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 407-485-1814.

58 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $795,000

Scenic view of colorful homes with palm trees lining a waterfront property on a sunny day at 3020 Parrot Head Pl, Kissimmee, FL 34747
Inviting in-ground pool and spa with brick surround, metal fence and view of neighborhood homes at 3020 Parrot Head Pl, Kissimmee, FL 34747
Unique recreation room with tiki bar decor, bamboo accents, thatched roof, and a tropical ambiance at 3020 Parrot Head Pl, Kissimmee, FL 34747
On Market For 4 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2018

  • $/SqFt

    $437

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! EXP REALTY LLC.

Rolling Oaks For Sale $419,000

Charming townhouse with colorful facade, landscaped yard, and welcoming front entrance at 2920 On The Rocks Pt, Kissimmee, FL 34747
Townhouse exterior showcasing a charming facade, well-kept landscaping, and front entrance at 2920 On The Rocks Pt, Kissimmee, FL 34747
Inviting front entrance with stylish door, decorative address sign, and manicured landscaping at 2920 On The Rocks Pt, Kissimmee, FL 34747
On Market For 11 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $271

Don’t miss your chance to own a slice of paradise in one of Central Florida’s most sought-after resort communities. XCELLENCE REALTY INC..

Rolling Oaks For Sale $875,000

Outdoor patio featuring a small pool, table and chairs with a beautiful view of the community and the sky at 3036 Parrot Head Pl, Kissimmee, FL 34747
Relaxing outdoor pool at dusk, reflecting the ambient lighting and skyline in the water, with lounge chairs at 3036 Parrot Head Pl, Kissimmee, FL 34747
Charming two-story yellow beach home with light blue shutters, landscaped yard, and walkway to the front door at 3036 Parrot Head Pl, Kissimmee, FL 34747
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1787

  • Year Built

    2022

  • $/SqFt

    $490

Homes like this rarely come on the market—seize the opportunity to own a piece of paradise. XCELLENCE REALTY INC..

Rolling Oaks For Sale $479,000

Quaint peach-colored two-story home featuring blue shutters and a small balcony, nestled among lush greenery at 3062 Pirate Way, Kissimmee, FL 34747
Close-up of a peach-colored home showcasing a blue front door, shutters, and well-manicured landscaping at 3062 Pirate Way, Kissimmee, FL 34747
Open-concept living area featuring wood floors, stairs, stainless steel appliances and a dining area at 3062 Pirate Way, Kissimmee, FL 34747
On Market For 15 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $337

This tropical oasis awaits in Kissimmee at 3062 Pirate Way! LUXE PROPERTIES LLC.

Rolling Oaks Pended $350,000

Inviting two-story yellow home with a cute balcony, lush greenery, and a yellow chair on the porch at 3013 Latitude Ln, Kissimmee, FL 34747
Well-maintained gravel backyard with lush greenery, perfect for outdoor entertaining and relaxation with room to roam at 3013 Latitude Ln, Kissimmee, FL 34747
Backyard with a patio table, chairs, and tropical landscaping for outdoor relaxation and privacy at 3013 Latitude Ln, Kissimmee, FL 34747
On Market For 20 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $295

Please note: this home is not under contract with the hotel rental program but includes furniture in compliance with the hotel rental program. COLDWELL BANKER RESIDENTIAL RE.

Rolling Oaks For Sale $698,900

Relaxing pool area with lounge chairs, dining table, and colorful beach home views at 2938 Salted Rim Rd, Kissimmee, FL 34747
Sparkling pool with outdoor seating and lush green landscaping surrounded by colorful houses at 2938 Salted Rim Rd, Kissimmee, FL 34747
Refreshing pool area with comfortable lounge chairs and beautiful landscaping at 2938 Salted Rim Rd, Kissimmee, FL 34747
On Market For 23 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2021

  • $/SqFt

    $338

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! LA ROSA REALTY KISSIMMEE.

Rolling Oaks For Sale $589,000

Cozy peach colored house featuring double doors, fans and shutters at 8001 Sand Bar Dr, Kissimmee, FL 34747
Covered walkway showcasing columns and landscaping at 8001 Sand Bar Dr, Kissimmee, FL 34747
Peach home with a patio, table, and hot tub at 8001 Sand Bar Dr, Kissimmee, FL 34747
On Market For 22 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $285

It's 5 O' Clock Somewhere, so I've gotta run! FLORIDA IN MOTION REALTY INC.

