Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, Florida – a charming city that beautifully blends small-town warmth with modern amenities. Nestled in the heart of Orange County, Winter Garden is a vibrant community known for its rich history, picturesque landscapes, and a thriving downtown area that captivates residents and visitors alike.

Once a bustling center for citrus production, Winter Garden has transformed into a dynamic hub that celebrates its heritage while embracing contemporary living. Stroll down Plant Street, where you’ll find a delightful array of boutique shops, cozy cafes, and award-winning restaurants, all set against the backdrop of beautifully preserved historic buildings. The Winter Garden Farmers Market, held every Saturday, is a local favorite, showcasing fresh produce, artisanal goods, and a lively atmosphere that brings the community together.

Nature enthusiasts will appreciate the city’s stunning parks and recreational spaces. The West Orange Trail, a scenic 22-mile-long pathway, offers opportunities for biking, walking, and jogging, making it perfect for outdoor lovers. With its lush greenery and serene lakes, Winter Garden provides a tranquil escape just minutes away from the hustle and bustle of Orlando.

Families are drawn to Winter Garden for its excellent schools, friendly neighborhoods, and safe environment. The city hosts a variety of community events throughout the year, fostering connections among residents and creating a true sense of belonging.

Whether you’re considering a move or just visiting, Winter Garden is a place where you can enjoy the best of Florida living, with a perfect blend of charm, community spirit, and endless opportunities for adventure. Come discover all that Winter Garden has to offer!

Newest Listings in Winter Garden

17839 Gourd Neck Loop, Winter Garden
$925,000
7 Beds ⋅ 4 Baths ⋅ Verde Park Ph 2 SubDv. ⋅ 34787 Zip Code
Elegant pool residence in Winter Garden’s Verde Park, minutes from the Turnpike. This impeccably maintained 7-bedroom, 4-bath home offers 4,704 square feet of refined living space, a 3-car tandem garage, and a 0.24-acre lot with no community homes behind it. Multiple living and entertaining areas and a versatile floor plan offer exceptional flexibility for everyday living and hosting in a sought-after location. Step inside to a formal living room on one side of the entry and a formal dining room on the other. The living room is a flexible space that easily serves as a home office, library, sitting room, or whatever suits your lifestyle. At the heart of the home, the gourmet kitchen showcases quartz countertops, a tile backsplash, stainless steel appliances including a cooktop and double wall oven, crown-molded cabinetry with under-cabinet lighting, and a pantry. It opens to the family room, creating an inviting setting for daily living and entertaining. Tile flooring extends throughout the first floor, and a separate breakfast nook overlooks the pool. The downstairs primary suite is a private retreat with its own French doors to the pool area. The en suite bath features dual vanities, a soaking tub, a walk-in shower, and a generous walk-in closet with custom built-in organizers. An additional first-floor bedroom and adjacent full bath offer a comfortable option for guests, and the bath doubles as a convenient pool bath with direct access to the outdoors. Quartz countertops grace all four bathrooms. Upstairs, an expansive loft provides room for a second family room, game area, or gathering space. A separate media room with double doors is a dedicated space for movie nights, complete with a projection screen and projector that convey. Five additional bedrooms and two full bathrooms complete the second floor, with laminate flooring throughout the loft and bedrooms. Outside, your private backyard retreat features a sparkling 35x12 saltwater pool and a covered paver patio, designed to make the most of Florida living, whether you’re enjoying a quiet afternoon poolside or entertaining friends and family. The location is hard to beat. Just 5 minutes to Florida’s Turnpike, within walking or biking distance of the West Orange Trail, and minutes from shopping including Costco, dining, and Montverde Academy. With its thoughtfully designed floor plan, multiple entertaining areas, and convenient location, this exceptional home is ready to welcome its next owners. Schedule your private showing today.

