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Homes for Sale with a Pool in Winter Garden, FL

Welcome to your dedicated resource for homes for sale with a pool in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Winter Garden, FL

$529,990
3 Beds 3 Baths Waterleigh SubDv. 34787 Zip Code
Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family 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. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Cordale includes a Home is Connected 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.*

16845 Hobe Sound Court, Winter Garden

$1,270,000
5 Beds 4 Baths Hawksmoor Ph 4 SubDv. 34787 Zip Code
Come take a look at this beautiful modern elevation and spacious home. Hawksmoor community offers a luxury lifestyle nestled in Winter Garden's popular Horizon West area. This spacious home is located on the corner lot with fenced in backyard. This home offers plenty of comfort and upgraded features inside and outside. Some features in this home are the well maintained wooden floors, baseboards, backsplash features and stone countertops across the home with plenty more! The kitchen is upgraded with stainless steel kitchen aid and newer appliances alongside having a walk in pantry with cabinets all around! The open layout living room with high ceilings creates the opportunity to bring in natural light and energy to this home. The master bedroom is located on the first floor and it offers a spacious walk in closet inside the master bathroom. A powder restroom is also located on the first floor of home, game room and the laundry room with sink , washer & dryer appliances to remain. Upstairs offers four spacious bedrooms, a large family room area as well alongside Jack and Jill bathroom in between bedrooms. Finally, outside the patio is a smart screened patio where a stunning summer kitchen sits for hosting cookouts. Beautiful amenities complement the luxurious lifestyle this community boasts and include a stunning, resort-style pool, splash pad, clubhouse with outdoor summer kitchen & grill, yoga lawn, shaded playground, and network of walking trails. The community offers a gym with weight machines, dumbbells, and a few options for cardio. The clubhouse can also be rented for special events. Commuters convenience approximately minutes from the SR429. Hawksmoor convenient location within Winter Garden means dining, shopping and entertainment are never far away. Refrigerator in garage and water softener do not convey to property, all appliances are included. Call to schedule your private showing.

16894 Wingspread Loop, Winter Garden

$205,000
2 Beds 2 Baths Grove Resort And Spa Hotel Condominium SubDv. 34787 Zip Code
****Amazing opportunity to purchase a 2-bedroom/2-bathroom vacation condo at the beautiful Grove Resort in Orlando! This fully-furnished condo is very spacious, and has a full kitchen, laundry room, a screened-in balcony, and two bedrooms. There is a sleeper sofa in the living room, so it can sleep six. Buyers must enter into the onsite rental management company, who will do all the bookings, housekeeping, and maintenance for the condo. If owners want to use their condo, simply send an email and block off your desired dates. Owners can use their condo up to 179 nights per year. On site there are plenty amenities, including the Surfari Water Park, with large heated pool, lazy river, water slides, the Flowrider surfing experience, and delicious food and drinks can be purchased from the Longboard Bar and Grill. At the Springs Pools are there are three further pools and a large hot tub! Next to that you can wander down to Lake Austin and do some fishing, or paddle a swan boat! The Valencia Restaurant is a full-service venue where you can eat indoors or outdoors! A spacious 24-hour gym is also located near the Springs Pools. At the Front Desk area you will find the Marketplace, and gift shop, and the concierge who will help you with theme park tickets, restaurant bookings etc. A free daily shuttle to Disney is also available. Call now for more information!!****

