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 407-967-1435.

67 Results

Rolling Oaks Kissimmee Florida Homes For Sale

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 23 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

View 8053 Lost Shaker Ln Kissimmee FL
View 8053 Lost Shaker Ln Kissimmee FL
View 8053 Lost Shaker Ln Kissimmee FL
On Market For 44 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

View 8024 Surf St Kissimmee FL
View 8024 Surf St Kissimmee FL
View 8024 Surf St Kissimmee FL
On Market For 44 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

View 8036 Lost Shaker Ln Kissimmee FL
View 8036 Lost Shaker Ln Kissimmee FL
View 8036 Lost Shaker Ln Kissimmee FL
On Market For 45 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 $490,000

On Market For 45 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $412

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 50 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 53 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 55 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 For Sale $429,000

Reduced By $21,000

On Market For 59 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 62 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 $795,997

On Market For 74 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 $619,900

Reduced By $30,000

On Market For 81 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2019

  • $/SqFt

    $300

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

Rolling Oaks For Sale $640,000

Reduced By $9,900

On Market For 89 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 93 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 $525,000

Reduced By $10,000

On Market For 93 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $442

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 94 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 95 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 96 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 101 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 102 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 108 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $387

Don't wait any longer, come and own a piece of paradise today! MLS#O6207006. REAL BROKER, LLC.

Rolling Oaks For Sale $610,000

On Market For 110 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 114 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 115 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 130 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 132 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 141 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 144 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 154 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 $744,000

Reduced By $15,000

On Market For 154 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $360

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 154 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 $639,900

Reduced By $15,100

On Market For 185 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • 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#O6182570. EXP REALTY LLC.

Rolling Oaks For Sale $499,900

On Market For 191 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 $489,900

Reduced By $80,000

On Market For 193 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $285

MLS#O6181871. RE/MAX 200 REALTY.

Rolling Oaks For Sale $825,000

On Market For 196 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 194 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 206 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 199 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 189 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 208 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 216 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 219 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

*POTENTIAL GREAT VALUE
On Market For 220 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 $529,900

Reduced By $50,000

On Market For 225 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $339

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

Rolling Oaks For Sale $499,000

Reduced By $41,000

On Market For 234 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 265 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 269 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.

Rolling Oaks For Sale $799,900

Reduced By $40,100

On Market For 273 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 272 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 $515,000

Reduced By $35,000

On Market For 275 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $365

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

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