Rolling Oaks Real Estate

Rolling Oaks Real Estate

Welcome to Rolling Oaks, a picturesque subdivision nestled in the heart of Florida, where charm and tranquility meet modern living. This enchanting community is designed for those seeking a serene lifestyle without sacrificing convenience. Rolling Oaks boasts beautifully landscaped streets, adorned with mature oak trees and vibrant gardens, creating a warm and inviting atmosphere for residents and visitors alike.

One of the standout features of Rolling Oaks is its prime location. Situated just a short drive from the bustling urban centers of Florida, residents enjoy easy access to shopping, dining, and entertainment options while still being able to retreat to their peaceful oasis at the end of the day. Families will appreciate the proximity to top-rated schools, parks, and recreational facilities, making it an ideal choice for those looking to settle down in a nurturing environment.

The homes in Rolling Oaks are a delightful blend of architectural styles, offering something for everyone. From charming single-family residences to spacious modern designs, each property reflects quality craftsmanship and attention to detail. Many homes feature expansive backyards, perfect for outdoor gatherings, gardening, or simply soaking up the sun.

Community spirit thrives in Rolling Oaks, with friendly neighbors and a variety of social events that foster connections and camaraderie. Whether you’re enjoying a leisurely stroll through the neighborhood or participating in community activities, you’ll find a welcoming atmosphere that makes you feel right at home.

Discover the beauty and charm of Rolling Oaks—your perfect slice of Florida paradise awaits!

Newest Listings in Rolling Oaks

$615,000
3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code
**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
$375,000
4 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 32712 Zip Code
Welcome to this charming and well-maintained home that offers the perfect blend of comfort, convenience, and Florida living. Featuring a spacious layout with bright, inviting living areas, this property is ideal for both everyday living and entertaining. The kitchen provides ample cabinet and counter space, while the generously sized bedrooms offer comfort and privacy. Step outside to enjoy the expansive yard, perfect for outdoor gatherings, gardening, or simply relaxing in the Florida sunshine. Conveniently located near shopping, dining, parks, major roadways, and local attractions, this home provides easy access to everything the area has to offer. Whether you're a first-time homebuyer, growing family, or investor, this property presents an excellent opportunity to enjoy a comfortable lifestyle in a desirable location. Don't miss your chance to make this wonderful home your own!

1335 Yvonne Street, Apopka
$415,000
3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34689 Zip Code
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 ⋅ Rolling Oaks SubDv. ⋅ 34689 Zip Code
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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