Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, a charming city located in the heart of Florida! Known for its rich history, vibrant community, and beautiful landscapes, Winter Garden offers the perfect blend of small-town charm and modern amenities.

Nestled in the sunshine state of Florida, Winter Garden boasts a prime location with easy access to major attractions, world-class entertainment, and stunning natural beauty. Residents here enjoy a laid-back lifestyle with a variety of outdoor activities, including hiking, biking, and watersports, thanks to the city's proximity to pristine lakes and lush parks.

In Winter Garden, you'll find a thriving downtown area filled with unique shops, delicious restaurants, and exciting events year-round. The city's historic architecture and picturesque streets make it a popular destination for visitors and a beloved home for residents.

With top-rated schools, safe neighborhoods, and a strong sense of community, Winter Garden is the perfect place to settle down and enjoy all that Florida has to offer. Whether you're looking for a cozy bungalow, a spacious family home, or a luxury estate, Winter Garden has a diverse range of real estate options to suit every lifestyle.

Come and experience the magic of Winter Garden – where small-town charm meets big-city convenience in the Sunshine State!

Newest Listings in Winter Garden

665 Canopy Estates Drive, Winter Garden
$1,499,900
5 Beds ⋅ 5 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
Virtually Staged. EXCEPTIONAL LUXURY IN THE HEART OF WINTER GARDEN! Welcome to this stunning 5-bedroom, 4.5-bathroom pool home nestled within Canopy Oaks, an exclusive, Parade of Homes award-winning gated community featuring just 49 residences. This beautifully upgraded Lockhart II model delivers an exceptional blend of elegance, comfort, and sophistication, featuring TWO luxurious primary suites, one on each floor, a 3-car garage, and private front and rear balconies. Step through the magnificent arched double doors into a breathtaking two-story foyer, where timeless architectural details and modern finishes set the tone. The thoughtfully designed interior showcases a versatile office or flex space, an exquisite wine cellar with authentic Chicago brick flooring, and a gourmet kitchen featuring a 5-burner natural gas cooktop and oversized island. A beautiful wooden staircase with custom forged-iron railings leads upstairs to generously sized bedrooms, a spacious primary suite with an impressive walk-in closet, and a dedicated home theater complete with a movie projector. RECENT UPGRADES includes 2025 A/C system, contemporary light fixtures, updated countertops, fresh interior paint, new downstairs flooring, custom closets, and a beautifully remodeled backyard. Step outside into your private retreat, featuring a sparkling pool and an inviting setting for entertaining or unwinding. LOCATION IS EVERYTHING! Just minutes from Winter Garden Village and Historic Downtown Winter Garden, enjoy convenient access to premier shopping, exceptional dining, and entertainment. With easy connections to Florida’s Turnpike, SR 429, SR 408, and Highway 50, the best of Central Florida is within easy reach. Luxury, exclusivity, and an unbeatable location come together in one extraordinary home. Schedule your private showing today!

665 Canopy Estates Drive, Winter Garden
8154 Common Teal Court, Winter Garden
$645,000
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 4b SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to 8154 Common Teal Court, a beautiful home in Winter Garden’s sought-after Summerlake community, where comfortable living and thoughtful design come together. Built in 2019, this single-story residence offers 4 bedrooms, 3 bathrooms, and 2,281 square feet of living space, with a collection of upgrades selected from the very beginning. The open floor plan connects the main living areas, creating a bright, welcoming space that feels just as comfortable for everyday living as it does for entertaining. The kitchen is a standout, featuring upgraded luxury cabinetry and finishes that bring a refined touch to the heart of the home. A spacious primary suite and well-appointed additional bedrooms complete the interior. Outside is where this home takes on a character of its own. Added after construction, the expansive custom deck extends beyond the covered lanai, offering plenty of room to entertain, dine outdoors, or simply unwind. And the sunsets? They're something special. With beautiful sunset views right from the deck, it's easy to imagine this becoming a favorite spot to end the day. The property also features a NEW roof (2025), and solar panels, which will be paid off by the seller at closing. Summerlake is known for its inviting neighborhood atmosphere and community amenities, including a resort-style pool, fitness center, parks, and recreational spaces. Just minutes away, the Hamlin district offers a growing collection of restaurants, shops, entertainment, and everyday conveniences. Downtown Winter Garden, major roadways, and Orlando's attractions are also within easy reach. Between the upgraded interiors, the outdoor living space, and those beautiful evening views, 8154 Common Teal Court has a lot to offer in one of Winter Garden's most desirable locations.

