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.

24 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $629,000

View 3078 Pirate Way Kissimmee FL
View 3078 Pirate Way Kissimmee FL
View 3078 Pirate Way Kissimmee FL
On Market For 2 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2018

  • $/SqFt

    $402

Book your showing today before it's too late! MLS#O6098959. FLORIDA REALTY MARKETPLACE.

Rolling Oaks For Sale $650,000

View 3087 Pirate Way Kissimmee FL
View 3087 Pirate Way Kissimmee FL
View 3087 Pirate Way Kissimmee FL
On Market For 10 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $461

Start living the good life today! MLS#O6096219. HOMEVEST REALTY.

Rolling Oaks For Sale $1,650,000

View 8025 Surf St Kissimmee FL
View 8025 Surf St Kissimmee FL
View 8025 Surf St Kissimmee FL
On Market For 12 Days
  • Bedrooms

    7

  • Full Bath(s)

    7

  • Sq. Ft.

    4212

  • Year Built

    2019

  • $/SqFt

    $392

There's Nothing Like the Margaritaville Lifestyle! MLS#O6096561. REAL BROKER, LLC.

Rolling Oaks For Sale $1,050,000

View 8041 Surf St Kissimmee FL
View 8041 Surf St Kissimmee FL
View 8041 Surf St Kissimmee FL
On Market For 13 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2222

  • Year Built

    2019

  • $/SqFt

    $473

The Time is Now to Live the Margaritaville Lifestyle in Paradise! MLS#O6096288. EXP REALTY LLC.

Rolling Oaks Pended $895,000

On Market For 9 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1908

  • Year Built

    2021

  • $/SqFt

    $469

Purchase includes all appliances, furniture, washer, dryer and large screen TV's fully equipped ready to rent. MLS#O6095532. LUXE PROPERTIES LLC.

Rolling Oaks For Sale $650,000

On Market For 24 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $461

A perfect investment property for you and your family! MLS#O6094652. LA ROSA REALTY, LLC.

Rolling Oaks Pended $670,000

On Market For 15 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $324

There's Nothing Like the Margaritaville Lifestyle in Paradise! MLS#O6092089. EXP REALTY LLC.

Rolling Oaks For Sale $594,000

On Market For 36 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1048

  • Year Built

    2023

  • $/SqFt

    $567

See Realtor comments for information and showing instructions MLS#S5080925. P4L REALTY LLC.

Rolling Oaks For Sale $589,900

Reduced By $10,100

On Market For 37 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $497

CITY furniture package available for purchase! MLS#O6091024. REAL BROKER, LLC.

Rolling Oaks Pended $850,000

On Market For 17 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2020

  • $/SqFt

    $459

The Time is Now to Live the Margaritaville Lifestyle in Parrotdise! MLS#O6090703. EXP REALTY LLC.

Rolling Oaks For Sale $515,000

On Market For 40 Days
  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    660

  • Year Built

    2018

  • $/SqFt

    $780

Listing agent has interest in the ownership of the property. MLS#O6090695. XCELLENCE REALTY.

Rolling Oaks For Sale $825,000

Reduced By $25,000

On Market For 41 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1787

  • Year Built

    2020

  • $/SqFt

    $462

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. MLS#O6090197. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $719,800

On Market For 44 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2021

  • $/SqFt

    $606

The Time is Now to Live the Margaritaville Lifestyle in Parrotdise! MLS#O6087471. EXP REALTY LLC.

Rolling Oaks For Sale $765,000

On Market For 57 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2020

  • $/SqFt

    $489

There's Nothing Like the Margaritaville Lifestyle in Paradise! MLS#O6086467. EXP REALTY LLC.

Rolling Oaks For Sale $650,000

On Market For 71 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2018

  • $/SqFt

    $416

This home is ideal whether it is used as a primary residence, vacation home, or short-term vacation rental! MLS#O6082566. CORNERSTONE TRUST, LLC.

Rolling Oaks For Sale $640,000

Reduced By $5,000

On Market For 74 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $409

Come Claim Your Slice of Paradise! MLS#O6081646. EXP REALTY LLC.

Rolling Oaks For Sale $639,000

Reduced By $6,000

On Market For 82 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $409

Amazing Location Just Minutes From Disney Parks! MLS#O6075112. EXP REALTY LLC.

Rolling Oaks For Sale $2,200,000

On Market For 129 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4582

  • Year Built

    2019

  • $/SqFt

    $480

There's Nothing Like Living the Margaritaville Lifestyle in Paradise! MLS#O6071066. EXP REALTY LLC.

Rolling Oaks Pended $590,000

Reduced By $60,000

On Market For 132 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1724

  • Year Built

    2022

  • $/SqFt

    $342

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. MLS#O6067500. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks Pended $685,000

Reduced By $65,000

On Market For 131 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $370

Margaritaville has entertainment options, eat and drink at one of the four hotel restaurants and plenty more at the nearby Sunset Walk. MLS#O6065007. EXP REALTY LLC.

Rolling Oaks For Sale $2,175,000

Reduced By $100,000

On Market For 187 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4672

  • Year Built

    2021

  • $/SqFt

    $466

So, why wait schedule your showing today! MLS#S5073570. MCO REALTY.

Rolling Oaks For Sale $648,000

Reduced By $2,000

On Market For 187 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $414

Come Claim Your Ticket to Parrotdise! MLS#O6060785. EXP REALTY LLC.

Rolling Oaks For Sale $890,000

Reduced By $85,000

On Market For 249 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1787

  • Year Built

    2021

  • $/SqFt

    $498

Fitness center, live music, shopping, dining and entertainment, plus very close distance to Disney. MLS#O6042067. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks For Sale $789,000

Reduced By $90,000

On Market For 333 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1908

  • Year Built

    2019

  • $/SqFt

    $414

Your Relaxing Vacation Cottage Awaits Your Arrival! MLS#O6020566. KELLER WILLIAMS ADVANTAGE III REALTY.

  • 1

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-477-6586 and speak with one of our real estate consultants.

EasyStreet

Call to Schedule a Showing

(407) 477-6586

(407) 477-6586