Winter Garden Homes for Sale

Winter Garden Homes for Sale

Welcome to Winter Garden, Florida, a charming city nestled in the heart of Orange County. Known for its picturesque landscapes and vibrant community, Winter Garden seamlessly blends small-town charm with modern conveniences. Just a short drive from Orlando, this delightful city offers a perfect escape from the hustle and bustle while still providing easy access to all the attractions of Central Florida.

Winter Garden is renowned for its historic downtown area, where you can stroll along brick-paved streets lined with boutique shops, delightful cafes, and a variety of restaurants serving up delicious cuisine. The city is also home to the West Orange Trail, a 22-mile multi-use trail that invites residents and visitors to enjoy outdoor activities like biking, running, and leisurely walks amidst beautiful scenery.

When it comes to real estate, Winter Garden boasts an impressive selection of homes for sale, catering to a diverse range of lifestyles and budgets. Whether you’re seeking a charming single-family home with a spacious yard, a modern townhouse with contemporary finishes, or a luxurious estate with stunning views, Winter Garden has something to offer everyone. Families will appreciate the top-rated schools in the area, while retirees will enjoy the peaceful atmosphere and friendly neighbors.

With a thriving community spirit, abundant recreational opportunities, and an array of beautiful homes, Winter Garden is not just a place to live; it’s a place to call home. Explore the homes for sale today and discover why so many are choosing to make Winter Garden their forever destination!

Newest Winter Garden Homes for Sale

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
5567 Cypress Hill Road, Winter Garden
$519,995
3 Beds ⋅ 2 Baths ⋅ Orchard Hills Ph 2 SubDv. ⋅ 34787 Zip Code
Stunning 3-bedroom, 2-bathroom home located in the beautiful and desirable Orchard Hills subdivision of Winter Garden, FL. This home boasts a split bedroom plan, offering privacy and space, with carpeted bedrooms for added comfort. The master suite features a garden tub, perfect for unwinding after a long day. The open floor-plan is ideal for entertaining, with wood look tiled living areas and modern fixtures adding a touch of elegance. The kitchen is equipped with stainless steel appliances, ready for your culinary adventures. The interior has been freshly painted, giving the home a clean and bright feel. Step outside to a manicured lawn and a fence enclosed backyard, perfect for outdoor activities. Not to mention lawn service is included in the rent! The screen enclosed rear patio is a great spot for relaxation, while the front porch offers a scenic pond view, adding to the home's charm. The property also includes a large interior laundry room and a two-car garage for your convenience. As part of a vibrant community, you'll have access to a community pool, fitness center, and clubhouse. This home is not just a place to live, but a lifestyle to enjoy. Come and experience the comfort and convenience this home has for you.

5567 Cypress Hill Road, Winter Garden
15633 Panther Lake Drive, Winter Garden
$2,395,000
4 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
**Organic Modern Design. Intelligently Connected. Effortlessly Luxurious.** Discover extraordinary lakefront living in Winter Garden's Lakeshore Preserve community. Reimagined with nearly $1 million in renovations, this stunning residence blends sophisticated design, intelligent technology, and five-star resort-inspired living. Featured in *The Local Magazine's 2026 Home Issue*, the home showcases organic modern design with European and Mediterranean influences. Limewash walls, graceful archways, wide-plank flooring, custom millwork, and designer lighting create a warm, sophisticated atmosphere. A sculptural staircase with sweeping curved walls and a dramatic cascading chandelier makes an unforgettable statement. The beautifully appointed kitchen features custom cabinetry, premium JennAir appliances, a double-stacked quartz island, quartz backsplash, and beverage refrigeration. A walk-in pantry and drop zone add functionality. The primary suite offers a spa-inspired bath with a freestanding soaking tub, programmable shower, and custom California Closets. Additional highlights include a designer laundry room, upstairs entertainment loft, and equipped home gym with sauna. What truly sets this home apart is its seamless integration of technology. Control4 automation connects customizable Philips Hue lighting, Sonos audio, motorized shades, smart thermostats, security, and other features, making everyday luxury feel effortless. Outdoors, an infinity-edge pool with cascading waterfall overlooks Panther Lake. A two-level pool deck, covered entertaining areas, outdoor fireplace, integrated speakers, and motorized lanai screens create a private resort experience. Architectural lighting and a mosquito misting system add comfort and ambiance. Additional features include a whole-house generator, climate-controlled garages, EV charging, extensive security, and a professional smart-home technology transfer service for the new owner. Lakeshore Preserve offers included lawn care and a convenient location near Walt Disney World and SR 429