14501 Grove Resort Avenue Unit 3304, Winter Garden

$796,000
5 Beds 3 Baths Oakland Trls Ph 2 SubDv. 34787 Zip Code
Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE UPGRADES—creating a home that truly feels “better than new.” Step inside to an inviting OPEN-CONCEPT LAYOUT, where the chef’s kitchen overlooks the spacious living area. Recessed lighting, NEW TILE FLOORING on the main level (2023), and ceiling fans throughout (2020) elevate the home’s comfort and style. The entire home is also PREWIRED WITH CAT 6, ideal for high-speed connectivity. The DREAM KITCHEN is a showstopper with stylish cabinetry, stone countertops, a breakfast bar, built-in oven, cooktop stove with POT FILLER, tile backsplash, walk-in pantry, and a GALLEY-STYLE COFFEE BAR AREA—perfect for morning routines or entertaining. A spacious Kitchen dinette area overlooks the backyard, adding a warm and functional touch to the heart of the home. In the Living room, enjoy a CUSTOM ACCENT WALL (2023) and views of the large backyard through dual sliding glass doors. A separate Dining room offers flexibility for family gatherings or can easily serve as a formal living room. The first floor also includes a VERSATILE OFFICE/PLAYROOM, convenient under-stair storage, and ONE OF THE FIVE BEDROOMS—complete with laminate wood flooring—located next to a full bathroom, providing a perfect space for guests or multigenerational living. Upstairs, a GENEROUS LOFT creates a perfect secondary living area. The UPDATED PRIMARY SUITE (2025) features a beautiful tray ceiling, a LUXURIOUS EN SUITE BATH with dual vanities, a step-in shower, and a huge walk-in closet. Three additional bedrooms and another full bath offer plenty of comfortable space for family and guests. A paver driveway leads to the generous 3-CAR GARAGE featuring epoxy flooring, additional kitchen-style cabinetry, and PREWIRING for an electric vehicle. Outside, enjoy a large covered patio and an EXPANSIVE BACKYARD, ideal for future customization, gatherings, or play. Oakland Trails is loved for its peaceful setting and small-town charm, offering access to the West Orange Trail, playgrounds, green spaces, and TOP-RATED SCHOOLS. Ideally positioned near DOWNTOWN WINTER GARDEN, residents enjoy quaint dining and gatherings spots, PLANT STREET MARKET, charming shops, and easy access to SR 429 for seamless commuting. Every detail has been thoughtfully crafted for ELEVATED LIVING—come experience the exceptional quality and SOPHISTICATION this home offers. Schedule your showing today!

1970 Standing Rock Circle, Oakland

$752,000
5 Beds 4 Baths Highlands/Summerlake Grvs Ph 2 SubDv. 34787 Zip Code
Welcome to your dream home in the prestigious SummerLake community, perfectly positioned on a corner lot for ultimate privacy and curb appeal. This stunning residence features fully owned solar panels, offering energy savings with no monthly payments and sustainable living at its finest. Step inside to discover spacious, integrated living areas filled with natural light, ideal for entertaining or creating cherished family moments. The main-floor bedroom with a private bath provides comfort and flexibility for guests or multigenerational living. The kitchen, equipped with stainless steel appliances and ample counter space, seamlessly connects to the dining and living areas, creating a true heart of the home. Upstairs, retreat to three carpeted bedrooms and a versatile loft, perfect for work, study, or play. One of the property’s most unique features is the private mother-in-law suite above the detached garage, accessible via its own rear entrance, offering independence and privacy for extended family, guests, or even a home office. Enjoy Florida’s beautiful weather from the screened porch, a serene outdoor escape for relaxation or entertaining. With its thoughtful layout, exceptional features, and prime location near top-rated schools, local amenities, and major highways, this home embodies the perfect combination of luxury, functionality, and Florida lifestyle. Don’t miss your chance to own this extraordinary property—schedule your private showing today and experience the ultimate in comfort and elegance!

15807 Sweet Lemon Way, Winter Garden

$2,310,600
5 Beds 6 Baths Grove At The Harvest District SubDv. 34787 Zip Code
Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floor plan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Heath Stone also features a 2-car detached garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Hearth Stone model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.

1146 Prado Lane, Oakland

$2,380,160
5 Beds 6 Baths Grove At The Harvest District SubDv. 34787 Zip Code
Pre-Construction. To be built. Introducing the Sunburst Model by Davila Homes Discover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floorplan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Sunburst also features a 3-car garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Upstairs, enjoy a stunning covered terrace, ideal for morning coffee, evening gatherings, or simply taking in the views of your surroundings. With its blend of functionality and sophistication, every space in the Sunburst is designed to make daily living both easy and elegant. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Sunburst model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.

