Between $400,000 - $500,000 Winter Garden FL Real Estate, Homes, Condos for Sale

3 Beds ⋅ 3 Baths ⋅ O6381162 MLS ⋅ Toll Brothers BLDG.

Under Construction. Toll Brothers new construction in Horizon West, Winter Garden — estimated completion summer 2026. This Kellogg Townhome features a covered entry leading into an open and expansive living, L-shaped kitchen, and dining area. The home offers a spacious private courtyard with access to the detached two-car garage. The owner’s suite is highlighted by a large walk-in closet and a private bath with dual vanities and a separate shower.

13869 Easdale Alley, Winter Garden

$411,995

3 Beds ⋅ 3 Baths ⋅ O6379906 MLS ⋅ Toll Brothers BLDG.

Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. Our Crowley Townhome features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual vanities and separate shower.

13873 Easedale Alley, Winter Garden

$499,000

3 Beds ⋅ 2 Baths ⋅ O6375296 MLS

Welcome to this charming single-family residence in the highly desirable Black Lake Park community of Winter Garden. This well-maintained home features 4 (3 bedrooms + 1 study)and 2 full bathrooms with a functional open floor-plan that seamlessly connects living, dining, and kitchen areas — perfect for everyday living and entertaining. The spacious interior offers approximately 2,365 sq. ft. of living area on a ±8,178 sq. ft. lot with no rear neighbors and lush landscaping for added privacy. Situated in a vibrant community with amenities including tennis and basketball courts, playground, pool and outdoor recreation areas, this property is conveniently located minutes from Winter Garden Village dining and shopping, major roadways (including the 429), and top-rated schools.

14257 Lagoon Cove Lane, Winter Garden

$474,000

4 Beds ⋅ 2 Baths ⋅ O6369515 MLS

Under contract-accepting backup offers. Welcome to Stoneybrook West, a gated golf community located in the heart of Winter Garden. This single-story home sits on an oversized cul-de-sac lot and features 2,383 square feet of living space with a 4-bedroom, 2-bath split floor plan. Inside, the home offers open living and dining areas with high ceilings, along with a kitchen and family room combo that provides easy access to the covered lanai, great for everyday living and entertaining. The HOA includes 24-hour security, cable, internet, and a wide range of amenities such as a fitness center, tennis courts, community pool, volleyball and hockey courts, clubhouse, playground, and a community dock overlooking Lake Black. Conveniently located close to Winter Garden Village, top-rated schools, and major highways for easy commuting.

2609 Slagrove Court, Winter Garden

$500,000

R10962350 MLS

Vacant parcel (9.94 ac) with Residential/Agriculture zoning. Abundant foliage in a wetland setting. Obtaining permits is essential for assessing the conservation area before seeking a building permit. We highly recommend that prospective buyers engage the services of an environmental consultant to evaluate feasibility.

12995 Reaves Road, Winter Garden

$450,000

2 Beds ⋅ 2 Baths ⋅ R11079278 MLS

Luxury vacation home ownership 5 minutes from Walt Disney World Park. Dazzling new resort with waterpark, on-site restaurants andcafes, game room, fitness center, fitness trail, amazing pools, convention center, 20-acre activity lake, concierge and complimentary shuttle to the DisneyWorld parks. This unit boasts prime views to the waterpark.

14501 Grove Resort Avenue, Winter Garden

$449,000

3 Beds ⋅ 3 Baths ⋅ O6367905 MLS ⋅ 1 BLDG.

BEST VIEW IN THE ENTIRE RESORT! 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

$400,000

O6358096 MLS

Winter Garden 2 lots surrounded by commercial/industrial properties. Close to Highway 50, the Turnpike, and SR 429.

