Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, Florida—a picturesque gem nestled in the heart of Orange County. Known for its charming small-town atmosphere and vibrant community spirit, Winter Garden is a place where history meets modern living. Just a stone's throw away from the bustling city of Orlando, this delightful city offers residents the perfect blend of tranquility and accessibility.

Winter Garden boasts a rich history, which is beautifully reflected in its well-preserved downtown area. Stroll along Plant Street, lined with quaint boutiques, artisanal shops, and delightful eateries, where you can savor everything from gourmet coffee to farm-to-table cuisine. The historic Edgewater Hotel stands as a testament to the city’s heritage, inviting visitors to appreciate its unique character.

For outdoor enthusiasts, Winter Garden is a paradise. The West Orange Trail, a scenic 22-mile stretch, winds through lush landscapes, perfect for biking, jogging, or leisurely walks. With beautiful parks like the popular Newton Park and the serene Lake Apopka, residents can enjoy a variety of recreational activities, including fishing, picnicking, and bird-watching.

Families will find a welcoming community with excellent schools and a variety of family-friendly events throughout the year, including the popular Winter Garden Farmers Market. The city is also home to a thriving arts scene, with galleries and theaters showcasing local talent.

Whether you're looking to settle down or invest, Winter Garden presents an exceptional real estate opportunity. With its blend of charm, convenience, and community, this enchanting city is waiting for you to call it home. Come explore the magic of Winter Garden and discover your perfect place in Florida!

Newest Listings in Winter Garden

3 Beds ⋅ 2 Baths ⋅ Tuscany SubDv. ⋅ 34787 Zip Code

**GOLF CART COMMUNITY** Welcome to this charming home located at 1631 Charlemagne Ct in Winter Garden, FL. This beautiful house features three spacious bedrooms, a dedicated office, 2 full bathrooms, living room, dining room (currently using as a second office) laundry room and a two car garage, providing ample space for comfortable living. A beautifully maintained and thoughtfully upgraded home tucked away on a quiet cul-de-sac in one of Winter Garden's most desirable residential neighborhoods. Sitting on a large, fully fenced lot, this property delivers privacy, peace, and timeless appeal, with mature Oak trees providing lots of shade for outdoor entertaining. With a generous living area of 2,035 square feet, this home accords an inviting layout appropriate for relaxation and entertaining. Step inside and you're immediately greeted by cathedral ceilings in the living room and kitchen, creating an open, airy atmosphere filled with natural light. Tile flooring throughout the entire home adds a clean, cohesive look while offering durability and easy maintenance. The chef-inspired kitchen is the heart of the home, showcasing upgraded custom cabinetry, and granite countertops. The kitchen features abundant cabinet space and a large pantry offering exceptionally storage for all your kitchen essentials. Included are Bosch appliances and a charming nook overlooking the beautiful mature landscaping. The primary bedroom suite is a truly spacious sanctuary, complete with elegant plantation shutters, a Jacuzzi tub, dual sinks and his-and-her walk-in closets. Two additional bedrooms and a full bath provide comfort and flexibility for family or guests. The laundry room has built-in cabinetry, countertop and additional overhead shelf for added storage. A hall linen closet has extra-large storage providing plenty of space for additional household essentials. Major upgrades bring peace of mind and value including a new roof (2021), exterior freshly painted (2021), Brand-new AC (2024), Newly planted sod in back yard (2026) and upgraded Irrigation Control Panel (2026). Hop on your golf cart just minutes to historic downtown Winter Garden and enjoy your favorite restaurants, events and farmers market. Or take a relaxing nature walk or bike ride on the West Orange trial. This home is move in ready!

