Location: Kissimmee
Do Not Show Listings
7 WESTCHESTER DR, KISSIMMEE, FL 34744
$434,000392 Days on yellowkey MLS ID: O6309992
1 Days Off yellowkey (back on 4/20/2026)
REDUCED by $5,000 (1.1%) on 04/16/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1786 Built: 1962 Tax: $1,988 (2024)Community: Fairlawn ManorSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,988
Elementary School: Partin Settlement Elem
High School: Osceola High School
Tax Year: 2024
Middle School: Neptune Middle (6-8)
Remarks: Step Into Style & Serenity: A Mid-Century Modern Gem in the Heart of Neptune Corridor Welcome to your private retreat—where timeless mid-century modern design meets the comfort of contemporary luxury. From the moment you enter, this beautifully appointed home envelops you in warmth, elegance, and thoughtful design. Original oak hardwood floors greet you with a rich, organic texture, while the open-concept layout creates a sense of spaciousness far beyond its square footage. The chef-inspired kitchen is a true showstopper, boasting sleek granite countertops, premium cabinetry, a gas range, and a full suite of stainless-steel appliances. Every detail has been considered—from the modern designer lighting that highlights architectural features and original built-ins, to the seamless flow between living, dining, and entertaining spaces. Your primary suite is a sanctuary unto itself. Unwind in the newly renovated, spa-inspired bathroom featuring an oversized walk-in shower, deep soaking tub, and luxe finishes that evoke five-star resort living. French doors open from the bedroom onto your private 10x12 deck—complete with a retractable awning—perfect for sipping morning coffee or winding down with a sunset glass of wine. The secondary bedroom is equally inviting, complemented by a fully remodeled guest bathroom that’s sure to impress visitors. Whether hosting overnight guests or simply enjoying everyday life, this home is designed for comfort and impact. Step outside to an expansive, screened-in back patio ideal for weekend barbecues, family gatherings, or tranquil evenings under the stars. Beyond the patio, an oversized driveway offers ample room for extra vehicles, RVs, or boats, complete with a 30-amp outlet—ready for your next adventure. Situated just a short stroll from Lakefront Park and the vibrant shops and restaurants downtown, you’ll enjoy the rare blend of peaceful retreat and walkable convenience. With easy access to major highways, public transportation, Neo City, and the dynamic Neptune corridor, you’re perfectly positioned for both work and play. Range can work on Electric or Gas propane. Come home to modern comfort, classic charm, and a lifestyle that feels like a permanent getaway. Seller motivated to work on the transaction.The seller contributes toward the buyer's closing costs.
Listing is courtesy of: BRIGHT TRUST REALTY LLC (407-914-0227)
Listing Agent: Antonio Spagnolo (407-914-0227)
665 REGENCY WAY, KISSIMMEE, FL 34758
$374,9903 Days on yellowkey MLS ID: O6415683
Bed: 6 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2417 Built: 1995Monthly Fee: $100 Tax: $1,214 (2025)Community: Poinciana Village 1 Nbhd 3 WestSingle Family
Taxes:$1,214
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Virtually Staged. Beautifully updated home featuring an open floor plan with brand-new flooring throughout and all-new appliances. The spacious layout offers comfortable living and entertaining areas filled with natural light. A separate 2-bedroom, 1-bath in-law suite with its own private entrance provides excellent flexibility for extended family, guests, or rental potential. Additional features include a double-car garage, dedicated laundry room, and modern finishes throughout. Move-in ready and designed for convenience, comfort, and versatility. Don't miss this incredible opportunity!
Listing is courtesy of: VOLKE REAL ESTATE LLC (407-502-2383)
Listing Agent: Gabriela Lauria (407-724-1407)
4894 OLD TAMPA HWY, KISSIMMEE, FL 34758
$399,9008 Days on yellowkey MLS ID: O6414471
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1616 Built: 1979 Tax: $4,704 (2025)Community: Cherub HomesSpa: YesSingle Family
Taxes:$4,704
High School: Poinciana High School
Remarks: Welcome to this beautifully updated pool home in the heart of Kissimmee, offering the perfect blend of comfort, convenience, and investment potential. Located in a rapidly growing area just minutes from Walt Disney World, major attractions, shopping, dining, and entertainment, this property is ideal as a primary residence, first home, vacation home, or investment opportunity. Inside, you’ll find a bright and modern interior featuring fresh paint, recessed lighting throughout, updated fixtures, an updated kitchen, renovated bathrooms, and updated closet doors. The thoughtful upgrades create a move-in-ready home that combines style and functionality. Step outside and enjoy your own private backyard retreat. The resurfaced pool, freshly painted pool deck, and updated pool pump make it easy to enjoy Florida living year-round, whether you’re relaxing with family or entertaining guests. Recent improvements include updated landscaping, fresh interior paint, recessed lighting throughout, updated fixtures, an updated kitchen, updated bathrooms, updated closet doors, a resurfaced pool, freshly painted pool deck, updated pool pump, and many additional enhancements throughout the home. Don’t miss this opportunity to own a beautifully updated property in one of Central Florida’s most desirable and growing locations.
