Kissimmee Homes with Custom Architectural style

Kissimmee Homes with Custom Architectural style

Welcome to Kissimmee, Florida – a vibrant city nestled in the heart of Osceola County, where sunshine meets charm and adventure awaits at every corner. Known for its proximity to world-renowned attractions like Walt Disney World and Universal Studios, Kissimmee offers a unique blend of excitement and tranquility, making it the perfect place to call home.

Kissimmee boasts a rich history and a diverse community, where friendly neighbors greet you with warm smiles and a spirit of camaraderie. The city is adorned with lush parks, scenic lakes, and beautiful landscapes, providing residents with a picturesque backdrop for outdoor activities and family gatherings. From thrilling airboat rides through the Everglades to peaceful strolls along Lake Tohopekaliga, there’s something for everyone to enjoy.

One of the most captivating aspects of Kissimmee is its stunning homes, particularly those showcasing custom architectural styles. These residences reflect the creativity and individuality of their owners, featuring unique designs that stand out in the neighborhood. Whether you’re drawn to Mediterranean-inspired villas, modern masterpieces, or charming craftsman bungalows, Kissimmee's real estate market offers a diverse array of options tailored to suit your lifestyle.

Living in Kissimmee means embracing a vibrant community filled with cultural events, delicious dining options, and endless recreational opportunities. With its warm climate and welcoming atmosphere, this city is not just a place to live; it’s a place to thrive. Discover your dream home in Kissimmee, where custom architecture meets the magic of Florida living. Your new adventure awaits!

Newest Kissimmee Homes with Custom Architectural style

$797,500
4 Beds ⋅ 3 Baths ⋅ City Centre Kissimmee Residential Condo Cb 12 Pg 1 SubDv. ⋅ 34741 Zip Code
Experience one-of-a-kind penthouse living in the heart of Downtown Kissimmee. This architect-designed top-floor residence offers 4 bedrooms, 3 full baths, 3,577 square feet under air, soaring 10-foot ceilings, two expansive living areas, and more than 1,200 square feet of private wraparound balcony. Panoramic Lake Tohopekaliga and downtown views fill nearly every room. The custom kitchen features an oversized island, premium appliances, French-door refrigerator, and built-in wine cooler. The primary suite includes lake views, custom walk-in closets, a soaking tub, and dual vanities. Smart-home improvements, custom epoxy floors, secure elevator access, and two covered assigned parking spaces complete this exceptional residence.

111 E Monument Avenue Unit 801, Kissimmee
$340,000
4 Beds ⋅ 3 Baths ⋅ Roseland Court SubDv. ⋅ 34741 Zip Code
Great Opportunity!!! ?? This spacious 4-bedroom, 3-full-bathroom home at 1515 Mabbette St, Kissimmee, FL 34741 offers an excellent combination of space, flexibility, and location! ? Fairly new roof — approximately 4 years old ? No HOA ? Potential for short-term rental use — buyer to verify local regulations and requirements ? 4 bedrooms and 3 full bathrooms ? One bedroom with its own bathroom and private entrance, offering excellent flexibility as a studio, guest suite, or in-law suite ?? Excellent location in downtown Kissimmee, just minutes from restaurants, schools, parks, major highways, and everyday conveniences. Whether you're looking for a primary residence, an investment property, or a home with additional living flexibility, this property is worth a look! Schedule your private showing today! ????

