Kissimmee Homes For Sale & Real Estate - 2572 homes

Remarks: Discover an excellent vacation rental investment in the highly desirable resort-style, guard-gated community of Windsor Palms. This 2-bedroom, 2-bath, First Floor condo is just minutes from Disney Theme Parks and Orlando’s most popular attractions, making it a high-demand option for short-term rentals or personal use. Fully furnished and ready to move in. The building received fresh exterior paint in 2025. HOA fees cover water, trash, internet, and cable, so the owner only pays for electricity. Inside, this First Floor condo offers a bright, open layout with comfortable living and dining space, a fully equipped kitchen, an in-unit washer and dryer, and a screened lanai that is perfect for relaxing after a day at the parks. The primary suite includes a private ensuite bathroom, and the second bedroom and bathroom work well for family or guests. The condo also has new windows throughout, installed in 2025. Plank flooring throughout. Fully Furnished. No stairs, handicap accessible. Condo is close to parking area. Windsor Palms is a well-established vacation rental community with no usage restrictions. You can use the property as a primary home, second home, long-term rental, or short-term rental through platforms like Airbnb or VRBO. Owners are free to choose any property management company, which makes hands-off ownership very easy. Residents and visitors enjoy a full range of resort-style amenities, including a clubhouse, large community pool, fitness center, tennis courts, playground, basketball court, volleyball court, movie theater, and a convenience store. These features help keep rental demand strong. The location is close to Disney Theme Parks, Margaritaville Resort, shopping, dining fine and casual, and major roads such as US-192, I-4, and SR-429. Easy access from airport either via Freeway or Toll road. This condo offers an excellent mix of location, flexibility, and long-term investment value.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Larysa Tsyupenko (407-780-5456)

Remarks: Beautiful Condo in Prime Kissimmee Location! - Welcome to 2848 Osprey Cove Pl, Apt 204, Kissimmee, FL 34746, a charming and well-maintained condo ideal as a primary residence, vacation home, or investment opportunity. This spacious 3-bedroom, 2-bathroom villa-style condo offers 1,136 sq ft of heated living space and 1,221 sq ft total area, featuring a comfortable one-story layout built in 2000 with a heating/cooling pack A/C system. The unit provides a functional floor plan with great natural light and inviting living areas that make it perfect for both personal use and rental potential. - Located in a highly desirable area of Kissimmee, the property is just minutes from Walt Disney World and other major theme parks, as well as shopping centers, restaurants, golf courses, and everyday conveniences. It offers easy access to US-192, I-4, and other major highways, making commuting and exploring Central Florida effortless. Its proximity to Orlando International Airport adds even more convenience for homeowners and short-term rental investors. - Don’t miss this opportunity to own a well-located condo in the heart of Central Florida, close to world-famous attractions and everything the area has to offer. Schedule your showing today!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Viviana Arias (760-313-9240)

Remarks: Welcome to this well-maintained 3-bedroom, 2-bath home located in the desirable gated community of Cypress Bay. Featuring a new A/C, an open and functional layout, and spacious bedrooms, this home offers both comfort and convenience. Enjoy living just minutes from major shopping, dining, schools, and everything Kissimmee has — all within a secure, beautifully kept neighborhood. This is the perfect opportunity for a first-time buyer, downsizer, or investor looking for a solid home in a prime location.

Listing is courtesy of: EXP REALTY LLC (407-846-0940)

Listing Agent: Antonio Fuentes, Jr (407-288-5182)

