Winter Garden Homes with Private Pool type

Winter Garden Homes with Private Pool type

Welcome to Winter Garden, Florida—a charming city that beautifully blends small-town warmth with modern conveniences. Nestled just a short drive from the vibrant attractions of Orlando, Winter Garden boasts a rich history, stunning landscapes, and a thriving community spirit. With its picturesque downtown area featuring delightful shops, restaurants, and a bustling farmers market, it’s no wonder that Winter Garden has become a sought-after destination for families and individuals alike.

One of the standout features of Winter Garden is its array of beautiful homes, many of which come with private pools—an ideal retreat for those warm Florida days. Imagine stepping out into your own backyard oasis, where you can soak up the sun, host barbecues, or simply unwind with a refreshing swim. Homes with private pools in Winter Garden are designed for both relaxation and entertainment, offering spacious layouts and luxurious amenities that cater to your lifestyle.

The community is also rich in recreational opportunities, with an abundance of parks, trails, and sports facilities. Whether you enjoy hiking, biking, or simply strolling through nature, Winter Garden has something for everyone. With its excellent schools, friendly neighborhoods, and a strong sense of community, it’s no surprise that Winter Garden is a perfect place to call home.

Discover the allure of Winter Garden and explore the charming homes with private pools that await you. Your dream home in this delightful city is just a splash away!

Newest Winter Garden Homes with Private Pool type

5 Beds ⋅ 4 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code

If you’ve been searching for a spacious Winter Garden home with a private pool, peaceful conservation views and room for everyone, this former model may be exactly what you’ve been waiting for! With 5 bedrooms, 4 full bathrooms and the potential for a 6th bedroom, this home combines privacy, flexibility and Florida indoor-outdoor living in a way that’s increasingly difficult to find. Situated on a peaceful wooded conservation lot, the home has been thoughtfully updated with a renovated kitchen, LVP flooring throughout the first floor, and new carpet and paint upstairs. Generous living and dining areas provide plenty of room for everyday living and entertaining, while the family room features easy access to the screened pool and deck. The spacious primary suite includes a private sitting area and built-in shelving, creating a comfortable retreat. Upstairs, the oversized bonus room with its own adjoining full bathroom offers exceptional flexibility and could serve as a second primary suite, private guest quarters, media room or game room. Need even more space? The downstairs office could potentially be converted into a 6th bedroom, making this floor plan adaptable to a variety of needs. Step outside to one of the home's most appealing features—the screened-in pool and deck overlooking the wooded conservation area. With no immediate rear neighbor, it's a private setting for morning coffee, afternoons by the pool, entertaining friends or simply relaxing at the end of the day. Located in the beautiful gated Wintermere Pointe community, this home brings together the space, privacy and flexibility along with a private pool and conservation setting that can be difficult to find. Call and schedule your private showing today!

