Winter Garden Homes with Pool Community Features

Winter Garden Homes with Pool Community Features

Welcome to Winter Garden, Florida – a picturesque city nestled in the heart of Orange County. Known for its charming downtown area and vibrant community spirit, Winter Garden is a delightful blend of small-town warmth and modern conveniences. With scenic parks, beautiful lakes, and a rich history, this city offers a tranquil lifestyle just a stone's throw from the bustling attractions of Orlando.

One of the highlights of living in Winter Garden is the abundance of homes with pool community features. Imagine stepping out of your back door to a sparkling pool, perfect for warm Florida days spent soaking up the sun or hosting gatherings with family and friends. These communities are designed for comfort and leisure, providing residents with a resort-style living experience right at home.

Winter Garden's homes with pool community features often come complete with lush landscaping, spacious backyards, and access to amenities such as clubhouses, fitness centers, and walking trails. Whether you’re looking for a cozy single-family home or a more expansive property, the real estate options here cater to a variety of lifestyles and budgets.

Beyond the beautiful homes, Winter Garden boasts a thriving arts scene, farmer's markets, and a variety of dining options that showcase the local flavor. With easy access to major highways and the nearby attractions of Orlando, residents enjoy the perfect balance of serene living and urban excitement. Discover the charm of Winter Garden – where your dream home with a pool awaits!

Newest Winter Garden Homes with Pool Community Features

1388 Waverunner Lane, Winter Garden
$515,000
4 Beds ⋅ 3 Baths ⋅ Waterside On Johns Lake - Phase 2c SubDv. ⋅ 34787 Zip Code
1% INTEREST RATE BUYDOWN for the first year, or up to a $6,000 Lender Credit—available through our preferred lender! UPGRADED CORNER LOT HOME IN THE CHARMING WATERSIDE COMMUNITY! Built in 2021, this 4 bedroom, 3 bathroom home features a thoughtfully designed floor plan, spacious fenced-in outdoor patio and backyard, and upgrades throughout. You are greeted by a welcoming covered front porch, the perfect spot to enjoy your morning coffee. Stepping inside, the OPEN-CONCEPT living space features wood-look tile flooring which flows effortlessly into the dining room and kitchen, creating a comfortable gathering place for family time and entertaining. The dining room has an ADDED BUILT-IN BAR area with dual-zone wine fridge, evergreen fog cabinets, butcher block countertop, and stylish backsplash. The kitchen features beautiful Silestone QUARTZ COUNTERTOPS, clean white cabinetry, under-cabinet lighting, and stainless-steel appliances, including an upgraded dishwasher (2024). Accentuating the bright kitchen are updated black pendant lights and handles. A bedroom conveniently located downstairs features a tasteful SHIPLAP accent wall, and adds incredible flexibility, easily serving as a guest room, home office, or playroom. Upstairs, the spacious primary suite offers a huge CUSTOM WALK-IN CLOSET, while the primary bathroom features a double-sink vanity and large WALK-IN TILED SHOWER. There are two spacious guest bedrooms upstairs that share their own separate bathroom, with its own shiplap feature wall, double sink vanity, and separate wet area for maximum convenience. Throughout the home you'll find additional thoughtful upgrades, including built-in desk and cabinets in the upstairs landing area, 9-foot ceilings, and a beautiful wrought-iron stair railing. Situated on a CORNER LOT, the property features a large wrought iron FENCED-IN backyard with plenty of room to play, relax, or gather with friends. The large back paver patio has an added SHADE SAIL, allowing for year-round enjoyment in the wonderful Florida weather. Community of Waterside residents enjoy access to a community clubhouse, pool, fitness center, two 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, plus top-rated schools and hospitals. Easy access to FL-429 and the Florida Turnpike makes commuting and exploring Central Florida a breeze. Set up your private showing of this updated home today!

