Displaying: For Sale
Location: Kissimmee
Property Type(s): Single Family
Price: $500,000 to $599,000
Do Not Show Listings
Kissimmee - 277 properties found
2810 HILLIARD ISLE RD, KISSIMMEE, FL 34744
$509,00033 Days on yellowkey MLS ID: O6409970
2 Days Off yellowkey (back on 6/1/2026)
Bed: 3 Bath: 2.0 Gar: 4 Liv Area Sq Ft: 1396 Built: 1983 Tax: $6,645 (2025)Community: Valencia WoodsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,645
Elementary School: East Lake Elem
High School: Tohopekaliga High School
Tax Year: 2025
Middle School: Neptune Middle (6-8)
Remarks: Under contract-accepting backup offers. 1-acre fully gated corner lot with a 3 bedroom, 2 bathroom brick home offering endless possibilities! This well-maintained property features a spacious Florida room with A/C, cozy fireplace, and beautiful mature landscaping. The main home includes a 2-car garage plus an attached carport for additional covered parking. Recent updates include a new roof on the main house, fresh interior/exterior paint, new water heater, and new water softener system. The kitchen was remodeled in 2021 with updated finishes and functionality. A standout feature of this property is the separate standalone garage with a partially built-out framed unit and screened porch that could easily be converted into a mother-in-law suite, guest quarters, rental opportunity, workshop, or home office. This additional structure has its own separate gated entrance, offering privacy and flexibility. The fully fenced 1-acre corner lot offers exceptional space and versatility with multiple gated access points and plenty of room for boats, RVs, trailers, additional parking, or future expansion. Rare opportunity to own a property with multiple-use potential!
Listing is courtesy of: ZEFF REALTY LLC, (954-822-3912)
Listing Agent: Joshua Miller (407-399-3538)
2460 THE OAKS BLVD, KISSIMMEE, FL 34746
$560,000354 Days on yellowkey MLS ID: O6323394
5 Days Off yellowkey (back on 6/1/2026)
REDUCED by $35,000 (5.9%) on 05/12/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3416 Built: 2003Monthly Fee: $23 Tax: $455 (2024)Community: Oaks Ph 1 B1Single Family
Taxes:$455
Elementary School: Pleasant Hill Elem
High School: Liberty High
Tax Year: 2024
Middle School: Horizon Middle
Remarks: Under contract-accepting backup offers. REDUCED PRICE on this stunning 5-bedroom, Pool Home with many upgrades on a Large Corner Lot, Water Views in a Golf Community! Welcome to your dream home in the beautifully established Oaks Golf Community—one of Kissimmee’s most desirable neighborhoods. Nestled among mature trees and manicured fairways, this spacious 5-bedroom, 2 full bath, 2 half bath pool home offers 3,416 sq. ft. of luxury, comfort, and convenience. Situated on a large corner lot, the property boasts private water view and ample space for indoor and outdoor living. Inside, you’ll find a thoughtfully designed layout with recent upgrades and generous living areas. The first floor features a bedroom, Luxury Vinyl and Tile flooring throughout, and a gourmet kitchen equipped with newer 2024 stainless steel appliances. The kitchen opens to the dining room, family room, and direct access to the Great Room, perfect for entertaining guests. Upstairs, all flooring was replaced with Luxury Vinyl and upgraded baseboards. The large loft with a closet is ideal for a workout area, gaming, or a family room. The primary suite is a serene retreat with a spa-like en-suite bath featuring dual sinks and a newly tiled shower to complete fresh new look upgrade, the primary has an expansive walk-in closet with shelving. Three additional bedrooms, a large laundry room, and an upgraded guest bathroom complete the second floor. Recent upgrades include a 2025 A/C Downstairs unit, 2023 A/C Upstairs unit, 2025 Stove, 2024 refrigerator, 2024 microwave, 2024 dishwasher, 2024 dryer, 2021 Roof, 2021 Hot water heater and two new garage door openers (2024). Bathrooms have been remodeled with upgraded fixtures and tile