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.

72 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $620,000

View 3136 Caribbean Soul Dr Kissimmee FL
View 3136 Caribbean Soul Dr Kissimmee FL
View 3136 Caribbean Soul Dr Kissimmee FL
On Market For 6 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

View 2920 Caribbean Soul Dr Kissimmee FL
View 2920 Caribbean Soul Dr Kissimmee FL
View 2920 Caribbean Soul Dr Kissimmee FL
On Market For 9 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

View 8001 Surf St Kissimmee FL
View 8001 Surf St Kissimmee FL
View 8001 Surf St Kissimmee FL
On Market For 21 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 $759,000

View 8001 Sand Bar Dr Kissimmee FL
View 8001 Sand Bar Dr Kissimmee FL
View 8001 Sand Bar Dr Kissimmee FL
On Market For 19 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $367

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

Rolling Oaks For Sale $540,000

On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $314

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 23 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 45 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 48 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 50 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 $420,000

Reduced By $40,000

On Market For 51 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $272

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 56 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 108 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 61 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 63 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 $469,900

Reduced By $10,000

On Market For 66 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $304

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 Pended $683,000

On Market For 60 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1908

  • Year Built

    2019

  • $/SqFt

    $358

Just minutes from Disney World, Universal Studios and all that Orlando has to offer. MLS#O6177031. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks For Sale $465,000

On Market For 73 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 $659,000

On Market For 72 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $356

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

Rolling Oaks For Sale $1,895,000

On Market For 73 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 $399,990

Reduced By $49,010

On Market For 74 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2023

  • $/SqFt

    $287

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 79 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 81 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 84 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 86 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 89 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 $559,900

Reduced By $20,000

On Market For 95 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $358

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 106 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 For Sale $429,000

Reduced By $100,000

On Market For 104 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • 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. Come schedule your showing today! MLS#O6170160. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $480,000

Reduced By $115,000

On Market For 112 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 $640,000

Reduced By $15,000

On Market For 115 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2052

  • Year Built

    2018

  • $/SqFt

    $312

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 119 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 135 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 $840,000

On Market For 138 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2021

  • $/SqFt

    $431

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 $530,000

Reduced By $20,000

On Market For 141 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 $375,000

Reduced By $394,000

*POTENTIAL GREAT VALUE
On Market For 144 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1787

  • Year Built

    2021

  • $/SqFt

    $210

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 Pended $663,900

Reduced By $1,100

On Market For 78 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $359

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care and 24/7 roaming security and gated access. MLS#O6162061. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $545,000

On Market For 144 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $418

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 151 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 $659,000

Reduced By $40,000

On Market For 157 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 157 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 157 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 For Sale $544,900

Reduced By $5,000

On Market For 169 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 171 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 $528,000

Reduced By $21,500

On Market For 175 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $342

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

Rolling Oaks For Sale $439,990

Reduced By $105,010

On Market For 197 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#O6149641. LOKATION.

Rolling Oaks For Sale $479,000

Reduced By $20,000

On Market For 199 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $344

Come Enjoy Your Very Own Slice of Paradise! MLS#O6147210. EXP REALTY LLC.

Rolling Oaks For Sale $879,000

Reduced By $50,000

On Market For 207 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1908

  • Year Built

    2021

  • $/SqFt

    $461

Purchase includes all appliances, furniture, washer, dryer and large screen TV's fully equipped ready to rent. MLS#O6146491. LUXE PROPERTIES LLC.

Rolling Oaks For Sale $899,000

Reduced By $21,000

On Market For 212 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1908

  • Year Built

    2020

  • $/SqFt

    $471

Your Relaxing Vacation Cottage Awaits Your Arrival! MLS#G5073745. SELLSTATE NEXT GENERATION REAL.

Rolling Oaks Pended $1,097,000

Reduced By $53,000

On Market For 195 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2632

  • Year Built

    2019

  • $/SqFt

    $417

Come Claim this Beautiful Properly as Your Own! MLS#O6143392. EXP REALTY LLC.

Rolling Oaks Pended $1,825,000

Reduced By $125,000

On Market For 194 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4092

  • Year Built

    2019

  • $/SqFt

    $446

Come Claims this Rare and Unique Properly as Your Own! MLS#O6139323. EXP REALTY LLC.

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