Rolling Oaks For Sale $475,000

Open-concept living room and kitchen with modern appliances and stylish furnishings at 2988 Salted Rim Rd, Kissimmee, FL 34747
Bright kitchen features stainless steel appliances, white cabinetry, and adjacent dining area at 2988 Salted Rim Rd, Kissimmee, FL 34747
Cozy living room with a comfortable sofa and entertainment center, perfect for relaxing at 2988 Salted Rim Rd, Kissimmee, FL 34747
On Market For 28 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $304

Your relaxing, income-producing vacation cottage awaits! KELLER WILLIAMS ADVANTAGE III.

Rolling Oaks For Sale $680,000

Reduced By $10,000

Bright and airy two-story townhouse featuring a light grey paint scheme, balconies, and lush palm tree landscaping at 8044 Lost Shaker Ln, Kissimmee, FL 34747
Inviting front porch with blue door, white columns, and brick pavers, offering a warm welcome at 8044 Lost Shaker Ln, Kissimmee, FL 34747
Charming front porch featuring brick pavers, white columns, and a welcoming blue door with sidelight windows at 8044 Lost Shaker Ln, Kissimmee, FL 34747
On Market For 36 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2019

  • $/SqFt

    $329

Just minutes from Disney Parks and other major Orlando attractions, 8044 Lost Shaker Ln is a tropical dream come true, whether you live in it, rent it out, or both! SOUTHERN PRESTIGE REALTY INC.

Rolling Oaks Pended $424,900

Private backyard features a hot tub, patio table and chairs, and lounge chairs for relaxing at 8044 Dreamsicle Dr, Kissimmee, FL 34747
Bright living room with a white sofa, a glass coffee table, and views into the kitchen at 8044 Dreamsicle Dr, Kissimmee, FL 34747
Cozy living room features a mounted TV, white furniture, and lots of natural light at 8044 Dreamsicle Dr, Kissimmee, FL 34747
On Market For 44 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $358

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $379,000

Cozy living room with blue accent wall, modern furniture, ceiling fan, and adjacent dining area at 3192 Caribbean Soul Dr, Kissimmee, FL 34747
Inviting living room featuring a comfortable gray sofa, ceiling fan, and seamless flow to the dining area at 3192 Caribbean Soul Dr, Kissimmee, FL 34747
Open-concept living room with a stylish sofa, nearby kitchen with bar seating, and wood-look flooring at 3192 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 44 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1380

  • Year Built

    2023

  • $/SqFt

    $275

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. EXP REALTY LLC.

Rolling Oaks For Sale $950,000

Resort-style pool and spa with palm trees and picturesque lake views at 7968 Shaker St, Kissimmee, FL 34747
Private pool and spa with a patio area, perfect for outdoor relaxation and entertaining at 7968 Shaker St, Kissimmee, FL 34747
A two-story vacation home featuring a private pool, spa, and outdoor dining area at 7968 Shaker St, Kissimmee, FL 34747
On Market For 46 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2240

  • Year Built

    2018

  • $/SqFt

    $424

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! EXP REALTY LLC.

Rolling Oaks For Sale $420,000

Backyard patio with a table, chairs, and an umbrella, perfect for outdoor dining and relaxation at 3083 Key Lime Loop, Kissimmee, FL 34747
Relaxing hot tub on a brick patio surrounded by lush greenery, ideal for unwinding at 3083 Key Lime Loop, Kissimmee, FL 34747
Aerial view of a colorful community with well-maintained homes and landscaping at 3083 Key Lime Loop, Kissimmee, FL 34747
On Market For 50 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $322

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! EXP REALTY LLC.

