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 954 439 6446.

61 Results

Rolling Oaks Kissimmee Florida Homes For Sale

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 6 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 6 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 For Sale $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 16 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 $500,000

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 23 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1410

  • Year Built

    2019

  • $/SqFt

    $355

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 25 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 Pended $359,900

Open living space with kitchen island and tiled floor at 2907 Castaway Ln, Kissimmee, FL 34747
Bright hallway with coastal decor and view of living area at 2907 Castaway Ln, Kissimmee, FL 34747
Modern kitchen with white cabinets, island, and stainless steel appliances at 2907 Castaway Ln, Kissimmee, FL 34747
On Market For 32 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1394

  • Year Built

    2022

  • $/SqFt

    $258

DON’T MISS this Opportunity to start owning an investment in the HAPPIEST PLACE ON EARTH! MUST-SEE, MUST-HAVE! DS REALTY GROUP LLC.

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 35 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 For Sale $350,000

Aerial view of community pool surrounded by palm trees, cabanas, and lounge chairs, perfect for relaxation at 2904 On The Rocks Pt, Kissimmee, FL 34747
Bright living area with stylish furniture, wood floors, and an open floorplan to the kitchen area at 2904 On The Rocks Pt, Kissimmee, FL 34747
Cozy living room featuring wood floors and an open floorplan connecting it to the kitchen area at 2904 On The Rocks Pt, Kissimmee, FL 34747
On Market For 35 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 38 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 41 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 41 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 $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 41 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 41 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 63 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 64 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 69 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 $925,000

Reduced By $74,500

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 71 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    2632

  • Year Built

    2018

  • $/SqFt

    $351

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 73 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 78 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 $495,000

Reduced By $45,000

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 79 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2023

  • $/SqFt

    $288

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

Rolling Oaks For Sale $1,075,000

Community pool and spa with lounge chairs at 8033 Surf St, Kissimmee, FL 34747
Shared pool and spa area with lounge chairs at 8033 Surf St, Kissimmee, FL 34747
Row of colorful townhomes with lush landscaping at 8033 Surf St, Kissimmee, FL 34747
On Market For 85 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 Pended $1,097,000

Private pool and spa with lounge chairs and lake view at 8013 Surf St, Kissimmee, FL 34747
Covered patio with wooden dining table and pool access at 8013 Surf St, Kissimmee, FL 34747
Refreshing pool with spa and brick patio area at 8013 Surf St, Kissimmee, FL 34747
On Market For 91 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2632

  • Year Built

    2019

  • $/SqFt

    $417

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 $525,000

Bright yellow townhome with balcony, coral accents and tropical landscaping at 3013 Sea Plane Ln, Kissimmee, FL 34747
Two-story yellow townhome with balcony, coral shutters and tropical landscaping at 3013 Sea Plane Ln, Kissimmee, FL 34747
Private patio with table and chairs, perfect for outdoor dining at 3013 Sea Plane Ln, Kissimmee, FL 34747
On Market For 91 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1384

  • Year Built

    2019

  • $/SqFt

    $379

Check out the 3D tour online and schedule a private viewing today! REDFIN CORPORATION.

Rolling Oaks Pended $429,000

Reduced By $16,000

Covered front porch with brick flooring and seating at 3063 Pirate Way, Kissimmee, FL 34747
Front door with a peach door and welcome mat at 3063 Pirate Way, Kissimmee, FL 34747
Bright living room with blue accent wall and comfy couch at 3063 Pirate Way, Kissimmee, FL 34747
On Market For 93 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1217

  • Year Built

    2018

  • $/SqFt

    $353

Just minutes from Disney and situated in Phase One of Margaritaville, this fully furnished home offers the flexibility to live full-time or participate in the rental program as much or as little as you desire. LUXE PROPERTIES LLC.

Rolling Oaks For Sale $1,049,000

Reduced By $50,000

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 97 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    2632

  • Year Built

    2019

  • $/SqFt

    $399

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

Rolling Oaks Pended $399,000

Front entrance of a pastel-colored townhouse with landscaping at 2968 On The Rocks Pt, Kissimmee, FL 34747
Cozy bedroom with a comfortable bed, window blinds, and artwork at 2968 On The Rocks Pt, Kissimmee, FL 34747
Clean bathroom with a shower, toilet, and vanity with a countertop at 2968 On The Rocks Pt, Kissimmee, FL 34747
On Market For 72 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $258

This beautiful Villa is furnished through the City Furniture and Housewares Package (*included with purchase with Full Price Contract, and includes ALL the Furnishings and Accessories, Blinds, Drapes, TV's, Artwork, Kitchen Necessities, Dishes, Linens, and so much more...) Don't miss this opportunity - make your appointment to see this captivating Villa today and be in your new home before the holidays! REMAX EXPERTS.

