Winter Garden/Oakland Homes with Private Pool type

Winter Garden/Oakland Homes with Private Pool type

Welcome to the enchanting region of Winter Garden and Oakland, Florida—a picturesque blend of small-town charm and modern convenience nestled just a stone's throw from the bustling heart of Orlando. Known for its vibrant downtown area filled with quaint shops, delightful restaurants, and lush parks, Winter Garden offers a unique lifestyle that combines relaxation and recreation. The nearby Oakland community adds to the allure, showcasing beautiful landscapes and serene surroundings, making it an ideal place to call home.

One of the most sought-after features of homes in this area is the private pool. Imagine stepping out into your own backyard oasis, where you can bask in the Florida sunshine or unwind under the stars, all from the comfort of your home. Homes with private pools in Winter Garden and Oakland offer the perfect escape for families and individuals alike. Whether you’re hosting summer barbecues, enjoying a refreshing dip on a warm day, or simply lounging poolside with a good book, a private pool enhances your living experience.

With a variety of architectural styles and spacious layouts, these homes cater to diverse tastes and lifestyles. From charming single-family residences to modern designs, there’s something for everyone. Plus, the proximity to top-rated schools, recreational facilities, and beautiful nature trails makes this area not just a place to live, but a community to thrive in.

Explore the possibilities of life in Winter Garden and Oakland, where your dream home with a private pool awaits! Embrace the Florida lifestyle and make every day feel like a vacation.

Newest Winter Garden/Oakland Homes with Private Pool type

$890,000
5 Beds ⋅ 5 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code
Stunning two-story house with a permanent lake view. Be enchanted by this magnificent lakefront residence, which combines sophistication, comfort, and a privileged location. It features 5 bedrooms, 4 full bathrooms, and 1 powder room, distributed in a smart and functional layout. The social area impresses with high ceilings in the living room and sliding doors that open onto a large covered veranda, integrated with a heated pool with a safety net, ideal for leisure and entertainment throughout the year. The living room is integrated with the dining room and the spacious and elegant gourmet kitchen, equipped with a generous central island, appliances, and wooden cabinets, perfect for those who enjoy entertaining. The master suite on the ground floor offers complete privacy, as well as relaxing views of the lake and green area, and a full bathroom on the same level. On the second floor, the house also features a versatile loft, ideal for an office, TV room, or social space. The space originally intended for a garage has been carefully adapted into a private gym, and can easily be converted back to suit the new owner's needs. Located in the desirable Hawksmoor community, the property offers complete infrastructure, including a community pool, gym, clubhouse, and walking paths. All this in a strategic location, close to markets, restaurants, shops, a theater, major highways, and Disney parks. A unique opportunity to live or invest. Schedule your visit and be amazed!

16394 Taliesin Street, Winter Garden
$749,900
4 Beds ⋅ 3 Baths ⋅ Black Lake Preserve SubDv. ⋅ 34787 Zip Code
Welcome to 14343 Black Lake Preserve Street in Winter Garden, a beautifully upgraded pool home in the sought-after Black Lake Preserve community. Designed for both everyday living and unforgettable entertaining, this exceptional residence combines luxury finishes, premium technology, and thoughtfully designed living spaces. At the heart of the home is a stunning chef's kitchen featuring an impressive 13-foot center island, a GE Monogram wall oven, Thermador 5-burner cooktop, and a spacious walk-in pantry with custom built-in storage. The kitchen flows seamlessly into the main living areas and is complemented by an elegant formal dining room, providing the perfect setting for holiday gatherings, dinner parties, or everyday meals. Luxury vinyl plank flooring, crown molding, and a cozy fireplace add warmth and sophistication throughout the home. The spacious primary suite offers a private retreat with a custom walk-in closet system, while the dedicated theater room delivers an immersive entertainment experience with a 123-inch screen, 4K projector, and surround sound system. Step outside and enjoy Florida living at its finest. The backyard features a fully equipped outdoor kitchen with grill, griddle, and sink, making it the perfect space for entertaining family and friends. The sparkling pool is equipped with a new heat and cool pump, allowing for year-round enjoyment. Additional upgrades include a Generac whole-home generator, providing security and peace of mind during any season. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, shopping, dining, and area attractions, this move-in-ready home offers the perfect blend of luxury, comfort, and convenience. This is a rare opportunity to own a highly upgraded home in one of Winter Garden's most desirable communities.

14343 Black Lake Preserve Street, Winter Garden
$1,625,000
5 Beds ⋅ 5 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code
LOCATION, LOCATION, LOCATION! Discover a rare gated lakefront retreat in the heart of Winter Garden, tucked away on a quiet, tree-lined cul-de-sac and conveniently located just minutes from local schools, grocery stores, dining, and Downtown Winter Garden. Enjoy grandfathered boat access on Lake Luntz, breathtaking sunset views, a screened pool with grotto seating and waterfall, a fully equipped Florida Grill/Bar room, and a private boathouse with a covered dock, boat lift, pontoon slip, and jet ski slips. Additional highlights include a guest suite, loft, media room, air-conditioned garage with gym/rec space, and two new AC systems installed in 2025—an exceptional combination of privacy, recreation, and waterfront living.