1173 Prado Lane, Oakland

$1,574,000
4 Beds 4 Baths Lakeview Reserve 46/149 SubDv. 34787 Zip Code
COMPLETELY REMODELED WATERFRONT HOUSE WITH COVERED PRIVATE DOCK AND BOAT LIFT ON THE LARGEST LAKE IN CENTRAL FLORIDA!!! A highly energy-efficient house with owned solar panels ($30 monthly grid surcharge vs. $500-600 electric bill before). The cost of solar panels is included in the purchase price. The price can be reduced by $37K if the buyer assumes a solar panel loan at 3.49%. Experience the ultimate LAKEFRONT living with this stunning, COMPLETELY REMODELED HOUSE ($400K investment) on Lake Apopka in Winter Garden, in the heart of a highly desirable GOLF CART DISTRICT. Boasting over 3,700 sq. ft. of beautifully remodeled living space, this 4-bedroom, 3.5-bathroom residence combines modern luxury with waterfront charm. Every inch of this home has been meticulously upgraded, creating a move-in-ready oasis with high ceilings, open-concept living, designer lighting and upgraded finishes throughout. Gorgeous porcelain tile and hardwood floors flow seamlessly across two stories, complemented by abundant natural light from all-new, PANORAMIC WINDOWS. The gourmet kitchen is a chef’s dream, featuring quartz countertops, a large island with built-in cabinetry, stainless steel appliances, a backlit quartz bar, a wine fridge and a modern backsplash. Entertain effortlessly in the expansive high-ceiling dining room and living room, framing incredible LAKE APOPKA VIEWS, GORGEOUS SUNRISES AND BREATHTAKING SUNSETS! The spacious master suite on the ground floor is a serene retreat with a high ceiling, two walk-in closets, an oversized bathroom with two sinks, Jacuzzi and a massage shower and a private screened patio. Two additional bedrooms on the ground floor boast lake views, California closets and high ceilings. A second-floor oversized loft offers a full bathroom, a walk-in closet, separate HVAC and noise-reducing flooring and window treatment —perfect for another master bedroom or entertainment room. Two Florida rooms on both floors provide stunning panoramic lake views. A dedicated office/den on the ground floor is ideal for work or study. All bathrooms have windows and exhaust. Enjoy 90 feet of open-view waterfront—perfect for skiing, boating, fishing, or relaxing. The oversized COVERED BOAT DOCK has electric BOAT LIFT, lighting, WATER, and a Margaritaville-themed bar. The backyard features a RECENTLY RESURFACED SALTWATER POOL with a NEW PUMP, NEW POOL FILTER, a REFENCED PRIVATE YARD, fruit trees & mature, landscaped greenery. Additional highlights include NEW WINDOWS, HVAC, SOLAR PANELS, SMART THERMOSTAT, upgraded irrigation and landscaping, a TWO-CAR GARAGE with a lot of built-in storage and an OVERSIZED DRIVEWAY to park multiple boats or vehicles. Located in a quiet, family-friendly GATED COMMUNITY with golf-cart-friendly streets and DIRECT ACCESS to the scenic WEST ORANGE TRAIL and high-rated elementary and middle SCHOOLS NEARBY. Enjoy Winter Garden’s historic downtown just minutes away, with A-rated schools, shopping, dining, and the farmer's market. Only 20 minutes to Downtown Orlando and close to Disney, Universal, and major highways. There are 6 highly rated Golf Clubs within a 5-mile radius. This is more than a home—it’s a boater’s and fisherman’s paradise, a lakefront retreat, and a perfect family haven all in one. Don’t miss this rare opportunity to own a completely remodeled luxury waterfront home with unmatched views and lifestyle amenities on Lake Apopka, offering over 30,000 acres of endless water fun!

261 Zachary Wade Street, Winter Garden

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