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 407 718 3706.

61 Results

Rolling Oaks Kissimmee Florida Homes For Sale

Rolling Oaks For Sale $589,000

Cozy living room with gray sofa, wood floors, and an open floorplan to kitchen and dining at 3095 Key Lime Loop, Kissimmee, FL 34747
Open-concept living room and kitchen with modern furnishings and a large flatscreen TV at 3095 Key Lime Loop, Kissimmee, FL 34747
Inviting living room with blue accent wall, stylish decor, and ample natural light at 3095 Key Lime Loop, Kissimmee, FL 34747
On Market For 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2018

  • $/SqFt

    $302

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 $579,000

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 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2018

  • $/SqFt

    $280

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

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 4 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2023

  • $/SqFt

    $286

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 $524,900

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 4 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1712

  • Year Built

    2023

  • $/SqFt

    $307

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

Rolling Oaks For Sale $575,000

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 17 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2020

  • $/SqFt

    $484

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

Rolling Oaks Pended $395,000

Close-up of a Caribbean Dream home's entrance, showcasing the vibrant colors and lush landscaping at 2925 Caribbean Soul Dr, Kissimmee, FL 34747
Charming street view of colorful Caribbean Dream homes with lush landscaping and ample parking at 2925 Caribbean Soul Dr, Kissimmee, FL 34747
Modern living room with stylish furnishings, including a comfortable sofa, round dining table, and decor at 2925 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $256

Don't miss this rare opportunity to own a tropical retreat in one of Central Florida’s most iconic resort communities. Schedule your private tour today! REAL BROKER, LLC.

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 21 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 25 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 25 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 $349,999

View of colorful townhomes with lush palm trees, vibrant paint, and neatly striped parking spaces at 2927 Castaway Ln, Kissimmee, FL 34747
Street view showcasing colorful townhomes with parking spaces, trees, and vibrant architectural details at 2927 Castaway Ln, Kissimmee, FL 34747
Townhomes with vibrant colors, well-maintained landscaping, and inviting architectural details at 2927 Castaway Ln, Kissimmee, FL 34747
On Market For 31 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $251

Don’t wait schedule your tour today and make this dream villa yours! BAIRD 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 33 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 38 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 $495,000

Charming tan home with blue trim, a landscaped yard, a sidewalk, and a sign for accessible parking spaces at 3020 Latitude Ln, Kissimmee, FL 34747
A hot tub in a community green space, perfect for outdoor relaxation and surrounded by tropical landscaping at 3020 Latitude Ln, Kissimmee, FL 34747
A view from beneath a tiki hut showcases the lush green space and colorful homes of the community at 3020 Latitude Ln, Kissimmee, FL 34747
On Market For 38 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $316

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 Pended $649,000

Two-story light blue house with teal shutters and metal roof at 8133 Surf St, Kissimmee, FL 34747
Charming two-story house near a lake with palm trees at 8133 Surf St, Kissimmee, FL 34747
Two-story light blue house with teal shutters and metal roof at 8133 Surf St, Kissimmee, FL 34747
On Market For 48 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1787

  • Year Built

    2021

  • $/SqFt

    $363

This house isn't just a home – it's a lifestyle! LUXE PROPERTIES LLC.

Rolling Oaks For Sale $495,000

Reduced By $5,000

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 55 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $351

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 $1,975,000

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 57 Days
  • Bedrooms

    8

  • Full Bath(s)

    9

  • Sq. Ft.

    4815

  • Year Built

    2020

  • $/SqFt

    $410

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

Rolling Oaks For Sale $474,900

Open concept living room and kitchen with white cabinets and coastal decor at 2962 Salted Rim Rd, Kissimmee, FL 34747
Living room with sectional sofa and large TV at 2962 Salted Rim Rd, Kissimmee, FL 34747
Living room with sectional sofa and coastal decor at 2962 Salted Rim Rd, Kissimmee, FL 34747
On Market For 67 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2020

  • $/SqFt

    $304

Come see this beautiful cottage today! COLDWELL BANKER REALTY.

