Winter Garden Real Estate

Homes for Sale in Winter Garden, FL Between $300,000 to $400,000

Welcome to your dedicated resource for Homes for Sale Between $300,000 to $400,000 in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Winter Garden, FL agents, Zen Home Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $300,000 to $400,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Winter Garden, FL Homes for Sale Between $300,000 to $400,000

11275 Silver Trumpet Loop, Winter Garden
$400,000
2 Beds ⋅ 2 Baths ⋅ Esplanade At Mckinnon Groves SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Corner Lot | Close to Park | Dedicated Study | Spacious Kitchen. New Construction – October Completion! Welcome to the Caicos at 11275 Silver Trumpet Loop in Esplanade at McKinnon Groves! This thoughtfully designed home features an open-concept layout that blends the great room, dining area, and spacious kitchen into one inviting living space. The kitchen offers plenty of room for meal preparation and entertaining, while the covered extended lanai creates a seamless connection to outdoor living. Tucked away at the rear of the home, the private primary suite features a well-appointed bath and generous walk-in closet. A secondary bedroom, full bath, and versatile study provide flexible space for guests, hobbies, or a home office. A convenient laundry room and two-car garage add everyday functionality. Additional Highlights Include: double pocket doors at study, extended lanai, garden fence, and extended tile flooring. Photos are for representative purposes only. MLS#O6427248. Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

11275 Silver Trumpet Loop, Winter Garden
721 S Woodland Street, Winter Garden
$400,000
2 Beds ⋅ 1 Baths ⋅ Borders & Woosley Sub SubDv. ⋅ 34787 Zip Code
Located within Winter Garden’s golf cart district and just minutes from Plant Street, this property offers a distinctive combination of current residential use, C-2 General Commercial zoning, and no HOA. The single-story, concrete-block home includes 2 bedrooms, 1 bathroom, 1,034 square feet of heated living space, an enclosed porch that provides additional flexible space, and a roof replaced in 2023. The interior is ready for renovation, allowing the next owner to update the property according to their intended use and vision. Situated on an approximately 0.19-acre homesite, the property also features mature shade trees, a concrete driveway, and fenced sections of the yard. Its central Winter Garden location provides convenient access to the restaurants, shops, farmers market, community events, and West Orange Trail surrounding downtown and Plant Street, while nearby golf-cart-friendly roadways offer another way to explore the area. Whether considered for continued residential use, a renovation project, or a future business opportunity, this property presents a range of possibilities in a well-connected location. Buyers should independently verify all intended uses, permitting requirements, and zoning regulations with the City of Winter Garden.

721 S Woodland Street, Winter Garden
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
W Orange Country Club Drive, Winter Garden
$400,000
34787 Zip Code
This is a wetland property. W Orange Country Club Drive in Winter Garden, Florida 34787. "Zoning: C-2" Nestled in a desirable and well-established area. This county currently is not allowing anything to be built on it. Pin Location: Latitude 28.49896925, Longitude -81.58828662. Note: buyers I emphasize the importance of conducting thorough due diligence to ensure that the property meets your expectations and requirements.

