Winter Garden Homes with Private Pool type

Winter Garden Homes with Private Pool type

Welcome to Winter Garden, Florida, a charming city that perfectly blends small-town warmth with modern amenities. Nestled just west of Orlando, Winter Garden boasts a rich history, picturesque landscapes, and a vibrant community spirit. With its historic downtown area filled with quaint shops, delightful eateries, and beautiful parks, residents enjoy a lifestyle that celebrates both leisure and adventure.

One of Winter Garden's most appealing features is its proximity to the stunning natural beauty of the surrounding areas, including the enchanting West Orange Trail, perfect for biking, walking, and enjoying the great outdoors. The city also hosts a variety of events throughout the year, from farmer's markets to seasonal festivals, making it easy to connect with neighbors and create lasting memories.

If you’re dreaming of a home that offers luxury and relaxation, look no further than the exquisite selection of homes with private pools in Winter Garden. Imagine stepping into your own backyard oasis, where you can unwind in the sun-drenched Florida weather or host unforgettable gatherings with family and friends. These homes not only provide a serene escape but also enhance your lifestyle, offering the perfect balance of comfort and entertainment.

With a variety of architectural styles and sizes, there’s a perfect home for everyone. Whether you’re seeking a cozy retreat or a spacious family residence, Winter Garden’s real estate market has something to suit your needs. Embrace the Florida lifestyle and make your dream of owning a home with a private pool a reality in beautiful Winter Garden!

Newest Winter Garden Homes with Private Pool type

$1,100,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to your LAKEFRONT dream home and backyard oasis! This popular “Delmar” floor plan with 120’ of DOCKABLE lake frontage on skiable Hickory Nut Lake which expends 403 acres. You will love the lake lifestyle enjoying boating, waterskiing, kayaking, or fishing! This is a great fishing lake known for it’s Largemouth bass, Bluegills, and Spotted Gars. When you’re done boating, you can finish the day in your heated swimming pool or spa. The pool and spa have all the works, including an electric AND solar heater, plus pool lights for night swimming. This home features a sizable covered lanai perfect for dining a la fresca by the pool enjoying the lake views with all the privacy having no rear neighbors. When night time comes, you will enjoy your nightly DISNEY fireworks view. A bonus of this lot is that it is pie shaped, so there is a spacious yard beside the pool that is fenced in for your furry friends. This sprawling 1 story home is located on a small alcove offering privacy from the main access road. You can sit on the covered front porch enjoying sunset views. The interior of this home is perfect for entertaining, featuring an open concept living area complete with family room/kitchen/dining combo. The stunning kitchen features a wall oven and wall microwave, cooktop, and large walk-in pantry. This “emerald series” house has all the upgrades including tile roof, custom woodwork and wainscoting, 8 ft interior doors, tray ceilings, whole house water softening system, luxury LVP all throughout (no carpets!), trim lights built into the soffit for all of your holiday lighting needs, and a new dishwasher. The exterior was hand painted in August 2026, so this is truly a turn key home! Located in the sought after Horizon West area zoned for “A” schools including Atwater Bay Elementary, Water Spring Middle School, and Horizon West High. Along with its amazing location, the Waterleigh community also offers a beautiful clubhouse with resort style pool, miniature golf course, beach volleyball, grills, picnic areas, water view, walking trails, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. Don't like mowing the lawn and weeding the shrubs? No problem, the HOA takes care of that for you here. Love the Florida golf cart life? You can take your street legal golf to the community pool, and join the neighbors for lots of fun, holiday golf cart parades!! Within minutes you have loads of shopping and activities including Hamlin center, Flamingo Crossings shopping center, and Disney parks and resorts! All you have to do is move in and start enjoying the lifestyle Waterleigh provides!

