Location: Kissimmee
Keyword(s): Osceola High School
Keyword(s) High School: Osceola High School
Do Not Show Listings
609 CORNERSTONE DR, KISSIMMEE, FL 34744
$269,9009 Days on yellowkey MLS ID: O6398322
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1512 Built: 2007Monthly Fee: $284 Tax: $3,237 (2025)Community: Heritage Key VillasTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,237
Elementary School: Mill Creek Elem (K 5)
High School: Osceola High School
Tax Year: 2025
Middle School: Denn John Middle
Remarks: This beautiful townhouse is perfectly situated a short walk from the community heated swimming pool, spa, 24-hour fitness, clubhouse, and business center—everything you need right at your doorstep for resort style living! Located in a secure, gated community and move-in ready, this spacious 3-bedroom, 2.5-bath home offers both comfort and convenience in every detail. The large, bright kitchen features ample cabinetry, a newer granite island, and a double oven—ideal for everyday meals and effortless entertaining. Adjacent to the kitchen, the expansive dining room boasts an elegant tray ceiling and recessed lighting, creating a modern, upscale ambiance. The generously sized living room offers plenty of space for relaxing or hosting guests. Sliding glass doors lead to a screened-in patio—perfect for enjoying beautiful Florida days in comfort and style. Upstairs, the desirable split floor plan places the primary bedroom on one end for added privacy, with the second and third bedrooms located on the opposite side. One of the secondary bedrooms can easily be converted into a home office, making it perfect for today’s work-from-home lifestyle. The spacious primary suite includes a walk-in closet and a private ensuite with a tub/shower combination, granite countertop, and ample storage. The guest bathroom features a walk-in shower, granite countertops, and generous storage as well. All bathrooms are finished with granite countertops, adding a sleek, modern touch throughout. The first floor is finished with tile for easy maintenance, while the upstairs bathrooms also feature tile flooring, and the bedrooms are carpeted for added comfort. The home has a new AC unit (2024). Entire house painted (2024). A prime location just moments from Disney World, Silver Spur Arena and other major attractions, shopping and entertainment.
Listing is courtesy of: RANDOLPH & CO. (407-454-0214)
Listing Agent: Ron Randolph (407-454-0214)
2477 TOSCOLONA DR, KISSIMMEE, FL 34741
$294,000130 Days on yellowkey MLS ID: O6367342
REDUCED by $5,000 (1.7%) on 04/15/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1528 Built: 2019Monthly Fee: $304 Tax: $5,407 (2024)Community: Tapestry Ph 4Townhouse
Taxes:$5,407
Elementary School: Floral Ridge Elementary
Tax Year: 2024
Middle School: Kissimmee Middle
Remarks: Take a look this furnished townhome in a gated community. The layout includes a 3 bed, 2 and 1/2 bath, a front portico, 1 rear balcony, and a rear entry 2 car garage. Downstairs you'll find the kitchen with granite countertops is also fully tiled and contains a large living space and convenient half bathroom. All of your bedrooms are located upstairs for your privacy and convenience.The master bedroom features walking closet and a large balcony perfect for your morning coffee.Tapestry offers 24 hours private security, a Resort style Club House like no other in the area, beach entry pool with slide and splash pad, grill area , fitness center, walking trails and more! Enjoy this beautiful property located just minutes from Orlando International Airport and the world-famous Disney and Universal theme parks. Schedule your appointment today!
