Location: Kissimmee , 34744
Do Not Show Listings
237 STRATHMORE CIR, KISSIMMEE, FL 34744
$424,90071 Days on yellowkey MLS ID: O6403214
REDUCED by $10,100 (2.3%) on 06/11/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2278 Built: 1999Monthly Fee: $18 Tax: $4,632 (2025)Community: Remington Ph 1 Tr BSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,632
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Buyer's Welcome, All Offers Considered! ***This also includes assisting Buyers with costs and fees! *** Set within the tree-lined streets of the Remington Golf Community, this 4-bedroom, 2-bath home welcomes you with a layout that feels open, comfortable, and easy to settle into. The foyer leads into connected living and dining spaces that flow effortlessly from one room to the next, offering plenty of room for gathering, relaxing, or finding a quiet corner of your own. The kitchen sits at the center of it all, allowing conversations to move naturally throughout the home. The split-bedroom design places the primary suite in its own peaceful wing, complete with a walk-in closet and private bath. Three additional bedrooms offer flexibility for guests, work, or hobbies. Just beyond the main living areas, a large, screened patio becomes an extension of the home — a place where you can unwind in the shade, listen to the breeze move across the fairway, and imagine watching the sunset settle over the golf course at the end of the day. Life in Remington comes with access to a championship golf course, community pool, fitness center, tennis courts, and walking paths, creating an environment where staying active and enjoying the outdoors feels effortless. The location adds even more convenience, with everyday shopping, dining, and services just minutes away along East Irlo Bronson Memorial Highway. Larger destinations such as The Loop, Lake Nona, and Orlando International Airport are also within easy reach. A welcoming layout, a community full of amenities, and a setting that lets you enjoy the beauty of the fairway from your own patio — all waiting for you at 237 Strathmore Circle.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Jonathan Speagle (217-521-1866)
1941 PARTIN TERRACE RD, KISSIMMEE, FL 34744
$514,400137 Days on yellowkey MLS ID: O6386096
REDUCED by $5,000 (1.0%) on 07/09/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2787 Built: 2019Monthly Fee: $11 Tax: $3,624 (2025)Community: Kindred 100 RepSingle Family
Taxes:$3,624
Elementary School: Neptune Elementary
High School: Gateway High School (9 12)
Middle School: Neptune Middle (6-8)
Remarks: IN-LAW suite with separate entrance; includes its own kitchenette and full bathroom—ideal for multigenerational living or guests. Beautiful move-in-ready home featuring 4 bedrooms, 3.5 baths, and the highly sought-after Camden floor plan with a private in-law suite and its own separate entrance. The main living area offers a bright, open kitchen with granite countertops, custom backsplash, and a water filtration system. Tile and luxury vinyl plank flooring flow throughout the home. A built-in entertainment center with an electric fireplace adds a warm, modern touch. The spacious bonus room is perfect for a home office, hobby room, or additional flex space. Additional upgrades include: • Smart-home technology • Extensive camera system (some cameras convey) • Renovated attic with custom electric lift • Whole-home water softener • Ceiling fans in every room • Custom wine cabinet with extra storage Enjoy access to three clubhouses, three resort-style pools, two fitness centers, miles of scenic nature trails, playgrounds, and a dog park—all with a LOW HOA. Enjoy indoor-outdoor living in the large, enclosed Florida room, leading out to a beautiful paver patio overlooking breathtaking sunset views, rocket launches can even be seen from the backyard. Enjoy the expansive view of the wildlife preserve. The large corner lot features gated rear access, plus a covered shed for added storage.
