Laurel Oak Estates Homes with Gated Amenities

Laurel Oak Estates Homes with Gated Amenities

Welcome to Laurel Oak Estates, an exquisite gated community nestled in the heart of Sarasota County, Florida. This enchanting subdivision offers a perfect blend of luxury, privacy, and tranquility, making it an ideal haven for families, retirees, and anyone looking to embrace the Florida lifestyle.

Laurel Oak Estates boasts an impressive selection of beautifully designed homes, each crafted with meticulous attention to detail. From spacious single-family residences to elegant custom builds, there's a perfect fit for every discerning buyer. The homes are set against a backdrop of lush landscaping and serene water features, providing a picturesque setting that enhances the charm of this remarkable community.

One of the standout features of Laurel Oak Estates is its exclusive gated amenities. Residents enjoy peace of mind with 24/7 security, allowing for a safe and secure environment. The community also offers an array of recreational facilities, including a sparkling swimming pool, tennis courts, and walking trails that meander through the stunning natural surroundings. Whether you're looking to unwind with a leisurely stroll or engage in friendly competition on the courts, there's something for everyone.

Conveniently located just off I-75 East, Laurel Oak Estates provides easy access to the vibrant cultural scene of Sarasota, renowned beaches, and premier shopping and dining options. With its prime location and exceptional amenities, Laurel Oak Estates is not just a place to live; it's a lifestyle choice that promises comfort, luxury, and a true sense of community. Come discover the enchanting allure of Laurel Oak Estates, where your dream home awaits!

Newest Laurel Oak Estates Homes with Gated Amenities

2434 Dick Wilson Drive, Sarasota
$1,339,000
3 Beds ⋅ 3 Baths ⋅ Laurel Oak Estates SubDv. ⋅ 34240 Zip Code
Beautifully situated overlooking the 5th green of the Player Course in Laurel Oak Estates, this well-maintained three-bedroom, 2.5 bath home offers a wonderful combination of comfort & golf course living. The home features hardwood flooring in the main living areas & tile in the bathrooms. The inviting family room includes a gas fireplace, while the updated kitchen showcases attractive wood cabinetry. A spacious laundry center adds convenience, storage & a beverage cooler. A 3-car side entry garage with paver turnaround. Lawn maintenance is included in the quarterly HOA dues. Enjoy Florida living at its best in the expansive lanai, complete with a heated pool, spa & extended awning for added shade & comfort. Furnishings are available under separate agreement. Laurel Oak Country Club offers optional memberships featuring two championship golf courses, 12 Har-Tru tennis courts, a Jr. Olympic swimming pool, pickleball & an active social calendar. Enjoy an exceptional 42,000 sq ft clubhouse with formal & casual dining, complemented by outdoor seating with fire pits. Come Live the Lifestyle!

2434 Dick Wilson Drive, Sarasota
3321 Charles Macdonald Drive, Sarasota
$1,424,000
4 Beds ⋅ 5 Baths ⋅ Laurel Oak Estates SubDv. ⋅ 34240 Zip Code
Virtually Staged. In prestigious Laurel Oak Estates, this custom-built residence offers an exceptional setting overlooking the lake and fourth fairway of the Signature Jones golf course! A circular driveway welcomes you to this impressive four-bedroom, 4.5-bath home, featuring a bright, open plan with natural lighting. Kitchen features stainless steel appliances complemented by a wet bar and built-in desk. Additional features include a 3.5-car garage plus an air-conditioned storage/golf cart garage. On an oversized lot of approximately 0.493 acres, the home features an outdoor living area designed for entertaining with a large pool, spa, outdoor kitchen and awning for shade. Inside, a spacious laundry center with abundant storage adds everyday convenience. Laurel Oak Country Club offers two signature golf courses, 12 Har-Tru tennis courts, pickleball and an active social calendar. Experience the beauty, privacy and lifestyle that make Laurel Oak Estates desirable.

