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$995,900
3 Beds 2 Baths Acreage & Unrec SubDv. 34744 Zip Code
FISH LAKE - 175 ft.+/- LAKEFRONT ACREAGE | RENOVATION OPPORTUNITY | DEVELOPMENT POTENTIAL | MULTI GENERATIONAL SPACE RARE OPPORTUNITY to own approximately 4.8 ACRES +/-with 175 +/-feet of TRUE LAKEFRONT on FISH LAKE in Kissimmee. Tucked behind a gated entrance and accessed by a beautiful, long driveway lined with mature natural oak trees, this property offers a level of privacy and tranquility that is increasingly difficult to find. The original 1952 three-bedroom, two-bath home has been lovingly held by the same owner since it was built and offers a unique opportunity for someone ready to bring their vision to life. While the home will likely require a full remodel, there are beautiful original details worth preserving, including wood flooring, cedar ceilings, and a lake-facing sunroom where you can take in the peaceful water views. The property also offers an impressive amount of existing utility and workspace, including a detached metal garage with three bays and a lean-to, a two-car attached carport, plus an additional enclosed bay/workshop attached to the carport. The property is serviced by two wells and two septic tanks. For those looking to create a private family compound or multigenerational retreat, the expansive acreage provides room to explore additional structures, subject to applicable zoning and permitting requirements. For investors and developers, the property carries a Future Land Use designation of LOW DENSITY RESIDENTIAL, with public water and sewer located very close to the property, creating an opportunity worth investigating with the appropriate governmental authorities. Whether your vision is to restore the existing home into a one-of-a-kind lakefront residence, create a private multigenerational property, or explore the property's development potential, 2557 Ames Haven Road offers acreage, lake frontage, privacy, and possibilities rarely found together in Kissimmee.

2557 Ames Haven Road, Kissimmee

$329,900
3 Beds 2 Baths I M Mabbetts Add SubDv. 34741 Zip Code
Virtually Staged. Short Sale. 3 BEDROOMS, 2 BATHROOMS, 1,488 HEATED SQ FT, FULLY RENOVATED HISTORIC BUNGALOW IN THE HEART OF KISSIMMEE! Sale is subject to THIRD-PARTY/LENDER APPROVAL. Built in 1925 and located within Kissimmee's HISTORIC DISTRICT, this charming home combines the character and architectural appeal of an earlier era with the comfort of today's updates. From the inviting COVERED FRONT PORCH and classic bungalow design to the bright, spacious interior, this is a home with personality from the moment you arrive. Inside, you'll find 3 BEDROOMS and 2 FULL BATHROOMS across 1,488 HEATED SQUARE FEET, with an open and comfortable layout featuring a living and dining combination, a WOOD-BURNING FIREPLACE, and updated flooring throughout. The renovated kitchen features QUARTZ COUNTERTOPS, NEWER APPLIANCES, an INDUSTRIAL-STYLE SINK, and plenty of workspace for everyday living and entertaining. Major improvements include a NEWER HVAC SYSTEM (2025), METAL ROOF, UPDATED PVC PLUMBING, UPDATED ELECTRICAL, NEWER WINDOWS, LUXURY VINYL FLOORING, and updated tile bathrooms. The home sits on a crawlspace foundation and also offers a driveway, fenced outdoor space, rear patio area and additional storage shed. Conveniently located near DOWNTOWN KISSIMMEE, shopping, restaurants, major highways, schools and area attractions, this property offers a unique opportunity to own an updated piece of Kissimmee history. SHORT SALE — 3 BEDROOMS, 2 BATHROOMS, 1,488 HEATED SQ FT, FULLY RENOVATED HISTORIC BUNGALOW with a METAL ROOF, 2025 HVAC, UPDATED PLUMBING & ELECTRICAL, QUARTZ COUNTERTOPS and a PRIME KISSIMMEE LOCATION. THIRD-PARTY/LENDER APPROVAL REQUIRED.