Listing is courtesy of: GULFSTREAM REALTY GROUP (407-252-6775)
Listing Agent: Scott Kennedy (407-252-6775)
1115 PROSPERITY AVE, KISSIMMEE, FL 34744
$469,000116 Days on yellowkey MLS ID: S5146235
REDUCED by $5,000 (1.1%) on 06/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2085 Built: 2003Monthly Fee: $46 Tax: $2,454 (2025)Community: Fortune LakesSpa: YesSingle Family
Taxes:$2,454
Elementary School: Mill Creek Elem (K 5)
High School: Osceola High School
Remarks: Welcome to this spacious 4-bedroom, 2-bath single-family home featuring a beautiful saltwater pool, located in the desirable Fortune Lakes community of Kissimmee. Built in 2003, this well-maintained property offers 2,085 sq ft of living space on an 8,233 sq ft lot, providing comfort, privacy, and convenience in a prime Central Florida location. This home features a split floor plan, generous living areas, and a layout ideal for both everyday living and entertaining. Recent upgrades include central A/C (2020), water heater (2024), new kitchen appliances, updated kitchen countertops, new carpet and flooring, and a wireless alarm system on all doors and windows. The home also offers a new roof, recently resurfaced pool and pool deck, an upgraded screened enclosure, and a saltwater pool system with a pool pump replaced approximately 2–3 years ago. Exterior features include a 2-car garage, stucco finish, and composition shingle roofing. Located just minutes from major highways, shopping, dining, schools, and medical facilities, this home provides excellent access to everything Kissimmee and Orlando have it. The Fortune Lakes/Remington area is known for its well-kept surroundings, nearby golf options, and strong community appeal. Original Owners.
Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Jackie San Pedro (407-346-8922)
1989 SPRING SHOWER CIR, KISSIMMEE, FL 34744
$400,000180 Days on yellowkey MLS ID: O6371277
REDUCED by $15,000 (3.6%) on 07/09/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2087 Built: 2023Monthly Fee: $136 Tax: $7,473 (2025)Community: Tohoqua ReserveSingle Family
Taxes:$7,473
Remarks: Welcome to 1989 Spring Shower Circle, a beautifully appointed 3-bedroom, 2-bath residence nestled within TOHOQUA RESERVE one of Kissimmee’s premier 55+ communities! This GATED community is nearing completion, offering the perfect balance of a fresh, newer neighborhood feel without the disruption of long-term construction. Designed with both comfort and style in mind, this thoughtfully crafted home features a versatile flex room—perfect for a private office, creative studio, or cozy den. At the heart of the home, the chef-inspired kitchen impresses with a sprawling island, abundant cabinetry, gleaming quartz countertops, stainless steel appliances, and a generous walk-in pantry—ideal for both entertaining and everyday living. The open-concept layout seamlessly connects the kitchen, dining, and living areas, creating a light-filled, inviting space perfect for gatherings or quiet evenings at home. The spacious primary suite offers a peaceful retreat, complete with a well-appointed en-suite bath and an oversized walk-in closet. Secondary bedrooms provide comfortable accommodations for guests or additional living flexibility. Step outside your front door and embrace a lifestyle that goes far beyond the home. This vibrant, amenity-rich ACTIVE ADULT community is designed for connection and activity, featuring a stunning clubhouse, resort-style pool and spa, fire pits, state-of-the-art fitness center, scenic walking trails, and a variety of recreational options including pickleball, tennis, bocce ball courts, and a dog park. Residents also have access to Tohoqua's amenities outside the reserve, including another resort style pool. Ideally located within proximity to major roadways, including US-192 and the FL. Turnpike and is within 30 minutes of Orlando International Airport, Orlando’s world class amusement parks, and Medical City. This home delivers the perfect balance of peaceful, established living and everyday convenience.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Jean Scott (407-759-5320)
1810 N BRACK ST, KISSIMMEE, FL 34744
$250,0008 Days on yellowkey MLS ID: O6422750
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 816 Built: 1962 Tax: $1,589 (2024)Community: Robert Bass AddSingle Family
Taxes:$1,589
Elementary School: Central Avenue Elem
Tax Year: 2024
Middle School: Denn John Middle