Listing is courtesy of: YORK MILLS REALTY LLC (407-620-8528)
Listing Agent: Leo Shao (407-569-6769)
2300 PAINTER LN, KISSIMMEE, FL 34741
$395,00070 Days on yellowkey MLS ID: O6382119
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1820 Built: 2016Monthly Fee: $304 Tax: $5,420 (2025)Community: Cypress Reserve VillasTownhouse
Taxes:$5,420
Remarks: COMPLETELY REMODELED WITH OVER $50,000 IN UPGRADES. HOME HAS BEEN LEASED
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Lorinda Orozco, Pa (407-562-8757)
1495 SKYLINE DR, KISSIMMEE, FL 34744
$499,90049 Days on yellowkey MLS ID: S5145209
REDUCED by $25,000 (4.8%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2094 Built: 1973Monthly Fee: $16 Tax: $5,404 (2025)Community: Harbour Oaks Unit 1Spa: NoSingle Family
Taxes:$5,404
Elementary School: Partin Settlement Elem
Middle School: Neptune Middle (6-8)
Remarks: One or more photo(s) has been virtually staged. SELLER ASSISTING WITH BUYER FINANCING, 2/1 BUYDOWN ON THE INTEREST RATE! Welcome to this wonderful 3-bedroom, 2-bathroom completely renovated home offering nearly 2100 sq. ft. of living space in the highly desirable Harbour Oaks community in Kissimmee, Florida. This spacious residence is designed for both comfort and style, featuring an open-concept layout, modern finishes, and thoughtful upgrades throughout. This renovation includes NEW Roof-Soffits-Gutters, Interior and Exterior Paint, both Bathrooms and Kitchen rehabs with Quartz Stone counters, SS Appliances, Breakfast Bar, Wet Bar, Luxury Vinyl Flooring, Blinds and Ceiling Fans throughout, Pool Refinished, Painted Decks front and back, Wood Burning Fireplace, Oversized 2-Car Garage, Pool Gazebo and Vinyl Fenced backyard. Enjoy your own private outdoor oasis with a sparkling pool and huge back yard—perfect for year-round Florida living and entertaining. Located just minutes from Historic Downtown Kissimmee, you'll have convenient access to shopping, dining, and entertainment. You're also perfectly positioned with a quick commute the Florida Turnpike, Lake Nona Medical City, major theme parks, schools, shopping and dining and the stunning Space Coast beaches. With its generous floor plan, multiple living areas, and every exceptional upgrade, this remarkable home has it all. Don’t miss your chance—schedule your showing today!
Listing is courtesy of: MACERA REALTY GROUP INC (407-246-1677)
Listing Agent: Peter Macera (407-970-2104)
1714 CHERYL LN, KISSIMMEE, FL 34744
$749,00021 Days on yellowkey MLS ID: O6395426
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3609 Built: 1989 Tax: $3,559 (2025)Community: Regal Oak Shores Unit 8Single Family
Taxes:$3,559
Remarks: One or more photo(s) has been virtually staged. Positioned on an expansive 0.45-acre lot with no HOA in Kissimmee, this custom-built residence delivers space, privacy, and elevated finishes rarely found at this price point. Inside, the architecture is clean and intentional, highlighted by soaring ceilings, crown molding, and a seamless open layout designed for both everyday living and entertaining. At the center of the home is a fully upgraded chef’s kitchen, featuring premium granite countertops, custom cabinetry, and high-end built-in appliances including a double oven and integrated refrigerator, complemented by a functional butler’s pantry for added storage and prep space. The main living areas flow effortlessly, creating a bright and inviting environment with strong indoor-outdoor connectivity. The first-floor primary suite is designed for privacy and scale, offering a spacious layout, large walk-in closet, and a well-appointed bath with a soaking tub, oversized shower, and dual vanities. A dedicated front flex space provides versatility as a home office, study, or additional living area. Upstairs, three additional bedrooms are thoughtfully positioned along with two full bathrooms, including an en-suite located on the second floor, offering flexibility for multi-generational living or guest accommodations. The outdoor space is equally impressive, anchored by a large screened-in patio with elevated ceilings, ideal for year-round use. Beyond, the oversized backyard offers ample room to design a custom pool or outdoor retreat, all without the restrictions of an HOA. Located in a highly accessible area of Kissimmee, this home is just minutes from major roadways including the Florida Turnpike and 417, providing easy access to Lake Nona’s Medical City and NeoCity, a growing hub for technology and innovation. You’re approximately 25 minutes to Orlando International Airport, 30–35 minutes to Walt Disney World and major attractions, and about 20–25 minutes to Downtown Orlando. Everyday conveniences are close by with Publix, Walmart, The Loop shopping center, restaurants, and schools all within a short drive. For weekend getaways, Florida’s east coast beaches are roughly 60–75 minutes away. **UPGRADES LIST AVAILABLE UPON REQUEST**