2450 Dahlgren Way, Winter Garden
$3,300,000
7 Beds ⋅ 8 Baths ⋅ Acreage SubDv. ⋅ 34787 Zip Code
Exceptional custom estate on approximately 1.61 acres in Downtown Winter Garden's desirable Golf Cart District, just minutes from Historic Plant Street, the West Orange Trail, shopping, dining, and entertainment. This extensively renovated residence offers over 7,700 square feet of living space with 7 bedrooms, 6 full baths, 2 half baths, spacious living and entertaining areas, a chef's kitchen with premium appliances, marble countertops, wine bar, and an open-concept design. The resort-style outdoor living area features a heated saltwater pool, covered lanai, summer kitchen with pizza oven and built-in grill, and an NBA regulation half basketball court. A detached guest house with a full kitchen provides ideal space for guests, multigenerational living, or a private office. Additional features include a gated circular driveway, oversized 3-car garage with workshop, golf cart garage, mature oak trees, and no HOA. Conveniently located near SR-429, Florida's Turnpike, Winter Garden Village, downtown Orlando, area attractions, and Orlando International Airport.

900 W Plant Street, Winter Garden
$425,000
3 Beds ⋅ 3 Baths ⋅ Suburban Shores Rep Pt Blk 03 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Discover the potential of this spacious 3-bedroom, 3-bathroom home in Winter Garden, offering a flexible layout and plenty of room to make it your own. With 3 full bathrooms and a large flex room, this home provides endless possibilities for a home office, media room, hobby space, game room, or additional living area. The pool bathroom was added in 2018 with wheelchair-accessible features, including a zero-threshold shower and exterior ramp for ease of access. Major improvements include a metal roof (2018), whole-house generator (2017), flex room windows (2018), A/C (2013), and water heater (1999). Enjoy access to Johns Lake with a public boat ramp conveniently located at the front of the neighborhood, making it easy to spend the day boating, fishing, kayaking, or enjoying one of Winter Garden's most popular lakes. Situated with convenient access to Florida's Turnpike, Highway 50, shopping, dining, and everyday conveniences, this home offers a great opportunity for buyers looking for space, versatility, and a desirable Winter Garden location.

17531 N Sunset Terrace, Winter Garden
$1,250,000
4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code
Designed to impress and crafted for everyday living, 5513 Thomas Square Drive is a beautifully upgraded pool home in one of Hamlin's most sought-after communities. Offering 4 bedrooms, 3.5 bathrooms, a private office, an oversized loft, a versatile flex room, and a saltwater pool, this exceptional residence seamlessly blends timeless design with modern comfort. From the moment you arrive, the stone-accented elevation, oversized driveway, and manicured landscaping create unforgettable curb appeal. Inside, soaring ceilings, abundant natural light, crown molding, custom trim work, 8-foot doors, and wood-look tile flooring establish an elegant yet welcoming atmosphere. The dramatic two-story great room is the undeniable centerpiece of the home, showcasing a custom floor-to-ceiling built-in with cabinetry, open shelving, and a heat-producing electric fireplace, beautifully complemented by decorative wood ceiling beams that add warmth and architectural character. The open-concept kitchen is equally impressive, featuring white cabinetry, granite countertops, an oversized center island, stainless steel appliances, a gas cooktop, walk-in pantry, expansive butler's pantry, and a dedicated breakfast nook overlooking the backyard. Privately tucked away on the first floor, the primary suite offers engineered hardwood flooring, dual walk-in closets with custom shelving, and a spa-inspired bath with separate vanities, a soaking tub, and an oversized walk-in shower. A private office with matching engineered hardwood flooring, formal dining room, laundry room, and powder bath complete the main level. Upstairs, three spacious bedrooms, two full bathrooms, an oversized loft, and a flexible bonus room provide endless possibilities for a media room, fitness space, playroom, or potential fifth bedroom. Step outside to your own private retreat featuring a saltwater pool with water features, covered lanai, fenced backyard, and the added privacy of no rear neighbors. Thoughtful enhancements throughout the home include the custom family room built-in with electric fireplace, decorative ceiling beams, engineered hardwood flooring in the primary suite and office, permanent exterior architectural trim lighting, a whole-home security camera system, overhead garage storage, newer kitchen appliances, a new microwave, a newer pool pump, and spray foam insulation for enhanced energy efficiency. Residents enjoy resort-style amenities including a clubhouse, community pool, playground, and dog park, all just minutes from Hamlin Town Center, top-rated schools, shopping, dining, major highways, and Walt Disney World. Blending timeless design, quality craftsmanship, and an unbeatable location, 5513 Thomas Square Drive is a rare opportunity to own a truly move-in-ready home in the heart of Winter Garden.

