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 beautifully blends small-town warmth with modern conveniences. Known for its picturesque landscapes and vibrant community, Winter Garden is a hidden gem just a short drive from the bustling attractions of Orlando. The historic downtown area, with its quaint shops, delightful eateries, and the scenic West Orange Trail, invites residents and visitors alike to explore its unique offerings.

For those seeking a home that epitomizes the Florida lifestyle, look no further than the stunning residences with private pools found throughout Winter Garden. Imagine stepping into your backyard oasis, where you can unwind under the sun, host lively summer barbecues, or enjoy tranquil evenings by the water. These homes are designed for both relaxation and entertainment, featuring spacious layouts, contemporary finishes, and lush landscaping that enhances the beauty of your outdoor retreat.

Living in Winter Garden means enjoying year-round sunshine and access to a wealth of recreational activities. From the nearby lakes and parks to the numerous golf courses and community events, there’s always something to do. Families will appreciate the highly-rated schools and safe neighborhoods, making it an ideal place to raise children.

Whether you're looking for a cozy bungalow or a luxurious estate, Winter Garden's homes with private pools offer a perfect blend of comfort and leisure. Dive into the lifestyle you've always dreamed of and discover why Winter Garden is the perfect place to call home!

Newest Winter Garden Homes with Private Pool type

15023 Guava Bay Drive, Winter Garden
$835,000
5 Beds ⋅ 4 Baths ⋅ Watermark Ph 4a SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully 2021-built home offering 4 bedrooms, 3.5 bathrooms, and versatile living spaces designed for modern Florida living! The first floor features tile flooring, a dedicated den ideal for a formal dining room, home office, or playroom, a welcoming family room, and a guest suite. Upstairs, a spacious bonus room provides additional flexibility for a media room, game room, or secondary living area. Step outside to your private, screened-in, heated swimming pool and covered lanai, perfect for relaxing, entertaining, and enjoying Florida’s year-round outdoor lifestyle with a view of Disney fireworks on your backyard. Additional highlights include a 2-car garage with epoxy flooring, an Universal EV charger, and an outdoor summer kitchen. Located in a growing Central Florida area, this home offers an opportunity to enjoy today’s lifestyle while keeping an eye on the area’s future development, including planned residential, commercial, and infrastructure projects that continue to shape the region. Conveniently located near the SR 429 exit toward Tampa, this home in the desirable Watermark community offers easy access to major roadways and every convenience. Across the street is the highly regarded Panther Lake Elementary with the HorizonWest High School right next door, walking distance. Enjoy the proximity with the The Mark, that features a pharmacy, gas station, Starbucks, and restaurants only a mile way. Nearby is the Hamlin Town Center's shopping, dinning, entertainment, brand new Library,and the nearby parks and recreational amenities. This property offers a wonderful combination of convenience, lifestyle, and accessibility.

15023 Guava Bay Drive, Winter Garden
726 Regina Circle, Oakland
$695,000
5 Beds ⋅ 4 Baths ⋅ Johns Landing Ph 01 44/47 SubDv. ⋅ 34787 Zip Code
Welcome to 726 Regina Circle in Oakland, Florida! This spacious two-story home offers five bedrooms, four bathrooms, and an inviting layout designed to accommodate a variety of living needs. The interior features vaulted ceilings, a formal dining area, and comfortable living spaces, including a family room with a fireplace. The kitchen offers granite countertops, a breakfast bar, an island, and ample cabinetry, creating a functional space for everyday living and entertaining. The primary suite features an en-suite bathroom with dual vanities and a separate soaking tub and shower. Step outside to enjoy the private swimming pool and outdoor space, ideal for relaxing or entertaining guests. A two-car garage provides additional parking and storage. Conveniently located in the Oakland and Winter Garden area, the property offers access to nearby shopping, dining, parks, trails, and major roadways. Schedule your private showing and discover the possibilities this home has to offer.

