Eastside Homes for Sale

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  /20

  $245,000

  • 3 Beds
  • 3 Baths
  • 1,187 Sq Ft

  7646 Long Island Dr, Kissimmee, FL 34747

  Beautifully and updated fully furnished and equipped 3-bedroom, 3 full-bath townhome located in the gated community of Crestwynd Bay in KissimmeeFully Furnished townhome equipped with smart locks and thermostat with alarm system, corian counters with 42 inches cabinets. One bedroom with Full bathroom located on the first floor. All bedrooms and living room equipped with smart TV. Residents of

  Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

  7646 Long Island Dr, Kissimmee, FL 34747
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  /38

  $410,000

  $29K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  7681 Sir Kaufmann Ct, Kissimmee, FL 34747

  Welcome to this beautifully maintained 3-bedroom, 3-bath end-unit townhome featuring a private splash pool, located in the highly desirable Windsor Hills Resort, a premier guard-gated community just minutes from Walt Disney World. The home features a well-appointed kitchen with granite countertops, custom backsplash, and updated appliances (2019–2021), creating a functional and stylish space for

  Nikita Walker STOCKWORTH REALTY GROUP

  7681 Sir Kaufmann Ct, Kissimmee, FL 34747
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  /29

  $379,999

  • 3 Beds
  • 2 Baths
  • 1,535 Sq Ft

  1085 Indian Ridge Trail E, Kissimmee, FL 34747

  Just minutes from the magic of Disney (only 4 miles away!), this beautifully updated 3-bedroom, 2-bathroom home offers the perfect blend of comfort and opportunity. Step outside to your private, fenced backyard oasis with a screened and covered patio and a newly renovated pool, all overlooking a serene, open park-like setting. Inside, the thoughtful split floorplan provides privacy for all, while

  Mayra Rivas Acevedo CASA SOL REALTY LLC

  1085 Indian Ridge Trail E, Kissimmee, FL 34747
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  /40

  $380,000

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  7663 Sir Kaufmann Ct, Kissimmee, FL 34747

  Beautiful community Windsor Hills, located only 2 miles from Disney, tons of amenities, private screenedheated splash pool!

  Jorge Zea BLUE LIGHTHOUSE REALTY INC

  7663 Sir Kaufmann Ct, Kissimmee, FL 34747
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  /92

  $425,000

  • 3 Beds
  • 3 Baths
  • 1,545 Sq Ft

  3113 Caribbean Soul Dr, Kissimmee, FL 34747

  Welcome to Paradise! This Beautifully Furnished WATERFRONT VILLA in Margaritaville Resort has 3 Bedrooms, 3 Baths, High-End Quartz Countertops, Upgraded "Wood" Tile Flooring and Appliances. Kitchen has Island with Seating, Stainless Steel Appliances, Large Counter Space and Windows with Lots of Natural Light. Master Bedroom Located Upstairs has En Suite Bathroom. Each Bedroom has Ceiling Fans and

  Suzanne Docobo EXP REALTY LLC

  3113 Caribbean Soul Dr, Kissimmee, FL 34747
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  /84

  $359,999

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,545 Sq Ft

  2916 On the Rocks Point, Kissimmee, FL 34747

  Welcome to paradise at 2916 On The Rocks Pt, a stunning, turnkey-ready 3-bedroom, 3-bathroom townhome located in the highly coveted Margaritaville Resort Orlando. Sold fully furnished and beautifully decorated, this property features a bright, open-concept living area that seamlessly transitions to your own private patio space—perfect for soaking in the warm Florida sunshine. Best of all, you are

  James Donovan TEAM DONOVAN

  2916 On the Rocks Point, Kissimmee, FL 34747
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  /47

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft

  1085 Jodi Ridge Ct, Kissimmee, FL 34747

  UP TO $5,000 TOWARDS CLOSING COSTS! NEW FLOORING AND BASEBOARDS, INSTALLED LATE JULY 2026 NOT SHOWING IN PRO PICTURES YET! Here's your shot at a true Central Florida gem-this bright, welcoming 3-bedroom, 2-bath home in the heart of Indian Ridge, just minutes from Disney and all the magic that makes Kissimmee famous! You can't beat the location, location, location-proximity to Disney parks is

  Cathy Starkweather La Rosa Realty Llc

  1085 Jodi Ridge Ct, Kissimmee, FL 34747
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  /48

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  2788 Almaton Loop Unit 404, Kissimmee, FL 34747