Rolling Oaks Pended $350,000

Colorful two-story townhome featuring a landscaped front yard and inviting entry at 2904 On The Rocks Pt, Kissimmee, FL 34747
Bright living room featuring a comfortable sofa, modern decor, and an open layout at 2904 On The Rocks Pt, Kissimmee, FL 34747
Airy living space with a comfortable sofa and a seamless transition to the well-equipped kitchen at 2904 On The Rocks Pt, Kissimmee, FL 34747
On Market For 68 Days
  • Bedrooms

    2

  • Full Bath(s)

    3

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $251

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 70 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 73 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 73 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 Pended $579,000

Open living room with light colored sofas and a view of the kitchen at 8049 Lost Shaker Ln, Kissimmee, FL 34747
Living room with light colored sofas, coffee table, and teal accent chair at 8049 Lost Shaker Ln, Kissimmee, FL 34747
Farmhouse style dining table with six chairs, adjacent to kitchen at 8049 Lost Shaker Ln, Kissimmee, FL 34747
On Market For 69 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2066

  • Year Built

    2019

  • $/SqFt

    $280

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 Pended $495,000

Bright living room with comfy sofa and kitchen views at 2913 Caribbean Soul Dr, Kissimmee, FL 34747
Living room with TV, sofa, and access to patio at 2913 Caribbean Soul Dr, Kissimmee, FL 34747
Living room with TV, sofa, and kitchen views at 2913 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 73 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $288

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 $1,875,000

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 95 Days
  • Bedrooms

    7

  • Full Bath(s)

    8

  • Sq. Ft.

    4335

  • Year Built

    2018

  • $/SqFt

    $433

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

Rolling Oaks For Sale $395,000

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 96 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $283

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 101 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 For Sale $915,000

Reduced By $84,500

Brightly colored houses with palm trees and landscaped yards at 8056 Shaker St, Kissimmee, FL 34747
Private backyard oasis with a pool and patio furniture at 8056 Shaker St, Kissimmee, FL 34747
Inviting pool at night with colorful flamingo floats at 8056 Shaker St, Kissimmee, FL 34747
On Market For 102 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    2632

  • Year Built

    2018

  • $/SqFt

    $348

Margaritaville Resort Features Multiple Pools, a Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More. LOCATED MINUTES FROM DISNEY PARKS! COLDWELL BANKER REALTY.

Rolling Oaks For Sale $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 105 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 $525,000

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 110 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1564

  • Year Built

    2019

  • $/SqFt

    $336

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

Rolling Oaks For Sale $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 111 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 $1,075,000

Two-story home with yellow and blue exterior, landscaping, and palm trees at 8033 Surf St, Kissimmee, FL 34747
Colorful coastal homes with palm trees and lush landscaping create a vibrant and inviting community atmosphere at 8033 Surf St, Kissimmee, FL 34747
Inviting pool and hot tub area with lounge chairs, surrounded by palm trees, perfect for relaxation and enjoyment at 8033 Surf St, Kissimmee, FL 34747
On Market For 117 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2222

  • Year Built

    2018

  • $/SqFt

    $484

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 $1,039,000

Reduced By $60,000

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 129 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    2632

  • Year Built

    2019

  • $/SqFt

    $395

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 171 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 $479,900

Inviting entryway with a blue door and a welcoming mat at 8063 Knee Deep Rd, Kissimmee, FL 34747
Open living room with a comfortable sofa, teal cabinet, and a large TV at 8063 Knee Deep Rd, Kissimmee, FL 34747
Relaxing living room featuring a teal accent chair, sofa, and wood floors at 8063 Knee Deep Rd, Kissimmee, FL 34747
On Market For 172 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $404

If you choose to stay with the same rental company, there are reservations on the books for 2024 and 2025, Or if you want as your primary the bookings can be moved. Schedule a showing today! ! COLDWELL BANKER REALTY.

Rolling Oaks For Sale $645,000

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 176 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1787

  • Year Built

    2022

  • $/SqFt

    $361

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 $754,000

Reduced By $15,000

Relaxing living room with access to a patio and pool at 8014 Knee Deep Rd, Kissimmee, FL 34747
Bright living room with sectional sofa, large TV, and view of the pool at 8014 Knee Deep Rd, Kissimmee, FL 34747
Casual dining area with white table and chairs, adjacent to living room at 8014 Knee Deep Rd, Kissimmee, FL 34747
On Market For 220 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2020

  • $/SqFt

    $408

Buyers and buyer agents are responsible for checking the accuracy of all measurements. UNITED SHARES REAL ESTATE 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 235 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 $549,000

Reduced By $50,000

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 252 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $386

Secure your slice of paradise now! LIFESTYLE INTERNATIONAL REALTY.