725 Mabbette Street, Kissimmee

$1,700,000
5 Beds 4 Baths Lasseters SubDv. 34744 Zip Code
Welcome to the quintessential Florida lakefront lifestyle. Tucked beneath a breathtaking canopy of majestic Southern Live Oaks, this extraordinary 4-bedroom, 3-bath estate—with a detached 1-bedroom, 1-bath guest house—offers approximately 105 feet of shoreline on beautiful Lake Tohopekaliga (Lake Toho) and a setting unlike anything else on the market. Beyond the private wrought-iron gates off Neptune Road, this 1.5-acre estate offers the privacy and freedom of no HOA, allowing you to keep your boat just steps from the water and your RV on its own dedicated pad with electrical hookup. From the sparkling saltwater pool and tranquil koi pond with cascading waterfall to the countless custom features throughout the property, this is a home that truly must be experienced in person. Built with durable concrete block construction and topped with a newer roof, the residence features a timeless blend of hardwood and tile flooring. The heart of the home is a chef’s kitchen designed for both everyday living and entertaining, complete with custom wood cabinetry, a premium Viking vent hood over a six-burner gas cooktop, and sunset views of Lake Toho from the kitchen sink. The outdoor living spaces are equally impressive. Positioned between the pool area and the lakeshore, the custom outdoor kitchen is an entertainer’s dream, featuring a full brick wood-fired oven, brick rotisserie, brick smoker, and expansive concrete cooking area—perfect for hosting everything from intimate family dinners to large gatherings. The spacious primary suite occupies its own private wing of the home and showcases an entire wall of windows framing spectacular lake views. The en-suite bath includes a relaxing garden tub, separate walk-in shower, generous walk-in closet, and ample space to create your own private retreat. The main residence also offers three additional bedrooms, a dedicated office with a closet that could serve as a fifth bedroom, and thoughtfully designed living spaces throughout. Adding even more versatility is the detached guest house, complete with its own private driveway and rear entrance. Featuring an open-concept living and kitchen area, separate bedroom, full bath, and its own HVAC system, it’s ideal for extended family, guests, a private office, or potential rental opportunities. Despite its peaceful, estate-like setting, this exceptional property is conveniently located just minutes from the rapidly growing NeoCity technology district, Osceola Heritage Park, the Florida Turnpike for easy access throughout Central Florida, as well as the Kissimmee and Amtrak SunRail stations for a convenient alternative to highway commuting. This location is also great for the theme park enthusiasts, with over 15 major Disney, Universal, and SeaWorld parks combined within a short drive. For the avid boater/fisherman, you will be delighted to know that your boat- parked on your own dock (with a boat lift)- here on Lake Toho is a part of the Chain-of-Lakes, allowing you to travel through lakes all over Florida, and even to the Atlantic or Gulf of America. Lake Toho also hosts several professional bass fishing tournaments each year. Whether you’re searching for a private waterfront retreat, an entertainer’s paradise, or a place where you can truly enjoy the Florida lifestyle, this one-of-a-kind Lake Toho estate offers an opportunity that’s rarely available.

807 Neptune Road, Kissimmee

$515,000
2 Beds 2 Baths Mirasol At Celebration Condo SubDv. 34747 Zip Code
The best homes don't just offer a place to live—they offer a lifestyle. Welcome to this beautifully maintained third-floor condominium in the highly sought-after Mirasol at Celebration, where elegant living meets the timeless charm of one of Central Florida's most iconic communities. With 2 bedrooms, 2 bathrooms, and the convenience of elevator access, this residence offers the perfect blend of comfort, sophistication, and low-maintenance living. Step inside to an inviting open-concept floor plan where rich wood flooring flows throughout the main living areas, creating a warm and refined atmosphere. At the heart of the home, the beautifully appointed kitchen features gleaming quartz countertops, stainless steel appliances, a spacious eat-in dining area, and a built-in desk—perfect for working from home, meal planning, or keeping everyday life organized. The thoughtfully designed split-bedroom floor plan provides privacy for owners and guests alike, while plush carpeting adds warmth and comfort to each bedroom. The spacious primary suite serves as a peaceful retreat, complete with an oversized walk-in closet and a spa-inspired ensuite bath featuring a double sink vanity, relaxing garden tub, and separate walk-in shower. Beyond your front door, Mirasol offers an impressive collection of resort-style amenities designed to complement your lifestyle. Residents enjoy a heated swimming pool and spa, a 24-hour fitness center, an on-site day spa and salon, a resident clubroom with billiards, a library, business center with conference room, cyber café, concierge service, and beautifully maintained grounds—all just moments from Celebration's charming downtown. From morning walks along Celebration's scenic trails to evenings spent dining at award-winning restaurants, browsing boutique shops, or attending one of the community's many events, every day feels like a getaway. Conveniently located just minutes from Walt Disney World, Orlando International Airport, and major highways, this exceptional residence offers the perfect balance of tranquility, accessibility, and luxury. Whether you're searching for a full-time residence, a seasonal retreat, or a place to simply enjoy life at a slower pace, this exceptional condominium delivers the Celebration lifestyle you've been waiting for. Welcome home to Mirasol at Celebration—where luxury, convenience, and community come together beautifully.

