Kissimmee, FL Homes for Sale under $500,000

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  $447,900

  • 4 Beds
  • 3.5 Baths
  • 2,513 Sq Ft

  2723 Callaway Ln, Kissimmee, FL 34744

  ***BRAND NEW ROOF INSTALLED JULY 2025 !!!! Spectacular water view!!!!Located in the sought after Windsor Park neighborhood of Remington, a gated golf community. Beautiful 4 bed/3.5 bath, sparking pool home with a beautiful pond views. The two story design features large open kitchen, living room, dining room, family room, a master suite on the ground floor and a further three bedrooms on the

  Lindsy Holland NEXTHOME SUNSHINE REALTY

  2723 Callaway Ln, Kissimmee, FL 34744
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  $485,959 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,582 Sq Ft

  5806 Portico Place, Kissimmee, FL 34758

  What's Special: Corner Lot | Gourmet Kitchen | Loft Welcome to the Anastasia at 5806 Portico Place in Aden North at Westview, where thoughtful design meets Florida living. This spacious floor plan features an open kitchen with a generous pantry and plenty of counter space that flows into the dining area and great room, with a study nearby for added flexibility. The owner’s retreat offers a

  Taylor Morrison Builder

  5806 Portico Place, Kissimmee, FL 34758
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  /40

  $475,000

  • 4 Beds
  • 3 Baths
  • 1,902 Sq Ft

  2569 Reading Trail, Kissimmee, FL 34746

  Best priced townhome with conservation views. This 4 bedroom, 3 bath townhome is located in the highly desired Storey Lake Resort. The home features a modern open layout with a fully equipped kitchen, spacious living and dining areas, and a private screened patio with pool. The first floor offers a guest bedroom and full bath, while upstairs includes a primary suite with ensuite bath and walk in

  Andre Kressler KRESSLER REAL ESTATE

  2569 Reading Trail, Kissimmee, FL 34746
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  $460,000

  • 5 Beds
  • 3.5 Baths
  • 2,532 Sq Ft

  4645 Cumbrian Lakes Dr, Kissimmee, FL 34746

  Welcome to this inviting pool home located in the highly sought-after gated community of Cumbrian Lakes—just minutes from Disney, US-192, world-class dining, shopping, and Orlando’s top attractions. Perfect as a primary residence, vacation home, or short-term rental investment, this property offers comfort, convenience, and resort-style living. Step inside to an open-concept living and dining

  Chris Selzler FLORIDA REALTY MARKETPLACE

  4645 Cumbrian Lakes Dr, Kissimmee, FL 34746
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  $429,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,914 Sq Ft

  4570 Noble St, Kissimmee, FL 34746

  Entering the home from the covered porch, you step into a bright foyer that leads to two bedrooms sharing a full bath. Continuing down the hallway, you’ll find a third bedroom and a laundry room with convenient access to the two-car garage. The layout opens up into a connected kitchen, family room, and dining area, creating a welcoming central living space. A covered patio extends off the family

  Starlight Homes Builder

  4570 Noble St, Kissimmee, FL 34746
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  $465,000

  • 4 Beds
  • 3 Baths
  • 2,746 Sq Ft

  2830 Paynes Prairie Cir, Kissimmee, FL 34743

  Welcome to the gated Heritage Lake Community! This contemporary 4-bedroom, 3-bathroom home has no neighbors in your backyard!! Located near SR 417 and Florida's Turnpike, this home is a short drive to all the excitement of the Walt Disney World Resort, Universal, and SeaWorld. You are just around the corner from the Orlando International Airport, which is the home of the Brightline Railroad

  Colleen Brown CENTURY 21 EDGE

  2830 Paynes Prairie Cir, Kissimmee, FL 34743
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  /56

  $475,000

  • 5 Beds
  • 3.5 Baths
  • 2,636 Sq Ft

  1202 Cumbrian Lakes Ct, Kissimmee, FL 34746

  Discover Resort-style living in this spacious 2 story, 5-Bed, 3.5-Bath Pool home on a waterfront lot in the peaceful Cumbrian Lakes Resort community just minutes from Walt Disney World, Orlando's theme parks, and world-class shopping. This move-in-ready property features an open-concept layout with high ceilings, wood-look laminate floors, and stunning water views.The kitchen offers white

  Damaris Oliva MARKET CONNECT REALTY LLC

  1202 Cumbrian Lakes Ct, Kissimmee, FL 34746
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  $407,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,614 Sq Ft

  1825 Three Bars Rd, Kissimmee, FL 34744

  The property is located at 1825 Three Bars Road KISSIMMEE FL 34744 priced at 407990, the square foot and stories are 1614, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  1825 Three Bars Rd, Kissimmee, FL 34744
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  /18

  $478,440 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,896 Sq Ft

  Durham Plan at Knightsbridge, Kissimmee, FL 34746

  This two-story home is the largest plan in this collection and features an open space living room, along with an airy flex space and a private owner’s suite on the first floor. Upstairs is a spacious loft for an extra common area, along with four comfortable bedrooms.