Remarks: Located in Downtown Kissimmee so you can walk to stores and restaurants. Convenient to everything… Newly renovated inside and outside New roof and granite countertops, new flooring, new paint inside and outside, new appliances W/D, Dishwasher, Fridge plus newly fenced all around the property line Welcome to 1810 Brack St, a charming house located in the heart of Kissimmee, FL. This property accords a wonderful opportunity to enjoy Florida living. The exterior of the home features a classic design with well-maintained landscaping that enhances its curb appeal. Large windows throughout the house allow for ample natural light, creating a warm and inviting atmosphere inside. The property provides a spacious layout that is versatile for various living arrangements. With its convenient location, residents can easily access local amenities and attractions that Kissimmee has to accord. This home presents an excellent opportunity for those seeking a residence in a vibrant community. Discover the potential of this property and envision the possibilities for your future here at 1810 Brack St. Property is Sold As Is
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
1869 KINGS POINT BLVD, KISSIMMEE, FL 34744
$410,0004 Days on yellowkey MLS ID: O6424293
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1704 Built: 1983 Tax: $2,073 (2025)Community: Kings PointSpa: YesSingle Family
Taxes:$2,073
Remarks: Nestled on a fully fenced 0.346-acre lot with NO HOA, this well-maintained 3-bedroom, 3-bath home offers the perfect blend of space, flexibility, and thoughtful updates. Significant improvements include a new roof (2025), new HVAC system (2025), updated windows and sliding glass doors (approximately 2021), and an Energy Smart 50-gallon water heater. Public water and sewer provide added convenience, while a sump pump enhances the functionality of the home's lower level. Inside, you'll find spacious living areas, generously sized bedrooms, large walk-in closets, an oversized pantry, and an interior laundry room. The screened front porch and private deck accessed from the primary bedroom create inviting spaces to relax and enjoy the peaceful surroundings. One of the home's most distinctive features is the full, unfinished basement with exterior access, providing exceptional flexibility for a workshop, hobby area, fitness space, storage, or other uses to fit your lifestyle. Buyers should verify intended use and applicable requirements. The oversized 2.5-car garage provides ample room for vehicles, recreational equipment, or boat storage. Outside, the fully fenced backyard provides plenty of space to enjoy Florida living, complete with a hot tub and generous parking for a boat, RV, or other recreational vehicles without HOA restrictions. Combining major system updates, abundant storage, flexible workspace, and room for recreational pursuits, this home offers exceptional versatility. Conveniently located just minutes from Lake Tohopekaliga (Lake Toho), its waterfront parks and recreational opportunities, historic downtown Kissimmee, the Florida Turnpike, The Loop shopping and dining, and everyday conveniences, this home offers both accessibility and a quiet residential setting.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Dagmara Krupa (570-952-1350)
192 WESTMORELAND CIR, KISSIMMEE, FL 34744
$430,0004 Days on yellowkey MLS ID: S5153506
0 Days Off yellowkey (back on 7/10/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2285 Built: 1997Monthly Fee: $14 Tax: $3,379 (2025)Community: Remington Ph 1 Tr FSingle Family
Taxes:$3,379
Remarks: For Input Purposes Only. Welcome to this spacious 4-bedroom, 2.5-bath pool home offering the perfect blend of comfort, functionality, and Florida living. Inside, you'll find a thoughtfully designed floor plan with generous living spaces, a well-appointed kitchen, and plenty of room for both everyday living and entertaining. The primary suite provides a private retreat with an en-suite bathroom, while the additional bedrooms offer flexibility for family, guests, or a home office. Step outside to your own backyard oasis featuring a screen-enclosed swimming pool, perfect for relaxing, entertaining, or enjoying Florida's year-round sunshine. Conveniently located near shopping, dining, schools, major roadways, Orlando International Airport, and Central Florida attractions, this home offers both comfort and convenience.
