Location: Kissimmee
Keyword(s): Kissimmee Middle
Keyword(s) Middle School: Kissimmee Middle
Do Not Show Listings
658 HUDSON ST, KISSIMMEE, FL 34741
$279,000186 Days on yellowkey MLS ID: S5136343
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1176 Built: 1948 Tax: $1,231 (2024)Community: EurekaSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,231
Elementary School: Kissimmee Elem
High School: Osceola High School
Tax Year: 2024
Middle School: Kissimmee Middle
Remarks: Bring your imagination!!!fixer upper in the best part of city of Kissimmee! Vintage home ready for that buyer that loves a bit of history. room. Great possibilities. Income producer $4,000 a month
Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)
Listing Agent: Paola Almonte (407-968-7511)
4729 WINDWOOD DR, KISSIMMEE, FL 34746
$350,000208 Days on yellowkey MLS ID: S5134904
1 Days Off yellowkey (back on 2/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1382 Built: 1992Monthly Fee: $19 Tax: $4,696 (2024)Community: Windward Cay Unit 1Spa: NoSingle Family
Taxes:$4,696
Elementary School: Central Avenue Elem
High School: Poinciana High School
Remarks: Under contract-accepting backup offers. This beautifully furnished 3-bedroom, 2-bathroom home with its own private pool is designed for comfort, convenience, and year-round enjoyment. From the moment you step inside, you’ll notice the open, flowing layout. The living and dining room combination is filled with natural light and opens directly onto the screened pool deck through sliding glass doors—seamlessly blending indoor and outdoor living. The kitchen is bright and functional, featuring crisp white cabinets, a stainless steel stove and dishwasher, and a breakfast nook wrapped in windows where you can enjoy the morning light. The spacious primary bedroom feels like a retreat with its picture window overlooking the pool, two sets of built-in closets, and an ensuite bathroom with a sink, vanity desk, and separate shower and toilet area. Two additional bedrooms and a second full bath provide plenty of flexibility for guests, work, or hobbies. Wood plank tile flooring throughout the main living areas and baths adds both style and durability. Step outside to your private screened pool, perfectly positioned to capture the morning sun with its east-facing deck. Beyond the screen, a huge extended sundeck offers additional space for lounging, entertaining, or soaking up the Florida sunshine. The fully fenced backyard with white vinyl fencing provides both privacy and a clean, modern finish. Additional features include a two-car garage with washer and dryer, and tasteful furnishings throughout—making the home move-in ready or rental-ready. The location adds incredible value: less than a mile to US-192 for shopping and dining, about 25 minutes to Walt Disney World®, 30 minutes to Universal Studios, and 30 minutes to Orlando International Airport. Even the beaches are within easy reach—just over an hour to the east coast and two hours to the west. Whether you’re searching for a full-time residence, vacation property, or rental investment, this home offers a winning combination of style, functionality, and proximity to everything Central Florida has to offer.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Irena Aistrop (321-443-7535)
3246 RIVER BRANCH CIR #0, KISSIMMEE, FL 34741
$319,99980 Days on yellowkey MLS ID: R4910599
INCREASED by $99 (0.0%) on 04/13/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1542 Built: 2000Monthly Fee: $342 Tax: $1,877 (2025)Community: Sterling Park At StonefieldTownhouse
Taxes:$1,877
Tax Year: 2025
Remarks: Experience the epitome of resort-style living in this meticulously maintained 2-bedroom, 2-bathroom villa located within the exclusive gated community of Sterling Park at Stonefield. The interior radiates modern elegance with soaring ceilings, crown molding, and premium porcelain tile flooring throughout a bright, open-concept layout. At the heart of the home, the chef-inspired kitchen shines with crisp white cabinetry, granite countertops, and stainless steel appliances, seamlessly flowing into a sun-drenched dining area. Retreat to the spacious primary suite, complete with custom shutters and a spa-like ensuite featuring a dual vanity and a frameless glass walk-in shower. Beyond the glass sliders, your private screened-in lanai offers peaceful, unobstructed views of the community’s lush greenspace—perfect for quiet Florida mornings. With the HOA handling lawn and exterior maintenance, you’re free to enjoy the resort-style pool, fitness center, and tennis courts, all while being minutes away from world-class shopping at The Loop and major Orlando attractions.