1515 Mabbette St, Kissimmee
$564,900
4 Beds ⋅ 4 Baths ⋅ Bellalago Ph B-2 SubDv. ⋅ 34746 Zip Code
NEWER ONE OWNER HOME, WELL LOCATED IN THE FANTASIC SUBDIVISION OF BELLALOGO, TO MANY FEATURES TO LIST, LAKE FRONT COMMUNITY, PARKS, PLAYGROUNDS, DOG PARK, COMMUNITY POOL, ETC. HOME FEATURES AN OPEN LAYOUT FOR FAMILY AND GREAT GET TOGETHERS, BIG REAR YARD TO ALLOW EXTENDED LIVING OUTSIDE WITH FRIENDS FAMILY AND NEIGHBORS. 4 LARGE BEDROOM AND 3.5 BATHS, GAME ROOM, ETC . CHIEF STYLE KITCHEN WITH ALL THE FEATURES YOU WOULD EXPECT. WELL APPOINTED FEATURES THROUHTOUT THE HOME. ALSO INCLUDES THE EXTRA LARGE AND VERY MUCH DESIRED 3 CAR GARAGE, PROVIDING BOTH CONVENYENCE AND MULITPLE STORAGE OPTIONS. THIS HOME HAS IT ALL AND IS PRICED TO MOVE.

2931 Agostino Terrace, Kissimmee
$833,000
3 Beds ⋅ 2 Baths ⋅ Pleasant Hill Trails Unit 3 SubDv. ⋅ 34746 Zip Code
Seller says bring me your offer!!! No HOA, Mostly Cleared 5.32 acres fenced in with lots of frontage space. This property would be good for country living New Roof replaced June 2024. The land is agricultural pastor and high and dry. Did I mention that it is also zoned for horses and has an additional barn/workshop? New construction nearby. Being only 1 mile from Valencia College it might make a good spot for student housing.

3180 Canter Lane, Kissimmee
$1,125,000
5 Beds ⋅ 5 Baths ⋅ Reunion Ph 1 Prcl 1 Unit 3 SubDv. ⋅ 34747 Zip Code
Located within the award winning REUNION RESORT and boasting sweeping views of the 6th, 7th and 8th holes of the signature Tom Watson / Independence golf course, this stunning residence is a FULLY FURNISHED, 5 bedroom GOLF FRONT property with private pool. **ACTIVE TRANSFERABLE MEMBERSHIP available** Perfect as a main residence, second/vacation home or investment property, this residence is completely TURNKEY and ready to enjoy. The open plan layout is well designed throughout lending itself to a spacious feel whilst providing plenty of relaxing as well as entertainment areas for family, friends and guests. From the living room with contemporary fireplace, fully equipped kitchen (together with both casual countertop seating for 8 as well as separate kitchen eating area for 8), a formal dining room which also seats 10, expansive MOVIE/GAME ROOM with reclining seating for 8 (with foosball, basketball, air-hockey table and playstation area), wet bar, study/desk area to a conversational coffee seating area. There is a large size guest bedroom on the ground floor and upstairs a further 4 bedrooms, 3 being ensuite and one Jack & Jill. The primary bedroom is on the 2nd level and has direct access to the expansive balcony and the ensuite has a spa like infinity edge soaking tub with jacuzzi jets. Also on the 2nd floor is an additional lounge seating area with double doors opening onto the balcony spanning the width of the home which OVERLOOKS THE POOL with spillover jacuzzi and picturesque GOLF COURSE VIEWS. With its enviable aspect, enjoy the sunshine either lounging out on the sizeable deck or seek shelter under the covered lanai. Home has outdoor pool half bathroom and as welll as patio shower. In the evenings basque in the beautiful Florida sunsets cooking on the built-in grill and dining in the outdoor area. Situated near a quiet CUL DE SAC, this residence is ideally located near the plentiful amenities of the Reunion Resort. **BOOKINGS TRANSFER if stay with existing rental manager.** Roof Oct 2022, HVAC's 2021 and 2022, two gas tankless water heaters 2022. Property has stunning ACCENT FEATURES, modern lighting, fans, newer appliances and smart TVs in every room plus combo home theater/games room. With its three world class golf courses (designed by Arnold Palmer, Tom Watson and Jack Nicklaus), a golf academy, Clubhouse at The Bear’s Den, six onsite restaurants, twelve community swimming pools, a multimillion-dollar water park, six Har-True tennis courts, pickleball, bocce ball, volleyball, crazy golf, a playground, and full-service salon and spa, Reunion is only a couple of miles away from Walt Disney World Resort, SeaWorld and Universal Studios. Don't miss out on this gem, schedule your viewing today!