501 Mirasol Circle Unit 313, Celebration

$210,000
2 Beds 1 Baths R P Robinsons SubDv. 34744 Zip Code
Under contract-accepting backup offers. Opportunity meets location in the heart of Kissimmee! This beautifully updated 2-bedroom, 1-bath home offers the perfect blend of modern style, everyday comfort, and exceptional future potential. Inside, you'll find a bright open-concept floor plan featuring a beautifully renovated kitchen with shaker cabinetry, granite countertops, stainless steel appliances, and a spacious butcher block island overlooking the living and dining areas. Updated bathrooms, abundant natural light, and thoughtful finishes create a move-in-ready home you'll love from day one. Step outside to enjoy the oversized, fully fenced backyard shaded by mature oak trees—ideal for entertaining, pets, gardening, or simply relaxing. A large screened front porch adds even more outdoor living space and welcomes you home. Perfectly situated just minutes from Historic Downtown Kissimmee, Kissimmee Lakefront Park, SunRail, shopping, dining, medical facilities, and major roadways including US-192, John Young Parkway, Florida's Turnpike, and SR 417, you'll enjoy convenient access to Orlando International Airport, Lake Nona Medical City, and Central Florida's world-famous attractions. An added advantage is the property's location within the T5-U Mixed-Use Urban Corridor, offering long-term flexibility and investment appeal. Buyers should verify all intended uses with the City of Kissimmee. Whether you're searching for your next home, an income-producing property, or a unique investment opportunity in one of Kissimmee's growing corridors, this property offers outstanding value, location, and potential. Schedule your private showing today!

1418 Bay Street, Kissimmee

$569,000
W A Patricks Add SubDv. 34741 Zip Code
An exceptional opportunity for a professional owner-operator or investor in the heart of Downtown Kissimmee. Whether you're an attorney, insurance agency, title company, CPA, financial advisor, mortgage company, consulting firm, or other professional business, this versatile office building gives you the flexibility to occupy the entire property, operate your business from one side while generating rental income from the other, or lease the entire building as an income-producing investment. Ideally situated on a highly visible corner lot just two blocks from the Osceola County Courthouse, this fully renovated professional office building offers exceptional flexibility, functionality, and long-term value. Completely updated within the last three years, the property features new waterproof laminate flooring throughout, beautifully renovated bathrooms, and a modernized kitchen/break room. The thoughtfully designed layout is ideal for an owner-user or multi-tenant setup, featuring a shared reception and waiting area with its own handicap-accessible restroom, while each side of the building offers a private entrance, conference room, handicap-accessible restroom, and multiple private offices—providing privacy and efficiency for two separate businesses. In total, the property includes three handicap-accessible restrooms. Additional highlights include durable concrete block construction, a private rear parking lot with 10 spaces, and a detached storage building (approximately 10' x 9') complete with electricity and attic storage. Surrounded by Downtown Kissimmee's government offices, restaurants, Sun Rail station, and major roadways, this move-in-ready property offers a rare combination of location, flexibility, and income potential for both owner-users and investors.

