Rolling Oaks Real Estate

Rolling Oaks Real Estate

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Florida, where the beauty of nature meets the comforts of modern living. This charming community is renowned for its lush landscapes, serene surroundings, and a friendly atmosphere that invites families and individuals alike to call it home.

Rolling Oaks boasts a variety of meticulously designed homes that cater to diverse lifestyles and preferences. From spacious single-family residences to cozy townhomes, each property is thoughtfully crafted with quality materials and contemporary finishes. Homeowners can enjoy expansive yards, perfect for outdoor gatherings, gardening, or simply soaking in the Florida sunshine.

One of the standout features of Rolling Oaks is its commitment to community and recreation. Residents have access to beautifully maintained parks, walking trails, and playgrounds, making it an ideal setting for families with children or anyone who enjoys an active lifestyle. The community also hosts regular events and gatherings, fostering a sense of camaraderie among neighbors.

Conveniently located, Rolling Oaks offers easy access to major highways, making commutes to nearby cities and attractions a breeze. Whether you're exploring the vibrant local dining scene, indulging in shopping at nearby boutiques, or taking a short drive to Florida's stunning beaches, everything you need is just moments away.

With its blend of natural beauty, welcoming community spirit, and convenient amenities, Rolling Oaks is more than just a subdivision; it’s a place where memories are made and cherished. Come and discover the charm of Rolling Oaks, where your dream home awaits!

Newest Listings in Rolling Oaks

$400,000
3 Beds ⋅ 2 Baths ⋅ O6429904 MLS
Welcome to 536 Bison Circle - this is an ideal home or rental property for those seeking an updated living space. This renovated home has 3 bedrooms with 2 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated luxurious bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2026, AC and Water Heater in 2025! This home also has a newly painted interior/exterior. Quiet Neighborhood, Close to all Major Highways, and Shopping Centers. Also an excellent rental investment opportunity.

536 Bison Circle, Apopka
$485,000
4 Beds ⋅ 2 Baths ⋅ O6428546 MLS
POOL HOME in Apopka – Move-In Ready! Enjoy your own private oasis with a screened-in pool, ideal for Florida living! This beautifully remodeled 4BR/2BA home features a NEW ROOF & AC (2026), new luxury vinyl flooring, and a gorgeous kitchen with quartz countertops. Spacious master suite, updated bathrooms, and fresh paint throughout. Prime location minutes from Kelly Park, Wekiva Springs, shopping & dining. Some pictures have been virtually staged to give the buyer an idea of how the home could look. Don't miss this one – schedule your showing today!

436 Bison Circle, Apopka
$615,000
3 Beds ⋅ 2 Baths ⋅ A12053754 MLS ⋅ Margaritaville BLDG.
**Rare waterfront cottage in Margaritaville Resort Orlando!** One of the few cottages with a premium direct waterfront location, this beautiful 3-bedroom, 2-bath home offers breathtaking water views from two private balconies.**Unlike heavily rented vacation homes, this residence has been privately enjoyed and carefully maintained**, giving it a like-new feel without the wear and tear often associated with short-term rentals. While never enrolled in a rental program, it is fully eligible for short-term rental, making it an excellent primary residence, vacation home, or investment opportunity.The home features tile flooring throughout, an open-concept floor plan, a durable metal roof, quartz countertops, stainless steel appliances, and beautifully designed living spaces with tasteful coastal décor. The spacious kitchen flows seamlessly into the living and dining areas, creating the perfect setting for entertaining.Enjoy peaceful water views, morning coffee, or spectacular Florida sunsets from either of the two private balconies.Margaritaville Resort Orlando offers resort-style amenities including multiple pools, a fitness center, Island H2O Water Park, shopping, dining, live entertainment, and the Promenade at Sunset Walk. Located just minutes from Walt Disney World and Orlando's major attractions, this rare waterfront property is an exceptional opportunity to own one of Margaritaville's most desirable cottages. **Rare waterfront cottage in Margaritaville Resort Orlando!** One of the few cottages in the community with a premium direct waterfront location, this beautiful 3-bedroom, 2-bath home offers breathtaking water views from both private balconies and a lifestyle unlike any other. **Unlike heavily rented vacation homes, this residence has been privately enjoyed and carefully maintained**, giving it a like-new feel without the wear and tear often associated with short-term rental properties. Whether you're looking for a primary residence, vacation home, or investment property, this home is eligible for short-term rentals and can easily be placed into the resort's rental program if desired. Inside, you'll find numerous upgrades, including tile flooring throughout, an open-concept floor plan, a durable metal roof, quartz countertops, stainless steel appliances, and beautifully designed living spaces that are both stylish and functional. The thoughtfully selected coastal décor perfectly complements the home's character and inviting atmosphere. The spacious kitchen opens seamlessly to the living and dining areas, creating the perfect space for entertaining family and friends. One of the home's most desirable features is its two private waterfront balconies—one on each level—where you can enjoy peaceful water views, your morning coffee, or spectacular Florida sunsets. Margaritaville Resort Orlando offers an exceptional resort lifestyle with multiple resort pools, a fitness center, live entertainment, shopping, dining, Island H2O Water Park, and the vibrant Promenade at Sunset Walk featuring restaurants, bars, boutiques, and year-round entertainment. Located just minutes from Walt Disney World and Orlando's other world-famous attractions, this rare waterfront property offers an outstanding opportunity as a primary residence, second home, or income-producing investment.