8154 Common Teal Court, Winter Garden
Winter Garden
$239,900
3 Beds ⋅ 1 Baths ⋅ Bay St Park SubDv. ⋅ 34787 Zip Code
Welcome to Winter Garden! This charming 3-bedroom home offers 815 square feet of comfortable living space and is full of updates. The beautifully renovated kitchen features shaker cabinetry, granite countertops, and a stylish stacked stone backsplash. Fresh interior and exterior paint give the home a clean, refreshed feel. TILE THROUGHOUT! NO CARPET! The roof was replaced in 2023, offering added peace of mind. A one-car carport provides convenient covered parking. Enjoy the freedom of NO HOA and a convenient location just a short stroll to Zanders Park & minutes from Plant Street and historic downtown Winter Garden, with its popular restaurants, shopping, entertainment, farmers market, and West Orange Trail. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this home is worth a look! Do not miss this opportunity, schedule your private tour today!!!

Winter Garden
159 9th Street, Winter Garden
$369,900
3 Beds ⋅ 2 Baths ⋅ Loveless J S Add 01 SubDv. ⋅ 34787 Zip Code
Enjoy the best of Winter Garden living in this beautifully built 2024 home! This property features 3 bedrooms, 2 bathrooms, with 1,188 square feet of thoughtfully designed living space. The home features an open-concept floor plan that creates a bright and welcoming atmosphere with LPV throughout. The spacious kitchen is the heart of the home, showcasing a large island, shaker cabinetry, granite countertops, and stainless steel appliances. The primary suite has a spa-like feel with en-suite bathroom and walk-in closet. Enjoy the convenience of a one-car garage and a covered patio, perfect for relaxing outdoors. NO HOA! Ideally located near all that downtown Winter Garden has to offer, including shopping, dining, entertainment, and the popular West Orange Trail. Modern construction, a convenient location, and the freedom of no HOA make this home one you won't want to miss!

159 9th Street, Winter Garden
14347 Braemar Street, Winter Garden
$493,000
4 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code
Built in 2024 by Meritage Homes, this pristine 4-bedroom, 2.5-bathroom bungalow in Horizon West’s Highland Ridge delivers energy-efficient modern living at its finest. The open-concept first floor boasts high ceilings, durable tile flooring, and a chef’s kitchen equipped with a large prep island, solid-surface counters, 42” cabinetry, and stainless steel appliances. All 4 bedrooms and the laundry room are conveniently located upstairs, headlined by a primary retreat with an oversized walk-in closet and dual-sink ensuite bath. Built with advanced spray-foam insulation, high-performance windows, and smart features for peak comfort and utility savings. Enjoy community pool access, cabana, and tot lot, with immediate proximity to SR-429, Flamingo Crossings shopping and dining, top-rated schools, and Walt Disney World.

14347 Braemar Street, Winter Garden
10067 Austrina Oak Loop, Winter Garden
$1,150,000
6 Beds ⋅ 5 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Welcome home this beautifully renovated 6-bedroom, 5-bathroom home offering 4,305 sq. ft. of stylish living in a desirable Winter Garden community. Features include elegant first-floor porcelain tile, an updated kitchen with quartz countertops, a smart cooktop, and decorative glass cabinetry. The spacious primary suite boasts a custom-built walk-in closet. Enjoy Florida living in the outdoor oasis featuring a gazebo and built-in fire pit seating area. A three-car split garage provides ample parking and storage. Residents enjoy two community pools and a playground. Freshly updated and move-in ready, this exceptional home offers comfort, style, and space for the whole family!

10067 Austrina Oak Loop, Winter Garden
8877 Lakeshore Pointe Drive, Winter Garden
$650,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this stunning, completely remodeled home in beautiful Winter Garden! Offering 4 spacious bedrooms, 3.5 luxurious bathrooms, and a separate guest house. This exceptional property combines elegance, comfort, and versatility. The home features a gorgeous interior courtyard, creating a beautiful private setting perfect for relaxing or entertaining. Inside, you’ll find soaring ceilings throughout, an elegant and inviting living space, and a chef-inspired kitchen equipped with state-of-the-art appliances and exquisite finishes. The spacious bedrooms include comfort and privacy, while the luxurious primary suite features a spa-inspired bathroom with a beautiful soaking tub, an elegant walk-in shower, and generous closet space. Every detail has been thoughtfully designed to create an elegant yet welcoming atmosphere. With its complete renovation, stunning architectural features, private courtyard, and separate guest residence, this extraordinary Winter Garden home offers a truly special living experience.

