Winter Garden Homes with Pool

Winter Garden Homes with Pool

Nestled in the heart of Florida, Winter Garden is a charming city that offers a perfect blend of small-town charm and modern amenities. Located in the sunny state of Florida, Winter Garden boasts a vibrant community with a rich history and a thriving real estate market.

For those looking to enjoy the warm Florida weather, homes with pools are a popular choice in Winter Garden. Imagine coming home to your own private oasis where you can relax, unwind, and enjoy the sunshine all year round. Whether you're looking for a cozy bungalow or a spacious family home, Winter Garden offers a variety of options for homes with pools to suit your lifestyle and budget.

With top-rated schools, scenic parks, trendy shops, and delicious dining options, Winter Garden has something for everyone. Whether you're a young professional, a growing family, or a retiree looking for the perfect place to settle down, Winter Garden is a city that truly has it all. Experience the best of Florida living in Winter Garden, where homes with pools are just the beginning of the many amenities this city has to offer.

Newest Winter Garden Homes with Pool

no property photo
$880,000
5 Beds ⋅ 4 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Enjoy spacious living, no rear neighbors, and Disney fireworks views in the sought-after Watermark community of Winter Garden! Built by Meritage Homes, this Maison floor plan offers 5 bedrooms, 3.5 bathrooms, and approximately 3,359 square feet of thoughtfully designed living space. A paver driveway and covered front porch create a welcoming first impression, leading into a foyer that opens to the second floor. The main level features a separate dining room and an open kitchen with a center island, pantry, and butler’s pantry. The kitchen connects seamlessly to the spacious family room, creating an inviting setting for everyday living and entertaining. A downstairs bedroom provides flexibility for guests or a home office, with a half bathroom conveniently nearby. Step outside to the covered lanai and enjoy the added privacy of having no rear neighbors, along with views of Disney fireworks. Upstairs, the spacious primary suite features two walk-in closets and an ensuite bathroom with dual vanities, a soaking tub, and a separate shower. Three additional bedrooms and two full bathrooms provide ample space, while the game room offers a versatile area for movies, hobbies, or relaxation. An upstairs laundry room adds everyday convenience, and the two-car garage provides parking and storage. Watermark offers an exceptional collection of resort-style amenities, including a swimming pool with a splash pad, clubhouse, fitness center, tennis courts, playground, park, and outdoor amphitheater. The community’s second-story viewing deck provides another inviting spot to enjoy Disney fireworks. Located in Winter Garden’s desirable Horizon West area near sought-after schools, this home offers convenient access to Hamlin’s shopping, dining, and entertainment, Walt Disney World, and SR-429. Discover a home that brings together generous living space, a versatile floor plan, and outstanding community amenities. Schedule your private showing today!

10079 Austrina Oak Loop, Winter Garden
17126 Quicksilver Avenue, Winter Garden
$525,000
4 Beds ⋅ 3 Baths ⋅ Waterside On Johns Lake - Phase 2c SubDv. ⋅ 34787 Zip Code
Welcome home to this beautifully cared-for 4-bedroom, 3-bathroom home in the welcoming Waterside community! Built in 2022, the thoughtfully designed floor plan, spacious backyard, and wonderful neighborhood amenities combine to create the perfect blend of comfort, functionality, and everyday family living. Inside, the OPEN-CONCEPT living space flows effortlessly into the kitchen, creating a comfortable gathering place for family time, entertaining, and everything in between. The kitchen features beautiful Silestone QUARTZ COUNTERTOPS, stylish gray cabinetry, and stainless steel appliances. The spacious primary suite offers a HUGE WALK-IN CLOSET, while the primary bathroom features a double-sink vanity and large WALK-IN TILED SHOWER. A bedroom conveniently located downstairs adds incredible flexibility and can easily serve as a guest room, home office, playroom, or a space for visiting family and friends. Throughout the home, you'll find thoughtful upgrades including plantation shutters, built-in features, 9-foot ceilings, and a beautiful wrought-iron stair railing. Situated on an OVERSIZED CORNER LOT, the property features a large fenced-in backyard with plenty of room to play, relax, or gather with friends. The back paver patio is perfect for weekend barbecues and outdoor entertaining, while the covered front porch provides a welcoming spot to enjoy your morning coffee or unwind at the end of the day. Waterside Residents enjoy access to a community clubhouse, pool, fitness center, playgrounds, park, and a dock on Johns Lake. With seasonal community events and monthly food truck nights, there are plenty of opportunities to get to know your neighbors and enjoy everything the community has to offer. Conveniently located near Downtown Winter Garden, Hamlin, and Walt Disney World, you'll be close to a fantastic selection of restaurants, shops, and entertainment. Easy access to FL-429 and the Florida Turnpike makes commuting and exploring Central Florida a breeze. Come see why this home and community are such a wonderful place to put down roots, make memories, and call home!