Listing is courtesy of: MILESTONE FAMILY REALTY LLC (689-265-3683)
Listing Agent: Jeff Joachim (689-304-9330)
8189 SURF ST, KISSIMMEE, FL 34747
$337,90045 Days on yellowkey MLS ID: O6386129
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1394 Built: 2022Monthly Fee: $583 Tax: $7,616 (2025)Community: Rolling Oaks Ph 7Townhouse
Taxes:$7,616
Elementary School: Westside K-8
High School: Celebration High
Remarks: Position your portfolio for success with this premier short-term rental opportunity at 8189 Surf Street in Margaritaville Resort Orlando. Located within one of Central Florida’s most recognized vacation rental destinations, this fully furnished 2-bedroom, 2.5-bath villa offers a true turnkey investment—professionally designed, impeccably maintained, and ready to generate immediate rental income. Thoughtfully designed to maximize guest appeal and occupancy, the villa features a bright open-concept floor plan, soaring ceilings, quartz countertops, upgraded appliances, and premium coastal finishes throughout. The private patio overlooking a tranquil pond creates an inviting outdoor retreat—an amenity highly valued by vacation guests seeking relaxation after a day at the parks. The home is delivered fully furnished with the upgraded Margaritaville Furniture Package, eliminating startup costs and ensuring seamless onboarding into the resort’s rental program. Owners and guests enjoy access to a full suite of resort-style amenities, including multiple pools, on-site restaurants, live entertainment, a fitness center, kids’ club, and the popular Fins Up Beach Club. The resort’s prime location—just minutes from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando—drives consistent year-round tourism demand, while on-site attractions like Island H2O Live! Water Park further enhance guest experience and booking potential. Nearby, Promenade at Sunset Walk offers walkable dining, retail, and entertainment options that increase guest satisfaction and repeat stays. Backed by the strength of the Margaritaville brand and situated in one of the highest-performing vacation rental corridors in the country, this property represents a compelling opportunity for investors seeking strong occupancy, premium nightly rates, and long-term appreciation potential. Capitalize on a proven short-term rental model in a high-demand market—schedule your private showing today.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Nick Whitehouse (407-902-4639)
940 LAKE BERKLEY DR, KISSIMMEE, FL 34746
$436,900212 Days on yellowkey MLS ID: R4909899
Bed: 5 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 2000Monthly Fee: $138 Tax: $3,096 (2024)Community: Lake Berkley ResortSingle Family
Taxes:$3,096
Remarks: A gem of a home overlooking a tranquil water. A 5BR and 2BA Pool Home with 2 Master Suites – Ideal for living or Short-Term Rental! Welcome to this beautifully maintained, located in the highly sought-after Lake Berkley Resort, a 24-hour guard-gated community just minutes from Disney, shopping, and dining. This spacious, move-in-ready home features an open split floor plan, perfect for families, guests, or rental flexibility. The fully equipped kitchen with quality appliances, breakfast bar. The living area opens directly onto a partially covered, screened lanai and private heated pool. Enjoy Lake Berkley Resort’s clubhouse, heated community pool & spa, fitness center, tennis & volleyball courts, basketball court, playground, scenic lake with walking trail and fishing pier. Whether you’re looking for a full-time residence, second home, or income-producing vacation rental, this home has it all. Easy living!