1388 Waverunner Lane, Winter Garden
15543 Kinnow Mandarin Lane, Winter Garden
$648,000
3 Beds ⋅ 3 Baths ⋅ Highlands/Summerlake Grvs #1 SubDv. ⋅ 34787 Zip Code
Discover the best of Horizon West living in this beautifully maintained home nestled in the sought-after Highlands at Summerlake Groves in Winter Garden! Offering 3 bedrooms, 2.5 bathrooms, and a spacious open-concept design, this inviting residence blends modern comfort, thoughtful features, and exceptional indoor-outdoor living. Step inside to light-filled living spaces and an airy atmosphere that welcomes you home. The beautifully appointed kitchen features elegant quartz countertops, abundant cabinetry, and stainless steel appliances, opening seamlessly to the spacious great room, an ideal setting for entertaining or enjoying everyday moments. Walk upstairs to impressive high ceilings that adds to the home's open and spacious feel. The generous primary suite provides a peaceful retreat, complete with a walk-in closet and an en-suite bathroom featuring a relaxing Jacuzzi tub. The three additional generously sized bedrooms are conveniently located upstairs, offering guests and family members added privacy and comfortable personal space. This well-designed layout provides the perfect balance of togetherness and privacy for everyone to enjoy. Enjoy the added ease of natural gas service, 1 Gbps high-speed internet for streaming, working, and staying connected, and an attached two-car garage featuring a high-profile garage door and built-in storage shelving. Another appealing feature is the average monthly electric bill of approximately $150–$200, depending on usage and season. Take your Florida lifestyle outdoors in the private backyard retreat, where an inviting outdoor summer kitchen and natural gas fire pit create the perfect setting for weekend gatherings, evening relaxation, and entertaining family and friends. Both the outdoor kitchen and fire pit are plumbed directly to the home's natural gas supply for added convenience. Beautifully upgraded landscaping further enhances the home's curb appeal and outdoor setting. The Highlands at Summerlake Groves offers an outstanding array of community amenities, including a swimming pool, two tennis courts, dog park, two playgrounds, soccer field, and picnic areas with grills. Ideally situated near Orange County National Golf Center, Hamlin Town Center, shopping, restaurants, grocery stores, Orlando Health Hospital, major roadways including the 429, and local schools. Walt Disney World and the area's many attractions are also just a short drive away. With its desirable location, inviting living spaces, natural gas outdoor entertaining features, and wonderful community amenities, this home offers an exceptional opportunity to enjoy the very best of Winter Garden living. Come see all this beautiful home has to offer!

15543 Kinnow Mandarin Lane, Winter Garden
12818 Sunset Walk, Winter Garden
$659,008
4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. New Construction by Toll Brothers in Winter Garden’s Horizon West! Estimated completion in early 2027. Don't miss the opportunity to show your clients this beautiful corner-unit townhome! A welcoming covered entry leads into a thoughtfully designed, spacious living area featuring a dedicated dining space, gourmet kitchen with breakfast bar, and inviting great room with access to a private courtyard, perfect for relaxing or entertaining. The spacious primary suite offers a generous walk-in closet and a private ensuite bathroom featuring dual vanities, a separate shower, and a private water closet. Experience the quality, style, and thoughtful design of Toll Brothers in one of Winter Garden's desirable locations!

12818 Sunset Walk, Winter Garden
16431 Olive Hill Drive, Winter Garden
$560,000
3 Beds ⋅ 3 Baths ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome Home to this immaculately maintained 3-bedroom, 3-bathroom two-story home located in the highly desirable Hawksmoor in Winter Garden. This home offers paid off solar and 240 outlet for EV charging. As you walk up you will take note of charming front porch perfect for sipping morning coffee. As you enter the foyer you will notice flex/office/den with French doors and ceramic tile throughout with thoughtfully designed interior. The homes first floor is perfect for entertaining with open concept kitchen family room with oversized dinette. The kitchen has a large center island with plenty of seating, stainless steal appliances, granite counters and water filtration system that overlooks the under roof covered screened in lanai perfect for an outdoor grill and outdoor entertaining area. Upstairs, the primary suite serves as a relaxing retreat with a tray ceiling, large walk-in closet, and private bath featuring dual sinks and granite counters. The guest bath upstairs has dual sinks bath tub and granite counters. Additional upgrades include new quiet garages door, first floor, fresh exterior paint and ample storage. Residents enjoy access to fantastic community amenities including a clubhouse, resort-style pool, park, playground, and sidewalks throughout the neighborhood. Conveniently located just minutes from Hamlin Town Center, golfing, shopping, dining, entertainment, Walt Disney World, and major highways with easy access to Orlando and surrounding areas. This exceptional home combines modern upgrades, energy-efficient features, functional living spaces, and an unbeatable location. Schedule your private showing today.

16431 Olive Hill Drive, Winter Garden
14501 Grove Resort Avenue Unit 2627, Winter Garden
$194,900
3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
This stunning 3-bedroom, 3-bathroom condo-hotel in Orlando, Florida, offers the perfect blend of luxury, comfort, and convenience. Located just minutes from the world-famous theme parks, this fully furnished unit is an excellent choice for both personal use and investment. The condo features a spacious open floor plan with modern finishes, a fully equipped kitchen with stainless steel appliances, and a private balcony with breathtaking views. The master suite boasts a luxurious en-suite bathroom, while the second and third bedrooms and bath provide ample space for guests. Enjoy resort-style amenities, including a sparkling swimming pool, fitness center, full-service spa, on-site dining, concierge services, and a shuttle to major attractions. With its prime location near shopping, dining, and entertainment, this condo-hotel is an exceptional opportunity for those looking to experience the best of Orlando!

