Winter Garden/Oakland Homes with Pool View

Winter Garden/Oakland Homes with Pool View

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant community is renowned for its charming small-town atmosphere, rich history, and stunning natural beauty. With its picturesque landscapes and friendly neighborhoods, it’s no wonder that Winter Garden and Oakland have become highly sought-after destinations for families and individuals alike.

One of the highlights of this area is its stunning selection of homes, many of which offer breathtaking pool views. Imagine waking up each morning to the serene sight of crystal-clear waters glistening in the sunlight, surrounded by lush landscaping and vibrant gardens. Whether you’re enjoying a leisurely swim, hosting a barbecue with friends, or simply unwinding with a good book by the poolside, these homes provide the perfect backdrop for a luxurious and relaxing lifestyle.

Winter Garden boasts a rich array of amenities, including the historic downtown area filled with delightful shops, restaurants, and parks. The West Orange Trail offers miles of scenic paths for walking, jogging, and biking, allowing residents to embrace the great outdoors. With a strong sense of community and top-rated schools, Winter Garden and Oakland are ideal for families looking to settle down.

Whether you’re seeking a cozy retreat or a spacious family home, the properties in this region with pool views promise a lifestyle of comfort, leisure, and elegance. Come explore the charm of Winter Garden and Oakland, where your dream home awaits!

Newest Winter Garden/Oakland Homes with Pool View

$1,100,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to your LAKEFRONT dream home and backyard oasis! This popular “Delmar” floor plan with 120’ of DOCKABLE lake frontage on skiable Hickory Nut Lake which expends 403 acres. You will love the lake lifestyle enjoying boating, waterskiing, kayaking, or fishing! This is a great fishing lake known for it’s Largemouth bass, Bluegills, and Spotted Gars. When you’re done boating, you can finish the day in your heated swimming pool or spa. The pool and spa have all the works, including an electric AND solar heater, plus pool lights for night swimming. This home features a sizable covered lanai perfect for dining a la fresca by the pool enjoying the lake views with all the privacy having no rear neighbors. When night time comes, you will enjoy your nightly DISNEY fireworks view. A bonus of this lot is that it is pie shaped, so there is a spacious yard beside the pool that is fenced in for your furry friends. This sprawling 1 story home is located on a small alcove offering privacy from the main access road. You can sit on the covered front porch enjoying sunset views. The interior of this home is perfect for entertaining, featuring an open concept living area complete with family room/kitchen/dining combo. The stunning kitchen features a wall oven and wall microwave, cooktop, and large walk-in pantry. This “emerald series” house has all the upgrades including tile roof, custom woodwork and wainscoting, 8 ft interior doors, tray ceilings, whole house water softening system, luxury LVP all throughout (no carpets!), trim lights built into the soffit for all of your holiday lighting needs, and a new dishwasher. The exterior was hand painted in August 2026, so this is truly a turn key home! 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, water view, walking trails, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. 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 provides!

10043 Little Alcove Loop, Winter Garden
$2,860,000
6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code
Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful Hancock Lake family friendly home is custom built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat and 2 jet skis. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, manicured gardening beds for your green thumb and plenty of room for outdoor games and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry, cabana bath and a custom salt pool showcasing a water slide, Fiber optic lighting, solar heated and whimsical Disney characters embedded in the rock’s facade. Relax to lake views, or pull down the projector screen for a movie then watch the Disney’s fireworks nightly over the lake. The home has a freshly painted exterior and interior with crown trim throughout. The Kitchen space is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating. The first level’s primary suite with patio access was previously a media room complete with surround sound that remains intact. The loft with a balcony overlooking the patio and lake is prepped for entertaining. Two additional ensuites, 3 more bedrooms and a laundry room are also on the upper level. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updated. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden
$1,095,000
5 Beds ⋅ 4 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code
Welcome Home! Meticulously maintained home boasting with upgrades on an oversized conservation lot with peaceful pond views. Designed for both everyday living and entertaining, features a completely remodeled kitchen with quartz countertops, premium Café appliances, designer backsplash, a massive island with sitting space, upgraded lighting and a custom walk-in pantry. The first floor includes a private office, spacious family room, guest suite with a full bath, laundry room, formal living, and dining room. Porcelain tile flows throughout the main living areas, French doors lead to your private backyard retreat with a fully screened lanai overlooking the saltwater pool and spa, complete with new tile. Upstairs you'll find a stunning media room complete with theater seating and a granite wet bar, 4 bedrooms and a full bath. The primary suite features tray ceiling, plantation shutters, dual walk-in closets, and remodel ensuite bath. Updates include dual vanities, walk-in glass shower, clawfoot tub, and stunning upgraded tile throughout. Two car garage with an upgraded paver driveway. Located in a highly sought-after community of Westfield Lakes. Excellent public schools and convenient access to shopping, dining, and major highways, this exceptional home offers the perfect combination of luxury, comfort, and location. Schedule a private showing today!

