Homes for Sale Near Denn John Middle in Kissimmee - 73 homes

Remarks: 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.

Listing is courtesy of: ROMAN'S PRO REALTY LLC (407-610-1970)

Listing Agent: Petie Bilyk (407-361-1415)

Remarks: One or more photo(s) has been virtually staged. ***Live Where Innovation Meets Inspiration — Welcome to NeoCity*** Your new home address is 1617 Mohegan Blvd in Kissimmee, FL, 34744. This townhome is in the gated community of Heritage Run and part of the larger Neo City area. You will be in a Community Building the Future. This well-maintained, 3-bedroom, 2.5-bath townhome is designed with an efficient and logical flow, emphasizing maximizing space, natural light, 9-foot ceilings, kitchen island, soundproofing techniques and functional transitions between rooms to create a comfortable and practical living environment along with community perks in a gated locale. A layout that effectively uses vertical space through features like integrated shelving, tall cabinets, and multi-level storage solutions to store more in less horizontal space. With spacious living areas, a two-car garage, and close proximity to Kissimmee amenities, it’s a strong fit for families, investors, or those seeking a comfortable lock-and-leave lifestyle. Conveniently located between Kissimmee and Boggy Creek Road, Heritage Run offers the ideal blend of location, style, and value. This gated townhome community is just a short walk from Osceola Heritage Park and only minutes from the Florida Turnpike, shopping centers like The Loop and Crosslands, downtown Kissimmee, and Orlando International Airport—putting everything you need right at your fingertips. First Floor: Spacious open layout featuring tiled living areas and eat-in well-appointed kitchen. A convenient half-bath rounds out the ground floor. Second Floor: Three bedrooms, including a master with ensuite privileges, plus two additional rooms and a shared JACK AND JILL bath. Bedrooms have carpeted floors. Additional Features: Inside laundry hook-up, split-bedroom design, walk-in closet(s), energy- efficient thermal windows, two-car garage, covered entry, and screened back patio paired with an extended paver patio creating a generous outdoor space perfect for relaxing or entertaining. Whether you're a first-time buyer, investor, or looking for a low-maintenance lifestyle in a prime Central Florida location, Heritage Run is the perfect place to call home. ****Tomorrow’s Community. Today’s Opportunity.**** Invest Where the Future Is Being Built — NeoCity, Kissimmee.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: Claudia Villarroel (407-952-4779)

Remarks: Charming 2-bedroom, 2-bath villa. Enjoy easy Florida living with a spacious screened porch—perfect for relaxing or entertaining—plus an enclosed area that serves as a convenient storage room. The kitchen features updated cabinets, and newer roof replace in 2025, offering added peace of mind. Conveniently located within minutes of Orlando International Airport, the Florida Turnpike, and SR-417, with major shopping plazas nearby. Plus, you’re just a short drive to Orlando’s world-famous attractions including Universal Studios, Walt Disney World, and SeaWorld.

Listing is courtesy of: FLORIDA PROPERTY HOMES (407-728-5650)

Listing Agent: Luis Cabrera (407-728-4650)

Remarks: Under contract-accepting backup offers. NEW PRICE ENHANCEMENT ALERT! Elevate your living experience with this exceptional retreat in the heart of Lakeside, perfectly balancing space, comfort, and community living. This meticulously maintained, move-ready home reflects the owners’ pride and offers an exceptional lifestyle. It is a haven for families and entertainers alike, blending elegance, comfort, and convenience. The bright, open-concept features soaring ceilings, ceramic tile throughout, a stylish kitchen, a flex room, and other unique features that set this home apart and make it a gem in Central Florida. The space unfolds into a generously sized, open-concept living area, where light cascades through the windows, illuminating the space. This seamless flow invites you to enjoy a comfortable blend, making it the perfect place for relaxation and entertainment. The living room, dining room, flex room, and kitchen create the ideal space for everyday living and entertainment. The kitchen is a true chef's delight, featuring stainless steel appliances, granite countertops, abundant cabinetry, a spacious pantry, and additional seating and dining areas ideal for culinary creations and lively gatherings. The primary suite, thoughtfully located at the rear of the home, is a private oasis with a generous bathroom complete with a luxurious freestanding tub, double vanity sinks, a stand-alone shower, a walk-in closet, and a private owners’ "throne". At the front of the home, two additional guest bedrooms and a full-wall tiled bathroom with a convenient shower provide comfort and privacy for family and guests. Step through the door off the flex area to an open paved terrace overlooking the serene conservation area, perfect for outdoor dining or unwinding after a long day. The backyard invites meditation and relaxation as you gaze at the tranquil views from your home. Nestled in a community, this home offers a resort-style lifestyle with exceptional amenities, including a playground, tennis and basketball courts, a skating rink, and scenic walking trails. Ideally situated 20 minutes from the Orlando International Airport, 15 minutes from Lake Nona Medical and technology hub, 10 minutes from Valencia College, and near major thoroughfares, you can enjoy a short drive to theme parks such as Walt Disney World, SeaWorld, and Universal Studios. And when you're ready for a beach day, the beautiful shores of Cocoa Beach, Tampa, Saint Petersburg, and Clearwater are just a hop, skip, and a jump away, promising sun-soaked fun and relaxation. With easy access to schools, medical offices and hospitals, shopping, restaurants, and major highways, it offers unparalleled convenience and peace of mind. Enjoy your new home, complete with a Vivient security system. This ensures you can move in and start enjoying your new home with complete peace of mind. Don't miss out on this exceptional home that perfectly blends tranquility with access to the best of Central Florida. This is a unique opportunity to own your beautiful home. Schedule your private tour today and discover why this home is the one you’ve been waiting for!