Listing is courtesy of: FREEDOM PROPERTY AGENT LLC (407-530-4600)
Listing Agent: Franc Marrero (321-217-3533)
2720 CLUB CORTILE CIR #A, KISSIMMEE, FL 34746
$249,00018 Days on yellowkey MLS ID: S5146600
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1202 Built: 2007Monthly Fee: $360 Tax: $3,007 (2025)Community: Club CortileCondo
Taxes:$3,007
Elementary School: Floral Ridge Elementary
Remarks: Fully Renovated 3-Bedroom, 2-Bathroom First-Floor Condo with Brand-New Bathrooms in Gated Community – Club Cortile Welcome to this gorgeous 3-bedroom, 2 full bathroom condo located on the first floor in the beautiful gated community of Club Cortile. This is a great opportunity to own a primary residence, second home, or investment property. The entire apartment has been recently remodeled, featuring brand-new bathrooms, upgraded flooring, and a beautiful granite kitchen countertop. The property has been very well maintained by the owner. The layout is highly appealing: upon entering, you’ll find one bedroom on the right and another on the left, along with a shared full bathroom. The kitchen opens to the living room, which leads through sliding glass doors to a screened balcony. The master bedroom, located off the living room, includes a private en-suite bathroom. The gated community offers excellent amenities, including a clubhouse with a fitness center, meeting room, outdoor heated pool, tennis court, and playground—perfect for families and guests of all ages. Conveniently located on US Highway 192, near to shopping and dining, and just minutes from major attractions such as Disney Parks, Universal Studios, and SeaWorld. Easy access to major highways and Orlando International Airport. All appliances, including washer and dryer, are included. Furniture, decorations, and artwork are not included in the sale price. Room measurements are approximate and should be independently verified.
Listing is courtesy of: GILVAN REALTY CORP. (954-825-5722)
Listing Agent: Gilberto Imery (561-927-5412)
2365 RAPOLLO DR, KISSIMMEE, FL 34741
$529,90019 Days on yellowkey MLS ID: O6379468
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2391 Built: 2018Monthly Fee: $167 Tax: $8,804 (2025)Community: Tapestry Ph 4Single Family
Taxes:$8,804
Remarks: One or more photo(s) has been virtually staged. Welcome to 2365 Rapollo Drive, located in the highly sought-after gated community of Tapestry in Kissimmee! This beautifully maintained residence offers the perfect blend of comfort, style, and convenience. Featuring a spacious open-concept floor plan, this home is ideal for both everyday living and entertaining. The chef-inspired kitchen boasts modern cabinetry, granite countertops, stainless steel appliances, and a large center island overlooking the living and dining areas. Natural light fills the home, highlighting the thoughtfully designed layout and generous living spaces. The primary suite offers a with a walk-in closet and an ensuite bath complete with dual vanities and a spacious shower. Additional bedrooms provide flexibility for guests, a home office, or growing needs. Step outside to the fenced backyard space perfect for relaxing evenings or weekend gatherings. Residents of Tapestry enjoy resort style amenities including a clubhouse, sparkling pool, fitness center, and 24hr gated/guarded security. Conveniently located near The Loop shopping center, major highways, dining, and just minutes from world-famous attractions and Orlando International Airport. Don’t miss this opportunity to own in one of Kissimmee’s premier communities. Call to schedule your private showing today! Virtual tour available (English): https://youtu.be/g8VTYhJaErk . Virtual tour available (Spanish): https://youtu.be/MxjL10fnLpE
Listing is courtesy of: AGG REALTY & MANAGEMENT LLC (407-267-7926)
Listing Agent: Amar Guemraoui (407-267-7926)
165 SENECA POINT TRL, KISSIMMEE, FL 34746
$395,00011 Days on yellowkey MLS ID: O6395805
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1804 Built: 2001Monthly Fee: $5 Tax: $6,410 (2025)Community: Indian Point Ph 6Single Family
Taxes:$6,410
Elementary School: Island Village Elementary School