5513 Thomas Square Drive, 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
$650,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Great house fronting the park, gym, and community pool. Tons of upgrades inside and out. Beautiful screened pool with motorized shade for privacy on patio. Saltwater pool. Luxury Vinyl Plank throughout the house. NO Carpet! Kitchen has lots of upgrades as well. KitchenAid appliances. Wall oven and cooktop. Samsung refrigerator included. Washer and Dryer also stay! 5 mounted TV's will convey as well! Ring alarm system with cameras as well. Plantation shutters throughout.

14048 Lake Abbotts Drive, Winter Garden
$810,000
5 Beds ⋅ 4 Baths ⋅ Signature Lakes SubDv. ⋅ 34787 Zip Code
Welcome to this exceptional 5-bedroom, 3 full bathroom and 1 half bathroom two-story home located in the highly desirable Signature Lakes at Independence community of Winter Garden. Offering approximately 3,438 square feet of thoughtfully designed living space, this residence showcases a perfect blend of modern upgrades, elegant finishes, and exceptional indoor and outdoor living. The home was fully renovated and modernized in 2024 with high-quality materials carefully selected for the owners’ personal enjoyment and long-term use. The inviting open-concept floor plan features beautiful flooring, custom lighting throughout, upgraded details, a spacious family room, formal dining area, and flexible spaces ideal for a home office, media room, or additional entertainment area. The modern kitchen offers beautiful cabinetry, ample storage, and a functional layout designed for everyday living and entertaining. Additional features include customized closets, a complete laundry room, and a whole-house water filtration system. The washer and dryer will convey with the sale. Enjoy the ultimate Florida lifestyle with a large private screened-in pool area featuring a pool approximately 30x14 and a separate spa approximately 8x8, creating the perfect setting for relaxing, entertaining, and enjoying year-round outdoor living. The home also features a covered outdoor living area and outdoor kitchen space. Major improvements include two air conditioning systems replaced in 2023 and 2024, a Tesla electric vehicle charger, and an additional EV charger compatible with other electric vehicles. The custom lighting throughout the home will remain, including the one-of-a-kind natural stone chandelier at the staircase, a truly unique statement piece designed specifically for the residence. The spacious primary suite offers a private retreat with an upgraded spa-inspired bathroom and elegant finishes, while additional bedrooms provide comfort and flexibility for family members and guests. Located in Signature Lakes at Independence, residents enjoy resort-style amenities including a clubhouse, community pools, fitness center, parks, playgrounds, sports courts, and scenic walking trails. Conveniently located near Hamlin Town Center, shopping, dining, entertainment, major highways, and Walt Disney World attractions, this beautifully upgraded Winter Garden residence offers the perfect combination of luxury, comfort, and community lifestyle. Please note: curtains do not convey with the sale. Buyer and buyer’s agent are encouraged to verify all measurements, HOA information, restrictions, fees, and community requirements.

14418 Avenue Of The Rushes, Winter Garden
$859,000
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 3b SubDv. ⋅ 34787 Zip Code
RARE FIND! Experience resort-style living in this exceptional home on a rare OVERSIZED 0.15-acre homesite, ideally located JUST MINUTES from the vibrant HAMLIN Town Center in one of Winter Garden's most desirable areas. Featuring a stunning nearly NEW HEATED SALTWATER PRIVATE POOL, premium summer kitchen, expansive covered lanai, elegant travertine patio, and a fully fenced backyard, this property offers the Florida lifestyle today's buyers are looking for. Offering 2,990 square feet, 4 spacious bedrooms, and 2.5 bathrooms, this home perfectly blends luxury, comfort, energy efficiency, and everyday functionality. Designed with flexibility in mind, it also features a versatile flex room with the potential to serve as a future fifth bedroom, home office, or study, as well as a spacious upstairs bonus room ideal for a media room, playroom, or additional family living space. The primary suite is complemented by an oversized walk-in closet. The fully fenced backyard is a true private retreat designed for entertaining and relaxing year-round. The nearly new heated saltwater pool was built with all required permits, offering the confidence and peace of mind that come with a recently constructed, modern pool system. Outdoor living is completed by the covered lanai and travertine deck, a premium summer kitchen, and low-maintenance artificial turf. A convenient first-floor half bathroom with direct access to the backyard makes entertaining even more enjoyable. Beyond its outdoor living spaces, this home also delivers a remarkable financial advantage. The FULLY PAID-OFF SOLAR PANEL SYSTEM, valued at over $30,000, means no lease or loan to assume and helps keep the average monthly electric bill at approximately $80, even during Florida's summer months. That's hundreds of dollars in energy savings every month, providing exceptional long-term value and sustainability for the next homeowner. Additional upgrades include a beautifully remodeled upstairs bathroom with a frameless glass shower enclosure, custom closet systems, two independent HVAC systems for enhanced comfort and efficiency, professionally installed gutters, an epoxy-coated garage floor, and overhead garage storage racks. The location adds even more value: just minutes from Hamlin Town Center, with convenient access to top-rated schools, Publix, Walmart, restaurants, cafés, boutique shopping, Cinépolis Luxury Cinemas, PopStroke, Urban Air Adventure Park, and SR-429. As a resident of the highly desirable Summerlake community, you'll enjoy standout amenities, including a clubhouse, fitness center, community pool, tennis courts, playgrounds, walking trails, and lawn maintenance included through the HOA. Move-in ready and thoughtfully upgraded throughout, this home offers a rare combination of outdoor living, energy efficiency, and prime Winter Garden location. Schedule your private showing today! All information, including room dimensions, square footage, HOA fees, community amenities, and restrictions, is deemed reliable but not guaranteed and should be independently verified by the buyer and buyer’s agent.