Rolling Oaks For Sale $924,000

Reduced By $75,000

Relaxing community pool area with lounge chairs and picnic table surrounded by tropical palm trees at 7980 Shaker St, Kissimmee, FL 34747
Colorful row of homes with a waterfront view reflecting in the nearby pond at 7980 Shaker St, Kissimmee, FL 34747
Stunning aerial view of a colorful neighborhood, showcasing the community's serene ponds and waterways at 7980 Shaker St, Kissimmee, FL 34747
On Market For 51 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2250

  • Year Built

    2018

  • $/SqFt

    $411

This resort style community features two large swimming pools, multiple restaurants and bars, fitness center, full service spa, lush and tranquil walking trails to all ends of the community, as well as a moments walk to all of the restaurants, bars, shops and entertainment that Sunset Walk has Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming security. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $560,000

Colorful two-story coastal cottages with pastel exteriors, balconies, blue shutters, lush landscaping, and parking at 2978 Latitude Ln, Kissimmee, FL 34747
Cozy outdoor patio with brick pavers, seating, manicured garden, and tropical landscaping at 2978 Latitude Ln, Kissimmee, FL 34747
Open-concept living room and kitchen featuring a plush gray sectional sofa, wood-look tile flooring, and stainless appliances at 2978 Latitude Ln, Kissimmee, FL 34747
On Market For 54 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $397

This Property is the definition of Turn- Key! Welcome to Paradise! ! COLDWELL BANKER RESIDENTIAL RE.

Rolling Oaks For Sale $450,000

Relaxing backyard featuring a hot tub, lounge chair and lush tropical landscaping at 3009 Sea Plane Ln, Kissimmee, FL 34747
Cozy living room with comfortable seating, stylish decor, and seamless access to outdoor area at 3009 Sea Plane Ln, Kissimmee, FL 34747
Bright open-concept living area with modern furnishings, light-colored walls, and charming coastal decor at 3009 Sea Plane Ln, Kissimmee, FL 34747
On Market For 64 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1283

  • Year Built

    2018

  • $/SqFt

    $351

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! EXP REALTY LLC.

Rolling Oaks For Sale $459,000

Reduced By $31,000

Comfortable living room featuring a large sectional sofa, nautical decor, and lots of natural light at 2967 Latitude Ln, Kissimmee, FL 34747
Inviting living room with a cozy sectional sofa, entertainment center, and bright, cheerful decor at 2967 Latitude Ln, Kissimmee, FL 34747
Open-concept living and dining area with a comfortable sofa and well-equipped kitchen in the background at 2967 Latitude Ln, Kissimmee, FL 34747
On Market For 65 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $326

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! EXP REALTY LLC.

Rolling Oaks For Sale $399,990

Reduced By $88,010

Cozy living room with comfortable seating, stylish décor, and a mounted flatscreen TV for entertainment at 3205 Caribbean Soul Dr, Kissimmee, FL 34747
Comfortable living area with dining table, flatscreen TV, and stylish decor with wood look flooring at 3205 Caribbean Soul Dr, Kissimmee, FL 34747
Inviting bedroom with a plush queen bed, bedside table, and charming beach-themed decor at 3205 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 65 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1550

  • Year Built

    2023

  • $/SqFt

    $258

Don’t miss your chance to own a slice of paradise—schedule your showing today! PREFERRED REAL ESTATE BROKERS II.

Rolling Oaks For Sale $569,000

Reduced By $10,000

Backyard with Hot Tub surrounded by tropical landscaping and a patio dining area at 3083 Pirate Way, Kissimmee, FL 34747
Bright living room featuring a large sectional sofa, striped rug, and coastal-themed decor at 3083 Pirate Way, Kissimmee, FL 34747
Cozy dining area with gray cabinets, stainless steel appliances, and a rustic wooden table at 3083 Pirate Way, Kissimmee, FL 34747
On Market For 70 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $275

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. EXP REALTY LLC.

Rolling Oaks For Sale $379,000

Reduced By $20,000

Bright living space with wood-look flooring, a ceiling fan, and comfortable seating near the open kitchen at 8146 Coconut Pl, Kissimmee, FL 34747
Open-concept living and dining area featuring modern decor, wood-look floors, and ample natural light at 8146 Coconut Pl, Kissimmee, FL 34747
Cozy living room with modern decor, wood-look flooring, and a comfortable seating arrangement with a view at 8146 Coconut Pl, Kissimmee, FL 34747
On Market For 70 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2023

  • $/SqFt

    $272

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. EXP REALTY LLC.

Rolling Oaks For Sale $499,000

Reduced By $25,900

Inviting two-story home featuring a cheerful light blue exterior and lush landscaping at 8199 Coconut Pl, Kissimmee, FL 34747
Modern kitchen with white cabinetry, stainless steel appliances, and spacious island at 8199 Coconut Pl, Kissimmee, FL 34747
Bright dining area with white table, bench seating, and stylish decor at 8199 Coconut Pl, Kissimmee, FL 34747
On Market For 69 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1712

  • Year Built

    2023

  • $/SqFt

    $291

Don’t miss your chance to own a piece of paradise. Schedule your showing today! LIST-A-HOUSE REALTY, LLC.