Remarks: MOVE-IN READY! Rare opportunity for first-time buyers or investors, perfectly suited for both long-term living and short-term rental income. Located on a corner lot in the highly desirable Indian Point community, this well-maintained screened pool home stands out with very low HOA fees and access to great amenities including a clubhouse, community pool, playground, and tennis courts. The location is a major highlight, just under 20 minutes to Disney, and less than 35 minutes to Universal Studios and Orlando International Airport, with quick access to HWY 192, plus nearby shopping, dining, hospitals, and entertainment. Inside, the home offers vaulted ceilings, tile flooring in the main areas, no carpet, neutral paint, and an abundance of natural light through large windows and sliding doors, creating a bright, open, and low-maintenance space. The private screened pool adds strong lifestyle and rental appeal, making this home an excellent option as a primary residence, vacation home, or income-producing property in the heart of Central Florida.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
2618 SANTOSH CV, KISSIMMEE, FL 34746
$535,00013 Days on yellowkey MLS ID: O6393947
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2806 Built: 2014Monthly Fee: $397 Tax: $6,942 (2025)Community: Veranda Palms Ph 1CSpa: YesSingle Family
Taxes:$6,942
Remarks: Welcome to 2618 Santosh Cove, located in the highly desired gated resort community of Veranda Palms! This spacious 6-bedroom, 4 full bathroom, and 1 half bath home offers exceptional flexibility whether you're looking for a short-term rental investment, vacation home, or primary residence. Step inside to discover updated luxury vinyl plank flooring (installed approximately 2 years ago) in all previously carpeted areas, while the main living spaces feature durable ceramic tile flooring throughout — with no carpet anywhere in the home. This thoughtful upgrade provides a modern look with easy maintenance, ideal for both everyday living and short-term rental use. The home offers generous living spaces designed for comfort and entertaining, including an open-concept kitchen featuring wood cabinetry, closet pantry, breakfast nook, and ample counter space, flowing seamlessly into the dining and family room areas. The first floor includes a bedroom and full bathroom, ideal for guests or multi-generational living. Upstairs, you'll find additional spacious bedrooms, including a second upstairs bedroom with its own private ensuite bathroom, providing added comfort and privacy for guests or owners. The garage currently features a pool table, creating a fun recreational space while still maintaining the flexibility to be used for parking or additional storage if desired. Step outside to your private screened pool and spa, perfect for enjoying Florida’s sunshine year-round. One of the standout features of this home is no rear neighbors, offering peaceful conservation views and added privacy. Veranda Palms is a gated resort-style community offering fantastic amenities including: Resort-style community pool Clubhouse Fitness center Walking trails Playground Lawn care included in HOA for added convenience and low maintenance living Ideally located just minutes from Walt Disney World, major attractions, shopping, dining, hospitals, and major highways, this home is perfectly positioned for both vacation guests and full-time residents. Currently operating as a short-term rental and being sold fully furnished, this is a turnkey opportunity ready for immediate use or income potential. Whether you're looking for an investment property, vacation retreat, or permanent residence, 2618 Santosh Cove offers flexibility, privacy, and location in one of Kissimmee’s most desirable communities
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Ninzy Acevedo (201-321-4098)
4313 BAY BROOK DR, KISSIMMEE, FL 34746
$599,9991 Day on yellowkey MLS ID: S5147506
Bed: 6 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2399 Built: 1998Monthly Fee: $26 Tax: $4,263 (2025)Community: Creekside Ph 01Single Family
Taxes:$4,263
Remarks: Beautifully maintained home featuring major upgrades and energy-efficient enhancements. The property boasts a metal roof installed in 2019 and a brand-new A/C system (2025), offering peace of mind for years to come. The pool has been resurfaced and includes an electric pool heater, perfect for year-round enjoyment, all within a fully fenced backyard for added privacy. Significant investment has been made with solar panels which will be paid off by the seller. Appliances are in excellent condition and many are newer, including a washer (2025), dryer, stove (2021), and refrigerator (2025) with water filtration system. Appliances may be transferable under warranty for added buyer benefit. This property is a great combination of functionality, efficiency, and outdoor enjoyment—ideal for buyers looking for long-term value and low-maintenance living
