Winter Garden Shores Rep Homes with Dillard Street Elem Elementary school

Winter Garden Shores Rep Homes with Dillard Street Elem Elementary school

Welcome to Winter Garden Shores Rep, a picturesque subdivision nestled in the heart of Winter Garden, Florida. This charming community is a hidden gem in Orange County, offering residents a perfect blend of suburban tranquility and urban convenience. With its lush landscapes and friendly atmosphere, Winter Garden Shores Rep is an ideal place to call home for families, retirees, and everyone in between.

One of the standout features of this delightful neighborhood is its proximity to Dillard Street Elementary School, making it an excellent choice for families with young children. Parents can take comfort in knowing that their kids have access to quality education just a stone's throw away. The school’s commitment to fostering a nurturing and stimulating environment ensures that children thrive both academically and socially.

The homes in Winter Garden Shores Rep boast a variety of architectural styles, catering to diverse tastes and preferences. From cozy single-family residences to spacious modern designs, there’s something for everyone. Many properties feature beautiful yards, perfect for outdoor gatherings or simply enjoying the lovely Florida sunshine.

Living in Winter Garden Shores Rep means you’re just minutes away from downtown Winter Garden, where you can explore a vibrant array of shops, restaurants, and parks. The nearby West Orange Trail offers endless opportunities for outdoor recreation, from biking to walking, allowing residents to embrace an active lifestyle.

Discover the charm and community spirit of Winter Garden Shores Rep—where your dream home awaits in a neighborhood that truly feels like family. Come experience the warmth and beauty of Winter Garden living today!

Newest Winter Garden Shores Rep Homes with Dillard Street Elem Elementary school

505 N Boyd Street, Winter Garden
$618,000
3 Beds ⋅ 2 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
CHARMING VINTAGE HOME IN DOWNTOWN WINTER GARDEN — NO HOA! Huge double lot offers more space for all your dreams! Welcome to the heart of Downtown Winter Garden! This well-maintained, vintage-style 3-bedroom, 2-bath home offers timeless character, a cozy atmosphere, and an incredible location in Winter Garden’s highly desirable Golf Cart District. Inside, you’ll find a warm and inviting living room featuring a real wood-burning brick fireplace, a comfortable living and dining combination, and a convenient pass-through to the kitchen. The spacious, covered, screened-in room provides the perfect setting for entertaining guests, enjoying your morning coffee, or relaxing from the Florida sunshine. There are actually two primary suite bedrooms and a large home office or third bedroom. The home is situated on a corner, double lot so there is room for growth. The home is being offered for purchase AS IS. Enjoy the best of downtown living, where you can stroll or hop on your golf cart to explore the popular Plant Street Market, local restaurants, charming boutiques, cozy cafés, and the beloved Winter Garden Farmers Market. Take a short ride to Veterans Memorial Park for a game of pickleball, enjoy a swim at Farnsworth community pool, stroll or bike along the scenic West Orange Trail, or discover the natural beauty of nearby Lake Apopka and Newton Park. Historic downtown Winter Garden is an official Hallmark Christmas Town for 2026! Come experience the beauty of this friendly town. With NO HOA, a sought-after downtown location, and easy access to major highways, this home offers a wonderful opportunity to enjoy the unique blend of small-town charm and modern convenience that makes Winter Garden so special. Orlando’s attractions, including Walt Disney World, Universal, SeaWorld and multiple water parks are also within convenient driving distance. Only 30 minutes to Orlando airport (MCO). Don’t miss your opportunity to own a home in one of Central Florida’s most loved downtown communities! Schedule your private showing today and experience the charm and lifestyle of Downtown Winter Garden!

505 N Boyd Street, Winter Garden
502 Palm Drive, Winter Garden
$699,700
4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
Experience the PERFECT blend of comfort, charm, and functionality in this UNIQUE Winter Garden home! Featuring 4 bedrooms and 2.5 baths, this spacious residence offers an impressive second-story LOFT and a versatile 4th bedroom with its own half bath—perfect for guests, a MEDIA room, or FLEXIBLE living space. The thoughtfully designed first floor features a private primary suite with an ensuite bath, two additional bedrooms sharing a full bath, a spacious & inviting FAMILY room, and a beautifully appointed kitchen that truly serves as the heart of the home. Kitchen features include built-ins and French doors that open to a gorgeous deck, creating an ideal setting for indoor/outdoor entertaining. A formal dining room and PRIVATE office with French doors provide additional space and convenience. Step outside to enjoy peaceful outdoor living in the EXCEPTIONAL oversized landscaped backyard, complete with a private patio/deck perfect for relaxing or entertaining. A 3-car GARAGE plus a dedicated GOLF CART garage adds exceptional convenience and storage. Located in highly sought-after Downtown Winter Garden, this home is close to top-rated schools, shopping, parks, West Orange Trail, and popular dining destinations. Enjoy the unique lifestyle of a golf-cart-friendly downtown district while being just minutes from everything you need. ON-SITE Generator for Hurricane season (AS/IS) w/sale. Recent updates include a New Roof (2020), New hot water tank (2026), New mini-split for 2nd floor (2026), A/C Main (2023), and fresh interior paint (2026) New Luxury vinyl in Office, 2nd & 3rd Bedrooms. (2026) Buyers....Come discover all this wonderful home has to offer and make it yours!

502 Palm Drive, Winter Garden
205 Surprise Drive, Winter Garden
$1,200,000
4 Beds ⋅ 3 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
Back on the Market due to Buyer's failure to perform. Welcome to Winter Garden, which has been ranked by Money Magazine "Best Places To Live In America" and is a finalist for Hallmark Channel's 2026 "Merriest Christmas Towns" Contest. This exceptional property in the heart of the highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. Priced to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. A large shed, rated as a detached garage, provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. The 3/4 acre property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. SELLER WILL CONSIDER SUB-DIVIDINGTHE LOTS. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.

205 Surprise Drive, Winter Garden
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