1631 Charlemagne Court, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code

Experience refined Florida living in this beautifully appointed 2024-built residence, ideally situated within the gated community of Del Webb Oasis. Thoughtfully designed with 2 bedrooms plus a versatile bonus room—perfect as a 3rd bedroom, private home office, den, or sitting room—the home offers a desirable split-bedroom floor plan that provides both privacy and comfort. upgrades are showcased throughout, including luxury vinyl flooring, recessed lighting, and contemporary finishes. At the heart of the home, the stylish kitchen features Tier 3 upgraded finishes complemented by Whirlpool appliances, creating an inviting space that seamlessly blends modern design with everyday functionality. Step outside to the screened-in lanai, an ideal setting for peaceful morning coffee, outdoor dining, or relaxing Florida evenings. The 2-car garage is equally well appointed with sleek epoxy flooring and an EV charger for added convenience. Beyond the home, Del Webb Oasis offers a gated, amenity-rich lifestyle designed for recreation, relaxation, and connection. Association fees include cable and internet, while the community provides an exceptional setting to stay active, socialize, and enjoy the best of Florida living. Adding to its appeal, the property is approximately 20 minutes from the Walt Disney World Resort area, depending on traffic—placing world-class dining, shopping, entertainment, and recreation within easy reach. Built in 2024 and beautifully upgraded throughout, this exceptional residence delivers the perfect combination of modern luxury, low-maintenance living, and resort-style convenience.

13418 Princess Street, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Orchard Pk/Stillwater Xing Ph SubDv. ⋅ 34787 Zip Code

WELCOME TO 3019 CHERRY ORCHARD LANE, A BEAUTIFULLY REMODELED HOME IN THE HEART OF WINTER GARDEN! This stunning residence has just undergone an impressive transformation, offering a fresh, modern, move-in-ready interior that truly stands out in the neighborhood. The home features NEW INTERIOR AND EXTERIOR PAINT (2026), a COMPLETELY RENOVATED KITCHEN, and BEAUTIFULLY UPDATED BATHROOMS, all thoughtfully redesigned with contemporary finishes and attention to detail. Custom-designed office with built-in cabinetry and a Murphy bed seamlessly integrated into the cabinetry. Every improvement was carefully selected to create a bright, stylish, and welcoming atmosphere throughout the home. This is a rare opportunity to own a beautifully renovated property offering a level of updates and finishes that is difficult to find in the surrounding area. Ideally located in desirable Winter Garden, with convenient access to shopping, dining, entertainment, parks, major roadways, and everything this highly sought-after area. MOVE-IN READY and beautifully refreshed from the inside out, schedule your private showing and come see what makes this home truly special!

3019 Cherry Orchard Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code

FULLY FURNISHED/TURNKEY LUXURIOUS 3/3 Corner Unit at The Grove Resort & Spa, Orlando Welcome to your dream oasis at The Grove Resort & Spa Orlando! This magnificent corner unit boasts the LARGEST floor plan available, featuring 3 spacious bedrooms and 3 elegant bathrooms. Experience the ultimate blend of comfort and luxury in this stunning condo-hotel located just six miles from Walt Disney World® Theme Parks, The Grove Resort & Spa offers unparalleled access to Orlando’s world-famous attractions. Enjoy daily transportation to Walt Disney World®, Universal Orlando, and SeaWorld, making it effortless to explore all that Orlando has to provide. Indulge in a variety of resort amenities designed for both relaxation and adventure. The Surfari Water Park features thrilling water slides, a lazy river, and the exhilarating FlowRider® Double surf simulator. Unwind at The Springs Pools, with three full-sized pools, an oversized hot tub, and poolside bar service. At Lake Austin, engage in catch-and-release fishing, paddle boating, or simply savor the serene views of the surrounding nature preserve. Stay active with a fully-equipped fitness center and scenic jogging paths. Families will love Flip Flop’s Family Fun Center, offering the latest arcade games and a glow-in-the-dark mini golf course. This corner unit is designed with a modern touch, offering a spacious open-plan living area, a gourmet kitchen, and stylish furnishings throughout. Each bedroom is a private retreat, complete with luxurious bedding and ample storage. Owning a unit at The Grove Resort & Spa offers not only a luxurious vacation spot but also a fantastic stress-free investment opportunity. Don’t miss the opportunity to own a piece of paradise at The Grove Resort & Spa, where every day feels like a vacation. Contact us today to schedule a private viewing and experience the exceptional lifestyle that awaits you.