626 English Lake Drive, Winter Garden
$2,125,000
5 Beds ⋅ 5 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code
Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

16038 Johns Lake Overlook Drive, Winter Garden
$850,000
6 Beds ⋅ 4 Baths ⋅ Johns Cove SubDv. ⋅ 34787 Zip Code
Exceptional 6-bedroom, 4-bathroom home on a private cul-de-sac in the highly desirable gated community of Johns Cove. This spacious residence features formal living and dining rooms, a large family room, soaring vaulted ceilings, and a double staircase. The kitchen offers stainless steel appliances, granite countertops, a large island, abundant cabinetry, and a breakfast area with tranquil pond views. The first-floor primary suite overlooks the pool and includes an en-suite bath with dual vanities, garden tub, separate shower, and walk-in closet. Upstairs offers generously sized bedrooms and a dedicated movie room. Enjoy a screened heated saltwater pool and spa, updated full pool bath, covered lanai, private balcony, and no rear neighbors. Residents enjoy a private boat ramp on Johns Lake, ideal for bass fishing, boating, paddle boarding, and kayaking. Near West Orange Trail, Downtown Winter Garden, Winter Garden Village, dining, shopping, and top-rated schools.

1603 Johns Cove Ln, Oakland
$1,359,999
4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 2 & 5 SubDv. ⋅ 34787 Zip Code
*** NEW PRICE! *** Welcome to this spacious 4-bedroom, 3.5-bath pool home offering 4,000 square feet in the highly sought-after Overlook at Hamlin community in Horizon West. Showcasing Lake Hancock views throughout the home and Disney fireworks in the distance, this property combines generous living space, impressive architecture, and an unbeatable location in one of Winter Garden's most desirable communities. From the moment you arrive, you'll appreciate the paver driveway, fresh landscaping, side-entry two-car garage, and curb appeal. Step inside to find a formal dining room and home office. Continue into the heart of the home where soaring ceilings and a dramatic two-story design create a bright, open atmosphere. The expansive family room showcases picturesque pool and lake views, while the open-concept layout flows seamlessly into the kitchen and casual dining area, making it ideal for everyday living and entertaining. The kitchen features granite countertops, light cabinetry, two oversized islands, abundant prep space, a walk-in pantry, and a butler's pantry ideal for a coffee station. Stainless steel appliances include a Monogram built-in oven and microwave, Monogram dishwasher, and a Monogram five-burner natural gas cooktop. The first-floor primary suite offers a private retreat with pool views, two walk-in closets, and an ensuite bath complete with dual vanities, a garden tub, and a large glass-enclosed shower. An impressive staircase with decorative iron balusters leads to the second floor, where an open overlook adds to the home's spacious feel. Upstairs you'll find three additional bedrooms, all with walk-in closets, two full bathrooms, a large loft perfect for a media room or secondary living area, and a versatile flex room that can serve as a home gym, study, playroom, hobby room, or potential fifth bedroom. Combined with the dedicated first-floor office, these flexible spaces provide exceptional versatility for remote work, multi-generational living, or growing households. Two upstairs bedrooms enjoy Lake Hancock views. Step outside to the expansive screened lanai with space for outdoor dining, relaxing, and entertaining. The saltwater pool and Lake Hancock views create an exceptional outdoor setting. Residents of Overlook at Hamlin enjoy access to a clubhouse, fitness center, resort-style pool, playgrounds, golf cart-friendly streets, and community lake access. Located just minutes from Hamlin Town Center, you'll enjoy convenient access to shopping, dining, waterfront restaurants, grocery stores, PopStroke, Cinépolis Luxury Cinemas, Urban Air, and everyday conveniences. A rare opportunity to own a spacious pool home with Lake Hancock views in the heart of Horizon West and Winter Garden's thriving Hamlin area.