104 S Clyde Avenue, Kissimmee

$2,650,000
South Florida Railroad Companys Town Of Kissimmee SubDv. 34741 Zip Code
Rare downtown Kissimmee commercial investment opportunity at 12 E Darlington Ave, Kissimmee, FL 34741, ideally positioned on a highly visible corner lot within the city’s walkable business district. The property features flexible T5-M Mixed-Use zoning, creating potential for retail, restaurant, professional office, residential or mixed-use redevelopment, subject to applicable approvals. This property also presents an excellent leasing opportunity, with the potential to construct up to two additional floors to create multiple income-producing spaces and maximize future rental revenue. Located near the Kissimmee SunRail Station, government offices, restaurants, entertainment and major transportation corridors including US-192 and John Young Parkway, the site benefits from strong surrounding traffic and continued downtown growth. A new planned convention center will be located less than a two-minute drive from the property, offering additional potential exposure from future tourism, business activity and area development. Free public parking is conveniently located directly across the street, adding valuable accessibility for customers, tenants and visitors. This is an exceptional opportunity for an owner-user, developer or investor seeking a prominent downtown location with strong leasing, redevelopment, income and appreciation potential. Renderings and proposed uses are for marketing purposes only; buyer must independently verify zoning, building height, permitted uses, development potential, flood zone and all property information.

12 E Darlington Avenue, Kissimmee

$420,000
4 Beds 3 Baths Neptune Shores 1 SubDv. 34744 Zip Code
This is a rare find. A nearly 2,700-square-foot home on a one-acre lot in a prime location for $420,000, with three ways to make it yours: move in and make it home, renovate it into the dream house you have been picturing, or reimagine the acre as a multi-parcel investment. Sitting right on Neptune Road, this property puts you squarely between St. Cloud and Kissimmee, two miles from the Florida Turnpike and a straight shot to Orlando, Lake Nona, and the coast. Land like this, this close in, does not come up often. The 1964 block home has 4 bedrooms and 3 full baths across roughly 2,658 square feet once you count the additions, and the layout already does the heavy lifting. A screened front porch opens to an oversized living and dining combo, walls of sliding glass to the former greenhouse, an updated kitchen with newer cabinetry and solid counters, and a family room that flows to an enclosed lanai and bonus room. The primary suite has its own en-suite bath and walk-in shower, with two more bedrooms and a second full bath on the main floor. Here is the part investors will circle: a separate upstairs quarters with its own private entrance, full living area, and full bath. Think in-law suite, long-term rental, or a home that helps pay for itself. Three ways to win here: Live in it. The bones are solid and the recent flooring and kitchen work give you a running start. Bring your vision, build real sweat equity, and end up with a one-of-a-kind acre homestead for near starter-home money. Flip it. The updates are already underway and this corridor rewards a clean, thoughtful renovation. Finish what is started and step into instant upside. Build on it. The one-acre parcel (210x200) is already assembled from multiple recorded lots in Neptune Shores and carries ORS1 residential zoning, no HOA, and a Flood Zone X designation. Run your numbers on a tear-down and subdivide into 2 to 4 new single-family lots (buyer to verify zoning, utilities, and lot-split feasibility with Osceola County). Outside is its own selling point. The grounds are a living food forest: avocado, pineapple, guava, and elderberries, plus Golden Chain trees and Rain Lilies. Add an attached one-car garage, a flex room with front and side-yard access, and a storage shed, and the utility matches the charm. Best of all, there is no HOA, so you set the rules on your acre without a board or monthly dues weighing in. Homes with this mix of location, land, and upside tend to move fast. Whether you want to move in, cash in, or break ground, 1730 Neptune Road is a rare canvas. Sold strictly as-is, ready for your vision.

1730 Neptune Road, Kissimmee

$440,000
4 Beds 2 Baths Neptune Rep SubDv. 34744 Zip Code
Discover a rare opportunity to own a versatile property in the heart of Kissimmee’s Historic District, offering endless possibilities for homeowners, multigenerational living, or investors. Situated on an oversized 0.24-acre lot with no HOA, this unique property features a bright, open-concept main living area filled with natural light, plus a flexible bonus room created with a non-permanent wall that can easily be removed to restore the original open layout without affecting the home’s structural integrity. One of the standout features is the detached 1-bedroom, 1-bath ADU (casita) complete with its own private entrance, kitchen, living area —ideal for extended family, guests, a private office, or additional rental income potential. The outdoor space is equally impressive, featuring two storage sheds, and 30-amp RV hookup, perfect opportunity to generate additional income or provide a comfortable private space for visiting family and guests fenced backyard with room to enjoy Florida living. Located just a short walk from Downtown Kissimmee and the beautiful Lakefront Park, you’ll enjoy easy access to waterfront dining, local boutiques, festivals, the marina, walking trails, and year-round community events. The property is also conveniently located near NeoCity, one of Central Florida’s premier innovation and technology hubs, as well as SunRail, major highways, Orlando International Airport, and world-famous attractions. Whether you’re searching for a primary residence, a multigenerational home, or an investment with built-in flexibility, this property offers exceptional value and endless possibilities. Some photos have been virtually staged and/or digitally enhanced for illustrative purposes. Schedule your private showing today!