Rolling Oaks For Sale $530,000

Reduced By $45,000

Close-up of a charming green home's entrance with landscaped garden, enhancing curb appeal at 8029 Sandy Toes Way, Kissimmee, FL 34747
Inviting living room with stylish furnishings, a modern TV, and tranquil decor accents at 8029 Sandy Toes Way, Kissimmee, FL 34747
Bright living room featuring modern decor, a comfortable sofa, and ample natural light at 8029 Sandy Toes Way, Kissimmee, FL 34747
On Market For 83 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2020

  • $/SqFt

    $446

Don’t miss your chance to experience the Margaritaville lifestyle. JMC REALTY.

Rolling Oaks For Sale $1,975,000

Bright open-concept kitchen and dining area with modern stainless steel appliances at 8165 Surf St, Kissimmee, FL 34747
Stylish kitchen island featuring stainless steel dishwasher and modern countertops at 8165 Surf St, Kissimmee, FL 34747
Comfortable living room with large sectional sofa and open access to the kitchen at 8165 Surf St, Kissimmee, FL 34747
On Market For 87 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4815

  • Year Built

    2021

  • $/SqFt

    $410

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

Rolling Oaks For Sale $528,500

Community pool and patio area surrounded by mature landscaping and colorful buildings at 8086 Knee Deep Rd, Kissimmee, FL 34747
Open living area featuring modern decor, white kitchen and lots of natural light at 8086 Knee Deep Rd, Kissimmee, FL 34747
View of an open living area with a staircase, white walls and comfortable furnishings at 8086 Knee Deep Rd, Kissimmee, FL 34747
On Market For 91 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2020

  • $/SqFt

    $445

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. EXP REALTY LLC.

Rolling Oaks For Sale $424,500

Inviting living room with bright colors, comfortable seating, a ceiling fan, and wood-look tile flooring at 8005 Flip Flop Way, Kissimmee, FL 34747
Comfortable open living space featuring wood-look tile flooring, modern decor, and abundant natural light at 8005 Flip Flop Way, Kissimmee, FL 34747
Spacious open concept living area with wood-look tile flooring, a ceiling fan, and bright, sunny yellow walls at 8005 Flip Flop Way, Kissimmee, FL 34747
On Market For 91 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $325

Come Enjoy the Margaritaville Lifestyle in Paradise! EXP REALTY LLC.

Rolling Oaks For Sale $449,900

Charming bedroom with twin beds, starry wallpaper, and decorative Mickey Mouse accents at 2929 Caribbean Soul Dr, Kissimmee, FL 34747
Charming bedroom featuring two twin beds, Mickey Mouse decor, and wood-look floors at 2929 Caribbean Soul Dr, Kissimmee, FL 34747
Bright, modern kitchen features a large island, stainless appliances, and plenty of cabinet space at 2929 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 99 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $291

Whether you plan to host vacationers, generate rental income, or enjoy it yourself, this property offers endless potential. NAIM REAL ESTATE LLC.

Rolling Oaks For Sale $549,900

Charming two-story home with modern design and colorful, tropical facade at 8179 Coconut Pl, Kissimmee, FL 34747
Street view of colorful modern townhomes with tropical landscaping at 8179 Coconut Pl, Kissimmee, FL 34747
Exterior of a two-story townhome, with light teal facade, walkway and landscaping at 8179 Coconut Pl, Kissimmee, FL 34747
On Market For 104 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $320

Call today to schedule a private tour. CREEGAN GROUP.

Rolling Oaks For Sale $485,000

Reduced By $10,000

Inviting community hot tub, with a view of colorful homes, manicured lawn and palm trees at 3020 Latitude Ln, Kissimmee, FL 34747
Bright and airy living room featuring hardwood floors, stylish sofas, dining table, and a well-equipped kitchen at 3020 Latitude Ln, Kissimmee, FL 34747
Cozy living room showcasing hardwood floors, stylish sofas, an airplane picture, and dining table next to kitchen at 3020 Latitude Ln, Kissimmee, FL 34747
On Market For 104 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $310

This Home Offers More Than Just A Place To Stay - it's A Lifestyle Of Resort-Style Living, Where Everyday Feels Like A Vacation. EXP REALTY LLC.