Remarks: Welcome to this 4-bedroom, 2-bathroom home nestled on a cul-de-sac in Poinciana Villages! Situated on an oversized .35-acre lot, this property offers a fully fenced yard—perfect for outdoor living, pets, or entertaining. Step inside to an inviting open floor plan featuring a seamless flow between the living and dining areas, ideal for both everyday living and hosting guests. The kitchen is a true centerpiece, complete with stone countertops, stainless steel appliances, and a cozy eat-in area. Vaulted ceilings enhance the sense of space and natural light throughout the home. The split-bedroom layout provides privacy and functionality, with the spacious primary suite tucked away at the rear of the home, offering a peaceful retreat with a full en-suite bathroom. Three additional bedrooms are located near the front of the home, along with a second full bathroom—perfect for family or guests. Located in the desirable Poinciana Villages community, residents enjoy access to an array of amenities including parks with boating ramps, picnic areas, hiking trails, fitness facilities, an aquatic center, event center, and two community pools—all included in the HOA. You’ll also love being just minutes from shopping, dining, medical facilities, and the scenic Disney Wilderness Preserve. This immaculate home combines comfort, convenience, and lifestyle—schedule your private showing today!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Veronica Figueroa (407-519-3980)

Remarks: This 3 bedroom/1 bath single family home offers 1,410 sq ft of living space on a 0.08 acre lot with a functional layout and recent upgrades throughout. The kitchen features wood cabinetry, stainless steel appliances, a pantry corner, and tile flooring, while the living area also offers tile floors for easy maintenance. Bedrooms are carpeted, and custom cabinetry provides added storage. A dedicated laundry area adds convenience, and the covered front patio doubles as a sunroom for additional usable space. The property is fully fenced and wired, with a carport, mini storage shed, outbuilding, and a DIY outdoor utility table. The wide backyard offers room for expansion or added value. Major improvements include foundation work, plumbing updates, new windows, and appliances, making this a solid, move-in ready option with strong rental or resale potential.

Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)

Listing Agent: Scott Fader (248-294-7850)

Remarks: Escape to your own slice of paradise with this beautiful corner unit at Margaritaville Resort Orlando. Fully furnished and move-in ready, this home blends modern comfort with a laid-back tropical vibe. Just 10 minutes from Disney, you’ll enjoy the perfect mix of convenience and tranquility. Inside, the open layout is ideal for both relaxing getaways and hosting friends, while the spacious, contemporary kitchen makes cooking and gathering a true pleasure. As part of this sought-after resort community, you’ll have access to incredible amenities including a full-service spa, multiple resort-style pools, on-site dining, and the lively atmosphere that makes Margaritaville so special. Whether you’re searching for a smart investment, a vacation retreat, or a full-time residence, this property offers it all—right in the heart of the magic. Don’t miss the chance to call this tropical haven your own!

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Vanessa Scotland, Pa (407-217-4580)

Remarks: OVER QUARTER ACRE LOT -- MOVE IN TODAY! Welcome to the "Cypress" model by Honesty Homes! Open-concept, concrete block home features high-end finishes and numerous upgrades throughout. You'll find 42" cabinets in the kitchen and bathrooms, sleek granite countertops perfect for culinary creativity, and soaring vaulted ceilings that enhance the sense of space. The master bedroom offers indulgence with its vaulted ceiling and two spacious walk-in closets for ample storage. Both bathrooms are thoughtfully designed with generously sized tubs and modern tiled showers, ideal for relaxation. Schedule your showing today! BUILDER INCENTIVES TOWARDS CLOSING COSTS OR BUYING DOWN THE RATE FOR USING PREFERRED LENDER

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Amer Lababidi (407-800-3631)

Remarks: Welcome to Tuscany Preserve, a private gated community offering resort-style living. This beautifully maintained 2-bedroom, 2-bathroom villa is part of a charming quadplex with a timeless Spanish-style tile roof that enhances the community’s character. Inside, the home features ceramic tile throughout, 42” cabinets, granite countertops, and stainless steel appliances, creating a clean, modern feel with low-maintenance living. Residents of Tuscany Preserve enjoy access to premium amenities, including a clubhouse, fitness center, resort-style pool, tennis courts, and basketball courts. The HOA also includes high-speed internet and cable, making everyday living both convenient and cost-effective. This property offers flexibility for both homeowners and investors, as short-term rentals and Airbnbs are allowed. Conveniently located and move-in ready, this villa is a great opportunity to own in one of the area’s most amenity-rich communities. FHA and VA financing approved!