12325 & 12303 Stagg Road, Winter Garden

$460,000

3 Beds ⋅ 3 Baths ⋅ O6353080 MLS

Experience resort-style living and exceptional investment potential with this luxurious first floor condo located in The Grove Resort & Water Park, Orlando’s premier vacation destination. Ideally situated just 5 minutes from Walt Disney World, this fully furnished, turnkey residence offers a perfect combination of elegance, comfort, and convenience. Notice the Soaring Ceilings in this beautiful condo in every room. The sitting area in the primary bedroom sets the perfect ambiance. The spacious open-concept floor plan is filled with natural light and features modern décor, high-end finishes, and stylish furnishings throughout. The gourmet kitchen is equipped with stainless steel appliances, quartz countertops, and ample cabinetry, making it perfect for entertaining or extended stays. A full-sized washer and dryer provide added convenience. Residents and guests enjoy access to world-class amenities, including the Surfari Water Park with a FlowRider Surf Simulator, Lazy River, Water Slides, and Zero-entry Pools. Relax in multiple swimming pools and oversized hot tubs, or reserve a private cabana for the ultimate day of leisure. Additional amenities include a full-service spa, 24-hour fitness center, on-site dining at Valencia Restaurant, Longboard Bar & Grill, and Elements Bar & Lounge, plus the Flip Flop’s Family Fun Center. Outdoor enthusiasts can enjoy kayaking, fishing, and paddle boating on the 22-acre Lake Austin. A daily resort shuttle provides effortless access to Walt Disney World, Universal Studios, and SeaWorld, while nearby golf courses, shopping, dining, and major highways make The Grove Resort perfectly positioned for both relaxation and adventure. When not in use, owners can take advantage of the professionally managed hotel rental program, generating income while enjoying hassle-free ownership. With its prime location, full-service amenities, and strong rental potential, this condo at The Grove Resort & Water Park is an ideal vacation retreat and investment opportunity—all just minutes from Orlando’s most iconic attractions. The Grove Resort and Spa is zoned as a Condo/Hotel. Owners are allotted 179 days in a calendar year to stay on property.

14501 Grove Resort Avenue Unit 2101, Winter Garden

$435,000

4 Beds ⋅ 3 Baths ⋅ O6349881 MLS

Beautiful 4 bedrooms, 2.5 bathrooms, 2 car garage home located in the desirable Watermark community in Winter Garden. Home is perfectly located near the clubhouse (5min walk distance), all tile on the first floor and tray ceiling in the master suite. Watermark has resort-like amenities that includes a pool with splash pad, playground, club house, fitness center, tennis court and nearby attractions such as Orange County National Golf Center and Disney Golf courses. This house was built by Meritage Homes and is well-known for their energy-efficient features, that helps homeowners to live a healthier lifestyle while saving thousands of dollars on utility bills. Winter Garden's unique charm and ambiance offers a wide variety of entertainment, shopping, and dining experiences like the BRAND NEW "THE MARK" which brings Starbucks, 7Eleven, Advent Health, Walgreens and more just a walk distance from the house. A new High School (Horizon West High School) has been added to the zip code and a brand new Elementary School is being built, both within 2 miles from the house.

9338 Tyrella Pine Trail, Winter Garden

$497,000

4 Beds ⋅ 3 Baths ⋅ O6348822 MLS

PRICE IMPROVEMENT!!! Now offered at a substantially reduced price. The seller will pay off the existing solar panel loan (approximately $29,000) in full at closing, allowing the buyer to enjoy the benefits of solar energy without assuming this debt. Perfect for buyers seeking convenience, accessibility, and a family-friendly setting—just steps from the elementary school!! Discover this well-maintained 4-bedroom, 3-bath home located in the highly desirable Storey Grove community in Winter Garden. This property offers 2,042 sq ft of bright and functional living space/ Total area :4,704 SqFt , featuring an open-concept layout that seamlessly connects the kitchen and main living areas—ideal for everyday living and entertaining. The spacious primary suite includes a private bathroom and ample storage, while the additional bedrooms provide flexibility for guests, a home office, or growing families. Conveniently situated just steps from the elementary school, this home is perfect for those seeking accessibility and ease in their daily routine. Its location also provides quick access to main roads, shopping, dining, and Disney World, making commuting and errands simple and efficient. Enjoy outdoor living with a private patio, plus access to resort-style community amenities including a pool, fitness center, clubhouse, playgrounds, and dog parks. This property comes with solar panels, providing energy efficiency and savings.. Community parking regulations help maintain a clean and organized neighborhood environment, with guest parking available nearby. Seller is motivated and open to concessions. Schedule your private showing today.