between 2022 and 2023. Enjoy year-round outdoor living in the private screened-in pool overlooking tranquil water view, surrounded by lush landscaping. Two half baths one in the pool area and one indoors, offer convenience for family and guests. The Oaks community is a serene, amenity-rich golf community ideal for families and retirees alike. With expansive green space, championship golf, private pool homes, and proximity to both nature and city life—it delivers a perfect blend of lifestyle and convenience in the heart of Kissimmee.. Minutes from popular destinations, you can explore The Loop for shopping, dining, and movies; stroll along the Lake Tohopekaliga waterfront; or visit Shingle Creek Regional Park for kayaking, biking, and bird-watching. With easy access to US-192, John Young Parkway, and the Florida Turnpike, you’re less than 30 minutes from Orlando International Airport, Lake Nona Medical City, and Walt Disney World Resort. Whether seeking a primary residence, second home, or investment, 2460 The Oaks Blvd offers a rare opportunity to live comfortably while enjoying everything Central Florida has to offer.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Ernie Plaza, Sr (407-334-9959)
3892 GOLDEN KNOT DR, KISSIMMEE, FL 34746
$595,000111 Days on yellowkey MLS ID: V4947681
REDUCED by $25,000 (4.0%) on 04/01/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3188 Built: 2018Monthly Fee: $205 Tax: $6,943 (2025)Community: Bellalago Ph 7LSingle Family
Taxes:$6,943
Elementary School: Bellalago Charter Academy (K-8)
Middle School: Bellalago Charter Academy (K-8)
Remarks: Stunning Mediterranean-style estate located in the highly desirable, guard-gated community of Bellalago, offering timeless architecture, refined finishes, and an elevated Florida lifestyle. Conveniently located within close proximity to Walt Disney World and Universal Orlando Resort, this home allows you to enjoy world-class attractions while returning to a private and peaceful setting. This beautifully updated residence features over 3,188 square feet of thoughtfully designed living space and is ideally positioned on a quiet end street with a cul-de-sac feel, providing enhanced privacy and a serene environment. The interior features soaring ceilings, abundant natural light, and a functional layout ideal for both everyday living and entertaining. Main living areas feature travertine flooring, a wood staircase, and plantation shutters throughout. The kitchen is equipped with modern appliances, double ovens, a range hood, ample cabinetry, and a spacious pantry. All bathrooms have been tastefully renovated with clean and modern finishes. Additional interior highlights include two flexible rooms that can be easily converted into bedrooms, offices, or bonus spaces, as well as generous storage throughout the home. Plantation shutters throughout the home. Main bedroom is downstairs in addition with a guest bedroom. The exterior is equally inviting, featuring a screened balcony, screened lanai, front porch, driveway with additional parking, fenced in yard, Irrigation system, sliding doors and a corner lot. The property also includes an extended two-car garage plus an additional single garage, dual-zone A/C systems, and a well-maintained roof. Bellalago community offers resort-style amenities including 3 pools, 2 fitness centers, clubhouse, restaurant with lake views of Lake Tohopekaliga, shaded walking and biking trails, playground, tennis and basketball courts, dog park, and private boat ramp. The community provides 24/7 guard-gated security and patrol. The HOA includes fiber-optic internet and cable, reclaimed irrigation water, and trash collection. No CDD. Conveniently located near shopping, dining, and daily essentials, including Publix and Lowe's Home Improvement. This property offers a unique opportunity to enjoy comfort, privacy, and resort-style living in one of Central Florida’s premier waterfront communities. Schedule your private showing today.
