Crawfordorlandorealestate.com Search Results

$888,000

One or more photo(s) has been virtually staged. ***NEW REDUCED PRICE!***MOVE IN BEFORE THE HOLIDAYS & TAKE ADVANTAGE OF THE LOWER INTEREST RATES! The sellers are motivated and ready for the next chapter—creating an incredible opportunity for you to own this beautifully updated Craftsman-style home on a rare .53-acre R-2 zoned lot in the heart of Downtown Winter Garden’s golf cart district. Offering character, comfort, and flexibility with no HOA, this property is move-in ready and waiting for your vision—whether that’s an addition, guest house, pool, or even a potential lot split (with city approval). Inside, over 2,200 sq. ft. of living space has been refreshed from top to bottom with thoughtful 2025 updates including a NEW ROOF, fresh interior paint, refinished original hardwood floors, new luxury vinyl plank flooring, new stainless steel French door refrigerator, updated lighting, and refinished rear deck with new railings, stairs, and stain. The floor plan offers multiple gathering spaces, including a spacious family room with wood-burning fireplace, and a custom kitchen equipped with stainless appliances, gas 6-burner cooktop, double ovens, and breakfast bar. The front sunroom provides a bright and versatile space—perfect for a home office, reading nook, or creative studio. Upstairs, the primary suite features hardwood flooring, a generous walk-in closet, and an inviting en-suite bath with a clawfoot tub and tiled shower. Downstairs are two additional bedrooms and a second full bath providing room for family or guests. Outdoor living shines here—enjoy a fully fenced backyard with three wood decks, established butterfly and vegetable gardens, and a 14,000-gallon above-ground pool (2020). The expansive 23x25 main deck is ideal for entertaining, grilling, or simply relaxing in your private oasis. Major system upgrades add even more value: dual HVAC systems (2019 & 2020), Rinnai tankless gas water heater (2023–24), updated electrical panels (2005 & 2020), termite tenting with transferable bond (2025), and an oversized 2-car garage with new openers (2023 & 2025). A charming enclosed breezeway with Saltillo tile flooring and tongue-and-groove ceiling (2025) connects the home to the garage and an attached storage building—perfect for hobbies or workshop space. Located just blocks from the West Orange Trail, Plant Street Market, the weekly Farmers Market, and all of Winter Garden’s award-winning restaurants, coffee shops, and boutiques, this home offers an unbeatable blend of lifestyle and location. The holiday season in Winter Garden is one of the most beautiful times of the year. This beautiful property is the perfect place to start the new year!

3 Beds ⋅ 3 Baths ⋅ Pleasant Park SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. ***NEW REDUCED PRICE!***MOVE IN BEFORE THE HOLIDAYS & TAKE ADVANTAGE OF THE LOWER INTEREST RATES! The sellers are motivated and ready for the next chapter—creating an incredible opportunity for you to own this beautifully updated Craftsman-style home on a rare .53-acre R-2 zoned lot in the heart of Downtown Winter Garden’s golf cart district. Offering character, comfort, and flexibility with no HOA, this property is move-in ready and waiting for your vision—whether that’s an addition, guest house, pool, or even a potential lot split (with city approval). Inside, over 2,200 sq. ft. of living space has been refreshed from top to bottom with thoughtful 2025 updates including a NEW ROOF, fresh interior paint, refinished original hardwood floors, new luxury vinyl plank flooring, new stainless steel French door refrigerator, updated lighting, and refinished rear deck with new railings, stairs, and stain. The floor plan offers multiple gathering spaces, including a spacious family room with wood-burning fireplace, and a custom kitchen equipped with stainless appliances, gas 6-burner cooktop, double ovens, and breakfast bar. The front sunroom provides a bright and versatile space—perfect for a home office, reading nook, or creative studio. Upstairs, the primary suite features hardwood flooring, a generous walk-in closet, and an inviting en-suite bath with a clawfoot tub and tiled shower. Downstairs are two additional bedrooms and a second full bath providing room for family or guests. Outdoor living shines here—enjoy a fully fenced backyard with three wood decks, established butterfly and vegetable gardens, and a 14,000-gallon above-ground pool (2020). The expansive 23x25 main deck is ideal for entertaining, grilling, or simply relaxing in your private oasis. Major system upgrades add even more value: dual HVAC systems (2019 & 2020), Rinnai tankless gas water heater (2023–24), updated electrical panels (2005 & 2020), termite tenting with transferable bond (2025), and an oversized 2-car garage with new openers (2023 & 2025). A charming enclosed breezeway with Saltillo tile flooring and tongue-and-groove ceiling (2025) connects the home to the garage and an attached storage building—perfect for hobbies or workshop space. Located just blocks from the West Orange Trail, Plant Street Market, the weekly Farmers Market, and all of Winter Garden’s award-winning restaurants, coffee shops, and boutiques, this home offers an unbeatable blend of lifestyle and location. The holiday season in Winter Garden is one of the most beautiful times of the year. This beautiful property is the perfect place to start the new year!

524 S Lakeview Avenue, Winter Garden

$550,000

Welcome to this breathtaking 4-bedroom, 2-bathroom CUSTOM BUILT home, ideally located ONE MINUTE from the heart of Historic Downtown Winter Garden. And with a NEW ROOF, NEWER AC system, and NO HOA, this home delivers tremendous value and peace of mind for years to come. Tucked away on a quiet dead-end street, this property offers both privacy and peace of mind — an ideal setting for families. Inside, you’ll find bamboo flooring throughout, soaring ceilings in the living room, EVERY SINGLE ROOM being OVERSIZED, and an open layout that feels bright, spacious, and inviting. The kitchen features generous counter space and seamlessly connects to the living and dining areas, making it perfect for both everyday life and entertaining. The flexible dining room could easily double as a home office or study, depending on your lifestyle needs. Step outside to your own backyard oasis — complete with an outdoor kitchen, expansive yard space, and plenty of room to add a pool if desired. Don’t miss your chance to own a spacious home in one of Central Florida’s most desirable areas — just moments from Winter Garden’s dining, shopping, and trails!

4 Beds ⋅ 2 Baths ⋅ Pleasant Park SubDv. ⋅ 34787 Zip Code

Welcome to this breathtaking 4-bedroom, 2-bathroom CUSTOM BUILT home, ideally located ONE MINUTE from the heart of Historic Downtown Winter Garden. And with a NEW ROOF, NEWER AC system, and NO HOA, this home delivers tremendous value and peace of mind for years to come. Tucked away on a quiet dead-end street, this property offers both privacy and peace of mind — an ideal setting for families. Inside, you’ll find bamboo flooring throughout, soaring ceilings in the living room, EVERY SINGLE ROOM being OVERSIZED, and an open layout that feels bright, spacious, and inviting. The kitchen features generous counter space and seamlessly connects to the living and dining areas, making it perfect for both everyday life and entertaining. The flexible dining room could easily double as a home office or study, depending on your lifestyle needs. Step outside to your own backyard oasis — complete with an outdoor kitchen, expansive yard space, and plenty of room to add a pool if desired. Don’t miss your chance to own a spacious home in one of Central Florida’s most desirable areas — just moments from Winter Garden’s dining, shopping, and trails!

18 Cooledge Street, Winter Garden

$440,000

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.

3 Beds ⋅ 2 Baths ⋅ Pleasant Park SubDv. ⋅ 34787 Zip Code

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