8877 Lakeshore Pointe Drive, Winter Garden
8900 Sonoma Coast Drive, Winter Garden
$745,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Enjoy resort-style living in Waterleigh, a master-planned community in Horizon West, Winter Garden. This single-story home offers 3 bedrooms, 2 full bathrooms, a half bathroom, and a separate office, complemented by distinctive interior finishes and expansive outdoor living spaces. An inviting foyer features decorative wood slat accents, integrated lighting, and a floating bench. The open-concept living area showcases a tray ceiling, wood-look tile flooring, and a custom TV feature wall with a floating media console. The kitchen features cabinetry, stone countertops, a tile backsplash, pendant lighting, and a stainless steel appliance package, including a refrigerator, built-in oven, microwave, cooktop, and dishwasher. A separate dining area provides additional gathering space. The office features glass French doors, built-in cabinetry, shelving, and work surfaces. The primary suite includes custom closet organizers and an en-suite bathroom with dual sinks, illuminated mirrors, a separate shower, a soaking tub, and a private water closet. The laundry room includes a washer and dryer, while the garage offers extensive storage cabinetry and a coated floor. Step outside to a covered, screened lanai overlooking an expansive paver patio with a fire pit, fenced backyard, and wooded backdrop—an inviting setting for relaxing or entertaining. Waterleigh offers community pools, clubhouses, fitness facilities, playgrounds, and recreational amenities in a scenic setting of lakes and ponds. Enjoy convenient access to shopping and dining at nearby Hamlin, Publix within the community, historic Downtown Winter Garden, and SR-429. Nearby schools include Atwater Bay Elementary, Water Spring Middle, and Horizon High School; buyers should verify current school assignments with Orange County Public Schools. Kitchen appliances, washer, and dryer are included in the sale. Furnishings shown in the photographs are actual furnishings. Select photographs have been digitally enhanced for lighting, and flames have been digitally added to the outdoor fire pit.

8900 Sonoma Coast Drive, Winter Garden
480 W Plant Street, Winter Garden
$785,000
2 Beds ⋅ 3 Baths ⋅ Park Place/Winter Garden SubDv. ⋅ 34787 Zip Code
In the heart of Historic Downtown Winter Garden, this three-story townhome in Park Place offers a rare blend of architectural character, flexible living spaces, and an exceptional walkable lifestyle. Step inside and discover this well-executed floor plan that lives much larger than its square footage suggests. Soaring 20-foot ceilings, expansive windows, open stair railings, and a custom loft create an impressive sense of space and natural light with an airy feel. The second-floor living area is the centerpiece anchoring the home, featuring custom German Schmear limewashed brick, detailed trim work, a built-in entertainment center, and sliding glass doors that open to a Juliet balcony overlooking downtown. The thoughtfully designed kitchen offers an oversized island with dine-in seating, white wood cabinetry with glass insets, stainless steel Samsung appliances, designer lighting, plantation shutters, and a convenient built-in workspace. Only two of these Park Place floor plans exist. One of the home's most unique features is the custom loft overlooking Plant Street and the West Orange Trail. Complete with a built-in ladder and bench seating, it's an inviting space to read, work, or simply enjoy the view. The first floor offers a private guest suite or study with an en-suite bath and walk-in closet. With special-use permits issued for select Park Place Plant St units, commercial zoning on this level lets you add a professional workspace. Upstairs, the third-floor owner's retreat provides privacy, a spacious walk-in closet, walk-in shower, and additional storage. Lovingly maintained by its original owner for seven years, this home offers low-maintenance, lock-and-leave living in one of Downtown Winter Garden's most desirable locations. The location is hard to beat. Step outside and you're in the heart of what makes Downtown Winter Garden special. Walk to the Saturday farmers market, enjoy the restaurants and shops along Plant Street, hop on the West Orange Trail, or meet friends for dinner without ever getting in your car. Rare in character, remarkable in design, and irreplaceable in location, 480 W. Plant Street is more than a beautiful home. It’s an invitation to fall in love with where you live.