Listing is courtesy of: EXP REALTY LLC (407-846-0940)
Listing Agent: Steve Pugh (407-846-0940)
28 LINDA LN, KISSIMMEE, FL 34744
$470,0004 Days on yellowkey MLS ID: O6422948
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1745 Built: 1973 Tax: $4,300 (2025)Community: Cadillac HomesSingle Family
Taxes:$4,300
Elementary School: Partin Settlement Elem
Remarks: Charming corner-lot single-family home for sale in the heart of Kissimmee! This spacious 3-bedroom, 2-bathroom home offers 1,745 square feet of living space on a generous 0.28-acre lot. The home has been well maintained and features a bright kitchen with stainless steel appliances, abundant storage, and natural light throughout. It also includes a two-car garage, central heating and air conditioning, and a cozy patio that opens to a huge backyard — perfect for outdoor gatherings or private relaxation. A new roof was installed in 2022, and the home is now vacant and move-in ready. Located on a quiet corner lot in the Cadillac Homes subdivision, this home offers solid construction, timeless charm, and a convenient location close to shopping, dining, and major roadways. Don't miss your chance to make this gem your own — schedule a showing today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Andres Ospina Rivera (321-821-8446)
2994 BIG SKY BLVD, KISSIMMEE, FL 34744
$450,0004 Days on yellowkey MLS ID: S5153486
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2700 Built: 1982 Tax: $4,341 (2025)Community: Acreage & UnrecSingle Family
Taxes:$4,341
Elementary School: East Lake Elem
Remarks: It's not every day you see something like this. This one is truly a Game Changer!! 2.6 ACRES of BEAUTIFUL property tucked in providing you the ultimate privacy yet minutes to EVERYTHING. This 3-bedroom 2 story home sits in the middle of the property with 2 large sheds in the far end of the property. Primary bedroom on the first floor with 2 additional bedrooms and a loft area on the second floor. Home is backed to a conservation area. Enjoy beautiful nature views with quiet breeze as you start your day and end your night in tranquility. Side of home has a pond view. The Best part about this property is there is NO HOA!! So, if you been looking for that something special to call Home this is it right HERE!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Mayra Cordero (407-242-7892)
988 PINEWOOD ST, KISSIMMEE, FL 34744
$343,9904 Days on yellowkey MLS ID: O6424143
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1489 Built: 2025Monthly Fee: $86 Tax: $2,304 (2025)Community: Fish Lake CoveSpa: NoTownhouse
Taxes:$2,304
Remarks: Fish Lake Cove presents the Sterling. This spacious all concrete block construction townhome optimizes living space with an elevated design featuring 3 bedrooms, 2.5 baths and a 2 Car Garage. As you enter the foyer, you’ll step into a home that reflects your style with an open concept dining area, living room and a spacious kitchen with bar seating. The kitchen is complete with a pantry, stainless steel appliances, and upgraded countertops making cooking and cleaning a breeze. Towards the back of the townhome you will find a half bathroom and private entry from the garage. As you head up to the second floor you are greeted with the 3 bedrooms and 2 bathrooms. The bedroom one-bathroom impresses with double bowl vanity, and modern shower/tub space as well as a spacious walk in closet. The second floor is complete with two guest bedrooms, an additional bathroom, and an enclosed laundry room space. This home features modern details that elevate your personal style. Like all homes in Fish Lake Cove, the Sterling includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
2275 SOUTHBURY DR, KISSIMMEE, FL 34744
$346,790134 Days on yellowkey MLS ID: O6386802
4 Days Off yellowkey (back on 6/24/2026)
REDUCED by $2,000 (0.6%) on 06/08/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1553 Built: 2026Monthly Fee: $130 Tax: $1,610 (2025)Community: TohoquaSpa: NoTownhouse
Taxes:$1,610
Remarks: Tohoqua is the kind of neighborhood you've been looking for, with a family-friendly amenity center and a location within proximity to major roadways, including US-192, the FL. Turnpike and within 30 minutes of Orlando International Airport, Orlando’s world class amusement parks, and Medical City. Enjoy the adjacent Twin Oaks Park Florida Trail, featuring trails along famous Lake Tohopekaliga and connectivity to regional trail networks. A planned Village Center at the entrance to Tohoqua will offer shops, restaurants, healthcare and medical offices, a farmers' market and much more. Community amenities include a clubhouse, resort-style pool, community parks, a dog park, fitness center, sports courts, a playground and more! State-of-the-art technology will ensure that your family and business are connected to the latest and best tech options. Introducing the Orchid townhome, a new construction home that seamlessly combines luxury and convenience. This modern townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage, all complemented by our Move-In Ready appliance and window blinds package. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Elkins White cabinetry, a decorative tile backsplash, Blanco Maple quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The main living areas include our Luxury Vinyl Plank flooring, with tile in the bathrooms and laundry room. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. With thoughtful design, high-end finishes, and a focus on everyday convenience, the Orchid townhome is a perfect blend of style and practicality, offering a truly elevated living experience.