Listing is courtesy of: LPT REALTY LLC (386-388-7877)
Listing Agent: Yennifer Acero, Llc (407-530-6151)
8876 CANDY PALM RD, KISSIMMEE, FL 34747
$509,00096 Days on yellowkey MLS ID: O6391761
REDUCED by $10,900 (2.1%) on 06/01/2026
Bed: 6 Bath: 5.0 Gar: 1 Liv Area Sq Ft: 3291 Built: 2012Monthly Fee: $682 Tax: $7,541 (2025)Community: Paradise Palms Resort Ph 2Single Family
Taxes:$7,541
Elementary School: None
High School: None
Middle School: None
Remarks: A fully furnished property currently operating as a successful short-term rental. Located in a prime setting with no rear neighbors, this home offers the perfect blend of privacy and modern comfort. Inside, you’ll find a beautifully maintained interior featuring no carpets, with sleek and low-maintenance flooring throughout. The open and inviting layout includes spacious living areas, a well-equipped kitchen, and comfortable bedrooms, all thoughtfully designed for guests to feel right at home. This property comes ready for its next owner, with active short-term rental bookings already in place, making it an effortless transition for those looking to step into a thriving rental opportunity or a fully furnished vacation home. Outside, the private setting and serene views create the ideal space for relaxation and enjoyment. Don’t miss your chance to own this turn-key short-term rental property—schedule your showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alexis Diaz, Pa (407-284-9980)
KISSIMMEE, FL 34746
$549,000242 Days on yellowkey MLS ID: O6354938
Bed: 6 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3512 Built: 2012Monthly Fee: $400 Tax: $8,692 (2024)Community: Bellavida Ph 1Spa: YesSingle Family
Taxes:$8,692
Remarks: After a period of strong bookings and consistent guest demand, this exceptional investment opportunity becomes available starting 05/03/2026. Inside one of Orlando's Premier Resort communities, this stunning 6-bedroom, 5.5-bath estate is designed for the family that wants it all. Walt Disney World, Universal Orlando, and SeaWorld are just minutes away. With four en-suite bedrooms, every person who walks through the door gets their own private retreat. Family, friends, or tenants, everyone feels at home. The open-concept kitchen, granite countertops, stainless steel appliances, seamless flow into the family room and breakfast nook was built for mornings that matter and evenings worth remembering. Step outside. A screened pool and covered lanai create a private outdoor space that works in every season, for every occasion. The converted garage adds dimension, game room, media lounge, creative space, home office. It adapts to whoever walks through the door. Community amenities include a 6,700 sq ft clubhouse, zero-entry pool and spa, cyber café, basketball and volleyball courts. This is not just a property. It is a decision that keeps paying you back in memories, in income, and in freedom.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Lorena Hilel (561-409-9408)
2241 RIVERGLEN CT, KISSIMMEE, FL 34746
$519,99029 Days on yellowkey MLS ID: O6410691
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3245 Built: 2017Monthly Fee: $87 Tax: $6,449 (2025)Community: Eagle Lake Ph 4BSingle Family
Taxes:$6,449
Remarks: Welcome to Eagle Lake living in the heart of Kissimmee! Nestled in a quiet cul-de-sac, this stunning two-story home offers 4 spacious bedrooms, 2.5 bathrooms, a private pool, peaceful water views, and an oversized lot that delivers the perfect blend of privacy, comfort, and endless potential. One of the home’s most unique features is its breathtaking backyard setting. The property backs up to Eagle Lake and a protected preserve that cannot be built on, offering long-term privacy and uninterrupted natural views. The preserve connects directly to beautiful Lake Tohopekaliga (Lake Toho), creating a serene and scenic backdrop that truly captures the beauty of Florida living. Inside, you’ll fall in love with the beautifully updated kitchen featuring modern finishes, ample counter space, and an open-concept layout designed for entertaining family and friends. The home also includes solar panels, helping provide energy efficiency and long-term savings for years to come. Step outside and imagine creating your own private outdoor oasis. Whether you envision an expanded screened-in lanai, outdoor kitchen, tropical landscaping, basketball court, garden retreat, or resort-style entertaining space around the pool, this oversized lot provides endless possibilities with a little imagination. Best of all, much of the hard work has already been done, allowing the next owner to simply personalize and elevate the space to fit their vision. Enjoy peaceful mornings with coffee overlooking the water, unforgettable weekend BBQs by the pool, and relaxing evenings surrounded by nature and tranquil preserve views. This home offers the rare opportunity to enjoy privacy, space, and the Florida lifestyle all in one exceptional property. Owner will consider deferred maintenance credits with the right offer.