Rolling Oaks Pended $475,000

Reduced By $45,000

Bright and airy entryway with a large mirror and console table at 3013 Caribbean Soul Drive Dr, Kissimmee, FL 34747
Modern kitchen with white cabinets, stainless steel appliances, and quartz countertops at 3013 Caribbean Soul Drive Dr, Kissimmee, FL 34747
Modern kitchen with white cabinets and stainless steel appliances at 3013 Caribbean Soul Drive Dr, Kissimmee, FL 34747
On Market For 98 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1719

  • Year Built

    2022

  • $/SqFt

    $276

If you're looking for a permanent residence or a lucrative investment opportunity for short-term rentals, come on and take a look now! LA ROSA REALTY KISSIMMEE.

Rolling Oaks Pended $385,000

Reduced By $3,000

Margaritaville Resort entrance with flags at 2921 Caribbean Soul Dr, Kissimmee, FL 34747
Studio Movie Grill exterior view at 2921 Caribbean Soul Dr, Kissimmee, FL 34747
Yeoman's Cask & Lion Pub exterior at 2921 Caribbean Soul Dr, Kissimmee, FL 34747
On Market For 118 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $249

Don’t miss out on owning a piece of paradise in Margaritaville! LUXE PROPERTIES.

Rolling Oaks For Sale $1,595,000

Reduced By $75,000

Two-story yellow house with gray shutters and a front porch at 8149 Surf St, Kissimmee, FL 34747
Community pool with spa and lake view at 8149 Surf St, Kissimmee, FL 34747
Community of colorful houses with private pools at 8149 Surf St, Kissimmee, FL 34747
On Market For 138 Days
  • Bedrooms

    7

  • Full Bath(s)

    7

  • Sq. Ft.

    4212

  • Year Built

    2020

  • $/SqFt

    $379

Please schedule your private showing today! REAL BROKER, LLC.

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 139 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 140 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 144 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 $499,000

Reduced By $50,000

Front view of a two-story orange house with balcony and green shutters at 8027 Knee Deep Rd, Kissimmee, FL 34747
Aerial view of a house with private pool and spa at 8027 Knee Deep Rd, Kissimmee, FL 34747
Aerial view showing location of the house in a neighborhood at 8027 Knee Deep Rd, Kissimmee, FL 34747
On Market For 154 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2021

  • $/SqFt

    $420

Margaritaville Resort provides exclusive access to multiple pools, live music, fitness centers, on-site water parks, restaurants, and bars, giving you a slice of paradise right at your doorstep. XCELLENCE REALTY INC..

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 188 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 $599,000

Reduced By $26,000

Two-story home with gray siding, balcony, and tropical landscaping at 8053 Lost Shaker Ln, Kissimmee, FL 34747
Two-story home with gray siding, balcony, and tropical landscaping at 8053 Lost Shaker Ln, Kissimmee, FL 34747
Front entrance of two-story home with gray siding and landscaping at 8053 Lost Shaker Ln, Kissimmee, FL 34747
On Market For 209 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    1850

  • Year Built

    2019

  • $/SqFt

    $324

Embrace the Margaritaville lifestyle in this exceptional property! COLDWELL BANKER REALTY.

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 209 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 220 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 For Sale $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 239 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 $640,000

Reduced By $9,900

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 254 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2019

  • $/SqFt

    $352

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 $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 260 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 $459,000

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 261 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1545

  • Year Built

    2022

  • $/SqFt

    $297

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 266 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 267 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 well-manicured 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 273 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1188

  • Year Built

    2019

  • $/SqFt

    $359

REAL BROKER, LLC.

Rolling Oaks For Sale $519,000

Reduced By $91,000

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 275 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1422

  • Year Built

    2018

  • $/SqFt

    $365

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 $749,900

Reduced By $50,090

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 279 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1818

  • Year Built

    2018

  • $/SqFt

    $412

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 256 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 306 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 307 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.

Rolling Oaks For Sale $1,545,000

Reduced By $100,000

Bright entryway with stairs, tile floors, and a view to the living area at 8001 Surf St, Kissimmee, FL 34747
Bedroom with gray wood-like flooring, ceiling fan, and gray bed frame at 8001 Surf St, Kissimmee, FL 34747
Main bedroom with large dresser, TV, and double doors to closet and bathroom at 8001 Surf St, Kissimmee, FL 34747
On Market For 319 Days
  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    3563

  • Year Built

    2019

  • $/SqFt

    $434

Don't miss your chance to own a piece of paradise in one of Orlando's most coveted destinations. REAL BROKER, LLC.

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Call to Schedule a Showing

(954) 439-6446

(954) 439-6446