4 bedrooms, 3 full bathrooms, and a spacious 3-car garage, this exceptional residence combines modern elegance with thoughtful design and an incredible backyard oasis. Step inside to discover a bright, open-concept floor plan with soaring ceilings, abundant natural light, and a chef's kitchen featuring a large center island, walk-in pantry, premium cabinetry, and seamless flow into the spacious living and dining areas—perfect for everyday living and entertaining. The owner's suite is a private retreat complete with a luxurious en-suite bathroom featuring dual vanities, a large walk-in shower, and an oversized walk-in closet. Three additional bedrooms and two full bathrooms provide plenty of space for family, guests, or a home office. The backyard is nothing short of spectacular and has been transformed into a private resort designed for entertaining. Completed in 2024, the custom-designed saltwater pool and spa feature premium finishes, a relaxing sun shelf (splash pad), and top-of-the-line Pentair smart automation, allowing you to control the pool, spa, lighting, and equipment directly from your smartphone. Beyond the pool, you'll find a beautifully appointed gazebo complete with a bar, creating the perfect setting for hosting family and friends. A dedicated sand recreation area with cornhole adds another fun gathering space, making this backyard ideal for weekend barbecues, game days, or relaxing evenings under the Florida sky. The fully fenced backyard offers privacy, security, and plenty of room for pets and children to play. Built to today's hurricane standards and offering the efficiency and peace of mind of newer construction, this home is truly move-in ready. Located in the gated community of The Oaks, residents enjoy a convenient Palm City location just minutes from top-rated Martin County schools, shopping, dining, championship golf, boating, parks, I-95, and Florida's Turnpike. This is a rare opportunity to own a nearly new home with an outdoor living space that rivals many luxury resorts. Every detail has already been completed—simply move in and start enjoying the Florida lifestyle.

1490 SW Lago Circle, Palm City

$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

$3,350,000

6 Beds ⋅ 9 Baths ⋅ B26054573 MLS

This classic Mediterranean estate in The Oaks has been completely reimagined, offering over 6,700 square feet of thoughtfully updated living space that blends timeless architecture with modern finishes. Featuring six bedrooms and seven and a half bathrooms, the home offers a clean, refined feel throughout. Natural light fills the residence, highlighting soaring ceilings and tile flooring that flow through the main living areas. The kitchen has been redesigned as a true focal point and features a striking fifteen foot Taj Mahal stone island, custom cabinetry, and high quality appliances. The layout offers expansive common areas along with dedicated spaces suitable for a home office, gym, or media room. Upstairs, the bedrooms are spacious and private, while the primary suite offers a calm retreat with an open layout, a large walk in closet, and a thoughtfully redesigned bathroom. Located within Boca Raton's gated community, The Oaks, residents enjoy a renovated clubhouse, full service spa, on site restaurant, fitness center, tennis and pickleball courts, basketball, a kids' playroom, and twenty four hour security. The community is zoned for top rated schools and is conveniently located near shopping, dining, and golf. A rare opportunity to own a fully reimagined residence in one of Boca Raton's most established communities. The information published and provided including but not limited to prices, measurements, square footages, lot sizes, features, finishes, and calculations are subject to errors, omissions or changes without notice. All such information should be independently verified. All parties should perform their own due diligence to verify all information.

17606 Circle Pond Court, Boca Raton

$1,350,000

4 Beds ⋅ 3 Baths ⋅ A11998115 MLS

*New Roof 2026* Full Impact Windows & Doors, Turn Key/Move in Ready, Large Lot (17,140 SQ FT), No HOA. Fully Renovated Palmetto Bay Retreat | Designer Finishes | Resort-Style Pool & Outdoor Living. Experience refined South Florida living in this fully renovated residence located in the heart of Palmetto Bay. Thoughtfully redesigned with a focus on modern elegance, comfort, and functionality, this home offers a seamless blend of indoor sophistication and outdoor lifestyle. From the moment you arrive, the property stands out with its clean architectural lines, updated exterior, and striking evening presence. Inside, expansive living areas flow effortlessly, enhanced by new flooring throughout, abundant natural light, and a warm contemporary aesthetic. The kitchen has been tastefully remodeled with modern finishes, sleek cabinetry, and an open layout ideal for both everyday living and entertaining. Multiple living areas provide flexibility for hosting, relaxing, and family life. The primary suite offers a private retreat with a fully updated bathroom featuring spa-inspired design and high-end finishes.The outdoor space is a true highlight. The covered terrace and screened pool enclosure create a private, resort-style setting, complemented by custom landscape lighting and mature greenery—perfect for both quiet evenings and entertaining guests.

16400 SW 80th Avenue, Palmetto Bay

$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

$899,000

4 Beds ⋅ 3 Baths ⋅ B26036022 MLS ⋅ The Oaks BLDG.

Welcome to The Oaks, one of Hobe Sound's premier gated communities. Nestled on a quiet cul-de-sac within the highly sought-after Estate Section, this spacious four-bedroom pool home offers exceptional privacy, a generous homesite, and serene preserve views. Step inside to soaring ceilings and an abundance of natural light that enhance the formal living and dining rooms. The spacious kitchen is equipped with 42-inch wood cabinetry, granite countertops, a center island, and newer stainless steel appliances. Rich wood flooring flows throughout the main living areas and continues upstairs, adding warmth and character throughout the home. Adding to the home's value and peace of mind, newly installed impact windows and doors provide enhanced storm protection, energy efficiency, and security. Upstairs, a versatile loft provides additional living space ideal for a media room, home office, or play area. All four bedrooms are located on the second level, including the oversized primary suite featuring dual walk-in closets and a spacious ensuite bath with separate vanities, a Roman soaking tub, and a walk-in shower. Additional features include a three-car garage and a fully fenced backyard. Residents of The Oaks enjoy a low HOA fee that includes lawn maintenance, Xfinity cable and high-speed internet, a community pool and spa, playground, and gated entry, offering both convenience and an exceptional lifestyle.

5536 SE Hammock Reserve Terrace, Hobe Sound

$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

$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

$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

$2,399,000

4 Beds ⋅ 4 Baths ⋅ A4671762 MLS

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/Nokomis

$789,000

3 Beds ⋅ 2 Baths ⋅ A4664085 MLS

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/Nokomis

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