  Lennar Builder

  1367 Brentwood Dr Unit 36037725, Kissimmee, FL 34746
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  $465,000

  • 2 Beds
  • 2.5 Baths
  • 1,394 Sq Ft

  3192 Caribbean Soul Dr, Kissimmee, FL 34747

  Stunning New Build in 2023, this Townhome has 2 Bedroom 2.5 Bathroom + Bonus Room and 1,350+ square feet of living space in a gated section of Margaritaville Orlando Resort with beautiful furnishings! Walking through the front door into the open downstairs the upgraded kitchen opens into the living and dining space with high ceilings. The stainless steel appliances and granite countertops in the

  Billy Wygle THE WILKINS WAY LLC

  3192 Caribbean Soul Dr, Kissimmee, FL 34747
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  $425,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  CALI Plan at Kindred, Kissimmee, FL 34744

  Introducing the Cali floorplan at Kindred in Kissimmee, Florida, where every square foot is put to use with sophistication and comfort. Inside this 4-bedroom, 2-bathroom home, you’ll find 1,882 square feet of comfortable living. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz counters and luxury vinyl plank floors throughout. As you step

  D.R. Horton Builder

  1508 Park Side Ave Unit 36202646, Kissimmee, FL 34744
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  $489,900

  • 3 Beds
  • 3.5 Baths
  • 2,195 Sq Ft

  3061 Rockefeller Way, Kissimmee, FL 34747

  Experience resort-style living in this stunning 3-bedroom, 3.5-bath townhouse located in the sought-after Magic Village Resort community, with newly **lowered HOA fees** and excellent short-term rental history just minutes from Disney’s Animal Kingdom. From the moment you enter, the bright, open floor plan impresses with high ceilings, beautiful finishes, and seamless flow between the luxury

  Abby Nelson RE/MAX 200 REALTY

  3061 Rockefeller Way, Kissimmee, FL 34747
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  /19

  $404,899 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,790 Sq Ft

  5800 Portico Place, Kissimmee, FL 34758

  What's Special: High Ceilings | Dedicated Study | Covered Patio Welcome to the Saint Vincent at 5800 Portico Place in Aden North at Westview. This thoughtfully designed home offers 1,790 square feet of open-concept living, featuring three spacious bedrooms, two full bathrooms, a convenient half bath, and a versatile study. The heart of the home is bright and welcoming, with natural light flowing

  Taylor Morrison Builder

  5800 Portico Place, Kissimmee, FL 34758
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  /25

  $402,740 New Construction

  • 6 Beds
  • 3 Baths
  • 2,575 Sq Ft

  Concord Plan at Westview - Aden South II, Kissimmee, FL 34758

  This two-story home is designed to meet the evolving needs of large or growing families. The first floor features an open-concept main living area with an attached lanai to enhance outdoor enjoyment, along with a secluded bedroom ideal for overnight guests. Upstairs is a loft surrounded by four secondary bedrooms and the luxurious owner’s suite.

  Lennar Builder

  5638 Loggia Ln Unit 36037847, Kissimmee, FL 34758
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  /12

  $426,990 New Construction

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft

  1957 Walnut Creek Dr, Kissimmee, FL 34744

  The property is located at 1957 Walnut Creek Drive KISSIMMEE FL 34744 priced at 426990, the square foot and stories are 1672, 1.The number of bath is 2, halfbath is 0 there are 3 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  1957 Walnut Creek Dr, Kissimmee, FL 34744
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  $497,999 New Construction

  • 3 - 4 Beds
  • 3 Baths
  • 3,004 Sq Ft

  Pallazio Plan at Esplanade at Westview - 62', Kissimmee, FL 34758

  The open-concept Pallazio home design features ample square footage, several upgrade options both indoors and out, and attractive appointments throughout. Featuring 3,004 square feet, this home offers three bedrooms plus a flex and alternate room layouts such as an optional fourth bedroom giving the design a customizable, more personalized array of possibilities within. The Pallazio is certainly

  Taylor Morrison Builder

  4370 Curacao Place Unit 36603616, Kissimmee, FL 34758
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  $431,540 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,522 Sq Ft

  Sierra Plan at Tohoqua - Cottages Collection, Kissimmee, FL 34744

  This new two-story home is a family-friendly haven with a first-floor dining room for memorable meals, a kitchen for inspired cooks and a family room for great gatherings. A patio is accessed through the family room and the owner’s suite, which is situated on this floor for added privacy. Upstairs are a versatile loft, three secondary bedrooms and a conveniently located laundry room.