15633 Panther Lake Drive, Winter Garden
16549 Parable Way, Winter Garden
$545,000
4 Beds ⋅ 4 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Virtually Staged. 2023 build new house! Highly desirable Storey Grove community! NO CDD.Low HOA fee! Beautifully maintained 4-bedroom, 3.5-bath home in the highly desirable Storey Grove community! Featuring a thoughtfully designed floor plan with TWO Primary suites—one conveniently located on the FIRST floor and the other upstairs—this home offers exceptional flexibility for multi-generational living, extended family, or hosting guests. The functional and versatile layout provides comfortable living spaces ideal for both everyday living and entertaining. Enjoy the convenience of living in a family-friendly community with a community swimming pool and the added benefit of having elementary and middle schools right within the neighborhood—making daily school commutes easier for busy families. one of Storey Grove's most attractive features is its convenient location near Walt Disney World, offering easy access to world-famous theme parks, shopping, dining, and entertainment. With convenient access to major highways and everyday essentials, this home combines a desirable location with comfortable Florida living. Easy Access to Major Highways, Shopping, Dining, and Entertainment Don't miss this wonderful opportunity to enjoy comfort, flexibility, and convenience in the sought-after Storey Grove community, just minutes from the magic of Disney!

16549 Parable Way, Winter Garden
14503 Avenue Of The Rushes, Winter Garden
$850,000
4 Beds ⋅ 4 Baths ⋅ Signature Lakes SubDv. ⋅ 34787 Zip Code
Pro Pics Coming Soon - 1st time on the market * Welcome to this beautiful and incredibly maintained home offering 4 bedrooms, 3.5 bathrooms, and approximately 3,315 square feet of living space in the desirable Signature Lakes community of Independence * Built in 2007, this spacious two-story home offers an inviting blend of comfort, style, and room to entertain * Attractive curb appeal, a welcoming covered entry, paver driveway, and tropical landscaping create a memorable first impression * Inside, the generous floor plan provides flexibility for everyday living, entertaining guests, and enjoying the Florida lifestyle * Step outside to the private screened pool area and create your own backyard retreat, perfect for relaxing and enjoying the sunshine year-round * Conveniently located near shopping, dining, major roadways, and the many amenities of Winter Garden, this property offers an excellent opportunity to enjoy the Central Florida lifestyle, with community recreation and outdoor activities. Community amenities include a clubhouse, 2 resort-style swimming pools, fitness facilities, tennis and basketball courts, playgrounds, parks, and community boat ramps and docks providing access to Lake Hancock.

14503 Avenue Of The Rushes, Winter Garden
13055 Sandcastle Drive, Winter Garden
$874,990
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated within walking distance of the amenity center offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an enclosed flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where soft-close cabinetry with clear glass uppers meets luxurious quartz countertops and a decorative tile backsplash. Thoughtfully designed features like easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including double ovens and a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a walk-in shower with a built-in bench and rain shower head, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, matte black hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

13055 Sandcastle Drive, Winter Garden
390 Grove Court, Winter Garden
$585,000
3 Beds ⋅ 2 Baths ⋅ Westlake Manor 1st Add SubDv. ⋅ 34787 Zip Code
LOCATION, LIFESTYLE & CHARM JUST BLOCKS FROM HISTORIC DOWNTOWN WINTER GARDEN! *** NO HOA *** Enjoy the best of Winter Garden living in this ideally located 3-bedroom, 2-bath home with 2-car garage and 10 X 16 shed, just a few blocks from the heart of historic downtown. Walk or hop in your golf cart and head to Plant Street to enjoy charming restaurants, boutique shopping, the popular Crooked Can Brewery, the Farmers Market, and the downtown splash pad. With so much to explore just moments from your front door, this is an exceptional opportunity to embrace the walkable, golf-cart-friendly lifestyle that makes Winter Garden so desirable. Just a few blocks to the north is Newton Park where you can enjoy stunning sunsets, a playground, community events, and a BOAT RAMP. Situated on just over a QUARTER-ACRE, this property offers a spacious FENCED backyard with plenty of room to create your own outdoor oasis, including the potential for a pool. There may also be room along the south side of the home for boat parking or additional storage. Inside, the thoughtfully designed split-bedroom floor plan offers three bedrooms, two baths, a welcoming WOOD-burning fireplace, family room, living room, and formal dining area. Embrace Florida living year-round with a large screened-in patio and open patio, perfect for entertaining, relaxing, or enjoying the generous outdoor space. The kitchen overlooks the backyard and has been enhanced with stone counters and updated STAINLESS appliances. The primary bedroom features a walk-in closet that connects to the bath and backyard. The second bedroom includes a spacious walk-in closet and the third bedroom has a built-in closet. The laundry area is adjacent to the garage (under air) and has access to the side yard. Major UPDATES include: newer roof (2020), AC (2019), updated windows, plumbing, and kitchen appliances. Whether you’re looking for a home with room to personalize, space to enjoy the outdoors, or an unbeatable location close to the shops, dining, trails, and vibrant community atmosphere of downtown Winter Garden, this property offers an opportunity to enjoy the best of both worlds. Additional Winter Garden highlights: Newly opened, Tucker Ranch, a 209 acre nature preserve with canoe/kayak launch, trails, and more. The 22 mile long, West Orange Trail, just blocks away. Conveniently located near interstate travel (429, I-4, East-West Expressway), theme parks, golf courses, and grocery shopping. First time to market for this well loved home. Sold AS-IS. Buyer to verify measurements and property information. A prime location, a golf-cart-friendly way of life, and endless possibilities await!

