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.

75 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $799,990

View 8044 Shaker St Kissimmee FL
View 8044 Shaker St Kissimmee FL
View 8044 Shaker St Kissimmee FL
On Market For 5 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 $649,900

View 8193 Surf St Kissimmee FL
View 8193 Surf St Kissimmee FL
View 8193 Surf St Kissimmee FL
On Market For 5 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $378

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

Rolling Oaks For Sale $479,900

View 8103 Coconut Place Kissimmee FL
View 8103 Coconut Place Kissimmee FL
View 8103 Coconut Place Kissimmee FL
On Market For 6 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1742

  • Year Built

    2023

  • $/SqFt

    $275

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

Rolling Oaks Pended $1,097,000

View 8024 Shaker St Kissimmee FL
View 8024 Shaker St Kissimmee FL
View 8024 Shaker St Kissimmee FL
On Market For 14 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2632

  • Year Built

    2019

  • $/SqFt

    $417

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation. MLS#O6202666. EXP REALTY LLC.

Rolling Oaks For Sale $550,000

On Market For 21 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 $399,000

On Market For 23 Days
  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    775

  • Year Built

    2018

  • $/SqFt

    $515

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 32 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 35 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 45 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 $754,000

Reduced By $5,000

On Market For 45 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $365

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

Rolling Oaks For Sale $525,000

Reduced By $15,000

On Market For 45 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $305

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 49 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 $599,000

On Market For 71 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $425

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 For Sale $525,000

On Market For 73 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2023

  • $/SqFt

    $340

Seller Will Accept Btc And Eth MLS#S5101041. FLORIDA REALTY INVESTMENTS.

Rolling Oaks For Sale $655,000

On Market For 76 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 $410,000

Reduced By $50,000

On Market For 77 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $265

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 82 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 $569,900

On Market For 84 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $332

MLS#O6181871. RE/MAX 200 REALTY.

Rolling Oaks For Sale $825,000

On Market For 87 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 $399,000

Reduced By $46,000

On Market For 86 Days
  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    660

  • Year Built

    2018

  • $/SqFt

    $605

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

Rolling Oaks For Sale $419,000

Reduced By $60,900

On Market For 91 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $271

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#O6180287. EXP REALTY LLC.

Rolling Oaks For Sale $465,000

On Market For 97 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. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $645,000

Reduced By $14,000

On Market For 98 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $349

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

Rolling Oaks For Sale $1,895,000

On Market For 99 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 99 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. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $529,000

Reduced By $31,000

On Market For 104 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $308

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 107 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 110 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 112 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 113 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 $549,900

Reduced By $30,000

On Market For 116 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $352

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

Rolling Oaks For Sale $539,000

Reduced By $1,000

On Market For 125 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $413

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 Pended $399,000

Reduced By $130,000

On Market For 130 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $258

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. Come schedule your showing today! MLS#O6170160. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks Pended $480,000

Reduced By $115,000

On Market For 138 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1724

  • Year Built

    2022

  • $/SqFt

    $278

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. MLS#O6168094. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $637,000

Reduced By $18,000

On Market For 141 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2052

  • Year Built

    2018

  • $/SqFt

    $310

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#O6167136. EXP REALTY LLC.

Rolling Oaks For Sale $499,000

On Market For 145 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 $415,000

Reduced By $65,000

On Market For 160 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 $829,000

Reduced By $11,000

On Market For 164 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2021

  • $/SqFt

    $426

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 163 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.

Rolling Oaks For Sale $530,000

Reduced By $20,000

On Market For 166 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $376

Start living the good life today! MLS#O6162592. HOMEVEST REALTY.

Rolling Oaks For Sale $519,000

Reduced By $26,000

On Market For 170 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $398

Come Enjoy the Margaritaville Lifestyle in Paradise! MLS#O6154258. EXP REALTY LLC.

Rolling Oaks For Sale $459,000

Reduced By $15,000

On Market For 171 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $329

Don't miss the opportunity to own this villa in Margaritaville and start enjoying the resort lifestyle you and your family deserve today! MLS#O6160028. P4L REALTY LLC.

Rolling Oaks For Sale $397,500

Reduced By $127,500

On Market For 157 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $285

This townhome, reminiscent of the sophisticated charm of Key West, is available unfurnished but furnishings are negotiable. MLS#O6152914. LIFESTYLE INTERNATIONAL REALTY.

Rolling Oaks For Sale $659,000

Reduced By $40,000

On Market For 183 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $319

Come Claim Your Ticket to Parrotdise! MLS#O6157666. EXP REALTY LLC.

Rolling Oaks For Sale $525,000

On Market For 183 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1217

  • Year Built

    2018

  • $/SqFt

    $431

Come Claim Your Cottage in Paradise! MLS#O6158025. EXP REALTY LLC.

Rolling Oaks For Sale $439,990

Reduced By $105,010

On Market For 183 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $285

Furniture/Housewares Package included in list price. Don't Delay ! MLS#O6159203. LOKATION.

Rolling Oaks Pended $709,000

Reduced By $80,000

On Market For 179 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1787

  • Year Built

    2022

  • $/SqFt

    $397

Love every minute of it! Call Today! MLS#S5095093. CENTURY 21 CARIOTI.

Rolling Oaks For Sale $544,900

Reduced By $5,000

On Market For 195 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $386

Schedule your private tour today and envision yourself living the ultimate resort lifestyle in this enchanting 3-bedroom, 3-bathroom cottage home. MLS#O6155917. RE/MAX PRIME PROPERTIES.

Rolling Oaks For Sale $459,000

Reduced By $60,900

On Market For 193 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $297

This resort offers gym, heated large pool, free transportation to parks, tiki bars and restaurants. MLS#S5094572. NAIM REAL ESTATE LLC.

Rolling Oaks For Sale $498,000

Reduced By $51,500

On Market For 201 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $322

Come Claim You Ticket to Paradise! MLS#O6147570. EXP REALTY LLC.

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