Listing is courtesy of: TBRO REALTY LLC (407-403-4322)
Listing Agent: Jorge Perez Gonzalez (321-525-0204)
4687 FAIRY TALE CIR, KISSIMMEE, FL 34746
$550,000447 Days on yellowkey MLS ID: O6292839
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2166 Built: 2017Monthly Fee: $239 Tax: $7,233 (2024)Community: Storey LakeSingle Family
Taxes:$7,233
Remarks: You'll fall in love with this comfortable four-bedroom home featuring a fully equipped kitchen, separate laundry room, a spacious master bedroom with a closet, and a screened-in porch. The home also features a wide driveway with a two-car garage and a beautiful garden. The community is very well located, just minutes from major supermarkets and shopping, making it very convenient. The gated community features a dog park, playground, community pool, and fitness center. HOA dues are affordable and include cable and internet. *Basic service. Contact us today for a showing. We look forward to working with you!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Edwin Nieves (407-340-0537)
4617 SPARKLING SHELL AVE, KISSIMMEE, FL 34746
$275,000193 Days on yellowkey MLS ID: S5139636
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1683 Built: 2023Monthly Fee: $300 Tax: $4,144 (2024)Community: Cypress Cay Ph 1Townhouse
Taxes:$4,144
Remarks: Short Sale. SHORTSALE Cypress Cay is a beautiful new townhome community offering spacious residences with modern, open-concept designs. This home features 3 bedrooms, 2.5 bathrooms, and a private back patio. The expansive first floor provides the perfect layout for entertaining. Built with energy efficiency in mind, it also includes integrated Smart Home Technology for added convenience.** The HOA offers fantastic amenities such as a pool and cabana, playground, half-court basketball court, dog park, walking trails, and a fiber-optic network delivering up to 1 Gigabit internet speed. The community is ideally located near major highways, including I-4, 417, Osceola Parkway, and 192, providing easy access to International Drive, Disney, and more. Grocery stores, restaurants, and everyday conveniences are just minutes away.
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Andrea Munoz (407-989-2021)
4704 RUBY RED LN, KISSIMMEE, FL 34746
$450,00073 Days on yellowkey MLS ID: O6395863
2 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1978 Built: 2013Monthly Fee: $205 Tax: $5,799 (2025)Community: Crystal Cove ResortSingle Family
Taxes:$5,799
Elementary School: Island Village Elementary School
Middle School: Harmony Middle
Remarks: Exceptional opportunity to own a beautiful 4-bedroom, 2-bath home with a private pool in a prime Kissimmee location, perfect for living, investing, or generating income through short-term rentals. This well-maintained, lightly used home features a spacious primary suite with a large walk-in closet, a functional layout, and bright living areas. Enjoy a screened-in pool area with peaceful water views, ideal for relaxing or entertaining. The community offers great amenities, including a pool, parks, and a clubhouse with a gym. Recent updates provide peace of mind, including a roof installed in November 2024 and an A/C system replaced in 2021. Whether you are looking for a primary residence, vacation home, or income-producing property, this home offers the flexibility to enjoy your time in Orlando while renting it out when not in use, making it a smart and versatile investment in a high-demand area close to shopping, dining, and major attractions.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Gabby Lara (786-757-3852)
3331 WHITESTONE CIR #101, KISSIMMEE, FL 34741
$231,00033 Days on yellowkey MLS ID: S5148826
REDUCED by $8,000 (3.3%) on 06/12/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1495 Built: 2006Monthly Fee: $392 Tax: $4,316 (2025)Community: Flora Ridge Condo Ph 7 Bldg 12Condo
Taxes:$4,316
Elementary School: Floral Ridge Elementary
Middle School: Kissimmee Middle
Remarks: This beautifully maintained first-floor three-bedroom, two-bathroom condo in Kissimmee offers an exceptional opportunity for homeowners and investors alike. Conveniently located near major shopping centers, restaurants, and entertainment, and just minutes from Walt Disney World Resort, this property combines comfort, convenience, and lifestyle. Situated within a secure gated community, residents enjoy peace of mind along with amenities designed for relaxation and enjoyment. The community features elevator access to all floors and a beautifully designed resort-style pool overlooking the lake, creating the perfect setting to unwind. Located on the first floor for added convenience and easy access, this condo is ideal for families, professionals, or investors seeking strong rental potential in one of Central Florida’s most desirable areas.
