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.

33 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $620,000

View 3000 Salted Rim Rd Kissimmee FL
View 3000 Salted Rim Rd Kissimmee FL
View 3000 Salted Rim Rd Kissimmee FL
Listed For 1 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1539

  • Year Built

    2019

  • $/SqFt

    $403

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

Rolling Oaks For Sale $590,000

View 3028 Salted Rim Rd Kissimmee FL
View 3028 Salted Rim Rd Kissimmee FL
View 3028 Salted Rim Rd Kissimmee FL
Listed For 1 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 $649,000

View 8092 Knee Deep Rd Kissimmee FL
View 8092 Knee Deep Rd Kissimmee FL
View 8092 Knee Deep Rd Kissimmee FL
Listed For 2 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1130

  • Year Built

    2020

  • $/SqFt

    $574

Amazing location minutes from Disney parks. MLS#O5973348. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks For Sale $745,000

View 2994 Salted Rim Rd Kissimmee FL
View 2994 Salted Rim Rd Kissimmee FL
View 2994 Salted Rim Rd Kissimmee FL
Listed For 3 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $403

Don't miss this chance, schedule a viewing now! MLS#O5973894. YOUR HOME SOLD GUARANTEED REALTY.

Rolling Oaks For Sale $590,000

Listed For 3 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1539

  • Year Built

    2019

  • $/SqFt

    $383

Come Claim Your Piece of Paradise Today! MLS#O5974043. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $620,000

Listed For 6 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1538

  • Year Built

    2018

  • $/SqFt

    $403

This home has never been rented and was used solely as a vacation home, so it is in pristine condition. MLS#O5973979. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks Pended $550,000

Listed For 7 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1296

  • Year Built

    2018

  • $/SqFt

    $424

Margaritaville Ethan Allen approved furniture not included in list price for an additional 25K MLS#O5973678. LUXE PROPERTIES LLC.

Rolling Oaks For Sale $599,000

Listed For 8 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2018

  • $/SqFt

    $383

With all of this AND MINUTES FROM THE THEME PARKS AND DISNEY you will know you are in paradise! MLS#O5973268. LUXE PROPERTIES LLC.

Rolling Oaks Pended $565,000

Listed For 8 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1131

  • Year Built

    2021

  • $/SqFt

    $500

The Time is Now to Experience the Resort Life and Enjoy Paradise! MLS#O5973300. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $1,495,000

Listed For 12 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4090

  • Year Built

    2019

  • $/SqFt

    $366

Come Claim Your Vacation Home in Paradise! MLS#O5971870. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $850,000

Listed For 12 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1908

  • Year Built

    2019

  • $/SqFt

    $445

Own Your Dream Home in Paradise! MLS#O5972367. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $490,000

Listed For 13 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1306

  • Year Built

    2018

  • $/SqFt

    $375

Come Enjoy the Margaritaville Lifestyle in Paradise! MLS#O5972427. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $810,000

Listed For 14 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2018

  • $/SqFt

    $446

Amazing Location Minutes From Disney Parks! MLS#O5970277. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $750,000

Listed For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1990

  • Year Built

    2021

  • $/SqFt

    $377

Start Living, Vacationing or Renting in One-of-a-Kind Beautiful Margaritaville! Come Enjoy Parrot-Dise! MLS#O5970021. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $850,000

Listed For 15 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1848

  • Year Built

    2021

  • $/SqFt

    $460

The cottage can be rented out as an investment property or make it fabulous long-term living. MLS#O5971291. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks For Sale $635,000

Listed For 20 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1421

  • Year Built

    2018

  • $/SqFt

    $447

Come Claim Your Ticket to Parrotdise! MLS#O5970476. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $625,000

Listed For 23 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 $880,000

Listed For 24 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1848

  • Year Built

    2020

  • $/SqFt

    $476

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 Pended $1,495,000

Listed For 28 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4480

  • Year Built

    2019

  • $/SqFt

    $334

Come Claim Your Vacation Home in Paradise! MLS#O5968827. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $725,000

Listed For 29 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $392

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. MLS#O5968619. PREFERRED REAL ESTATE BROKERS.

Rolling Oaks For Sale $749,000

Reduced By $1,000

Listed For 32 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2019

  • $/SqFt

    $363

The Community Offers A Lot Of Amenities,Surrounded By Great Dining. MLS#O5967826. FLORIDA REALTY INVESTMENTS.

Rolling Oaks For Sale $675,000

Reduced By $20,000

Listed For 35 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $479

With all of this AND MINUTES FROM THE THEME PARKS AND DISNEY you will know you are in paradise! MLS#O5967225. LUXE PROPERTIES LLC.

Rolling Oaks For Sale $657,800

Listed For 35 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2019

  • $/SqFt

    $338

Whether for a short-term rental investment opportunity or for personal use, this Key West style luxury vacation home in Margaritaville Resort Orlando will not only meet, but exceed your expectations! MLS#O5966876. REDFIN CORPORATION.

Rolling Oaks For Sale $750,000

Reduced By $30,000

Listed For 37 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2021

  • $/SqFt

    $413

It's Time for You to Enjoy your very own Slice of Parrotdise! MLS#O5966085. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $890,000

Listed For 38 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1848

  • Year Built

    2020

  • $/SqFt

    $482

The cottage can be rented out as an investment property or make it fabulous long-term living. MLS#O5966123. PREMIER SOTHEBY'S INTL. REALTY.

Rolling Oaks For Sale $615,000

Reduced By $15,000

Listed For 40 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1539

  • Year Built

    2018

  • $/SqFt

    $400

Come Relax in Paradise Living the Resort Life! MLS#O5966057. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $730,000

Reduced By $20,000

Listed For 45 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2020

  • $/SqFt

    $467

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

Rolling Oaks Pended $810,000

Listed For 47 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2018

  • $/SqFt

    $446

This cottage has been consistently performing extremely well in the rental program, but it can also be used as a second home or primary home for your own personal enjoyment. Your paradise awaits you. MLS#O5964164. PREMIER SOTHEBYS INT'L REALTY.

Rolling Oaks Pended $650,000

Listed For 48 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2018

  • $/SqFt

    $416

Come Claim Your Piece of Paradise Today! MLS#O5964028. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $615,000

Reduced By $5,000

Listed For 73 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2020

  • $/SqFt

    $436

Resort Style Community Unique First of its Kind Resort with Multiple Pools, Gym, Spa, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail, and More. LOCATED MINUTES FROM DISNEY PARKS. MLS#T3317424. HOMEWARD REAL ESTATE.

Rolling Oaks Pended $950,000

Listed For 74 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2511

  • Year Built

    2019

  • $/SqFt

    $378

Unique First of it's Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More. LOCATED MINUTES FROM DISNEY PARKS. MLS#O5957760. KELLER WILLIAMS REALTY CS.

Rolling Oaks For Sale $950,000

Reduced By $25,000

Listed For 96 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2511

  • Year Built

    2019

  • $/SqFt

    $378

Surf on Over to Your Slice of Paradise. MLS#O5951068. KELLER WILLIAMS REALTY CS.

Rolling Oaks Pended $580,000

Listed For 100 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1384

  • Year Built

    2018

  • $/SqFt

    $419

Property is Turn Key! Ride the Wave into Paradise! MLS#O5951382. KELLER WILLIAMS REALTY CS.

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Call to Schedule a Showing

(407) 477-6586

(407) 477-6586