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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!

3 Beds ⋅ 2 Baths ⋅ O6450850 MLS

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

$699,700

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!

4 Beds ⋅ 3 Baths ⋅ O6436846 MLS

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

$455,000

Fully Renovated and Move-In Ready! This beautiful 4-bedroom, 2-bath home features a spacious open-concept layout with bright and modern living areas. The designer kitchen showcases premium-quality cabinetry and elegant quartz countertops, perfect for both everyday living and entertaining. Enjoy relaxing in the screened porch or take advantage of the large backyard, ideal for gatherings, BBQs, or simply enjoying your outdoor space. A perfect blend of style, comfort, and functionality — don’t miss this opportunity!

4 Beds ⋅ 2 Baths ⋅ S5156876 MLS

Fully Renovated and Move-In Ready! This beautiful 4-bedroom, 2-bath home features a spacious open-concept layout with bright and modern living areas. The designer kitchen showcases premium-quality cabinetry and elegant quartz countertops, perfect for both everyday living and entertaining. Enjoy relaxing in the screened porch or take advantage of the large backyard, ideal for gatherings, BBQs, or simply enjoying your outdoor space. A perfect blend of style, comfort, and functionality — don’t miss this opportunity!

113 W Division Street, Winter Garden

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