17126 Quicksilver Avenue, Winter Garden
no property photo
$853,626
5 Beds ⋅ 5 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
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.*

11815 Shine View Lane, Winter Garden
14031 Zephermoor Lane, Winter Garden
$800,000
5 Beds ⋅ 3 Baths ⋅ Windward Cay 48 125 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Beautifully renovated 5-bedroom, 3-bath pool home located in gated Windward Cay! This move-in-ready 3,007 sq. ft. home has been thoughtfully updated with high-end finishes throughout, including a renovated kitchen and bathrooms and new luxury vinyl flooring. All major mechanicals have been updated, including the roof (2023), both AC units (2024 and 2026), and water heater (2025). When you enter the home, you are greeted by a gorgeous open space with views straight to the pool through a wall of oversized glass sliding doors. To the left and right, you have bonus spaces that can be used as an office, gaming area, or hangout space. To the right is a large dining room, flooded with natural light. At the foot of the staircase, there is a large storage space that is currently being used as a fun play area to spark imagination. Beyond the dining room is the open family room and renovated kitchen, featuring new hardwood cabinets, quartz countertops, plenty of storage, and a large island that keeps you connected to your guests while you watch the big game! Just beyond the family room, you'll find a large bedroom with a Murphy bed and great storage, next to a full bath, giving guests their own private space and access to the pool area! Upstairs, we have the remaining four bedrooms. The carpet, hallways, and stair spindles are all brand new. The spacious primary suite features a spa-like ensuite with a soaking tub and luxurious walk-in shower, along with two large closets and luxury vinyl flooring. Oversized windows bring in excellent natural light, while the high ceilings, crown molding, and tray ceilings add to the home's open and inviting feel. The other bedrooms are spacious and bright, with a large renovated bathroom featuring dual sinks and new finishes. Outside, enjoy the Florida lifestyle with a screened-in heated salt water pool and spa, perfect for relaxing or entertaining. The home also offers a 3-car garage and sits on approximately a quarter-acre lot. This home also features a water softener and central vacuum. Located in the gated community of Windward Cay, this home is close to Winter Garden's shopping, dining, entertainment, and major roadways

14031 Zephermoor Lane, Winter Garden
1316 Southern Sun Drive, Oakland
$1,050,000
5 Beds ⋅ 4 Baths ⋅ Hull Island SubDv. ⋅ 34787 Zip Code
A private screened porch off the primary bedroom, views of the natural surroundings and thoughtfully enhanced outdoor spaces define the appeal of this Hull Island at Oakland residence. Built in 2022, the five-bedroom, four-full-bath home offers 3,658 square feet of living area according to current public records, with two levels designed for both gathering and retreat. The open kitchen and family-room layout connects everyday living with entertaining, complemented by solid-surface counters, a range and range hood. Upstairs, a versatile loft provides space for a media lounge, reading area or workspace. The primary bedroom opens to its own screened porch overlooking nature—an inviting setting for morning coffee or a quiet evening. Custom closet built-ins add a tailored touch and practical organization. A full bathroom on the first floor adds convenience. Outside, the rear patio features pavers, a screen enclosure and a covering that protects from rain, creating another comfortable place to unwind or host. A front porch and attached garage complete the home’s practical appeal. The Oakland setting adds an outdoor dimension to daily life, with area destinations including the West Orange Trail and Oakland Nature Preserve, where trails and a boardwalk showcase the Lake Apopka landscape. Experience a home that balances generous interior spaces, personal retreats and a connection to the outdoors. Arrange a private showing to appreciate the setting and layout in person. Included with the sale: washer, dryer, range, microwave, refrigerator, security cameras, smart door lock and window blinds.

