Winter Garden Homes with Lake Front Water Frontage

Winter Garden Homes with Lake Front Water Frontage

Welcome to Winter Garden, Florida – a picturesque city that beautifully blends small-town charm with modern amenities. Nestled just west of Orlando, Winter Garden is known for its vibrant downtown area, rich history, and stunning natural surroundings. With its lush landscapes and friendly community, this delightful city offers an exceptional quality of life for residents and visitors alike.

One of Winter Garden's most enchanting features is its stunning lakefront properties. Imagine waking up every morning to panoramic views of crystal-clear waters and breathtaking sunsets that paint the sky in vibrant hues. Homes with lakefront waterfrontage in Winter Garden provide a unique opportunity to enjoy the tranquility of lakeside living while still being close to urban conveniences. Whether you’re sipping coffee on your private dock or hosting family gatherings by the water, these properties offer a lifestyle that is both serene and exhilarating.

The area is also a haven for outdoor enthusiasts, with an abundance of parks, trails, and recreational activities. Explore the scenic West Orange Trail, perfect for biking and walking, or spend a leisurely day fishing, kayaking, or paddleboarding on one of the many pristine lakes. Winter Garden’s charming downtown, filled with boutique shops, delightful eateries, and community events, creates a warm and welcoming atmosphere that fosters a strong sense of belonging.

With its stunning lakefront homes and vibrant community spirit, Winter Garden is more than just a place to live—it's a lifestyle waiting to be embraced. Discover your dream home in this enchanting city and experience all that Winter Garden has to offer!

Newest Winter Garden Homes with Lake Front Water Frontage

$924,900
3 Beds ⋅ 4 Baths ⋅ Hickory Hammock SubDv. ⋅ 34787 Zip Code
Set along the water with peaceful views woven into everyday living, this beautifully maintained home offers an inviting blend of comfort, space, and relaxed waterfront living. An open, thoughtfully designed layout creates an effortless flow for daily life and entertaining, while abundant natural light, warm finishes, and colorful landscaping add to the home’s welcoming feel. The main living areas are enhanced by quality vinyl plank flooring, quartz countertops, Pottery Barn light fixtures, and a spacious kitchen with white cabinetry, stainless appliances, a large island with seating, and direct sightlines to the dining and living spaces. A Sonos whole-house audio system adds integrated sound throughout the home, while concealed living-room TV wiring keeps the installation clean and streamlined. Additional upgrades include higher ceilings, a tray ceiling in the primary bedroom, upgraded window treatments, whole-house water filtration, irrigation, and HVAC air-quality enhancements with a UV/blacklight component. The primary suite offers a relaxing retreat with peaceful water views, dual vanities, a soaking tub, walk-in closet, and an upgraded walk-in shower with dual shower heads/spouts, including a rain shower. Upstairs, a generous bonus/loft area provides flexible space for a media room, home office, playroom, or additional lounge. Outdoor living is equally inviting, with a screened lanai overlooking the water, a fenced backyard, and upgraded electrical capacity designed to support the higher-output requirements of a large hot tub or spa. The setting is ideal for enjoying morning coffee, evening sunsets, and the quiet rhythm of waterfront living. Located within gated Hickory Hammock at Johns Lake, the community is surrounded by Johns Lake, Lake Burnett, and Lake Claire. Johns Lake spans approximately 2,500 acres and is known for bass fishing and water recreation. Community amenities include a resort-style pool with beach entry, clubhouse, fitness center, tennis courts, sand volleyball/multipurpose court, playgrounds, kids’ soccer area, public fishing pier, dog park, and nature trails through wooded areas and native Florida vegetation. With water views from multiple living spaces, thoughtful interior upgrades, flexible living areas, a screened lanai, fenced backyard, and a wide range of community amenities, this home offers a polished and comfortable waterfront lifestyle in a setting designed for both everyday living and leisure.