8117 Surf Street, Kissimmee
$615,000
3 Beds ⋅ 2 Baths ⋅ O6421843 MLS
**Rare waterfront cottage in Margaritaville Resort Orlando!** One of the few cottages in the community with a premium direct waterfront location, this beautiful 3-bedroom, 2-bath home offers breathtaking water views from both private balconies and a lifestyle unlike any other. **Unlike heavily rented vacation homes, this residence has been privately enjoyed and carefully maintained**, giving it a like-new feel without the wear and tear often associated with short-term rental properties. Whether you're looking for a primary residence, vacation home, or investment property, this home is eligible for short-term rentals and can easily be placed into the resort's rental program if desired. Inside, you'll find numerous upgrades, including tile flooring throughout, an open-concept floor plan, a durable metal roof, quartz countertops, stainless steel appliances, and beautifully designed living spaces that are both stylish and functional. The thoughtfully selected coastal décor perfectly complements the home's character and inviting atmosphere. The spacious kitchen opens seamlessly to the living and dining areas, creating the perfect space for entertaining family and friends. One of the home's most desirable features is its two private waterfront balconies—one on each level—where you can enjoy peaceful water views, your morning coffee, or spectacular Florida sunsets. Margaritaville Resort Orlando offers an exceptional resort lifestyle with multiple resort pools, a fitness center, live entertainment, shopping, dining, Island H2O Water Park, and the vibrant Promenade at Sunset Walk featuring restaurants, bars, boutiques, and year-round entertainment. Located just minutes from Walt Disney World and Orlando's other world-famous attractions, this rare waterfront property offers an outstanding opportunity as a primary residence, second home, or income-producing investment.

8117 Surf Street, Kissimmee
$2,700,000
4 Beds ⋅ 3 Baths ⋅ A12047272 MLS ⋅ Rolling Oaks BLDG.
Opportunity to live on this spectacular fenced-in corner lot parcel in Southwest Ranches. 4 bedroom + office, 3 bathroom estate offers the perfect blend of country living and modern comfort with a split floor-bedroom plan. Elegant spaces with formal living, dining and family rooms with large windows and French doors overlooking the backyard. Spacious kitchen features distressed white wood cabinetry, stainless steel appliances, wine cooler, granite counters, island, coffee-bar area, countertop seating and breakfast nook. Primary suite offers a spa-like bathroom with a jetted tub, double vanities, step in shower and walk-in closets. Impact glass, central vacuum system, Tesla EV charger and 2 car garage. Outside you will find an incredible outdoor living area featuring a covered patio, summer kitchen, refreshing pool and spa, and lush tropical landscaping designed for relaxing and entertaining. Beyond the backyard, the expansive grounds continue with a 6 stall horse barn, paddock riding area, chicken coop and plenty of room for horses and other farm animals. Whether you are an equestrian, hobby farmer or simply looking for privacy and open space, this exceptional property offers endless possibilities in one of South Florida's most renowned towns.

