The Oaks Homes for Sale

The Oaks Homes for Sale

Welcome to The Oaks, a picturesque subdivision nestled in the heart of Florida, where tranquility meets modern living. This charming community is designed for those who seek a serene lifestyle without sacrificing the conveniences of urban life. Surrounded by lush landscapes and vibrant greenery, The Oaks offers a perfect blend of natural beauty and contemporary amenities.

Homes for sale in The Oaks are nothing short of spectacular. Each residence boasts unique architectural styles, ranging from elegant single-family homes to spacious townhouses, ensuring that there’s something for everyone. With prices that cater to various budgets, prospective homeowners will find a diverse selection of properties equipped with modern features, open floor plans, and ample outdoor spaces perfect for entertaining or simply enjoying the Florida sunshine.

The community is well-equipped with top-notch amenities, including a sparkling swimming pool, well-maintained parks, and walking trails that encourage an active lifestyle. Families will appreciate the proximity to highly-rated schools, while shopping, dining, and entertainment options are just a short drive away.

Living in The Oaks means embracing a lifestyle of comfort and convenience. Whether you’re a first-time homebuyer looking for a cozy retreat or a growing family in search of more space, this subdivision has it all. Discover your dream home in The Oaks today, and experience the perfect harmony of community, nature, and modern living in beautiful Florida!

Newest The Oaks Homes for Sale

4 Beds ⋅ 4 Baths ⋅ B26072347 MLS ⋅ The Oaks BLDG.

Coastal-modern elegance meets lakefront luxury in this beautifully renovated 4-bedroom + bonus, 3.5-bath home in The Oaks. Set on a rare lot w/ serene lake views & a wide side yard, soaring ceilings crown the 3,262 sf living space, & a guest house w/ ensuite bath. The sumptuous kitchen w/ quartzite counters, custom cabinetry, an oversized contrasting island, & stainless appliances flows into a family room w/ elegant built-ins. The primary suite offers two outfitted walk-in closets & a spa bath with 48x48 porcelain tile & a jetted soaking tub; guest & half baths have also been refreshed, with wood-look flooring in every main bedroom. A new roof, retractable screens, a pool & spa, & hurricane protection complete the package. Welcome to The Oaks — a country-club lifestyle, without the equity. There's no place like The Oaks!! Featuring the widest variety and highest quality amenities, including clubhouse, restaurant and bar, finest racket programs and facilities for all levels and ages including world class tennis and pickleball, stellar fitness facility with a multitude of complimentary classes and instructors including Pilates, Spin, HIIT boot camps, water aerobics, Zumba, Yoga and so much more, Luxurious Spa with face and body treatments, wonderful special events for kids and adults alike, A-rated schools - the Oaks has something for everyone!!