10043 Little Alcove Loop, Winter Garden
$1,460,000
5 Beds ⋅ 5 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code
Welcome to this exquisite two-story residence located in the sought-after Twinwaters community of Winter Garden. Built in 2017, this 5-bedroom, 4.5-bathroom home boasts 4,263 square feet of living space, a 3-car garage, and a private in-ground pool with a screen enclosure and outdoor kitchen. The main level features a bright open floor plan with a stone-counter kitchen/family room combo, built-in features, and primary bedroom. Upstairs offers additional bedrooms and a spacious game/recreation room. High-quality construction features concrete block and tile roof. Ideally situated with quick access to FL-429, SR-408, Hamlin Town Center, shopping, dining, and major Orlando area attractions. Schedule your private showing today!

16548 Raven Rock Place, Winter Garden
$468,000
3 Beds ⋅ 2 Baths ⋅ Oak Park At Winter Garden SubDv. ⋅ 34787 Zip Code
Located in the desirable charming golf cart community of Oak Park within a couple blocks of walking distance (or golf cart) to historical Winter Garden vibrant downtown with dining, boutique shopping and entertainment featuring a theatre and an award-winning farmers market. This well built cement block Maronda home offers a blend of charm and convenience with low HOA dues, and can be easily updated. Step out of this home into a wonderful screened heated pool and covered lanai for year-round enjoyment. The almost third acre lot is fenced on 3 sides and easily fenced and gated on each side for privacy. Within the wooded area in the back of the lot is an attractive storage shed. Veterans Memorial Park borders on the rear of the property featuring several acres of a variety of sports, including ten pickleball courts, picnic areas and playgrounds for families and pets. Hop on the scenic West Orange Trail just minutes from this home for a walk, run or bike ride. Commuting via the 429 and the Florida Turnpike gives easy access to all of Central Florida and its theme parks.

665 Stevelynn Circle, Winter Garden
$775,995
5 Beds ⋅ 3 Baths ⋅ Winter Oaks SubDv. ⋅ 34787 Zip Code
Nestled in the sought-after golf cart district just minutes from Historic Downtown Winter Garden, this spacious 5-bedroom, 3-bath smart home in Winter Oaks offers the perfect blend of comfort, style, and convenience. A rear-entry garage enhances the home's exceptional curb appeal, while the thoughtfully designed floor plan is ideal for both everyday living and entertaining. The first floor features formal living and dining rooms, a bedroom that also makes an ideal home office, a full bath, a separate laundry room, and a beautifully appointed kitchen with 42-inch cabinetry, granite countertops, stainless steel appliances, and a sunny breakfast area. Upstairs, the private primary suite provides a peaceful retreat with tray ceilings, a private balcony, an oversized walk-in closet, dual vanities, a garden tub, and a separate walk-in shower. Three additional bedrooms complete the second floor. Step outside to enjoy the fenced backyard featuring an expansive screened outdoor living area and a private plunge pool/spa, creating your own backyard oasis. Additional highlights include a new roof, tankless water heater, 16-camera security system, landscape lighting, and optional furnishings, including a baby grand piano. Residents of Winter Oaks enjoy exceptional community amenities, including a resort-style pool, playground, scenic walking trail, tranquil ponds with fountains, and a charming entrance highlighted by a restored historic water tower. Just one mile from the award-winning Winter Garden Farmers Market, Plant Street's popular shops and restaurants, the West Orange Trail, and convenient SR-429 access, this home offers an exceptional opportunity to enjoy one of Central Florida's most desirable lifestyles.