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Veronica Figueroa (407-519-3980)
2827 NEWCOMBE LN, KISSIMMEE, FL 34741
$279,900199 Days on yellowkey MLS ID: O6350162
3 Days Off yellowkey (back on 3/23/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1475 Built: 2025 Tax: $1,871 (2024)Community: Tropical Park Unit 4Manufactured Home
Taxes:$1,871
Elementary School: Highlands Elem
Remarks: LOCATION, LOCATION, LOCATION! This fantastic property features a 2025 NEW manufactured home and is truly ready for move-in! ?It boasts three spacious bedrooms and two comfortable full bathrooms. Enjoy the sleek look and easy maintenance vinyl flooring throughout the entire home. ?A sliding door from the living area leads out to a relaxing patio—perfect for hosting barbecues and spending quality time with family and friends. The home also includes a spacious living and dining area, an eating space in the kitchen, and all appliances are included. ?Recent updates include a new drain field. The home is centrally located with incredibly easy access to shopping, restaurants, and the Orlando International Airport. ?Schedule your showing today and make this beautiful home yours! The seller is highly motivated.
Listing is courtesy of: CENTRAL REALTY GROUP AND PROPERTIES (407-582-9011)
Listing Agent: Bernardino Castorani (407-582-9011)
2805 CARTER GROVE LN, KISSIMMEE, FL 34741
$670,000198 Days on yellowkey MLS ID: O6350502
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3233 Built: 2014Monthly Fee: $97 Tax: $7,985 (2024)Community: Preserve At Tapestry Ph 1Single Family
Taxes:$7,985
Remarks: Welcome to this stunning move-in-ready home where thoughtful design, premium upgrades, and energy efficiency come together in perfect harmony. This beautifully maintained home offers the perfect balance of luxury, comfort, and convenience. From first glance, curb appeal impresses with a stone-accented front elevation, well-maintained landscaping, and a striking red brick walkway leading to a covered front porch. Step inside to a bright, airy foyer featuring polished porcelain tile, clean architectural lines, and a sleek glass-panel staircase setting the stage for the refined interior that follows. The open-concept main level is both stylish and highly functional. The family room is anchored by a custom entertainment wall with textured paneling, LED accent lighting, and a floating media console, an ideal setting for relaxed nights or elegant entertaining. Crown molding, recessed lighting, and a soft neutral palette enhance the elegant atmosphere, while wide visibility flow effortlessly into the dining area and kitchen. The kitchen is a true showpiece; a modern, sleek, and designed for both culinary performance and visual impact. High-gloss white cabinetry offers ample storage, white stunning quartz countertops with bold veining wrap around a dramatic waterfall island that doubles as a prep space and social hub. The waterfall island is anchored by a distinctive tile inlay, elevating the kitchen’s designer aesthetic., complemented by a sculptural LED pendant light overhead and ambient LED ceiling lighting throughout. Outfitted with premium stainless-steel appliances, the kitchen includes a Samsung French door smart refrigerator with digital display, double wall ovens, a smooth cooktop with a stylish range hood, and an integrated dishwasher. A continuous marble-look quartz backsplash ties the space together. Adjacent to the kitchen, the dining area is bathed in sunlight from sliding glass doors that lead directly to the backyard. Tucked beneath the staircase is a custom-designed bar nook complete with a stacked stone backsplash, glass shelving, recessed lighting, and a built-in beverage cooler, ideal for relaxing evenings or hosting guests. Nearby, a built-in display wall with individually lit niches offers a refined way to showcase art, collectibles, or