7388 Gathering Court, Reunion
$7,994,900
10 Beds ⋅ 14 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code
Welcome to the Golden Bear Mansion, an extraordinary 10-bedroom custom estate situated on an oversized double lot in the renowned golf community of Reunion Resort this one-of-a-kind residence offers an unmatched collection of luxury amenities rarely found in a private home. The striking front façade immediately sets the tone, highlighted by dramatic dual travertine staircases that lead to a fully covered balcony with retractable screens—perfect for enjoying the Florida lifestyle year-round. Inside, regal entry doors with Oni signature hands-free automatic operation welcome you into the grand atrium and the first of several spectacular entertaining spaces. This area features a full chef’s kitchen with high-end commercial appliances, custom quartz countertops, marble-inlaid flooring, and a card lounge with multiple televisions. Beyond the main entertaining area, a custom vestibule leads to several remarkable spaces including a private 12-seat movie theater, the main entertainment living room, a two-lane bowling alley, and access to the fully finished lower level. The finished basement offers an incredible collection of wellness and recreation amenities, including a private massage room, a full indoor basketball court with a retractable hoop that converts the space into a squash court, locker facilities with his-and-hers showers, a sauna, and a steam room. The wellness experience continues with an indoor spa featuring a hot tub and heated lounge chairs, as well as a fully equipped private fitness center. On the second level, the formal living room flows seamlessly into a stunning custom kitchen anchored by a massive single-slab quartz island. A grand hallway showcases tray ceilings, marble inlaid floors, dramatic chandeliers, and elegant architectural details throughout. This floor also hosts beautifully designed guest suites, each uniquely styled with tray ceilings, private en-suite bathrooms, custom showers, and thoughtful luxury touches such as heated towel racks. The third level functions perfectly as a private multi-generational suite, complete with its own kitchen, living room, and two expansive primary suites. Each suite features spa-inspired bathrooms, including one with a steam shower and another with a Jacuzzi tub with a hidden television. Outside, the resort-style pool area overlooks the renowned Jack Nicklaus Signature Golf Course at Reunion Resort and is designed for ultimate relaxation and entertainment. Enjoy an oversized pool with a waterslide and built-in spa, travertine decking, a custom swim-up bar, and a pavilion with retractable screens and a fire pit—perfect for entertaining in style. This exceptional estate offers far more than words can capture. Experience the Golden Bear Mansion in person and discover one of the most remarkable luxury homes in Central Florida.

905 Golden Bear Drive, Reunion
$501,999
3 Beds ⋅ 3 Baths ⋅ Bvl Unit 2 SubDv. ⋅ 34743 Zip Code
Pre-Construction. To be built. New Construction! Custom Home, Luxury Home, ready to move with permission to use it. To be Build. Brand New Home custom home to be built. Built By MGA Construction US, Custom Homes. Construction within more strict codes of construction of FL and US. Open concept layout or open floor plan. The windows with new codes to support wings of hurricane and range of durable, energy - efficient and customizable, codes FBC to beams trusses and hurricane ties, hurricane straps resistant at hurricane, and structures to support hurricanes in FL, walls in blocks with tied together with cement beams. Brand New Home, abundant natural light, modern kitchen with quality cabinets solid wood and finishes 42" with Quartz countertop, with backsplash tile in walls kitchen, all floor in Porcelain Tile. Spacious master bedroom and spacious master bathroom with shower tub and big walk-in closet, big family room together with formal dining room separate. Goods schools and close to bus stop and shopping centers. First time buyers can qualification with Purchase Assistance/ Down payment assistance Osceola County. Seller can help pay for a buyer`s closing costs through seller's concessions, which are credits capped between .005% at 1% of home purchase price.