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
1895 HICKORY BLUFF RD, KISSIMMEE, FL 34744
$349,900175 Days on yellowkey MLS ID: S5142089
3 Days Off yellowkey (back on 6/16/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 2017Monthly Fee: $11 Tax: $6,019 (2025)Community: Kindred Ph 1C Pb 25 Pgs 127-134 Lot 373Spa: NoSingle Family
Taxes:$6,019
Remarks: Brand-New Roof to Be Installed Before Closing! This charming 3-bedroom, 2-bath home offers the perfect combination of comfort, convenience, and value. Featuring a spacious backyard ideal for entertaining and family gatherings, this move-in ready property is located in a highly desirable central area just minutes from major avenues, shopping centers, restaurants, gas stations, and only 1 mile from Florida Turnpike and US-192. Residents enjoy access to resort-style community amenities including swimming pools, fitness centers, walking trails, tennis courts, and social spaces—perfect for enjoying the Florida lifestyle. With stylish living spaces, an unbeatable location, and the added benefit of a brand-new roof prior to closing, this home is an incredible opportunity for buyers seeking peace of mind and long-term value. Motivated sellers—schedule your showing today!
Listing is courtesy of: REALTY ONE GROUP MAGIC CITY (407-589-9080)
Listing Agent: Elsie Cruz (407-561-4957)
1959 SUMMER SERENITY DR, KISSIMMEE, FL 34744
$390,00025 Days on yellowkey MLS ID: S5151902
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2072 Built: 2023Monthly Fee: $7 Tax: $6,594 (2025)Community: Tohoqua Ph 4BSpa: NoSingle Family
Taxes:$6,594
Remarks: Welcome to this beautifully maintained Pulte-built bungalow in the highly desirable Tohoqua community. Built in 2023, this move-in ready home offers 2,072 square feet of thoughtfully designed living space featuring 3 bedrooms, 2.5 bathrooms, a spacious loft, and a rear-entry 2-car garage. A charming covered front porch welcomes you into a bright and inviting open-concept floor plan designed for both comfortable everyday living and effortless entertaining. The main level features tile flooring throughout the living areas, abundant natural light, and seamless flow between the living room, dining area, and kitchen. The kitchen serves as the heart of the home, showcasing white shaker cabinetry, quartz countertops, stainless steel appliances, a large center island with seating, stylish pendant lighting, and ample storage space. All kitchen appliances, along with the washer and dryer, are included for the new owner. Upstairs, an oversized loft provides flexible space ideal for a second living area, media room, home office, fitness area, or playroom. The spacious primary suite features a large walk-in closet and a private ensuite bathroom with dual vanities and quartz countertops. Two additional bedrooms share a full bathroom, while a convenient half bath is located on the first floor for guests. Additional highlights include ceiling fans, window blinds throughout, Ring doorbell, tile flooring throughout the main living areas, well-maintained carpeting upstairs and on the staircase, and a rear-entry 2-car garage with additional driveway parking for two more vehicles. Perfectly positioned facing a beautifully landscaped green space with sidewalks and pedestrian-friendly walkways, this home offers a peaceful setting without direct traffic immediately in front of the property, creating a more private and welcoming environment. Residents of Tohoqua enjoy outstanding community amenities, including multiple resort-style swimming pools, cabanas, a recently opened clubhouse and pool area, tennis courts, passive parks, playgrounds, walking trails, and beautifully maintained common areas designed to promote an active and connected lifestyle. Conveniently located near schools, shopping, dining, and everyday conveniences, this exceptional home combines modern construction, functional living spaces, and outstanding value in one of Osceola County’s most sought-after newer communities.
Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)
Listing Agent: Lymaris Perez (407-676-3708)
1610 MOHEGAN BLVD, KISSIMMEE, FL 34744
$339,90061 Days on yellowkey MLS ID: O6408062
REDUCED by $16,000 (4.5%) on 07/10/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2167 Built: 2014Monthly Fee: $164 Tax: $4,753 (2025)Community: Heritage RunTownhouse
Taxes:$4,753
Remarks: MOTIVATED SELLER!!! Discover this stunning 3-bedroom + loft corner unit townhome in the highly desirable gated community of Heritage Run! The moment you step inside, you'll be captivated by the elegant tile flooring that stretches across the entire first floor, effortlessly combining contemporary style with everyday livability. At the center of it all is a gourmet kitchen designed for entertaining — featuring 42-inch solid wood cabinetry, gleaming granite countertops, stainless steel appliances, and a generous breakfast bar that's perfect for hosting friends and family. Head upstairs to find a sprawling primary suite complete with a luxurious en suite bath boasting dual vanities, a walk-in shower, and an oversized walk-in closet. The open loft area provides flexible space ideal for a home office, personal gym, or media room. Both secondary bedrooms are generously sized and thoughtfully appointed with private vanities and access to a shared guest bath perfect for family members or visiting guests. Out back, a screened-in porch overlooks a tranquil greenspace, offering a peaceful retreat for your morning coffee, evening wind-down, or lazy weekend mornings. A washer and dryer are also included for added convenience. Situated just off Highway 192 and the Turnpike, you're only minutes away from premier shopping, top-rated dining, Walt Disney World, and Orlando International Airport. Homes like this move fast, book your private showing, TODAY!