  Experience the best of Central Florida living in this beautifully maintained and fully furnished 3-bedroom, 2-bath condominium located within the highly sought-after Windsor Hills Resort. Situated on the 4th floor with convenient elevator access, this spacious residence offers the perfect blend of comfort, convenience, and investment potential. From the moment you step inside, you'll appreciate

  Corey Smallman MARKET CONNECT REALTY LLC

  2788 Almaton Loop Unit 404, Kissimmee, FL 34747
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  /21

  $445,900

  • 4 Beds
  • 3 Baths
  • 1,662 Sq Ft

  2914 Blooming Alamanda Loop, Kissimmee, FL 34747

  TURNKEY 4-BEDROOM POOL HOME NEAR DISNEY! Welcome to this beautifully located 4-bedroom, 3-bath home in desirable Oak Island Cove, Kissimmee. Just minutes from Walt Disney World, Margaritaville, shopping, dining, and Central Florida’s world-famous attractions, this home is an ideal primary residence, vacation home, or second home. The spacious open floor plan features two primary suites, bright

  Tony Zuco REALTY HUB

  2914 Blooming Alamanda Loop, Kissimmee, FL 34747
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  /8

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,557 Sq Ft

  1647 Key Bay Trail, Kissimmee, FL 34747

  Short Sale. Welcome to this meticulously maintained, upgraded Villa with its own private heated salt water pool in the highly sought after Four Seasons at Orlando. It sits on a peaceful cul-de-sac. The open plan home has so much including upgraded vinyl flooring, exquisite kitchen, quartz countertops, office/den/formal dining room, indoor laundry room, walk in closets, pond view and much more.

  Kavita Uttamchandani CENTURY 21 CARIOTI

  1647 Key Bay Trail, Kissimmee, FL 34747
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  /14

  $355,000

  • 2 Beds
  • 2 Baths
  • 1,557 Sq Ft

  1691 Key Bay Trail, Celebration, FL 34747

  Welcome to resort-style living in the highly sought-after 55+ gated community of Four Seasons at Orlando! Built in 2022, this beautifully designed 2-bedroom, 2-bath villa with a dedicated home office offers modern comfort, elegant finishes, and low-maintenance living just minutes from Disney, world-class attractions, shopping, dining, and major highways. Step inside to an open and spacious floor

  Rabie Georgey PROPERTIES IN TOWN

  1691 Key Bay Trail, Celebration, FL 34747
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  /31

  $249,000

  $26K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 501 Sq Ft

  3151 Sunset Walk Dr Unit 511, Kissimmee, FL 34747

  Experience vibrant resort-style living at 3151 Sunset Walk Dr, Suite 511—a beautifully appointed condo-hotel unit located within Embassy Suites by Hilton. This studio-style suite offers stunning views, exceptional amenities, and full rental flexibility with the option for professional management. Ideally situated in the heart of Kissimmee’s lively Sunset Walk district, this turnkey property

  Robert Rivera BROKER HUB REALTY GROUP LLC

  3151 Sunset Walk Dr Unit 511, Kissimmee, FL 34747
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  /2

  $484,900

  New Construction

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft

  8060 Vacation Ave Unit 100, Kissimmee, FL 34747

  Discover the perfect blend of comfort, convenience, and investment potential with this beautifully furnished 2-bedroom, 2-bathroom residence Designed with both short-term rental investors and vacation homeowners in mind, this stylish condo delivers the feel of a private retreat while benefiting from the prestige and amenities of a globally recognized hotel brand. Situated in one of the

  ??Oficina BRG. 24 X 7 BRICKELL REALTY GROUP INTERNATIONAL LLC

  8060 Vacation Ave Unit 100, Kissimmee, FL 34747
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  /43

  $475,000

  $75K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,113 Sq Ft

  3151 Sunset Walk Dr Unit 212, Kissimmee, FL 34747

  Expect to be amazed when you walk into this ultra comfortable and stylishly modern condo. Everything about it shouts comfort and luxury. A perfect retreat in the heart of Margaritaville and right next door to Disney. Enter into the gorgeous kitchen which has upscale appliances, chic cabinets and a center island which provides additional workspace as well as a convenient place to eat. Its well

  Wendy Karaffa SIGNATURE COLLECTION REALTY IN

  3151 Sunset Walk Dr Unit 212, Kissimmee, FL 34747
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  /24

  $379,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,188 Sq Ft

  8063 Knee Deep Rd, Four Corners, FL 34747

  ***FABULOUS MARGARITAVILLE RESORT***FANTASTIC RENTAL OR VACATION HOME*** OWN ONE OF THE BEST LEASING FLOORPLANS with a DOWNSTAIRS Bedroom and BATH*** Your opportunity to own a TROPICAL COTTAGE OASIS in Margaritaville Resort Orlando! Enjoy 5 O'clock somewhere everyday!!! The property is perfect as a Primary Residence or use it as an INVESTMENT / VACATION home and be part of the Margaritaville