2242 Wintermere Pointe Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Deer Island SubDv. ⋅ 34787 Zip Code

Welcome home! This turnkey, exquisite custom home enables you to wake up to shimmering water views of Johns Lake and step into the lakefront lifestyle you’ve been dreaming of. On an acre in a gated community, sellers spared no expense on a complete renovation— exterior to interior and down to the studs. New windows, high end finishes, and designer details in every room rival new construction. Upon entering, you’ll be captivated by an abundance of natural light, soaring ceilings and panoramic water views. The foyer leads to the spacious living/office/flex space and dining room with stunning dry bar and 180+ bottle wine fridge. The large family room with fireplace feature wall and bay window adjoins the true gourmet kitchen for open concept living, overlooking the lake and community pond with lighted fountain. A chef’s kitchen features tall kitchen cabinets for extra storage, massive center island, large sink, Fisher and Paykel double-drawer dishwasher, Scotsman pellet icemaker. The all Viking appliance pkg includes a 36” refrigerator with 30” freezer, dbl ovens, warming drawer, 6 burner induction stove top. A plumbed, built-in Miele espresso machine provides your favorite morning coffee, hot water, and more. A reverse osmosis water filtration system feeds the kitchen sink, icemakers, coffee machine. The sunroom boasts two walls of new Pella hurricane rated slider doors that flood the home with natural light and frame the stunning waterfront scenery and provides a seamless connection between indoor and outdoor living opening onto the sandstone lanai with oversized resort style sparkling saltwater pool, spa and waterfall. The lanai roof structure is unique in that the vaulted roof and screening provides all weather protection to the pool, built in bar and overflow patio area allowing for entertaining in any weather or watching the Disney fireworks or rocket launches. The lanai is outfitted with 3 large DC ceiling fans and integrated watering system. Spacious primary bedroom with lanai access overlooks the lake and boasts a spa-like bathroom with dual vanities, frameless zero entry shower, free-standing tub and large walk-in closet. The split bedroom plan allows for maximum privacy. Secondary bedrooms are spacious with oversized closets. The exterior, with its professional landscape design and lighting, is designed for play, relaxation and beauty. Enjoy direct access to Johns Lake and spend your days boating, jet skiing, kayaking, paddle boarding, fishing or simply relaxing. A paver walkway from the house leads to the expansive back yard, beachfront, and large fire pit area, perfect for play and entertaining. Private dock with remote boat lift and double jet ski lift allows for lake enjoyment with effortless access. Dock is equipped with running water, lights and no/low maintenance composite decking and handrails. The deep garage is oversized with storage racks and an additional air-conditioned bonus space to be used as a craft/exercise room/home office or air-conditioned storage. Neighborhood amenities include community dock, boat ramp, tennis/pickleball court, basketball court, cable/internet. Conveniently and centrally located with easy access to the Turnpike, 429, 408, downtown Winter Garden and Orlando, the airport, Disney, Universal and area attractions. Minutes to restaurants, shops, hospitals, West Orange Trail. Link to interactive floor plan: https://www.zillow.com/view-imx/6a573be4-fd0d-4649-9df8-88349b2426f6?initialViewType=pano

263 Deer Isle Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to 15675 Panther Lake Drive, an exceptional lakefront residence within the prestigious Lakeshore Preserve community of Winter Garden, where refined interiors, expansive water views, and effortless Florida living come together in a beautifully curated setting. Offered fully furnished, this sophisticated five-bedroom, five-bathroom residence has been thoughtfully enhanced with custom millwork, elevated finishes, and carefully selected upgrades throughout. The heart of the home is an expansive open-concept living space, seamlessly connecting the family room, dining area, and kitchen while framing beautiful views of the lake. Designed equally for intimate everyday living and sophisticated entertaining, the main level also features a dedicated coffee station, generous pantry and storage spaces, laundry room, and a private primary suite offering the convenience of first-floor living. One of the three garage bays has been thoughtfully transformed into a fully equipped private fitness studio, creating a dedicated wellness space within the residence while offering the flexibility to be converted back to garage use if desired. Upstairs, four additional bedrooms are complemented by a spacious loft and private home office. Expansive windows throughout the upper level capture the lake views and bring an abundance of natural light into the home. Beyond its interiors, the property's waterfront setting creates a sense of openness and tranquility, offering a beautiful lake view and access, summer kitchen, Florida room, heated pool and a spa. It is a true oasis from morning through evening. Ideally positioned in Winter Garden, the residence provides the privacy and distinction of an upscale community while remaining conveniently connected to the area's exceptional dining, shopping, entertainment, and lifestyle destinations. 15675 Panther Lake Drive represents a rare opportunity to acquire a fully furnished*, beautifully appointed lakefront home where comfort, functionality, and the Florida lifestyle exist in perfect balance.

15675 Panther Lake Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lake Roberts Lndg E SubDv. ⋅ 34787 Zip Code

Your chance to own the FORMER MODEL for entire community. Set behind the GATED ENTRY of Lake Roberts Landing with community fishing pier to 116 acre Lake Roberts. THE IDEAL FLOOR PLAN you have been waiting for, 5 beds, office, movie theatre and bonus.. PLUS this rare gem... Primary bed and an additional En Suite on 1st floor !!! Incredible street presence and MASSIVE fenced back yard. Oversized covered lanai with summer kitchen provides the ideal place to relax and entertain. Screen enclosed pool and spa with paver deck competes the perfect back yard to embrace the Florida Lifestyle. Entering the home you are greeting with soaring ceilings of a foyer replicating a great hall feel. Formal dining and private office (on top of the 5 bedrooms) flank the entry, Both boasting amazing detail and carpentry that would be expected in the former model. Pass the wet bar for entertaining to the formal living room with same soaring ceiling height as the foyer itself. The heart of the home well appointed with timeless wood cabinets, lots of workspace and vented cook top too. The family room overlooks the pool, yard and lanai. DOWNSTAIRS MASTER is incredible and a RARE SECOND EN SUITE DOWNSTAIRS is perfect for guests or aging family members. Ascend the showstopping curved staircase to the equipped home theatre and additional BONUS ROOM. 2 large secondary bedrooms with jack and jill set up PLUS another EN SUITE/ 2nd primary bedroom on the 2nd floor. ALL beds have a walk-in closet too ! 3 car tandem garage, tile roof. Minutes to 429 expressway, countless shopping and dining options in literally every direction. Sought after K-12 school district plus Foundation Academy and Windermere Preparatory school campuses minutes away. Disney less than 15 away and 20 to Downtown Orlando. This is truly an amazing opportunity for one buyer. Move fast, this is one that is priced to sell.