390 Grove Court, Winter Garden
14492 Sunbridge Circle, Winter Garden
$1,060,000
5 Beds ⋅ 4 Baths ⋅ Bradford Crk-Ph Ii SubDv. ⋅ 34787 Zip Code
Welcome to the gated community of Bradford Creek in Winter Garden. This luxurious home has 5 bedrooms, 4 bathrooms and a 3-car garage. The kitchen features an over extended island, walk in pantry, 5-burner gas cooktop, top of the line appliances. Enjoy the oversized covered patio with friends and family. Great for entertaining. There are two ensuite bedrooms, one downstairs, and one upstairs, perfect for mother-in-law and/or guests. The downstairs ensuite is hidden behind a custom built secrete door with its private access to the backyard. The master bedroom is huge with 2 walk-in closets and a bathroom features dual rain shower heads. This home is top of the line with all modern accessories like Cat 6 Ethernet, tankless gas water heater, ring camera at front door and smart lights and much more. Come see for yourself.

14492 Sunbridge Circle, Winter Garden
15102 Stuttgart Alley, Winter Garden
$525,000
4 Beds ⋅ 3 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Amazing 4 bedroom 2.5 bath home in the Watermark community near the heart of Hamlin off 429. Built in 2020 with 2204sf, this home offers an open floor plan with great style, architecture, and tasteful decor. The open-concept with kitchen, dining, living room, and cute side cubby combined is great for entertaining. Spacious living areas, contemporary fixtures, and vinyl flooring through out the first floor. The open kitchen is well designed and very pleasing to view with white upgraded cabinets, crown molding, accented with all stainless-steel appliances, quartz countertops, tiled backsplash, and a walk-in pantry. Second floor has a nice size loft, and enter into the large primary bedroom with double doors with huge primary bath. Two separated large vanities, large walk-in shower, large closet, linen closet and toilet room. The washer and dryer have a large laundry room and the other bedrooms share the hall bath with large counter and dual sinks. The back driveway has pavers up to the house and the front of the house looks over a huge, dry retention field. The neighborhood has two community pools, a deluxe resort-style pool and splash pad equipped with cabanas, a nearby gym, and a cool Fire pit overlooking a small pond lined up for viewing of the Disney fireworks! Located perfectly near the heart of Hamlin off Seidel Rd and 429 with convenience just minutes away from brand-new restaurants, shopping, healthcare facilities.

15102 Stuttgart Alley, Winter Garden
14026 Frasier Street, Winter Garden
$464,900
3 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code
SELLER OFFERING $10,000 TOWARDS BUYER CLOSING COST WITH AN ACCEPTABLE OFFER!! Welcome to this beautiful 2023-built home in the desirable Highland Ridge community of Winter Garden! Featuring 3 bedrooms, 2.5 bathrooms, and 1,985 square feet of thoughtfully designed living space, this home offers the perfect combination of modern comfort, functionality, and energy efficiency. Step inside and discover a bright, spacious open-concept main floor, ideal for everyday living and entertaining. The inviting covered front porch adds charm and provides a wonderful place to relax and enjoy the Florida lifestyle. Upstairs, you’ll find a versatile loft perfect for gathering and relaxation, along with a private primary suite offering comfort and privacy. The additional bedrooms provide flexibility for family members or guests. Built by Meritage Homes, known for its innovative energy-efficient features, this property is designed with comfort and potential energy savings in mind. Additional highlights include a two-car garage and access to the community pool. Location is another outstanding feature! Just a short walk from the new Ovation Elementary School and the Flamingo Crossings shopping center, offering a variety of restaurants, fast-casual dining options, grocery stores, a fitness center, and convenience stores, making everyday living exceptionally convenient. The property also provides easy access to major roadways and Orlando’s world-famous attractions. Don’t miss your chance to own a nearly new home in one of the Orlando area’s most desirable locations. Schedule your private showing today!

14026 Frasier Street, Winter Garden
2010 Boss Hewett Street, Oakland
$1,450,000
5 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code
Beautiful 2022-built home in Hull Island featuring 5 bedrooms, 4 full bathrooms, approximately 3,781 heated square feet, a private pool, and a two-car garage. Open-concept living with a gourmet kitchen, quartz countertops, a spacious loft, and two primary suites, including one on the first floor. Community amenities include a pool, trails, playground, dog park, and private dock. Buyer to verify all measurements, HOA terms, and property details.

2010 Boss Hewett Street, Oakland
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