14501 Grove Resort Avenue Unit 3201, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Orchard Hills Phase 2 SubDv. ⋅ 34787 Zip Code

Welcome to this bright and airy 4-bedroom, 2.5-bath home offering a comfortable and inviting layout. The spacious kitchen opens directly to the living room, creating a great flow for everyday living and entertaining, and features a large island with plenty of room for meal prep or gathering with family and friends. The open feel continues throughout the main living areas, with plenty of natural light adding to the welcoming atmosphere. The primary bedroom offers a private retreat with its own door leading to the balcony, providing a nice spot to step outside and enjoy the fresh air.

14354 Orchard Hills Boulevard, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome to the highly sought-after Brentwood model in the guard-gated golf community of Stoneybrook West! This 4-bedroom home offers a flexible floor plan with the option to use the fourth bedroom as a private home office, making it ideal for today’s lifestyle. The spacious kitchen opens to the family room, creating a comfortable gathering space highlighted by a cozy gas fireplace. Recent updates include a NEW HVAC system (2026), water heater (2023), roof (2018), new garbage disposal, gutters, and more. The primary suite features beautiful bay windows and a large walk-in closet. Enjoy Florida living year-round from the added covered and screened patio with tile flooring overlooking the fenced backyard. Additional highlights include attic storage with plywood flooring, providing valuable extra storage space. Located in the desirable Stoneybrook West community, residents enjoy an impressive array of amenities, including golf, clubhouse, pools, fitness facilities, tennis, pickleball, playgrounds, walking trails, and more. The community also offers lake access and boating for residents, including a private community boat launch. All of this is located in Winter Garden, one of Central Florida’s most sought-after and vibrant markets, offering convenient access to shopping, dining, entertainment, top-rated schools, major roadways, and everything the area has to offer. A flexible floor plan, important major-system updates, outdoor living space, and an exceptional guard-gated community make this Brentwood model a home worth seeing!

1118 Maidenmoor Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality. Sample Image

17732 Porter Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a versatile loft, providing additional living space or an ideal work-from-home area. With a two-car garage and laundry room conveniently located on the second floor, the Porter combines functionality with comfort, making it a standout home choice. Sample Image!!

17728 Porter Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code

Virtually Staged. **Virtually Staged | Tenant Occupied | Great Investment Opportunity** Beautiful two-story home in the desirable Storey Grove community in Winter Garden, currently rented for the full year—ideal for investors seeking immediate rental income. This home offers 3 bedrooms, 2.5 bathrooms, approximately 1,717 sq. ft. of living space, peaceful pond views, and a detached two-car garage. The open-concept layout features a kitchen with island overlooking the family and dining areas. Upstairs, the primary suite includes an oversized bathroom and walk-in closet. Residents enjoy a clubhouse, fitness center, resort-style pool, hedge maze, and dog park. Conveniently located near SR-429, US-192, and SR-545, just minutes from Walt Disney World, Orange County National Golf Center, shopping, dining, and Walmart. A great opportunity in one of Winter Garden’s most sought-after communities.

11367 Great Rock Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 2 SubDv. ⋅ 34787 Zip Code

Location, location, location!! Incredible opportunity to own a popular Whitman II model in the desirable Oakland Trails community with direct walkable access to the West Orange Trail! Imagine walking or biking to dinner in downtown Winter Garden just minutes away! You're also just minutes from the Florida Turnpike and all the new shopping in Clermont, including Costco just down the road. The location of this home is incredible! From the moment you step through the glass-paneled front door, you are greeted by a bright and airy two story foyer featuring warm luxury vinyl flooring and a contemporary staircase accented with sleek, industrial cable railings. The main level effortlessly transitions into a sun-drenched living space, anchored by large sliding glass doors that open up to an outdoor patio and frame views of the surrounding neighborhood. A neutral color palette and recessed lighting throughout enhance the sophisticated, move-in-ready aesthetic of the home. At the heart of the home is a chef-inspired gourmet kitchen designed for effortless entertaining. The massive central island takes center stage, featuring gleaming white quartz countertops, a deep undermount sink, and comfortable breakfast bar seating for four beneath stylish pendant lighting. Striking dark espresso cabinetry provides an abundance of storage space and beautifully contrasts the modern herringbone tile backsplash. Equipped with premium stainless steel appliances—including a built-in wall oven and microwave combo, a cooktop, and a French-door refrigerator—this kitchen is as functional as it is beautiful, complete with a spacious walk-in pantry nearby. Opposite the main living area, a formal dining space is defined by its soaring high-volume ceiling and a dramatic, modern halo chandelier that casts a warm glow over your dinner parties. Upstairs you'll love the oversized loft area that's open to below - perfect for cozier gatherings with the family. The secondary bedrooms are generously sized and each have their own walk in closets. The primary suite features a grand entrance with french doors leading to the large bedroom with two massive walk in closets, a tray ceiling, and more french doors leading to the spa inspired primary bath. The upstairs laundry room is conveniently placed to complete the home. With major shopping, dining, and entertainment options located within 15 minutes of this community, you have no shortage of lifestyle at your fingertips! You can get to Disney parks in about 20-25 minutes! You're also zoned to A rated schools, and have a very popular charter school - Oakland Avenue Charter School just minutes away. Come tour this home today!