17839 Gourd Neck Loop, Winter Garden
2107 Gopher Tortoise Terrace, Oakland
$364,900
2 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Beautifully maintained fully furnished six-year-old townhome in the charming town of Oakland! This 2-bedroom, 2.5-bath home features a covered front porch, abundant natural light, and thoughtful upgrades throughout. The open great room welcomes you with Shaw luxury vinyl tile flooring, neutral colors, recessed LED lighting, and dual-pane Low-E windows with cordless faux wood blinds. The kitchen features 42-inch cabinetry, granite countertops, a gray subway tile backsplash, and a spacious island with upgraded pendant lighting and a large undermount sink. Appliances include a Whirlpool Gold microwave, range, and dishwasher, plus an LG French-door refrigerator. A generous pantry with a California Closets shelving system provides exceptional organization. The adjoining dining area features upgraded lighting and access to a private 19-by-15-foot paver courtyard through a full-glass door with built-in blinds. A convenient desk nook with granite countertops, drawers, and cabinetry offers space to work from home. The first-floor laundry room includes a California Closets laundry station and access to ample storage beneath the stairs. A half bath is conveniently located off the stair landing. Upstairs, both spacious bedrooms feature walk-in closets and private bathrooms. The primary suite offers a beautifully organized California Closets system with a built-in vanity. Its ensuite bath includes dual sinks, granite countertops, Moen faucets, a private water closet, and a tiled shower with decorative accents, frameless glass, and an upgraded showerhead. The second bedroom’s bathroom features granite countertops and a tiled tub/shower combination with an accent inlay. The private courtyard connects to a two-car garage with epoxy flooring and a Bluetooth-enabled opener. Additional features include gutters, a Taexx built-in pest control system, Nest thermostat, Ring security system and doorbell, Alexa-compatible front porch lighting, and prewiring for ceiling fans in the great room and bedrooms. Enjoy community walking paths, a playground, and a pool, with lawn care included in the HOA. Conveniently located near the West Orange Trail, downtown Winter Garden, downtown Clermont, Florida’s Turnpike, and Winter Garden Village. Bring your pups—this community has no dog breed restrictions!

2107 Gopher Tortoise Terrace, Oakland
14807 Winter Stay Drive, Winter Garden
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code
Welcome to 14807 Winter Stay Drive, a beautifully upgraded luxury residence located in the heart of Horizon West in Winter Garden. Spanning 3,856 square feet of refined living space on an oversized lot, this 5-bedroom, 4-bathroom home combines upscale comfort, privacy, and resort-style living. The outdoor sanctuary is custom-built for the Florida lifestyle, featuring a fully fenced backyard, a heated saltwater pool and spa, a spacious covered lanai with retractable awnings, and scenic sunset views overlooking the prestigious Orange County National Golf Course. Inside, the open-concept layout flows effortlessly for everyday living and grand entertaining. The gourmet kitchen boasts premium appliances, upgraded finishes, and an expansive quartz center island. The primary suite offers a private retreat with a spa-inspired bathroom, complemented by custom closets and a dedicated drop zone for extra organization. Upstairs, a large bonus room provides flexible space for a home theater, media room, or executive office, while an oversized 3-car garage offers generous vehicle and storage space. Value-adding upgrades include an owned solar panel system to significantly reduce energy costs. Situated just 0.5 miles from The Mark Plaza and minutes from Horizon West Hospital, top-rated dining, and shopping, this home offers fast access to SR 429, Florida’s Turnpike, and Walt Disney World. Schedule your private tour today.

14807 Winter Stay Drive, Winter Garden
14825 Porter Road, Winter Garden
$609,998
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Phase 2a And 2b SubDv. ⋅ 34787 Zip Code
Virtually Staged. With 2,732 square feet, a spacious upstairs loft and a downstairs room ready to serve as a fourth bedroom, this Summerlake home gives you room to arrange life as you please. Three bedrooms and 2.5 baths. The open main floor has tile underfoot, plantation shutters and a stone accent wall in the living room. The kitchen offers a granite island with seating, dark wood cabinetry, tile backsplash, gas range and pendant lighting, and opens to the dining area. Sliders lead to a covered paver patio and a fenced backyard with a fire pit. Upstairs, the primary suite has a custom-fitted walk-in closet, double vanity, soaking tub and glass-enclosed shower. Stone-trimmed covered front porch, & a rear-entry garage. Summerlake amenities include a resort-style pool with splash pad, lakefront clubhouse, fitness center, tennis and basketball courts, playgrounds, dog park, fishing pier and walking trails. This home is conveniently located close to the amenities. Close to Hamlin Town Center, SR 429 and a short drive to the Parks.