15264 Shonan Gold Drive, Winter Garden
$785,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code
Experience effortless luxury just 2 miles from Walt Disney World in this impeccably maintained, like-new 2024 residence located within the highly sought-after Del Webb Oasis community. Perfectly positioned directly across from the spectacular amenity campus, you'll enjoy the rare convenience of simply strolling across the street to indulge in world-class resort-style living every day. From the impressive 12,000-square-foot clubhouse featuring a coffee bar, resident lounge, and wine lockers to the zero-entry resort pool, hot tub, state-of-the-art fitness center, tennis and pickleball courts, every luxury is just moments from your front door. Designed with both elegance and functionality in mind, this stunning home welcomes you with an expansive open-concept floor plan that seamlessly connects the chef's kitchen, dining area, and spacious living room, creating the perfect setting for entertaining or relaxed everyday living. The gourmet kitchen is beautifully appointed with upgraded quartz countertops, a large eat-in breakfast bar island, 42-inch cabinetry, premium stainless steel appliances including a gas range, and an extra-deep double-basin sink. Beautiful upgraded flooring flows throughout the home, offering both timeless style and easy maintenance. Step outside to your own private outdoor retreat, where a screened-in pool and covered lanai create an inviting space to enjoy Florida's year-round sunshine. Whether sipping morning coffee on the charming front patio or unwinding with a glass of wine beside your sparkling pool in the evening, you'll appreciate the peaceful surroundings and exceptional privacy. The thoughtfully designed split-bedroom floor plan offers an ideal balance of comfort and privacy. Tucked away at the rear of the home, the luxurious primary suite is filled with natural light and features a spacious walk-in closet and an elegant spa-inspired bath complete with dual quartz vanities and an oversized walk-in shower. A generously sized secondary bedroom and beautifully finished guest bath are situated at the front of the home, providing a welcoming retreat for family and visitors alike. Additional highlights include a large laundry room, convenient drop zone, and an energy-efficient tankless water heater for endless hot water. Beyond the gates, you'll find yourself just minutes from Disney, championship golf, premier shopping, exceptional dining, and Central Florida's most desirable attractions. Combining an unbeatable location, refined finishes, and unparalleled walkability to Del Webb Oasis' extraordinary amenities, this exceptional home offers a truly elevated lifestyle where every day feels like a luxury vacation.