personal décor. Upstairs, a spacious loft serves as a second living room or media lounge, featuring a textured accent wall, floating console, and contemporary lighting. Glass-panel railings maintain the home’s open feel while adding a modern edge. The primary suite is located on the first floor, offering privacy and comfort. The ensuite bathroom includes a built-in closet system for efficient storage, along with updated fixtures and finishes for a clean, spa-like feel. Each bedroom features porcelain tile flooring, modern ceiling fans, and ample natural light. Bathrooms are tastefully updated, with three full baths and a convenient half-bath. Step outside to your private backyard retreat. A large, covered patio with wood-beam construction offers shaded comfort, while an expansive paver patio provides plenty of space for outdoor dining, lounging, or entertaining. A curved paver walkway leads past dual HVAC units and the solar energy system. Nestled just minutes from The Loop—a vibrant open-air shopping and entertainment destination, movie theaters, 20 minutes from Orlando’s world-famous theme parks and the Orlando International Airport. Schedule your private showing today!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Carmen Estrella (407-960-0914)
4177 FLYING FORTRESS AVE, KISSIMMEE, FL 34741
$190,000125 Days on yellowkey MLS ID: S5140466
4 Days Off yellowkey (back on 4/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 930 Built: 1984Monthly Fee: $50 Tax: $149 (2024)Community: Waterway VillageTownhouse
Taxes:$149
Elementary School: Kissimmee Elem
Remarks: This cozy Villa/Townhome offers 2 bedrooms and 2 full bathrooms, with 930 square feet of living area in the hearts of Kissimmee. This home features open floor plan, ceramic tiles flooring throughout, screened & covered front entry, living/dining combo, skylights in kitchen, inside separate laundry, nice outside sitting area, large vinyl fenced yard, low HOA, and Taxes. Enjoy the fresh air or cool off in the fenced in backyard. Property located very close proximity to Schools, Public Transportation (junction of public bus), Dining, Shopping, Banking, Loop Mall, Wal-Mart, Hospitals, Doctors Office, Major Roads (US 192, Osceola Parkway, John Young Parkway) and Major Attractions. This Townhouse is in great shape and recently updated plumbing system. An excellent opportunity for the first time homebuyer or investor. *All the information relating to this MLS Listing is intended to be accurate but cannot be guaranteed and must be verified by the buyer and buyer's agent. Opportunity knocks - ACT FAST!
Listing is courtesy of: PROFILES INTERNATIONAL REALTY (321-297-8161)
Listing Agent: Mohammed Hossain (407-925-3442)
3331 WHITESTONE CIR #201, KISSIMMEE, FL 34741
$240,000189 Days on yellowkey MLS ID: O6353322
0 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1495 Built: 2006Monthly Fee: $389 Tax: $3,843 (2024)Community: Flora Ridge Condo Ph 7 Bldg 12Condo
Taxes:$3,843
Remarks: One or more photo(s) has been virtually staged. BACK ON THE MARKET! Spacious and VERY WELL-MAINTAINED 3-bedroom, 2-bath condo located on the 2nd floor in the desirable gated community of Flora Ridge in Kissimmee. This inviting condominium features wood-style flooring in the open great room, tile in the wet areas, and cozy carpet in the bedrooms. The split floor plan offers added privacy, with the primary suite separated from the other two bedrooms. The primary ensuite includes dual sinks, a private water closet, and a sleek walk-in shower—perfect for those who prefer ease of access and modern comfort over a traditional bathtub. The bright kitchen is equipped with all stainless steel appliances, lots of cabinets and counter space, a pantry closet, and a convenient washer and dryer area discreetly enclosed by a pocket door. Open both French doors to enjoy the outdoors from your screened-in balcony, perfect for relaxing or entertaining. Flora Ridge has fantastic amenities including a community pool, a gazebo, and serene waterfront walking path ideal for peaceful strolls and sunset views. Conveniently located within 3 minutes of Osceola Parkway, 7 minutes from The Loop shopping centers, and about 2 miles from the 417 Toll; this home provides easy access to major roads, schools, restaurants, and shopping areas. Majestically set away from the hustle and bustle, yet close enough to everything you need!
Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)
Listing Agent: Luz Lovera (407-325-5027)
2879 OCONNELL DR, KISSIMMEE, FL 34741
$435,00042 Days on yellowkey MLS ID: O6390445
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2245 Built: 2005Monthly Fee: $100 Tax: $2,760 (2025)Community: Cypress ReserveSingle Family
Taxes:$2,760
Remarks: Brand New Interior Paint--Move in Ready! Welcome to the beautifully maintained 3 Bedroom 2-Bathroom home located in the desirable gated community of Cypress Reserve! Featuring an open concept layout with wood flooring throughout, crown molding and window treatments! This home offers both style and comfort on a gorgeous, oversized lot! The kitchen is fully equipped with a refrigerator, dishwasher, oven and microwave and showcases Corian countertops, tiled backsplash, maple cabinetry, and a closet pantry. An eat-in area just off of the family room creates the perfect space for casual dining and everyday living. The spacious primary suite and secondary bedrooms offer a functional split floor plan. A 2023 AC and 2018 ROOF provides a peace of mind. Washer and dryer convey with the sale. Step outside and enjoy a large, enclosed lanai overlooking an expansive backyard--ideal for entertaining or relaxing year-round. Move in ready and conveniently located near shopping (The Loop), dining, and major roadways. Come and see this home today!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Catherine Lambert Pa (407-908-2525)
2513 HIGHLAND AVE, KISSIMMEE, FL 34741
$300,00014 Days on yellowkey MLS ID: O6397907
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1450 Built: 1959 Tax: $3,615 (2025)Community: Kissimmee Highlands 1St AddSingle Family
Taxes:$3,615
Remarks: Full of old-school charm and lovingly maintained by the same family since new, this inviting 3-bedroom, 2-bath home offers comfort, character, and an unbeatable central location. From the moment you arrive, you’ll appreciate the pride of ownership and timeless appeal throughout. Inside, the home features a warm and welcoming layout highlighted by a cozy wood-burning fireplace—perfect for relaxing evenings. The functional floorplan includes an inside utility area for added convenience, while thoughtful updates such as a tankless water heater and an updated electrical breaker box provide peace of mind. Step outside to enjoy a fully fenced backyard, ideal for pets, play, or entertaining. The covered and screened back porch creates the perfect space to unwind year-round while enjoying the outdoors in comfort. A carport with additional storage above offers practical space for vehicles and extra belongings. Located just minutes from the hospital, downtown, Amtrak, the bus station, and SunRail, this home offers easy access to everything you need while maintaining a quiet, established neighborhood feel. A rare opportunity to own a well-cared-for home with character, updates, and a prime location—schedule your showing today!
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
3051 GREYSTONE LOOP #106, KISSIMMEE, FL 34741
$255,900101 Days on yellowkey MLS ID: O6372010
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1433 Built: 2006 Tax: $4,222 (2025)Community: Flora Ridge Condo Ph 2 Bldg 5Condo
Taxes:$4,222
Remarks: WOW! Highly Convenient First-Floor Condo in Prime Kissimmee Location! This exclusive first-floor condominium offers a functional and well-designed layout, perfect for comfortable living or investment. Upon entry, you are welcomed by a bright and inviting living area featuring large windows that fill the space with natural light and open to a private balcony with peaceful green views, ideal for relaxing or enjoying outdoor dining. The fully equipped kitchen boasts stainless steal appliances, spacious cabinetry, Tile in the kitchen, Livingroom, and hardwood style tile flooring in the bedrooms, seamlessly blending style, and functionality “NO CARPET”. Every detail of this home has been thoughtfully designed to support a relaxed and comfortable lifestyle. Community amenities include private parking, 24-hour security, a clubhouse, and a resort-style swimming pool. Enjoy the convenience of an urban lifestyle while maintaining the tranquility of open views and well-maintained surroundings. Strategically located in the heart of Kissimmee, just minutes from US-192, with easy access to shopping, dining, entertainment, and transportation. A short drive to The Loop Mall and close to Central Florida’s best restaurants and attractions. This versatile property is ideal as a primary residence, second home, or investment opportunity. A must-see first-floor unit—schedule your private tour today!