Listing Agent: Jennifer Recio (917-891-2028)
2962 PROTAGONIST ST, KISSIMMEE, FL 34746
$515,000250 Days on yellowkey MLS ID: O6333702
2 Days Off yellowkey (back on 4/12/2026)
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2168 Built: 2021Monthly Fee: $550 Tax: $8,286 (2024)Community: Cove At Storey Lake 4Spa: NoTownhouse
Taxes:$8,286
Remarks: Under contract-accepting backup offers. MAJOR PRICE IMPROVEMENT! Now is the perfect time to secure this fully furnished, income-producing vacation home in one of Orlando’s most sought-after resort communities, Storey Lake! INCREDIBLE OPPORTUNITY TO OWN A TOP PRODUCING INCOME PROPERTY in one of the best locations in Orlando! This well decorated home features 5 beds and 4 full baths, with tons of upgrades. quartz countertops, stainless steel appliances, and an open floor plan first floor that leads to a cozy private pool. The rooms are well decorated, with the owner having invested over $60k in upgrades., which definitely bring instant investment income. this vacation home promises not only a luxurious retreat but also a lucrative venture. Storey Lake features incredible amenities. Enjoy the Resort-style pool with a lazy river, waterslides, splash pad, beach volleyball, basketball court, and enclosed turf soccer field. There is an on-site restaurant/tiki bar located at the main pool. In addition to the original resort amenities area, a second area has just recently been completed and this is walking distance from the house. It's equipped with a zero-entry lazy river, pool, splash zone, restaurant, fitness center and playground. Also available for a minimal fee is a mini-golf course and kayak rentals. So many fun things to do here!! Storey Lake Resort is zoned for short term rentals and only 10 minutes away from Walt Disney World, 25 minutes from the Orlando International Airport, and 15 minutes from SeaWorld, Universal Studios and the Premium Outlets!
Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)
Listing Agent: Veronica Li (407-674-0460)
4577 CABELLO LOOP, KISSIMMEE, FL 34746
$780,00072 Days on yellowkey MLS ID: O6377814
Bed: 6 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 3451 Built: 2019Monthly Fee: $431 Tax: $10,844 (2025)Community: Bellavida Ph 2BSingle Family
Taxes:$10,844
Remarks: Welcome to 4577 Cabello Loop, an exceptional 6 bedroom, 6.5 bathroom property located in the highly desirable Bella Vida Resort in Kissimmee. Built in 2019 and purchased directly from the builder, this home has been lightly and occasionally used by owners who reside abroad, resulting in an immaculate, like-new condition. Designed for both comfort and short-term rental appeal, the home features six spacious en-suite bedrooms, plus a convenient half bathroom on the first floor with access to the pool area. The open-concept living space is enhanced by high ceilings and abundant natural light, creating a bright and welcoming atmosphere. The owners further elevated the property with modern upgrades, including high-gloss marble-style ceramic tile flooring, a large kitchen island with seating, and contemporary finishes throughout. The kitchen flows seamlessly into the dining and living areas, ideal for entertaining large groups. Step outside to your private screened-in pool, complete with BBQ grill and outdoor dining area—perfect for enjoying Florida living year-round. The backyard backs onto a peaceful wooded area, offering privacy with no rear neighbors or foot traffic. All bathrooms feature spacious walk-in glass box showers, a highly desirable feature for guests and extended stays, the primary bedroom ensuite features shower heads on both sides. Bella Vida Resort offers gated security, clubhouse, resort-style amenities, and a prime location just minutes from theme parks, shopping, dining, and major highways. This property is ideal as a high-performing vacation rental, second home, or primary residence. A rare opportunity to own a modern, well-maintained home in one of Kissimmee’s most sought-after resort communities. Schedule your showing today!