Rolling Oaks Pended $699,988

Reduced By $96,009

Living room with gray couch, large TV, and coastal decor at 8025 Sandy Toes Way, Kissimmee, FL 34747
Open living room with comfortable seating and access to dining area at 8025 Sandy Toes Way, Kissimmee, FL 34747
Bright dining area with table and chairs, adjacent to kitchen at 8025 Sandy Toes Way, Kissimmee, FL 34747
On Market For 271 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1948

  • Year Built

    2020

  • $/SqFt

    $359

4 Beds and 4.5 Baths, FL 34747 HOMECOIN.COM.

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 286 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 Pended $499,900

Relaxing patio with lake views, featuring two Adirondack chairs and a small table at 3093 Caribbean Soul Dr, Kissimmee, FL 34747
Townhouse community backs to a tranquil lake with lush green grass at 3093 Caribbean Soul Dr, Kissimmee, FL 34747
Open living area with comfortable seating, a kitchen, and modern appliances at 3093 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 292 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! EXP REALTY LLC.

Rolling Oaks For Sale $429,000

Reduced By $30,000

Bright living room with comfy sofas and kitchen views at 8181 Surf St, Kissimmee, FL 34747
Living room with white sofa, TV, and coastal decor at 8181 Surf St, Kissimmee, FL 34747
Open-concept living area with kitchen and TV at 8181 Surf St, Kissimmee, FL 34747
On Market For 293 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $278

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 298 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. EXP REALTY LLC.

Rolling Oaks For Sale $650,000

Relaxing living room with comfy sofa and large TV at 8029 Sand Bar Dr, Kissimmee, FL 34747
Spacious living room, featuring a large TV and comfortable seating at 8029 Sand Bar Dr, Kissimmee, FL 34747
Open concept kitchen and living area with stainless steel appliances and light flooring at 8029 Sand Bar Dr, Kissimmee, FL 34747
On Market For 299 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2018

  • $/SqFt

    $461

Come and Enjoy the Good Life in Margaritaville! EXP REALTY LLC.

Rolling Oaks For Sale $426,990

Reduced By $33,010

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 305 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $359

REAL BROKER, LLC.

Rolling Oaks For Sale $493,000

Reduced By $117,000

Aerial view of community, highlighting property location at 3062 Pirate Way, Kissimmee, FL 34747
Relax in this private hot tub, located in a tropical courtyard setting at 3062 Pirate Way, Kissimmee, FL 34747
Community courtyard with tropical landscaping and thatch umbrellas at 3062 Pirate Way, Kissimmee, FL 34747
On Market For 307 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $347

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 $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 311 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 Pended $350,000

Reduced By $49,000

Relaxing porch with two Adirondack chairs and a small table at 3091 Key Lime Loop, Kissimmee, FL 34747
Landscaped backyard with patio and palm trees at 3091 Key Lime Loop, Kissimmee, FL 34747
Open living room and kitchen area with modern decor at 3091 Key Lime Loop, Kissimmee, FL 34747
On Market For 289 Days
  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    775

  • Year Built

    2018

  • $/SqFt

    $452

Amazing 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 $550,000

Reduced By $70,000

Community pool view from private backyard patio at 3136 Caribbean Soul Dr, Kissimmee, FL 34747
Community pool and colorful townhomes at 3136 Caribbean Soul Dr, Kissimmee, FL 34747
Bright entryway with tile floors and view into living area at 3136 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 338 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1712

  • Year Built

    2023

  • $/SqFt

    $321

Schedule a private viewing to experience the unparalleled allure of this Key West style oasis. WATSON REALTY CORP..

Rolling Oaks For Sale $580,000

Modern kitchen with white cabinets and island at 2920 Caribbean Soul Dr, Kissimmee, FL 34747
Living room with sectional sofa and large TV at 2920 Caribbean Soul Dr, Kissimmee, FL 34747
Open dining area with rustic wood table and bench at 2920 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 339 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $416

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.

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