Homes for Sale Near Denn John Middle in Kissimmee - 74 homes

Remarks: Under contract-accepting backup offers. A rare opportunity part of historic Downtown Kissimmee with NO HOA. This charming well kept 2 bedroom 2 bath property is on a fully fenced lot with a huge extended Driveway that easily fits multiple vehicles meaning bring your boat, trailer, or work trucks with no restrictions. NO HOA! Great starter home that checks all the boxes. Roof was replaced in 2019 and air conditioning unit was replaced in 2025. Location is everything, and this one is unbeatable. Just a few blocks from Downtown Kissimmee, you’re minutes from Lake Toho's scenic waterfront, Kissimmee Lakefront Park, restaurants, Broadway Pizza, boutiques, the Kissimmee Valley Farmers Market, year-round community events, seasonal festivities, bus depot and Sun Rail access for easy commuting. Easy access to Disney, major roads and highways, the Turnpike and the hospital is just a few block away. Opportunities like this in Downtown Kissimmee don’t come around often so HURRY before it's gone!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Lucy Rivera (407-922-1953)

Remarks: Under contract-accepting backup offers. Welcome to the newly renovated 2628 Milton Ave, a beautifully updated block home located in the established community of Kissimmee Highlands! Situated on an oversized lot just shy of ¼ acre with NO HOA, this move-in ready property offers the perfect combination of modern upgrades, functionality, and value. Completely renovated in April 2026, this home has undergone an extensive transformation from top to bottom. Major improvements include a BRAND NEW ROOF WITH ALL NEW PLYWOOD, COMPLETE ELECTRICAL REWIRE, NEW WATER HEATER, NEW FLOORING THROUGHOUT, FULLY REDESIGNED KITCHEN, BRAND NEW APPLIANCE PACKAGE, UPDATED BATHROOMS, RECESSED LIGHTING, NEW FIXTURES, NEW INTERIOR DOORS, TRIM AND BASEBOARDS, FRESH INTERIOR AND EXTERIOR PAINT, AND NEW TEXTURE ON ALL WALLS AND CEILINGS. The HVAC system has also been PROFESSIONALLY CLEANED AND SERVICED, along with the installation of a NEW THERMOSTAT for added comfort and efficiency. Conveniently located near major roadways, shopping, dining, schools, and everyday conveniences, this property offers outstanding accessibility while still providing the benefit of a larger lot size that is increasingly difficult to find. The expansive yard offers endless potential for outdoor entertaining, storage, gardening, or future additions. This area also allows for ADUs (Accessory Dwelling Units), and the oversized lot provides excellent potential for future expansion, guest quarters, rental income opportunities, or multi-generational living. With all the major upgrades already completed, this home is ideal for first-time buyers, downsizers, investors, or buyers seeking additional long-term upside potential. 2628 Milton Ave is the perfect blend of classic construction and modern renovation — ready for its next owner to move right in and enjoy.

Listing is courtesy of: NONA LEGACY POWERED BY LA ROSA (407-270-6841)

Listing Agent: Alex Vazquez (407-270-6841)

Remarks: One or more photo(s) has been virtually staged. Beautiful 3- bedrooms and 2- bathrooms home in the heart of Kissimmee with NO HOA! Conveniently located near Downtown Kissimmee shopping, restaurants, schools major highways,and just minutes from Kissimmee Lakefront Park. This home offers comfort,space,and the freedom of no HOA restrictions. Perdect for first-time buyers or anyone looking for a great location in Central Florida!

Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)

Listing Agent: Susana Moor (407-744-5801)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2.5-bathroom townhouse in Kissimmee, Florida! This spacious home offers a functional layout perfect for comfortable living and entertaining. The kitchen features stainless steel appliances and granite countertops, seamlessly connecting to the main living areas. The home also includes a water purification system, adding extra convenience and value. With well-sized bedrooms and a thoughtfully designed floor plan, this property showcases pride of ownership throughout. Ideally located near top attractions like Walt Disney World Resort and Universal Orlando Resort, close to major highways such as Osceola Pkwy, Turnpike, 417 & 192. As well as shopping and dining at The Loop, this home offers both lifestyle and convenience. Perfect as a primary residence, vacation home, or investment opportunity—don’t miss this fantastic opportunity!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Keegan Siegfried (813-670-7226)

Remarks: Welcome to this spacious 3-bedroom, 2.5-bath end-unit townhome in the gated community of Cypress Lakes Townhomes. Offering over 1,700 square feet of living space, this two-story residence features a flexible floor plan with a comfortable blend of ceramic tile and carpet throughout. The first floor includes a bright kitchen with a breakfast bar and pantry, an open-concept living and dining area that leads to a private covered patio, a convenient half bath, a one-car garage, and a bonus room ideal for a home office, playroom, or additional flex space. Upstairs, the primary suite offers a walk-in closet and en-suite bath, along with two additional bedrooms, a full bathroom, and upstairs laundry hookups. Residents of Cypress Lakes Townhomes enjoy community amenities including a pool, playground, and secure gated entry. Centrally located near major highways, schools, shopping, dining, and Orlando International Airport, this townhome offers comfort, convenience, and a great opportunity for homeowners or investors alike.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Peter Luu (321-917-7864)

Remarks: A must see!!! Great location!!! No HOA!!! Beautifully maintained property with 3 bedrooms 2 baths with ample room for the growing family, fenced in backyard. Located in a nice established neighborhood near schools, commerce and area recreation. Do not miss the opportunity to own a beautiful home without the rules and regulations of an association. Scheduled your viewing today.