14501 Grove Resort Avenue Unit 2627, Winter Garden
373 Eron Way Unit 47, Winter Garden
$163,000
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Charming single-story townhome in Townhomes of Winter Garden featuring 2 bedrooms and 2 full baths. Interior features low-maintenance laminate flooring throughout the main living areas and bedrooms, paired with an efficient open floor plan. Conveniently located just minutes from historic downtown Winter Garden, Plant Street dining, shopping, and major commuter routes including SR-429 and the Florida Turnpike. Easy to show—schedule through Showing Time today!

373 Eron Way Unit 47, Winter Garden
10503 Spring Arbor Lane, Winter Garden
$459,000
4 Beds ⋅ 3 Baths ⋅ Winding Bay Preserve SubDv. ⋅ 34787 Zip Code
INVESTOR ALERT! Currently tenant-occupied, this beautiful 4-bedroom, 3-bath townhome offers over 2,200 sq. ft. of thoughtfully designed living space in Horizon West’s Winding Bay Preserve. The open kitchen features 42-inch white cabinets, a walk-in pantry, and a large island overlooking the spacious dining and great room. French doors lead to a screened, fenced courtyard with access to the 2-car garage. A first-floor bedroom with peaceful conservation views and an adjacent full bathroom provides added flexibility. Upstairs, the spacious primary suite features a dual-sink vanity, walk-in shower, private water closet, and a generous walk-in closet with built-ins. Two additional bedrooms overlook the conservation area and share a full bathroom, while a versatile loft and conveniently located laundry room complete the second floor. Winding Bay Preserve offers a resort-style community pool, playground, and parks amid beautiful conservation surroundings. Conveniently located near shopping, dining, schools, and Central Florida’s world-renowned attractions. An excellent opportunity to add a tenant-occupied property to your investment portfolio! Contact us for lease details and showing availability.

10503 Spring Arbor Lane, Winter Garden
1370 Portmoor Way, Winter Garden
$755,000
5 Beds ⋅ 4 Baths ⋅ Stoneybrook West 44/134 SubDv. ⋅ 34787 Zip Code
Nestled within the highly desirable golf course community of Stoneybrook West in Winter Garden, this beautifully renovated 5-bedroom, 4-bathroom residence offers a perfect blend of modern finishes, spacious living areas, and exceptional Florida living. Thoughtfully updated throughout, the home features a newer roof and HVAC system, fresh interior paint, new custom kitchen and bathroom cabinetry, luxury vinyl plank flooring, new bedroom carpeting, updated lighting and ceiling fans, and a newly re-screened enclosure. At the heart of the home, the stunning remodeled kitchen showcases custom cabinetry, all new stainless steel appliances, elegant quartz countertops, designer lighting, and an oversized breakfast bar ideal for gathering and entertaining. A charming breakfast nook provides the perfect spot for casual dining while enjoying picturesque views of the golf course. The inviting living spaces are enhanced by a beautiful double-sided fireplace, creating warmth and character throughout the home. A versatile downstairs flex room and bathroom offer endless possibilities for a home office, in-law suite, or playroom. Upstairs, a loft at the top of the stairs provides additional living space for relaxing, working, or entertaining. The private primary suite serves as a peaceful retreat, featuring a generous layout, a luxurious ensuite bathroom with an oversized walk-in shower, and a private balcony overlooking the golf course—an ideal place to enjoy your morning coffee or unwind at the end of the day. Four additional bedrooms provide flexibility for family, guests, or additional workspace. The thoughtfully designed outdoor living area includes a screened pool with spa, new pool equipment and a convenient fourth bathroom with a shower accessible from the pool area, making entertaining and enjoying Florida's year-round sunshine effortless. Beyond the home, Stoneybrook West offers an exceptional lifestyle with resort-style community amenities. The HOA includes access to the Olympic-sized community pool, splash pad, clubhouse with fitness center, basketball courts, tennis courts, and pickleball courts. Residents can also enjoy the community boat ramp, and fishing pier, providing even more opportunities for outdoor recreation and relaxation. Newer Roof and HVAC. Ideally located near excellent schools, shopping, restaurants, and everyday conveniences, Stoneybrook West is guard gated and offers easy access to the 429, Florida Turnpike, and 408, as well as historic downtown Winter Garden and Central Florida's world-famous theme parks. With its extensive renovations, golf course views, private pool, and outstanding community amenities, this exceptional home offers the perfect combination of comfort, style, and location. Schedule your showing today!