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Amer Lababidi (407-800-3631)

Remarks: MOVE IN TODAY - Honesty Home Builders presents brand-new 2-bedroom, 2-bathroom villas in Tuscany Preserve, a private gated community. These modern quadplex villas boast Spanish-style Tiled roofs, adding timeless charm to the community’s exterior. These modern quadplex villas feature ceramic tile throughout, 42” cabinets, granite countertops, and state-of-the-art stainless steel appliances. Tuscany Preserve provides exclusive amenities including a private gym, clubhouse, pool, tennis and basketball courts. Each home owner has high-speed internet and hundreds of TV channels covered by the association, life here is effortless! All financing options accepted: FHA, VA, and Conventional. Ask about the builder's preferred lender and closing cost incentives. Short-term rentals and Airbnbs are allowed!

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Amer Lababidi (407-800-3631)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home offering impressive curb appeal and a warm, inviting layout. Step inside to a light-filled, open design where the living, dining, and kitchen spaces flow naturally together—perfect for both everyday comfort and entertaining. The grand foyer sets the tone, leading to a formal dining room conveniently located beside the well-appointed kitchen, complete with ample cabinetry, stainless steel appliances, and a roomy closet pantry. The primary suite provides a bright, airy retreat with a spacious bathroom featuring dual vanities. Additional highlights include a large oversized garage, a charming front porch, and a fully fenced backyard ideal for outdoor enjoyment. This is truly a home worth seeing—schedule your showing and experience its charm for yourself.

Listing is courtesy of: EXP REALTY LLC (407-846-0940)

Listing Agent: Steve Pugh (407-846-0940)

Remarks: MOVE IN TODAY - Honesty Home Builders presents brand-new 2-bedroom, 2-bathroom villas in Tuscany Preserve, a private gated community. These modern quadplex villas boast Spanish-style Tiled roofs, adding timeless charm to the community’s exterior. These modern quadplex villas feature ceramic tile throughout, 42” cabinets, granite countertops, and state-of-the-art stainless steel appliances. Tuscany Preserve provides exclusive amenities including a private gym, clubhouse, pool, tennis and basketball courts. Each home owner has high-speed internet and hundreds of TV channels covered by the association, life here is effortless! All financing options accepted: FHA, VA, and Conventional. Ask about the builder's preferred lender and closing cost incentives. Short-term rentals and Airbnbs are allowed!

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Amer Lababidi (407-800-3631)

Remarks: MOVE IN TODAY - Honesty Home Builders presents brand-new 2-bedroom, 2-bathroom villas in Tuscany Preserve, a private gated community. These modern quadplex villas boast Spanish-style Tiled roofs, adding timeless charm to the community’s exterior. These modern quadplex villas feature ceramic tile throughout, 42” cabinets, granite countertops, and state-of-the-art stainless steel appliances. Tuscany Preserve provides exclusive amenities including a private gym, clubhouse, pool, tennis and basketball courts. Each home owner has high-speed internet and hundreds of TV channels covered by the association, life here is effortless! All financing options accepted: FHA, VA, and Conventional. Ask about the builder's preferred lender and closing cost incentives. Short-term rentals and Airbnbs are allowed!

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Amer Lababidi (407-800-3631)

Remarks: Honesty Home Builders presents brand-new 2-bedroom, 2-bathroom villas in Tuscany Preserve, a private gated community. These modern quadplex villas boast Spanish-style Tiled roofs, adding timeless charm to the community’s exterior. These modern quadplex villas feature ceramic tile throughout, 42” cabinets, granite countertops, and state-of-the-art stainless steel appliances. Tuscany Preserve provides exclusive amenities including a private gym, clubhouse, pool, tennis and basketball courts. Each home owner has high-speed internet and hundreds of TV channels covered by the association, life here is effortless! All financing options accepted: FHA, VA, and Conventional. Ask about the builder's preferred lender and closing cost incentives. Short-term rentals and Airbnbs are allowed!