1316 Southern Sun Drive, Oakland
12355 Bracco Street, Winter Garden
$565,000
4 Beds ⋅ 3 Baths ⋅ Highland Rdg Ph 2 SubDv. ⋅ 34787 Zip Code
Virtually Staged. STUNNING 2024-BUILT HOME ON AN OVERSIZED LOT IN ONE OF WINTER GARDEN’S DESIRABLE GATED COMMUNITIES! Why wait to build when you can enjoy the benefits of nearly new construction in this beautiful 4-BEDROOM, 3-BATHROOM HOME offering modern living, exceptional curb appeal, and an OVERSIZED LOT that provides extra space to enjoy the Florida lifestyle! Built in 2024, this impressive home offers the comfort, style, and peace of mind that come with newer construction. With four spacious bedrooms and three full bathrooms, there is plenty of room for comfortable everyday living, entertaining guests, or creating the perfect home office. The oversized lot is a standout feature, offering additional outdoor space with endless possibilities for entertaining, relaxing, gardening, or creating your own backyard paradise! LOCATION, LOCATION, LOCATION! Welcome to beautiful WINTER GARDEN, one of Central Florida’s most sought-after destinations! Discover why so many people love calling this incredible area home. Enjoy the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for its incredible restaurants, boutique shopping, lively farmers market, and vibrant community atmosphere. Explore the scenic WEST ORANGE TRAIL, enjoy nearby parks and recreational opportunities, and take advantage of fantastic shopping, dining, entertainment, and convenient access to Orlando’s world-famous attractions! RESORT-STYLE COMMUNITY AMENITIES WITHOUT THE HIGH HOA FEES! Enjoy the added appeal of a GATED COMMUNITY featuring a beautiful COMMUNITY SWIMMING POOL and PLAYGROUND, all while benefiting from LOW HOA FEES! It’s a wonderful combination of community amenities, convenience, and affordability. With its 2024 CONSTRUCTION, FOUR BEDROOMS, THREE FULL BATHROOMS, OVERSIZED LOT, GATED COMMUNITY, COMMUNITY POOL, PLAYGROUND, AND PRIME WINTER GARDEN LOCATION, this home offers an incredible opportunity to enjoy the Florida lifestyle! DON’T MISS YOUR OPPORTUNITY TO CALL THIS BEAUTIFUL PROPERTY HOME! SCHEDULE YOUR PRIVATE SHOWING TODAY AND DISCOVER EVERYTHING THIS EXCEPTIONAL HOME AND COMMUNITY HAVE TO OFFER!

12355 Bracco Street, Winter Garden
14501 Grove Resort Unit 1723, Winter Garden
$344,900
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
THE PERFECT COMBINATION AT THE GROVE RESORT! TOWER 1. TOP FLOOR. CORNER UNIT. LAKE AUSTIN & NATURE PRESERVE VIEWS. PLUS, ENJOY MAGIC KINGDOM & EPCOT FIREWORKS FROM YOUR PRIVATE PRIMARY SUITE SOLARIUM! Welcome to Unit 1723, a beautifully positioned 3-bedroom, 3-bathroom condo-hotel residence with a solarium, offering 1,544 sq. ft. of comfort, convenience, and breathtaking scenery at The Grove Resort & Water Park. LOCATION MAKES ALL THE DIFFERENCE! Situated on the 7th and highest floor of Tower 1, this desirable corner residence combines beautiful water and nature preserve views with the convenience of the resort's main building. Enjoy easy access to the lobby, concierge, restaurant, bar, and fitness center without leaving your tower. Inside, discover an inviting open-concept living and dining area, a fully equipped kitchen, spacious bedrooms, and a private solarium sitting area off the primary suite, where you can gather with family to watch the Magic Kingdom and EPCOT fireworks. Direct balcony access from the primary suite, a full-size in-unit washer and dryer, and ample resort parking add everyday convenience. Just minutes from Walt Disney World, The Grove is a designated Walt Disney World Good Neighbor® Hotel, featuring Surfari Water Park with its FlowRider® Surf Simulator, lazy river, swimming pools, hot tubs, on-site dining, recreational activities on Lake Austin, and resort transportation to Disney and Universal theme parks. Whether you're looking for a Florida vacation retreat or a professionally managed short-term rental opportunity, Unit 1723 offers an exceptional blend of location, comfort, memorable views, and resort living. This condo-hotel property is subject to resort rental and occupancy restrictions and is not intended for permanent residency. Buyers should verify all applicable association and resort requirements.

14501 Grove Resort Unit 1723, Winter Garden
14501 Grove Resort Avenue Unit 2539, Winter Garden
$163,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium 1 SubDv. ⋅ 34787 Zip Code
BEST-PRICED UNIT CURRENTLY AVAILABLE AT THE GROVE RESORT! This 5th-floor Birch residence is located in desirable Tower 2, the newest tower at The Grove and featuring the resort's most updated décor and finishes. Enjoy a peaceful garden view from this fully furnished resort residence just minutes from Walt Disney World. The Grove Resort & Water Park offers an exceptional combination of vacation ownership and resort amenities, including Surfari Water Park, multiple pools, restaurants and bars, fitness center, spa, arcade, Lake Austin activities, market and coffee shop, and on-site resort management. An outstanding opportunity for buyers looking for an entry point into one of Orlando's most established condo-hotel resorts at the best price currently offered. Financial information and ownership details available upon request.