Listing is courtesy of: SOLARE REALTY LLC (407-460-1994)
Listing Agent: Yulli Okamura (407-928-1028)
3051 GREYSTONE LOOP #106, KISSIMMEE, FL 34741
$255,90090 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)
2979 WHITE CEDAR CIR, KISSIMMEE, FL 34741
$410,0003 Days on yellowkey MLS ID: O6397695
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1942 Built: 2004Monthly Fee: $80 Tax: $4,235 (2025)Community: Windsor Point Ph 2Single Family
Taxes:$4,235
Remarks: Welcome to this 3 bedroom, 2 bathroom home located in a gated community in the heart of Kissimmee, Florida, just minutes from The Loop, a popular shopping, dining, and entertainment destination. Enjoy convenient access to Walt Disney World (approximately 25 minutes) as well as Universal Orlando and Central Florida’s world-famous theme parks, placing you close to everything the Orlando area has to offer. This move-in ready home features a desirable split floor plan with spacious living areas and thoughtful updates throughout. Recent improvements include a 2025 roof, newer AC, and a newer water heater, providing added peace of mind. Inside, you'll find fresh interior paint, new baseboards, and a refreshed front door that give the home a clean and welcoming feel. The layout offers generously sized bedrooms, along with a kitchen and family room combination that creates a comfortable space for gathering and entertaining. A formal living and dining area provides additional flexibility and can easily function as a home office, flex space, additional living area, or hobby room. Residents of this gated Kissimmee community enjoy access to neighborhood amenities including a community pool, playground, and clubhouse, adding to the convenience and lifestyle this location offers. With easy access to shopping, dining, major roadways, and Central Florida attractions, this Kissimmee home offers comfort, convenience, and the opportunity to make it your own. Call to schedule your private showing!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Suzette Berkhalter (407-864-6206)
2671 CHATHAM CIR, KISSIMMEE, FL 34746
$390,00045 Days on yellowkey MLS ID: O6382924
3 Days Off yellowkey (back on 3/9/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1677 Built: 1992Monthly Fee: $46 Tax: $5,557 (2025)Community: Chatham Park At Sausalito Ph 2Single Family
Taxes:$5,557
Elementary School: None
Remarks: Under contract-accepting backup offers. Welcome to your own private retreat in Chatham Park at Sausalito! This beautifully maintained 3-bedroom, 2-bath pool home offers 1,677 heated square feet of comfortable living space and is being sold fully furnished—making it truly move-in or rental ready. Freshly painted in February 2026, the home feels bright, clean, and welcoming from the moment you step inside. Step out back to your screened-in patio and private pool facing the south overlooking a tranquil pond—the perfect setting for morning coffee, evening swims, or simply relaxing while watching Florida’s natural wildlife. The peaceful water view creates a serene atmosphere that both homeowners and guests love. Previously operated as a successful short-term rental, this home has been enjoyed by many guests and offers excellent flexibility. Whether you’re looking for a primary residence, vacation getaway, or income-producing short- or long-term rental, this property checks all the boxes. Ideally located just minutes from U.S. Route 192, providing easy access to Celebration, Old Town, Medieval Times Dinner & Tournament, the Central Florida attractions, numerous restaurants, and shopping at The Loop. If you’ve been searching for a home that offers relaxation, location, and income potential, this pond-front pool home is a wonderful opportunity. Schedule your private showing today and discover the lifestyle waiting for you!