  Randall Gill COLDWELL BANKER REALTY

  8063 Knee Deep Rd, Four Corners, FL 34747
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  /17

  $529,000

  • Studio
  • 1 Bath
  • 600 Sq Ft

  3151 Sunset Walk Dr Unit 516, Kissimmee, FL 34747

  Experience Resort-Style at its finest in this beautiful furnished studio. Property located at Embassy Suites by Hilton, Sunset Walk. This property provides direct access to the main lobby. It offers a complimentary breakfast area, lobby bar, fitness center, laundry facilities, and among others. Owners and guests can enjoy an array of exceptional resort amenities, including a tropical lagoon-style

  Carlos Cedeno Ramirez LA ROSA REALTY LLC

  3151 Sunset Walk Dr Unit 516, Kissimmee, FL 34747
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  /68

  $289,000

  • 2 Beds
  • 2 Baths
  • 1,081 Sq Ft

  2774 Almaton Loop Unit 202, Kissimmee, FL 34747

  Meticulously maintained and truly turn-key 2-bedroom, 2-bathroom condo in the sought-after, guard-gated Windsor Hills Resort community — just minutes from Walt Disney World, Universal Studios, and all the magic of Central Florida’s theme park corridor! This recently painted unit has been thoughtfully upgraded from top to bottom, making it a fantastic primary residence, vacation getaway, or

  Devin Costley ERA GRIZZARD REAL ESTATE

  2774 Almaton Loop Unit 202, Kissimmee, FL 34747
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  /44

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft

  2778 Almaton Loop Unit 303, Kissimmee, FL 34747

  Welcome to an exceptional opportunity in the highly sought-after Windsor Hills Resort, one of Central Florida's premier vacation destinations. Perfectly positioned just minutes from Walt Disney World, this beautifully renovated 3-bedroom, 2-bath condominium at 2778 Almaton Loop #303 offers the ideal blend of luxury, comfort, and investment potential. Offered fully furnished with stylish, updated

  Yair Burac Rodriguez REALTY OF AMERICA

  2778 Almaton Loop Unit 303, Kissimmee, FL 34747
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  /15

  $529,000

  • 1 Bed
  • 1 Bath
  • 630 Sq Ft

  3151 Sunset Walk Dr Unit 416, Kissimmee, FL 34747

  Experience the pinnacle of resort-style living in this impeccably furnished studio, ideally situated in Embassy Suites by Hilton at Sunset Walk. This exceptional property offers direct access to the main lobby and provides an elevated level of convenience with amenities such as a complimentary breakfast area, lobby bar, fitness center, and on-site laundry facilities.Residents and guests enjoy

  Carlos Cedeno Ramirez LA ROSA REALTY LLC

  3151 Sunset Walk Dr Unit 416, Kissimmee, FL 34747
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  /99

  $1,375,000

  $500K PRICE DROP

  • 8 Beds
  • 8.5 Baths
  • 4,335 Sq Ft

  3056 Parrot Head Place, Kissimmee, FL 34747

  'EASY BREEZY' Cottage on Margaritaville Resort Orlando's 'TROPHY ROW'! EXTREMELY RARE OPPORTUNITY TO OWN ONE of the LARGEST WATERFRONT COTTAGES WITH POOL and SPA Plus Your Very Own ELEVATOR ($40k Upgrade)! Home is FULLY HANDICAP ACCESSIBLE. 4131-A Model, 8 Bedrooms, 8 Full Bathrooms and 1 Half Bathroom with IN PARADISE Upgrade. This Amazing Home Features One En Suite Bedroom on First Floor Along

  Suzanne Docobo EXP REALTY LLC

  3056 Parrot Head Place, Kissimmee, FL 34747
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  /23

  $625,000

  $50K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 2,297 Sq Ft

  2648 Dinville St, Kissimmee, FL 34747

  Welcome to this beautifully updated beach-themed oasis, a fully renovated and furnished STR home located in the heart of Kissimmee. This property underwent a complete renovation in 2022, featuring a modernized kitchen with updated cabinetry, countertops, and appliances, along with new flooring and fresh interior paint throughout. Major capital improvements include a new roof (2022) and a recently