Listing is courtesy of: ALTIS REALTY (407-401-7447)
Listing Agent: Reynaldo Izaguirre, Pa (407-683-0998)
2743 KISSIMMEE BAY CIR, KISSIMMEE, FL 34744
$649,900102 Days on yellowkey MLS ID: O6386876
REDUCED by $15,100 (2.3%) on 06/11/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2856 Built: 2005Monthly Fee: $195 Tax: $7,062 (2025)Community: Kissimmee BaySpa: YesSingle Family
Taxes:$7,062
High School: Gateway High School (9 12)
Remarks: FOR SALE! Exceptional property in Kissimmee Bay, a true hidden gem in Central Florida. Now featuring stunning twilight photos that bring this home to life after sunset. Schedule your private showing today. Discover Kissimmee Bay, where outdoor living and indoor comfort come together in perfect balance. This meticulously maintained, single-level, four-bedroom, three-bath pool home is nestled along the golf course and preserves of Kissimmee Bay Country Club, making a superb first impression and reflecting true pride of ownership. The front elevation features a tile roof, arched windows, and stone accents. The expansive paver driveway provides ample space for parking and adds to the home’s impressive presence. This home has been tastefully upgraded throughout with quality finishes, desirable features, and has an expertly designed floor plan. This home, filled with natural light, high ceilings and triple sliding glass doors, offers a formal dining room, a living room overlooking the pool and golf course-preserve view, a flex room perfect for a home office, and an open concept kitchen with a family room that seamlessly connects to the outdoor pool lanai. The fabulous, updated kitchen is bright, open and inviting. Features include a large island and quartz countertops, a tile backsplash, electric cooktop, an LG refrigerator, an oven and microwave combo, glass cabinet accents with lighting, and a beautiful neutral light color palette. The primary suite is spacious with a coffered ceiling, two walk-in closets, and a new spa-inspired primary bathroom featuring a modern, seamless epoxy floor, a beautiful open shower and custom cabinetry. The home layout also includes a Jack & Jill bedroom and a separate guest suite with direct access to a pool bath providing privacy. Additional features include a laundry room with sink, a two car garage and attic storage space. Enjoy an additional 900 sq. ft. of outdoor living with an extended screened-in lanai, heated pool and waterfall spa, a SunSetter electric awning, and covered patio offering privacy for entertaining. The view from the lanai is tranquil and picturesque, framed by mature trees and overlooking the golf course in the distance. This established community of Kissimmee Bay Country Club offers exceptional value and an active lifestyle. HOA fees include high-speed internet and cable TV, and free irrigation to maintain lush landscaping year-round. Residents appreciate the strong sense of community with regular social events and recreational amenities of golf, tennis, basketball, pickleball and strolling along well shaded sidewalks. Just outside the community entrance is a scenic bike path extending 12 miles round-trip to St. Cloud Lakefront Park. The community also offers on-site RV, boat, and jet ski storage (for a nominal annual fee) and direct access to East Lake Toho at the KB marina. Conveniently located approximately 30 minutes from Disney, Universal, and Orlando International Airport, Kissimmee Bay offers an ideal Central Florida location. This exceptional home perfectly embodies the Florida lifestyle!
