The Oaks Homes with Pool

The Oaks Homes with Pool

Welcome to The Oaks, a serene and picturesque subdivision nestled in the heart of Florida, where luxury living meets nature’s beauty. This vibrant community is designed for those who appreciate the finer things in life, offering an idyllic setting for families, retirees, and everyone in between.

As you stroll through the tree-lined streets of The Oaks, you’ll be captivated by the stunning architecture and meticulously landscaped yards that define this neighborhood. The homes here are not just residences; they are a lifestyle choice, with many properties featuring private pools that invite you to relax and unwind under the warm Florida sun. Imagine hosting summer barbecues, enjoying evening swims, or simply soaking up the sun in your own backyard oasis.

The Oaks is more than just beautiful homes; it’s a community that fosters connection and camaraderie among its residents. With nearby parks, walking trails, and recreational facilities, you’ll find plenty of opportunities to enjoy the great outdoors. Families will appreciate the proximity to highly-rated schools, while shopping, dining, and entertainment options are just a short drive away.

For those seeking a tranquil yet vibrant lifestyle, The Oaks offers a perfect blend of comfort and convenience. Whether you’re looking to dive into a refreshing pool or take a leisurely stroll through the neighborhood, you’ll find that The Oaks is a place where memories are made and cherished. Come experience the charm of this beautiful subdivision and discover your dream home today!

Newest The Oaks Homes with Pool

$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
$114,900
2 Beds ⋅ 2 Baths ⋅ GC541198 MLS ⋅ 100 BLDG.
Fully updated 2 bed 2 bath in The Oaks. Great location near the University of Florida, Santa Fe College, and walking distance to North Florida Hospital. This second floor condo has every update imaginable. As you enter you are greeted with a large living room flowing to a screened patio with new tile flooring throughout. Both bedrooms are spacious, with plenty of closet space and room for a desk or additional seating. Bathrooms feature tile flooring and new vanities. Upgrades include new kitchen cabinets, wood countertops, flooring, freshly painted walls, trim, vanities, HVAC, and appliances. Community amenities include a pool, fitness center, and clubhouse. Perfect for primary residence or renting out while your son or daughter goes to school at UF or Santa Fe. Airbnb and short term rentals are allowed. Direct bus routes on Newberry Rd.

6519 W Newberry Road Unit 108, Gainesville
$1,595,000
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
$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
$99,000
2 Beds ⋅ 1 Baths ⋅ GC539890 MLS ⋅ 200 BLDG.
Attention Investors! Prime Location on Newberry Road Excellent opportunity in a highly desirable area—directly across from HCA Florida North Florida Hospital with easy access to I-75. Just a short walk to the Oaks Mall and minutes from restaurants, shopping, Santa Fe College, the University of Florida, and public transportation—making this an ideal rental property. Located in Building 200 on the first floor, this 2-bedroom, 1-bath unit features an open-concept floor plan, new refrigerator and stove, and in-unit laundry for added convenience and tenant appeal. The community offers great amenities, including a clubhouse, pool, fitness center, sidewalks, and ample open parking. Move-in ready with strong rental potential—an excellent addition to any portfolio!

6519 W Newberry Road Unit 204, Gainesville
$285,000
1 Beds ⋅ 1 Baths ⋅ A4690371 MLS ⋅ 51 BLDG.
This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is accessible by both elevator and stairs. Offered turn-key furnished, the unit includes a full kitchen equipped with a full-size refrigerator, combination oven/microwave, cooktop and dishwasher. The open concept living and bedroom area is complemented by a full bathroom with a walk-in shower. It has a beautiful foyer, luxury laminate flooring, and is clean and well-maintained. From your window, you can enjoy lovely views out over the pool, across to the lake. This is an incredible opportunity to own your personal sanctuary, perfect for weekend golfers, vacationing guests or weekend get-a-ways. And you will appreciate the flexible rental policy. Windsor Lodge Residents have their own private swimming pool and club house. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options.

51 Mac Ewen Drive Unit 14, Osprey/Nokomis
$235,000
1 Beds ⋅ 1 Baths ⋅ A4689838 MLS ⋅ Windsor Lodge BLDG.
Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey/Nokomis
Start Your Search