17944 Villa Club Way, Boca Raton

6 Beds ⋅ 6 Baths ⋅ A4702047 MLS

A rare combination of timeless grandeur and effortless waterfront living, this bayfront estate in The Oaks Bayside commands approximately 150 feet of Bay frontage across 0.60 acres, with water views framing nearly every principal room. The residence offers 6 bedrooms, 5.5 baths, multiple covered balconies overlooking the Bay, additional ground-level flex space and a side-entry 3-car garage. A circular brick-paver driveway, tropical landscaping and a stately columned entrance create an unforgettable arrival. The dramatic two-story foyer features architectural columns, custom millwork and a wood-clad ceiling accent. European French white oak engineered flooring flows through the main living spaces. The living and family rooms feature soaring ceilings, extensive millwork, statement lighting, carved-stone fireplaces and oversized windows framing expansive water views. An adjoining sitting area features arched windows, a wood-clad ceiling and multiple glass doors opening to the waterfront balcony. The new kitchen is appointed with ceiling-height Shaker cabinetry, champagne-bronze hardware, marble countertops and an oversized waterfall island with seating for five. A GE Monogram appliance suite includes a professional gas range with griddle, refrigerator and dishwasher. A custom range hood, dimensional tile backsplash, apron-front sink and walk-in pantry complete the space. The waterfront dining nook incorporates built-in cabinetry, a stone serving counter and beverage cooler, while the formal dining room features a tray ceiling, paneled walls and columns. A waterfront office with built-in bookshelves, fireplace and balcony access, an updated laundry room and multiple en-suite guest accommodations complete the main level. Upstairs, the landing overlooks the living spaces beneath a crystal chandelier. The primary suite offers separate sleeping and sitting areas, a carved-stone fireplace, wide water views, private balcony access and two walk-in closets with custom storage. Its spa-inspired bath includes dual furniture-style vanities, a freestanding soaking tub beneath a picture window and an oversized frameless shower with marble-look tile, rainfall and handheld fixtures. Additional bedrooms offer en-suite or nearby baths, walk-in closets, abundant natural light and water or tropical views. Multiple covered balconies overlook the newly resurfaced pool, paver terrace, manicured lawn and waterfront. The pool features a 7-foot depth, entry steps, seating or sun-shelf areas, lighting, a self-cleaning system and a new pump. A private walkway through the mangroves leads to a new 5-by-60-foot composite dock completed in 2026, equipped with electric, water and a 6,000-pound boat lift. The property also features a concrete seawall and direct boating access. The lower level provides substantial additional flexibility for recreation, fitness, media or entertaining. Further updates include a newer 2023 tile roof, new HVAC, all-new appliances and flooring, new interior doors and moldings, hurricane protection and exterior lighting. The renowned Oaks Club is one of the area’s premier member-owned clubs, featuring two championship 18-hole golf courses, a full slate of tennis and fitness facilities, and an elegant clubhouse offering fine dining and a vibrant social calendar. Ideally situated in Osprey, the property offers convenient access to Gulf beaches, the Legacy Trail, dining and shopping, with downtown Sarasota and Venice both within easy reach.

112 Osprey Point Drive, Osprey/Nokomis

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

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

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

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

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

4 Beds ⋅ 3 Baths ⋅ A11998115 MLS

Fully Renovated Palmetto Bay Paradise/ Resort-Style Pool & Outdoor Living. *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. 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. Seller will contribute 1% of purchase price towards buyer's closing costs, contingent on offer terms.

16400 SW 80th Avenue, Palmetto Bay

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

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

Welcome to The Oaks, one of Hobe Sound's premier gated communities. Ideally positioned at the end of a quiet cul-de-sac in the highly sought-after Estate Section, this four-bedroom pool home is situated on one of the community's most EXPANSIVE and PRIVATE pie-shaped lots. Backing directly to a tranquil preserve with no rear neighbors, the exceptional homesite offers unmatched privacy, peaceful views, and a true sense of seclusion. Inside, soaring ceilings and abundant natural light enhance the formal living and dining areas. Newly installed IMPACT windows and doors provide valuable storm protection, improved energy efficiency, enhanced security, and added peace of mind. Rich hardwood flooring flows throughout the main living areas and continues upstairs, adding warmth and character. The expansive kitchen offers an abundance of 42-inch wood cabinetry, granite countertops, a center island, a wine/coffee bar area, and newer stainless steel appliances. The first floor also features a convenient cabana bathroom with direct pool access and a full-size laundry room with ample storage. The kitchen opens seamlessly to the family room, creating an inviting space ideal for entertaining, while impact-rated pocket sliders extend the living area outdoors to the pool and expansive backyard. The covered lanai is enhanced by retractable sunshades, while the exceptionally private backyard creates a peaceful outdoor oasis perfect for relaxing. 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 with his-and-hers walk-in closets and a spacious ensuite bath featuring separate vanities, a Roman soaking tub, and a walk-in shower. A beautifully remodeled secondary bathroom serves the additional bedrooms. Additional highlights include a three-car garage offering abundant storage 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

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

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

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