Kissimmee Homes with Custom Architectural style

Kissimmee Homes with Custom Architectural style

Located in Osceola County, Florida, Kissimmee is a vibrant city known for its rich history and diverse culture. Home to a growing population, Kissimmee offers a unique blend of modern amenities and small-town charm. The city boasts a variety of recreational activities, including parks, golf courses, and water sports, making it an ideal place for outdoor enthusiasts.

For those seeking a home with custom architectural style, Kissimmee has a range of options to choose from. True to its reputation for innovation and creativity, Kissimmee features homes with unique designs that cater to individual tastes and preferences. Whether you're looking for a modern masterpiece or a historic gem, Kissimmee's real estate market has something for everyone.

With its convenient location, excellent schools, and thriving economy, Kissimmee is a desirable place to live for families, young professionals, and retirees alike. Discover the beauty and charm of Kissimmee and find your dream home in this dynamic city in the heart of Florida.

Newest Kissimmee Homes with Custom Architectural style

7608 Cabana Court Unit 303, Reunion
$284,900
3 Beds ⋅ 3 Baths ⋅ Villas At Reunion Square Ph 2 Condo SubDv. ⋅ 34747 Zip Code
***Platinum Membership Available***Location Location. Best priced condo in Reunion. Enjoy the peace and tranquility of your very own private home on the third floor located on 14th hole of the Watson course. This spacious 3-bedroom, 3 bath condo is located in Villas South of Reunion Resort and can be used as your very own primary residence or vacation home. Your new condo is just steps away from a spectacular Cabana Court pool. A/C is 2017. Water Heater is 2016. Newer Washer and Dryer. Reunion Resort offers 3 signature golf courses, tennis center, state of the art water park with lazy river, 12 community pools, 5 restaurant areas, playgrounds, organized activities and so much more. The resorts proximity to all of the major theme parks, especially Disney World, being just 6 miles away, makes this vacation community a top choice for visitors of all ages.Please note any property without a Resort membership may not be able to use any of the resort amenities.

7608 Cabana Court Unit 303, Reunion
821 Golden Bear Drive, Reunion
$3,300,000
7 Beds ⋅ 9 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code
Introducing 821 Golden Bear Drive — where custom architecture, golf-front serenity, and resort luxury converge in a way that simply cannot be replicated. Set within the gates of Reunion Resort, this striking three-story new construction estate commands attention from the moment you arrive. Inside, a breathtaking floating staircase anchors the home and signals the level of craftsmanship carried throughout every detail. Seven en-suite bedrooms, 7 full baths, and 2 half baths mean comfort and privacy for every guest — no compromises, no sharing. Two king primary suites lead the way, joined by two additional king suites and imaginative custom-themed bunk rooms that turn bedtime into an adventure. Dual laundry rooms (floors 1 and 2), a private home theatre with a large screen and plush sofa seating, and a third-floor game room with foosball, shuffleboard, basketball, racing simulators, and arcade classics check every box on your wish list and then some. The outdoor living is nothing short of extraordinary. An infinity-edge pool and spillover spa cascade into a step-down fire pit, framed by sweeping golf course views that make every evening feel like a vacation. A built-in BBQ and generous lounge space make entertaining effortless, while multiple front and rear balconies on every level bring the outdoors in and the views to you. Beyond your door, Reunion Resort membership unlocks three signature golf courses by Jack Nicklaus, Arnold Palmer, and Tom Watson, a five-acre water park with lazy river, tennis, pickleball, on-site dining, and a fitness center — all just 6 miles from Walt Disney World. Every inch of this home was thoughtfully designed and masterfully executed. If you've been waiting for something truly one of a kind — the wait is over.

821 Golden Bear Drive, Reunion
1999 Limestone Trail, Kissimmee
$575,000
3 Beds ⋅ 2 Baths ⋅ Four Seasons At Orlando Ph 3c & 3d SubDv. ⋅ 34747 Zip Code
Welcome to the Four Seasons of Orlando in Kissimmee a 24 hour guard gated community. This is a ST. THOMAS model home featuring a welcoming foyer with coffered ceilings, dry bar and luxury vinyl flooring throughout the home. The two bathrooms have tile flooring. Enjoy the open concept kitchen, dining room and great room with upgraded cabinets and quarts counters. The owner's suite features luxury vinyl flooring, coffered ceilings and a beautiful primary bath with ceramic tile flooring. There are two additional bedrooms and a guest full bath. Four panel sliders brings you out to the private extended screened in lanai. The lanai is 40 feet wide and faces conservation. The garage houses two cars plus a golf cart space. You will love living at the Four Seasons of Orlando in Kissimmee. We are entwined within the Mystic Dunes Golf Course which offers wonderful views. Our Calypso Clubhouse offers a coffee bar, kitchen, meeting rooms, grand ballroom, ping pong and pool room, card room, excercise room and a state of the art exercise room. Outside enjoy the two pools, hot tub, grilling in the pool courtyard, tennis, pickleball courts and so much more. Our clubhouse has so many activities for you to enjoy from line dancing to yoga classes. You can also walk or use your golf cart to go over to Mystic Dunes Clubhouse and have brunch, lunch or dinner. They give our residents a discount.