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Rose Kemp (407-709-1996)
2403 SILVER PALM DR, KISSIMMEE, FL 34747
$280,00044 Days on yellowkey MLS ID: S5149029
REDUCED by $9,900 (3.4%) on 06/09/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1440 Built: 2003Monthly Fee: $210 Tax: $2,895 (2025)Community: Windsor Palms Twnhms Ph 3ATownhouse
Taxes:$2,895
Remarks: Beautiful 3-bedroom, 3-bathroom home offering comfort and flexibility in a prime location—less than 3 miles from Walt Disney World! This well-designed layout features one bedroom and a full bathroom on the first floor, perfect for guests or multi-generational living. Enjoy Florida living in your screened-in courtyard—ideal for relaxing or entertaining year-round. Located in a resort-style community with incredible amenities, including a saltwater pool, splash pad, tennis and volleyball courts, clubhouse with gym and movie theater, tiki bar, convenience store, daily valet trash, and 24-hour guard-gated security. HOA includes cable and internet for added value.Perfect as a primary home, vacation getaway, or short-term rental investment with low-maintenance living and endless potential.
Listing is courtesy of: LA CASA LUXE REALTY (407-978-1088)
Listing Agent: Issanell Valdez Javier (407-978-1088)
2675 HILLIARD CT, KISSIMMEE, FL 34744
$575,0009 Days on yellowkey MLS ID: S5151356
3 Days Off yellowkey (back on 6/12/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2614 Built: 1999 Tax: $3,961 (2025)Community: Hilliard PlaceSingle Family
Taxes:$3,961
Remarks: Situated on a full 1-acre lot in the Hilliard Place community, this 4-bedroom, 3-bath pool home offers the perfect blend of space, privacy, and convenience in a sought-after Kissimmee location. Tucked away on a quiet cul-de-sac, the property welcomes you with an extended driveway, generous outdoor space, and a setting that feels private while still being close to everything Central Florida has to offer. As you enter the home, you're greeted by a formal dining area to the left that connects seamlessly to the kitchen, while an additional flex space to the right provides endless possibilities as a second living area, home office, playroom, or hobby space. The layout then opens into the heart of the home, where natural light fills the main living areas and creates a bright, inviting atmosphere throughout. The spacious kitchen is designed for both everyday living and entertaining, featuring matching built-in appliances, a cooktop, abundant cabinetry, extensive counter space, a center island, and a convenient breakfast bar that overlooks and connects to the main living room, creating the perfect space for casual dining and gathering. The open design makes it easy to stay connected whether you're preparing meals, hosting guests, or enjoying time with family. The thoughtfully designed split-bedroom floor plan provides added privacy, with the primary suite situated on one side of the home and the remaining bedrooms on the opposite side. The spacious primary retreat features a large ensuite bathroom complete with dual vanities, a garden tub, separate shower, and ample storage. The additional bedrooms are generously sized and offer a similar feel and functionality. Step outside to enjoy Florida living at its finest with a screened-in heated saltwater pool reaching approximately 8 feet in depth, perfect for relaxing, entertaining, or cooling off on warm Florida days. One of the secondary bathrooms also serves as a convenient pool bath, making outdoor gatherings even more enjoyable. The covered lanai overlooks a spacious backyard with plenty of room to spread out and enjoy the outdoors. One of the standout features of this property is the generous distance between neighboring homes, offering a level of privacy that is increasingly difficult to find. The fully usable acre provides endless possibilities for outdoor activities, gardening, future additions, workshops, or simply enjoying the extra space and peaceful surroundings. The property also features an existing chicken coop, adding character and functionality for those who enjoy raising chickens or creating their own backyard homestead. For added peace of mind, the home is equipped with hurricane shutters for every opening, helping provide protection and preparedness during storm season. Located within a small, established community known for its friendly neighbors and welcoming atmosphere, you'll enjoy the perfect balance of privacy and community. Conveniently located near Boggy Creek Road, Lake Nona, Medical City, Orlando International Airport, major highways, shopping, dining, and everyday conveniences, this property offers the opportunity to enjoy peaceful living without sacrificing accessibility. Whether you're looking for room to spread out, a private pool home, or the rare combination of acreage and convenience, this property is one you won't want to miss.