Listing is courtesy of: LATIN CONNECTION REALTY GROUP (407-344-5510)

Listing Agent: Claudia Martinez (407-729-8027)

Remarks: Under contract-accepting backup offers. This lakefront pool home at 2602 Birchwood Avenue offers direct water views, conservation space for added privacy and sunset views from the screened pool area. On a 0.23-acre oversized lot in Kissimmee, this four-bedroom, two-bath single-family residence combines outdoor living, energy efficiency and flexible ownership with no homeowner's association and no leasing restrictions. The home features ceramic tile and laminate flooring throughout. The renovated kitchen includes solid surface and stone countertops and stainless-steel appliances. All baths have been updated and include walk-in showers. The primary bedroom is on the first floor. The attached two-car garage provides additional storage and functionality. Outdoor living centers around the screened private pool overlooking the lake, with conservation space between the home and water enhancing privacy. The fenced backyard and garden area create usable outdoor space for recreation or entertaining. This property provides convenient access to Mill Creek Elementary School, Denn John Middle School and Gateway High School.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)

Listing Agent: Ana Martins Jorge (508-858-9652)

Remarks: This house comes with a credit to the Buyer from the Seller's preferred lender to be used toward closing costs and/or an interest rate buydown. Built in 2021, this corner unit in the highly desirable SoHo at Lakeside community offers the perfect blend of modern luxury and prime Kissimmee living. Featuring a stunning contemporary elevation, this home includes 3 spacious bedrooms, 2 and a half bathrooms, high ceilings and tall windows that fill every room with natural light. The first floor showcases elegant tile throughout while the second floor offers soft comfortable carpeting in all bedrooms. The gourmet kitchen includes quartz countertops, an oversized island, stylish backsplash, wood cabinetry and stainless steel appliances. The open concept layout flows beautifully into the living areas enhanced by the natural light pouring in from the oversized windows. The master suite features a private balcony, dual closets and a spa like bathroom. Additional highlights include a 2 car garage with a paved driveway and premium corner unit privacy. The HOA covers the pool, exterior maintenance including roof, cable TV, internet and WiFi, lawn care and trash removal. This community is perfectly positioned about 12 miles from Lake Nona Medical City, 14 miles from Disney Parks and Disney Springs, 6 miles from Old Town Kissimmee and 7 miles from Bass Fishing Paradise Lake Toho, with endless dining, entertainment and shopping nearby. This exceptional home offers unmatched convenience, elevated finishes and an unbeatable location, the perfect place to call home in the heart of Kissimmee. Selling agent and buyer must independently verify all HOA restrictions. Schedule your private showing today.

Listing is courtesy of: SERHANT (646-480-7665)

Listing Agent: Lisell Melo (407-690-4973)

Remarks: Welcome to 2430 Quail Run Blvd in Kissimmee, FL, a beautifully maintained 3-bedroom, 2-bathroom home located just 30 minutes from the world-renowned Walt Disney World. Nestled in a quiet and desirable neighborhood with no HOA, this home offers the perfect balance of comfort, freedom, and convenience. Step outside to your private, fully fenced backyard featuring a lush passion fruit tree, creating a serene space to relax, entertain, or enjoy your own slice of Florida living. Inside, you will find thoughtful updates including a renovated bathroom, a newer water heater installed in 2022, and a roof replaced in 2018, providing both style and peace of mind. Whether you are looking for a primary residence, vacation home, or investment opportunity, this inviting property checks all the boxes with easy access to shopping, dining, and Central Florida attractions. Schedule your private showing today and experience the warmth and charm of this special home.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Jasmin Calle (407-801-1205)

Remarks: This single-family home in Kissimmee features 2 bedrooms and 2 bathrooms across 1100 square feet, with an additional room and bathroom providing versatile space ideal for multi-room rental or extended living. Currently operating as a successful rental, the property generates consistent income. Inside, laminate and tile flooring flow throughout the home, while the kitchen offers ample counter and cabinet space with a convenient breakfast bar—perfect for meal prep or casual dining. The covered porch provides a comfortable spot to relax, entertain, or enjoy the outdoors. Located just minutes from major roads and transportation, this home offers easy access to Downtown Orlando, Walt Disney World, Orlando International Airport, and a variety of shopping and dining options. Its combination of flexible living space and prime location makes it a standout choice for both investors and homeowners alike. Mortgage savings may be available for buyers of this listing.