Rolling Oaks For Sale $455,000

Reduced By $45,000

Cozy living room featuring a sofa, chairs, coffee table, and a TV at 8059 Knee Deep Rd, Kissimmee, FL 34747
Open living space with a seating area, dining table, and kitchen area visible at 8059 Knee Deep Rd, Kissimmee, FL 34747
Open concept living and dining area with an adjacent kitchen at 8059 Knee Deep Rd, Kissimmee, FL 34747
On Market For 121 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $323

Don’t miss the chance to own a piece of paradise in this sought-after resort community! KELLER WILLIAMS ELITE PARTNERS III REALTY.

Rolling Oaks For Sale $1,950,000

Reduced By $25,000

Two-story light blue house with balcony, shutters, and walkway at 8153 Surf St, Kissimmee, FL 34747
Row of colorful houses with tile roofs and palm trees at 8153 Surf St, Kissimmee, FL 34747
Large community of colorful houses near a lake at 8153 Surf St, Kissimmee, FL 34747
On Market For 123 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4815

  • Year Built

    2020

  • $/SqFt

    $405

Your Perfect opportunity for a primary home, vacation home, or short-term rental. LOKATION.

Rolling Oaks Pended $340,000

Reduced By $10,000

Spacious lobby with comfortable seating and tropical decor at 2904 On The Rocks Pt, Kissimmee, FL 34747
Expansive resort-style pool area with ample seating, lush landscaping and adjacent lake views at 2904 On The Rocks Pt, Kissimmee, FL 34747
Row of colorful townhouses with parking at 2904 On The Rocks Pt, Kissimmee, FL 34747
On Market For 126 Days
  • Bedrooms

    2

  • Full Bath(s)

    3

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $244

As a Margaritaville guest, enjoy complimentary Disney transportation, world-class resort amenities, multiple pools, a state-of-the-art gym, and the vibrant Sunset Walk with restaurants, bars, live music, and shopping. KELLER WILLIAMS REALTY AT THE LAKES.

Rolling Oaks For Sale $1,499,000

Community pool with lounge chairs and lake view at 8137 Surf St, Kissimmee, FL 34747
Patio with table and chairs overlooking pool and lake at 8137 Surf St, Kissimmee, FL 34747
Back view of house, showcasing pool and patio at 8137 Surf St, Kissimmee, FL 34747
On Market For 136 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    3563

  • Year Built

    2020

  • $/SqFt

    $421

Low maintenance resort living includes fully maintained grounds, weekly pool maintenance, lawn care, and 24/7 roaming and manned gated security entrance. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $1,850,000

Two-story house with private pool, patio furniture, and hot tub at 3088 Parrot Head Pl, Kissimmee, FL 34747
Back view of two-story house with private pool, fenced yard, and landscaping at 3088 Parrot Head Pl, Kissimmee, FL 34747
Aerial view of community with lake, walkway, and residential buildings at 3088 Parrot Head Pl, Kissimmee, FL 34747
On Market For 139 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4092

  • Year Built

    2019

  • $/SqFt

    $452

The Time is Now to Start Living the Margaritaville Lifestyle! EXP REALTY LLC.

Rolling Oaks For Sale $845,000

Community pool and spa with surrounding landscaping at 8019 Knee Deep Rd, Kissimmee, FL 34747
Cozy living room with a sofa, TV, and accent pieces at 8019 Knee Deep Rd, Kissimmee, FL 34747
Cozy living room with a sofa, TV, and accent pieces at 8019 Knee Deep Rd, Kissimmee, FL 34747
On Market For 139 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    1908

  • Year Built

    2021

  • $/SqFt

    $443

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. EXP REALTY LLC.

Rolling Oaks For Sale $1,795,000

Reduced By $80,000

Private pool and spa with patio furniture and a grill at 3056 Parrot Head Pl, Kissimmee, FL 34747
Covered patio with dining table and chairs overlooking the pool at 3056 Parrot Head Pl, Kissimmee, FL 34747
Relaxing patio area with small table and chairs near the pool at 3056 Parrot Head Pl, Kissimmee, FL 34747
On Market For 161 Days
  • Bedrooms

    8

  • Full Bath(s)

    8

  • Sq. Ft.