Listing is courtesy of: W HEIRS LLC (407-680-7496)
Listing Agent: Dennis Williams (407-680-7496)
1578 CONTENTMENT LOOP, KISSIMMEE, FL 34744
$511,00035 Days on yellowkey MLS ID: S5150200
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2113 Built: 2023Monthly Fee: $7 Tax: $6,094 (2025)Community: Tohoqua Ph 3Single Family
Taxes:$6,094
Elementary School: Island Village Elementary School
High School: Gateway High School (9 12)
Middle School: Narcoossee Middle
Remarks: English
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Evelyn Galindez (407-300-1696)
2543 CHAPALA DR, KISSIMMEE, FL 34746
$550,00077 Days on yellowkey MLS ID: O6396893
REDUCED by $29,000 (5.0%) on 05/28/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4205 Built: 2002Monthly Fee: $15 Tax: $8,980 (2025)Community: Brighton Lakes Ph 1 Parcels A & GSingle Family
Taxes:$8,980
Remarks: Welcome to this stunning 5-bedroom, 4-bathroom home, perfectly situated on a generous 1/3-acre lot with no rear neighbors for added privacy. With a NEW roof, 2 NEW A/C units, and NEW laminate flooring, this home is truly move-in ready and built for comfortable, modern living. The first floor features a spacious living area just off the kitchen- ideal for gatherings and family time- as well as a breakfast nook and convenient access to a full bathroom that opens to the covered back porch. At the front of the home, you'll find a formal dining room and a versatile den or office space. The primary suite, tucked at the rear of the home for added privacy, includes sliding doors to the covered porch and a luxurious en-suite bathroom with dual sinks, a garden tub, and separate walk-in shower. Upstairs, you'll discover 4 additional bedrooms, 2 full bathrooms, and a large bonus room- perfect as a playroom, media room, or home gym. Don't miss your chance to own this beautifully updated home that combines space, functionality, and privacy in a prime location.
Listing is courtesy of: MORRIS WILLIAMS REALTY (888-326-3949)
Listing Agent: Becky Burke (352-536-4297)
831 NEPTUNE POINTE LN, KISSIMMEE, FL 34744
$585,00043 Days on yellowkey MLS ID: S5149687
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3609 Built: 2005Monthly Fee: $79 Tax: $2,354 (2025)Community: Neptune PointeSingle Family
Taxes:$2,354
Remarks: Welcome to 831 Neptune Pointe Lane, an expansive and versatile 5 bedroom, 3.5 bathroom home located in the highly desirable Neptune Pointe community. Offering an impressive 3,609 heated square feet, this is one of the largest homes in the neighborhood, perfectly positioned on one of the largest corner lots in the community. Designed with flexibility and multigenerational living in mind, the home features a highly desirable ground floor secondary primary suite complete with its own ensuite bathroom and bonus room, creating the ideal setup for an in law suite, private guest retreat, or independent living space. Inside, the spacious floor plan provides generous living areas and room to grow, while major updates including a newer roof and newer HVAC system provide added peace of mind. Step outside to enjoy the fully fenced backyard, offering privacy and plenty of room for entertaining, pets, or future outdoor enhancements. Residents of this gated community enjoy the benefits of a low HOA and no CDD, along with excellent amenities including a park, walking trail, full court basketball court, and playground. The location is truly exceptional, situated approximately half a mile from Florida's Turnpike and Highway 192, and just a short drive to NeoCity, shopping, dining, entertainment, the beach, and approximately 25 minutes from Walt Disney World. With its oversized layout, flexible living options, large corner lot, and unbeatable location, 831 Neptune Pointe Lane offers an outstanding opportunity for buyers seeking both space and convenience.
Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)
Listing Agent: Jim Mcquade (407-906-6508)
8900 PRAGUE WAY, KISSIMMEE, FL 34747
$579,000334 Days on yellowkey MLS ID: O6329265
REDUCED by $11,000 (1.9%) on 05/20/2026
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $587 Tax: $9,677 (2024)Community: Windsor At Westside Ph 3Spa: YesSingle Family
Taxes:$9,677
Elementary School: Westside K-8
High School: Celebration High
Middle School: West Side
Remarks: Welcome to this stunning 7-bedroom, 5-bathroom pool home situated on a spacious corner lot in the highly sought-after Windsor at Westside Resort. Ideal for large families, multi-generational living, or short-term rental investment, this beautifully maintained home combines comfort, style, and resort-style amenities in a gated community just minutes from Disney and major attractions. The main floor features two generously sized bedrooms, including a primary suite with direct access to the private pool. Upstairs, you'll find five additional themed bedrooms—Harry Potter, Frozen, and Star Wars—plus a large loft that has been transformed into a movie room, perfect for family entertainment. Step outside to enjoy your own screened-in private pool and spa, complete with a child safety fence, offering the ideal setting for relaxation and fun. Residents and guests enjoy full access to world-class amenities, including a lazy river, splash pad, resort-style pools, tennis courts, fitness center, arcade, on-site restaurant, and a clubhouse—all secured with 24-hour gated entry. Conveniently located off US Hwy 192 and Toll Road 429, Windsor at Westside offers quick access to shopping, dining, and the “secret” west entrance to Disney via Western Way. Whether you're searching for a vacation retreat, or a high-performing investment property, this home is move-in ready and offers exceptional value in one of Central Florida’s premier resort communities. Don’t miss your opportunity to own a piece of the magic!
Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)
Listing Agent: Veronica Li (407-674-0460)
2515 FONTAINE DR, KISSIMMEE, FL 34741
$594,900102 Days on yellowkey MLS ID: O6390540
INCREASED by $20,000 (3.5%) on 05/30/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2962 Built: 2017Monthly Fee: $288 Tax: $5,165 (2025)Community: TapestrySingle Family
Taxes:$5,165
Remarks: Wake up to serene lake views from your own private oasis within the Tapestry gated community. This 4-bedroom, 2.5-bath home combines modern elegance with the spacious outdoor living you've been dreaming about—an oversized lot provides room to entertain, expand, or simply breathe. Inside, discover a stunning loft for a home office, creative studio, or retreat space. Step onto your screened patio and unwind overlooking the lake—your personal sanctuary in the Florida sun. Master bedroom with two walk-in closets as well as a beautiful lake view. Minutes from world-class dining, premium shopping, and theme parks, yet tucked away in a peaceful neighborhood that feels like an escape.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
1545 LEAF LN, KISSIMMEE, FL 34744
$545,000103 Days on yellowkey MLS ID: O6390201
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2456 Built: 2022Monthly Fee: $134 Tax: $6,444 (2025)Community: PennyroyalSingle Family
Taxes:$6,444
Remarks: Beautiful 4-bedroom, 3-bathroom home with loft and 2-car garage located in the Pennyroyal community in Kissimmee. This Energy Star Certified home features an open-concept layout with laminate wood flooring in the main living areas. The kitchen overlooks the great room and includes 42” cabinets with crown molding, quartz countertops, stainless steel appliances, and a closet pantry. The first floor offers a convenient secondary bedroom and full bathroom, ideal for guests or a home office. Upstairs, the versatile loft provides additional living space, while the primary suite features dual walk-in closets and a bathroom with dual sinks, quartz counters, and a semi-frameless glass shower. Enjoy serene pond views from the covered lanai with pergola. Pennyroyal residents have access to a community pool with cabana, playground, and dog park. Conveniently located near Florida’s Turnpike, Lake Tohopekaliga, and Downtown Kissimmee.
Listing is courtesy of: PAK HOME REALTY (909-351-5105)
Listing Agent: Ivanna Mendoza Heredia (417-335-1572)
8908 PRAGUE WAY, KISSIMMEE, FL 34747
$529,000235 Days on yellowkey MLS ID: O6356954
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3142 Built: 2019Monthly Fee: $563 Tax: $8,764 (2025)Community: Windsor At WestsideSpa: YesSingle Family
Taxes:$8,764
Remarks: Your Private Oasis Awaits at the fantastic Windsor at Westside Resort community. Step into luxury and leisure of this fully furnished 6-bedroom, 4.5-bathroom retreat nestled in one of Central Florida’s most sought-after vacation communities. Designed for comfort and entertainment, this spacious home features a stunning loft, soaring ceilings, and an open-concept layout that seamlessly blends elegance with functionality. It features a private heated south facing pool and spa for year-round relaxation, an expansive covered lanai with sun loungers and patio seating, a gourmet kitchen with stainless steel appliances and generous counter space and a breakfast bar, dual master suites, one on each floor making it ideal for guests or multi-generational living, a converted garage game room for added fun and entertainment, and stylish finishes throughout, including ceramic tile and plush carpeting. Recent upgrades include a brand-new AC compressor and brand-new dryer. The resort features lots of great amenities including a lazy river, splash pool, clubhouse bar, fitness center, and game room. The community is guard gated and the HOA includes cable, internet, and grounds maintenance. All this and just minutes from world-famous attractions, shopping, and dining, this property offers the perfect blend of convenience and escape. Whether you're seeking a second home, a vacation getaway, or a high-performing short-term rental, this residence delivers exceptional value and unforgettable experiences.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ping Ma (863-332-0298)
8512 SUNRISE KEY DR, KISSIMMEE, FL 34747
$560,00088 Days on yellowkey MLS ID: O6388410
Bed: 7 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2881 Built: 2004Monthly Fee: $115 Tax: $6,949 (2025)Community: Emerald Island Resort Ph 4Single Family
Taxes:$6,949