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: Hector Acosta, Pa (407-709-4961)

Remarks: Under contract-accepting backup offers. This charming 4-bedroom pool home, set in a peaceful and well-maintained neighborhood, has so many wonderful features. The living room showcases lovely bay windows, while the family room features soaring ceilings. The primary suite on the main floor includes a spacious double closet and en-suite bathroom. There is also a convenient half bath off the living room for guests. Sliding doors open to a screened-in pool with a new pump, a generous patio ideal for outdoor gatherings, and sizable fenced yard that ensures privacy on a conservation lot that won’t be developed. The eat-in kitchen with nook and island got updated appliances in 2020. Carpeting throughout the home was replaced in 2019. Upstairs, there are three additional bedrooms with generous closets and a fully renovated bathroom from 2022. Best news yet, the roof was replaced in September 2024! The home also offers an attached two-car garage on side of the house with a tucked-away laundry room in between. Located in Kissimmee's Mill-Run Park neighborhood, this property has no HOA and easy access to the Florida Turnpike and Osceola Parkway.

Listing is courtesy of: IMAGINATION REALTY, INC (321-939-1300)

Listing Agent: Patricia Delaney (407-973-8826)

Remarks: JUST LISTED | FULLY REMODELED | NO HOA! Welcome to 501 W Sumner St, a stunning, move-in-ready property located right within city limits!! Features You'll Love! 5 Spacious Bedrooms! 4 Full Bathrooms; Bright Living & Formal Dining Areas, Private In-Law Suite with Separate Entrance (perfect for rental income or multi-generational living. Beautiful In-Ground Pool, Charming Front Porch! NO HOA – freedom and flexibility! This home has been completely remodeled, offering modern finishes, upgraded spaces, and a layout designed for both comfort and functionality. Whether you're looking for your dream home or an income-producing opportunity, this property checks every box. Prime location inside city limits – close to everything!

Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)

Listing Agent: Paola Almonte (407-968-7511)

Remarks: Welcome to this charming 4-bedroom, 2-bath home offering 1,874 square feet of comfortable living space. Designed with both relaxation and entertaining in mind, this home features an open-concept layout that seamlessly connects the kitchen, dining, and living areas. Natural light fills the space, creating a warm and inviting atmosphere throughout. Situated on a spacious lot with a peaceful pond view, you’ll enjoy a serene backdrop right from your backyard. The primary suite includes a walk-in closet and a private en-suite bathroom, providing a perfect retreat at the end of the day. Blending functionality with a touch of nature, this home is ideal for everyday living and ready for its next owner to move right in.

Listing is courtesy of: CENTRIC REALTY SERVICES LLC (407-421-9391)

Listing Agent: Jean Julme (321-280-0658)

Remarks: Under contract-accepting backup offers. Spacious 3-bedroom, 2-bath home featuring high ceilings and an open, airy floor plan with generous living space perfect for everyday living and entertaining. The oversized primary suite offers a walk-in closet and plenty of room to relax. Enjoy outdoor living in the huge fenced backyard complete with a private pool and screened rear porch, ideal for year-round enjoyment. Additional features include a two-car garage and ample yard space for pets, play, or gardening. Conveniently located near shopping, dining, schools, and major roadways.