644 Autumn Oaks Loop, Winter Garden
$2,860,000
6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code
Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful Hancock Lake family friendly home is custom built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat and 2 jet skis. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, manicured gardening beds for your green thumb and plenty of room for outdoor games and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry, cabana bath and a custom salt pool showcasing a water slide, Fiber optic lighting, solar heated and whimsical Disney characters embedded in the rock’s facade. Relax to lake views, or pull down the projector screen for a movie then watch the Disney’s fireworks nightly over the lake. The home has a freshly painted exterior and interior with crown trim throughout. The Kitchen space is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating. The first level’s primary suite with patio access was previously a media room complete with surround sound that remains intact. The loft with a balcony overlooking the patio and lake is prepped for entertaining. Two additional ensuites, 3 more bedrooms and a laundry room are also on the upper level. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updated. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden
$890,000
5 Beds ⋅ 5 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code
Stunning two-story house with a permanent lake view. Be enchanted by this magnificent lakefront residence, which combines sophistication, comfort, and a privileged location. It features 5 bedrooms, 4 full bathrooms, and 1 powder room, distributed in a smart and functional layout. The social area impresses with high ceilings in the living room and sliding doors that open onto a large covered veranda, integrated with a heated pool with a safety net, ideal for leisure and entertainment throughout the year. The living room is integrated with the dining room and the spacious and elegant gourmet kitchen, equipped with a generous central island, appliances, and wooden cabinets, perfect for those who enjoy entertaining. The master suite on the ground floor offers complete privacy, as well as relaxing views of the lake and green area, and a full bathroom on the same level. On the second floor, the house also features a versatile loft, ideal for an office, TV room, or social space. The space originally intended for a garage has been carefully adapted into a private gym, and can easily be converted back to suit the new owner's needs. Located in the desirable Hawksmoor community, the property offers complete infrastructure, including a community pool, gym, clubhouse, and walking paths. All this in a strategic location, close to markets, restaurants, shops, a theater, major highways, and Disney parks. A unique opportunity to live or invest. Schedule your visit and be amazed!

16394 Taliesin Street, Winter Garden
$425,000
3 Beds ⋅ 3 Baths ⋅ Suburban Shores Rep Pt Blk 03 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Discover the potential of this spacious 3-bedroom, 3-bathroom home in Winter Garden, offering a flexible layout and plenty of room to make it your own. With 3 full bathrooms and a large flex room, this home provides endless possibilities for a home office, media room, hobby space, game room, or additional living area. The pool bathroom was added in 2018 with wheelchair-accessible features, including a zero-threshold shower and exterior ramp for ease of access. Major improvements include a metal roof (2018), whole-house generator (2017), flex room windows (2018), A/C (2013), and water heater (1999). Enjoy access to Johns Lake with a public boat ramp conveniently located at the front of the neighborhood, making it easy to spend the day boating, fishing, kayaking, or enjoying one of Winter Garden's most popular lakes. Situated with convenient access to Florida's Turnpike, Highway 50, shopping, dining, and everyday conveniences, this home offers a great opportunity for buyers looking for space, versatility, and a desirable Winter Garden location.

17531 N Sunset Terrace, Winter Garden
$1,250,000
4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code
Designed to impress and crafted for everyday living, 5513 Thomas Square Drive is a beautifully upgraded pool home in one of Hamlin's most sought-after communities. Offering 4 bedrooms, 3.5 bathrooms, a private office, an oversized loft, a versatile flex room, and a saltwater pool, this exceptional residence seamlessly blends timeless design with modern comfort. From the moment you arrive, the stone-accented elevation, oversized driveway, and manicured landscaping create unforgettable curb appeal. Inside, soaring ceilings, abundant natural light, crown molding, custom trim work, 8-foot doors, and wood-look tile flooring establish an elegant yet welcoming atmosphere. The dramatic two-story great room is the undeniable centerpiece of the home, showcasing a custom floor-to-ceiling built-in with cabinetry, open shelving, and a heat-producing electric fireplace, beautifully complemented by decorative wood ceiling beams that add warmth and architectural character. The open-concept kitchen is equally impressive, featuring white cabinetry, granite countertops, an oversized center island, stainless steel appliances, a gas cooktop, walk-in pantry, expansive butler's pantry, and a dedicated breakfast nook overlooking the backyard. Privately tucked away on the first floor, the primary suite offers engineered hardwood flooring, dual walk-in closets with custom shelving, and a spa-inspired bath with separate vanities, a soaking tub, and an oversized walk-in shower. A private office with matching engineered hardwood flooring, formal dining room, laundry room, and powder bath complete the main level. Upstairs, three spacious bedrooms, two full bathrooms, an oversized loft, and a flexible bonus room provide endless possibilities for a media room, fitness space, playroom, or potential fifth bedroom. Step outside to your own private retreat featuring a saltwater pool with water features, covered lanai, fenced backyard, and the added privacy of no rear neighbors. Thoughtful enhancements throughout the home include the custom family room built-in with electric fireplace, decorative ceiling beams, engineered hardwood flooring in the primary suite and office, permanent exterior architectural trim lighting, a whole-home security camera system, overhead garage storage, newer kitchen appliances, a new microwave, a newer pool pump, and spray foam insulation for enhanced energy efficiency. Residents enjoy resort-style amenities including a clubhouse, community pool, playground, and dog park, all just minutes from Hamlin Town Center, top-rated schools, shopping, dining, major highways, and Walt Disney World. Blending timeless design, quality craftsmanship, and an unbeatable location, 5513 Thomas Square Drive is a rare opportunity to own a truly move-in-ready home in the heart of Winter Garden.