2273 Standing Rock Circle, Oakland

3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code

Beautiful **3-bedroom, 2-bathroom condo at The Grove Resort & Water Park**, offered **fully furnished and turnkey**! Enjoy the perfect combination of comfort, resort-style living, and investment potential in the Orlando area. The unit features a spacious living area, fully equipped kitchen, TVs throughout, in-unit washer and dryer, and a private balcony. The Grove offers outstanding amenities including heated pools, hot tub, Surfari Water Park, lazy river, water slides, splash area, FlowRider, 24-hour fitness center, restaurant, bar & grill, arcade, mini golf, and Lake Austin access. Conveniently located near Disney and Orlando’s world-famous theme parks, with complimentary daily shuttle service to Disney parks. Ideal as a vacation home, second home, or investment property. Rental opportunities may be available through the resort program, subject to applicable rules and requirements. **Fully furnished, fantastic amenities, and an unbeatable Orlando vacation lifestyle!**

14501 Grove Resort Avenue Unit 2608, Winter Garden

6 Beds ⋅ 6 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to 907 Celadon, overlooking a broad conservation landscape with Lake Apopka views. Main home highlights include a first-floor primary suite, two substantial rooms off the foyer offering flexibility for two private offices, a guest suite or au pair suite, and a nearly 40-foot screened porch with new summer kitchen. A separate 907-square-foot carriage house apartment above the garage offers exceptional flexibility for multigenerational living, extended-stay guests or an in-law suite. Across the rear of the home, the kitchen, dining and living areas unfold as one expansive social space. The chef’s kitchen offers generous workspace for more than one cook, with extensive cabinetry throughout—including an entire wall of cabinetry—plus storage beneath the oversized island and seating for six. A long wall of sliding glass doors opens to the screened porch, extending the living space outdoors. Beyond it, the fully landscaped backyard offers generous green space with room to envision a future pool and pool house. Set apart from the main living spaces, the first-floor primary suite occupies its own wing at the rear of the home. A door from the kitchen closes the wing from the rest of the first floor, while the bedroom opens directly to the screened porch. An expansive dressing room—with extensive built-ins, a center island and chandelier—and a spacious primary bath complete the suite. Upstairs, three bedrooms and an oversized loft give younger family members a level of their own. The loft is currently arranged for movies, Xbox, play and a homework station, while the first floor remains where everyone comes together. Daily routines are easier here. Bright blue built-in lockers off the mudroom keep bags and shoes organized, while the large laundry room includes a dedicated dog wash station. Connected to the main residence by a covered breezeway, the carriage house includes a separate entrance, kitchenette, full bath and closet. Currently used as a private executive office, it offers flexibility for extended family or guests as needs change. Oakland Park’s golf-cart lifestyle is one of its signature advantages, and 907 Celadon has a dedicated golf-cart garage for it. Historic Downtown Winter Garden—Plant Street, the Farmers Market, dining and Crooked Can—is an easy cart ride from home. Direct access to the West Orange Trail offers 22 miles for walking, jogging and biking, plus community pools and green spaces.

907 Celadon Street, Winter Garden

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