Listing is courtesy of: EXP REALTY LLC (407-846-0940)
Listing Agent: Steve Pugh (407-846-0940)
8810 GRAND PALMS CIR #A, KISSIMMEE, FL 34747
$230,00023 Days on yellowkey MLS ID: O6410146
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1245 Built: 2002Monthly Fee: $331 Tax: $3,104 (2025)Community: Grand Palms Condo 4 Ph 1Condo
Taxes:$3,104
Elementary School: Westside K-8
High School: Celebration High
Middle School: Celebration K-8
Remarks: Virtually Staged. Walk through the front door and the space opens up — nearly 1,300 square feet of first-floor living that feels larger than the number suggests, with natural light pouring in from every direction and a layout that flows easily from the foyer through the dining and living areas out to the screened porch. The home has all new window treatments and fresh paint throughout. The smart split floor plan keeps the primary suite separate from the secondary bedrooms for added privacy. The updated kitchen features white shaker cabinets, new stainless appliances, and a large pantry with room to actually stock up. The bathrooms have been refreshed, and the screened porch off the living room gives you a spot to settle in with morning coffee or wind down after a day out. Washer and dryer are included. Step outside and you're a few feet from the community pool and the tennis and pickleball court. Zoned for short-term rental, this one is ready to drop straight into an investor's portfolio, or settle into as a primary home or seasonal getaway. Location is the headline here. You're ten minutes from Walt Disney World, eight minutes from Sunset Walk dining and entertainment, seven minutes from H2O Live water park, and twenty-five minutes from Universal Studios. US-192 and I-4 are right there, putting every Central Florida attraction inside an easy drive. For STR investors targeting the Disney crowd, the math here writes itself. The HOA covers exterior maintenance including the roof. Three bedrooms, two baths, pool-and-court views, STR-ready, ten minutes from the Magic. Come see it.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Brad Young (407-897-5400)
1823 SUMMER SERENITY DR, KISSIMMEE, FL 34744
$379,00058 Days on yellowkey MLS ID: O6400356
REDUCED by $16,000 (4.1%) on 05/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1900 Built: 2022Monthly Fee: $26 Tax: $6,999 (2024)Community: Tohoqua Ph 4ASingle Family
Taxes:$6,999
Remarks: Rare oversized corner-lot home in the Tohoqua community. This newer construction 3-bedroom, 2.5-bath home with a 2-car garage is situated on a premium oversized corner lot, offering expanded outdoor space, enhanced privacy, and standout curb appeal. Corner lots are limited in availability and typically command higher premiums, making this a rare and desirable opportunity within the community. The positioning also provides a more open, airy feel compared to standard interior homesites. Inside, the home features a thoughtfully designed open-concept layout with a spacious gathering room and a well-appointed kitchen, ideal for both everyday living and entertaining. A versatile first-floor flex room adds functionality and can be used as a home office, playroom, or additional living space. Upstairs, the private owner’s suite is complemented by additional bedrooms, with a layout that provides separation from the main living areas for added comfort and privacy. Located in the sought-after Tohoqua community, residents enjoy resort-style amenities including a clubhouse, tennis courts, parks, walking trails, and access to Lake Tohopekaliga. Conveniently located near the Florida Turnpike and US-192, with easy access to Orlando, shopping, dining, and surrounding areas. Aggressively priced for a premium corner-lot home, presenting a standout value and an exceptional opportunity for buyers seeking space, privacy, and long-term upside.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
4103 SPITFIRE AVE, KISSIMMEE, FL 34741
$203,50083 Days on yellowkey MLS ID: O6384633
0 Days Off yellowkey (back on 5/21/2026)
REDUCED by $500 (0.2%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 930 Built: 1984Monthly Fee: $62 Tax: $2,566 (2025)Community: Waterway VillageVilla
Taxes:$2,566
Remarks: Under contract-accepting backup offers. Welcome to your perfect turn-key opportunity in the heart of Kissimmee, Florida! Located at 4103 Spitfire Avenue in the desirable Waterway Village community, this freshly renovated 2-bedroom, 2-bathroom villa offers 930 square feet of bright, modern living with low-maintenance ease and unbeatable convenience—just minutes from world-famous theme parks, shopping, dining, and major highways. As you step inside this move-in-ready gem, you’re greeted by the fresh feel of newer flooring throughout, creating a clean, contemporary atmosphere that flows seamlessly from the updated kitchen and dinette into the spacious living area. The fully refreshed kitchen features sleek finishes and ample space for everyday meals or entertaining, while the two beautifully updated bathrooms provide modern comfort for you and your guests. The open-concept layout makes this home feel bright, welcoming, and perfectly sized for comfortable living. This property shines with major recent upgrades that deliver peace of mind and long-term savings: a brand-new roof and a full AC system replacement completed in November 2023. No major expenses on the horizon—just move in and enjoy! Now vacant and ready for its next chapter, this villa was previously renting for $1,700 per month, making it an outstanding choice for both owner-occupants seeking an affordable starter home or smart investors looking for proven income potential. Waterway Village offers community amenities including a sparkling pool, with low HOA fees that handle much of the exterior maintenance, so you can spend your time enjoying Florida living instead of upkeep. Whether you’re dreaming of your first home, a carefree vacation retreat, or a hassle-free rental investment, this charming villa in a peaceful, park-like setting with mature trees and professional landscaping is the ideal blend of value, location, and modern updates. Don’t wait—schedule your private showing today and secure this beautifully renovated Spitfire Avenue home before it’s gone. Start living the convenient Central Florida lifestyle you’ve been waiting for!
