Kissimmee Homes with Custom Architectural style

Kissimmee Homes with Custom Architectural style

Welcome to Kissimmee, Florida—a vibrant city located in the heart of Osceola County, renowned for its rich cultural tapestry and close proximity to world-famous attractions. Nestled just minutes away from the magical realm of Walt Disney World, Kissimmee offers a delightful blend of excitement and tranquility, making it an ideal place for families, retirees, and everyone in between.

One of the standout features of Kissimmee is its unique architectural landscape. The city boasts an impressive array of homes with custom architectural styles, each telling its own story through design and craftsmanship. From charming Mediterranean villas with terracotta roofs to modern coastal retreats that embrace the sunshine, these residences are not just houses; they are works of art that reflect the individuality of their owners.

Imagine waking up in a home that features intricate details, such as arched doorways, ornate moldings, and expansive outdoor living spaces that invite you to enjoy the year-round Florida sunshine. Whether you prefer a home with a rustic farmhouse aesthetic or a sleek contemporary design, Kissimmee has something to suit every taste.

The community is also enriched by its lush parks, scenic lakes, and vibrant local markets, providing residents with ample opportunities for leisure and recreation. With a strong sense of community and an array of amenities, Kissimmee is more than just a place to live; it’s a lifestyle.

Explore the enchanting neighborhoods of Kissimmee and discover your dream home today, where custom architecture meets the warmth of Florida living!

Newest Kissimmee Homes with Custom Architectural style

$838,900
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
$7,995,000
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
$515,999
3 Beds ⋅ 3 Baths ⋅ Bvl Unit 2 SubDv. ⋅ 34743 Zip Code
Pre-Construction. To be built. New Construction! Custom Home, Luxury Home, it was finished in 95% and is awaiting 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
$599,900
4 Beds ⋅ 4 Baths ⋅ Kissimmee Bay SubDv. ⋅ 34744 Zip Code
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 so schedule a showing today!

2747 Kissimmee Bay Circle, 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
$1,385,000
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
$2,999,000
11 Beds ⋅ 13 Baths ⋅ Reunion West Vlgs North SubDv. ⋅ 34747 Zip Code
*ALERT* PRICE CUT * PRICED TO SELL* Situated on a PRIME LOT in the highly desirable and award-winning REUNION RESORT, this CUSTOM-BUILT estate home boasts panoramic views of lush NATURAL WOODLAND with POND backdrop providing both scenic beauty as well as PRIVACY. No rear neighbors! Professionally designed & decorated over 3 floors and with high end features abound, this FULLY FURNISHED & TURNKEY home is perfect for entertaining family & guests on a large scale with VERSATILITY OF USAGE from a primary residence, second/vacation home and/or investment property! This home comes with an IMPRESSIVE BOOKINGS CALENDAR if kept in the existing short term rental program. As soon as you step inside the entryway, the double heighted soaring ceiling of the foyer immediately sets a scene of GRANDEUR and allows for plenty of natural light. At the heart of the home is a vast OPEN-PLAN CONCEPT living area comprised of the gourmet kitchen (which is a chef’s dream with expansive center island, high-end stainless-steel appliances and breakfast bar seating for 6), enhanced by a dining table area (which comfortably seats 18) and spacious but comfortable lounge sitting area. Comprised of 9 well-appointed primary bedroom suites and 2 distinguished bespoke themed bedrooms (Harry Potter and Princess inspired), all with ensuite bathrooms, this SPECTACULAR RESIDENCE can comfortably accommodate up to 24 guests. Awaiting your enjoyment, there are multiple casual living areas as well as lavish entertaining lounge spaces to relax, socialize, watch a movie or for those who prefer, a night of gaming! For your added convenience, there is also a RESIDENTIAL ELEVATOR. Ample AMENITIES include a dedicated arcade room, a home theater (seating 13), a secret hidden hide-away gaming room (flanked each side by the themed bedrooms) and loft office style area. Designed to take full advantage of Florida lifestyle living, the RESORT-STYLE outdoor area is a PRIVATE OASIS with both covered lanai and open sun patio space - highlights include a spectacular heated INFINITY EDGE POOL with spillover SPA, WATERFALL with GROTTO, a pool SLIDE as well as swim up in-pool bar stools, well-equipped summer kitchen, FIREPIT, plentiful lounge & enjoyment spaces and outdoor bathroom. Seamlessly blending the indoor with the outdoor and further complementing the home, there is access to multiple private balconies overlooking both the pool area and the stunning sweeping views. Flexibility has been preserved in the GARAGE, a rare occurrence in the community, which also serves as a basketball half-court. Other features of the home include a SONOS sound system, 2 dedicated independent laundry areas and plenty of closet & storage space throughout. 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, Har-True tennis courts, pickleball, bocce ball, volleyball, crazy golf, a playground, full-service salon and spa. Reunion is conveniently located a couple of miles away from Walt Disney World Resort, Seaworld and Universal Studios. Video as well as 3D virtual tour & floorplan available! DON’T MISS OUT, schedule your showing today! **ADDITIONAL OPPORTUNITY: Adjacent homesite at 594 Muirfield Loop is also available for purchase MLS #O6335453**

600 Muirfield Loop, Reunion
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