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420 E Cypress Street, Winter Garden
$400,000
3 Beds ⋅ 2 Baths ⋅ Overstreet Crate SubDv. ⋅ 34787 Zip Code
Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.

420 E Cypress Street, Winter Garden
1606 Beulah Road, Winter Garden
$399,900
3 Beds ⋅ 2 Baths ⋅ Orange Cove SubDv. ⋅ 34787 Zip Code
LOCATION, LOCATION, LOCATION, Exceptional value is found with this spacious 3 bedroom, 2 bathroom home. You will appreciate the fully remodeled home with new flooring, kitchen cabinets and countertops, hall and master bathrooms, roof, water heater, pluming, and covered porch. This property is located across the street from Winter Garden High School and 5 minutes away from downtown Winter Garden and convenient access to major highways.

1606 Beulah Road, Winter Garden
2017 Portcastle Circle, Winter Garden
$399,900
3 Beds ⋅ 3 Baths ⋅ Stone Crk A-1 & A-2 SubDv. ⋅ 34787 Zip Code
Location, location, location! Great opportunity to purchase a two-story 3/2.5 with a loft on the second floor and a fully fenced-in yard. The bright and functional floor plan offers plenty of room for comfortable everyday living and entertaining. The kitchen features granite countertops and stainless-steel appliances, while the spacious living areas provide a welcoming atmosphere throughout the home. Enjoy your new home!

2017 Portcastle Circle, Winter Garden
689 Bethune Avenue, Winter Garden
$397,000
4 Beds ⋅ 2 Baths ⋅ Joe Louis Park Q162 SubDv. ⋅ 34787 Zip Code
PHENOMENAL Double corner LOT NO HOA, newer updates INCLUDE: brand new AC, new roof, Re-Plumb, house/ Electrical Panel/rewired. Updated kitchen and bathrooms, Located off the Kitchen is the Dining room area which is open to the Living Room area. The master Bathrooms is completely updated features a standing shower. The Laundry is located inside. The carport/workshop is spacious to hold 2 cars and storage. Enjoy the nice-sized Backyard with a that is big enough for the whole family. You don't want to miss this opportunity to make this house your home! very nice WORKSHOP ** VALUE IS IN THE both property/land

689 Bethune Avenue, Winter Garden
884 Klondike Street, Winter Garden
$372,500
4 Beds ⋅ 2 Baths ⋅ Loveless J S Add 01 SubDv. ⋅ 34787 Zip Code
Welcome to Historic Winter Garden, Florida. NO HOA! Where small-town charm, community, and modern living come together, and you keep more of what's yours with no HOA fees. Built in 2023, this beautifully designed 4-bedroom, 2-bath home with a 1-car garage offers the perfect blend of contemporary comfort and timeless neighborhood character. Start your mornings on the inviting front porch, the ideal spot for coffee, fresh air, and easy neighborhood conversations. Step inside to an open-concept layout that feels bright, spacious, and instantly welcoming, whether you're hosting friends or enjoying a quiet evening in. The modern kitchen impresses with granite countertops, sleek cabinetry, and a generous workspace that flows seamlessly into the main living areas. Laminate flooring throughout the main living spaces adds a clean, low-maintenance finish. Beyond your front door, downtown Winter Garden is just minutes away, a historic district one of Central Florida's most beloved. Spend your weekends at the popular Saturday Farmers Market, dining at local restaurants ranging from cozy cafés to fine-dining establishments, or soaking up the seasonal festivals and community events that give this area its unmistakable energy. Newer construction. Modern finishes. A welcoming, active community. And no HOA. This Winter Garden gem checks every box, so don't miss your chance to make it yours.

884 Klondike Street, Winter Garden
159 9th Street, Winter Garden
$369,900
3 Beds ⋅ 2 Baths ⋅ Loveless J S Add 01 SubDv. ⋅ 34787 Zip Code
Built in 2024, this well-kept 3-bedroom, 2-bath home in the heart of Winter Garden gives you modern construction without the new-build wait. The open-concept layout connects the kitchen, with its stainless appliances, to the living and dining areas. The owner’s suite has a private en-suite bath, and two more bedrooms work well for guests or a home office. An attached garage and a newer roof and systems mean low-maintenance living from day one. You’re minutes from Plant Street’s dining, the Saturday Farmers Market and the West Orange Trail, with easy access to SR-429 and the Turnpike. Schedule your showing today!