Listing is courtesy of: REALTY OF AMERICA (321-732-5369)
Listing Agent: Rafael Ceja Llc, Jr (407-779-2000)
2521 MARSHFIELD PRESERVE WAY, KISSIMMEE, FL 34746
$369,90050 Days on yellowkey MLS ID: S5148608
1 Days Off yellowkey (back on 6/12/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2122 Built: 2012Monthly Fee: $12 Tax: $5,617 (2025)Community: Concorde Estates Ph 2BSingle Family
Taxes:$5,617
Remarks: Welcome home to this beautifully maintained 4-bedroom, 2-bath residence offering both comfort and privacy! Freshly painted on the exterior, this home features great curb appeal with mature landscaping and a charming covered front porch perfect for relaxing. Step inside to find an open and spacious split floor plan with tile flooring throughout the main living areas and abundant natural light. The kitchen is designed for both function and entertaining, featuring granite countertops, stainless steel appliances, dark wood cabinetry, breakfast bar seating, and plenty of prep space. The private primary suite offers dual vanities, a garden tub, separate walk-in shower, and a walk-in closet. Additional bedrooms provide flexibility for family, guests, or a home office, while the large interior laundry room adds extra convenience. The oversized dining area flows seamlessly to the screened lanai where you can enjoy peaceful preserve views with no rear neighbors. Nature lovers will appreciate the eagle’s nest located along the backyard tree line, offering a unique opportunity for bird watching right from your own backyard. Conveniently located near shopping, dining, schools, and major roadways. Schedule your private showing today!
Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Christina Laidley (954-579-3742)
2827 SHADOW WOOD CT, KISSIMMEE, FL 34746
$524,99010 Days on yellowkey MLS ID: O6413557
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2736 Built: 1987Monthly Fee: $31 Tax: $2,589 (2025)Community: Pleasant Hill Lakes Unit 9Single Family
Taxes:$2,589
Elementary School: Bellalago Charter Academy (K-8)
High School: Liberty High
Middle School: Bellalago Charter Academy (K-8)
Remarks: Welcome to a home designed around the way Florida living was meant to be enjoyed. From the moment you step through the front door, your eyes are immediately drawn through a dramatic wall of glass to the sparkling screened pool beyond, creating a breathtaking first impression that sets the tone for everything this exceptional custom-built residence has for you. Perfectly situated on an expansive .52-acre homesite in the sought-after Pleasant Hill Lakes community, this is the rare property that combines privacy, character, and space in a way that newer cookie-cutter neighborhoods simply cannot. Lovingly maintained by its original owners and recently refreshed with numerous updates, this 3-bedroom, 3.5-bathroom home showcases timeless architecture centered around seamless indoor-outdoor living. Natural light fills the home through oversized sliding glass doors, while soaring ceilings create an open and airy atmosphere throughout the main living spaces. At the heart of the home, the updated kitchen features beautiful new cabinetry and flows effortlessly into the breakfast nook and spacious family room, creating the perfect gathering space for everyday living and entertaining. A charming fireplace anchors the living area, adding warmth and character to the home's inviting ambiance. Formal dining and a dedicated office provide flexibility for hosting guests, working remotely, or enjoying additional living space. The primary suite serves as a private retreat, offering an oversized bedroom with vaulted ceilings, direct pool access through sliding glass doors, a large walk-in closet, and a beautifully renovated spa-inspired bathroom complete with dual vanities, a dedicated makeup station, a soaking jacuzzi tub, and a separate walk-in shower. Step outside and discover the lifestyle that truly sets this home apart. The oversized screened pool enclosure creates a private backyard oasis, complete with a dedicated pool bath and a newly refinished pool deck. Whether hosting weekend gatherings, enjoying your morning coffee, or unwinding under the Florida sunshine, this outdoor living space was designed to be enjoyed year-round. Recent improvements provide peace of mind and modern appeal, including a new HVAC system (2026), second HVAC system (2023), newer roof (2023), new kitchen cabinetry, renovated primary bathroom, fresh interior and exterior paint, new flooring in the primary bedroom, updated landscaping, and a refinished pool deck. The washer, dryer, and refrigerator are all included, making this home truly move-in ready. Additional highlights include an oversized 8+ car driveway, spacious 3-car garage, mature landscaping, and ample room for boats, recreational vehicles, or additional parking. Located within the established Pleasant Hill Lakes community, residents enjoy larger estate-style homesites, mature oak trees, custom architecture, wide streets, and a remarkably low HOA. Conveniently located near Disney, Lake Nona, Orlando International Airport, Downtown Kissimmee, The Loop, major highways, shopping, dining, and entertainment, this location offers an ideal balance of privacy and convenience. Homes offering this combination of land, architecture, updates, pool-focused design, and location rarely become available. This is more than a home. It is an opportunity to enjoy the space, character, and Florida lifestyle today's buyers are searching for but seldom find.