13175 Sunny Retreat Lane, Winter Garden
$1,699,000
5 Beds ⋅ 5 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this exceptional lakefront retreat on the shores of Lake Apopka, where breathtaking water views, luxury upgrades, and exceptional outdoor living come together to create the ultimate Florida lifestyle. Offering 5 bedrooms, 4.5 bathrooms, and over 4,000 square feet of thoughtfully designed living space, including a convenient first-floor bedroom, this beautifully updated residence showcases extensive high-end improvements throughout, creating a move-in-ready experience for the next owner. From the moment you arrive, you'll appreciate the extensive upgrades throughout the home, including porcelain tile throughout the main living areas on the first floor, engineered white oak hardwood flooring throughout the second level, a custom wood and iron staircase, upgraded cabinetry, quartz countertops, designer finishes, and a beautifully appointed kitchen featuring premium KitchenAid appliances, a gas cooktop, and custom soft-close cabinetry. Designed for both everyday living and entertaining, the backyard is a true showpiece. Enjoy a resort-style saltwater pool and spa, gas-heated for year-round enjoyment, expansive outdoor living areas, and a fully equipped summer kitchen featuring premium Blaze appliances. Electric screens allow you to enjoy outdoor dining and entertaining comfortably while taking in the peaceful lakefront setting and stunning sunset views. Boating enthusiasts will appreciate the private dock complete with a 5,000-pound boat lift, offering direct access to Lake Apopka, one of Florida's largest lakes. With more than 30,000 acres of open water to explore, the lake offers endless opportunities for boating, fishing, watersports, and unforgettable sunset cruises. Known for its trophy bass fishing, abundant wildlife, and expansive waterfront views, Lake Apopka provides a rare opportunity to enjoy true lakefront living with the freedom and space that few Central Florida lakes can offer. This property delivers the waterfront lifestyle Florida is known for. Additional highlights include a convenient first-floor bedroom, a second-floor laundry room, solar panels that will be paid off at closing, natural gas service, a Culligan water filtration system, dual pool pumps, and city sewer, a significant advantage for a waterfront property. Ideally located just minutes from Downtown Winter Garden, shopping, dining, and major roadways, this exceptional lakefront residence offers the perfect balance of luxury, recreation, and everyday convenience.

1144 Hull Island Drive, Winter Garden
$649,900
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1c SubDv. ⋅ 34787 Zip Code
Welcome to your private oasis in the highly desirable community of Waterleigh! This rare gem stands out as one of the few homes in the neighborhood to feature its very own private, heated saltwater pool, complete with a spacious covered patio, an impressive newly screened lanai, and the ultimate privacy of no rear neighbors. Boasting one of the most sought-after single-story designs, this open and light-filled home welcomes you with sophisticated new wainscoting architectural details and brand-new, upgraded flooring throughout all four bedrooms. The heart of the home is an incredible gourmet kitchen featuring a massive quartz island illuminated by high-end glass pendant lighting, premium appliances, custom cabinetry, and a stunning backsplash that flows seamlessly into the spacious living and dining areas. Unwind in a luxurious primary suite showcasing elegant tray ceilings and a grand walk-in closet outfitted with a brand-new custom organization system. The upgraded primary bath offers a spa-like experience with granite counters, double sinks, a large shower, and an oversized soaking tub. Every detail has been meticulously enhanced, including a fully renovated laundry room, a pristine epoxy-finished garage floor, sealed and cleaned outdoor pavers, and a freshly repainted exterior. The home is also equipped with permanent outdoor Govee smart lights, allowing you to easily customize your exterior illumination for holidays or everyday ambiance. Located just 15 minutes from Walt Disney World, you can even enjoy the magic of the nightly Disney fireworks right from your own home. Waterleigh offers an unmatched, low-maintenance resort lifestyle where the HOA includes all lawn care, giving you more time to enjoy the two community clubhouses, resort pools, fitness centers, garden, mini-golf, volleyball, and scenic lake viewing docks. Schedule your tour today to experience this highly upgraded, move-in-ready masterpiece!