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Greg Staker (407-589-1600)
2801 OAKWATER DR #2801, KISSIMMEE, FL 34747
$325,00025 Days on yellowkey MLS ID: O6391169
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1255 Built: 2007Monthly Fee: $495 Tax: $3,726 (2025)Community: Oakwater Ph 04Condo
Taxes:$3,726
Elementary School: Westside Elem
Remarks: Welcome to 2801 Oakwater Dr, Kissimmee, FL 34747 - This 3-bedroom, 2-bathroom end-unit condo with a 1-car garage is located in the gated Oakwater community, just minutes from Walt Disney World, major attractions, shopping, dining, and Central Florida highways. This 1,465 sq ft condo features a split-bedroom floor plan with the primary suite positioned at the rear for added privacy, including water views, dual closets, and an ensuite bath with shower. The kitchen includes granite countertops, breakfast bar seating, ample cabinetry, and all appliances. The open living and dining areas provide access to a private lanai overlooking the lake. Additional features include an interior laundry closet with washer and dryer, attached garage, and exterior storage. The end-unit location provides added natural light and privacy. Oakwater offers resort-style amenities including a clubhouse, fitness center, game room, community pool, tennis courts, and playground. HOA includes cable TV, internet, and exterior maintenance. This property may be suitable as a primary residence, second home, or investment opportunity. Buyers should verify leasing restrictions and HOA guidelines. Schedule your showing today.
Listing is courtesy of: PLATINUM REAL ESTATE (888-974-7253)
Listing Agent: Scot Hartwell (407-791-8466)
2217 GRAND CAYMAN CT #1237, KISSIMMEE, FL 34741
$159,99994 Days on yellowkey MLS ID: O6370613
REDUCED by $9,001 (5.3%) on 04/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1029 Built: 1999Monthly Fee: $348 Tax: $2,473 (2025)Community: Villas Del Sol At Kissimmee CondoCondo
Taxes:$2,473
High School: None
Remarks: One or more photo(s) has been virtually staged. BACK ON THE MARKET, BUYERS FINANCING FELL THROUGH!! SIGNIFICSNT PRICE REDUCTION!! Lovely 2 bed, 2 bath third floor condo with vaulted ceilings. BRAND NEW WATER HEATER installed March 2026, BRAND NEW AC installed in May 2025. SHORT TERM RENTAL ALLOWED!! New refrigerator 2024. Washer, dryer included in inside utility room and tile throughout. Live in a Resort community situated around two lakes. The Community has a clubhouse with fitness center, two resort-style pools and lighted tennis courts. Minutes away from Disney, Universal & Seaworld, centrally located for Kissimmee and Orlando
Listing is courtesy of: NEXTHOME SUNSHINE REALTY (321-900-2389)
Listing Agent: Lindsy Holland (321-900-2389)
2201 CHAPPELL CT, KISSIMMEE, FL 34746
$364,90060 Days on yellowkey MLS ID: S5143726
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1424 Built: 1992Monthly Fee: $25 Tax: $2,883 (2025)Community: Windward Cay Unit 02Single Family
Taxes:$2,883
Remarks: Updated 3-bedroom, 2-bath home in Windward Cay offering flexibility for a variety of uses. Recent improvements include a 2021 roof, hurricane-impact windows and sliding glass door (2021), A/C (2023), water heater (2023), gutters (2024), and new vinyl flooring (2025). Solar panels installed in 2023 (buyer to verify terms). The remodeled kitchen features granite countertops, wood cabinetry, and stainless steel appliances. Additional features include a fireplace, smart lock system, Ring doorbell, security cameras, and MyQ garage door opener. Located near I-4, Reunion, Champions Gate, shopping, dining, and less than 7 miles from Walt Disney World. Community permits short-term rentals, offering added flexibility. Schedule your showing today.
Listing is courtesy of: RADIUS REALTY GROUP LLC (407-541-0779)
Listing Agent: Geoffrey Lopez, Ii (407-873-5870)
2260 SAN VITAL DR #108, KISSIMMEE, FL 34741
$240,00020 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 is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)
Listing Agent: Marcos Urbina (321-388-3150)
653 ROLFE ST, KISSIMMEE, FL 34741
$345,00069 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
Elementary School: Thacker Avenue Elem (K 5)
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)
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