Remarks: Welcome to this spacious 7-bedroom, 4.5-bathroom pool home located in the highly desirable Emerald Island Resort, one of the most sought-after short-term rental communities in the Orlando area. With nearly 2,900 square feet of living space, this home is ideal as an income-producing vacation rental or a private second home near the attractions. Designed for comfort and entertainment, the home features multiple living areas, themed bedrooms, a theater room, and a game room, offering an unforgettable experience for guests and owners alike. The private screened pool and spa provide the perfect place to relax after a day exploring Orlando. Recent updates include fresh interior and exterior paint and updated furnishings, including new living room furniture and refreshed pool patio furniture. The roof is a 2023, the pool equipment is 2025, and the HVAC units are newer and have been serviced regularly. Emerald Island Resort is a 24-hour guard-gated community offering resort-style amenities including a clubhouse, community pool and spa, fitness center, tennis and basketball courts, playgrounds, and walking trails. Ideally located just 10–15 minutes from Walt Disney World, approximately 20–25 minutes to Universal Orlando Resort and Epic Universe, and around 20 minutes to SeaWorld. Florida’s East Coast beaches such as Cocoa Beach are about an hour away, while the Gulf Coast beaches including Clearwater and St. Pete Beach are roughly 1 hour and 45 minutes away. With its prime location near shopping, dining, and major attractions, this property offers the perfect combination of investment potential and vacation lifestyle in the heart of Central Florida. BOOKING AND INCOME HISTORY AVAILABLE UPON REQUEST.
Listing Agent: Rebecca Readus (423-414-5019)
1881 NICE CT, KISSIMMEE, FL 34747
$585,00026 Days on yellowkey MLS ID: O6411765
Bed: 7 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3314 Built: 2019Monthly Fee: $606 Tax: $7,849 (2025)Community: Windsor/Westside-Ph 2ASingle Family
Taxes:$7,849
Remarks: Welcome to your dream vacation retreat in the highly sought-after Windsor at Westside Resort! This stunning 7-bedroom, 5.5-bath pool home is professionally furnished, beautifully decorated, and completely turnkey—offering everything you need for a successful vacation rental investment, a family getaway, or the perfect combination of both. From the moment you step inside, you'll appreciate the spacious open-concept layout designed for entertaining and relaxation. The fully stocked kitchen features granite countertops, abundant cabinetry, and a large island overlooking the expansive living and dining areas, making it easy to gather with family and friends after a day of fun at the parks. The first-floor primary suite offers a private retreat with direct access to the pool area through the ensuite bathroom—a thoughtful feature that's perfect after an afternoon swim. Step outside and discover your own private oasis, complete with a sparkling screened pool, relaxing hot tub, covered lanai, and the added benefit of no rear neighbors, providing a peaceful setting to enjoy the Florida sunshine year-round. Upstairs, a spacious loft serves as the ultimate entertainment hub, featuring a large-screen viewing area ideal for movie nights, gaming tournaments, or simply unwinding after an exciting day of adventure. The thoughtfully designed split-bedroom floor plan offers plenty of room for multiple families and guests, including two additional ensuite bedrooms and four beautifully themed and/or decorated guest rooms that add an extra touch of magic and fun to every stay. Located within the guard-gated Windsor at Westside Resort, owners and guests enjoy access to world-class amenities centered around the impressive 8,000-square-foot clubhouse. Enjoy dining and drinks at Tu Casa Bar & Lounge, grab essentials at the market and deli, challenge friends in the video arcade, or stay active in the fitness center. Outside, the resort truly shines with its spectacular zero-entry pool, lazy river, water playground with slides, cabanas, tiki bar, volleyball court, and playground. Even better, the HOA includes lawn care and daily valet garbage service, allowing you to spend more time enjoying the resort lifestyle and less time worrying about maintenance. Whether you're searching for a high-performing vacation rental, a second home near Disney, or a luxury retreat for family and friends, this exceptional property checks every box. Just minutes from Walt Disney World, shopping, dining, golf, and Orlando's world-famous attractions, this is your opportunity to own a piece of paradise in one of Central Florida's premier vacation home communities. Schedule your private showing today and experience the Windsor at Westside lifestyle for yourself!