1999 Limestone Trail, Kissimmee
1196 Castle Pines Court, Kissimmee
$4,300,000
7 Beds ⋅ 9 Baths ⋅ Reunion West Village 3a SubDv. ⋅ 34747 Zip Code
Welcome to 1196 Castle Pines Court, an exceptional fully furnished 7-bedroom, 7-full-bath, 2-half-bath golf-front residence located within the exclusive gated Reunion Resort. Completely remodeled in 2025, this impressive home offers approximately 6,900 square feet of air-conditioned living space and 8,971 total square feet, combining sophisticated contemporary design with incredible spaces for entertaining. The newly redesigned kitchen showcases custom cabinetry, a walk-in pantry and a brand-new DACOR appliance package, opening seamlessly to the home’s expansive living areas. The main living room makes a dramatic statement with a large-format porcelain feature wall, custom millwork and electric fireplace. Throughout the home, the 2025 renovation continues with beautifully remodeled bathrooms featuring large-format porcelain tile, custom floating vanities with integrated sinks and sensor lighting, along with custom closets and elevated architectural finishes. A striking custom entryway features detailed millwork, large-format slabs and smoked-gray glass railing. Designed for entertaining on every level, the home features a dedicated Control4 theater with custom millwork and padded wall treatments, under-counter refrigerator and snack bar. A separate bonus room is ready for an arcade or gaming space, while the second-floor loft offers an additional sitting and TV area with billiard table. Outdoors, enjoy a private resort-style pool, expansive entertaining areas and a summer kitchen, all overlooking the 5th hole of Reunion’s Jack Nicklaus Signature Golf Course. The home is also equipped with a Culligan HANS whole-home reverse-osmosis system and is being offered fully furnished. Located within the gated Reunion Resort, residents and guests can enjoy an extensive collection of resort amenities, including championship golf, multiple dining options, tennis, miniature golf, water-park attractions and a lazy river. The home currently has an active Reunion membership. With its extensive 2025 renovation, designer finishes, entertainment spaces, golf-course setting and turnkey furnishings, 1196 Castle Pines Court offers a distinctive opportunity to experience the Reunion Resort lifestyle.

1196 Castle Pines Court, Kissimmee
111 E Monument Avenue Unit 801, Kissimmee
$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
1515 Mabbette St, 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
2931 Agostino Terrace, 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
3180 Canter Lane, 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
7388 Gathering Court, Reunion
$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
8398 Happy Trail, Kissimmee
$2,495,000
4 Beds ⋅ 4 Baths ⋅ Happy Trails Units 1 & 2 Unrec SubDv. ⋅ 34747 Zip Code
Custom-Built 2024 Private 5-Acre Estate. High & Dry in Gated Happy Trails. Welcome to a rare opportunity to own this exceptional estate situated on 5 pristine high-and-dry acres, one of the highest elevations within the community. Positioned on a desirable corner lot with dual gated entrances, the property offers enhanced accessibility, privacy, and flexibility for a variety of uses. Ideally located just minutes from Celebration, Reunion, and Walt Disney World, this exceptional property offers the perfect balance of luxury, privacy, and convenience with no HOA. A long, elegant private driveway leads to this impressive residence featuring 4 bedrooms, 3.5 bathrooms, an oversized 3-car garage with EV charging outlet, and a thoughtfully designed open-concept modern floor plan with expansive living spaces throughout. Step inside to experience soaring 14-foot ceilings throughout the entire home, enhanced by tray ceilings in the dining room, living room, and primary suite, along with a striking 16-foot cathedral ceiling in the designer kitchen, creating a bright and dramatic architectural presence. The gourmet kitchen is a true centerpiece, showcasing an oversized island with Italian granite, extensive custom cabinetry, a hidden oversized walk-in pantry, and a seamless connection to the main living and dining areas, ideal for both everyday living and entertaining. The elegant dining room features a stunning double glass-door wine display, while a beautifully designed wet bar with wine cooler adds both style and functionality. The spacious living area is anchored by a modern built-in electric fireplace with custom finishes. The breakfast area is framed by oversized picture windows, offering beautiful views of mature oak trees and the natural landscape, creating a serene, park-like setting. The luxurious primary suite offers a spa-inspired bathroom featuring a freestanding soaking tub positioned beneath a large picture window, a walk-in glass shower, and refined finishes that create a true retreat experience. All additional bedrooms are generously sized and designed for comfort and privacy. Outdoor living is equally impressive, featuring a covered lanai with a fully equipped outdoor kitchen, extensive paved areas, and expansive open acreage surrounded by beautiful mature trees. Zoned for horses, the property offers ample room for a barn, workshop, RV storage, or future additions. Additional features include double-glazed energy-efficient windows, premium modern motorized blinds throughout the entire home, large sliding glass doors, a private water well eliminating monthly water costs, and a seven-zone irrigation system.

8398 Happy Trail, Kissimmee
905 Golden Bear Drive, 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
292 Gardenia Road, Kissimmee
$474,999
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
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