  Steven Koleno BEYCOME OF FLORIDA LLC

  2648 Dinville St, Kissimmee, FL 34747
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  /19

  $556,000

  • 1 Bed
  • 1 Bath
  • 745 Sq Ft

  3151 Sunset Walk Dr Unit 302, Kissimmee, FL 34747

  This beautifully appointed 1-bedroom, 1-bathroom condo offers an amazing view and an unbeatable location. Owners and guests enjoy an impressive array of resort amenities, including a tropical lagoon-style pool with splash pad, hot tub, private cabanas, a 24-hour fitness center, on-site dining, a poolside bar, and evening cocktail receptions. Complimentary shuttle service provides effortless

  Carlos Cedeno Ramirez LA ROSA REALTY LLC

  3151 Sunset Walk Dr Unit 302, Kissimmee, FL 34747
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  /26

  $690,000

  $50K PRICE INCREASE

  • 6 Beds
  • 4 Baths
  • 2,812 Sq Ft

  2623 Pawnall St, Kissimmee, FL 34747

  Busy rental: Next available to view is July 26! Minutes to Animal Kingdom! Guest friendly, fun, and full of upgrades! This vacation home has been thoughtfully improved with themed spaces throughout, including a fully themed garage/game area guests will love. Located right next to one of the playgrounds, it offers extra convenience for families and a standout experience in the highly desirable

  Holly Hudson EXP REALTY LLC

  2623 Pawnall St, Kissimmee, FL 34747
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  /20

  $329,000

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

  3008 Caribbean Soul Dr, Kissimmee, FL 34747

  Bright and spacious TWO BEDROOM VILLA WITH BONUS BUNK ROOM located in the heart of Margaritaville Resort just 5 minutes from Disney! This spacious townhome is located on a premium lot with open greenspace views and has two large bedrooms, plus a bonus bunk room, cozy and perfect for children or guests. It also comes with high end wood look tile, quartz countertops, upgraded appliances, wooden

  Jenna Palmero COLDWELL BANKER REALTY

  3008 Caribbean Soul Dr, Kissimmee, FL 34747
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  /51

  $353,000

  $4K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,545 Sq Ft

  2924 Caribbean Soul Dr, Kissimmee, FL 34747

  This fully FURNISHED 3 bedroom townhome in Margaritaville Resort Orlando offers one of the best opportunities to own in a DISNEY area resort that allows SHORT TERM RENTALS. Whether you are looking for a vacation home, an income producing investment, or a place to enjoy Orlando year round, this property checks every box. Located just minutes from Walt Disney World, Margaritaville Resort is one of

  Michelle Fernandez P4L REALTY LLC

  2924 Caribbean Soul Dr, Kissimmee, FL 34747
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  /29

  $449,000

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  7667 Otterspool St, Kissimmee, FL 34747

  Beautifully End-Unit Townhome in Windsor Hills! In a premier 24-hour guard-gated community! Perfect for year-round living, a vacation retreat, or a profitable short-term rental. Step inside to a bright, open-concept main floor, a kitchen with, breakfast bar, and premium appliances. The open living and dining area opens through sliding glass doors to your private screened-in pool, ideal for

  Heather Werner REAL BROKER, LLC

  7667 Otterspool St, Kissimmee, FL 34747
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  /48

  $489,000

  $61K PRICE DROP

  • 6 Beds
  • 4.5 Baths
  • 2,681 Sq Ft

  8033 Acadia Estates Ct, Kissimmee, FL 34747

  Vacation-style living starts here—this fully furnished, gated pool home delivers the space, privacy, and resort amenities today’s buyers and guests are chasing. Tucked away at the end of a tree-lined cul-de-sac in Wyndham Pointe, this impressive 6-bedroom, 4.5-bath property offers exceptional flexibility as a primary residence, second home, or high-performing short-term rental, all just minutes

  Bobby Baldor EXP REALTY LLC

  8033 Acadia Estates Ct, Kissimmee, FL 34747
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  /3

  $40,000

  $160K PRICE DROP

  • Land
  • 8.01 Acres
  • $4,994 per Acre

  0 Shelley Trail Unit MFRTB8481722, Kissimmee, FL 34747

  Read entire description Seller Financing Available. 8 Acres – OAE5 Zoning – Osceola County, FLAPN# 21-25-27-3302-0001-0070 Rare opportunity to own approximately 8 acres in unincorporated Osceola County zoned OAE5. Ideal for long-term investment, conservation use, or land banking in a growing area. The entire property is classified as wetlands and is not buildable. This property is also