14825 Porter Road, Winter Garden
7186 Wild Strawberry Run, Winter Garden
$750,000
4 Beds ⋅ 4 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully designed 4-bedroom, 3.5-bathroom home in the highly desirable Independence community of Winter Garden! Offering a thoughtful blend of space, comfort, and lifestyle, this home features an additional private office, a spacious bonus room, and a unique layout designed for both everyday living and entertaining. Step inside to discover generous living spaces, a modern kitchen perfect for gathering with family and friends, and a spacious primary suite designed for comfort and relaxation. The additional office provides an ideal space for working from home, while the large bonus room offers endless possibilities—a media room, game room, or second family lounge. The home features a convenient half-bath on the first floor, a Jack-and-Jill bathroom, and a detached garage located at the rear of the property, adding character and functionality to the home's layout. Outside, enjoy a nicely sized backyard with room to create your own private outdoor retreat, including the potential to add a pool (subject to applicable approvals). Whether you envision weekend barbecues, outdoor entertaining, or simply relaxing in your own space, the possibilities are yours to explore. What truly makes this location special is the lifestyle waiting right outside your door!Horizon West, offering amenities and outdoor spaces designed to bring recreation, relaxation, and community connection together. Residents can enjoy: Community swimming pools for cooling off and enjoying the Florida sunshine Clubhouses and fitness centers for recreation and wellness Scenic walking and biking trails for outdoor exercise Community parks and playgrounds for outdoor fun Sports courts and beautifully maintained green spaces for an active lifestyle The location is equally appealing, with convenient access to shopping, restaurants, cafés, schools, and everyday essentials. Explore nearby Hamlin and Winter Garden Village for additional dining, shopping, and entertainment options. And when it's time for adventure, Walt Disney World and Central Florida's world-famous attractions are within driving distance, making weekend outings and family fun easy to enjoy. Whether you're looking for room to grow, space to work from home, or a community that offers amenities beyond your front door, this home presents an opportunity to enjoy the best of the Winter Garden lifestyle. Enjoy the space. Embrace the community. Make Winter Garden home.

7186 Wild Strawberry Run, Winter Garden
10079 Austrina Oak Loop, Winter Garden
$880,000
5 Beds ⋅ 4 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Enjoy spacious living, no rear neighbors, and Disney fireworks views in the sought-after Watermark community of Winter Garden! Built by Meritage Homes, this Maison floor plan offers 5 bedrooms, 3.5 bathrooms, and approximately 3,359 square feet of thoughtfully designed living space. A paver driveway and covered front porch create a welcoming first impression, leading into a foyer that opens to the second floor. The main level features a separate dining room and an open kitchen with a center island, pantry, and butler’s pantry. The kitchen connects seamlessly to the spacious family room, creating an inviting setting for everyday living and entertaining. A downstairs bedroom provides flexibility for guests or a home office, with a half bathroom conveniently nearby. Step outside to the covered lanai and enjoy the added privacy of having no rear neighbors, along with views of Disney fireworks. Upstairs, the spacious primary suite features two walk-in closets and an ensuite bathroom with dual vanities, a soaking tub, and a separate shower. Three additional bedrooms and two full bathrooms provide ample space, while the game room offers a versatile area for movies, hobbies, or relaxation. An upstairs laundry room adds everyday convenience, and the two-car garage provides parking and storage. Watermark offers an exceptional collection of resort-style amenities, including a swimming pool with a splash pad, clubhouse, fitness center, tennis courts, playground, park, and outdoor amphitheater. The community’s second-story viewing deck provides another inviting spot to enjoy Disney fireworks. Located in Winter Garden’s desirable Horizon West area near sought-after schools, this home offers convenient access to Hamlin’s shopping, dining, and entertainment, Walt Disney World, and SR-429. Discover a home that brings together generous living space, a versatile floor plan, and outstanding community amenities. Schedule your private showing today!

10079 Austrina Oak Loop, Winter Garden
17126 Quicksilver Avenue, Winter Garden
$525,000
4 Beds ⋅ 3 Baths ⋅ Waterside On Johns Lake - Phase 2c SubDv. ⋅ 34787 Zip Code
Welcome home to this beautifully cared-for 4-bedroom, 3-bathroom home in the welcoming Waterside community! Built in 2022, the thoughtfully designed floor plan, spacious backyard, and wonderful neighborhood amenities combine to create the perfect blend of comfort, functionality, and everyday family living. Inside, the OPEN-CONCEPT living space flows effortlessly into the kitchen, creating a comfortable gathering place for family time, entertaining, and everything in between. The kitchen features beautiful Silestone QUARTZ COUNTERTOPS, stylish gray cabinetry, and stainless steel appliances. The spacious primary suite offers a HUGE WALK-IN CLOSET, while the primary bathroom features a double-sink vanity and large WALK-IN TILED SHOWER. A bedroom conveniently located downstairs adds incredible flexibility and can easily serve as a guest room, home office, playroom, or a space for visiting family and friends. Throughout the home, you'll find thoughtful upgrades including plantation shutters, built-in features, 9-foot ceilings, and a beautiful wrought-iron stair railing. Situated on an OVERSIZED CORNER LOT, the property features a large fenced-in backyard with plenty of room to play, relax, or gather with friends. The back paver patio is perfect for weekend barbecues and outdoor entertaining, while the covered front porch provides a welcoming spot to enjoy your morning coffee or unwind at the end of the day. Waterside Residents enjoy access to a community clubhouse, pool, fitness center, playgrounds, park, and a dock on Johns Lake. With seasonal community events and monthly food truck nights, there are plenty of opportunities to get to know your neighbors and enjoy everything the community has to offer. Conveniently located near Downtown Winter Garden, Hamlin, and Walt Disney World, you'll be close to a fantastic selection of restaurants, shops, and entertainment. Easy access to FL-429 and the Florida Turnpike makes commuting and exploring Central Florida a breeze. Come see why this home and community are such a wonderful place to put down roots, make memories, and call home!

