Winter Garden Homes with Pool Amenities

Winter Garden Homes with Pool Amenities

Welcome to Winter Garden, Florida, a charming city that beautifully blends small-town warmth with modern conveniences. Nestled just west of Orlando, Winter Garden boasts a rich history and a vibrant community atmosphere that attracts families, retirees, and everyone in between. With its picturesque downtown area, complete with brick-paved streets, boutique shops, and delightful dining options, it’s no wonder that Winter Garden is a sought-after destination for those looking to call Florida home.

One of the standout features of Winter Garden is its stunning selection of homes, many of which come with sought-after pool amenities. Imagine stepping out of your back door to a private oasis where you can soak up the sun, host barbecues, or simply relax by the water's edge. Homes with pool amenities in Winter Garden offer the perfect retreat after a long day, providing a serene environment for family gatherings or quiet evenings under the stars.

In addition to the beautiful homes, Winter Garden is known for its outdoor recreational opportunities. With numerous parks, scenic trails, and access to the West Orange Trail, residents enjoy an active lifestyle surrounded by nature. The community also hosts various events throughout the year, fostering a strong sense of belonging among neighbors.

Whether you’re seeking a cozy family home with a pool or a luxurious estate for entertaining, Winter Garden has something for everyone. Embrace the Florida lifestyle and discover your dream home in this delightful city, where every day feels like a vacation!

Newest Winter Garden Homes with Pool Amenities

$877,766
5 Beds 5 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Located off the family room is a den with French doors perfect for work or play and a powder room. Customize this area to meet your needs with an optional bedroom and full bathroom. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11887 Shine View Lane, Winter Garden

$798,391
4 Beds 3 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Bellmore. This all concrete block constructed, one-story layout features 4 bedrooms and 3 bathrooms. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a spacious walk in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom. This home features a space to fit all your needs. Like all homes in Waterleigh, the Bellmore includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11893 Shine View Lane, Winter Garden

$823,176
5 Beds 5 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Located off the family room is a den with French doors perfect for work or play and a powder room. Customize this area to meet your needs with an optional bedroom and full bathroom. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11905 Shine View Lane, Winter Garden

$833,771
5 Beds 5 Baths Harvest At Ovation SubDv. 34787 Zip Code
Under Construction. What's Special: Corner Lot | Game Room | Dedicated Study. New Construction - December Completion! Welcome to the Cumberland at 15993 Honey Harvest Street in Harvest at Ovation! Discover a thoughtfully designed home where style and functionality come together. The welcoming foyer leads into an open-concept living space featuring a spacious great room, dining area, and gourmet kitchen, creating the perfect setting for everyday living and entertaining. Pocket sliding glass doors in the great room open to an expansive covered lanai, blending indoor and outdoor living. Privately situated just off the dining area and kitchen, the primary suite offers a spacious bathroom with dual sink vanities, an oversized shower, and a walk-in closet. At the front of the home, you'll find a secondary bedroom, a full bathroom, and a convenient half bathroom. Upstairs, three additional bedrooms, two full bathrooms, and a versatile game room provide plenty of space for relaxation and recreation. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: study, tray ceiling package, a shower in bathroom 3, pocket sliding glass door, 8' interior doors, laundry room sink, and outdoor kitchen rough-in. Virtually staged photos are for representative purposes only. MLS#O6431045

15993 Honey Harvest Street, Winter Garden

$784,991
5 Beds 4 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Cresswell. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find a flex room perfect for work or play and downstairs powder room. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Customize the second floor of this home to create a space that meets your needs but transforming the loft area to a fifth bedroom with full bath or Guest Suite with ensuite bathroom. Like all homes in Waterleigh, the Cresswell includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11911 Shine View Lane, Winter Garden

$812,285
4 Beds 5 Baths Harvest At Ovation SubDv. 34787 Zip Code
Under Construction. What's Special: Corner Lot | Dedicated Study | Oversized Garage | Gourmet Kitchen. New Construction – December Completion! Built by America's Most Trusted Home Builder. Welcome to the Saint Clair at 12940 Harvest Rain Avenue in Harvest at Ovation! This spacious single-story home offers a thoughtfully designed open-concept layout centered around an impressive great room that flows seamlessly into the dining area and gourmet kitchen with a large island. The private primary suite features a luxurious bathroom and generous walk-in closet. Three secondary bedrooms, a dedicated study, and multiple full bathrooms provide flexibility for work, guests, or hobbies. Direct access to the laundry area through the convenient drop zone just off the two-car garage provides added convenience. Enjoy indoor-outdoor living with the expansive lanai, perfect for relaxing or entertaining. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights include: Tray ceiling package, whole house 8' interior doors, study in place of flex, deluxe primary bathroom, outdoor kitchen rough-in, cushion close doors and drawers kitchen cabinet package, and whole house blinds. Photos are for representative purposes only. MLS#O6430978