292 Gardenia Road, Kissimmee
$625,000
4 Beds ⋅ 4 Baths ⋅ Kissimmee Bay SubDv. ⋅ 34744 Zip Code
FEATURING SEPARATE ONE-BEDROOM SUITE WITH KITCHEN, BATH AND PRIVATE ENTRANCE! Welcome to this exceptionally well-designed home in the exclusive gated golf community of Kissimmee Bay Country Club, which offers luxury living with stunning fairway views. This impressive 4-bedroom 3.5-bathroom residence sits on an oversized lot with a desirable brick paver circular driveway and distinctive concrete barrel tile roof. TWO BEDROOMS ARE ON THE FIRST FLOOR AND TWO BEDROOMS UPSTAIRS!! Step into the dramatic two-story foyer that opens into the formal living room with soaring 20-ft ceilings & abundant natural light. An elegant wood staircase leads to the second floor, while the formal dining room provides perfect space for hosting special occasions. The back of the home on the first floor features a completely self-contained in-law one-bedroom suite with its own private entrance that is perfect for extended family, guests or rental income. This retreat includes a full kitchen, sitting area, bedroom, full bath and patio access overlooking the golf course. A standout feature of this home is NO CARPETING. Tile and premium wide-plank engineered hard surface flooring flows seamlessly throughout, perfect for Florida's climate and allergy-conscious buyers. The home boasts impressive architectural details such as layered crown molding, arched doorways and tray ceilings. The expansive kitchen showcases cream-toned custom cabinetry with glass-front display cabinets, a shimmering glass tile backsplash with dark speckled granite countertops plus a dinette. Modern stainless-steel appliances include a built-in double wall oven, dishwasher & refrigerator providing a sleek, professional look. The primary suite is conveniently located on the first floor with a luxurious ensuite bathroom with dual vanities, a relaxing, jetted garden tub & an oversized shower. Adjacent to the kitchen is the laundry room which includes built-in cabinets, a utility sink, a closet PLUS a half-bath. Upstairs, there are two guest bedrooms that share a full bath, with one featuring a private balcony providing plenty of privacy. The heart of this home is the inviting family room, complete with a wet bar featuring rich cherry cabinetry with a stunning emerald countertop, plus a cozy wood-burning fireplace with dramatic marble surround and built-in shelving, which makes this the ideal space for creating lasting memories. Recent upgrades: new hot water heater (2024), plumbing (2023), multiple HVAC systems for zoning control (primary 2025, in-law area 2019, 2nd floor 2020). Residents of this community enjoy resort-style living with access to the 18-hole par 72 golf course designed by Lloyd Clifton, golf club with bar and restaurant, tennis, pickleball and basketball courts, RV and boat parking available, boat ramp with Lake Toho access for skiing, boating and fishing, plus a community pool. HOA also includes cable and high-speed internet. This prime location offers golf course living with practical accessibility: minutes from Orlando Int'l Airport, Disney World, medical facilities, schools, shopping & dining. Easy access to Florida Turnpike, Hwy 417 & Hwy 528 makes this ideal for year-round residents or vacation rental. This is the Florida lifestyle that you've been dreaming of; you've got to see it!

2747 Kissimmee Bay Circle, Kissimmee
$534,900
4 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34746 Zip Code
Positioned along the 13th hole of The Oaks National Golf Course in Kissimmee, this golf-front residence offers elegant interiors, updated systems and a layout designed for comfort and entertaining. The four-bedroom, two-and-one-half-bath home features a flexible floor plan with high ceilings and abundant natural light throughout. The first-floor primary suite overlooks the course and private pool, with a spacious bath offering dual vanities, soaking tub, separate shower and walk-in closets. The kitchen includes granite countertops, wood cabinetry, decorative backsplash, accent lighting, reverse osmosis system and newly installed appliances. A wine storage feature adds to the home’s entertaining appeal. Upstairs, three generously sized bedrooms are joined by a double loft-style flex space, ideal for use as a media lounge, home office or playroom. Outdoor living is enhanced by a custom pool and spa with slate waterfall, surrounded by slate decking, mature landscaping and a double-height screened enclosure. A professionally designed irrigation system supports the landscaped grounds. Smart-home features include Alexa-enabled lighting and a Ring doorbell. Recent upgrades include a new roof and HVAC system in 2020, along with a fully paid-off solar system offering long-term energy savings. Community amenities include tennis courts, parks and playgrounds, with convenient access to local shopping, dining and attractions.