17126 Quicksilver Avenue, Winter Garden
11815 Shine View Lane, Winter Garden
$853,626
5 Beds ⋅ 5 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Located off the family room is a den with French doors perfect for work or play and a powder room. Customize this area to meet your needs with an optional bedroom and full bathroom. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11815 Shine View Lane, Winter Garden
14501 Grove Resort Avenue Unit 3631, Winter Garden
$164,900
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
This stunning 2-bedroom, 2-bathroom condo-hotel in Orlando, Florida, offers the perfect blend of luxury, comfort, and convenience. Located just minutes from the world-famous theme parks, this fully furnished unit is an excellent choice for both personal use and investment. The condo features a spacious open floor plan with modern finishes, a fully equipped kitchen with stainless steel appliances, and a private balcony with breathtaking views. The master suite boasts a luxurious en-suite bathroom, while the second bedroom and bath provide ample space for guests. Enjoy resort-style amenities, including a sparkling swimming pool, fitness center, full-service spa, on-site dining, concierge services, and a shuttle to major attractions. With its prime location near shopping, dining, and entertainment, this condo-hotel is an exceptional opportunity for those looking to experience the best of Orlando!

14501 Grove Resort Avenue Unit 3631, Winter Garden
11079 Sound Shore Drive, Winter Garden
$825,000
5 Beds ⋅ 5 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Welcome to your dream home that checks ALL the boxes! This 2023 built block on block construction popular Torrey floor plan has everything you will need with 5 bedrooms, 4 and a half baths, SOLAR panels included in sale price, a formal dining room, DOWNSTAIRS guest room with attached full bathroom, large lanai, bonus room to create a second living area or playroom, gourmet kitchen, and fenced in yard with no direct rear neighbor. This home is perfect for entertaining, having an open concept layout with a kitchen/living open space, while also boasting classic charm with a formal dining room off the kitchen. The stunning kitchen features a built in wall oven and microwave, cooktop with matching stainless steel hood, and large butler’s pantry. The formal dining room could be used for it’s intended purpose or it can easily be closed in with French doors to create a home office, playroom, formal sitting room, or exercise room! Upstairs you will find the remaining 4 bedrooms, 3 full bathrooms, and huge bonus room. The master retreat is true luxury with a soaking tub and fireworks view from the master bedroom! Currently, the downstairs guest room is being used as a dual purpose room with a desk to be used as an office but also has a custom, built in murphy bed that can be used when you have guests in town. This home features a huge 28x10 covered lanai perfect for dining a la fresca and enjoying the peaceful dry retention pond that this home backs up to that is fleeting with wildlife including many different bird species, hawks, and sand cranes. The spacious, fenced in yard is perfect for your furry friends or children. Located in the sought after Horizon West area zoned for “A” schools including Atwater Bay Elementary, Water Spring Middle School, and Horizon West High. Along with its amazing location, the Waterleigh community also offers a beautiful clubhouse with resort style pool, miniature golf course, beach volleyball, grills, picnic areas, fishing pier on the lake, biking trails, walking trails, tennis courts, pickleball, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. The clubhouse has a robust calendar of events for all ages such as Mahjong classes, exercise classes, kids dance lessons, beer tasting events, and many more! Living in the gorgeous Waterleigh community surrounded by ponds and lakes is all about nature and outdoor living! Love the outdoors but don't like mowing the lawn and weeding the shrubs? No problem, the HOA takes care of that for you here. Love the Florida golf cart life? You can take your street legal golf to the community pool, and join the neighbors for lots of fun, holiday golf cart parades!! Within minutes you have loads of shopping and activities including Hamlin center, Flamingo Crossings shopping center, and Disney parks and resorts! All you have to do is move in and start enjoying the lifestyle Waterleigh has to offer! Lastly, this well loved house has all the upgrades including: solar panels (sellers will pay off the remaining loan balance at closing), telsa EV charger, motorized blinds in all 4 bedrooms upstairs, (2) alarm.com security systems, 3 ring cameras, 2 garage ceiling storage racks, and built in attachments in the garage for a kids ninja warrior style obstacle course. Green aspects: solar panels and reclaimed water for watering the grass.

