Seasons Real Estate

Seasons Real Estate

Welcome to Seasons, a delightful subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming community is a hidden gem that perfectly blends suburban tranquility with easy access to the excitement of Central Florida’s attractions.

Seasons is renowned for its picturesque landscapes and meticulously maintained homes, making it an ideal place for families, retirees, and anyone looking to enjoy the Florida lifestyle. The subdivision features a variety of single-family homes, each designed with modern amenities and a touch of southern charm. Residents can enjoy spacious yards, inviting porches, and a welcoming community atmosphere.

One of the standout features of Seasons is its commitment to community engagement. The neighborhood hosts regular events, fostering connections among residents and creating a sense of belonging. Whether it’s a seasonal celebration or a casual get-together at the community park, there’s always something happening in Seasons.

Conveniently located just minutes away from major highways, Seasons offers easy access to Orlando’s world-famous theme parks, shopping, and dining. Enjoy a day at Walt Disney World or explore the local boutiques and eateries in downtown Kissimmee. The nearby Lake Tohopekaliga provides ample opportunities for fishing, boating, and enjoying Florida's natural beauty.

In Seasons, you’ll find not just a home, but a lifestyle enriched by community spirit, excellent schools, and a wealth of recreational options. Come and discover why Seasons is the perfect place to plant your roots in sunny Kissimmee, Florida!

Newest Listings in Seasons

$507,000
7 Beds ⋅ 6 Baths ⋅ S5153638 MLS
Prime Disney area investment opportunity! This **7 bedroom, 5.5 bathroom** pool home is **sold fully furnished** and located just **15 minutes from Walt Disney World** in one of Central Florida's most desirable vacation rental corridors. Location is everything, and being this close to Disney helps maximize occupancy and minimize vacancy, making it an exceptional opportunity for short term rental investors, a vacation home, or a primary residence. The spacious floor plan features **four private bedroom suites with attached bathrooms, including one on the first floor and three upstairs**, plus an open concept living area, loft, and plenty of room for large families or vacation groups. Enjoy your own private screened pool, perfect for relaxing after a day at the parks. **Located in the highly sought after Seasons community, this home is zoned for short term rentals and is ideally positioned to attract year round vacation guests.** The community features a scenic lake, playground, and a low HOA, which includes community landscaping and grounds maintenance. Conveniently located near Walt Disney World, Universal Orlando, Celebration, Old Town, championship golf courses, shopping, dining, Walmart, Aldi, and major highways. Whether you're looking to generate vacation rental income or enjoy the Florida lifestyle, this unbeatable location has it all.

1265 Seasons Boulevard, Kissimmee

Listing courtesy of KELLER WILLIAMS LEGACY REALTY. murraycoleman@kw.com
$459,950
4 Beds ⋅ 3 Baths ⋅ O6415764 MLS
Welcome to your own piece of Florida paradise in the highly sought-after Seasons community! Located just 10 minutes from Walt Disney World, this beautifully maintained 4-bedroom, 3-bath pool home offers the perfect blend of comfort, convenience, and flexibility. Step inside to discover a spacious split-bedroom floor plan featuring formal living and dining areas, a bright and open family room with soaring vaulted ceilings, and a well-appointed kitchen designed for gathering and entertaining. Large sliding glass doors open to your private screened lanai and heated swimming pool, perfectly positioned with desirable southern exposure for sunshine-filled days all year long. Offered fully furnished and beautifully appointed right down to the last teaspoon, this truly is a turnkey opportunity. Simply bring your suitcase and start enjoying the Florida lifestyle from day one. Whether you're searching for a primary residence, a second home, or a vacation retreat, this home is ready to welcome you. For investors, the property is zoned for short-term rentals and is ideally located within one of Kissimmee's most popular vacation rental communities, just minutes from world-class attractions, golf, shopping, dining, and entertainment. With its exceptional location, versatile floor plan, private pool, and move-in-ready furnishings, this home offers endless possibilities. Live in it full-time, enjoy it as your personal Florida getaway, or continue its success as a vacation rental property—the choice is yours.

