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 5417.

75 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $795,997

View 8025 Sandy Toes Way Kissimmee FL
View 8025 Sandy Toes Way Kissimmee FL
View 8025 Sandy Toes Way Kissimmee FL
On Market For 11 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2020

  • $/SqFt

    $409

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

Rolling Oaks For Sale $625,000

View 3149 Caribbean Soul Dr Kissimmee FL
View 3149 Caribbean Soul Dr Kissimmee FL
View 3149 Caribbean Soul Dr Kissimmee FL
On Market For 16 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $364

Whether you're seeking a primary residence, vacation retreat, or lucrative investment opportunity, seize this exceptional lifestyle opportunity at Margaritaville Orlando! MLS#T3535897. HOMETRUST REALTY GROUP.

Rolling Oaks For Sale $649,900

View 8049 Lost Shaker Ln Kissimmee FL
View 8049 Lost Shaker Ln Kissimmee FL
View 8049 Lost Shaker Ln Kissimmee FL
On Market For 18 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2019

  • $/SqFt

    $315

HOA fee includes Internet and Cable TV. MLS#O6216224. COMPASS FLORIDA, LLC.

Rolling Oaks For Sale $649,900

View 2984 Salted Rim Rd Kissimmee FL
View 2984 Salted Rim Rd Kissimmee FL
View 2984 Salted Rim Rd Kissimmee FL
On Market For 26 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2019

  • $/SqFt

    $357

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 $455,000

On Market For 26 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $326

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#O6209191. EXP REALTY LLC.

Rolling Oaks For Sale $999,000

On Market For 30 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2222

  • Year Built

    2018

  • $/SqFt

    $450

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 $535,000

On Market For 30 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $450

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 31 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 32 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 33 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 $679,000

On Market For 37 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2019

  • $/SqFt

    $373

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6209229. EXP REALTY LLC.

Rolling Oaks For Sale $630,000

On Market For 38 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#O6209815. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks For Sale $560,000

On Market For 38 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $358

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 39 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 $460,000

On Market For 45 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $387

Rolling Oaks For Sale $610,000

On Market For 47 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $429

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 51 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 $594,500

Reduced By $55,400

On Market For 51 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $346

Live in the Margaritaville Resort Orlando! MLS#O6204517. COMMERCE BROKERAGE LLC.

Rolling Oaks For Sale $474,500

Reduced By $5,400

On Market For 52 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1742

  • Year Built

    2023

  • $/SqFt

    $272

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

Rolling Oaks For Sale $550,000

On Market For 67 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $390

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 69 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 78 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 81 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 $1,645,000

On Market For 91 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    3563

  • Year Built

    2019

  • $/SqFt

    $462

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 $469,000

Reduced By $71,000

On Market For 91 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $273

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.

Rolling Oaks For Sale $595,000

On Market For 95 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1724

  • Year Built

    2023

  • $/SqFt

    $345

Check out the 3D tour online and schedule a private viewing today! MLS#O6191345. REDFIN CORPORATION.

Rolling Oaks For Sale $589,000

Reduced By $10,000

On Market For 116 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $418

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6179345. EXP REALTY LLC.

Rolling Oaks Pended $415,000

Reduced By $110,000

On Market For 116 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2023

  • $/SqFt

    $269

Seller Will Accept Btc And Eth MLS#S5101041. LA ROSA REALTY KISSIMMEE.

Rolling Oaks For Sale $655,000

On Market For 122 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $317

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 122 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 128 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 $539,900

Reduced By $30,000

On Market For 130 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $314

MLS#O6181871. RE/MAX 200 REALTY.

Rolling Oaks For Sale $825,000

On Market For 133 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 132 Days
  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    660

  • Year Built

    2018

  • $/SqFt

    $598

Listing agent has interest in the ownership of the property. MLS#O6182018. XCELLENCE REALTY.

Rolling Oaks For Sale $465,000

On Market For 143 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 $635,000

Reduced By $24,000

On Market For 144 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $343

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

Rolling Oaks For Sale $1,895,000

On Market For 126 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 145 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 $459,000

Reduced By $101,000

On Market For 150 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $267

Don't miss out on the chance to make this your home or investment retreat – where every day feels like a holiday! MLS#S5099177. P4L REALTY LLC.

Rolling Oaks For Sale $830,000

On Market For 153 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 156 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 158 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 $600,000

Reduced By $45,000

On Market For 159 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $349

***MRO Approved City Furniture Package with Housewares for an additional $30k*** MLS#O6174168. WEATHERSPOON REALTY INC.

Rolling Oaks For Sale $539,900

Reduced By $40,000

On Market For 162 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $345

Contact me today for your private showing! MLS#O6174090. PREFERRED RE BROKERS III.

Rolling Oaks For Sale $499,000

Reduced By $41,000

On Market For 171 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 $499,000

On Market For 191 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $358

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#O6154819. EXP REALTY LLC.

Rolling Oaks For Sale $1,595,000

Reduced By $100,000

On Market For 202 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 $415,000

Reduced By $65,000

On Market For 206 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $298

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.

Rolling Oaks For Sale $799,900

Reduced By $40,100

On Market For 210 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2021

  • $/SqFt

    $411

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! MLS#O6162583. EXP REALTY LLC.

Rolling Oaks For Sale $649,000

Reduced By $120,000

On Market For 209 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1787

  • Year Built

    2021

  • $/SqFt

    $363

Don't miss the chance to own this slice of paradise in Margaritaville Resort—a dream home that seamlessly blends luxury, comfort, and the vibrant energy of one of the most sought-after vacation destinations. MLS#O6161909. FLORIDA PRESTIGIOUS HOMES INC.

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