Listing is courtesy of: ATRIUM REALTY, LLC (833-919-1190)
Listing Agent: Ernani Sena (774-258-0635)
1030 VAQUERO LN, KISSIMMEE, FL 34741
$365,00069 Days on yellowkey MLS ID: S5143900
0 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1720 Built: 2004Monthly Fee: $83 Tax: $1,672 (2025)Community: EstanciaSpa: NoSingle Family
Taxes:$1,672
Elementary School: Thacker Avenue Elem (K 5)
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This 4 bedroom, 2 bathroom home with 1,720 sq ft checks the boxes buyers are asking for, space, layout, location, and the ability to move in without the wait. Located in a small gated community, you will enjoy a peaceful water view and a layout that actually makes sense. The oversized living and dining area gives you flexibility for everyday living or hosting, with crown moulding and tile flooring throughout the main spaces. The bedrooms feature wood floors, and the home is clean, well-maintained, and ready for its next owner. That is where the value is. Additional features buyers love: • 2 car garage with epoxy floors • In-home washer and dryer included • Open, functional floor plan • Natural light throughout • Vacant for easy showings and quick closing Whether you want a primary residence you can personalize over time or a solid investment, this property offers a great combination of condition, location, and opportunity. Seller is motivated and ready to make a deal. Homes with this much space, in a gated community, with a water view, at this price point, do not last. Schedule your showing and see the potential for yourself.
Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Naomi Embleton (407-709-6020)
877 HACIENDA CIR, KISSIMMEE, FL 34741
$365,00012 Days on yellowkey MLS ID: S5147690
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1955 Built: 2005Monthly Fee: $76 Tax: $5,410 (2025)Community: EstanciaSingle Family
Taxes:$5,410
Remarks: Welcome to this spacious and inviting home, thoughtfully designed for comfortable family living and making lasting memories. Step inside to a bright, open-concept living and dining area—perfect for both entertaining guests and everyday relaxation. The kitchen is a true centerpiece, featuring brand-new appliances, a convenient breakfast bar, and a cozy eat-in space. It flows seamlessly into the family room, creating an ideal layout for staying connected with family and friends. Brand new HVAC (2026) Roof (July 2025). The generously sized primary suite offers a peaceful retreat, complete with a walk-in closet. Three additional bedrooms provide ample space and flexibility for family, guests, or even a home office. Enjoy added privacy with no rear neighbors, as the home backs up to a tranquil wooded area—perfect for relaxing or unwinding outdoors. Ideally located in the heart of Kissimmee, this home is just minutes from major highways, shopping centers, dining, and everyday conveniences. This home truly has it all and won’t last long—schedule your private showing today!
Listing is courtesy of: CENTURY 21 CARIOTI (407-566-0555)
Listing Agent: Evagisela Rodriguez (407-566-0555)
2260 SAN VITAL DR #108, KISSIMMEE, FL 34741
$240,00031 Days on yellowkey MLS ID: O6393472
1 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1470 Built: 2006Monthly Fee: $517 Tax: $3,014 (2025)Community: Venetian Bay Village Condo Ph 3Condo
Taxes:$3,014
Remarks: EXCEPTIONAL INVESTMENT OPPORTUNITY OR DREAM VACATION HOME! Welcome to 2260 San Vital Dr #108, a stunning and spacious 4-Bedroom, 3-Bathroom residence perfectly situated in the world-class, guard-gated resort community of Venetian Bay Villages in Kissimmee, Florida. This property offers the perfect blend of comfort, style, and high-income potential in one of Central Florida’s most sought-after short-term rental zones. UNIQUE DUAL-MASTER FLOOR PLAN: This rare and highly functional layout is a favorite among vacationers and large families. It features TWO PRIMARY EN-SUITES: one conveniently located on the first floor for easy access, and a second private master suite on the upper level. This configuration ensures maximum privacy and flexibility for multi-generational living or groups of up to 10 guests. The ground floor boasts an open-concept living and dining area with tall ceilings and plenty of natural light, flowing into a fully-equipped kitchen with a breakfast bar. Two additional guest bedrooms share a third full bathroom, providing a comfortable and balanced