159 9th Street, Winter Garden
1444 Kenny Court, Winter Garden
$350,000
3 Beds ⋅ 2 Baths ⋅ Kenny Court SubDv. ⋅ 34787 Zip Code
Welcome to this inviting 3-Bedroom, 2-Bath single-story home in a DESIRABLE LOCATION near Winter Garden, offering a spacious CORNER LOT, NO HOA and plenty of room to make the most of Florida living! Set on NEARLY A QUARTER ACRE, the property features MATURE SHADE TREES, a large driveway with ample parking and a welcoming setting. Inside, BEAUTIFUL LVP FLOORING and NEW LEVELOR BLINDS throughout, create a fresh, cohesive look, while NEW AC (2026) and a ROOF REPLACED IN 2022 add peace of mind. The OPEN FLOOR PLAN allows the Living Room, Dining Room and Kitchen to flow together seamlessly, creating a comfortable setting, while NATURAL LIGHT fills the space, enhancing the bright and airy feel. The Kitchen offers plenty of SOLID WOOD WHITE CABINETRY, solid-surface countertops and a center island with breakfast bar seating. A RECENTLY UPDATED TILE BACKSPLASH adds a stylish finishing touch, while STAINLESS STEEL APPLIANCES—including a GAS STOVE—make meal preparation a pleasure. A window above the sink brings in NATURAL LIGHT and provides a view of the backyard, and a CONVENIENT LAUNDRY ROOM is located just off the Kitchen. Down the hallway, you’ll find THREE BEDROOMS, each featuring a STYLISH CEILING FAN and WALK-IN CLOSET for comfortable living and convenient storage. The Primary Suite presents a private retreat with its own en suite Bath, complete with a MODERN VANITY AND TILED WALK-IN SHOWER. A SECOND FULL BATH with a modern vanity and tub/shower combination, is conveniently located near the additional Bedrooms.The Kitchen provides access to the backyard, where there's an OPPORTUNITY to create an outdoor space that reflects your own style, whether you envision a GARDEN, entertaining area or a place to relax under the Florida sunshine. With its GENEROUS CORNER LOT, mature shade trees and NO HOA, there’s room to make this property your own. Enjoy a GREAT LOCATION, just 2 miles from the charm and character of HISTORIC DOWNTOWN WINTER GARDEN, where you can explore local shops and restaurants, browse the popular PLANT STREET MARKET, visit the SATURDAY FARMERS MARKET or catch a show at the GARDEN THEATRE. Outdoor enthusiasts will appreciate the nearby WEST ORANGE TRAIL, ideal for biking, jogging and leisurely strolls, and with CONVENIENT ACCESS to Florida's Turnpike and SR-429, you can easily reach Orlando’s WORLD-FAMOUS THEME PARKS. Families will appreciate the nearby GREAT SCHOOLS including, A-RATED William Maxey Elementary and West Orange High School, adding to the appeal. With its thoughtful updates, GENEROUS LOT and convenient access to everything WINTER GARDEN has to offer, this home is FULL OF POTENTIAL and ready for its next chapter. Call and schedule your private tour today!

1444 Kenny Court, Winter Garden
483 Pennsylvania Avenue, Winter Garden
$334,000
2 Beds ⋅ 2 Baths ⋅ East Garden Manor Add 03 SubDv. ⋅ 34787 Zip Code
Seller its offering $6,000 for buyers closing costs. Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roof, new plumbing, close to major roads, schools, minutes to Winter Garden dawn town.

483 Pennsylvania Avenue, Winter Garden
338 Windford Court, Winter Garden
$325,000
3 Beds ⋅ 2 Baths ⋅ Park Ave Estates SubDv. ⋅ 34787 Zip Code
Discover this move-in ready 3-bedroom, 2-bathroom CBS construction home in Winter Garden, FL, nestled in the highly sought-after Park Avenue Estates community. Just minutes from downtown Winter Garden, award-winning dining, shopping, and the popular farmers market, this home offers the perfect mix of charm and convenience. Featuring a newer roof, a low HOA, and access to a community pool, you’ll enjoy a relaxed lifestyle in one of Central Florida’s most vibrant neighborhoods. The nearby West Orange Trail is perfect for biking, morning runs, or evening strolls surrounded by Florida’s natural beauty. This move-in ready home places you close to everything, from boutiques and restaurants to top-rated Winter Garden schools. Whether you’re enjoying local amenities or simply relaxing at home, this property provides the ideal opportunity to experience the best of Winter Garden living.

338 Windford Court, Winter Garden

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