Pleasant Park Homes for Sale

Pleasant Park Homes for Sale

Welcome to Pleasant Park, a charming subdivision nestled in the heart of Winter Garden, Florida, within the vibrant Orange County. This picturesque community is designed for those who appreciate the perfect blend of suburban tranquility and urban convenience. With its tree-lined streets and beautifully landscaped yards, Pleasant Park offers a welcoming atmosphere that feels like home from the moment you arrive.

The homes for sale in Pleasant Park are truly a sight to behold. Ranging from cozy single-family residences to spacious multi-bedroom homes, there’s something to suit every lifestyle and taste. Many of these properties boast modern amenities, open-concept layouts, and inviting outdoor spaces perfect for entertaining or enjoying quiet evenings under the stars. Families will appreciate the proximity to top-rated schools, parks, and recreational facilities, making it an ideal location for raising children.

Living in Pleasant Park means you’re just minutes away from Winter Garden’s charming downtown area, where you can explore delightful shops, dine at local eateries, and enjoy community events throughout the year. The nearby West Orange Trail offers miles of scenic paths for walking, biking, and jogging, catering to outdoor enthusiasts.

If you’re seeking a community that combines comfort, convenience, and a sense of belonging, look no further than Pleasant Park. With homes for sale that cater to a variety of needs, now is the perfect time to discover your dream home in this delightful Winter Garden neighborhood. Come and experience the warmth and charm of Pleasant Park—you won’t want to leave!

Newest Pleasant Park Homes for Sale

$450,000
3 Beds 2 Baths O6417750 MLS
Welcome to 217 W. Story Road, a beautifully located home in Downtown Winter Garden, Florida, offering the walkable, golf cart friendly lifestyle that has made Winter Garden real estate some of the most sought after in Central Florida. Situated just a few blocks from the iconic Plant Street Market, this home places you in the center of everything that makes historic Downtown Winter Garden one of the area's premier destinations. Enjoy convenient access to local restaurants, boutique shopping, coffee shops, breweries, and the award winning West Orange Trail. Spend your weekends at the popular Winter Garden Farmers Market, live entertainment events, and seasonal festivals, all just minutes from your front door. Located in the highly desirable golf cart district, residents can easily access Downtown Winter Garden's newest restaurants and exciting developments that continue to enhance the area's charm and long term appeal. With close proximity to Winter Garden Village, major highways, Walt Disney World, and all that Central Florida has to offer, this location combines small town character with modern convenience. Whether you're searching for a home near Plant Street Market, a property in the golf cart district, or a home in historic Downtown Winter Garden, 217 W. Story Road offers a rare opportunity to experience one of the most desirable lifestyles in Winter Garden, FL.

217 W Story Road, Winter Garden

Listing courtesy of COMPASS FLORIDA LLC. 407-203-9441

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© 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved. This data is up-to-date as of . For the most current information, contact William Raveis Real Estate.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.