3321 Charles Macdonald Drive, Sarasota
3194 Charles Macdonald Drive, Sarasota
$1,699,000
4 Beds ⋅ 4 Baths ⋅ Laurel Oak Estates SubDv. ⋅ 34240 Zip Code
Set against an expansive backdrop of manicured fairways, this beautifully updated Arthur Rutenberg residence captures the space, privacy and indoor-outdoor lifestyle that make Laurel Oak Estates so desirable. Positioned on nearly half an acre with sweeping golf course views, the custom four-bedroom, four-bath home offers more than 3,800 square feet of single-level living, a three-car garage and a resort-inspired screened pool and spa. A circular pavered drive leads to double entry doors and a light-filled interior with high 12’ ceilings, architectural detailing and generous proportions. The thoughtful split-bedroom floor plan balances defined living and dining spaces with an open kitchen and family room designed for everyday comfort and entertaining. Built-in cabinetry and a wet bar enhance the living room, while abundant windows and sliding doors draw attention to the pool and golf course beyond. The kitchen was refreshed in 2025 with new quartz countertops, backsplash and lighting, complementing rich wood cabinetry, a substantial center island, breakfast bar and walk-in pantry. Premium appliances include Sub-Zero refrigeration, Wolf cooktop, two built-in Wolf ovens and a Miele dishwasher. The adjoining family room was renovated in 2024 with custom built-ins and luxury vinyl flooring, while a separate office with extensive built-in workspaces creates an ideal work-from-home setting. Privately positioned, the spacious primary bedroom features dual walk-in closets and a completely renovated 2025 en-suite bathroom with a freestanding soaking tub, dual vanities, quartz surfaces, walk-in shower and private water closet. Three additional bedrooms provide excellent flexibility, including two connected by a Jack-and-Jill bath and a private guest suite with an en-suite bath renovated in 2022 with quartz counters, new cabinetry and a zero-entry shower. Outside, the expansive screened lanai creates a private resort-like setting overlooking the Jones Course. Covered lounging and dining areas surround the saltwater pool and raised spa with waterfall feature, while a summer kitchen with granite countertops and bar seating makes entertaining effortless. The pool heater and glass blocks at the pool and spa were replaced in 2025. Additional improvements include two new Lennox HVAC systems in 2024, a 2017 tile roof, epoxy flooring and built-in cabinetry in the three-car garage, a 50-amp EV charging outlet and interior painting throughout most rooms in 2025. Laurel Oak Estates offers a gated setting with private roads and 24-hour guard service, with membership at Laurel Oak Country Club available separately. Conveniently located east of Downtown Sarasota, the community provides easy access to UTC, Lakewood Ranch, Waterside Place, Sarasota’s renowned dining, arts and cultural attractions, and the Gulf beaches of Siesta Key. Beautifully updated, exceptionally spacious and designed to embrace its golf-course setting, 3194 Charles MacDonald Drive offers a compelling combination of privacy, single-level living and resort-style outdoor space in the heart of Laurel Oak Estates.

3194 Charles Macdonald Drive, Sarasota
8250 Hugh Alison Place, Sarasota
$2,999,000
5 Beds ⋅ 5 Baths ⋅ Laurel Oak Estates SubDv. ⋅ 34240 Zip Code
“Five Fairways” Estate in Laurel Oak. Set on a serene cul-de-sac within the prestigious Laurel Oak Estates, this custom-built residence captures the essence of Sarasota’s coveted golf-course lifestyle. Poised on nearly an acre with sweeping fairway and lake views, the home offers more than 5,100 square feet of beautifully designed living space enhanced by timeless architectural detail, modern functionality, and effortless indoor-outdoor flow. A private winding drive and manicured landscaping introduce the stately façade, where double entry doors open to a grand foyer with high ceilings and walls of large windows that fill the interiors with natural light. The spacious living and dining areas feature custom built-ins and millwork, with expansive sliders framing sunset views of the sparkling pool and golf course beyond. Perfect for entertaining, the gourmet kitchen combines rich wood cabinetry with granite countertops, double ovens, built-in refrigerator, wet bar area, and casual dining nook overlooking the fairway. The adjoining family room offers a warm gathering space anchored by solid wood built-ins and a gas fireplace, with seamless access to the screened lanai for alfresco living. The primary suite is a secluded retreat with peaceful golf and water views, custom walk-in closet, private laundry, and a spa-inspired bath complete with soaking tub, separate shower, dual vanities, and private water closet. Three additional guest suites provide generous accommodations—two sharing a Jack-and-Jill layout, and one with a full en-suite bath—each thoughtfully designed for comfort and privacy. The theater room is equipped with platform seating, custom cabinetry, 120” screen, surround sound, remote-controlled lighting, and 4K projector. A true highlight of the home is the second-floor bonus suite, currently used as an art studio, featuring vaulted tongue-and-groove ceiling, built-in desks, a full bathroom, and an expansive balcony capturing unforgettable sunset vistas across the course. The screened outdoor living area defines the Florida lifestyle, showcasing a heated pool and spa, outdoor kitchen, and multiple seating areas for relaxing or entertaining. Mature landscaping, accent lighting, and the home’s ideal southwest exposure create a tranquil backdrop year-round. Additional features include plantation shutters, central vacuum, a three-car side-entry garage with golf-cart parking, and a whole-house solar system offering efficiency and peace of mind. Nestled behind the gates of Laurel Oak Country Club, residents enjoy access to 36 championship holes of golf, tennis and pickleball courts, a junior Olympic pool, fitness facilities, and a vibrant social calendar—all available with optional membership. Beyond the gates, you’re moments from Sarasota’s best amenities, including UTC Mall’s upscale shopping and dining, Nathan Benderson Park, and downtown Sarasota’s world-class arts, culture, and waterfront entertainment. Siesta Key and Lido Key beaches are within easy reach, completing the perfect blend of privacy, luxury, and convenience. With its exquisite craftsmanship, prime location, and inspiring golf-course vistas, this Laurel Oak Estates residence delivers the ideal balance of sophistication and relaxed Sarasota living—an exceptional opportunity for those seeking elegance within one of the region’s most prestigious gated communities.

