Osceola Homes with Cottage Architectural style

Osceola Homes with Cottage Architectural style

Welcome to Osceola County, Florida – a hidden gem nestled in the heart of the Sunshine State. Known for its vibrant communities, natural beauty, and rich history, Osceola County offers a perfect blend of urban convenience and serene landscapes. From the bustling streets of Kissimmee to the tranquil shores of Lake Tohopekaliga, residents enjoy a diverse array of recreational activities, cultural experiences, and a warm, welcoming atmosphere.

Among the many delightful architectural styles found in Osceola, the charming cottage homes stand out as a picturesque choice for those seeking a cozy and inviting living space. With their quaint facades, steeply pitched roofs, and whimsical details, cottage-style homes embody a sense of nostalgia and charm that captures the essence of Florida's laid-back lifestyle. These homes often feature lush gardens, inviting porches, and unique character that make them feel like a retreat from the everyday hustle and bustle.

Living in an Osceola County cottage means more than just enjoying a beautiful home; it’s about embracing a lifestyle steeped in community and nature. Picture yourself sipping coffee on your front porch, surrounded by the gentle sounds of nature, or hosting friends for a barbecue in your backyard oasis. With access to local parks, outdoor adventures, and a vibrant downtown, your cottage home will be the perfect sanctuary to unwind and connect with the beauty of Florida living.

Whether you're a first-time buyer or looking for a charming getaway, Osceola County's cottage homes offer a unique opportunity to experience the best of Florida's real estate. Discover your dream home today in this enchanting region!

Newest Osceola Homes with Cottage Architectural style

$875,000
6 Beds ⋅ 6 Baths ⋅ Split Oak Estates SubDv. ⋅ 34771 Zip Code
Virtually Staged. Luxury, space and resort-style living between Lake Nona and Sunbridge. Welcome to this exceptional estate home in desirable Split Oak Estates, where more than 5,200 square feet of living space meets an unforgettable resort-style outdoor retreat. Conveniently off Cyrils Drive, this six-bedroom, 5.5-bath residence offers exceptional space, flexibility and an elevated lifestyle, just minutes from Lake Nona Town Center and at the doorstep of the rapidly growing Sunbridge corridor. The showstopper is the backyard. A spacious screened lanai surrounds a heated saltwater pool and spa, creating a private resort-style escape designed for relaxing, entertaining and making the most of Florida living. The pool was resurfaced in 2026, and a gas hookup is in place for an outdoor grill, making this impressive entertaining space ready for your next gathering. Inside, the thoughtfully designed floor plan delivers room for everyone. The first-floor primary suite offers a peaceful retreat with a granite dual vanity, walk-in shower and a convenient stackable washer and dryer tucked into a generously sized, professionally designed walk-in closet. Upstairs, five additional bedrooms provide exceptional flexibility, with three featuring private en-suite baths. Every bedroom includes a walk-in closet and ceiling fan. A second full laundry room, generous bonus room and versatile media room, ideal for a home theater, office or additional living space, complete the upper level. At the heart of the home, the kitchen opens seamlessly to the gathering room and features granite countertops, an oversized island, white shaker cabinetry, tile backsplash, stainless-steel appliances including a Bosch dishwasher, and a huge walk-in pantry with custom shelving. Tile flooring flows throughout the flex room, dining room, gathering room and kitchen, creating a cohesive and inviting main living space. Additional highlights include two water heaters replaced within the past year, and two water softeners in the three-car garage. Residents of Split Oak Estates also enjoy access to a community pool, cabana and playground. Lake Nona Town Center's shopping, dining and entertainment are approximately three miles away, while Orlando International Airport is about 15 minutes away with convenient access to SR 417 and SR 528. Downtown Orlando is approximately 30 minutes away. More than a home, this is a lifestyle, with exceptional space, thoughtful design and a private resort-style backyard, all ideally positioned between Lake Nona and the Sunbridge corridor. Schedule your private showing today.

2873 Matera Drive, St Cloud
$110,000
1 Beds ⋅ 1 Baths ⋅ Shady Oaks SubDv. ⋅ 34739 Zip Code
Calling all snowbirds, investors, and anyone searching for true peace and quiet! Welcome to 200 Lake Marian Road, a completely renovated, cabin-inspired home tucked away in the peaceful countryside of Kenansville. This charming one-bedroom, one-bathroom home has been thoughtfully updated throughout, creating a warm and inviting space that is truly move-in ready. Step inside to discover all-new flooring, windows, interior lighting, appliances, and water heater. Beautiful wood accents add rustic character and create the cozy feeling of a private cabin retreat, while thoughtfully designed storage helps maximize the space. The single-story layout offers comfortable, simple, and low-maintenance living.The property also features a durable metal roof, septic system, and an additional storage shed—perfect for tools, outdoor equipment, or recreational gear. Located near Lake Marian, this home offers peaceful country living with boating, fishing, and outdoor recreation nearby. Whether you’re searching for a full-time residence, seasonal Florida escape, weekend getaway, rental property, or affordable investment opportunity, this quaint and turnkey home offers so many possibilities. Come enjoy the fresh air, peaceful surroundings, and slower pace of country living. Schedule your private showing today! CASH ONLY!