518 Tohopekaliga Avenue, Kissimmee

$315,000
4 Beds 2 Baths Kissimmee Highlands #4 SubDv. 34741 Zip Code
Exceptional cash-flow opportunity in the highly sought-after 34741 zip code! This property is an investor's dream, currently generating an impressive $2,300/month from the main residence alone. The main home features a beautifully updated 4-bedroom, 2-bathroom layout. Major capital expenditures have already been handled for you: a newer roof (under 5 years), central A/C replaced in 2022, and updated plumbing throughout most of the property. Inside, you will find fully remodeled bathrooms with modern showers, tile flooring throughout, and an extended kitchen fully equipped with stainless steel appliances. The primary suite even includes an independent A/C unit for maximum efficiency. MASSIVE VALUE-ADD BONUS: The expansive backyard features a detached, block-constructed versatile structure with a shingle roof. This flex-space offers a layout that accommodates 2 potential rooms, a bathroom, and a kitchenette/laundry setup. It is the perfect canvas for extended family use, a private home office, or a significant value-add project for the savvy investor. (Buyer to independently verify all room dimensions, zoning, permits, and future use possibilities). UNBEATABLE EXTRAS: The property is equipped with solar panels that dramatically slash electricity costs. Best of all? The seller will completely satisfy the solar balance at closing, delivering immediate, day-one equity and long-term savings to the new owner! The outdoor living space is an entertainer's delight, boasting an oversized covered patio with a fully tiled outdoor kitchen, an independent storage structure, and an extended brick-paver driveway. With NO HOA, moderate taxes, and a prime Central Florida location, this property offers unmatched flexibility and ROI potential. Property sold As-Is. Do not miss this rare opportunity—schedule your showing today!

2615 N Beaumont Avenue, Kissimmee

$765,999
5 Beds 4 Baths Oneal & Osborns Add SubDv. 34741 Zip Code
FULLY REMODELED | NO HOA | PRIVATE IN-LAW SUITE | IN-GROUND POOL | PRIME IN-CITY LOCATION Welcome to 501 W. Sumner St., a rare opportunity to own a beautifully remodeled, move-in-ready residence that combines space, versatility, and modern style in a highly desirable in-city location. Thoughtfully updated from top to bottom, this impressive home offers 5 spacious bedrooms, 4 full bathrooms, and a flexible layout designed to accommodate a variety of lifestyles. From the moment you arrive, the charming front porch and inviting curb appeal set the tone for what awaits inside. Step through the front door and discover bright, open living spaces filled with natural light, contemporary finishes, and a welcoming atmosphere that feels like home. The expansive living area flows seamlessly into the formal dining space, creating the perfect setting for everyday living, holiday gatherings, and entertaining guests. The remodeled kitchen serves as the heart of the home, offering ample cabinetry, generous counter space, modern finishes, and the functionality today’s buyers are looking for. Whether you’re preparing a quiet family dinner or hosting a celebration, this space is designed to make every occasion effortless. One of the property’s most valuable features is the private in-law suite with its own separate entrance. This versatile space is ideal for multi-generational living, extended family, guests, a home office, or potential rental income opportunities. The separate access provides privacy and flexibility that is increasingly difficult to find. The primary living quarters has generously sized bedrooms and well-appointed bathrooms, creating comfortable retreats for everyone in the household. With five bedrooms and four full bathrooms, there is room for large families, visiting guests, hobbies, work-from-home needs, and more. Step outside and enjoy your own private backyard oasis featuring a beautiful in-ground pool, perfect for cooling off on warm Florida days, hosting weekend gatherings, or simply relaxing in the comfort of your own home. The outdoor space offers endless possibilities for entertaining, gardening, or creating your dream backyard retreat. Best of all, NO HOA means greater freedom and flexibility without the additional restrictions and fees often associated with community living. Bring your personal touch and enjoy the ability to truly make this property your own. Conveniently located within city limits, this home places you close to shopping, dining, parks, schools, medical facilities, major roadways, and everyday conveniences while still offering the privacy and space that many buyers desire. Whether you’re searching for a spacious forever home, a multi-generational living solution, or a property with income-producing potential, 501 W. Sumner St. delivers an exceptional combination of location, flexibility, and modern upgrades. This is a truly turnkey opportunity that stands out from the rest. Schedule your private showing today and experience everything this remarkable property has.