8250 Hugh Alison Place, Sarasota
7767 Alister Mackenzie Drive, Sarasota
$1,650,000
4 Beds ⋅ 4 Baths ⋅ Laurel Oak Estates SubDv. ⋅ 34240 Zip Code
Back on the market after an interior refresh! Imagine mornings overlooking lush fairways, afternoons by your heated saltwater pool and spa, and evenings entertaining friends in your own private outdoor retreat. Set on over 2/3 of an acre along the 11th tee of the Jones Course, this exceptional 3,903-square-foot residence offers the space, privacy, and amenities to embrace the best of the Sarasota lifestyle. * Located in the guard-gated, golf cart-friendly community of Laurel Oak Estates, this thoughtfully designed one-story home features 4 bedrooms, 3.5 bathrooms, a dedicated office or home gym, soaring ceilings, 8-foot doors, and light-filled living spaces. The open floorplan balances effortless entertaining with comfortable everyday living, while the spacious primary suite offers two walk-in closets, plantation shutters, automated blackout shades, and a spa-inspired bath with soaking tub and bidet. Three additional bedrooms provide privacy and flexibility for family and guests. A private office or home gym with adjacent powder room ensure you can be productive while working your brains or your muscles from home. The well-appointed kitchen features quartz countertops, bar seating, and a breakfast nook overlooking the pool and lanai. There is tons of storage, with a handy in-kitchen pantry with slide-outs, plus a larger walk-in pantry to accommodate Costco runs and serve as an appliance garage. A central wet bar, two wine refrigerators (one for red, one for white), built-in speakers, wood-burning fireplace, clerestory windows, and wood floors create a welcoming setting for gatherings throughout the year. * Step outside to your private resort-style oasis, complete with a heated saltwater pool and spa, covered entertaining area, retractable awning, color-changing LED lighting, and outdoor grilling area. Expansive golf course views, a fenced yard on the side, and a backyard citrus cocktail tree add to the Florida lifestyle. * Peace of mind comes with IMPACT WINDOWS, new impact garage doors, hurricane curtains enclosing the lanai, and solar energy panels paired with a Tesla Powerwall for backup power and energy flexibility (can control your grid usage and also serves as a whole house generator). The 3 car garage has epoxy floors, an EV charger hook-up, and is insulated with a freestanding A/C to accommodate vehicles, gear, and even makes for a great setting for a golf simulator. * Laurel Oak Estates is renowned for its mature landscaping, natural preserves, and two championship golf courses. Residents can enjoy access to optional private club amenities, including golf, tennis, pickleball, swimming, dining, and social activities—**club membership is not required as it is in some other communities**. With guarded entry, patrolled security, NO CDD, and access to top-rated Sarasota-area schools, this is a rare opportunity to enjoy space, security, and an exceptional country club setting. **Discover the Laurel Oak lifestyle—schedule your private showing today.**

7767 Alister Mackenzie Drive, Sarasota
2528 Tom Morris Drive, Sarasota
$1,369,000
4 Beds ⋅ 3 Baths ⋅ Laurel Oak Estates SubDv. ⋅ 34240 Zip Code
Laurel Oak Estates, this premier golf course homesite, features an exceptional residence that offers breathtaking views and a resort-style pool and spa, creating the ideal setting for relaxing or entertaining. The spacious primary suite features hardwood flooring, a detailed tray ceiling, a bay window and two walk-in closets with built-in shelving. A luxurious bath with dual vanities, a soaking tub, double walk-in showers and a private garden wall. The well-appointed gourmet kitchen boasts granite countertops, abundant wood cabinetry, stainless steel appliances, a walk-in pantry, a compactor, extra 11-by-7 storage and a bright dinette with an aquarium window. Three distinctive themed guest rooms with hardwood flooring add charm and comfort. The gathering room has a gas fireplace and 11-foot sliders overlooking the pool area. Roof replaced (2020), ACs (2021). The garage is 3.5 spaces with a circular driveway. Located near shopping, churches, The Classical Academy and public schools. Located in the guard-gated Laurel Oak Estates, with optional Country Club memberships offering two championship golf courses, 12 Har-Tru tennis courts, pickleball, dining, a junior Olympic pool and an active social calendar. Live the Lifestyle!

2528 Tom Morris Drive, Sarasota
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