5513 Thomas Square Drive, Winter Garden
$1,095,000
5 Beds ⋅ 4 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code
Welcome Home! Meticulously maintained home boasting with upgrades on an oversized conservation lot with peaceful pond views. Designed for both everyday living and entertaining, features a completely remodeled kitchen with quartz countertops, premium Café appliances, designer backsplash, a massive island with sitting space, upgraded lighting and a custom walk-in pantry. The first floor includes a private office, spacious family room, guest suite with a full bath, laundry room, formal living, and dining room. Porcelain tile flows throughout the main living areas, French doors lead to your private backyard retreat with a fully screened lanai overlooking the saltwater pool and spa, complete with new tile. Upstairs you'll find a stunning media room complete with theater seating and a granite wet bar, 4 bedrooms and a full bath. The primary suite features tray ceiling, plantation shutters, dual walk-in closets, and remodel ensuite bath. Updates include dual vanities, walk-in glass shower, clawfoot tub, and stunning upgraded tile throughout. Two car garage with an upgraded paver driveway. Located in a highly sought-after community of Westfield Lakes. Excellent public schools and convenient access to shopping, dining, and major highways, this exceptional home offers the perfect combination of luxury, comfort, and location. Schedule a private showing today!

626 English Lake Drive, Winter Garden
$650,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Great house fronting the park, gym, and community pool. Tons of upgrades inside and out. Beautiful screened pool with motorized shade for privacy on patio. Saltwater pool. Luxury Vinyl Plank throughout the house. NO Carpet! Kitchen has lots of upgrades as well. KitchenAid appliances. Wall oven and cooktop. Samsung refrigerator included. Washer and Dryer also stay! 5 mounted TV's will convey as well! Ring alarm system with cameras as well. Plantation shutters throughout.

14048 Lake Abbotts Drive, Winter Garden
$850,000
4 Beds ⋅ 2 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to your next obsession. Nestled on one of Winter Garden's iconic brick-lined streets in the highly sought-after Golf Cart District, this completely remodeled home delivers the perfect blend of historic charm, modern luxury, and walkable lifestyle - just minutes from Downtown Winter Garden, Plant Street Market, the West Orange Trail, award-winning restaurants, breweries, coffee shops, boutiques, farmers market and year-round community events. From the moment you step inside, you'll love the light filled open floor plan, gorgeous hardwood floors and designer finishes throughout. The stunning chef's kitchen is truly the heart of the home, featuring a farmhouse sink, new quartz countertops, under-cabinet lighting, abundant cabinetry and an oversized island overlooking the spacious living and dining areas - perfect for entertaining, hosting wine nights, game days, holiday gatherings or cozy evenings at home. With four spacious bedrooms, a dedicated home gym and a flexible bonus/playroom with classic French doors, there's room for everyone to live, work and play. Step outside and discover your own private Florida retreat featuring a new screened-in pool enclosure, creating the ultimate backyard oasis for pool parties, weekend BBQs, relaxing afternoons and year-round outdoor living. The expansive patio offers plenty of room for dining, entertaining and making memories with family and friends. The updates don't stop there. The home has been completely renovated from top to bottom, including new plumbing, updated electrical, roof, kitchen, bathrooms, flooring, fixtures, and finishes - giving you the confidence of modern systems with timeless style. Love the outdoors? You're just steps away from beautiful Lake Apopka where you'll enjoy breathtaking sunset views, walking and biking trails, kayaking, fishing and everything that makes Winter Garden one of Central Florida's most desirable places to call home. If you've been searching for a move-in ready home in Downtown Winter Garden, with a screened pool, open concept living , designer upgrades, Golf Cart District access and an unbeatable location close to shopping, dining, parks, top-rated schools and major highways - this is the one! Don't miss your chance to own one of Winter Garden's most desirable homes.