200 Lake Marian Road, Kenansville
$1,290,000
4 Beds ⋅ 4 Baths ⋅ Oakwood Shores SubDv. ⋅ 34771 Zip Code
Experience the best of Central Florida lakefront living on Trout Lake, part of the Alligator Chain of Lakes, with this exceptional custom-built home located at 6805 Bass Highway in St. Cloud. Offering a rare combination of luxury, privacy, and investment potential, this stunning waterfront property is perfectly suited as a primary residence, second home, or vacation rental — all with NO HOA restrictions. Ideally positioned within one hour of Walt Disney World Resort and Universal Orlando Resort, Orlando’s world-famous attractions, and Florida’s beautiful east coast beaches, and just 30 minutes from Lake Nona and the Orlando International Airport this property offers the perfect balance of peaceful lakefront living and convenient access to everything Central Florida has to offer. Built in 2014, this impressive 3,535-square-foot custom home features 4 bedrooms, 4 bathrooms, and thoughtfully designed living spaces filled with high-end upgrades and custom details throughout. From the moment you enter, you’ll appreciate the upgraded cabinetry, premium countertops, designer fixtures, upgraded flooring, and beautifully finished stained concrete surfaces that create a warm yet modern lakefront aesthetic. The spacious chef’s kitchen was designed with both functionality and entertaining in mind, featuring extensive custom cabinetry and an expansive hidden walk-in pantry that provides exceptional storage and organization. Throughout the home, you’ll find numerous built-in storage areas, window seats in most bedrooms, and carefully crafted details that add both charm and practicality. The primary suite offers a luxurious private retreat complete with a dedicated vanity/glam room and generous storage solutions. Upstairs, a versatile bonus room provides endless possibilities and can easily function as a home office, media room, playroom, or be converted into an additional bedroom. Additional flexible living spaces include a separate air-conditioned room ideal for a home gym, hobby room, or flex space, along with a dedicated air-conditioned laundry room conveniently located off the garage. The property also includes multiple outdoor storage sheds, offering even more room for tools, lake toys, and equipment. Set on 160 feet of fully cleared lakefront, the property showcases breathtaking water views, a private sand beach area, and direct access to the highly sought-after Alligator Lake Chain — a connected chain of five lakes known for boating, fishing, and watersports. The outdoor amenities are truly exceptional. A brand-new 110-foot dock features a covered metal roof, electric boat lift, lakeside sitting area, and propane fire pit, creating the ultimate waterfront gathering space. The expansive 600-square-foot fully enclosed screened outdoor kitchen overlooks the lake and offers year-round enjoyment for entertaining family and guests. An additional lakeside fire pit area further enhances the unmatched outdoor lifestyle this property provides. Major recent upgrades include a roof and exterior paint both completed just 2 years ago, adding long-term value and peace of mind. This is a rare opportunity to own a true Central Florida lakefront lifestyle property with freedom, luxury, space, and exceptional vacation rental potential!

6805 Bass Highway, St Cloud
$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
$794,000
7 Beds ⋅ 4 Baths ⋅ Lake Front Add To Town Of St. Cloud SubDv. ⋅ 34769 Zip Code
One or more photo(s) has been virtually staged. Discover space, character, and flexibility in this unique 7-bedroom, 4-bathroom custom home. From the grand two-story entry to the spacious layout, this property is designed for comfort, entertaining, and everyday living—with thoughtful details throughout. It has been meticulously designed to maximize storage, with almost every inch of the house used for living space or storage. One of the standout features is the separate 1-bedroom, 1-bath apartment/in-law suite, complete with its own living room and private entrance, as well as interior access through the enclosed sunroom connected to the primary suite. This flexible space is ideal for guests, extended family, or even creating a future rental opportunity, with the ability to build a kitchenette. The main home boasts a spacious and elegant floor plan with formal and casual living areas that include a formal living room, formal dining room, a cozy breakfast nook, and a large office or den—perfect for working from home. The grand piano in the family room is also included in the sale, adding a touch of elegance to the space. The kitchen area is enhanced by a butler’s pantry and plenty of room to entertain or prep for big gatherings. Retreat to the luxurious primary suite, which features a large walk-in closet, dual vanities, a soaking tub, and a walk-in shower. From the suite, step into your own enclosed sunroom with AC and plantation shutters, offering beautiful views of the lake beyond. Outdoors, the property continues to impress with a wood-burning fireplace, open yard space with room for a chicken coop or kids’ play area, and a 3-car garage. One bay has been converted into a workshop or office space, but it can easily be returned to a full garage setup. A new roof was installed in 2021, providing added peace of mind. Located just one block from East Lake Tohopekaliga and Lakefront Park, you’ll enjoy quick access to the marina, splash pads, playgrounds, volleyball courts, boat slip rentals, and popular Crabby’s on the Lakefront restaurant. And with no HOA, you have the freedom to truly make this property your own. Whether you're looking for space to spread out, room to entertain, or a flexible floor plan that adapts to your lifestyle, this custom home delivers it all. Schedule your private showing today and explore everything this remarkable home has to offer!

910 Cypress Avenue, St Cloud
Start Your Search