Listing is courtesy of: LIVE MVRK LLC (407-756-4563)
Listing Agent: Jared Dunn (407-493-8872)
8711 ROCKINGHAM TER #A, KISSIMMEE, FL 34747
$239,000462 Days on yellowkey MLS ID: O6288201
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1357 Built: 1998Monthly Fee: $300 Tax: $3,452 (2024)Community: Villas At Island Club Ph 2Condo
Taxes:$3,452
Remarks: Welcome to 8711 Rockingham Ter, Unit A — a fully furnished, move-in ready condo just minutes from Walt Disney World, Universal Studios, and Orlando's top attractions. Located in a gated community within Villas at Island Club, this updated 3-bedroom, 2-bath home offers strong potential for short-term rental income or a low-maintenance Florida retreat. Recent updates include new flooring in the kitchen, living, and dining areas, fresh paint throughout, and new ceiling fans. The kitchen features granite countertops, updated cabinetry, and a new refrigerator, washer, and dryer. A new AC unit adds to year-round comfort. The community offers a pool and gated access, with convenient proximity to dining, shopping, and entertainment. Whether you're growing a rental portfolio or looking for a vacation property, this home is worth seeing. Schedule a showing today.
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Jose Gomez (407-910-3537)
3869 SHORESIDE DR, KISSIMMEE, FL 34746
$715,000370 Days on yellowkey MLS ID: R4909422
REDUCED by $20,000 (2.7%) on 06/12/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3583 Built: 2016Monthly Fee: $310 Tax: $9,315 (2024)Community: Bellalago Ph 4KSpa: NoSingle Family
Taxes:$9,315
Remarks: Major Price reduction for this Magnificent updated property located in the fabulous gated Bella Lago Resort, the property comes with its own private boat dock ramp and located on the chain of lakes, access to many wonderful water areas is possible, the property has real hardwood Floors flooring throughout, recently completely re-modeled. Quartz surfaces throughout, incredible open plan kitchen overlooking water view with center island, solid quartz surfaces. Multiple quartz work surfaces. Full length cabinets with oversize crown molding. Multiple inbuilt ovens and inbuilt ceramic hob. Walk in wine cellar with fitted wine racks and 2 wine coolers glass barn style sliding door. Utility room with French deep porcelain sink and washer dryer and multiple storage cabinets. Walk out balcony on first floor led recessed lighting, high quality cabinets with crown molding tops, built in wine cellar, Large screened Florida room with Art Deco cooling ceiling fans and facing the water Too many upgrades to list, the property interior was professionally designed and undertaken.