Listing is courtesy of: THE FIRM RE (407-227-3345)

Listing Agent: Amer Lababidi (407-800-3631)

Remarks: Welcome to this beautiful home located in the highly desirable Bella Vida Resort, one of Kissimmee’s most sought-after gated communities. This elegant property offers a perfect blend of comfort, style, and convenience, making it ideal as a primary residence, vacation home, or investment opportunity. The home features spacious living areas filled with natural light, a thoughtfully designed floor plan, and a private outdoor space perfect for relaxing or entertaining. The kitchen is well appointed with modern finishes and ample cabinet space, seamlessly connecting to the dining and living areas. Step outside to enjoy your private screened-in pool, creating the perfect setting to unwind after a day exploring Central Florida. Residents and guests of Bella Vida enjoy resort-style amenities including a clubhouse, resort pool, fitness center, playground, walking trails, and beautifully maintained green spaces. The community is conveniently located just minutes from Disney World, shopping, restaurants, and major highways, offering both tranquility and easy access to everything Orlando has to Provide. Whether you are looking for a vacation retreat or a profitable short-term rental investment, this property presents an exceptional opportunity in the heart of Central Florida.

Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)

Listing Agent: Bruna Sereno (407-883-6648)

Remarks: Fully renovated and move-in ready 3-bedroom, 2-bath condo located in the desirable Gables at Lakeside community. This spacious second-floor unit offers a private entrance and peaceful pond views, creating the perfect setting to relax and unwind. Inside, you’ll find a bright and open layout with modern updates throughout, providing comfort and functionality for everyday living. The community features excellent amenities including a swimming pool, fitness center, tennis court, clubhouse, playground, and more — all within a quiet and well-maintained environment. Conveniently located in the heart of Kissimmee, just minutes from shopping, dining, major roadways, and The Loop. Whether you’re looking for a primary residence or an investment opportunity, this property offers both value and location. Schedule your private showing today.

Listing is courtesy of: CAINAN BA LLC (407-724-4173)

Listing Agent: Cainan Almeida (407-724-4173)

Remarks: Under contract-accepting backup offers. Short Sale. Short Sale – Home with Great Potential! Welcome to this 5-bedroom, 3.5-bath custom home on 2.38 private acres at the end of a secluded dead-end street. This property offers the perfect mix of space, privacy, and opportunity. Enjoy outdoor living with a pool, covered porch, and outdoor kitchen—ideal for entertaining. A 4-car garage with attached workshop and plenty of space for RVs, boats, and trailers makes this home perfect for hobbyists and adventurers alike. Inside, you’ll find a spacious kitchen with matte granite countertops, Wolf appliances, Sub-Zero fridge, and travertine flooring. Custom touches include tongue-and-groove Aspen ceilings, Pecky Cypress wood accents, and cedar-lined closets. The space above the garage, was used as a gym, offers flexibility, convert it into a rental, guest suite, or office. While the well is not currently working, this property is filled with potential to be transformed into your dream retreat.

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III REALTY (407-207-0825)

Listing Agent: Jessica Estrada (863-409-1771)

Remarks: Price Improvement! Enjoy a spacious and open floor plan featuring access to the oversized screened lanai with a heated hot tub and tranquil water views—perfect for relaxing and entertaining. The home includes first-floor laundry, a powder room, a primary bedroom with an ensuite bath, and a guest room, offering comfort and convenience. This stunning upgraded deluxe townhome is an investment opportunity in the highly sought-after gated community of Regal Oaks at Old Town. With professional property management already in place, it offers a hassle-free ownership experience and rental potential. Please note, this property is specifically tailored for investors seeking a rental asset. Located adjacent to Old Town and just a ten-minute drive to Walt Disney World Resort, this home combines a prime location with rental income prospects. The management team provides comprehensive services, including marketing, property upkeep, guest check-ins, thorough cleaning, communication, licensing, tourist taxes, insurance, and ongoing maintenance. The office is conveniently situated within the Clubhouse premises, ensuring seamless support and oversight. Additional support includes assistance with financial statements, current market analysis, and insights into the State of the Market, empowering you to make informed investment decisions. Don’t miss this opportunity to grow your real estate portfolio with a beautifully upgraded, professionally managed rental home in a prime Florida location. Contact us today to learn more!