480 W Plant Street, Winter Garden
Winter Garden
$530,000
3 Beds ⋅ 4 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Welcome to modern Hamlin living in this beautiful END-UNIT townhome in highly desirable Winter Garden! Built in 2025 and offering 3 bedrooms, 3.5 bathrooms and over 2,000 square feet across three thoughtfully designed levels, this home combines the space and privacy of a single-family layout with the convenience of low-maintenance townhome living. One of the best features of this floor plan is that ALL THREE BEDROOMS ARE PRIVATE SUITES with their own bathrooms. The first-floor suite is ideal for guests, a home office, multigenerational living or anyone wanting additional separation and privacy. The second floor is the heart of the home, featuring a bright, open-concept kitchen, dining and living area with 42-inch cabinetry, white quartz countertops, stainless steel GE appliances and modern luxury vinyl plank flooring. Step outside to the covered lanai for an additional spot to relax or unwind. Upstairs, the spacious primary suite offers a private retreat along with the home's third bedroom suite. As an END UNIT, this home enjoys additional privacy with no neighbor on one side, plus added natural light. A two-car attached garage provides plenty of storage and everyday convenience, while the abundance of additional parking directly in front of the home makes hosting friends and family refreshingly easy. And then there's the LOCATION. Parkview at Hamlin puts you in the middle of one of Winter Garden's most convenient and sought-after areas, surrounded by restaurants, shopping, groceries, entertainment and everyday essentials. With SR 429 just minutes away, commuting throughout Central Florida is a breeze while still enjoying everything the Hamlin and Horizon West area has to offer. Modern, spacious, exceptionally well located and barely a year old—this is the kind of rental that truly feels like home. Schedule your showing and come see what makes this end-unit Hamlin townhome stand out.

Winter Garden
13846 Fresh Ivy Street, Winter Garden
$699,000
2 Beds ⋅ 3 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
Beautifully appointed and thoughtfully designed, this home offers an exceptional opportunity to enjoy the Del Webb Oasis lifestyle—with the **seller covering the buyer's capital contribution fee PLUS six months of HOA dues!** From the moment you enter, you'll appreciate the attention to detail, sophisticated finishes, and inviting open-concept design. The beautifully appointed kitchen is a standout, featuring crisp white cabinetry, quartz countertops, stainless steel appliances, a gas cooktop, designer lighting, and an expansive center island with seating. The soft, coastal-inspired color palette, beautiful flooring, and thoughtfully selected finishes create a home that feels both elegant and comfortable. The kitchen flows effortlessly into the dining and living areas, making it equally suited for everyday living and entertaining. A dedicated private office or flex space offers additional versatility. Beyond the home itself, **Del Webb Oasis offers an exceptional 55+ lifestyle** with amenities designed for recreation, relaxation, and connection. At the heart of the community is a beautiful 12,000-square-foot clubhouse featuring an indoor/outdoor bar and tavern, coffee lounge, fitness center with Technogym equipment, yoga and movement studio, arts and crafts room, billiards, and gathering spaces. The on-site restaurant offers lunch and dinner on Wednesdays and Fridays, making it easy to meet friends and enjoy an evening out without leaving the neighborhood. Outdoors, residents enjoy a resort-style zero-entry pool with lap lanes, spa, poolside cabanas, pickleball and tennis courts, bocce ball, walking paths, and inviting social spaces. A full-time lifestyle director coordinates a vibrant calendar of neighborhood activities, clubs, fitness classes, trivia nights, social gatherings, and special events. Whether you want to stay active, explore new interests, or simply enjoy time with neighbors, there's always something happening. Ideally situated in Winter Garden, just minutes from Walt Disney World, shopping, dining, and major roadways, Del Webb Oasis offers the perfect combination of resort-style living and everyday convenience. **A beautifully finished home, an engaging community, and valuable seller-paid incentives—your next chapter starts here!**

13846 Fresh Ivy Street, Winter Garden
7183 Summerlake Groves Street, Winter Garden
$465,000
3 Beds ⋅ 3 Baths ⋅ Highlands/Summerlake Grvs Ph 2 SubDv. ⋅ 34787 Zip Code
Located in the desirable Horizon West area of Winter Garden, this home features an open floor plan, neutral finishes, and a functional layout designed for comfortable everyday living. New landscaping enhances the home’s curb appeal, creating a fresh and inviting first impression. Inside, the open living spaces offer versatility for a variety of lifestyles, while newly carpeted bedrooms provide a comfortable retreat. Enjoy the Florida lifestyle with a covered lanai and fenced backyard, offering additional space to relax or entertain. Situated directly across the street from Orange County National Golf Center, this home offers a convenient location for golf enthusiasts and easy access to top-rated schools, Hamlin Town Center, shopping, dining, and Walt Disney World. Experience all that Winter Garden and Horizon West have to offer in this well-located home.

7183 Summerlake Groves Street, Winter Garden
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