726 Regina Circle, Oakland
8270 Topsail Place, Winter Garden
$849,900
4 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Luxury Single-Story Pool Home in Lakeshore Preserve | 4BR/3BA | Disney Fireworks Views Enjoy luxury living in this heavily upgraded Toll Brothers home in Lakeshore Preserve, featuring a private pool with a brand new pool heater, no rear neighbors, and views of Magic Kingdom fireworks. The light-filled, open floor plan features 12-foot ceilings, 8-foot doors, and upscale lighting throughout the kitchen, dining area, and great room. The gourmet kitchen offers upgraded cabinetry, a butler’s pantry, quartz countertops, stainless steel appliances, a built-in wall oven, and an impressive 12-foot center island. The owner’s suite overlooks the pool and includes two walk-in closets and a spa-style bathroom with dual vanities and a frameless glass shower. The flexible layout includes a dedicated office with a closet that can serve as the fourth bedroom, a private guest suite with an ensuite bathroom and walk-in closet, and a third full bathroom off the hall. Outside, your backyard retreat awaits with a private pool, extended screened lanai, and oversized covered patio pre-plumbed for a summer kitchen. Take in peaceful sunrise views and enjoy Magic Kingdom fireworks after dark. Lakeshore’s resort-style amenities include a lakefront clubhouse, event room, fitness and yoga rooms, meditation room, zero-entry community pool with splash features, summer kitchen, sand volleyball, dock, trails, playgrounds, parks, fire pit, dog park, and kayak launch. Dining, shopping, schools, golf, and area attractions are just minutes away. HOA includes Wi-Fi and lawn care. Minutes to dining, shopping, schools, golf, and area attractions. Available for immediate occupancy; contact for a private showing.

8270 Topsail Place, Winter Garden
816 E Fullers Cross Road, Winter Garden
$1,150,000
4 Beds ⋅ 4 Baths ⋅ Crown Point Town SubDv. ⋅ 34787 Zip Code
Rare gated, custom-built home on an oversized 1.28-acre lot within the Winter Garden golf cart district. This property is a dream for an investor or family planning for a multi-generational property. The primary residence is over 3000 sq. ft with 4 bedrooms, 3.5 bathrooms and a two-car garage. Additionally, it includes a permitted pad for a four-car garage, which currently serves as both a basketball court and an outdoor entertainment area perfect for hosting large gatherings. The original plat had 6 houses, and the current layout would be ideal for adding an ADU. Buyer to contact city for permitting/building regulations. Finding property near downtown Winter Garden or close to the West Orange Trail with space to play a game of soccer, football, or volleyball in the front or back yard is nearly impossible. The property is fully fitted with a saltwater pool, raised bed gardens, tire swing, and other outdoor amenities. It's perfect for the green thumb with a litany of fruiting trees and shrubs. This is a once in a generation opportunity to customize a lot-set home with country-style living adjacent to one of the most desirable downtown districts in Orlando. Roof 2018, AC units 2025 & 2026, Hot Water Heater 2021.

816 E Fullers Cross Road, Winter Garden
13618 Larsen Lane, Winter Garden
$888,000
4 Beds ⋅ 4 Baths ⋅ Glynwood Ii SubDv. ⋅ 34787 Zip Code
Virtually Staged. A true pride-of-ownership home showcasing architectural elegance, extensive upgrades, and the ultimate Florida lifestyle! Welcome to this stunning Winter Garden residence featuring a freshly painted exterior, tropical landscaping, paver driveway, and spacious three-car garage. Inside, soaring 13.5-foot ceilings, architectural arches, double-tiered tray ceilings, and a custom coffered family room ceiling create an impressive atmosphere. The gourmet kitchen features a sprawling granite island with prep sink, 42-inch solid wood cabinetry custom-painted in November 2025, premium GE Profile stainless steel appliances, a cooktop, double ovens, and a separate butler’s pantry ideal for entertaining or a coffee station. Enjoy seamless indoor-outdoor living through 16-foot, four-panel sliding pocket doors opening to a spacious brick-paver, screened lanai. Relax beneath the covered patio with flush-mounted speakers or beside the oversized saltwater pool with a new variable-speed pump installed in October 2025. The private quarter-acre backyard features mature privacy hedging and a convenient pool-access bathroom with a glass-enclosed walk-in shower. The main-level primary suite offers an elegant tray ceiling, a custom walk-in closet system installed in February 2026, and luxury linen and blackout window treatments. More than $100,000 in reported premium upgrades enhance comfort, efficiency, and peace of mind. Improvements include a 2-ton Daikin 15.6 SEER2 HVAC system (September 2025), upgraded R-38 attic insulation (September 2025), zoned 5-ton variable-speed Trane HVAC. Whole house hot water hybrid system: Tankless water heater fed by propane tank as a main source (electric tank can be used as a back-up). Aquasure Harmony whole-house water softener (August 2024), and a roof replaced in August 2016. Smart-home features include pre-wired 7.1 family room surround sound, multi-zone audio, window-tint film, security cameras with hybrid DVR, motion-activated lighting, smart front-door and garage locks, smart thermostats, and a Rachio irrigation controller. The gated subdivision adds another layer of appeal. Located in desirable Glynwood II at StoneCrest, residents enjoy a clubhouse, resort-style pool, playground, tennis courts, and scenic walking trails with pond views, a fountain, and green spaces. Conveniently close to Winter Garden Village, shopping, dining, parks, and the West Orange Trail, the community also offers access to major roadways, Orlando’s employment and entertainment centers, world-famous theme parks, Orlando International Airport, and Florida’s beautiful beaches. Experience exceptional architecture, modern technology, privacy, and effortless entertaining in this remarkable Winter Garden home! Note: The last four photos have been virtually staged.