1524 The Oaks Boulevard, Kissimmee
$499,900
5 Beds ⋅ 3 Baths ⋅ Shingle Creek Reserve At The Oaks Ph 3 & 4 SubDv. ⋅ 34746 Zip Code
Virtually Staged. For the first time in eight years, one of the rarest lots in The Oaks is now available. Special Holiday Promotion Free 85 inch samsung Tv if purchased by January 1st! Welcome to 2924 Boating Boulevard, Kissimmee, Florida 34746, a breathtaking 5-bedroom, 3-bath residence where elegance, craftsmanship, and nature come together. From its custom MasterCraft masonry in the front to its extended enclosed lanai in the back, this home was built to impress. Nestled along oak-lined streets in one of Kissimmee’s most desirable golf course communities, it sits on one of the rarest lots in the neighborhood backing up to a protected conservation area and positioned directly across from the boat lift that takes you straight onto Lake Toho, one of America’s best bass fishing lakes. With a peaceful pond, scenic trails, and lake access all just 40 feet from your back door, this property offers a lifestyle few others can match. Step inside and experience the seamless flow of the open-concept design. At the heart of the home is a chef-inspired kitchen featuring rich cherry wood cabinets, black sparkling granite countertops, a center island, and a bar that opens to the living area, ideal for entertaining or family gatherings. Just off the main living space, the downstairs suite offers a comfortable bedroom with a nearby full bath, perfect for guests, in-laws, or anyone who prefers first-floor living. Upstairs, the oversized master suite spans nearly half the top floor, creating a luxurious retreat where the owner truly gets the best. The master bathroom features dual Jack and Jill sinks, a royal soaking bathtub, a separate shower stall, and a closeted toilet for extra privacy during your most personal moments. Down the hall, three additional bedrooms each feature walk-in closets, while a large loft adds flexibility for a home theater, gym, or office. This home has been lovingly maintained and upgraded with a brand-new roof (2025), AC serviced (2024), updated flooring (2018), new gutters (2018), and a French drain for added drainage and foundation protection, along with many other repairs and improvements as needed for lasting comfort and peace of mind. Out back, the extended enclosed lanai spans the full width of the home, offering a tranquil escape surrounded by nature. Without taking more than a step out your back door, you can watch deer grazing, wild turkey exploring, otters playing near the shoreline, and eagles soaring above. With no fence behind you and direct access to the lift, pond, and walking trails, this home perfectly blends luxury, serenity, and adventure. The Oaks community features a golf course, tennis and pickleball courts, basketball, playgrounds, and a clubhouse with a new restaurant. Located just 40 minutes from Orlando International Airport and 30 minutes from Disney, this home delivers the perfect balance of luxury, lifestyle, and location. Wanna see the rest? Schedule your private showing today. Virtual tour available upon request.