Listing is courtesy of: IDILIQ ESTATES USA LLC (407-997-1000)

Listing Agent: Christine Butler (407-908-1923)

Remarks: Located just 25 minutes from Disney!!! This beautiful Mediterranean-style 4 Bedroom, 3.5 Bath home in the gated Brighton Lakes community offers 4,198 sq ft of living space. This rare property includes a multi-generational living area and three full kitchens with all appliances—ideal for extended family or flexible use. Interior features include imported Mahogany hardwood floors, an open floor plan, and a spacious master suite with double walk-in closets and a spa-style bath with a jacuzzi tub. The covered lanai provides a peaceful water view, perfect for relaxing or entertaining. Conveniently located near shopping, dining, and major conveniences. Lender credit available with seller’s preferred lender.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Virginia Doherty (321-374-0213)

Remarks: Don't miss this two-story duplex on a corner lot in Historic Downtown Kissimmee! Walking distance to SunRail Station, public transportation, stores, restaurants, and Kissimmee Lakefront Park. Renovated in 2023 with new 30-year architectural shingle roof. Downstairs unit (116): Owner-occupied, ~300 sq ft larger than upstairs, 2 beds (configurable as 3), 1 bath, covered front/back porches, carpet/tile floors, eat-in kitchen, interior washer/dryer hookups, covered carport; potential rent $1600+/month. Upstairs unit (118): Rented $1500/month + $50 water, 2 beds, 1 bath, plus versatile third room (living/family or 3rd bedroom) with balcony access, washer/dryer hookups and storage off covered carport. Two electric meters (tenants pay own); one water meter (landlord pays). Updates: Water heater and A/C replaced 2019; re-wired, re-piped, doors/windows/insulation replaced 2019. Each unit has its own fenced yard; backyard includes concrete pad and 12x20 storage shed. Convertible to 5-bedroom home via locked-off doorway from downstairs to upstairs stairway; ideal for short-term rental/Airbnb. Ample rear land offers potential for third unit or ADU; zoned T4-O, future land use MU-D (Downtown Mixed Use).

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Judson Osbon (407-955-1672)

Remarks: Pool Home Just Minutes from Disney & Margaritaville! Welcome to 2823 Drifting Lilly Loop, a 3-bedroom, 2-bathroom pool home located in the highly sought-after Oak Island Cove community—just 3 miles from Walt Disney World and the vibrant Margaritaville Resort. Whether you're searching for a primary residence, investment opportunity, or a high-performing short-term rental, this home checks all the boxes. Step inside to an impressive foyer that opens into a bright, airy living space with vaulted ceilings, ceramic tile flooring, and an abundance of natural light. The open-concept kitchen, dining, and living room create the perfect layout for entertaining or relaxing with family. The spacious primary suite offers private pool access, a walk-in closet, and a luxurious en-suite bathroom featuring a spa/jacuzzi tub. Two additional bedrooms are thoughtfully situated on the opposite side of the home, ensuring privacy for guests or family, and are served by a full guest bath. Sliding glass doors lead out to your private oasis—a covered lanai and screen-enclosed heated pool and spa with an extended deck, ideal for year-round enjoyment. Highlights Include: Newer AC system & pool pump, & Low HOA fees, Located just off Highway 192, you’re minutes from world-class shopping, dining, and entertainment at Sunset Walk, plus easy access to major highways and all of Central Florida’s top attractions. With new developments and attractions continually emerging, this home puts you at the center of it all.

Listing is courtesy of: PREMIUM PROPERTIES REAL ESTATE (407-380-2800)

Listing Agent: Tj Connor (407-340-8385)