Listing is courtesy of: ZAINS REALTY, LLC (407-994-3171)
Listing Agent: Phil Dinnis (407-908-0275)
8825 RHODES ST, KISSIMMEE, FL 34747
$675,0003 Days on yellowkey MLS ID: S5151659
Bed: 8 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4041 Built: 2016Monthly Fee: $563 Tax: $11,485 (2025)Community: Windsor At Westside Ph 1Spa: YesSingle Family
Taxes:$11,485
Middle School: Horizon Middle
Remarks: Welcome to 8825 Rhodes Street, 4041sqft beautifully maintained and fully furnished 8-bedroom, 6-bathroom home located within the highly sought-after gated Windsor at Westside Resort community. Designed for comfort, luxury, and entertainment, this spacious property features both upstairs and downstairs living areas, providing plenty of room for family and guests to relax and unwind. The open-concept kitchen showcases elegant granite countertops, ample cabinetry, and plenty of space for gathering and entertaining. Step outside to your private screened-in heated pool and covered lanai, creating the perfect setting for outdoor dining, family gatherings, or weekend BBQs while enjoying Florida's beautiful weather year-round. The converted garage has been transformed into a fun-filled game room, creating an additional entertainment space that guests and family members of all ages will enjoy. Whether you're searching for a primary residence, vacation home, or investment opportunity, this property offers exceptional flexibility and value. Residents enjoy access to all Windsor at Westside Resort amenities through the HOA, including a resort-style pool, clubhouse, fitness center, sports courts, playgrounds, and more. Ideally located approximately 8 miles from Walt Disney World Resort, this home offers convenient access to world-famous attractions, shopping, dining, golf, and major highways while providing the security and lifestyle of one of Central Florida's premier gated resort communities.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Jaden Ortiz (352-872-8181)
304 BASS LN, KISSIMMEE, FL 34759
$299,900245 Days on yellowkey MLS ID: O6351826
2 Days Off yellowkey (back on 4/26/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1501 Built: 2025Monthly Fee: $89 Tax: $193 (2024)Community: Poinciana Nbrhd 02 East Village 07Single Family
Taxes:$193
Elementary School: Laurel Elementary
High School: Haines City Senior High
Middle School: Lake Marion Creek Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Back on the market! New Construction! Move-In Ready. Bright, open vibes from the moment you walk in. The kitchen is the star: a huge quartz island for cooking, snacking, and hanging out, plus stainless appliances, quartz counters, and cool pendant lights. The primary bath is clean and modern with dual vanities, and the whole home has sleek LVP floors. The sliders open to a roomy back porch, perfect for grilling and chilling on an almost ½ acre fully sodded lot.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Fernando Lopes (407-955-9555)
4722 ORMOND BEACH WAY, KISSIMMEE, FL 34746
$409,90050 Days on yellowkey MLS ID: O6402310
REDUCED by $5,100 (1.2%) on 05/23/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1636 Built: 2003Monthly Fee: $149 Tax: $3,996 (2025)Community: Terra Verde Villas Ph 1Townhouse
Taxes:$3,996
Elementary School: Knights Point
Remarks: FULLY REMODELED KITCHEN!! Stunning lakeview townhome in Terra Verde Resort with private pool! AIR BNB friendly! Welcome to this beautifully maintained 4 bedroom, 3 full bath end unit townhome located in the highy sought after Terra Verde Resort in Kissimmee one of Central Florida's premier gated, short-term rental friendly communities. Whether you're looking for a primary residence, vacation home or income producing investment, this property offers the perfect blend of location, comfort and profitability. As you enter, you are greeted by abundant natural light and a thoughtfully designed layout featuring a fully remodeled modern kitchen with quartz countertops, stylish backsplash, stainless steel appliances, wine fridge and elegant designer cabinet door handles. A guest bedroom is conveniently located on the main floor with a fully remodeled bathroom along with the laundry room and under stair storage. Upstairs, you'll find a spacious primary suite with a beautifully remodeled en-suite bathroom along with two additional bedrooms and fully remodeled guest bathroom with a tub. AC replaced in 2018. Step outside to your own private oasis a screened-in pool overlooking serene lake views and just steps from the community pool and amenities offering ultimate convenience for both owners and guests. Terra Verde is a gated community with 24 hour security guard and offers award winning amenities, heated zero-entry pool, hot tub, mini golf, basketball, sand volleyball, tennis, playground, ping pong, shuffleboard, lakeside hammocks, adult only outdoor lounge, outdoor fitness equipment, cornhole, Terra Verde Tiki Bar & Grill, walking trails and scenic lake. The impressive 6,000 sq ft clubhouse features concierge services, movie theater, game room, fitness center, sauna, lounge, complimentary coffee and ATM. The resort also features an electric car charging station. Ideally located just minutes from Walt Disney World, Old Town Kissimmee, Island H20 Water Park, Sunset Walk, major highways, shopping, dining and more. Don't miss this incredible opportunity-schedule your private showing today and take it to the FINISH Line!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Monica Vega Stiskin, Llc (917-405-7132)
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