13618 Larsen Lane, Winter Garden
900 Allendale Lane, Oakland
$1,799,000
4 Beds ⋅ 5 Baths ⋅ Oakland Parkb-2 SubDv. ⋅ 34787 Zip Code
Beautifully crafted by J&J Building, this exceptional 4-bedroom, 4.5-bath custom home combines thoughtful design, elegant finishes, and effortless indoor-outdoor living. Situated on a desirable corner lot, the home is filled with incredible natural light and offers a layout designed for both everyday comfort and entertaining. At the heart of the home, the stylish kitchen is complemented by a wet bar and a full scullery (back kitchen) with a second refrigerator, oven, sink and built-in pantry, creating the perfect blend of style and functionality. The main-level primary suite provides a private retreat, while three additional upstairs bedrooms each feature their own en-suite bathroom, offering comfort and privacy for family and guests alike. The downstairs office and upstairs loft area also provide flexible options to meet all your needs. The oversized attic storage with drop down stairs is perfect for all your seasonal items! Step outside to your own private oasis through the huge pocketing sliding glass doors, and enjoy the salt water pool, spa, and inviting outdoor living space with automated retractable screens—ideal for enjoying Florida living year-round. And the large garage has 2 EV plugs and 2 garage doors- 1 perfect for your golf cart! Just across the street, a beautiful pond provides a peaceful natural backdrop, with scenic sunset views and abundant wildlife adding to the home's special setting. Enjoy an exceptional lifestyle just steps from the West Orange Trail and within the Golf Cart District, offering convenient access to downtown Winter Garden's charming shops, restaurants, and vibrant community atmosphere. A rare opportunity to enjoy custom craftsmanship, beautiful surroundings, and an unbeatable location—all in one remarkable home.

900 Allendale Lane, Oakland
725 Tranquil Trail, Winter Garden
$669,000
5 Beds ⋅ 3 Baths ⋅ Black Lake Park Ph 02 SubDv. ⋅ 34787 Zip Code
Enjoy the best of Winter Garden living in this inviting pool home, ideally situated in the desirable gated community. Located in a premier area close to shopping, dining, entertainment, and everyday conveniences, this home combines spacious interiors, welcoming curb appeal, and a backyard made for enjoying the Florida lifestyle. A striking exterior, tropical landscaping, and a covered front entry create a memorable first impression. Inside, abundant natural light, soft interior colors, and attractive flooring lend warmth to the main living spaces. The thoughtfully arranged two-story layout offers room to gather, entertain, and unwind, with a welcoming front living area and an open kitchen, dining, and family room that keep the heart of the home connected. The kitchen is a standout, featuring wood cabinetry, stainless steel appliances, recessed lighting, and a generous contrasting island topped with a light countertop. Ample cabinet storage and expansive work surfaces provide both style and practicality, while the adjoining dining area offers a comfortable setting for everything from casual breakfasts to holiday gatherings. Large windows and sliding glass doors brighten the surrounding living spaces and connect the interior to the backyard. Upstairs, a spacious loft adds valuable flexibility to the floor plan. Create a second lounge, media room, play area, or workspace tailored to your needs. The generously sized primary bedroom provides a relaxing retreat with room for a sitting area, while the additional bedrooms give versatility for guests, hobbies, or working from home. Step outside to discover one of the home’s most appealing features: a private backyard retreat with a swimming pool, raised spa, and an expansive paver deck. Spend sunny afternoons poolside, enjoy outdoor dining, or gather with friends beneath the evening sky. Privacy fencing, surrounding greenery, and lawn space complete this inviting setting, bringing together room for recreation and relaxation. This community enhances the lifestyle with gated entry and community amenities that include a swimming pool, playground, sports courts, and a community boat ramp and dock. Beyond the neighborhood, enjoy convenient access to Winter Garden Village’s shopping and restaurants, historic downtown Winter Garden, and major roadways connecting you to Orlando and Central Florida’s attractions. With its bright living spaces, flexible layout, appealing kitchen, and beautiful poolside setting, this home offers an exceptional combination of comfort and convenience in a sought-after Winter Garden location. Schedule your private showing.