16105 Water Spring Boulevard, Winter Garden

$419,000

3 Beds ⋅ 3 Baths ⋅ O6346155 MLS

This stunning and spacious townhome will exceed all expectations! Built in 2023 and designed with modern living in mind, this 3-bedroom, 2.5-bath home feels like a model property and offers the perfect blend of style, comfort, and investment potential. The first floor showcases an open-concept design with upgraded tile flooring, a beautifully appointed kitchen featuring solid-surface countertops, a massive island, stainless steel appliances, and seamless flow into the dining and living areas—ideal for entertaining or relaxing after a day at Orlando’s world-famous attractions. Step outside to your private retreat with an oversized brick-paver patio, fenced and enhanced with synthetic grass, creating a cozy and inviting outdoor space for family gatherings and guests to enjoy. The detached 2-car garage and extended driveway provide convenience and additional parking for owners and visitors alike. Upstairs, three generously sized bedrooms and two full bathrooms offer plenty of comfort and privacy, while the primary suite boasts an elegant en-suite bath with dual sinks and a spacious walk-in closet. Located in the highly desirable community of Storey Grove.

10540 Tribute Drive, Winter Garden

$419,000

3 Beds ⋅ 3 Baths ⋅ O6345956 MLS

This stunning and spacious townhome will exceed all expectations! Built in 2023 and designed with modern living in mind, this 3-bedroom, 2.5-bath home feels like a model property and offers the perfect blend of style, comfort, and investment potential. The first floor showcases an open-concept design with upgraded tile flooring, a beautifully appointed kitchen featuring solid-surface countertops, a massive island, stainless steel appliances, and seamless flow into the dining and living areas—ideal for entertaining or relaxing after a day at Orlando’s world-famous attractions. Step outside to your private retreat with an oversized brick-paver patio, fenced and enhanced with synthetic grass, creating a cozy and inviting outdoor space for family gatherings and guests to enjoy. The detached 2-car garage and extended driveway provide convenience and additional parking for owners and visitors alike. Upstairs, three generously sized bedrooms and two full bathrooms offer plenty of comfort and privacy, while the primary suite boasts an elegant en-suite bath with dual sinks and a spacious walk-in closet. Located in the highly desirable community of Storey Grove.

10534 Tribute Drive, Winter Garden

$479,900

3 Beds ⋅ 2 Baths ⋅ S5133690 MLS

Golf cart district * motivated seller * Beautiful single-story home is nestled in a serene cul-de-sac in the heart of downtown Winter Garden. It is just an 8-minute drive to downtown Winter Garden, 5 minutes away from Publix, 10 minutes to Walmart, 14 minutes to target in winter garden village, easy access to SR-429 and Florida turnpike, offering exceptional convenience. This cozy 3-bedroom, 2-bathroom and an office can be an easy 4th bedroom. Modern single-story home provides 2,035 square feet of comfort and style. Fully renovated in 2022, featuring no carpeting throughout with dual offices, the kitchen has been updated with refinished cabinets and stainless steel appliances. Additionally, the roof and air conditioning were replaced in 2020, making it an ideal choice for buyers seeking a quick-move-in home!

1672 Malcolm Pointe Drive, Winter Garden

$414,000

O6339284 MLS

Established boba tea business with high gross sales. Cash buyers only! NDA and proof of funds are required!

