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 386-801-4854.

69 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $695,000

View 8133 Surf St Kissimmee FL
View 8133 Surf St Kissimmee FL
View 8133 Surf St Kissimmee FL
On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1787

  • Year Built

    2021

  • $/SqFt

    $389

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

Rolling Oaks For Sale $549,000

View 8027 Knee Deep Rd Kissimmee FL
View 8027 Knee Deep Rd Kissimmee FL
View 8027 Knee Deep Rd Kissimmee FL
On Market For 10 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2021

  • $/SqFt

    $462

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

View 8041 Surf St Kissimmee FL
View 8041 Surf St Kissimmee FL
View 8041 Surf St Kissimmee FL
On Market For 17 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 $769,000

View 8014 Knee Deep Rd Kissimmee FL
View 8014 Knee Deep Rd Kissimmee FL
View 8014 Knee Deep Rd Kissimmee FL
On Market For 44 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2020

  • $/SqFt

    $416

The resort also integrates convenience Multiple Pools, a Gym, an On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail, and More schedule your showing today! MLS#O6231075. UNITED SHARES REAL ESTATE LLC.

Rolling Oaks For Sale $599,000

Reduced By $26,000

On Market For 65 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 $550,000

On Market For 65 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1283

  • Year Built

    2018

  • $/SqFt

    $429

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

Rolling Oaks For Sale $630,000

On Market For 66 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $447

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 66 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 $1,198,000

On Market For 71 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    2632

  • Year Built

    2019

  • $/SqFt

    $455

LOCATED MINUTES FROM DISNEY PARKS. Come See This Beauty Today! MLS#O6223869. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $570,000

On Market For 74 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 $599,000

On Market For 76 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $421

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

Rolling Oaks Pended $429,000

Reduced By $21,000

On Market For 62 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $250

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6222062. EXP REALTY LLC.

Rolling Oaks For Sale $649,000

Reduced By $26,000

On Market For 83 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 $769,997

Reduced By $26,000

On Market For 95 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2020

  • $/SqFt

    $395

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 110 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 $974,899

Reduced By $24,101

On Market For 114 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2222

  • Year Built

    2018

  • $/SqFt

    $439

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming security. MLS#O6212606. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $479,000

Reduced By $56,000

On Market For 114 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $403

Schedule your tour asap to meet what life can bring you to! MLS#O6212212. SELECTA REALTY LLC.

Rolling Oaks For Sale $565,000

On Market For 115 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $329

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

Rolling Oaks For Sale $499,900

On Market For 116 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 117 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 122 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 123 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 $450,000

Reduced By $10,000

On Market For 129 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $379

Don’t miss the chance to own your own piece of paradise today! MLS#O6207006. REAL BROKER, LLC.

Rolling Oaks For Sale $597,000

Reduced By $13,000

On Market For 131 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $420

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 $799,990

On Market For 135 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2018

  • $/SqFt

    $440

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 For Sale $425,000

Reduced By $54,900

*IS SHORT SALE
On Market For 136 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 $505,000

Reduced By $45,000

On Market For 151 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $358

Just a short walk or free shuttle to Sunset Walk also offering multiple restaurants, shopping, bars, arcades, escape room, top golf simulator and sling shot ride. MLS#A4609118. KELLER WILLIAMS ON THE WATER S.

Rolling Oaks For Sale $370,000

Reduced By $29,000

On Market For 153 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 162 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 $569,000

On Market For 165 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $408

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 $1,595,000

Reduced By $50,000

On Market For 175 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    3563

  • Year Built

    2019

  • $/SqFt

    $448

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 169 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 For Sale $459,000

Reduced By $81,000

On Market For 175 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 206 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 $390,000

Reduced By $70,000

On Market For 203 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $252

Revel in the convenience of the Furniture/Housewares Package encompassing blinds, drapes, TVs, artwork, kitchen essentials, dishware, linens, and MORE! MLS#O6182450. KELLER WILLIAMS REALTY AT THE PARKS.

Rolling Oaks For Sale $499,900

On Market For 212 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 $484,900

Reduced By $85,000

On Market For 214 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $282

MLS#O6181871. RE/MAX 200 REALTY.

Rolling Oaks For Sale $825,000

On Market For 217 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 215 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 227 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 Pended $599,000

Reduced By $60,000

On Market For 214 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $324

Come Enjoy Your Very Own Slice of Paradise! MLS#O6167202. EXP REALTY LLC.

Rolling Oaks For Sale $1,895,000

On Market For 210 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 For Sale $396,990

Reduced By $52,010

On Market For 229 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 237 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 240 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 242 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 $519,900

Reduced By $60,000

On Market For 246 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $332

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

Rolling Oaks Pended $499,000

Reduced By $41,000

On Market For 254 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $382

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#O6171060. EXP REALTY LLC.

Rolling Oaks For Sale $1,595,000

Reduced By $100,000

On Market For 286 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    3563

  • Year Built

    2019

  • $/SqFt

    $448

It's a Lifestyle Choice For Those Who Want To Experience The Best of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6164922. EXP REALTY LLC.

Rolling Oaks For Sale $399,000

Reduced By $81,000

On Market For 290 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $286

A truly turnkey property that can be used as a vacation home, or as currently listed in the property management program. MLS#U8223912. RE/MAX ACTION FIRST OF FLORIDA.

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