1370 Portmoor Way, Winter Garden
15823 Shorebird Lane, Winter Garden
$929,900
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Discover an exceptional opportunity to enjoy the Florida lifestyle in this beautiful Toll Brothers home in the sought-after Lakeshore Preserve community of Winter Garden. Offering 4 bedrooms, 4 full bathrooms, and 2,768 square feet, this thoughtfully designed residence combines elegant interior spaces with an outdoor living experience designed for entertaining. The heart of the home is its impressive kitchen, featuring an oversized 12-foot island, gas cooktop, convection oven, and stylish finishes. Multiple living spaces and abundant natural light create an inviting atmosphere throughout. The flexible floor plan includes a first-floor bedroom and full bathroom, additional upstairs bedrooms, a private junior suite, and a spacious primary retreat featuring tray ceilings, dual walk-in closets, two vanities, a soaking tub, and a separate walk-in shower. But the real highlight is outside. Enjoy your own private saltwater pool, beautifully appointed paver deck, and summer kitchen with natural gas. Whether hosting friends, enjoying a quiet afternoon by the pool, or making the most of Florida's beautiful weather, this outdoor space makes every day feel like a getaway. Lakeshore Preserve adds even more to the experience with its lakefront clubhouse, resort-style community pool, fitness center, barbecue area, and recreational amenities. Located in Winter Garden, this home offers an appealing combination of space, thoughtful design, outdoor entertaining, and community amenities. Come experience the home and the lifestyle for yourself.

15823 Shorebird Lane, Winter Garden
6266 Sunny Time Avenue, Winter Garden
$433,890
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Dahlia interior unit townhome, a new construction home that seamlessly combines luxury and convenience. This modern townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Elkins White cabinetry, a decorative tile backsplash, quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, and gathering room is finished with elegant tile flooring. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. For added convenience from day one, this home comes complete with 2" faux wood blinds, as well as a brand new Whirlpool washer and dryer! With thoughtful design, high-end finishes, and a focus on everyday convenience, the Dahlia townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

6266 Sunny Time Avenue, Winter Garden
6367 Argent Wood Drive, Winter Garden
$449,490
3 Beds ⋅ 3 Baths ⋅ Silverleaf Oaks SubDv. ⋅ 34787 Zip Code
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! The new construction Foxtail interior unit townhome features 3 bedrooms, 2 full bathrooms, a powder room, an open concept kitchen, café and gathering room, a private courtyard, and a 2-car rear-facing garage. The first floor is ideal for entertaining, featuring a spacious gathering room, café and kitchen, with a large center island, storage pantry, white cabinetry, a decorative tile backsplash, quartz countertops, and Whirlpool stainless-steel kitchen appliances- including a refrigerator. A powder room and laundry on the first floor add to the thoughtful convenience. Enjoy entertaining loved ones from your private, fenced rear courtyard. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and en suite bathroom with a double sink quartz-topped vanity, private water closet, and a walk-in shower. Two additional bedrooms, the secondary bathroom and extra storage offered by a linen closet are on the opposite side of the second floor, offering privacy and space for everyone. Professionally curated design finishes for this popular Foxtail townhome include wood-look luxury vinyl plank flooring throughout the first floor living areas, tile flooring in the laundry room and bathroom, and soft, stain-resistant, Shaw brand carpet in the bedrooms and second floor living areas, and so much more. This new construction townhome perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind. Schedule your tour today!

6367 Argent Wood Drive, Winter Garden
13900 Lanyard Way, Winter Garden
$769,650
5 Beds ⋅ 5 Baths ⋅ Encore/Ovation-Ph 3 SubDv. ⋅ 34787 Zip Code
Short Sale. Welcome to this spacious 5-bedroom, 5-bathroom home in the desirable Encore at Ovation community in Winter Garden! Featuring a rare dual primary suite layout, this home offers an open-concept design with an upgraded kitchen showcasing a natural gas stove, oversized island, farmhouse sink, and stainless-steel appliances. The kitchen flows seamlessly into the dining and family rooms, perfect for entertaining. The first floor includes a primary suite, private den/office, and additional full bathroom. Upstairs, enjoy a versatile loft, convenient laundry room, and luxurious second primary suite overlooking the conservation area, complete with dual sinks, soaking tub, separate shower, and oversized walk-in closet. Relax on the covered back porch overlooking a private backyard with no rear neighbors. Additional features include fiber-optic internet, surround sound speakers and prewiring for security cameras. All this plus the added benefit of solar panels to help with those electricity bills. Residents enjoy resort-style amenities including a pool, fitness center, playground, dog park, and yard maintenance. Conveniently located minutes from Walt Disney World and Flamingo Crossings, offering shopping, dining, and entertainment. A rare find combining space, privacy, and an unbeatable location!

13900 Lanyard Way, Winter Garden
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