Below you can view all the homes for sale in the Rolling Oaks subdivision located in Kissimmee Florida. Listings in Rolling Oaks are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Rolling Oaks, give us a call at 407-477-6586.

65 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $445,000

View 3063 Pirate Way Kissimmee FL
View 3063 Pirate Way Kissimmee FL
View 3063 Pirate Way Kissimmee FL
On Market For 2 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1217

  • Year Built

    2018

  • $/SqFt

    $366

Just minutes from Disney and situated in Phase One of Margaritaville, this fully furnished home offers the flexibility to live full-time or participate in the rental program as much or as little as you desire. MLS#O6258593. LUXE PROPERTIES LLC.

Rolling Oaks For Sale $399,990

View 2957 Caribbean Soul Dr Kissimmee FL
View 2957 Caribbean Soul Dr Kissimmee FL
View 2957 Caribbean Soul Dr Kissimmee FL
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $259

** Photos Will Be Added Later This Week** MLS#O6258281. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $1,099,000

View 8020 Shaker St Kissimmee FL
View 8020 Shaker St Kissimmee FL
View 8020 Shaker St Kissimmee FL
On Market For 6 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    2632

  • Year Built

    2019

  • $/SqFt

    $418

LOCATED MINUTES FROM DISNEY PARKS. Come See This Beauty Today! MLS#O6257996. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $399,000

View 2968 On The Rocks Pt Kissimmee FL
View 2968 On The Rocks Pt Kissimmee FL
View 2968 On The Rocks Pt Kissimmee FL
On Market For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $258

This beautiful Villa is furnished through the City Furniture and Housewares Package (*included with purchase with Full Price Contract, and includes ALL the Furnishings and Accessories, Blinds, Drapes, TV's, Artwork, Kitchen Necessities, Dishes, Linens, and so much more...) Don't miss this opportunity - make your appointment to see this captivating Villa today and be in your new home before the holidays! MLS#L4948899. REMAX EXPERTS.

Rolling Oaks For Sale $520,000

On Market For 9 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $303

If you're looking for a permanent residence or a lucrative investment opportunity for short-term rentals, come on and take a look now! MLS#S5115348. LA ROSA REALTY KISSIMMEE.

Rolling Oaks For Sale $388,000

On Market For 30 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $251

Don’t miss out on owning a piece of paradise in Margaritaville! MLS#O6251417. LUXE PROPERTIES.

Rolling Oaks For Sale $405,000

On Market For 29 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $262

Furniture/Housewares Package Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! MLS#O6251477. DOUGLAS ELLIMAN.

Rolling Oaks For Sale $1,669,000

Reduced By $1,000

On Market For 47 Days
  • Bedrooms

    7

  • Full Bath(s)

    7

  • Sq. Ft.

    4212

  • Year Built

    2020

  • $/SqFt

    $396

Please schedule your private showing today! MLS#O6247697. REAL BROKER, LLC.

Rolling Oaks For Sale $479,000

On Market For 48 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $367

This Home Offers More Than Just A Place To Stay - it's A Lifestyle Of Resort-Style Living, Where Everyday Feels Like A Vacation. MLS#O6245812. EXP REALTY LLC.

Rolling Oaks For Sale $479,900

On Market For 49 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $404

If you choose to stay with the same rental company, there are reservations on the books for 2024 and 2025, Or if you want as your primary the bookings can be moved. Schedule a showing today! ! MLS#O6247045. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $645,000

On Market For 53 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1787

  • Year Built

    2022

  • $/SqFt

    $361

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6235033. EXP REALTY LLC.

Rolling Oaks For Sale $672,500

Reduced By $22,500

On Market For 61 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1787

  • Year Built

    2021

  • $/SqFt

    $376

This house isn't just a home – it's a lifestyle! MLS#O6243573. LUXE PROPERTIES LLC.

Rolling Oaks For Sale $529,000

Reduced By $20,000

On Market For 63 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2021

  • $/SqFt

    $445

Margaritaville Resort provides exclusive access to multiple pools, live music, fitness centers, on-site water parks, restaurants, and bars, giving you a slice of paradise right at your doorstep. MLS#O6243311. XCELLENCE REALTY INC..