725 Tranquil Trail, Winter Garden
234 N Lakeview Avenue, Winter Garden
$2,199,900
5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to The Birdhouse, one of Downtown Winter Garden's most iconic residences. Situated just blocks from Plant Street, the West Orange Trail, and the shores of Lake Apopka, this remarkable property offers a rare opportunity to own a thoughtfully restored home that seamlessly blends timeless architecture with modern luxury. Set on an expansive and highly coveted 0.51-acre lot, The Birdhouse delivers an unrivaled combination of character, sophistication, and downtown living. Originally built in 1920, this meticulously restored home preserves its historic charm through exposed brick walls, wood-beamed ceilings, vintage glass doorknobs, original lighting fixtures, multiple fireplaces, beautifully maintained hardwood floors and more. Natural light pours through original diamond-pane windows into the spacious family room, while the formal living and dining rooms showcase timeless character and thoughtful custom details. The chef's kitchen is a true focal point with a distinctive mix of old-world charm and modern design that combine luxury and function. Features include Cambria Portrush quartz countertops, custom floor-to-ceiling cabinetry, premium ZLINE appliances with an 8 burner gas stove range below exposed brick walls, a statement tile backsplash and custom range hood. Floating wood shelves, an expansive breakfast bar and cozy breakfast nook with built-in seating complete its design. A spacious mudroom and custom laundry room offer extensive cabinetry and counterspace for both storage and everyday convenience and a dedicated home office includes a custom built in desk. Set apart from the living areas and secondary bedrooms, the newly designed primary suite serves as a private sanctuary. Accessed through its own hallway, this spacious retreat features vaulted wood-paneled ceilings, an enormous walk-in closet, and a spa-inspired bath with dual vanities, two private water closets, a large glass-enclosed shower and elevated finishes throughout. Four additional generously sized bedrooms provide exceptional flexibility, including a second primary suite with dual closets and an ensuite bath, an additional ensuite bedroom overlooking the pool, and two bedrooms with a full guest bath positioned in between. The enormous fully fenced backyard is designed for year round enjoyment with a gas-heated saltwater sport pool, outdoor kitchen, expansive brick paved deck, detached covered lanai, and low-maintenance turf. Towering above it all is one of the property's most extraordinary features: a majestic 390-year-old oak tree, recognized as the oldest recorded oak tree in Orange County, providing unparalleled beauty and shade. Equally noteworthy, the home's original exterior waterspout remains in place and fully operational, offering a unique connection to the property's storied past. A double carport includes both a Tesla and golf cart charging station as well as a large storage closet equipped with power and a shop desk. Recent home improvements include a new roof (May 2026), updated PVC plumbing and drain field, new air handler, new tankless hot water heater, new water filtration system and new structural support trusses installed beneath the home to enhance long-term stability and strengthen the property's foundation for generations to come. A rare blend of historic significance, modern luxury, and premier location, The Birdhouse represents one of Downtown Winter Garden's most exceptional residential offerings. Schedule your private viewing today!

234 N Lakeview Avenue, Winter Garden
324 E Fullers Cross Road, Winter Garden
$520,000
3 Beds ⋅ 2 Baths ⋅ Magnolia Wood Third Addition SubDv. ⋅ 34787 Zip Code
Welcome to this inviting 3-bedroom, 2-bath home in the desirable Winter Garden Golf Cart District. NEW ROOF to be completed by the end of October. Situated on a 0.40 acre, fully fenced lot with a electric gated entrance. This property offers space, privacy, and plenty of opportunities to enjoy the Florida lifestyle. Relax by the private pool, entertain guests on the screened lanai, or enjoy the ample backyard space with gorgeous oak trees. This home features two living spaces, offering ample room and a wood-burning fireplace. An enclosed under-air back porch provides extra space for a den, office, or loft. Two storage sheds with electricity offer convenient room for tools, equipment, and outdoor essentials. Save on irrigation with the dedicated well. Conveniently located near shopping, dining, parks, and major roadways, this home combines outdoor living with everyday convenience in the heart of Winter Garden. Don't miss this opportunity to enjoy the space, features, and location this property has to offer!