11079 Sound Shore Drive, Winter Garden
14037 Pecan Orchard Drive, Winter Garden
$819,000
5 Beds ⋅ 5 Baths ⋅ Orchard Pk/Stillwater Xing Ph SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully upgraded 5-bedroom, 4.5-bath home in Orchard Park, offering 3,793 square feet of thoughtfully designed living space and an extensive renovation completed in late 2024. Recent improvements include all new appliances, luxury vinyl plank flooring throughout with no carpet, fresh interior paint, new laundry room cabinetry and granite countertop, plus the addition of a 5th bedroom and 4th full bathroom, completed with permits. The spacious, open floor plan is ideal for both everyday living and entertaining. Plantation shutters throughout the home, and a first-floor guest suite with private ensuite bath provides an ideal space for guests or multigenerational living. The open kitchen features granite countertops, an oversized island, abundant cabinetry, and a walk-in pantry, with plenty of space for preparing meals and gathering with family and friends. Upstairs, the expansive owner’s suite features a luxurious bath and an impressive 8' x 14' walk-in closet. Two generously sized bedrooms, each with its own walk-in closet, share a hall bath with double sinks, while the fifth bedroom features its own ensuite bath. A spacious second-floor loft and conveniently located upstairs laundry room complete the upper level, providing exceptional flexibility for a home office, media room, playroom, or additional gathering space. Outdoor living is equally inviting, with a welcoming front porch, fully fenced backyard, and covered rear patio with extended pavers—perfect for relaxing, entertaining, or enjoying the Florida sunshine. An attached 2-car garage provides additional convenience and storage. HOA fees include landscaping, allowing you to enjoy a beautifully maintained yard without the work. Buyer and buyer’s agent are responsible for verifying room dimensions, HOA information, community rules, lease restrictions, and other information deemed important to the buyer.

14037 Pecan Orchard Drive, Winter Garden
14031 Zephermoor Lane, Winter Garden
$800,000
5 Beds ⋅ 3 Baths ⋅ Windward Cay 48 125 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Beautifully renovated 5-bedroom, 3-bath pool home located in gated Windward Cay! This move-in-ready 3,007 sq. ft. home has been thoughtfully updated with high-end finishes throughout, including a renovated kitchen and bathrooms and new luxury vinyl flooring. All major mechanicals have been updated, including the roof (2023), both AC units (2024 and 2026), and water heater (2025). When you enter the home, you are greeted by a gorgeous open space with views straight to the pool through a wall of oversized glass sliding doors. To the left and right, you have bonus spaces that can be used as an office, gaming area, or hangout space. To the right is a large dining room, flooded with natural light. At the foot of the staircase, there is a large storage space that is currently being used as a fun play area to spark imagination. Beyond the dining room is the open family room and renovated kitchen, featuring new hardwood cabinets, quartz countertops, plenty of storage, and a large island that keeps you connected to your guests while you watch the big game! Just beyond the family room, you'll find a large bedroom with a Murphy bed and great storage, next to a full bath, giving guests their own private space and access to the pool area! Upstairs, we have the remaining four bedrooms. The carpet, hallways, and stair spindles are all brand new. The spacious primary suite features a spa-like ensuite with a soaking tub and luxurious walk-in shower, along with two large closets and luxury vinyl flooring. Oversized windows bring in excellent natural light, while the high ceilings, crown molding, and tray ceilings add to the home's open and inviting feel. The other bedrooms are spacious and bright, with a large renovated bathroom featuring dual sinks and new finishes. Outside, enjoy the Florida lifestyle with a screened-in heated salt water pool and spa, perfect for relaxing or entertaining. The home also offers a 3-car garage and sits on approximately a quarter-acre lot. This home also features a water softener and central vacuum. Located in the gated community of Windward Cay, this home is close to Winter Garden's shopping, dining, entertainment, and major roadways

14031 Zephermoor Lane, Winter Garden
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