15199 Lake Claire Overlook Drive, Winter Garden
$384,900
3 Beds ⋅ 3 Baths ⋅ Villas/Tucker Oaks SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained and thoughtfully upgraded home in the desirable gated community of Tucker Oaks in Winter Garden. Offering 3 bedrooms, 2.5 baths, and over 1,700 square feet of living space, this home combines modern updates, energy-efficient features, and comfortable Florida living. The kitchen was beautifully updated in 2023 with quartz countertops and backsplash, 42-inch soft-close cabinetry, a Kraus 30-inch single-bowl stainless steel sink, and a newer KitchenAid dishwasher. Porcelain tile flows throughout the first floor, while newer luxury vinyl flooring extends up the stairs and throughout the upstairs hallway and bedrooms, complemented by 6-inch baseboards. Major improvements include a 2025 roof, 2022 Carrier A/C with soft-start technology, 2025 water softener, and a dedicated generator outlet. Solar panels help reduce energy costs, while whole-house Vista Luminance V28 8-mil window film, installed in 2023, helps block up to 65% of total solar energy and rejects 99.9% of harmful UV rays. Both the primary and guest bathrooms have been remodeled and feature comfort-height toilets. The laundry room has also been upgraded with additional cabinetry for convenient storage. Step outside to enjoy the screened lanai overlooking the pond, with pebble-stone flooring installed in 2023 and no-see-um screening added in 2026. The fenced-in yard provides added privacy and creates a wonderful outdoor space for relaxing or entertaining while enjoying the peaceful pond views. The garage offers additional convenience with overhead storage racks and a pull-down ladder providing access to the garage attic. Tucker Oaks is a gated community offering a resort-style pool, clubhouse, playgrounds, basketball courts, dog park, sidewalks, and green spaces. The location is hard to beat, with convenient access to the Florida Turnpike and major roadways, while being just minutes from historic Downtown Winter Garden and the popular Plant Street corridor, where you'll find restaurants, shopping, Plant Street Market, the weekly farmers market, and local entertainment. The West Orange Trail is also nearby for biking, walking, and outdoor recreation. With a long list of recent improvements, energy-efficient features, a fenced yard with peaceful pond views, and an ideal Winter Garden location, this home is truly move-in ready and offers the lifestyle you've been looking for.

1432 Scarlet Oak Loop, Winter Garden
$749,000
5 Beds ⋅ 3 Baths ⋅ Wintermere Harbor SubDv. ⋅ 34787 Zip Code
Welcome to the Winter Garden lifestyle! Set behind the gates of desirable Wintermere Harbor, this impressive 5-bedroom, 3-bath pool home offers over 3,700 square feet of beautifully designed living space with the room, flexibility and privacy today’s buyers are looking for. From the moment you walk in, soaring ceilings and generous living spaces create a bright, open feel perfect for both everyday living and entertaining. The heart of the home flows effortlessly to your screened-in pool and private backyard oasis—imagine morning coffee by the water, sunny Florida afternoons by the pool and evenings entertaining family and friends. With five bedrooms and multiple living areas, there’s plenty of space for a home office, guests, playroom or multigenerational living. Beyond your front door, Wintermere Harbor offers gated entry, a playground, park and access to Lake Luntz. And the location is hard to beat! You’re just minutes from Winter Garden’s shopping, restaurants and everyday conveniences, with quick access to SR-429 making it easy to reach Downtown Orlando, the airport and surrounding Central Florida. Walt Disney World and the attractions are also just a short drive away, putting the best of Central Florida practically in your backyard. Spacious, private, gated and perfectly positioned—this is more than a house. It’s the Florida lifestyle you’ve been waiting for.

2102 Green Ash Court, Winter Garden
$178,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Welcome to Your Premier Vacation Gateway at The Grove Resort & Water Park! Located just minutes from Walt Disney World and Orlando’s world-class attractions, this fully furnished 2-bedroom, 2-bathroom condo-hotel unit (#3703) offers the perfect blend of vacation luxury and income-generating potential! ***PRIME CENTRAL VIEW: Positioned directly facing the lush central garden and courtyard, providing a peaceful, scenic backdrop and elevated tropical views right from your private space. ***UNRIVALED RESORT AMENITIES: Guests and owners enjoy full access to the renowned Surfari Water Park, dual water slides, lazy river, FlowRider® surf simulator, zero-entry pools, spa, game room, and multiple on-site dining options. ***TURNKEY & HASSLE-FREE: Professionally managed with on-site rental program options, making personal vacation stays and short-term rentals seamless.*** Whether you're seeking a vacation home, a smart investment property, or a hybrid of both, Unit #3703 delivers unbeatable lifestyle and convenience in the heart of Central Florida's tourism corridor. Schedule your showing today!!