Winter Garden

$450,000

3 Beds ⋅ 3 Baths ⋅ O6320739 MLS

Short Sale. BACK ON THE MARKET — THROUGH NO FAULT OF THE SELLER! Buyer financing fell through. Welcome Home! 14536 Golden Harbor – a beautifully designed 3-bedroom, 2.5-bathroom home offering 1,904 square feet of thoughtfully laid-out living space. Nestled on the desirable Watermark community on the Disney side of Winter Garden, this Meritage Angelou II model combines modern efficiency with everyday comfort. The home comes equipped with fully PAID OFF solar panels, already wired and ready for connection—making this an energy-smart choice for eco-conscious buyers. As you walk in you are greeted with open-concept living/ dining room area that is ideal for entertaining, with a spacious kitchen located at the rear of the home. Enjoy stainless steel appliances, crown-topped cabinetry, a walk-in pantry, and a generous granite island that flows seamlessly into the living and dining areas. You’ll also find a built-in office nook and a convenient half-bath on this level. Upstairs, a spacious loft adds flexibility—perfect as a second living area, playroom, or home office. The laundry area is thoughtfully tucked away, and the split-bedroom design offers added privacy. The primary suite includes a walk-in closet, dual vanity, and a walk-in shower. Two additional bedrooms are located toward the front of the home and extend access to a private, covered balcony—an ideal spot to catch Disney’s nightly fireworks with a glass of wine and a great book. Whether you're unwinding on the front porch, enjoying balcony views, or taking advantage of community amenities—including a resort-style pool, playground, fitness center, basketball court, and more—you’ll find the lifestyle here hard to beat. You are just walking distance to The Mark, a versatile retail neighborhood center, with stores, restaurants, gas station, and more! Best of all, you’re just minutes from Walt Disney World, Magic Kingdom, Epcot, and Hollywood Studios—each less than 20 minutes away.

14536 Golden Harbor Lane, Winter Garden

$445,000

3 Beds ⋅ 3 Baths ⋅ S5124930 MLS ⋅ K Hovnanian Homes BLDG.

**Stunning Home in Winding Bay Preserve with Resort-Style Amenities** Discover your dream home in the sought-after Winding Bay Preserve! This immaculate residence offers resort-style living with a wealth of community amenities, including a sparkling pool, oversized cabana, tot lot, dog park, and fitness park—ensuring year-round fun for everyone. The home's open floor plan is bathed in natural light, creating a warm and inviting space that's perfect for entertaining. The kitchen is a chef's delight, featuring stainless-steel appliances, quartz countertops, and elegant light cabinetry. Conveniently located just 10 minutes south of the Hamlin area, you'll enjoy easy access to premier shopping, dining, and a state-of-the-art movie theater. Experience luxury, comfort, and convenience—all in one place!

11162 Hanlon Terrace Alley, Winter Garden

$400,000

O6244629 MLS

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

$415,000

3 Beds ⋅ 2 Baths ⋅ O6128999 MLS ⋅ Ii BLDG.

Luxury retreat at The Grove Resort & Water Park Orlando - spacious Jasmine floor plan! Escape to the magic of Orlando and indulge in the ultimate vacation experience at The Grove Resort & Water Park. This stunning 3-bedroom, 2-bathroom apartment, located on the fifth floor of Condominium II, offers an impressive 1,396 square feet of contemporary living space. As you step inside, you'll be greeted by an open and airy layout that seamlessly flows from the inviting living room to the elegant dining area and gourmet kitchen. The living room is adorned with a comfortable sleeper sofa. The modern kitchen is a chef's delight, complete with high-end appliances. Retreat to the lavish primary bedroom, which boasts a regal king-size bed, offering a serene haven for restful nights. The en-suite bathroom exudes sophistication and convenience, featuring modern fixtures and finishes. The guest rooms are thoughtfully designed and adorned with plush queen-size beds, ensuring a restful sleep for all your guests. The Grove Resort & Water Park is a paradise within itself, offering a plethora of world-class amenities.

14501 Grove Resort Avenue Unit 2541, Winter Garden

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Between $400K - $500K Winter Garden Real Estate

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