1255 Seasons Boulevard, Kissimmee

Listing courtesy of VACAY & CO REAL ESTATE. 863-874-0449
$499,000
6 Beds ⋅ 6 Baths ⋅ O6400453 MLS
The home is located in the boutique, resort style community of SEASONS, a favorite return destination of international and domestic vacationing guests, due to its ideal location. (15 minutes to Disney, and dining choices from famous fast food to 5 star dining.) HOA fees include landscaping and community common area care. The extended driveway offers plenty of parking space, ideal for large families or guests. Whether you're looking for a primary residence with Resort-style living, an exciting vacation home for you & the family, or an income-producing investment property, look no further!

1315 Seasons Boulevard, Kissimmee

Listing courtesy of KICANTO REALTY. 305-744-2297
$370,000
4 Beds ⋅ 3 Baths ⋅ O6377522 MLS
Welcome to this stunning 4-bedroom, 3-bath home located in the desirable Seasons community—perfect as a primary residence, second home, or income-producing vacation rental. This well-designed split floor plan features a formal living and dining area at the front of the home, leading into a spacious kitchen and family room with vaulted ceilings. Large windows and sliding doors open to your private, fully screened, heated pool with southern exposure—ideal for year-round enjoyment and entertaining. The home is offered is zoned for short-term rentals, making it a strong investment opportunity in one of Kissimmee’s most popular vacation corridors. Priced to sell, the property may require a new roof and some cosmetic updates—offering buyers the chance to add value and personalize. Schedule your private showing today or explore the virtual tour to experience everything this home has to presents.

1105 Seasons Boulevard, Kissimmee

Listing courtesy of CENTRIC REALTY SERVICES LLC. 407-421-9391
$550,000
5 Beds ⋅ 3 Baths ⋅ O6357414 MLS
Fully Renovated 5-Bedroom Pool Home with Pond View in Prime Kissimmee Location! Welcome to this beautifully updated corner-lot residence ideally situated in the heart of Kissimmee, just off Highway 192 — offering quick access to shopping, dining, entertainment, and world-famous attractions. This stunning two-story home has been fully renovated to combine modern style with everyday comfort, making it truly move-in ready. Step inside to discover a bright and open floor plan featuring brand-new flooring throughout, fresh interior and exterior paint, and high ceilings that create an inviting sense of space. The fully upgraded kitchen showcases new cabinets, elegant countertops, and ample storage, making it a dream for both everyday living and entertaining. This spacious home offers five bedrooms and three full bathrooms, with the primary suite conveniently located on the main floor for added privacy and comfort. Upstairs, you’ll find additional well-sized bedrooms perfect for family, guests, or a home office. Outdoors, enjoy your very own private screened-in pool overlooking a peaceful pond view, providing the perfect setting for relaxation or weekend gatherings. The extended driveway offers plenty of parking space, ideal for large families or guests. With its prime location, thoughtful upgrades, and elegant design, this home has it all — whether you’re seeking a family residence, vacation retreat, or investment opportunity. Don’t miss your chance to own this beautifully renovated home — schedule your private showing today!

1145 Seasons Boulevard, Kissimmee

Listing courtesy of BLUE CHIP INTERNATIONAL REALTY LLC. 407-988-6543
$12,400
5 Beds ⋅ 4 Baths ⋅ 11504845 MLS
Bring your toothbrush! This fully renovated 5-bedroom, 4.5-bath home is move-in ready with luxurious upgrades. The spacious floor plan includes the primary suite (with a walk-in closet and electric blinds) and a 5th bedroom (converted to a home office) on the main level. Upstairs, find three additional bedrooms, including a large en-suite. Enjoy the oversized pool renovated in 2024 with a saltwater system, cabana bath, and lush landscaping. The 2-car garage and circular driveway offer ample parking and curb appeal. Features: Tesla-level 2 charger (2023) Kitchen: New island (2025) with Sub-Zero fridge, Whirlpool wine cooler, double oven GE, Viking stove, and wall-mounted hood. Security: Wireless camera system with Ring alarm for peace of mind.

6048 NW 30th Way, Boca Raton

Listing courtesy of .

$485,000
4 Beds ⋅ 3 Baths ⋅ TB8350317 MLS
Home is currently being rented on short term rental.

1310 Seasons Boulevard, Kissimmee

Listing courtesy of JACK KELLER INC. 727-586-1497
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