324 E Fullers Cross Road, Winter Garden
1947 Bay Clover Drive, Winter Garden
$650,000
5 Beds ⋅ 4 Baths ⋅ Carriage Pointe SubDv. ⋅ 34787 Zip Code
Gated Community Immaculate 5 bedrooms, 4 baths with cathedral ceilings, triple sliding doors that sits on a Private Oasis on a Premium Corner Lot with no Rear Neighbors. Lots of privacy includes a salt water swimming pool for leisurely days and elegant outdoor entertaining. Versatile space for the entire family, guests or a dedicated home office. Full en suite on the 2nd floor. Home offers the flexibility to complement a variety of lifestyles. Enjoy the opportunity to make this inviting residence your own and experience the comfort, space and outdoor Florida Lifestyle worth discovering. Call to schedule your appointment today. Florida Living at Its Finest.

1947 Bay Clover Drive, Winter Garden
17839 Gourd Neck Loop, Winter Garden
$925,000
7 Beds ⋅ 4 Baths ⋅ Verde Park Ph 2 SubDv. ⋅ 34787 Zip Code
Elegant pool residence in Winter Garden’s Verde Park, minutes from the Turnpike. This impeccably maintained 7-bedroom, 4-bath home offers 4,704 square feet of refined living space, a 3-car tandem garage, and a 0.24-acre lot with no community homes behind it. Multiple living and entertaining areas and a versatile floor plan offer exceptional flexibility for everyday living and hosting in a sought-after location. Step inside to a formal living room on one side of the entry and a formal dining room on the other. The living room is a flexible space that easily serves as a home office, library, sitting room, or whatever suits your lifestyle. At the heart of the home, the gourmet kitchen showcases quartz countertops, a tile backsplash, stainless steel appliances including a cooktop and double wall oven, crown-molded cabinetry with under-cabinet lighting, and a pantry. It opens to the family room, creating an inviting setting for daily living and entertaining. Tile flooring extends throughout the first floor, and a separate breakfast nook overlooks the pool. The downstairs primary suite is a private retreat with its own French doors to the pool area. The en suite bath features dual vanities, a soaking tub, a walk-in shower, and a generous walk-in closet with custom built-in organizers. An additional first-floor bedroom and adjacent full bath offer a comfortable option for guests, and the bath doubles as a convenient pool bath with direct access to the outdoors. Quartz countertops grace all four bathrooms. Upstairs, an expansive loft provides room for a second family room, game area, or gathering space. A separate media room with double doors is a dedicated space for movie nights, complete with a projection screen and projector that convey. Five additional bedrooms and two full bathrooms complete the second floor, with laminate flooring throughout the loft and bedrooms. Outside, your private backyard retreat features a sparkling 35x12 saltwater pool and a covered paver patio, designed to make the most of Florida living, whether you’re enjoying a quiet afternoon poolside or entertaining friends and family. The location is hard to beat. Just 5 minutes to Florida’s Turnpike, within walking or biking distance of the West Orange Trail, and minutes from shopping including Costco, dining, and Montverde Academy. With its thoughtfully designed floor plan, multiple entertaining areas, and convenient location, this exceptional home is ready to welcome its next owners. Schedule your private showing today.

17839 Gourd Neck Loop, Winter Garden
14807 Winter Stay Drive, Winter Garden
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code
Welcome to 14807 Winter Stay Drive, a beautifully upgraded luxury residence located in the heart of Horizon West in Winter Garden. Spanning 3,856 square feet of refined living space on an oversized lot, this 5-bedroom, 4-bathroom home combines upscale comfort, privacy, and resort-style living. The outdoor sanctuary is custom-built for the Florida lifestyle, featuring a fully fenced backyard, a heated saltwater pool and spa, a spacious covered lanai with retractable awnings, and scenic sunset views overlooking the prestigious Orange County National Golf Course. Inside, the open-concept layout flows effortlessly for everyday living and grand entertaining. The gourmet kitchen boasts premium appliances, upgraded finishes, and an expansive quartz center island. The primary suite offers a private retreat with a spa-inspired bathroom, complemented by custom closets and a dedicated drop zone for extra organization. Upstairs, a large bonus room provides flexible space for a home theater, media room, or executive office, while an oversized 3-car garage offers generous vehicle and storage space. Value-adding upgrades include an owned solar panel system to significantly reduce energy costs. Situated just 0.5 miles from The Mark Plaza and minutes from Horizon West Hospital, top-rated dining, and shopping, this home offers fast access to SR 429, Florida’s Turnpike, and Walt Disney World. Schedule your private tour today.

14807 Winter Stay Drive, Winter Garden
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