Kissimmee Homes with Cottage Architectural style

Kissimmee Homes with Cottage Architectural style

Welcome to Kissimmee, Florida – a vibrant city nestled in the heart of Osceola County, just a stone's throw away from the enchanting attractions of Orlando. Known for its picturesque landscapes and warm, welcoming atmosphere, Kissimmee offers a unique blend of suburban charm and urban convenience. With its rich history, diverse culture, and a plethora of recreational activities, Kissimmee is an ideal place to call home.

One of the standout features of Kissimmee’s real estate market is the enchanting collection of homes designed in the Cottage Architectural style. These charming residences exude warmth and character, often featuring quaint gabled roofs, inviting porches, and beautifully landscaped gardens. The cottage style is designed to create a cozy and intimate atmosphere, perfect for families or individuals seeking a serene retreat from the hustle and bustle of everyday life.

Living in a cottage-style home in Kissimmee means you can enjoy the best of both worlds. Picture yourself sipping your morning coffee on a sun-drenched porch, surrounded by lush greenery and the soothing sounds of nature. With the city’s close proximity to world-renowned attractions such as Walt Disney World and Universal Studios, you’ll find that adventure is just around the corner.

Whether you’re drawn to the rich cultural heritage, the outdoor recreational opportunities, or the charming architecture, Kissimmee is a place where dreams come to life. Explore the enchanting cottage homes available in this delightful city, and discover a new way of living that embraces comfort, charm, and community.

Newest Kissimmee Homes with Cottage Architectural style

$305,000
3 Beds ⋅ 1 Baths ⋅ E B Waters & Sons Add SubDv. ⋅ 34741 Zip Code
Welcome to this charming 3-bedroom, 1-bath home situated on an oversized lot with no HOA restrictions. Whether you need space for your RV, boat, work trailer, or recreational vehicles, this property offers the flexibility and freedom that is increasingly difficult to find. The spacious lot provides endless possibilities for outdoor living, entertaining, gardening, or future expansion. Inside, you'll find a functional floor plan with comfortable living spaces ready for a new owner to make their own. Conveniently located near shopping, dining, schools, medical facilities, and major roadways, this property combines everyday convenience with the privacy and flexibility of homeownership without HOA oversight. Perfect for first-time homebuyers, investors, or anyone looking for extra space and storage, this property is a rare opportunity to own a large lot with room to live the lifestyle you want.

704 S Clyde Avenue, Kissimmee
$585,999
4 Beds ⋅ 5 Baths ⋅ Rolling Oaks Ph 6 SubDv. ⋅ 34747 Zip Code
SELLER MOTIVATED - CALL TO SEE IT TODAY It’s 5 O’clock right here in the world-renowned Margaritaville Resort Orlando! This FULLY FURNISHED spectacular, carpet-free luxury home features durable tile flooring and ceiling fans throughout, offering 4 generously sized bedrooms, each equipped with its own private en-suite bathroom. The kitchen opens seamlessly to the main living area, making it perfect for entertaining or vacation hosting. One of the bedrooms has a custom storage closet, setting this home apart from other resort 4 bedrooms. Enjoy the quintessential Florida lifestyle with front balcony access on both the second and third floors, offering incredible nightly views of the theme park fireworks. Located in a pet-friendly community, the monthly HOA covers high-speed internet, digital cable, phone, daily doorstep garbage pickup, professional landscaping, and pest control. The Fins UP Beach Club gives you access to enjoy full access to world-class resort amenities including 7 resort pools, a fitness center/gym, an internal resort shuttle, and free transportation shuttles directly to the local theme parks. This unique resort setup is highly walkable, situated just steps from Island H2O Water Park and Sunset Walk’s vibrant mix of restaurants, bars, live music, Target, and Ulta. Centrally located with lightning-fast access to Disney, Universal, SeaWorld, and Gatorland, this property is a premier choice for a primary residence, second home, or lucrative vacation investment.

8040 Lost Shaker Lane, Kissimmee
$575,000
4 Beds ⋅ 5 Baths ⋅ Margaritaville, Rolling Oaks SubDv. ⋅ 34747 Zip Code
BEST DEAL IN MARGARITAVILLE!!!! This world famous resort exudes cheer with a colorful palette of tropical hues and lush landscaping! Imagine owning a 3 story Island style home drenched in aqua blue with stylish awnings and crisp white balconies, this wins hands down for curb appeal!! Worth mentioning is the quality construction and choice of a concrete tile roof in lieu of shingles and a center of state location! The interior is fully furnished with superbly crafted Ethan Allen furniture guaranteed to last with solid wood construction and durable fabrics, a 55k package. All bedding & linens are from the Margaritaville Hotel, ensuring the same luxurious slumber! Everything is included from tv’s to modems to artwork and silverware! All appliances large and small also convey! Luxury vinyl plank keeps things cohesive and very low maintenance. This floor plan is spacious and gives plenty of privacy to large parties looking to kick back and relax! The backyard has a new hot tub and is a great spot to lounge and enjoy a cocktail or two, because it’s always 5 o’clock somewhere! Yes, it can get catchy…so don’t blow out your flip flop or step on a pop top rushing to see this amazing life you could be living or benefitting from! A cheeseburger in paradise is an understatement with an incredible array of restaurants and specialty shoppes throughout the resort. Sunset Walk offers an array of international delicacies. Dine and dance the night away at Estefan’s Kitchen enjoying decadent Cuban cuisine or pop into the Wharf for fresh seafood, a cold beer and live music! With countless choices and activities you’ll never run out of new experiences to try and savor. On site make a splash at the Island H20 water park, one of the many pools or jump on the free shuttle to the parks! A reservation is required thru Fins Up Beach Resort.

8045 Lost Shaker Lane, Kissimmee
$264,900
2 Beds ⋅ 2 Baths ⋅ Runaway Beach Club SubDv. ⋅ 34746 Zip Code
Turnkey, income-producing opportunity just minutes from Disney! Welcome to this fully furnished 2-bedroom, 2-bath condo located in the highly desirable, short-term rental–approved community of Runaway Beach Club in Kissimmee. This well-designed unit features a bright, open layout with high vaulted ceilings, chair rail accents, and in-unit laundry for added convenience. The split-bedroom floor plan offers privacy for guests, and both bedrooms include spacious walk-in closets. The living area is ideal for hosting, with two queen pull-out sofas to comfortably accommodate additional guests. No carpet—all porcelain tile, recent flooring updates add a modern, low-maintenance touch. Perfect as a vacation home, second residence, or income-producing property, this community allows flexible rental options including daily, weekly, monthly, or long-term stays (Airbnb/VRBO friendly). Runaway Beach Club is a gated, pet-friendly community offering resort-style amenities such as tropical pools, spa, fitness center, indoor basketball court, picnic and BBQ areas, and a scenic lagoon dock. Owners and guests also enjoy access to nearby Calypso Cay amenities, including water slides, mini golf, zip line, rope course, and more. Conveniently located near Disney, Osceola Parkway, and Hwy 192, with easy access to shopping, dining, and major attractions. No CDD fees. Whether you're looking for a turnkey investment or a personal getaway, this property offers excellent value and flexibility. Room sizes are approximate and should be independently verified.

3006 Bonfire Beach Drive Unit 202, Kissimmee
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