  Lennar Builder

  2396 Volunteer Ave Unit 36037777, Kissimmee, FL 34744
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  /11

  $436,990 New Construction

  • 3 - 4 Beds
  • 2 Baths
  • 2,059 Sq Ft

  Plan 2059 Modeled at Hilliard Ridge, Kissimmee, FL 34743

  * Open kitchen overlooking living and dining rooms * Primary bedroom at rear of home for added privacy * Walk-in closet at primary bedroom * Dual-sink vanity at primary bath * Ample kitchen counter space * Stainless steel appliance package * Open floor plan * Split-bedroom layout * Spacious living room * Kitchen island * Dedicated laundry room * ENERGY STAR certified home * Planned basketball

  KB Home Builder

  0 Simpson Rd Unit 36598581, Kissimmee, FL 34743
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  /18

  $409,340 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,795 Sq Ft

  Autumn Plan at Tohoqua - Cottages Collection, Kissimmee, FL 34744

  This new two-story home showcases a pleasing, contemporary design. The first floor features a large entry and an open floorplan among the modern kitchen, tranquil dining room and inviting family room. The laundry room is located by the kitchen, and a lanai is tucked beside the family room. Upstairs, three bedrooms including a lavish owner’s suite provide restful retreats for family members and

  Lennar Builder

  2396 Volunteer Ave Unit 36037778, Kissimmee, FL 34744
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  /13

  $439,990 New Construction

  • 4 Beds
  • 2 Baths
  • 2,345 Sq Ft

  Spectra Plan at Hawks Run, Kissimmee, FL 34746

  Welcome to your next home! As you enter from the covered porch, you’re greeted by a flex room. Continuing through the main level, you pass a powder bath and the two-car garage before stepping into the open kitchen, dining area, and family room. A back patio is located just off the dining area. Upstairs, a spacious loft connects three additional bedrooms—each with a walk-in closet—and a shared

  Starlight Homes Builder

  2406 Duck Hawk St Unit 36893612, Kissimmee, FL 34746
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  $429,999 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,582 Sq Ft

  Anastasia Plan at Westview - Aden North 40', Kissimmee, FL 34758

  The spacious Anastasia floor plan offers a unique layout that’s ideal for Florida living. The foyer angles off the front porch, with access to the laundry room and a half bathroom on the right. Straight ahead, the designer kitchen with offers pantry and counter space with the sink square to the open dining room and great room area. The main level also includes a study with French doors, you may

  Taylor Morrison Builder

  5638 Loggia Ln Unit 38854769, Kissimmee, FL 34758
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  $450,000

  • 2 Beds
  • 2 Baths
  • 2,211 Sq Ft

  699 Villa Park Rd, Kissimmee, FL 34759

  Stunning Boca Raton model featuring a GOLF CART GARAGE and a BRAND-NEW STONE-COATED METAL TILE ROOF(2025), overlooking breathtaking WATER VIEWS!! In addition, all NEW GUTTERS, FASCIA, and SOFFITS were replaced with the new roof. This beautifully maintained home offers upgrades galore, including PLANTATION SHUTTERS , CROWN MOLDING in the bedrooms, 8-foot doors, and soaring ceilings. The kitchen

  Yamile Osorio Varrone BORCHINI REALTY

  699 Villa Park Rd, Kissimmee, FL 34759
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  $457,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft

  1829 Three Bars Rd, Kissimmee, FL 34744

  The property is located at 1829 Three Bars Road KISSIMMEE FL 34744 priced at 457990, the square foot and stories are 2447, 2.The number of bath is 3, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  1829 Three Bars Rd, Kissimmee, FL 34744
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  $400,000 New Construction

  • 2 Beds
  • 2 Baths
  • 1,886 Sq Ft

  4228 Barbuda Ln, Kissimmee, FL 34758

  Welcome to the Azzurro at 4228 Barbuda Lane in Esplanade at Westview! This thoughtfully designed home offers 1,886 square feet of flexible living space with two bedrooms and two baths. The open-concept layout features a chef-inspired kitchen with a walk-in pantry and a spacious island that flows into the dining area and great room—perfect for entertaining. Sliding doors lead to a covered lanai