    4335

  • Year Built

    2018

  • $/SqFt

    $414

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

Rolling Oaks For Sale $379,000

Reduced By $16,000

Row of colorful townhouses with palm trees and landscaping at 2956 Caribbean Soul Dr, Kissimmee, FL 34747
Front entryway with mint green door, bench, and lush landscaping at 2956 Caribbean Soul Dr, Kissimmee, FL 34747
Foyer with white kitchen cabinets, wood-look tile, and entryway decor at 2956 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 162 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $272

Schedule a viewing today and explore the wonderful possibilities of Margaritaville. FORTUNE INTERNATIONAL REALTY.

Rolling Oaks For Sale $1,095,000

Private backyard oasis with a refreshing pool and patio area at 8035 Surf St, Kissimmee, FL 34747
Covered balcony offering scenic views of the neighborhood at 8035 Surf St, Kissimmee, FL 34747
Outdoor patio with table, chairs, and a built-in sink at 8035 Surf St, Kissimmee, FL 34747
On Market For 167 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2222

  • Year Built

    2019

  • $/SqFt

    $493

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! EXP REALTY LLC.

Rolling Oaks Pended $529,000

Reduced By $10,000

Two-story townhome with light green exterior, landscaping, and walkway at 8135 Coconut Pl, Kissimmee, FL 34747
Open concept kitchen with island, stainless steel appliances, and dining area at 8135 Coconut Pl, Kissimmee, FL 34747
Modern kitchen with gray cabinets, quartz countertops, and stainless steel appliances at 8135 Coconut Pl, Kissimmee, FL 34747
On Market For 171 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1712

  • Year Built

    2023

  • $/SqFt

    $309

Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance. COLDWELL BANKER REALTY.

Rolling Oaks For Sale $515,000

Reduced By $10,000

Bright living room featuring a comfortable sectional sofa and a large flat-screen TV at 2972 Salted Rim Rd, Kissimmee, FL 34747
Spacious living area with sectional sofa, wood-look floors, and a stylish blue accent wall at 2972 Salted Rim Rd, Kissimmee, FL 34747
Open concept living space with gray kitchen cabinets, a sectional sofa, and a dining table at 2972 Salted Rim Rd, Kissimmee, FL 34747
On Market For 176 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $329

Don’t miss this opportunity to own a piece of paradise just minutes from the magic of Disney! SERHANT.

Rolling Oaks Pended $475,000

Reduced By $65,000

Community of colorful townhomes with a shared pool and lush landscaping at 2958 Castaway Ln, Kissimmee, FL 34747
Private patio with teal chairs and a view of the community at 2958 Castaway Ln, Kissimmee, FL 34747
Small patio with two teal chairs and a side table at 2958 Castaway Ln, Kissimmee, FL 34747
On Market For 177 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $276

Don’t miss this opportunity—schedule your private tour today! LIFESTYLE INTERNATIONAL REALTY.

Rolling Oaks For Sale $999,000

Reduced By $100,000

Private pool with spa and patio furniture at 8020 Shaker St, Kissimmee, FL 34747
Aerial view of three-story townhouses with private pools and lush landscaping at 8020 Shaker St, Kissimmee, FL 34747
Bright living room featuring a large sectional sofa and an open floor plan at 8020 Shaker St, Kissimmee, FL 34747
On Market For 194 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    2632

  • Year Built

    2019

  • $/SqFt

    $380

LOCATED MINUTES FROM DISNEY PARKS. Come See This Beauty Today! COLDWELL BANKER REALTY.

Rolling Oaks For Sale $479,000

Open living area with comfortable sofa, coffee table, and dining area at 3074 Key Lime Loop, Kissimmee, FL 34747
Living room with open concept floor plan and adjacent dining area at 3074 Key Lime Loop, Kissimmee, FL 34747
Living room with open concept floor plan and adjacent dining area at 3074 Key Lime Loop, Kissimmee, FL 34747
On Market For 237 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1305

  • Year Built

    2018

  • $/SqFt

    $367

This Home Offers More Than Just A Place To Stay - it's A Lifestyle Of Resort-Style Living, Where Everyday Feels Like A Vacation. EXP REALTY LLC.