Listing is courtesy of: REDFIN CORPORATION (407-708-9747)

Listing Agent: Pablo Cintron, Jr Pa (407-232-1819)

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, 1.5-bath condo perfect for a first-time homebuyer, starter home, or investment opportunity. This inviting home features an updated kitchen with granite countertops, bright white cabinetry, and mix stainless steel appliances, offering a clean and functional space that opens to the main living area. The first floor features tile flooring throughout the living and dining areas, while both bedrooms are privately located upstairs with carpet flooring for added comfort. Enjoy relaxing outdoors on the spacious screened-in porch with a private rear view. Additional highlights include a 1-car garage and a location just steps from the community pool and clubhouse, making it easy to enjoy the neighborhood amenities. Great investment potential with rental rates in the area available. Conveniently located near shopping, dining, and major roadways.

Listing is courtesy of: HELLO SUNSHINE REALTY LLC (407-719-8932)

Listing Agent: Marissa Mcclung (407-719-8932)

Remarks: This stunning home offers an exceptional blend of modern comfort and convenience. The primary suite (including updated bathroom) is conveniently located on the main floor, providing privacy and ease of access. The well-equipped GOURMET KITCHEN is perfect for cooking and entertaining, and flows seamlessly into the OPEN-CONCEPT living and dining areas. Ample natural light enhances the home's spacious feel. Outside, enjoy a FENCED-IN BACKYARD with a large wrap around SCREENED-IN PATIO, ideal for relaxation or gatherings. Recent upgrades include a NEWER ROOF (2020), HVAC (2022), and UPDATED ELECTRICAL PANEL and WATER HEATER (2023) bring lasting peace of mind. Storage is plentiful with generously sized closets throughout. Located across the street from the community pool, this home is also close to parks and major highways, ensuring easy access to recreation and commuting. Solar panels provide eco-friendly energy efficiency, making this a perfect move-in-ready home.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Mark Vescio (678-895-2631)

Remarks: Investor special! Great location! Location, Location, Location!!! This cute little house has newer roof, new plumbing, new electric lines, new appliances and new tiles throughout. This house has fence too. This house got lots of potentiality. Public records show 1 bedroom but it has 2 bedrooms and 1 bonus room that can be treated as additional bedroom (3rd Bedroom) and that brings up to total 780'. A few minutes away to Shopping, Banking, Super Markets, Hospital, Business Centers, Schools, Valencia Community College, Loop Mall, and Highways. All the information relating to this MLS Listing is intended to be accurate but cannot be guaranteed and must be verified by the buyer and buyer's agent. Motivated seller. NOT A SHORT SALE** NOT A BANK OWNED** OR NOT A FORECLOSURE** All Buyers Are Welcome! Don't miss this “Great Opportunity” to invest!! Opportunity knocks - ACT FAST!!!

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

Listing Agent: Mohammed Hossain (407-925-3442)

Remarks: Under contract-accepting backup offers. Nestled on a premier waterfront conservation lot in one of the most desirable sections of Mill Run, this beautiful 3-bedroom, 2-bathroom home offers the ultimate retreat with unparalleled privacy. New Roof 2023, New Electrical Panel 2023. Surrounded by mature trees and lush landscaping, and a private pond next door. The outdoor oasis features a screen-enclosed pool. The interior is move-in ready, with porcelain tile throughout, an L-shaped living/dining area that overlooks the pool, and the kitchen has stainless steel appliances and offers convenience with a two-car garage. Combining a serene, private setting with the convenience of being just minutes from top-rated schools and shopping, this home truly offers the best of both worlds.

Listing is courtesy of: 407 PROPERTIES (407-545-2594)

Listing Agent: Peggy Moore (407-697-1119)

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: Under contract-accepting backup offers. Whether you are looking for an investment or a more permanent place to call home, this property is sure to check all your boxes. Fully furnished and tucked away on a quiet cul de sac, this homes sits on a large plot with a conservation view in the Morgan Point community, Lakeside. The spacious home has been extremely well maintained and used by the original owners as a personal vacation home. Walking through the front door, you are met with a bright open concept formal living and dining area, giving access to the spacious master suite. A modernised kitchen (2016) with granite countertops, pendant lighting and custom cabinetry leads seamlessly into the heart of the home; the family room and the additional 2 bedrooms with pool-bath. The heated in-ground pool is complemented by a partly fenced in back yard and privacy landscaping with adjacent paved outdoor space for those perfect BBQ pool days. The roof was replaced in 2018, exterior repaint 2015, AC replaced 2016 and a complete house re-pipe - NO polybutelene including a new hot water heater in 2016. With a low HOA annual fee of $342.00 for a community with basket ball courts, tennis courts a playground and endless walking paths - this property and location is exceptional. Don't miss this incredible opportunity and schedule your showing today.

Listing is courtesy of: SOUTH ORANGE PROPERTY & REAL ESTATE SERVICES INC (407-851-7002)

Listing Agent: Deborah Mansell (407-668-7918)