Rolling Oaks For Sale $1,097,000

On Market For 70 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2222

  • Year Built

    2019

  • $/SqFt

    $494

The Time is Now to Live the Margaritaville Lifestyle in Paradise! MLS#O6240018. EXP REALTY LLC.

Rolling Oaks For Sale $754,000

Reduced By $15,000

On Market For 96 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2020

  • $/SqFt

    $408

Buyers and buyer agents are responsible for checking the accuracy of all measurements. MLS#O6231075. UNITED SHARES REAL ESTATE LLC.

Rolling Oaks For Sale $599,000

Reduced By $26,000

On Market For 118 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $324

Embrace the Margaritaville lifestyle in this exceptional property! MLS#O6226809. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $540,000

Reduced By $10,000

On Market For 118 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1283

  • Year Built

    2018

  • $/SqFt

    $421

Claim your piece of paradise today! MLS#O6227015. RE/MAX PRIME PROPERTIES.

Rolling Oaks For Sale $569,000

Reduced By $61,000

On Market For 118 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $404

Short-term rental allowed is what makes this place a great investment, secondary vacation cottage or primary home. MLS#O6226896. DOUGLAS ELLIMAN.

Rolling Oaks For Sale $459,000

Reduced By $31,000

On Market For 119 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $386

Just minutes from Disney World, Universal Studios, and all that Orlando has to offer, this home is the perfect choice for your next vacation or investment property. MLS#O6226832. DOUGLAS ELLIMAN.

Rolling Oaks For Sale $570,000

On Market For 127 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $404

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6224256. EXP REALTY LLC.

Rolling Oaks For Sale $549,000

Reduced By $50,000

On Market For 129 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $386

Secure your slice of paradise now! MLS#O6223170. LIFESTYLE INTERNATIONAL REALTY.

Rolling Oaks For Sale $649,000

Reduced By $26,000

On Market For 136 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1908

  • Year Built

    2019

  • $/SqFt

    $340

Live the Margaritaville lifestyle in paradise! MLS#O6221593. XCELLENCE REALTY INC..

Rolling Oaks For Sale $764,997

Reduced By $31,000

On Market For 148 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2020

  • $/SqFt

    $393

4 Beds and 4.5 Baths, FL 34747 MLS#T3536663. HOMECOIN.COM.

Rolling Oaks For Sale $640,000

Reduced By $9,900

On Market For 163 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2019

  • $/SqFt

    $352

This Home is Not Just a Residence or Vacation Home, It's a Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6213677. EXP REALTY LLC.

Rolling Oaks For Sale $549,900

Reduced By $15,100

On Market For 168 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $320

Call today to schedule a private tour. MLS#O6212229. CREEGAN GROUP.

Rolling Oaks For Sale $499,900

On Market For 169 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1550

  • Year Built

    2023

  • $/SqFt

    $323

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6211149. EXP REALTY LLC.

Rolling Oaks For Sale $459,000

On Market For 170 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $297

Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation. MLS#O6211062. EXP REALTY LLC.

Rolling Oaks For Sale $540,000

Reduced By $20,000

On Market For 175 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $345

This Home Is Not Just A Residence; It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation. MLS#O6209145. EXP REALTY LLC.

Rolling Oaks For Sale $650,000

On Market For 176 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $461

Come and Enjoy the Good Life in Margaritaville! MLS#O6208274. EXP REALTY LLC.

Rolling Oaks For Sale $436,990

Reduced By $23,010

On Market For 182 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $368

MLS#O6207006. REAL BROKER, LLC.

Rolling Oaks For Sale $519,000

Reduced By $91,000

On Market For 184 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $365

This Home Is Not Just A Residence; It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation. MLS#O6205101. EXP REALTY LLC.

Rolling Oaks For Sale $749,900

Reduced By $50,090

On Market For 188 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2018

  • $/SqFt

    $412

If you are in the market for a short-term rental, a vacation home, or full-time residence, this home offers your tropical escape and is the perfect choice for you! MLS#O6204595. COMMERCE BROKERAGE LLC.

Rolling Oaks Pended $425,000

Reduced By $54,900

*IS SHORT SALE
On Market For 189 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1742

  • Year Built

    2023

  • $/SqFt

    $244

Embrace the ultimate blend of relaxation, entertainment, and convenience in this spectacular villa. MLS#O6201330. EXP REALTY LLC.