17710 SW 63rd Manor, Southwest Ranches
$1,250,000
A11903192 MLS
Prime residential land opportunity in the sought-after town of Southwest Ranches, FL. This corner lot, facing 178 Ave, offers a rare chance to build your dream home in a rapidly developing area. Surrounded by new, upscale residences, this property presents an ideal canvas for a custom-built home. The spacious lot provides ample room for a variety of architectural styles and outdoor amenities. Take advantage of this rare offering to create a personalized oasis in a thriving community

4800 SW 178 Avenue, Southwest Ranches
$375,000
3 Beds ⋅ 3 Baths ⋅ A11899936 MLS
Calling all investors: This unit is already generating income!! Turnkey, fully furnished 3BR/3 BA townhome in highly desirable Margaritaville Resort Orlando. Located just minutes from Disney, this property is already operating as a successful short-term rental with management in place or option to self-manage. Features include an open floor plan, 1 FULL BED & BATH on 1ST FLOOR, quartz countertops, tile flooring, and included linens, housewares, and decor. Resort amenities include multiple pools, fitness center, spa, restaurants, live music, water park, and free shuttles to theme parks. HOA covers cable, internet, landscaping, daily trash pickup, pest control, and 24/7 security. Ideal as an investment property, vacation home, or primary residence in one of Orlandos top resort communities. .

2971 Castaway Lane, Kissimmee
$395,000
3 Beds ⋅ 2 Baths ⋅ W7886211 MLS
Virtually Staged. Check out this Tarpon Springs stunner located on a gorgeous tree-lined street in the highly desirable Rolling Oaks community. This beautiful home features gorgeous tile flooring, soaring cathedral ceilings, and an inviting eat-in kitchen complete with a breakfast bar. The thoughtfully designed split-bedroom floor plan offers privacy and comfort, while the spacious primary suite boasts attractive laminate flooring and a walk-in closet. An inside utility room with additional storage adds convenience, and the tranquil screened porch overlooks a shady, fenced backyard, creating the perfect setting for relaxing or entertaining. Nestled in a quiet and established section of Tarpon Springs, Rolling Oaks offers a peaceful setting while remaining close to everything that makes the area so special. Enjoy easy access to the world-famous Tarpon Springs Sponge Docks, charming downtown Palm Harbor, Fred Howard Park, and the award-winning beaches of Honeymoon Island and Caladesi Island. This is Florida living at its finest—don't miss your opportunity to call this exceptional property home.

1672 Countrywood Street, Tarpon Springs
$429,900
4 Beds ⋅ 2 Baths ⋅ TB8488914 MLS
BUYERS-take advantage of a rare and valuable opportunity as this home has an ASSUMABLE LOAN at an incredibly low 3.25% interest rate! In today’s higher-rate environment, qualified buyers can potentially step into significant monthly savings and long-term financial benefits by assuming the seller’s existing mortgage. Opportunities like this are few and far between—don’t miss your chance! Welcome to this beautifully maintained 4-bedroom, 2-bathroom, 2-Car Garage home located in a sought-after neighborhood in Tarpon Springs—where homes rarely become available! Offering a spacious and inviting open floor plan, this residence is enhanced by soaring vaulted ceilings that create a bright, airy atmosphere perfect for both everyday living and entertaining. Step inside this lovely home and you’ll find beautiful wood-look tile flooring throughout the main living areas, combining style and durability, while the bedrooms offer easy-care laminate flooring for comfort and convenience. The kitchen is spacious with light cabinetry, stainless steel appliances, modern backsplash and breakfast bar. The Primary bedroom is located at the back of the home with ensuite bath, and access to the large screened rear porch. The primary bathroom has been tastefully updated with new faucets, toilet, shower fixtures, and a vent fan. The home features a split-floor plan which offers a hedge of privacy between the primary suite and the 3 additional guest bedrooms. The guest bathroom is beautiful with a large custom vanity with granite countertop, large decorative mirror and features newer shower fixtures with modern white tile in the shower/bath combo. Thoughtful updates throughout provide both comfort and peace of mind, including a 2018 roof, new Stainless-Steel appliances (2021), modern backsplash in kitchen (2025), a new hot water heater installed in 2023, updated smoke alarms throughout the home for added safety, while the living room and primary bedroom showcase newer ceiling fans for added comfort. Enjoy added confidence knowing this neighborhood experienced no flooding during the 2024 storms, and the home is located outside of the flood zone—meaning no flood insurance is required. With low HOA fees of just $150 per year, this property offers both value and peace of mind. Conveniently located near the iconic Tarpon Springs Sponge Docks, you’ll enjoy easy access to waterfront dining, shopping, and local culture. Love the beach? Sunset Beach and Fred Howard Park are just a short drive away! Plus, the home is zoned for excellent schools, making it an ideal choice for families and those looking to continue their education at nearby St. Pete College. This move-in ready home perfectly blends desirable updates, a rarely available location, and an exceptional layout—schedule your private showing today!

1640 Countrywood Street, Tarpon Springs
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