Listing is courtesy of: THE SHUGAN GROUP INC (407-755-7588)
Listing Agent: Trevor Hall (646-872-3261)
2540 WINNERS CIR, KISSIMMEE, FL 34744
$650,000145 Days on yellowkey MLS ID: O6382446
0 Days Off yellowkey (back on 7/6/2026)
REDUCED by $39,000 (5.7%) on 07/03/2026
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 3246 Built: 2000 Tax: $3,688 (2025)Community: Winners ParkSpa: NoSingle Family
Taxes:$3,688
High School: Tohopekaliga High School
Remarks: Under contract-accepting backup offers. Virtually Staged. **WELCOME HOME** NO HOA, HALF AN ACRE of land, a PRIVATE POOL, and a full SEPARATE APARTMENT on the main floor – welcome to your next chapter on Winners Circle in the Winners Park community of Kissimmee! EXTERIOR PAINT (2023), NEW WINDOWS (2022), DETACHED AIR CONDITIONED GARAGE (2022), septic tank serviced (2022) – big-ticket items are already started, giving you confidence and flexibility from day one. Situated on an expansive .50 ACRE LOT, this spacious two-story POOL HOME delivers over 3,000 square feet of living space, mature landscaping, a TILE ROOF, long paver driveway, and standout curb appeal. The SCREENED POOL with PAVER DECK creates a private backyard retreat with room to entertain, garden, or just spread out. Inside, the flexible layout is ideal for large households, multi-generational living, or anyone needing versatile space. The full first-floor apartment includes its own kitchen open to a living area, bedroom, and full bath – perfect for in-laws, guests, extended stays, or even creative work from home options! The main home features comfortable formal and family spaces, a well-equipped kitchen with casual dining, and an expansive FLORIDA ROOM complete with a full bath and cozy office space – offering endless possibilities for hobbies, remote work, or additional entertaining. Upstairs, a BONUS/LOFT anchors the remaining bedrooms, while the generous PRIMARY SUITE provides a peaceful escape with an updated private en-suite bath. Car enthusiasts, hobbyists, or entrepreneurs will appreciate the two-car attached garage plus the like-new detached, air-conditioned garage – currently used as a dojo, but easily transformed into a workshop, craft studio, gym, or business space. Updated yet still offering room to personalize, this home offers the rare combination of space, privacy, flexibility, and location. Perfectly situated just off Simpson Road, you will enjoy easy access to the Florida Turnpike, shopping, dining, area lakes, attractions, and world-famous theme parks – all while coming home to a quiet, established neighborhood with no HOA restrictions. Room to grow inside and out. Versatility for today and tomorrow. Schedule your tour today and be the winner on Winners Circle! **Seller may consider buyer concessions if made in an offer**
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
1757 QUAIL RIDGE LOOP, KISSIMMEE, FL 34744
$344,999106 Days on yellowkey MLS ID: O6391222
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1109 Built: 1992 Tax: $4,829 (2025)Community: Quail Hollow Ph 1Single Family
Taxes:$4,829
Remarks: Back on the market!! Nestled on a premier waterfront conservation lot in one of the most desirable sections of Mill Run, this beautiful 3-bedroom, 2-bathroom home offers the ultimate retreat with unparalleled privacy. New Roof 2023, New Electrical Panel 2023. Surrounded by mature trees and lush landscaping, and a private pond next door. The outdoor oasis features a screen-enclosed pool. The interior is move-in ready, with porcelain tile throughout, an L-shaped living/dining area that overlooks the pool, and a kitchen with stainless steel appliances, plus a two-car garage for convenience. Combining a serene, private setting with the convenience of being just minutes from top-rated schools and shopping, this home truly offers the best of both worlds.