living space. RESORT-STYLE LIVING AT ITS FINEST: Living in Venetian Bay Villages feels like a permanent vacation. This Mediterranean-inspired community is meticulously maintained and offers an unparalleled amenity package included in your HOA fee: 24/7 GUARD-GATED SECURITY: Peace of mind with a manned entrance and security patrol. FOUR SPARKLING SWIMMING POOLS: Including a large heated main pool near the clubhouse and three satellite pools throughout the village. ELITE CLUBHOUSE: Featuring a state-of-the-art fitness center, a private movie theater, a game room/arcade, and a business center with high-speed internet. SPORTS & RECREATION: Professional-grade tennis courts, basketball courts, and sand volleyball courts. FAMILY-FRIENDLY: Multiple playgrounds, picnic areas, and scenic walking trails around serene community ponds. STRATEGIC LOCATION IN THE HEART OF THE MAGIC: Location is everything! This property is strategically positioned for maximum occupancy and convenience: MINUTES FROM DISNEY: Less than 10-15 minutes from Walt Disney World Resort main gates. CLOSE TO ATTRACTIONS: Short drive to SeaWorld, Universal Orlando Resort, and Disney Springs. SHOPPER’S PARADISE: Located just around the corner from The Loop Shopping Center, featuring premier retail, a multi-screen cinema, and dozens of popular dining options. EASY TRAVEL: Quick access to Osceola Parkway, John Young Parkway, and I-4. Only 20 minutes from Orlando International Airport (MCO). INVESTOR HIGHLIGHTS: This property is TURNKEY and ready for immediate occupancy or rental. Short-Term Rentals (Airbnb/VRBO) are fully permitted by the association. The HOA is comprehensive and covers: EXTERIOR MAINTENANCE, ROOF REPLACEMENT, LANDSCAPING, TRASH REMOVAL, WATER/SEWER, AND 24-HOUR SECURITY. This significantly lowers the owner's insurance costs and simplifies management. Whether you are looking for a high-performing asset to add to your short-term rental portfolio or a luxurious primary residence where every day feels like a getaway, this Venetian Bay gem is a must-see. Properties with 4 bedrooms and dual suites are in high demand and do not last long on the market. SCHEDULE YOUR PRIVATE TOUR TODAY AND START LIVING THE FLORIDA LIFESTYLE!
Listing Agent: Marcos Urbina (321-388-3150)
653 ROLFE ST, KISSIMMEE, FL 34741
$345,00080 Days on yellowkey MLS ID: S5143119
1 Days Off yellowkey (back on 3/2/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1080 Built: 1986 Tax: $1,939 (2025)Community: EurekaSpa: NoSingle Family
Taxes:$1,939
Remarks: Under contract-accepting backup offers. This beautiful single family home is just a few minutes away to Osceola High School, downtown and Kissimmee Lakefront. Great location close to shopping areas, access to mayor roads and schools. NO HOA, NO CDD. This property is well conserved with an oversize lot ,nice sunny backyard with fruits trees, a large patio, aboveground pool and cover lanai provides plentiful space for gardening and entertaining. The garage is converted into a 4th bedroom but can be easily convert back to a full garage and still have the a garage door. New roof installed in 2023.
Listing is courtesy of: ONE TEAM REALTY (407-530-5006)
Listing Agent: Yolanda Soto Rosado (407-530-5006)
2394 OLD DIXIE HWY, KISSIMMEE, FL 34744
$289,99943 Days on yellowkey MLS ID: O6366826
0 Days Off yellowkey (back on 3/12/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1567 Built: 1958 Tax: $3,253 (2024)Community: Colonial EstatesSingle Family
Taxes:$3,253
Elementary School: Central Avenue Elem
Remarks: Spacious 4-bedroom, 3-bath single-family home on a generous 0.31-acre corner lot with no HOA! This versatile property offers an ideal layout with an eat-in kitchen, inside laundry, and a welcoming front bonus/sitting room perfect for a home office, reading area, or flex space.The split-style floor plan provides comfortable living for multi-generational households, or rental opportunities. Located within a block away from AdventHealth, making it especially appealing for healthcare professionals, traveling nurses, or long-term rental potential. Conveniently close to shopping, dining, and everyday amenities. Zoned for professional office use, offering rare flexibility for buyers seeking a live/work opportunity, small business location, or future investment potential. A unique opportunity for first-time buyers, investors, or entrepreneurs looking for space, location, and versatility.