14501 Grove Resort Avenue Unit 3703, Winter Garden
$849,900
4 Beds ⋅ 3 Baths ⋅ Sanctuary/Twin Waters SubDv. ⋅ 34787 Zip Code
Located in The Sanctuary at Twin Waters, and ideally positioned on the community’s largest homesite at the end of a quiet cul-de-sac with no rear neighbors and water views. A long driveway, three-car garage, an oversized, and a fully fenced backyard. Inside, the open-concept layout features 4 bedrooms and 3 full baths, with updated flooring throughout the main living areas and primary suite. The kitchen is complete with stainless steel appliances, an oversized island, quartz countertops, upgraded backsplash, and 42-inch cabinetry. The living room is complete with a stone electric fireplace and custom built-ins. Sliding glass doors open to a screened and covered lanai, creating an easy transition to outdoor living and entertaining. A whole-home solar system, FULLY PAID-OFF, adds energy efficiency, and eliminates the electricity bill. Residents of The Sanctuary at Twin Waters enjoy access to a community pool, playground, walking trails, and private pier. Just minutes from Winter Garden’s Historic Downtown, shopping, dining, Cinepolis Luxury Cinema, Horizon West, the West Orange Trail, major highways, and Orlando’s world-famous theme parks. Call today to schedule a private tour.

16668 Sanctuary Drive, Winter Garden
$729,999
4 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
Welcome to 6158 Meriwether Crescent in Winter Garden! This spacious 4-bedroom home offers a flexible floor plan with plenty of room to spread out, plus a private screened-in pool that makes Florida living easy. The main living areas feature an open layout with wood and tile flooring, while the kitchen offers granite countertops, stainless steel appliances, ample cabinetry and breakfast-bar seating. Large windows throughout bring in plenty of natural light, and multiple living and dining spaces provide flexibility for everyday living, entertaining or working from home. Step outside to the screened pool and patio overlooking a peaceful green setting, creating a great place to relax or entertain year-round. A detached garage with a brick-paver driveway adds even more functionality, while the covered front porch and mature landscaping give the home welcoming curb appeal. The surrounding community offers beautiful green space, walking paths, ponds and a neighborhood gazebo just steps from the home. Conveniently located in Winter Garden with easy access to shopping, dining, schools and everything the area has to offer, this home combines space, privacy and outdoor living in a great location.

6158 Meriwether Crescent, Winter Garden
$638,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to this modern 3-bedroom, 2 and 1/2-bath residence, 1650 square feet located in McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. This Home has a nice welcoming front porch and showcases timeless architecture, upscale designer finishes. Step inside to discover soaring ceilings, beautiful luxury vinyl plank flooring throughout the main living areas. At the heart of the home on the 2nd Story, the gourmet chef's kitchen features custom cabinetry with upgraded hardware, quartz countertops, an oversized island, a gas cooktop, custom vent hood, built-in wall oven, decorative tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room with a Balcony to have coffee in the morning or tea in the evening. Upstairs, an expansive loft offers nice living space. Cathedral ceilings, walk-in closet. One of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market close to Winter Garden Village at Fowler Groves the outdoor Mall and the Orlando International Airport. With convenient access to Florida's Turnpike, SR-429, 408, to downtown Orlando, and Central Florida's world-famous attractions and Themed Parks, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

910 Trowman Aly, Winter Garden
$465,900
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code
LAKEFRONT LUXURY IN SUMMERLAKE! Stunning 4BR/3BA townhome with bonus room, open concept living, brand new roof, state of the art appliances & decorative lighting included! Enjoy breathtaking lake views, nightly Disney fireworks, and a private PVC fenced brick paver courtyard perfect for morning coffee or relaxing. Spacious 2 car garage. Resort style amenities include clubhouse, gym, pool, soccer field, walking trails, tennis court, basketball court, playground, zip line & fishing dock. Walking distance to the Orange County National Golf Center, minutes to Disney, Downtown Winter Garden, endless dining & shopping. A MUST SEE! Buyer to verify room sizes and all measurements. Public records reflect 3BR/2BA; actual configuration is 4BR/3BA plus bonus room

