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 ⋅ 3 Baths ⋅ B26077144 MLS ⋅ The Oaks BLDG.

Rarely available Laguna model in the prestigious Oaks of Hobe Sound. This 4 bed 2.5 bath pool home has a newly updated kitchen, bathrooms, flooring, and A/C! Offering a open-concept layout ideal for entertaining. Oversized kitchen features 42" wood cabinetry, stainless steel appliances, granite countertops, and a large walk-in pantry. It flows into the dining area and family room. A powder bath and laundry room are located on the first floor. Outdoors, a private pool is framed by an extra-tall screened enclosure for year-round enjoyment. Upstairs has an oversized loft ideal for a media room, game room, or additional living space. The primary suite includes dual vanities, walk-in shower, soaking tub, and large his/hers closets. Close to beaches and in a A-rated school district.

5935 SE Crooked Oak Avenue, Hobe Sound

3 Beds ⋅ 3 Baths ⋅ A4705716 MLS

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/Nokomis

4 Beds ⋅ 4 Baths ⋅ A4705572 MLS

Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with a workspace, overhead storage, and cabinets. Ideally positioned as the closest residence to the clubhouse on MacEwen, the home overlooks the 2nd and 3rd holes of the Eagle Course. Manicured landscaping offers complete privacy. Beyond are breathtaking golf course and lake views. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. The renovated kitchen opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus a formal dining room and breakfast bar for flexible entertaining. This exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership

362 Macewen 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

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.

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 luxury residence is privately positioned on an expansive double lot at the end of a quiet cul-de-sac in Bishops Court, an intimate gated enclave within The Oaks Preserve in Osprey, Florida. Framed by lush conservation views and a canopy of mature oaks, the property blends classic architectural character with thoughtfully curated updates in one of the Sarasota area’s most prestigious private country club communities. Professional lawn care and irrigation are included in the monthly fees. The residence offers three bedrooms, three-and-a-half baths, multiple indoor and outdoor gathering spaces, and a seamless connection to its tranquil natural surroundings. 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 areas, while the dining room’s built-in serving bar and wine chiller complement the beautifully updated kitchen. Custom white cabinetry, granite countertops, stainless steel appliances, an oversized island, and curated designer lighting define the space. A Sonos sound system extends throughout the residence. The primary suite is a private retreat featuring vaulted ceilings, a bay-window sitting area, outdoor access, and a fully renovated, spa-inspired bathroom 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. The additional bathrooms have also been extensively renovated with elevated finishes and designer fixtures. In the laundry room, custom storage, shiplap detailing, and functional built-ins boast a refined aesthetic. Upstairs, a spacious bonus room, freshly painted in 2026, features a fireplace and opens directly to a newly renovated second-story deck overlooking the treetops. Complete with a full bathroom, this highly versatile level can serve as private guest accommodations, a recreation or media room, home office, art studio, creative retreat, or secluded lounge. Outdoor living is equally compelling, centered around a seven-foot-deep heated pool and spa surrounded by brick pavers, tropical landscaping, and peaceful 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; 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. The Oaks offers an exceptional club-centered lifestyle just south of Sarasota, with two championship golf courses, Har-Tru tennis courts, pickleball, croquet, a state-of-the-art fitness center, fine and casual dining, and an active year-round social calendar. Golf or Social Membership is required with homeownership. The Oaks Club has earned recognition as a Platinum Club of America, a Distinguished Emerald Residential Country Club, and an Audubon International Certified property, reinforcing its standing as a premier private residential club. The Oaks delivers an exceptional lifestyle in Osprey between Sarasota and Venice. Gulf Coast beaches, boating, the Legacy Trail, Oscar Scherer State Park, Pine View School, downtown Sarasota, and historic Venice are all within easy reach.

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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