Listing is courtesy of: 407 PROPERTIES (407-545-2594)
Listing Agent: Peggy Moore (407-697-1119)
930 SHORE DR, KISSIMMEE, FL 34744
$598,50056 Days on yellowkey MLS ID: TB8510529
REDUCED by $16,500 (2.7%) on 07/10/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3269 Built: 1958 Tax: $3,326 (2025)Community: Cypress Shores RepSingle Family
Taxes:$3,326
Remarks: ** Motivated Seller** Whether enjoying a morning cup of coffee or an evening glass of wine the views from this beautiful ranch home and this one of kind lake home are spectacular! The 22,700 acre lake has been deemed, by Bassmaster magazine in their issue of top 100 lakes calling Toho, “the most consistent lake in the country for producing both numbers and Trophy sized bass”. Leave as is or create your own special lake place. This home is situated on almost an acre with enough room to put an enclosed pool and your dream of out door kitchen. Many new upgrades including; New Roof (2026), New Paint (Interior/Exterior 2026), New Carpet (2026), New Hot Water Heater (2026), New Air Conditioner (2025) and so much more to offer. This home is conveniently located only 30 minutes to Disney World, Magic Kingdom, and Universal Studios. This is a must see and must purchase home to enjoy the perfect Florida lake life. **Appraised 2026 (Substantially Higher than asking) Available upon request to qualified buyer.
Listing is courtesy of: WWW.HOMEZU.COM (877-249-5478)
Listing Agent: Jason Saphire (877-249-5478)
2780 VICKIE CT, KISSIMMEE, FL 34744
$3,499,000171 Days on yellowkey MLS ID: O6376322
Bed: 10 Bath: 7.5 Gar: 4 Liv Area Sq Ft: 9881 Built: 2008 Tax: $15,347 (2025)Community: Florida Fruit Belt Sales Co 1Spa: YesSingle Family
Taxes:$15,347
Remarks: Discover the epitome of equestrian luxury with this pristine 5.85-acre estate, featuring a state-of-the-art four-stall barn, premier riding ring, and a meticulously designed custom home and guest house. Strategically in Central Florida, just minutes from major roadways and an easy location to all the major horse shows and events Florida offers. Property also backs up to an 18-hole beautiful golf course, adding to the privacy of this property. This exceptional estate’s main residence boasts 8,261 sf of luxury living with seven bedrooms, five baths, all carefully renovated with designer selections. Gorgeous formal dining room can seat 12, ideal for those special holidays. An incredible chef’s kitchen features a bar-style center island, all opening to large gathering space, which features a gorgeous fireplace with custom-built mantle. The chef’s kitchen is home to updated stainless appliances, custom wood cabinetry, center island with sink and bar seating, granite counters, hidden pantry, double refrigerator and freezer, and generous counter space to spread out. The back of house has views from an incredible window and door bank, which allows beautiful ambient light through the house and overlooks the outdoor resort-style pool and entertaining area. This is the home your friends and family will gather in and want to stay! The home office or flex room is designed for a golf simulator, so practice your game while taking those work calls. As you go outside, an outdoor paradise awaits, where the pool takes center stage for a staycation at home with a lazy river, spa, pool cabana and firepit, and deck that wraps the pool, providing plenty of space for a large crowd. The covered lanai extends across the back and includes a fully appointed summer kitchen with room for alfresco dining space to soak in the Florida weather. Primary suite with spa-like bath, which includes dual vanities, steam station of clothing, makeup vanity, double head shower, jetted tub and built-in jewelry cabinet. Two of the seven bedrooms are upstairs with great landing area. Home has terrific storage and every detail accounted for. The equestrian amenities are designed for horse lovers and include four stables, a tack room, sliding doors on three sides, an incredible 1,800-square-foot garage with roll-up doors for ease of parking your vehicles and toys, as well as a Tesla charger. A 1,324-square-foot porte-cochere connects the main house to guest house. Guest house or in-law suite is 1,620 square feet, three bedrooms and two baths, providing privacy for all. The function of this property is designed for the serious equestrian in a serene location while being close to a city lifestyle. Other features of the unique property include whole-house generator (Generac), inside laundry organization center with pet washing area, plantation shutters, Icynene insulation, irrigation (not in pastures), crown molding and chair rail, central vacuum system, in-floor outlets, tankless water heater, garage roof 2022, upstairs air conditioner 2023, and more. This property was carefully designed with the highest quality architectural details and craftsmanship, so expect to be impressed. If the equestrian lifestyle is what you are looking for, this location and property cannot be matched. In the heart of Central Florida, it is close to attractions, airports, downtown Orlando and more. Only five minutes by golf cart to Kissimmee Bay Country Club and golf course. Inquire about a private tour.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