8174 Bluejack Oak Drive, Winter Garden
$245,000
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
$585,000
2 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code
**Click the Link for Virtual Tour** RARE TURNKEY OPPORTUNITY IN THE HEART OF DOWNTOWN WINTER GARDEN! Just three blocks from Plant Street and located within the golf-cart district, this beautifully renovated 2-bedroom, 2-bathroom cottage combines one of Winter Garden?s most sought-after locations with the flexibility of a primary residence, second home or established short term rental. Thoughtfully renovated down to the studs in 2016, the home blends historic cottage character with extensive modern improvements including updated electrical and plumbing, engineered hardwood floors, renovated kitchen and baths, double-pane windows, natural gas tankless water heater, metal roof and A/C was replaced in 2022. The open floor plan features a charming window seat in the living room, while the primary suite offers a walk-in closet and en-suite bath with dual sinks and oversized shower. A second full bath provides direct exterior access to the backyard - convenient for outdoor entertaining or future pool. Outside, the nearly quarter-acre fenced property offers something increasingly difficult to find this close to downtown: room to enjoy. Relax on the restored rear deck beneath the mature shade tree, utilize the approximately 200-sq.-ft. powered shed as storage, workshop or hobby space, and enjoy the convenience of a carport and additional outdoor space. Leave the car at home and walk, bike or take your golf cart to Plant Street, the West Orange Trail, Plant Street Market, Crooked Can, restaurants, boutiques, the farmers market, festivals and downtown entertainment. Currently operated as a short-term rental and offered turn-key with furnishings and accessories included, with existing reservations extending through March 2027. Whether you're searching for a downtown residence, vacation home or investment property, this is an opportunity to own a distinctive piece of the Downtown Winter Garden lifestyle.

325 W Newell Street, Winter Garden
$460,000
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
$2,495,000
6 Beds ⋅ 6 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code
Virtually Staged. Lake Apopka view. Protected Conservation. Detached Guest apartment. Apartment over garage. In-Law suite. Multi-generational living describes 907 Celadon. Homesite is approximately 160 feet deep. A broad rear boundary of designated open space. No residential lot behind the home. The main home highlights include a massive open floor plan, oversized Chef's kitchen, first-floor primary en suite, outdoor summer kitchen, two rooms directly off the foyer offering flexibility for two home offices, or one room as the downstairs en suite for guests or aging family members. The nearly 41-foot screened porch, with built in summer kitchen. The Detached Guest House is 907 Sq Ft, and open studio layout, one bedroom, kitchenette, full bath. Provides flexibility as the in-law suite, mother-in-law suite. Chef's Kitchen, offers generous workspace for more than one cook. Kitchen-Aid ovens and built-in ice maker by Manitowoc. Expansive sliding glass doors open the great room to the green conservation and Lake Apopka views. A long back yard overlooking a deep conservation vista. Room for a pool. The first-floor primary en suite occupies its own wing at the rear and right side 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 lanai. The bathroom features frameless shower, free standing soak tub, and dual sinks across from each other. A custom walk-in closet dressing room —with extensive built-ins, a center island and chandelier complete the wing. Upstairs, three bedrooms and an oversized loft provide the flexibility for a home theater, gaming and homework stations. Daily routines are easier here. Bright blue built-in lockers off the mudroom keep backpacks, sports equipment, shoes and bags organized, while the large laundry room includes a specialty built-in dog wash station. Connected to the main residence by a covered breezeway, the 907 Sq ft detached guesthouse/ADU sits above a 3-car garage and includes a kitchenette, full bath and closet. The garage also includes a golf-cart bay, and EV charging station. The guest house is currently used as a private executive office. Oakland Park and Winter Garden's golf-cart approved community zones is one of the signature advantages, offering easy access to Historic Downtown Winter Garden—Plant Street, the Farmers Market, dining and Crooked Can—just a golf 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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