7594 Lake Hancock Boulevard, Winter Garden
$1,249,990
5 Beds ⋅ 4 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code
Virtually Staged. Modern architecture. Total effortlessness. This five-bedroom residence is a masterclass in high-end finish designs, featuring high ceilings, iron-rod accents, and a dramatic, gallery-inspired aesthetic. At its heart, a chef-caliber kitchen serves as the ultimate hub for refined entertaining. Step into a home where luxury meets thoughtful innovation. This sprawling corner-lot property, crafted by the renowned Meritage Homes, is a rare find that perfectly balances grand proportions with everyday comfort. Boasting five spacious bedrooms, three full baths, and two half baths, the layout is designed for those who love to host and move freely through their space. The heart of the home is an expansive, sun-drenched open floor plan that flows effortlessly toward your own private oasis. Step outside to find a beautiful screened-in pool area, ideal for afternoon swims or evening gatherings without the worry of the elements. What truly sets this residence apart is the commitment to quality and efficiency. Protected by a timeless tile roof, the home features high-energy windows and spray-foam attic insulation, keeping the interior cool. The oversized three-car garage even comes equipped with a Tesla charger, ready for your electric vehicle. From the numerous high-end upgrades found throughout the interior to the curb appeal of its prominent corner position, every detail has been considered. This is more than just a house; it’s a modern, energy-efficient sanctuary built for a lifestyle. The experience extends to a private pool house, complete with a game room and a theater-style loft. Outside, the pool anchors an at home retreat. This is luxury without the logistics. Your residency is entirely turnkey and ready for you to move in.

1734 Amsel Falls Park Terrace, Winter Garden
$589,000
4 Beds ⋅ 2 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to Wintermere—where comfort, privacy, and location come together in one exceptional home. Nestled on a quiet cul-de-sac within the desirable gated Wintermere community, this beautifully maintained 4-bedroom, 2-bath residence offers an ideal blend of indoor and outdoor Florida living. The open split-bedroom floor plan is filled with natural light and features soaring ceilings, spacious living areas, and an updated kitchen complete with a large center island, stainless steel appliances, generous cabinetry, and abundant counter space overlooking the main living area—perfect for everyday living and entertaining. The private primary suite offers a relaxing retreat with dual vanities, a spacious walk-in closet, a garden tub, and a separate shower. Step outside to your own backyard oasis featuring a saltwater pool, expansive lanai, and oversized fenced backyard situated on a generous 0.31-acre lot. Whether you’re hosting family gatherings, enjoying quiet evenings by the pool, or simply taking advantage of Florida’s year-round sunshine, this outdoor space was designed to be enjoyed. Additional highlights include an indoor laundry room, two-car garage, extended driveway, mature landscaping, and the security of a gated neighborhood with sidewalks throughout. Ideally located just minutes from Winter Garden Village, Hamlin Town Center, Walt Disney World, SR-429, Florida’s Turnpike, shopping, dining, hospitals, major employers, and highly regarded schools, this home offers exceptional convenience while maintaining a peaceful residential setting. If you’ve been searching for a move-in ready pool home in one of Winter Garden’s most sought-after gated communities, this property is one you won’t want to miss. Saltwater pool! Screened lanai! Cul-de-sac! Gated community Split floor plan Open concept! Stainless steel appliances! Center island! Fenced backyard! No rear neighbors! Move-in ready! Winter Garden Close to Disney Near Winter Garden Village Near Hamlin Easy access to SR-429 & Florida’s Turnpike Ask about the Incentives that you may QUALIFY FOR!!!

2031 Wintermere Pointe Drive, Winter Garden
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