16131 Hampton Crossing Drive, Winter Garden
$1,125,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat. Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb appeal. A custom front door opens to a partially screened wraparound front porch, perfect for morning coffee or evening chats. Inside, rich hardwood floors span the main level, complemented by abundant natural light, crown molding, plantation shutters, designer lighting, brass floor outlets in the living room & office, and ceiling fans throughout. The kitchen features granite countertops, a farmhouse sink, stainless steel appliances, tile backsplash, under-cabinet lighting, a beverage refrigerator, & a new Bosch dishwasher and microwave (2023). Open to the living & dining areas, it overlooks the front porch & connects seamlessly to outdoor living through French doors. A flexible front room serves as an office, study, or playroom. A powder room serves guests. The first-floor owner's suite overlooks the pool & offers dual granite vanities, a spa-style walk-in shower, linen storage, custom California Closets, & direct laundry room access. Upstairs, hardwood flooring continues throughout 3 spacious bedrooms, including one en-suite, plus two full baths and a generous loft ideal for theater, fitness, playroom, or guest retreat. A whole-home Generac natural gas generator keeps lights, air conditioning, & appliances running during outages. Step outside to one of Oakland Park's rare full-size Jandy-iAqualink-controlled saltwater pool & spa. The pool measures approximately 12' x 30' with depths from 3' to 5' & features an 8' x 12' sun shelf with bubbling fountain and umbrella sleeve. The approximately 6' x 8' spa includes four therapy jets and heats in 20-30 minutes. Equipment includes a 2.7 HP Jandy Variable-Speed Energy-Efficient Pump & Jandy 400,000 BTU natural gas heater. A travertine pool deck, oversized covered rear porch, vinyl-fenced yard with dual gates, & three-car garage with built-in storage racks complete the outdoor experience. Oakland Park offers a waterfront, golf-cart-approved lifestyle with two resort-style pools, a clubhouse, dog park, playgrounds, parks, & spectacular sunsets. Two blocks from the waterfront trail, minutes from the 22-mile West Orange Trail, & near multiple parks. Historic downtown Winter Garden is a golf cart ride away, offering Crooked Can Brewery, rooftop dining, boutique shopping, splash park, Farmers Market, live theater, golf cart parades, 5Ks, book clubs, poker nights, and more. Convenient access to major interstates, premier golf courses, shopping, & Central Florida theme parks. Additional features: fresh interior/exterior paint (2021), Apple HomeKit-compatible door locks, thermostats & ceiling fans, Apple Secure Video cameras at the doorbell, front entry, pool area & indoor locations, new remote-controlled high-velocity fans on both porches, Apple HomeKit-controlled owner's bath fan, outlets inside primary bath cabinetry, & a state-of-the-art termite detection and control system with full warranty. Lovingly maintained & thoughtfully enhanced throughout, this one-of-a-kind Oakland Park pool & spa home is a special opportunity. Your oasis is waiting. Make it yours.

925 Easley Avenue, Winter Garden
$480,000
2 Beds ⋅ 2 Baths ⋅ Grova Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park, a luxury vacation condo-hotel community offers owner privacy and convenience. Located 5 minutes from Walt Disney World, ownership of the largest 2-bedroom provides a family friendly place to vacation and relax. Let's discuss more about this 2B When you step through the door, you enter directly into the living space. The unit features in-unit laundry, with full-size washer and dryer. The kitchen is well-equipped with all major appliances, so you can certainly cook here if desired. The living space is spacious, and also includes a dining area. You can be making $ on the day of closing! Financial statements are available! Please note that this is a condo-hotel, so you could not live here full time due to zoning restrictions

14501 Grove Resort Avenue Unit 3425, Winter Garden
$329,900
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Turnkey 2-bedroom fully furnished and equipped condo-hotel residence at The Grove Resort & Water Park Orlando, just minutes from Walt Disney World and Orlando’s top attractions. Unit 3632 offers the perfect combination of personal enjoyment and income-producing potential in one of Central Florida’s most desirable vacation destinations. This spacious residence features an open-concept layout, modern kitchen with granite countertops and stainless steel appliances, comfortable living and dining areas, and a private balcony ideal for relaxing after a day in the parks. The highly desirable two-bedroom floor plan appeals to families and groups, creating strong rental demand and excellent short-term rental potential. Whether you are seeking a second home, vacation retreat, or investment property, this is a true turnkey opportunity ready for immediate use or rental. Owners and guests enjoy world-class resort amenities including a private water park, lazy river, multiple pools, surf simulator, full-service spa, fitness center, on-site restaurants and bars, arcade, family activities, shuttle service to the theme parks, and professional on-site management. Located in the heart of Orlando’s thriving tourism market with year-round visitors, this property offers exceptional lifestyle value and strong investment appeal. Schedule your private showing today.

14501 Grove Resort Avenue, Winter Garden
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