4405 BISCAYNE BREEZE WAY, KISSIMMEE, FL 34744
$460,00094 Days on yellowkey MLS ID: O6398072
4 Days Off yellowkey (back on 7/10/2026)
REDUCED by $15,000 (3.2%) on 06/04/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2601 Built: 2011Monthly Fee: $111 Tax: $4,260 (2025)Community: North Point Ph 1ASingle Family
Taxes:$4,260
Middle School: Narcoossee Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to 4405 Biscayne Breeze Way, located in the highly desirable gated community of North Pointe in Kissimmee. This beautifully maintained two-story residence offers the perfect combination of comfort, space, and scenic waterfront living. Featuring 4 bedrooms, 2.5 bathrooms, and a 2-car garage, this home sits on an oversized homesite with peaceful water views and a spacious backyard designed for enjoying the Florida lifestyle. Offering over 2,600 square feet of living space, the thoughtfully designed floor plan provides both functionality and flexibility for everyday living and entertaining. Recent major updates include a new roof (2023), AC system (2023), water heater (2022), and upgraded flooring throughout, giving buyers added peace of mind and modern appeal. Inside, you’ll find bright and spacious living and dining areas filled with natural light, along with a well-appointed kitchen that opens seamlessly to the main living space, creating the ideal setting for gatherings and daily living. Upstairs features generously sized secondary bedrooms and a comfortable primary suite complete with ample closet space and a private en-suite bathroom. Step outside to your own private retreat where tranquil water views, mature fruit trees, and an oversized backyard create the perfect atmosphere for relaxing evenings, entertaining guests, or enjoying outdoor living year-round. Residents of North Pointe enjoy a gated entrance, community pool, playground, nearby parks, and low HOA fees. Ideally situated along East Lake Tohopekaliga and adjacent to Austin Tindall Sports Complex, the community offers easy access to recreation and outdoor activities. Conveniently located near SR-417 and Boggy Creek Road, this home provides quick access to Lake Nona, Medical City, Orlando International Airport, and Downtown Orlando, with shopping, dining, and everyday conveniences just minutes away. This is an exceptional opportunity to own a spacious water-view home in one of Kissimmee’s most sought-after gated communities. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Yosseff Roman (407-394-5843)
700 ADRIANE PARK CIR, KISSIMMEE, FL 34744
$589,90027 Days on yellowkey MLS ID: S5152087
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2948 Built: 1992Monthly Fee: $37 Tax: $6,962 (2025)Community: Adriane ParkSpa: YesSingle Family
Taxes:$6,962
Remarks: Welcome to the beautiful community of Adriane Park. With large lots and only 54 homes, they just don't make neighborhoods like this one any more. This home sits on over 1/3 of an acre and overlooks the beautiful pond with a fountain. The home itself is absolutely gorgeous, with exquisite curb appeal with brick overlays and hardy board siding. The roof was replaced in December of 2024. The main living and dining area have hardwood floors and there is crown moulding throughout the downstairs. The living room has a wood burning fireplace. The kitchen has ceramic tile, stainless steel appliances and Schrock handcrafted pecan wood cabinetry. The primary bedroom is downstairs with it's own private bathroom, as well as another half bathroom downstairs. Indoor laundry is located downstairs next to the half bath. Upstairs there are 4 more spacious bedrooms, all with walk-in closets! The fifth bedroom has double doors and dual walk-in closets and can be used as a flex space, or upstairs living area. The Florida Room is huge with ceramic tile and is air conditioned through the main unit and also offers a mini split HVAC unit. It leads out to the beautiful screened in pool area that is perfect for entertaining, with landscaping and an electric above ground hot tub. The pool overlooks the neighborhood pond, which also means no rear neighbors. This home is ready to be the focal point of all of your family gatherings!
Listing is courtesy of: ALL STAR PROPERTIES OF CENTRAL (407-846-9100)
Listing Agent: Kevin Waldbieser (407-460-7993)
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