Rolling Oaks For Sale $370,000

Reduced By $29,000

On Market For 206 Days
  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    775

  • Year Built

    2018

  • $/SqFt

    $477

Amazing Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation. MLS#O6200350. EXP REALTY LLC.

Rolling Oaks For Sale $620,000

On Market For 215 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1712

  • Year Built

    2023

  • $/SqFt

    $362

Schedule a private viewing to experience the unparalleled allure of this Key West style oasis. MLS#S5103228. WATSON REALTY CORP..

Rolling Oaks For Sale $580,000

On Market For 216 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $416

This Home Is Not Just a Residence; It's A Lifestyle Choice for Those Who Want to Experience the Best of Florida Living, Where Every Day Feels Like a Vacation. MLS#O6196674. EXP REALTY LLC.

Rolling Oaks For Sale $1,545,000

Reduced By $100,000

On Market For 228 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    3563

  • Year Built

    2019

  • $/SqFt

    $434

Don't miss your chance to own a piece of paradise in one of Orlando's most coveted destinations. MLS#O6194062. REAL BROKER, LLC.

Rolling Oaks For Sale $739,000

Reduced By $20,000

On Market For 222 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $358

It's 5 O' Clock Somewhere, so I've gotta run! MLS#O6193807. FLORIDA IN MOTION REALTY INC.

Rolling Oaks Pended $459,000

Reduced By $81,000

On Market For 227 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $267

Don't miss your chance to own a slice of paradise in Margaritaville Resort Orlando—contact us today to schedule a private viewing and start living the resort lifestyle you've always dreamed of. MLS#O6194090. XCELLENCE REALTY INC..

Rolling Oaks For Sale $597,000

Reduced By $58,000

On Market For 259 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $289

This Home Is Not Just A Residence; It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation. MLS#O6182570. EXP REALTY LLC.

Rolling Oaks For Sale $499,900

On Market For 265 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $324

Don't miss the chance to make this exquisite villa your own, where luxury meets leisure in the heart of Margaritaville. MLS#O6178763. LA JOLLA REALTORS.

Rolling Oaks For Sale $825,000

On Market For 270 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2021

  • $/SqFt

    $399

Whether you're looking for a short-term rental, long term rental, vacation home or full-time residence, this beautiful home is the perfect place to call your own! MLS#S5100094. LA ROSA REALTY KISSIMMEE.

Rolling Oaks For Sale $395,000

Reduced By $50,000

On Market For 268 Days
  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    660

  • Year Built

    2018

  • $/SqFt

    $598

Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened Sunset Walk, a 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new dine in movie theater. MLS#O6182018. XCELLENCE REALTY INC..

Rolling Oaks For Sale $465,000

On Market For 280 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2023

  • $/SqFt

    $334

Don't let your clients miss out on owning this Vacation Home! ! MLS#O6178541. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $1,895,000

On Market For 263 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4518

  • Year Built

    2019

  • $/SqFt

    $419

Perfect opportunity for a primary home, vacation home, or short-term rental. MLS#O6176550. THE REALTY MEDICS.

Rolling Oaks Pended $396,990

Reduced By $52,010

On Market For 281 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2023

  • $/SqFt

    $285

Margaritaville Resort Orlando is located just minutes away from Walt Disney World. MLS#O6178235. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $830,000

On Market For 290 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2021

  • $/SqFt

    $402

It's a Great Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living! MLS#O6174659. EXP REALTY LLC.

Rolling Oaks For Sale $735,000

On Market For 293 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2021

  • $/SqFt

    $521

It's A Great Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living! MLS#O6174627. EXP REALTY LLC.

Rolling Oaks For Sale $619,900

On Market For 295 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $361

Additionally, included in the list price is the MargaritaVille Approved City Furniture/Housewares Package, encompassing everything from blinds, drapes, and TVs to artwork, kitchen necessities, dishware, linens, and much more for your comfort. MLS#O6175033. LA JOLLA REALTORS.

Rolling Oaks For Sale $509,900

Reduced By $70,000

On Market For 299 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $326

Contact me today for your private showing! MLS#O6174090. DENIZ REALTY PARTNERS LLC.

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