Listing is courtesy of: FLORIDA RESORT REALTY LLC (863-255-2300)
Listing Agent: Danae Pitcher (863-255-2300)
2784 ROCCELLA CT, KISSIMMEE, FL 34747
$529,000214 Days on yellowkey MLS ID: O6360906
REDUCED by $20,000 (3.6%) on 05/29/2026
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 2109 Built: 2013Monthly Fee: $142 Tax: $6,297 (2024)Community: WestsideSpa: YesSingle Family
Taxes:$6,297
Remarks: Located in the highly sought-after community of Tuscany at Westside, this beautifully maintained 5-bedroom, 5-bathroom pool home offers the perfect blend of privacy, convenience, and income potential. Nestled on a cul-de-sac with no rear neighbors and serene conservation views, this fully furnished home features an open floor plan, spacious kitchen with breakfast bar, and a screened-in private pool—ideal for entertaining or relaxing. Zoned for short-term rentals and situated just minutes from Walt Disney World, Margaritaville Resort, and Sunset Walk, the location is ideal for vacationers or year-round residents. Whether you're seeking a primary residence, second home, or an income-producing investment, this move-in-ready home checks every box!
Listing is courtesy of: TRUVALOR REALTY LLC (407-218-0937)
Listing Agent: Carlos Lima Vieira, Jr (407-952-4134)
4411 WHITE OAK CIR, KISSIMMEE, FL 34746
$599,000151 Days on yellowkey MLS ID: O6376398
2 Days Off yellowkey (back on 5/28/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2271 Built: 1994 Tax: $4,844 (2025)Community: Whispering OaksSingle Family
Taxes:$4,844
Remarks: Under contract-accepting backup offers. Welcome to 4411 White Oak Cir, a beautifully renovated single-family home that truly checks every box. Updated with high-end finishes throughout, this move-in-ready property features a modern open-concept layout perfect for both everyday living and entertaining. All major upgrades have already been completed-roof, flooring, and full renovations within the last 4 years offering peace of mind and contemporary style from top to bottom SOLD FULLY-FURNISHED! The garage boasts upgraded flooring, making it ideal for a game room, home gym, or easily convertible into an additional living unit. Whether you’re looking for extra space or future income potential, the possibilities are endless. Step outside to your expansive backyard oasis featuring a screened-in heated pool, perfect for enjoying Florida living year-round. With NO HOA, you’ll have the freedom to park your boat, RV, company truck, motorcycles, ATVs, or other toys, with plenty of room to spare. Located in a prime area just 25 minutes from the Disney parks, this home is extremely desirable and offers incredible flexibility. The property is short-term rental friendly, making it a fantastic opportunity to generate income from day one, whether as a full-time investment, vacation home, or primary residence. Conveniently close to shopping, dining, entertainment, and major attractions, this home delivers luxury, location, and lifestyle all in one exceptional package. Come see this beauty for yourself, this one won’t last!
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)
Listing Agent: Daniel Araque (321-276-0747)
8622 LA ISLA DR, KISSIMMEE, FL 34747
$549,000378 Days on yellowkey MLS ID: O6314964
REDUCED by $5,000 (0.9%) on 05/28/2026
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2881 Built: 2005Monthly Fee: $107 Tax: $6,226 (2024)Community: Emerald Island Resort Ph 5ASpa: YesSingle Family
Taxes:$6,226
Remarks: Motivated seller!!! $30,000 PRICE REDUCTION!!! Welcome to your vacation oasis! Nestled in the beautiful Emerald Island Resort, this 6-bedroom pool home is a true delight. Perfectly suited for short-term rental, this property boasts a new pool heater ensuring year-round enjoyment of the pool and spa, new roof in 2024, kitchen remodel, garage converted to game ready room, new paint throughout the home, all new smart televisions. . Currently in a rental pool with strong reservations, the projected revenue for 2025 exceeds $50,000, providing an attractive investment opportunity. Future reservations that are strong through October can stay with the home with continued use of current management company. The tastefully decorated interiors provide a clean slate for you to infuse your own magic touch. Home is loaded with potential! All furnishings will remain, facilitating a smooth transition. Owners and guests alike enjoy access to the resort's premier amenities, including 2 heated outdoor pools, a spa, dry sauna, fitness center, Tiki Bar, volleyball court, tennis, basketball & pickleball court, arcade, 2 playgrounds, and 11 acres of nature trails! Conveniently located with quick access to major theme parks, especially Disney World, being just 10 minutes away, this