2924 Boating Boulevard, Kissimmee
$1,365,000
6 Beds ⋅ 6 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code
Experience luxury and performance in this stunning Reunion Resort home located on one of the community’s deepest lots with panoramic views of the Jack Nicklaus Golf Course. This property stands out as a high-producing short-term rental with strong financial performance and an active Reunion Resort membership, professionally managed by Magical Vacation Homes. The modern open floor plan features a spacious kitchen with granite countertops, stainless steel appliances, and a large breakfast bar that flows into the dining and living areas, ideal for entertaining or relaxing after a day at the parks. Step outside to your private retreat complete with a heated pool and spa, tiki bar with built-in BBQ grill, wine cooler, and mini-fridge, surrounded by lush landscaping and a personal putting green. Inside, the entertainment continues with a full arcade-style game room featuring basketball, racing, and air hockey, plus an upstairs loft with shuffleboard, poker table, Golden Tee, and Smart TV. Every bedroom is tastefully furnished with modern décor and ensuite baths, making this home perfect for guests and family alike. Reunion Resort is a world-class gated community offering 3 championship golf courses designed by Nicklaus, Palmer, and Watson, a multi-acre water park with lazy river, tennis and pickleball courts, fitness center, restaurants, spa, and 24-hour security. Located minutes from Walt Disney World® and major attractions, this property delivers the perfect balance of luxury, location, and income potential.

801 Golden Bear Drive, Kissimmee
$4,999,995
11 Beds ⋅ 14 Baths ⋅ Reunion West Village 03a SubDv. ⋅ 34747 Zip Code
Ideally located in the award-winning REUNION RESORT and overlooking the 6th hole of the Jack Nicklaus designed Tradition golf course, presenting this spectacular FULLY FURNISHED custom ESTATE HOME boasting a lifestyle of pure LUXURY! Upon arrival, an impressive double-heighted ceiling entryway opens to the foyer and huge living/great room areas with large sliding doors framing PICTURE PERFECT VIEWS. Designed to accommodate large gatherings, experience the true Florida lifestyle, seamlessly blending the indoor & outdoor lounge and dining areas featuring automatic retractable screens as well as multiple entertainment spaces. Perfect for both family & guest entertaining and/or to use as a REVENUE/INCOME GENERATING INVESTMENT property (with the added available opportunity to transfer future bookings!). At the heart of the residence is a magnificent CUSTOM high gloss gourmet kitchen with quartz countertops, stainless steel appliances, oversize central island and hidden spacious walk-in pantry. Design features are a bound and include contemporary flooring, MODERN BESPOKE CABINETRY, tray ceilings and DESIGNER fittings. Enjoy the vast array of AMENITIES this residence has to offer including an ARCADE room jam packed with a wide variety of electronic games, a CASINO themed room decked out with cutting edge digital slot machines, a unique open-concept living entertainment space with secondary kitchen/bar area and countertop seating, lounge area as well as a luxury HOME THEATER (with seating for 12). Additional features include a fully equipped fitness GYM and a private SPA with sauna & steam shower. For your added convenience, there is also a residential elevator! Each of the 11 luxurious bedrooms have ensuite bathrooms and are well appointed in size with two PROFESSIONALLY THEMED MASTERPIECES sure to impress – the Jurassic Park room sleeps 5 and showcases a life-size dinosaur head and jeep vehicle-bed whilst the Steamboat Willie Mickey Mouse room has bunkbeds which sleep 8. The PANORAMIC FAIRWAY VIEWS can be especially appreciated from the upper balcony area as well as from under the covered lanai and open patio areas with heated sparkling POOL featuring a beach entry point, spa and fountain. Make the most of the outdoor full BBQ kitchen with plentiful dining space, casual countertop seating together with an inviting lounge area with two-sided fireplace watching early morning sunrises and late evening sunsets! An ACTIVE TRANSFERRABLE MEMBERSHIP grants access to the many amenities of the Reunion Resort with its three world class golf courses (designed by Arnold Palmer, Tom Watson and Jack Nicklaus), a golf academy, Clubhouse at The Bear’s Den, six onsite restaurants, twelve community swimming pools, a multimillion-dollar water park, six Har-True tennis courts, pickleball, bocce ball, volleyball, crazy golf, a playground, and full-service salon & spa. Reunion is only a couple of miles away from Walt Disney World Resort, Seaworld and Universal Studios. VIRTUAL TOUR, VIDEO and FLOORPLAN are available. Book your private showing today and make this dream home your reality!

1125 Grand Traverse Parkway, Reunion
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