  Clarence Fields FIELDS OF PROSPER LLC

  0 Shelley Trail Unit MFRTB8481722, Kissimmee, FL 34747
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  /8

  $484,999

  • 7 Beds
  • 6.5 Baths
  • 2,709 Sq Ft

  8027 Acadia Estates Ct, Kissimmee, FL 34747

  WELCOME TO 8027 ACADIA ESTATES CT! Incredible opportunity to own a 7 BEDROOM, 6.5 BATHROOM POOL HOME in the highly desirable GATED COMMUNITY OF ACADIA ESTATES, ideally located in the heart of Kissimmee’s world-famous vacation corridor! Offering approximately 2,705 SQ FT, this spacious two-story home features an exceptional bedroom and bathroom configuration with plenty of room and privacy for

  Marisol Goncalvez De Ayala AGENT TRUST REALTY CORPORATION

  8027 Acadia Estates Ct, Kissimmee, FL 34747
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  /64

  $459,900

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,564 Sq Ft

  8080 Dreamsicle Dr, Kissimmee, FL 34747

  "LAZY PARROT" is a Charming Cottage at Margaritaville Resort Orlando. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Located in PREMIUM RESORT LOCATION Just a Short Walk to All the Amenities! MRO Approved City Furniture "SAIL AWAY" Furniture/Housewares Included in List Price. Beautiful 1539-C Model, 3 Bedrooms, 3 Bathrooms with

  Suzanne Docobo EXP REALTY LLC

  8080 Dreamsicle Dr, Kissimmee, FL 34747
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  /58

  $399,000

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  7683 Fitzclarence St, Kissimmee, FL 34747

  TURNKEY WINDSOR HILLS END-UNIT TOWNHOME! This beautifully furnished 3 bedroom, 3 bathroom vacation home is located in one of the most established short-term rental resorts near Disney. The home features a private splash pool, bright end-unit layout with extra windows, tasteful furnishings, and a themed Mickey bedroom with custom wall murals and themed lighting. Recent updates include a replaced

  Andre Kressler KRESSLER REAL ESTATE

  7683 Fitzclarence St, Kissimmee, FL 34747
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  /30

  $275,000

  • 1 Bed
  • 1 Bath
  • 501 Sq Ft

  8061 Vacation Ave Unit 213, Kissimmee, FL 34747

  Own a piece of one of Orlando's most coveted resort ecosystems — the Embassy Suites by Hilton Orlando Sunset Walk, sitting at the heart of the billion-dollar Sunset Walk entertainment district.This fully furnished, turnkey condo-hotel unit is more than a vacation home — it's a revenue-generating asset backed by one of the world's most recognized hospitality brands. When you're not using it,

  Cristian Valderrama VESTI LLC

  8061 Vacation Ave Unit 213, Kissimmee, FL 34747
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  /43

  $434,000

  $21K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  2500 Renshaw St Unit 1, Kissimmee, FL 34747

  Turnkey Vacation Rental Investment in Windsor Hills Resort – Minutes from Disney World Exceptional opportunity to own a fully furnished, turnkey vacation rental in Windsor Hills Resort, one of the closest and most sought-after resort communities to Walt Disney World. This beautifully decorated, totally renovated townhome is ready for immediate rentals or personal enjoyment, with all furnishings

  Keith Courtney, Sr CHARLES RUTENBERG REALTY ORLANDO

  2500 Renshaw St Unit 1, Kissimmee, FL 34747
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  /45

  $420,000

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  7677 Fitzclarence St, Kissimmee, FL 34747

  Welcome to 7677 Fitzclarence St, a beautifully maintained and fully furnished townhome located in the highly desirable, guard-gated community of Windsor Hills Resort just minutes from Walt Disney World. This turnkey 3 bedroom, 3 bathroom home offers the perfect combination of comfort, convenience, and resort-style living, making it ideal as a primary residence, second home, or income-producing

  Heather Werner REAL BROKER, LLC

  7677 Fitzclarence St, Kissimmee, FL 34747
• 

  

  /26

  $419,000

  • 3 Beds
  • 3 Baths
  • 1,440 Sq Ft

  2530 Maneshaw Ln, Kissimmee, FL 34747

  Welcome to Windsor Hills, one of Central Florida's premier resort-style gated communities, where comfort, convenience, and investment potential come together in this beautifully furnished 3-bedroom, 3-bathroom townhome with a private pool. Whether you're searching for a vacation retreat, full-time residence, or a turnkey short-term rental investment, this home is ready to impress. Step inside to

  Veronica Figueroa EXP REALTY LLC

  2530 Maneshaw Ln, Kissimmee, FL 34747

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