W Orange Country Club Drive, Winter Garden
5705 New Independence Parkway, Winter Garden
$399,900
3 Beds ⋅ 2 Baths ⋅ Signature Lakes - Phase 2 SubDv. ⋅ 34787 Zip Code
WELCOME HOME TO 5705 NEW INDEPENDENCE PARKWAY! Discover the perfect blend of COMFORT, CHARM, and RESORT-STYLE LIVING in the highly desirable INDEPENDENCE / SIGNATURE LAKES COMMUNITY of WINTER GARDEN, FLORIDA! This inviting 3-BEDROOM, 2.5-BATH TOWNHOME offers 1,751 SQ. FT. OF LIVING SPACE, a PRIVATE REAR-ENTRY 2-CAR GARAGE, and a wonderful opportunity to enjoy everything that makes Central Florida living so special. From the moment you arrive, the CHARMING FRONT PORCH welcomes you home. Step inside to discover a bright, OPEN-CONCEPT FLOOR PLAN filled with NATURAL LIGHT, creating a comfortable setting for everyday living, entertaining friends, or simply unwinding after a long day. The SPACIOUS KITCHEN features GRANITE COUNTERTOPS, generous cabinet storage, and plenty of room to gather, while UPDATED LAMINATE FLOORING adds warmth throughout the main living areas. A NEWER HVAC SYSTEM INSTALLED IN 2025 provides an added touch of comfort and peace of mind. Upstairs, the PRIMARY SUITE offers a relaxing retreat with a PRIVATE ENSUITE BATHROOM and WALK-IN CLOSET. Two additional bedrooms provide flexible space for guests, hobbies, or a HOME OFFICE. Whether you're enjoying your morning coffee on the FRONT PORCH, hosting dinner with loved ones, or relaxing on the PRIVATE PATIO, this home offers room to create lasting memories. Life in INDEPENDENCE is about so much more than the home itself! Residents enjoy an exceptional collection of RESORT-STYLE AMENITIES, including TWO COMMUNITY POOLS, FITNESS CENTERS, a CLUBHOUSE, PARKS, PLAYGROUNDS, DOG PARKS, TENNIS AND BASKETBALL COURTS, SCENIC WALKING TRAILS, and COMMUNITY LAKE ACCESS. Neighborhood gatherings and community events create opportunities to connect, unwind, and truly feel at home. And the LOCATION is equally impressive! Nestled in the heart of HORIZON WEST, you're conveniently located near HAMLIN TOWN CENTER, HISTORIC DOWNTOWN WINTER GARDEN, the WEST ORANGE TRAIL, and WALT DISNEY WORLD, with easy access to shopping, dining, entertainment, major roadways, and area schools. LOCATION, COMFORT, COMMUNITY, AND RESORT-STYLE LIVING — ALL IN ONE PLACE! With 3 BEDROOMS, 2.5 BATHROOMS, 1,751 SQ. FT., A PRIVATE 2-CAR GARAGE, and an incredible array of NEIGHBORHOOD AMENITIES, 5705 NEW INDEPENDENCE PARKWAY is more than just a place to live — it's a place to feel at HOME. WELCOME HOME TO INDEPENDENCE, WINTER GARDEN!

5705 New Independence Parkway, 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
14501 Grove Resort Avenue Unit 1318, Winter Garden
$399,900
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
OWN this full POOL-VIEW condominium in the MAIN building!!! As you enter this 3rd floor two bedroom, two bathroom unit, an unobstructed view to the Springs Pool welcomes you in the Premier Tower or Building One. What an amazing view!!! In the evenings, you may enjoy Disney's fireworks from your balcony or bedrooms!!! The unit is located in Tower One, where you find the lobby, concierge, restaurant, bar, lounge, fitness center, spa, and market an shop. It overlooks the Spring Pools just outside your building where three pools, splash pool, oversized hot tub and cabanas are awaiting you. You may park your car on the same level as your unit in the garage. The highlight of the resort is the Safari Waterpark. The FlowRider Double surf simulator can be challenging, but professionals help and teach you. Sunbathe while floating down the almost 700-foot lazy river. There are also the two-story, double slides, waiting for you. Everything you deserve as a place to relax and enjoy with your family and loved ones.

14501 Grove Resort Avenue Unit 1318, Winter Garden
8067 Glenlloyd Avenue, Winter Garden
$399,000
3 Beds ⋅ 3 Baths ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome home to this better-than-new townhome in Horizon West! Why pursue new construction when you can have UPDATES AND UPGRADES GALORE including a new primary bathroom barn door and shower, faucets and commodes in all bathrooms, carpet padding, soft-close cabinets, ceiling fans, hue lighting in the living room, and fresh touch-up paint inside and out. This townhome requires that you sacrifice nothing! The curb appeal is waiting to welcome you from the moment you pull up to the house. A massive covered front porch is ready for your morning coffee to be sipped and/or your evening beverage of choice. Step inside and forget that you are in a townhome as you take in the HUGE kitchen in the middle of the open concept downstairs living. Whether prepping meals, socializing, or landing an airplane, this kitchen island was made for enjoyment. This kitchen features stone countertops, loads of cabinetry, and stainless steel appliances all with a popular and tasteful color palette. A dining space on one side of the kitchen and a living room on the other, both lined with windows for natural lighting, make this space one to write home about. Head upstairs and find the primary suite on one side and the secondary bedrooms on the other. The primary bathroom has a brand new shower, dual vanity, and private water closet. You can even SEE DISNEY FIREWORKS from the bedroom and bathroom! The 2 remaining bedrooms share a bathroom that includes a shower/bathtub combination. Step out back to your private brick-paved courtyard ready for your outdoor enjoyment. The home and the 2-car garage are connected by an overhang across this courtyard for convenience and weather protection. This community is situated in the heart of Horizon West between Hamlin and Waterleigh for ample shopping and dining options, is super close to Disney, and right off of Highway 429 to bring you to all your favorite Central Florida destinations. Inquire today to make this gem your own!