  Taylor Morrison Builder

  4228 Barbuda Ln, Kissimmee, FL 34758
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  /40

  $470,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft

  HAYDEN Plan at Kindred, Kissimmee, FL 34744

  Find all the space you need in our popular two-story Hayden floorplan in Kindred, one of our communities in Kissimmee, Florida. Inside this 5-bedroom, 3-bathroom home, you’ll find 2,601 square feet of flexible living space and a two-car garage. Step thru the front foyer and you're greeted with a flex room designed for work or play. Make your way to the kitchen on the first floor, which overlooks

  D.R. Horton Builder

  1508 Park Side Ave Unit 36202647, Kissimmee, FL 34744
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  /14

  $472,707 New Construction

  • 3 Beds
  • 2 Baths
  • 2,082 Sq Ft

  Bourne II Plan at Tohoqua - Estates Collection, Kissimmee, FL 34744

  This new home is conveniently laid out on a single floor. It features an open kitchen, a family room that flows seamlessly into the dining room and opens out to the covered patio plus a versatile flex space. Two secondary bedrooms and an owner’s suite with a bathroom featuring a separate tub and shower offer restful retreats for family members or guests.

  Lennar Builder

  2396 Volunteer Ave Unit 36037782, Kissimmee, FL 34744
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  /18

  $446,999 New Construction

  • 3 Beds
  • 3 Baths
  • 2,296 Sq Ft

  Ambra Plan at Esplanade at Westview - 52', Kissimmee, FL 34758

  The Ambra is totally on-trend, with features inspired by homeowners like you. The open concept living area combines the great room, a spacious kitchen with large central working island, and an expansive view of the lanai. What really sets it apart are the two primary suites, each with spacious walk-in closets and baths with walk-in showers. In-demand options include bay windows, media room in

  Taylor Morrison Builder

  4370 Curacao Place Unit 36603474, Kissimmee, FL 34758
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  /15

  $459,990 New Construction

  • 3 - 5 Beds
  • 2.5 - 4.5 Baths
  • 2,226+ Sq Ft

  Plant at Hawks Run, Kissimmee, FL 34746

  The Plant is a one-story home offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The spacious kitchen features a large island and flows seamlessly into the dining and family rooms. A private primary suite includes a walk-in closet, while a generously sized den and covered lanai provide versatile living spaces for work, relaxation, and outdoor enjoyment. Modern

  Ashton Woods Builder

  2424 Duck Hawk St Unit 36631989, Kissimmee, FL 34746
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  $459,000

  • 4 Beds
  • 3 Baths
  • 1,914 Sq Ft

  4895 Clock Tower Dr, Kissimmee, FL 34746

  EXCELLENT OPPORTUNITY in a PRIME LOCATION! Discover this CHARMING,TURN-KEY home with a private pool, just minutes from Disney Parks and Orlando outlets. PERFECT FOR investors, snowbirds, and Disney enthusiasts-use it for vacations and earn high income when you're away. Located In Kissimmee's top short-term rental community, this beautifully decorated and meticulously maintained home features 4

  Eveli Golden EXP REALTY LLC

  4895 Clock Tower Dr, Kissimmee, FL 34746
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  $484,900

  • 5 Beds
  • 3.5 Baths
  • 2,572 Sq Ft

  4663 Cumbrian Lakes Dr, Kissimmee, FL 34746

  Welcome to the sought-after gated community of Cumbrian Lakes. This home is Short Term Rental approved and already has bookings thru the end of the year!! This large5-bedroom home offers an exceptional lifestyle complete with water views and pool. Whether you’re searching for a permanent residence, a vacation getaway, or a seasonalretreat, this fully furnished is it. The expansive first

  Debbie Lynn FLORIDA REALTY RESULTS LLC

  4663 Cumbrian Lakes Dr, Kissimmee, FL 34746
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  /18

  $416,640 New Construction

  • 5 Beds
  • 2.5 Baths
  • 2,370 Sq Ft

  Columbia Plan at Westview - Aden South II, Kissimmee, FL 34758

  This two-story home divides space for optimal tranquility. The first floor showcases an open design that encompasses the dining room, kitchen and living room for simplified family living and entertaining. Nearby, the owner’s suite is separate from the upstairs bedrooms and features a private bathroom. The second level hosts four additional bedrooms and a versatile loft.

