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.

30 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $625,000

View 3008 Sea Plane Ln Kissimmee FL
View 3008 Sea Plane Ln Kissimmee FL
View 3008 Sea Plane Ln Kissimmee FL
Listed For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1539

  • Year Built

    2019

  • $/SqFt

    $406

Own Your Piece of Paradise Today! MLS#O5999107. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $620,000

View 3036 Sea Plane Ln Kissimmee FL
View 3036 Sea Plane Ln Kissimmee FL
View 3036 Sea Plane Ln Kissimmee FL
Listed For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1468

  • Year Built

    2019

  • $/SqFt

    $422

Come Claim Your Ticket to Parrotdise! MLS#O5999205. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $550,000

View 3013 Latitude Ln Kissimmee FL
View 3013 Latitude Ln Kissimmee FL
View 3013 Latitude Ln Kissimmee FL
Listed For 6 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1131

  • Year Built

    2019

  • $/SqFt

    $486

MINUTES FROM DISNEY PARKS! Time to Relax in Paradise! MLS#O5998849. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $550,000

View 8033 Dreamsicle Dr Kissimmee FL
View 8033 Dreamsicle Dr Kissimmee FL
View 8033 Dreamsicle Dr Kissimmee FL
Listed For 10 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1283

  • Year Built

    2019

  • $/SqFt

    $429

Margaritaville is More than a Community, it's a LIFESTYLE! MLS#O5994757. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $1,700,000

Listed For 18 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    3563

  • Year Built

    2020

  • $/SqFt

    $477

Low maintenance resort living includes fully maintained grounds, weekly pool maintenance, lawn care, and 24/7 roaming and manned gated security entrance. MLS#O5995917. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks Pended $1,600,000

Listed For 22 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3578

  • Year Built

    2020

  • $/SqFt

    $447

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. MLS#O5995298. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $620,000

Listed For 34 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2020

  • $/SqFt

    $440

AMAZING LOCATION MINUTES FROM DISNEY PARKS! Paradise Awaits! MLS#G5050118. CHARLES RUTENBERG REALTY ORLANDO.

Rolling Oaks For Sale $819,000

Listed For 39 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2021

  • $/SqFt

    $450

Furniture and Housewares Package for an ADDITIONAL $42k (NOT Included in List Price) MLS#O5992158. BHHS RESULTS REALTY.

Rolling Oaks For Sale $729,000

Listed For 39 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1539

  • Year Built

    2021

  • $/SqFt

    $474

**MARGARITAVILLE-APPROVED** FURNITURE PACKAGE AVAILABLE FOR AN ADDITIONAL 37K (not included in list price) MLS#O5992178. BHHS RESULTS REALTY.

Rolling Oaks Pended $600,000

Listed For 46 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1539

  • Year Built

    2019

  • $/SqFt

    $390

Start Enjoying Your Laid Back Paradise Today! MLS#O5991211. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $575,000

Listed For 54 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1306

  • Year Built

    2018

  • $/SqFt

    $440

Be Sure To Check Out Your Own Piece of Parrot-Dise! MLS#O5989403. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $769,000

Reduced By $6,000

Listed For 57 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2020

  • $/SqFt

    $416

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. MLS#O5989369. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $1,950,000

Listed For 60 Days
  • Bedrooms

    8

  • Full Bath(s)

    8

  • Sq. Ft.

    4131

  • Year Built

    2018

  • $/SqFt

    $472

There's Nothing Like Living the Margaritaville Lifestyle in Paradise! MLS#O5988786. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $2,499,500

Listed For 62 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4815

  • Year Built

    2018

  • $/SqFt

    $519

Margaritaville is only a half hour from Orlando International Airport. MLS#O5988368. COMMERCE BROKERAGE LLC.

Rolling Oaks For Sale $620,000

Listed For 69 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1384

  • Year Built

    2019

  • $/SqFt

    $448

Enjoy Your Very Own Slice of Parrotdise! MLS#O5986492. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $595,000

Listed For 77 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1384

  • Year Built

    2019

  • $/SqFt

    $430

AMAZING LOCATION MINUTES FROM DISNEY PARKS! Paradise Awaits! MLS#O5986028. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $550,000

Listed For 78 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1276

  • Year Built

    2019

  • $/SqFt

    $431

Come Enjoy the Margaritaville Lifestyle in Parrotdise! MLS#O5984231. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $825,000

Reduced By $15,000

Listed For 82 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2021

  • $/SqFt

    $446

Owner has a property rental contract with Ace Hospitality. MLS#O5984956. COMMERCE BROKERAGE LLC.

Rolling Oaks For Sale $609,000

Reduced By $20,900

Listed For 82 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $432

Unique First of its Kind Resort with Multiple Pools, Restaurants, Bars, Live Music, Gym, Kid's Club, On-Site Water Park, Retail and and More! MLS#O5982995. KELLER WILLIAMS RLTY,BREVARD.

Rolling Oaks Pended $525,000

Reduced By $25,000

Listed For 83 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $402

Owner has a property rental contract with Ace Hospitality. MLS#O5984691. COMMERCE BROKERAGE LLC.

Rolling Oaks For Sale $704,900

Reduced By $10,000

Listed For 94 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2052

  • Year Built

    2018

  • $/SqFt

    $344

The Resort is a short drive to the theme parks as well as many additional area attractions. Schedule your appointment today! MLS#S5058334. REUNION FLORIDA REALTY LLC.

Rolling Oaks For Sale $825,000

Reduced By $25,000

Listed For 113 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2250

  • Year Built

    2018

  • $/SqFt

    $367

Fitness center, live music, shopping, dining and entertainment ++ VERY CLOSE TO DISNEY. MLS#O5978488. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks For Sale $599,900

Listed For 128 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1131

  • Year Built

    2021

  • $/SqFt

    $530

Resort offer Multiple Pools, Restaurants, Bars, Gym, On-Site Water Park, Retail and free shuttle to Theme Parks. MLS#S5056492. FLORIDA FANTASY REAL ESTATE INC.

Rolling Oaks Pended $625,000

Listed For 129 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1539

  • Year Built

    2019

  • $/SqFt

    $406

Come Claim Your Piece of Paradise Today! MLS#O5974756. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $590,000

Listed For 129 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1384

  • Year Built

    2019

  • $/SqFt

    $426

The Time is Now to Live the Relaxing Margaritaville Lifestyle! MLS#O5974773. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $625,000

Listed For 151 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1539

  • Year Built

    2019

  • $/SqFt

    $406

Come Claim Your Piece of Paradise Today! MLS#O5968948. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $795,000

Reduced By $85,000

Listed For 152 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1848

  • Year Built

    2020

  • $/SqFt

    $430

The cottage can be rented out as an investment property or make it fabulous long-term living. MLS#O5966675. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks For Sale $749,000

Reduced By $1,000

Listed For 160 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2019

  • $/SqFt

    $363

This Home Is Fully Booked With Rental, Showing Is Not Easy MLS#O5967826. FLORIDA REALTY INVESTMENTS.

Rolling Oaks Pended $795,000

Reduced By $100,000

Listed For 163 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1848

  • Year Built

    2020

  • $/SqFt

    $430

The cottage can be rented out as an investment property or make it fabulous long-term living. MLS#O5966193. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks Pended $699,000

Reduced By $51,000

Listed For 173 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2020

  • $/SqFt

    $447

Margaritaville is minutes to Disney World, Sea Word and Universal Studios. MLS#O5964523. LUXE PROPERTIES LLC.

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Call to Schedule a Showing

(407) 477-6586

(407) 477-6586