Listing Agent: Carlethia Burnette (407-970-7902)
2771 SWOOP CIR, KISSIMMEE, FL 34741
$750,00074 Days on yellowkey MLS ID: O6381024
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 2790 Built: 2008Monthly Fee: $215 Tax: $10,227 (2025)Community: AvillaSpa: YesSingle Family
Taxes:$10,227
Remarks: Refined comfort meets Florida lifestyle in this spacious 5-bedroom 5 bathroom home within a gated community overlooking a tranquil pond. Offering 2,790 heated sq ft, the home features a versatile layout ideal for both daily living and entertaining. Bright living areas open to a screen-enclosed paver patio with water views and no rear neighbors, creating a peaceful outdoor retreat. Mature palm landscaping enhances the home’s tropical appeal. Built in 2008 and well maintained, the 5-bedroom, 5-bath layout provides flexibility for guests or work-from-home needs. Community amenities include a pool, sports courts, playground, and walking paths. Conveniently located near shopping, dining, schools, Orlando International Airport, and major attractions. A great opportunity for buyers seeking space, privacy, and location. Schedule your showing today.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Priscila Triska (321-354-5459)
2900 WINDMILL DR, KISSIMMEE, FL 34741
$346,50079 Days on yellowkey MLS ID: S5143171
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1700 Built: 2017Monthly Fee: $233 Tax: $5,328 (2025)Community: Tapestry Ph 2Townhouse
Taxes:$5,328
Remarks: Under contract-accepting backup offers. The only corner townhome currently available in the community, this 3-bedroom, 2.5-bath residence with a rear-entry 2-car garage offers 1,700 square feet of heated living area, making it the largest townhome floor plan in Tapestry. As a corner unit, the home enjoys enhanced privacy with no neighboring unit on one side and additional natural light throughout. The interior features no carpet, with vinyl flooring on the staircase and throughout the second level, delivering a modern, low-maintenance living environment. The bathrooms are finished with quartz countertops, adding a clean and contemporary feel. The primary (master) bedroom includes a private balcony located at the front of the home, a rare feature within the community and an ideal space to enjoy morning coffee, relaxation, or any activity you prefer in a private outdoor setting. The two-car garage is conveniently located at the rear of the home, providing easy access while maintaining a clean and attractive front elevation. Situated within the gated Tapestry community with 24-hour guard service and controlled access, residents enjoy walking trails, fountains, parks, a community pool, and well-maintained common areas. The property is conveniently located near shopping, dining, major highways, and Central Florida attractions, offering an excellent combination of privacy, space, and accessibility.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Jorge Gutierrez Freites (786-800-6493)
2815 W ORANGE BLVD, KISSIMMEE, FL 34741
$285,00018 Days on yellowkey MLS ID: O6396449
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1062 Built: 1958 Tax: $2,691 (2025)Community: Orange Gardens Sec 2Single Family
Taxes:$2,691
Remarks: Prime opportunity in a highly desirable location! Conveniently located just minutes from Old Town, major entertainment, and top hospitals—and only 20 minutes from Walt Disney World—this home is perfectly positioned for strong rental demand. Recent upgrades include a brand-new roof, updated electrical, new flooring, and a newly installed fence, providing peace of mind and low maintenance for years to come.Whether you’re looking to make this your primary residence or add a performing asset to your investment portfolio, this property delivers both value and versatility. Don’t miss this incredible opportunity!
Listing Agent: Amanda Little (407-720-9728)
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