64 E Crest Avenue, Winter Garden
$859,000
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 3b SubDv. ⋅ 34787 Zip Code
RARE FIND! ** Experience resort-style living in this exceptional home on a rare OVERSIZED 0.15-acre homesite, ideally located JUST MINUTES from the vibrant HAMLIN Town Center in one of Winter Garden's most desirable areas. Featuring a stunning nearly **NEW HEATED SALTWATER PRIVATE POOL, premium summer kitchen, expansive covered lanai, elegant travertine patio, and a fully fenced backyard, this property offers the Florida lifestyle today's buyers are looking for. Offering 2,990 square feet, 4 spacious bedrooms, and 2.5 bathrooms, this home perfectly blends luxury, comfort, energy efficiency, and everyday functionality. Designed with flexibility in mind, it also features a versatile flex room with the potential to serve as a future fifth bedroom, home office, or study, as well as a spacious upstairs bonus room ideal for a media room, playroom, or additional family living space. The primary suite is complemented by an oversized walk-in closet. Beyond its outdoor living spaces, this home also delivers a remarkable financial advantage. The FULLY PAID-OFF SOLAR PANEL SYSTEM, valued at over $30,000, means no lease or loan to assume and helps keep the average monthly electric bill at approximately $80, even during Florida's summer months. That's hundreds of dollars in energy savings every month, providing exceptional long-term value and sustainability for the next homeowner. The fully fenced backyard is a true private retreat designed for entertaining and relaxing year-round. The nearly new heated saltwater pool was built with all required permits, offering the confidence and peace of mind that come with a recently constructed, modern pool system. Outdoor living is completed by the covered lanai and travertine deck, a premium summer kitchen, and low-maintenance artificial turf. A convenient first-floor half bathroom with direct access to the backyard makes entertaining even more enjoyable. Beyond its outdoor living spaces, this home also delivers a remarkable financial advantage. Additional upgrades include a beautifully remodeled upstairs bathroom with a frameless glass shower enclosure, custom closet systems, two independent HVAC systems for enhanced comfort and efficiency, professionally installed gutters, an epoxy-coated garage floor, and overhead garage storage racks. The location adds even more value: just minutes from Hamlin Town Center, with convenient access to top-rated schools (Summerlake Elementary, Hamlin Midle School, Horizon High School), Publix, Walmart, restaurants, cafés, boutique shopping, Cinépolis Luxury Cinemas, PopStroke, Urban Air Adventure Park, and SR-429. As a resident of the highly desirable Summerlake community, you'll enjoy standout amenities, including a clubhouse, fitness center, community pool, tennis courts, playgrounds, walking trails, and lawn maintenance included through the HOA. Move-in ready and thoughtfully upgraded throughout, this home offers a rare combination of outdoor living, energy efficiency, and prime Winter Garden location. Schedule your private showing today! All information, including room dimensions, square footage, HOA fees, community amenities, and restrictions, is deemed reliable but not guaranteed and should be independently verified by the buyer and buyer’s agent.

7594 Lake Hancock Boulevard, Winter Garden
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