8067 Glenlloyd Avenue, Winter Garden
5751 New Independence Parkway, Winter Garden
$399,000
2 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
Seller Motivated!! Well-maintained and thoughtfully updated, this New Independence townhome offers the perfect combination of style, comfort, and low-maintenance Florida living, all while located in a highly desirable community. Step inside to find updated flooring throughout, plantation shutters, and a bright, inviting layout designed for effortless everyday living. The renovated primary suite adds a modern, elevated touch, while the home’s thoughtful design provides the perfect setting for both relaxing and entertaining. Outside, discover a beautifully organized backyard oasis—a private space to enjoy your morning coffee, host friends, or simply take advantage of the Florida sunshine. And the lifestyle extends well beyond the property. New Independence offers an impressive collection of amenities, including two resident clubhouses, two resort-style pools with cabanas and grills, a whirlpool spa, two fitness centers, tennis and basketball courts, parks, playgrounds, and more than 6 miles of walking, running, and biking trails. Residents also have private lake access with boat ramps and on-lake ski ramps serving the lakes between Lake Hancock and Lake Speer. The community also features two dedicated dog parks, including separate areas for large and small dogs. Additionally, the HOA also includes basic high-speed internet and cable TV service, adding even more value to the community’s amenities package. Location is a major advantage; this home is only minutes from the popular Hamlin shopping and dining district, as well as the Winter Garden Village, downtown Winter Garden, and major roadways. Enjoy convenient access to some of the area’s best restaurants, shopping, and everyday necessities while still coming home to a peaceful, established community. Updated. Turnkey. Ideally located. And ready for its next owner.

5751 New Independence Parkway, Winter Garden
14501 Grove Resort Ave Unit 1622, Winter Garden
$399,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
BEST VIEW IN THE ENTIRE RESORT! AT A NEW PRICE! This is the largest condo offered at The Grove Resort & Waterpark, featuring a spacious 3-bedroom, 3-bath split floor plan designed for privacy and comfort, accommodating up to eight guests. Fully furnished and turnkey, this residence is ready for immediate personal use (Up to 179 Days Per Year), and rental income when you're not using it. The Grove Resort is a secluded private Florida enclave and one of Orlando’s premier vacation destinations, offering expansive accommodations and an exceptional array of onsite amenities and activities for all ages. Ideally located just three miles from the Western Way entrance to Walt Disney World® Resort, the property provides quick access to world-famous attractions while maintaining a peaceful resort atmosphere. Often described as “an escape within an escape,” The Grove serves as a gateway to the Disney experience and is conveniently close to all major Orlando theme parks and family attractions. Ownership is truly hands-free. The professional onsite management team handles all reservations, guest services, and maintenance, allowing owners to enjoy their condo at their convenience while generating income when not in use.

14501 Grove Resort Ave Unit 1622, Winter Garden
16306 Prairie School Drive, Winter Garden
$398,000
3 Beds ⋅ 3 Baths ⋅ Hawksmoor SubDv. ⋅ 34787 Zip Code
Priced to sell! Great location and highly desired community! Located in the highly sought-after Hawksmoor community in Winter Garden, this beautifully maintained townhome offers exceptional value and an incredible lifestyle. The location is unbeatable, close to top-rated schools, major highways, shopping, dining, and world-class theme parks. Situated just minutes from Hamlin, you’ll enjoy easy access to one of Central Florida’s most dynamic and fast-growing areas, with a wide variety of shopping, dining, and entertainment options, including Publix, Cinépolis Luxury Cinemas, and popular restaurants. Hawksmoor offers an impressive selection of top-tier amenities, including a resort-style zero-entry pool, splash pad, shaded pavilion, clubhouse with outdoor kitchen, fitness center, scenic walking trails, yoga lawn, and multiple playgrounds and parks. The community also provides quick access to the 429 expressway, making commutes to Downtown Orlando, Walt Disney World, and other major attractions convenient and easy. Priced to sell! Don’t miss the opportunity to own a townhome in one of Winter Garden’s most desirable communities. This is more than a home—it’s a lifestyle!

16306 Prairie School Drive, Winter Garden
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