501 Sumner Street, Kissimmee

$445,000
3 Beds 3 Baths Fairlawn Manor SubDv. 34744 Zip Code
Motivated Sellers, come see beautifully maintained 3-bedroom, 3-bathroom home in the desirable Fairlawn Manor community of Kissimmee off close to Neptune Road no HOA NO CDD, where comfort, functionality, and convenience come together. From the moment you arrive, you'll appreciate the lush landscaping, majestic oak trees, mature foliage, and inviting curb appeal. Inside, you'll find a spacious, thoughtfully designed floor plan featuring a sunken family room that's perfect for relaxing or entertaining, along with an oversized living room that provides plenty of space for gatherings. The charming kitchen offers timeless appeal with antique-style tile flooring, abundant cabinetry, and generous counter space for meal preparation. A standout feature of this home is its two primary suites, making it an excellent choice for multigenerational living or hosting guests. The main primary suite includes a large walk-in closet and a unique ensuite bathroom, while the second bedroom also features its own private bath. The third bedroom offers flexibility as a guest room, home office, or hobby space and is conveniently located next to a full bathroom with separate guest and private access. Meticulously maintained, this home has been thoughtfully updated with custom 4-inch plantation shutters, double-pane windows, luxury vinyl flooring throughout the main living areas, attic insulation, an energy-efficient hot water heat pump, a whole-home water filtration system, solar panels, Leaf Filter gutters, iron fencing, professionally trimmed trees, a recently serviced A/C with duct cleaning, and a brand-new roof installed in 2026.The oversized two-car garage includes a dedicated workshop area, while the extended driveway provides ample parking for multiple vehicles, a boat, RV, or camper. Step outside to your own private Florida retreat. The screened lanai and expansive paver patio create the perfect setting for outdoor entertaining or quiet evenings at home. The fully fenced backyard offers privacy, mature landscaping, and a storage shed for added convenience. Best of all, this property has 26 Solar Panels offering greater freedom and lower monthly expenses also this location has no HOA nor CDD. Property Ideally located just minutes from Downtown Kissimmee's Lakefront Park, the growing Neo City technology district, shopping, dining, and the Florida Turnpike, this home is also approximately 35 minutes from Walt Disney World. This is a wonderful opportunity to enjoy the best of Central Florida living. THIS HOME FEATURES MANY UPGRADES: Newer Windows also beautiful Shutters in family room and two front bedrooms-2024 Vinyl Flooring-Water filter 2019-Leaf Gutters 2019-Iron Fencing 2019-New Shed 2022-New Roof replaced in 2026- Very Important Solar panels are financed and still have available balance of $44,000 buyer must apply for the balance in order for them to convey with the sale. If buyer declines owners will have them professionally removed. Don't Miss out on this HUGE PRICE REDUCTION!