14501 Grove Resort Avenue Unit 2539, Winter Garden
15411 Gilligan Court, Winter Garden
$539,900
4 Beds ⋅ 3 Baths ⋅ Winding Bay Ph 1b SubDv. ⋅ 34787 Zip Code
Located in Horizon West, this 4-bedroom, 2.5-bath home features a first-floor bedroom, private outdoor entertaining space, and no carpet throughout. Set within Winding Bay and zoned for top-rated schools, the community offers parks, a playground, walking trails, a dog park, and a resort-style pool with a splash pad. Just minutes from Walt Disney World, residents enjoy nightly fireworks views and convenient access to Highway 429, Hamlin Town Center, Flamingo Crossings, premier golf courses, and a wide variety of dining and shopping destinations. No CDD. Low HOA.

15411 Gilligan Court, Winter Garden
9936 Pallida Hickory Way, Winter Garden
$468,000
3 Beds ⋅ 3 Baths ⋅ Watermark SubDv. ⋅ 34787 Zip Code
Virtually Staged. Location, location, location! paid off solar system! Beautifully maintained home in the highly sought-after Watermark community, offering exceptional amenities and a prime location backing onto a highly rated high school, with NO rear residential neighbors. Enjoy Carpet-Free living with brand-new flooring installed in 2026, plus a lovely balcony perfect for relaxing. Your new home awaits—schedule your showing today!

9936 Pallida Hickory Way, Winter Garden
1396 Roxy Lane, Winter Garden
$499,900
4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lake Ph 2c SubDv. ⋅ 34787 Zip Code
Welcome home to Waterside on Johns Lake, a highly sought-after community in Winter Garden! This 4-bedroom, 3-full-bath, 2,030 sq. ft. single-family home offers an open-concept floor plan with a great blend of functionality and living space. The first floor features the great room that flows seamlessly into the dining area and kitchen, which features 42-inch grey shaker cabinetry, quartz countertops, and a pantry. Also on the first floor is a full bathroom and a bedroom, making it ideal for guests, a home office, or flexible living needs. A convenient mudroom with generous storage provides additional functionality. Step outside to a private patio with a dedicated seating and entertaining area, along with a large fenced-in side yard. The rear of the property features a detached 2-car garage and a private driveway with additional parking for two vehicles. Upstairs, the split-bedroom layout provides privacy and flexibility. The spacious primary suite features an oversized bedroom, walk-in closet, and private en-suite bathroom. Two additional bedrooms, a third full bathroom, and a dedicated laundry room complete the second floor. The location is hard to beat, with convenient access to Winter Garden Village, Hamlin, Horizon West, Downtown Winter Garden, and SR-429. Enjoy an easy drive to Central Florida's major attractions, including Disney, SeaWorld, and Universal Studios, as well as an abundance of shopping, dining, and entertainment options. Waterside on Johns Lake features resort-style amenities including a community pool and clubhouse, playground, park, fitness center, and community dock on Johns Lake. The home is also zoned for highly regarded A-rated schools, including Hamlin Elementary, Hamlin Middle, and West Orange High.

1396 Roxy Lane, Winter Garden
14791 Field Daisy Drive, Winter Garden
$531,055
3 Beds ⋅ 3 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Dedicated Study | Close to Amenities | Flat Lot. New Construction - January Completion! Welcome to the Ashwood at 14791 Field Daisy Drive in Harvest at Ovation! This beautiful new home blends open-concept living with flexible spaces for today’s lifestyle. The inviting foyer leads to a private study, while the spacious great room flows seamlessly into the kitchen featuring a large island and walk-in pantry. Enjoy indoor-outdoor living with the covered lanai just off the main living area. Upstairs, the private primary suite offers a relaxing retreat with a generous bathroom and walk-in closet, while two secondary bedrooms sharing a full bathroom, and a laundry room are nearby. 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: 8' interior doors, single exterior door at kitchen, oak treads and painted risers, sink at laundry room, and whole house blinds. Photos are for representative purposes only. MLS# O6447800

14791 Field Daisy Drive, Winter Garden
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