Listing is courtesy of: LIVE FLORIDA NOW LLC (407-448-7977)

Listing Agent: Dean Erlandson (407-719-5426)

Remarks: CENTRALLY LOCATED NEAR KISSIMMEE DOWNTOWN AND COMMUNITY COLLEGE , 30 MINUTES TO WORLD DISNEY WORLD , SEA WORLD AND UNIVERSAL STUDIOS . CLOSE TO SHOPPING CENTER , REATAURANT , BUS STOP AND MUCH MORE . NEW AC AND NEWLY RENOVATED KITCHEN .

Listing is courtesy of: PROFILES INTERNATIONAL REALTY (321-297-8161)

Listing Agent: Monowar Choudhury (407-791-6579)

Remarks: Great price on this beautifully renovated home, updated just three years ago! A proven, well-maintained rental with excellent income potential, this solid block 3-bedroom, 1-bath home offers side-yard parking behind fencing plus EV (electric vehicle) hookups. Renovated throughout, the home features all 3-year old appliances, ceramic tile flooring, a fully updated kitchen with 42” soft-close cabinets and stunning quartz countertops, recessed lighting, ceiling fans, tankless water heater, updated plumbing and electrical, 5/8” drywall, doors, paint, and updated ductwork. A/C (2017) and maintained. Enjoy outdoor living with a large covered back porch overlooking a refinished in-ground pool (2019), outdoor shower, RV concrete pad with electric, water, and security lighting, and a roof with solar attic vent. Additional upgrades include hurricane-certified double-pane vinyl windows. Ideally located near downtown Kissimmee, close to Osceola Parkway for shopping, schools, parks, major attractions, and easy access to both East and West Coast beaches. Move-in ready and investment-friendly—this one won’t last!

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Brandy Dileonardo (407-460-2107)

Remarks: Welcome to this spacious and versatile 3-bedroom, 2-bathroom pool home located in a desirable gated community. Designed with a thoughtful split floor plan, this home offers privacy and comfort for the whole family. At the front of the home, you’ll find a bright and airy living room and dining room combo—perfect for entertaining or relaxing. The heart of the home features an open kitchen with a cozy breakfast area that flows seamlessly into the family room, creating a warm and inviting space for everyday living. An additional bonus room just off the family room offers endless possibilities—ideal for a home office, playroom, or personal gym. You'll also appreciate the convenience of an inside laundry room. Step outside to your private backyard oasis with a sparkling pool, perfect for enjoying Florida’s sunny days. Located just minutes from Kissimmee Lakefront Park, shopping, sports venues, restaurants, and world-famous theme parks, this home combines comfort, convenience, and fun in one fantastic package. Don't miss your chance to own this beautiful home in a prime Central Florida location! Roof (2018) HVAC (2022)

Listing is courtesy of: KEYSEEKERS REAL ESTATE (727-490-9000)

Listing Agent: Julie Glass (321-436-6881)

Remarks: Move-in ready, completely remodeled. Single family home featuring 3 bedrooms., 2 baths, 2 car garage. The welcoming great room offers plenty of space to entertain family and friends. The fully equipped kitchen has plenty of cabinets, storage space, and granite counter tops. Relax in the privacy and comfort of the spacious Florida room. Bathrooms, granite counter tops, roof, and fence were installed in 2023; a/c installed in 2026, sliding door in Florida room done in 2017, re-piped in 2012, new ducts and windows in Florida room in 2008. Great location offering you easy access to shopping (The Loop), dining, Osceola Pkwy, FL Turnpike, 192, and 441. Check this one out, see it today!

Listing is courtesy of: COLDWELL BANKER SOLOMON (407-348-3322)

Listing Agent: Michael Solomon (407-873-1372)

Remarks: Welcome to this spacious and inviting home, thoughtfully designed for comfortable family living and making lasting memories. Step inside to a bright, open-concept living and dining area—perfect for both entertaining guests and everyday relaxation. The kitchen is a true centerpiece, featuring brand-new appliances, a convenient breakfast bar, and a cozy eat-in space. It flows seamlessly into the family room, creating an ideal layout for staying connected with family and friends. Brand new HVAC (2026) Roof (July 2025). The generously sized primary suite offers a peaceful retreat, complete with a walk-in closet. Three additional bedrooms provide ample space and flexibility for family, guests, or even a home office. Enjoy added privacy with no rear neighbors, as the home backs up to a tranquil wooded area—perfect for relaxing or unwinding outdoors. Ideally located in the heart of Kissimmee, this home is just minutes from major highways, shopping centers, dining, and everyday conveniences. This home truly has it all and won’t last long—schedule your private showing today!

Listing is courtesy of: CENTURY 21 CARIOTI (407-566-0555)

Listing Agent: Evagisela Rodriguez (407-566-0555)