802 Hastings Drive, Kissimmee

$675,000
3 Beds 4 Baths Acreage & Unrec SubDv. 34746 Zip Code
Under contract-accepting backup offers. Exceptional Opportunity to Own a Fully Renovated Ranch Property on 2.06 Acres in Kissimmee FL! Welcome to this beautifully remodeled ranch-style estate offering the perfect blend of privacy, functionality, and modern upgrades. Situated on 2.06 fully fenced acres with chain-link fencing and a secured electric gate, this versatile property is ideal for those seeking space, flexibility, and country living with convenient access to city amenities. The main residence features 3 spacious bedrooms(TWO MASTERS/suite) and 3.5 bathrooms, thoughtfully updated throughout. Major improvements include a new roof installed in 2021, two HVAC systems installed in 2023 and 2025, and impact-resistant hurricane windows for enhanced safety, energy efficiency, and peace of mind. Adding exceptional value, the property includes a detached guest quarters complete with a private 4-car garage, 1 bedroom, 1 full bathroom, kitchen, and laundry area—perfect for extended family, guests, rental income potential, or a home-based business. Additional features include a septic system installed in 2023, a private well, and the added convenience of access to public water service. Outdoor amenities include a 10' x 10' storage shed, a large chicken coop with capacity for approximately 300 birds, and a variety of mature fruit trees throughout the property. Ideally located just minutes from major roadways, shopping centers, dining, and everyday conveniences, this property offers the freedom of country living with no HOA restrictions. A rare and unique opportunity with endless possibilities. Schedule your private showing today!

1960 Harbor Road, Kissimmee

$1,650,000
Toliga Lake View SubDv. 34741 Zip Code
Positioned along the storied shoreline of Lakeshore Boulevard, this rare income-producing property and location captures the timeless character of Historic Downtown Kissimmee with an address that places lifestyle, recreation, and long-term upside in one compelling package. Comprising six separate income producing apartments, 4 furnished and 2 unfurnished, with a total of 9 bedrooms and 6.5 baths. Property presents a remarkable opportunity for investors seeking immediate rental income or the possibility of a boutique hotel location in one of Central Florida’s steadily evolving waterfront corridors. Originally constructed in 1930, the building carries an architectural presence rarely replicated today blending vintage charm, and an unmistakable sense of place with views and walkability that continue to drive tenant demand. Situated directly across from Kissimmee Lakefront Park, residents enjoy effortless access to the marina, waterfront trails, fishing pier, playgrounds, amphitheater events, dining, cafés, and downtown entertainment all without relying on a car. The building spans over 4,100 square feet on an oversized corner-style lot and features private parking, scenic water and park views, and a setting surrounded by mature trees and historic homes that give the neighborhood its distinctive identity. The property’s layout creates unlimited opportunities. Downtown Kissimmee continues attracting attention for its lakefront revitalization, expanding SunRail connectivity and tourism corridor. Assets with authentic architectural appeal and irreplaceable positioning near the waterfront are becoming increasingly difficult to secure particularly those offering multi-unit versatility near the city’s cultural core. For the discerning investor, this is legacy-style holding in one of Kissimmee's most recognizable districts, where historic ambiance, waterfront surroundings, and enduring rental appeal converge.

304 Lakeshore Boulevard, Kissimmee

$448,000
3 Beds 2 Baths Lake Cecile Park SubDv. 34746 Zip Code
Under contract-accepting backup offers. Wake up to peacefull Lake views, just minutes from Disney. Rare, private waterfront opportunity, on springfeed Lake Cecile with nearly an acre, no HOA, and the ability to build your own boat dock. This renovated 3-bedroom, 2-bath ranch sits on a private ¾-acre lot with 75 feet of lakefront in a secluded community offering peaceful waterfront living with exceptional proximity to shopping, dining, schools, and Orlando’s resort corridor. Recent improvements include new driveway, newer double-paned windows, tankless water heater, plus a beautifully updated kitchen with solid surface countertops, farmhouse sink, stainless steel appliances, and subway tile. Interior features include exposed brick accents, statement ceilings, electric fireplace, wood-look luxury vinyl flooring, and designer finishes throughout. The primary bedroom features French doors with Lake Cecile views, while a bonus flex room currently serves as a home gym and could function as office or studio space. Long private driveway, enclosed garage, mature trees, and classic ranch curb appeal add to the property’s charm. Dockable frontage on Lake Cecile offers future boating and fishing potential. Unique opportunity with no HOA, potential investment opportunity, modern upgrades, and true lakefront living near Disney. Washer, Dryer, Kitchen Island and Blue Barn door in Living room do not convey.

4881 Lake Cecile Dr, Kissimmee

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