  Lennar Builder

  5638 Loggia Ln Unit 36037846, Kissimmee, FL 34758
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  $499,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,226 Sq Ft

  2581 Broadwing St, Kissimmee, FL 34746

  Discover the perfect blend of style and comfort in this stunning home from Ashton Woods’ Harmony Collection, offering a peaceful water-view backyard. The thoughtfully designed open floor plan features durable vinyl plank flooring throughout the main living areas and a versatile den or office space for work or relaxation. The chef-inspired kitchen boasts 42 cabinets, elegant quartz countertops,

  Ashton Woods Builder

  2581 Broadwing St, Kissimmee, FL 34746
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  /27

  $459,990 New Construction

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft

  1833 Three Bars Rd, Kissimmee, FL 34744

  The property is located at 1833 Three Bars Road KISSIMMEE FL 34744 priced at 459990, the square foot and stories are 2447, 2.The number of bath is 3, halfbath is 0 there are 5 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  1833 Three Bars Rd, Kissimmee, FL 34744
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  $499,990 New Construction

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft

  2005 Walnut Creek Dr, Kissimmee, FL 34744

  The property is located at 2005 Walnut Creek Drive KISSIMMEE FL 34744 priced at 499990, the square foot and stories are 2108, 1.The number of bath is 3, halfbath is 0 there are 4 bedrooms and 3 garages. For more details please, call or email.

  D.R. Horton Builder

  2005 Walnut Creek Dr, Kissimmee, FL 34744
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  /21

  $406,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  4222 Barbuda Ln, Kissimmee, FL 34758

  Welcome to the Farnese at 4222 Barbuda Lane in Esplanade at Westview! This elegant new home is designed for both style and functionality. At the heart of the layout, the gorgeous designer kitchen shines with 42-inch cabinets, sleek quartz countertops, and an expansive island that overlooks the great room and casual dining area, perfect for entertaining or everyday living. A separate formal dining

  Taylor Morrison Builder

  4222 Barbuda Ln, Kissimmee, FL 34758
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  /45

  $499,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,226 Sq Ft

  2597 Broadwing St, Kissimmee, FL 34746

  Live the relaxed Florida lifestyle in this beautiful Sunbrooke home, inspired by Ashton Woods’ Coastal Collection. Located in a charming enclave of just 85 homesites surrounded by conservation, this thoughtfully designed residence blends coastal-inspired finishes with modern comfort. Inside, enjoy open living spaces, stylish design selections, and quality finishes throughout. Sunbrooke offers

  Ashton Woods Builder

  2597 Broadwing St, Kissimmee, FL 34746
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  /15

  $455,820 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,595 Sq Ft

  Providence Plan at Knightsbridge, Kissimmee, FL 34746

  This new two-story home is a family-friendly haven. Located off the foyer is a flex room for versatility, followed by an open-plan layout among a family room for great gatherings, a dining room for memorable meals and a modern kitchen. The second floor hosts a loft that adds shared living space to the home, a conveniently located laundry room and all four bedrooms including a luxurious owner’s

  Lennar Builder

  1367 Brentwood Dr Unit 36037724, Kissimmee, FL 34746
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  /24

  $414,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,914 Sq Ft

  Equinox Plan at Hawks Run, Kissimmee, FL 34746

  Entering the home from the covered porch, you step into a bright foyer that leads to two bedrooms sharing a full bath. Continuing down the hallway, you’ll find a third bedroom and a laundry room with convenient access to the two-car garage. The layout opens up into a connected kitchen, family room, and dining area, creating a welcoming central living space. A covered patio extends off the family

  Starlight Homes Builder

  2406 Duck Hawk St Unit 36893617, Kissimmee, FL 34746
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  /46

  $439,900

  • 4 Beds
  • 2 Baths
  • 2,259 Sq Ft

  3028 Camino Real Dr S, Kissimmee, FL 34744

  POOL HOME ALERT! Welcome to 3028 Camino Real Drive S, where comfort meets Florida lifestyle in one of Kissimmee’s most sought-after communities! This stunning 4-bedroom, 2-bathroom beauty features your very own private screen-enclosed pool—perfect for cooling off, hosting unforgettable BBQs, or just relaxing under the sun. Step inside and be wowed by the bright, open layout, spacious living and

  John Joseph CENTRIC REALTY SERVICES LLC

  3028 Camino Real Dr S, Kissimmee, FL 34744
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  /72

  $455,000

  • 3 Beds
  • 3 Baths
  • 2,319 Sq Ft

  217 Sorrento Rd, Kissimmee, FL 34759

  PRICE REDUCTION! Located in a highly sought-after Solivita 55+ golf course community, this beautifully upgraded Bolero model offers 3 bedrooms, 3 bathrooms, a 2-car garage plus a dedicated golf cart garage, all with picturesque pond and golf course views. A separate-entry casita in-law suite provides ideal guest accommodations or private office space. Enjoy serene outdoor living in the expansive

  Stan Wilson PELLEGO, LLC

  217 Sorrento Rd, Kissimmee, FL 34759

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