Winter Garden Homes with Private Pool type

Winter Garden Homes with Private Pool type

Welcome to Winter Garden, Florida—a charming city nestled in the heart of Orange County that perfectly blends small-town warmth with modern conveniences. Known for its picturesque landscapes and vibrant community spirit, Winter Garden boasts a rich history that dates back to the early 1900s. Today, it’s a thriving hub for families, retirees, and everyone in between, offering a delightful mix of outdoor activities, shopping experiences, and cultural events.

One of the standout features of Winter Garden is its stunning array of homes, particularly those with private pools. Imagine stepping out into your own backyard oasis, where you can soak up the sun, host lively barbecues, or simply unwind after a long day. Homes with private pools in Winter Garden are designed for both relaxation and entertainment, providing the perfect setting for creating cherished memories with family and friends.

The community is also home to several beautiful parks and recreational facilities, making it easy to enjoy the Florida sunshine. Whether you’re exploring the scenic West Orange Trail, visiting the historic downtown area with its quaint shops and eateries, or attending one of the many local festivals, you’ll find that Winter Garden offers a vibrant lifestyle that caters to all interests.

With its friendly atmosphere, excellent schools, and proximity to Orlando’s attractions, Winter Garden is not just a place to live; it’s a place to thrive. Discover your dream home with a private pool in this enchanting city and experience the best of Florida living!

Newest Winter Garden Homes with Private Pool type

$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
$850,000
5 Beds ⋅ 3 Baths ⋅ Covington Chase Ph 2b SubDv. ⋅ 34787 Zip Code
Virtually Staged. Beautiful five-bedroom, three-bath pool home located in the highly sought-after Golf Cart District of Downtown Winter Garden. Situated on a spacious, fully fenced corner lot, this home offers a versatile floor plan with room to live, work, and entertain. Upon entry, a flex room is located to the right and may be used as an office, playroom, sitting room, or study. A formal dining room is located to the left. The main living area features an open-concept kitchen, living room, and dinette area. A downstairs bedroom and full bath provide a convenient option for guests or multigenerational living. Upstairs, the primary suite includes two walk-in closets. Three additional bedrooms, a full bath, and the laundry room are also located upstairs. The large media room offers flexible use as a theater room, home office, game room, or bonus space. Enjoy the private outdoor area with a covered porch, fully fenced yard, and saltwater pool and spa. Upgrades include freshly painted interior and exterior, and new carpet installed on 7/23/26. The AC unit is one year old. The seller will pay off the solar system at closing, providing added energy-efficiency benefits for the next owner. Conveniently located near the West Orange Trail, Plant Street Market, local shopping, dining, parks, and Downtown Winter Garden. Golf cart is available for purchase separately and is not included in the sale of the home.

637 Grassy Stone Drive, Winter Garden
$1,030,000
4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!

13852 Jomatt Loop, Winter Garden
$755,000
3 Beds ⋅ 3 Baths ⋅ Winding Bay Ph 3 SubDv. ⋅ 34787 Zip Code
Beautifully upgraded home in the highly desirable Winding Bay community! 3-bedroom, 2.5-bath + office/flex room one-story single-family home over 2,100 square feet of comfortable living space with modern finishes and an open floor plan filled with natural light. The spacious kitchen is truly the heart of the home, featuring a large quartz island, built-in oven and microwave, gas cooktop, stainless steel appliances, plenty of cabinet space, and a walk-in pantry.  Master Bedroom Suite offers a spa-like bathroom with dual vanities, a large walk-in shower, and a custom walk-in closet. The dedicated office with built-in cabinetry provides an ideal work-from-home space. The backyard offers your own private retreat with a heated saltwater pool, covered lanai, outdoor kitchen, pergola, and a fully fenced yard—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather year-round. Additional features include solar panels, luxury laminate flooring throughout the main living areas, a custom wood panel for the TV, a spacious laundry room with built-in cabinets and utility sink, an irrigation system, and a two-car garage with storage racks and an EV charger. Winding Bay enjoy resort-style amenities including a community pool, playground, dog park, and scenic walking paths, all conveniently located near Disney, Horizon West, shopping, dining, and top-rated schools.

15009 Lebeau Loop, Winter Garden
$1,150,000
5 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code
Welcome to 9225 Holliston Creek Place, an exceptional pool home nestled on a premium corner lot in one of Winter Garden's most sought-after communities. From the moment you arrive, the lush landscaping, side-entry garage, and beautifully maintained exterior set the tone for everything this home has to offer. Step inside and you are immediately greeted by soaring ceilings, an abundance of natural light, and a thoughtfully designed open floor plan that flows seamlessly from the formal living and dining areas into the heart of the home. The spacious kitchen is a true entertainer's dream, featuring generous counter space, ample cabinetry, and a layout that opens directly to the main living area — perfect for gatherings of any size. The dedicated home office is one of the standout features of this property — large, well-appointed, and completely separate from the living spaces, giving you the ideal work-from-home setup or the flexibility to use as a fifth bedroom, playroom, or media room. The primary suite is a private retreat, offering a generous layout, spa-like en suite bathroom with dual vanities, soaking tub, and walk-in shower. Secondary bedrooms are well-sized and thoughtfully positioned for privacy. Step outside and discover your own backyard oasis. The screened pool and lanai area is designed for true Florida living — whether you are taking a morning swim, hosting a weekend cookout, or simply unwinding at the end of the day. The summer kitchen is fully equipped and perfectly positioned to make outdoor entertaining effortless, with everything you need just steps from the pool deck. Being on a corner lot provides additional yard space, extra privacy, and enhanced curb appeal that interior lots simply cannot match. Located in a vibrant, well-established Winter Garden community with easy access to top-rated schools, SR-429, the 408, shopping, dining, and all of Central Florida's best attractions — this one truly checks every box.

9225 Holliston Creek Place, Winter Garden
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