Rolling Oaks For Sale $629,000

Reduced By $16,000

Lakefront community with sunset view and apartment buildings at 8125 Surf St, Kissimmee, FL 34747
Scenic lake view at sunset from a lakeside community at 8125 Surf St, Kissimmee, FL 34747
Community lake view at sunset with apartment buildings at 8125 Surf St, Kissimmee, FL 34747
On Market For 242 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1787

  • Year Built

    2022

  • $/SqFt

    $352

It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation! EXP REALTY LLC.

Rolling Oaks For Sale $499,000

Reduced By $51,000

Brick patio with seating area next to the house at 8024 Surf St, Kissimmee, FL 34747
Enjoy outdoor dining on the patio with table and chairs, surrounded by tropical landscaping at 8024 Surf St, Kissimmee, FL 34747
Charming two-story home with a patio and walkway, surrounded by lush landscaping at 8024 Surf St, Kissimmee, FL 34747
On Market For 231 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1283

  • Year Built

    2018

  • $/SqFt

    $389

Schedule your showing today and make this beautiful property your next great adventure. RE/MAX PRIME PROPERTIES.

Rolling Oaks For Sale $539,000

Reduced By $60,000

Two-story house with orange exterior, green accents, and palm trees at 8016 Flip Flop Way, Kissimmee, FL 34747
Two-story house with orange exterior, green accents, and palm trees at 8016 Flip Flop Way, Kissimmee, FL 34747
Two-story house with orange exterior, green accents, and palm trees at 8016 Flip Flop Way, Kissimmee, FL 34747
On Market For 318 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $379

Secure your slice of paradise now! LIFESTYLE INTERNATIONAL REALTY.

Rolling Oaks For Sale $629,900

Reduced By $20,000

Living room featuring two armchairs, a coffee table, and a large TV at 2984 Salted Rim Rd, Kissimmee, FL 34747
Bright living room with gray sofas, a large TV, and French doors at 2984 Salted Rim Rd, Kissimmee, FL 34747
Modern kitchen featuring stainless steel appliances and a large island at 2984 Salted Rim Rd, Kissimmee, FL 34747
On Market For 352 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2019

  • $/SqFt

    $346

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! EXP REALTY LLC.

Rolling Oaks For Sale $540,000

Reduced By $20,000

Cozy living room with sectional sofa and nautical decor at 8080 Dreamsicle Dr, Kissimmee, FL 34747
Living room with sectional sofa, TV, and decorative accents at 8080 Dreamsicle Dr, Kissimmee, FL 34747
Open floor plan with dining table, living area, and kitchen at 8080 Dreamsicle Dr, Kissimmee, FL 34747
On Market For 364 Days
  • Bedrooms

    4

  • 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. EXP REALTY LLC.

Rolling Oaks For Sale $399,000

Reduced By $61,000

Pink two-story home with balcony and landscaping at 2956 Salted Rim Rd, Kissimmee, FL 34747
Aerial view showcasing a community of colorful, two-story homes at 2956 Salted Rim Rd, Kissimmee, FL 34747
Open living area with kitchen, featuring a comfortable couch and dining area at 2956 Salted Rim Rd, Kissimmee, FL 34747
On Market For 371 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $336

REAL BROKER, LLC.

Rolling Oaks Pended $734,990

Reduced By $65,000

Private balcony overlooking a canal and neighboring houses at 8044 Shaker St, Kissimmee, FL 34747
Balcony with yellow door and view of neighboring homes at 8044 Shaker St, Kissimmee, FL 34747
Refreshing community pool with lounge chairs and patio furniture at 8044 Shaker St, Kissimmee, FL 34747
On Market For 374 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2018

  • $/SqFt

    $404

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! COMMERCE BROKERAGE LLC.

Rolling Oaks For Sale $430,000

Reduced By $49,900

View of pastel townhome with landscaping at 8103 Coconut Place, Kissimmee, FL 34747
Private patio with teal chairs and small table at 8103 Coconut Place, Kissimmee, FL 34747
Small patio with teal adirondack chairs at 8103 Coconut Place, Kissimmee, FL 34747
On Market For 187 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1742

  • Year Built

    2023

  • $/SqFt

    $247

Embrace the ultimate blend of relaxation, entertainment, and convenience in this spectacular villa. EXP REALTY LLC.

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Call to Schedule a Showing

(407) 485-1814

(407) 485-1814