12940 Harvest Rain Avenue, Winter Garden

$985,000
4 Beds 4 Baths Oakland Park South SubDv. 34787 Zip Code
LAKE APOPKA VIEWS FROM THE UPSTAIRS BALCONY. DIRECT ACCESS TO THE WEST ORANGE TRAIL. GOLF CART RIDES TO DOWNTOWN WINTER GARDEN. OVERSIZED THREE-CAR GARAGE. FENCED BACKYARD ADDED IN 2025. CUSTOM PRIMARY CLOSET SYSTEM. CUSTOM BACKYARD DECK. PLANTATION SHUTTERS THROUGHOUT. LOW-MAINTENANCE OUTDOOR SPACE. Start the morning with coffee on the upstairs balcony overlooking Lake Apopka, spend the afternoon biking or walking the West Orange Trail, and take the golf cart into Downtown Winter Garden for dinner, the farmers market, or an evening on Plant Street. Located in Oakland Park, this RockWell Homes Lincoln floor plan offers spacious living with a layout designed for both everyday life and entertaining. The builder included quartz countertops, luxury vinyl plank flooring, and a covered lanai. The primary suite features a custom closet system designed to maximize storage and organization. The oversized three-car garage provides plenty of room for vehicles, storage, bikes, golf carts, and recreational equipment, and the garage floor has been finished with a durable epoxy coating. The owners have also added plantation shutters throughout, a custom backyard deck, French drains to improve drainage around the property, and a fenced backyard completed in 2025. The backyard has no grass to water or mow, creating an easy-to-maintain outdoor space while still providing privacy and room to relax or entertain. Oakland Park is connected to the West Orange Trail and positioned between Oakland and Historic Downtown Winter Garden. Residents can easily enjoy Plant Street’s restaurants, shops, farmers market, community events, and the surrounding golf cart district, all while coming home to a quieter neighborhood setting with views of Lake Apopka.

1234 Canyon Creek Trail, Winter Garden

$290,500
3 Beds 2 Baths Southern Pines Condo SubDv. 34787 Zip Code
Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden

$937,281
4 Beds 4 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Seacliff. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room. Customize this area to meet your needs with an optional den. Go down the hallway and you’ll find a powder room and laundry room tucked behind the stairwell leading up to the second floor. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and a walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with separate vanities, shower/tub space, toilet room with privacy door as well as a spacious walk in closet. As we head upstairs, you are greeted with a loft area and all three bedrooms. Two bedrooms share a upstairs bathroom with double bowl vanity while the additional bedroom is complete with ensuite bathroom. Like all homes in Waterleigh, the Seacliff includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11833 Shine View Lane, Winter Garden

$615,000
4 Beds 3 Baths Stoneybrook West SubDv. 34787 Zip Code
Stoneybrook West is situated amongst great schools, restaurants, shopping, is near the 429, Turnpike, 408, historical downtown Winter Garden and of course the theme parks. The HOA INCLUDES lightning speed fiber optic SPECTRUM INTERNET AND CABLE, access to the Olympic-sized COMMUNITY POOL, splash pad, clubhouse with FITNESS CENTER, basketball, pickleball and tennis COURTS, a community BOAT RAMP with LIMITED BOAT STORAGE and a FISHING PIER. This home sits in the quiet Masthead Landing neighborhood with charming curb appeal. Upon entry you’ll be greeted by the spacious foyer and beautiful staircase. FRENCH DOORS lead to the PRIVATE OFFICE with abundant sunlight. There’s plenty of space for the family to relax and entertain between the formal living and dining rooms and the family room open to the kitchen. The PICTURE WINDOW provides an unobstructed POND VIEW. The eat-in kitchen has a WALK-IN PANTRY plus a closet pantry, GRANITE countertops, tile backsplash, and stainless-steel appliances. Convenience awaits in the spacious LAUNDRY ROOM with a utility sink, storage, dryer and NEW WASHING MACHINE (2025). The primary bedroom upstairs has the beautiful POND VIEW, laminate flooring, a walk-in closet with built-in shelving, a garden tub and RENOVATED SHOWER. The secondary bedrooms share the hall bathroom. Outside you’ll find a spacious SCREENED PATIO and a 2-car garage with storage racks. Interior features include a half bath downstairs, BUILT-IN SPEAKERS and MOTORIZED SHADES in the living room, touch-sensitive kitchen faucet, ceiling fans, fantastic storage, new closet doors in one bedroom, impact windows in the primary bedroom and new toilets throughout. Exterior features include LIGHTNING RODS and GUTTERS. NEW WINDOWS were installed in 2019/2022, the roof was replaced in 2017, and the water heater was replaced in 2018. This home is ready and waiting for you!

14827 Masthead Landing Circle, Winter Garden

$769,076
4 Beds 3 Baths Waterleigh SubDv. 34787 Zip Code
Under Construction. Waterleigh presents the Bellmore. This all concrete block constructed, one-story layout features 4 bedrooms and 3 bathrooms. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a spacious walk in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom. This home features a space to fit all your needs. Like all homes in Waterleigh, the Bellmore includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11923 Shine View Lane, Winter Garden

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