Listing is courtesy of: EPIC FLORIDA REALTY LLC (407-553-3313)
Listing Agent: Casey Hatfield (407-473-6921)
4548 YORKSHIRE LN, KISSIMMEE, FL 34758
$550,000109 Days on yellowkey MLS ID: S5145086
2 Days Off yellowkey (back on 5/27/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2053 Built: 1991 Tax: $5,034 (2025)Community: Country Side ManorSpa: YesSingle Family
Taxes:$5,034
Remarks: Under contract-accepting backup offers. Welcome to this STUNNING 4 bedroom, 2.5 bath POOL home nestled in the charming Country Side Manor Community. Perfectly positioned on a beautifully landscaped 0.60-acre lot with no rear neighbors, this FULLY RENOVATED gem offers privacy, space, and exceptional upgrades throughout. Step inside to an inviting open-concept living area filled with natural light and adorned with gorgeous tile flooring that flows seamlessly throughout the home. The heart of the home, the kitchen, is designed to impress, featuring a spacious center island perfect for gathering, elegant QUARTZ countertops, soft-close cabinetry, a complimenting backsplash, and brand new stainless steel appliances. Enjoy casual mornings in the cozy breakfast nook overlooking the sparkling pool, or host memorable dinners in the more formal dining space made for special occasions. Just off the kitchen, a versatile bonus living area provides endless possibilities from a family room to a home office, playroom, or den, tailored to fit your lifestyle. The thoughtfully designed split-bedroom floor plan offers privacy and comfort. The primary suite is a true retreat, complete with French doors leading to the pool area, a walk-in closet, and a beautifully updated en-suite bath featuring dual vanities and a large walk-in shower. Step outside to your own private oasis, as the screened pool and spacious covered lanai create the ultimate setting for entertaining, from summer BBQs to birthday celebrations or simply relaxing in the Florida sunshine. Storage and functionality abound with a MASSIVE 50x30 steel building offering endless potential, workshop, RV or boat storage, home business space... PLUS an additional 10x12 shed for even more convenience. This home is truly move-in ready, just bring your belongings and your toys. Don’t miss your opportunity to own this exceptional property that blends modern upgrades, outdoor living, and peaceful surroundings.
Listing is courtesy of: CENTURY 21 ALL HOMES & PROPERT (407-343-1300)
Listing Agent: Natalie Feldman (407-574-1915)
3086 WHITE HORSE CT, KISSIMMEE, FL 34746
$545,00052 Days on yellowkey MLS ID: O6403738
REDUCED by $30,000 (5.2%) on 05/25/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2166 Built: 2015Monthly Fee: $213 Tax: $8,737 (2025)Community: Storey LakeSingle Family
Taxes:$8,737
Elementary School: Floral Ridge Elementary
Middle School: Kissimmee Middle
Remarks: Welcome to this well-maintained Eastham II floor plan located in the gated community of Storey Lake. This 4-bedroom residence offers a functional split-bedroom layout with spacious living areas and multiple full bathrooms designed for privacy and convenience. The main living area features an open-concept kitchen, dining, and living room combination with abundant natural light. The kitchen includes professionally painted cabinetry with soft-close upgrades, stainless steel appliances, a custom pantry, granite countertops, and a large quartz center island with seating for up to 4 people. The adjacent dining area offers flexible use as a formal dining space, home office, or additional living area. The primary suite is privately positioned toward the rear of the home and features luxury vinyl flooring, a tray ceiling, walk-in closet, and an en-suite bathroom with dual vanities, garden tub, and separate walk-in shower. A secondary access point to the laundry room adds practical functionality. Outdoor features include a covered patio area overlooking a fenced backyard with no rear neighbors. The extended brick paver patio includes a motorized retractable awning and vertical screen, providing additional usable outdoor living space. Please note, there is no screened patio/enclosure. Additional features include a 2-car garage with ceiling-mounted storage, whole-house water filtration system, and HVAC updates, with the interior unit replaced in 2023 and exterior unit replaced in 2020. Storey Lake offers gated access and community amenities including a pool, fitness center, parks, and recreational areas. The property is conveniently located near major highways, shopping, dining, and Central Florida attractions.
Listing is courtesy of: NORKIS & CO REALTY (407-506-7070)
Listing Agent: Jose Santana Feliciano (407-760-9090)
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