1720 Lake Roberts Landing Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code

Welcome home to this stunning pool home with a beautiful water view in desirable Westfield Lakes! Offering 2,335 square feet in a triple-split design, this home features a screened pool overlooking the water and an impressive list of recent improvements, including roof (2023), AC (2019), water heater (2023), whole-home repipe (2021), pool resurfacing and new tile (2020), repainted kitchen cabinets (2026) and fully remodeled bathrooms. Enjoy the Florida lifestyle from your screened pool and lanai, whether starting the day with coffee by the water, taking an afternoon swim or entertaining family and friends. Westfield Lakes is known for its mature tree-lined streets, beautifully landscaped entrances and welcoming neighborhood atmosphere. Residents enjoy Lake Beulah with two fishing docks, scenic ponds with lighted fountains, tennis and pickleball courts, and two playgrounds. The neighborhood is also home to abundant wildlife, including sandhill cranes, herons, egrets, bald eagles and owls. With the Roper YMCA, Southwest Aquatics and two dog parks nearby, this home offers a wonderful combination of space, recreation and convenience. A screened pool, peaceful water view, major updates and plenty of space all in beautiful Westfield Lakes.

12021 Windstone Street, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 2 & 5 SubDv. ⋅ 34787 Zip Code

Ideally located in the highly sought-after Hamlin area of Winter Garden, this beautifully maintained pool home offers the perfect combination of comfort, convenience, and Florida living with beautiful lake Hancock views. Enjoy easy access to shopping, dining, entertainment, major roadways, outdoor recreation, and the many attractions and amenities throughout Winter Garden and Horizon West. Designed for effortless everyday living and entertaining, the residence features bright, spacious interiors that flow seamlessly into the outdoor living area. The private saltwater pool can be heated using either solar energy or gas, providing flexibility and year-round enjoyment. Fully paid-off solar panels offer an exceptional advantage, with no solar lease or financing obligation for the new owner. Additional improvements include one brand-new air-conditioning system, a second A/C system replaced less than three years ago, and a whole-home water softener and filtration system with reverse osmosis for drinking water. Fresh landscaping enhances the home’s curb appeal and creates a welcoming first impression. With its energy-efficient features, valuable recent upgrades, resort-style outdoor space, and desirable location, this move-in-ready property presents an exceptional opportunity to enjoy the best of the Winter Garden lifestyle. Pictures will be posted soon.

15240 Shonan Gold Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code

Welcome to 14975 Winter Stay Drive, where the work has already been done and the upgrades go far beyond builder basics. Thoughtfully improved inside and out, this Horizon West home pairs a warm, finished feel with the kind of practical upgrades you will appreciate for years to come. At the heart of the home, the kitchen features KitchenAid appliances installed in 2024. LVP flooring was added in 2025 and flows throughout the bedrooms. Plantation shutters, installed in 2026, add a polished finishing touch. Even the laundry room has been elevated with built-in cabinetry, granite countertops and additional storage. Outside is where this home really sets itself apart. The custom gunite pool, completed in 2024, features a swim shelf, heater AND chiller, upgraded screen enclosure and child safety fence, making it just as enjoyable in the heat of summer as it is on a cool Florida evening. The covered lanai was transformed into an outdoor living space with a fireplace, TV accent wall and recessed lighting, creating a true extension of the home for entertaining or relaxing year-round. The upgrades continue behind the scenes with a fully paid 15kW solar system, generator back-feed hookup, French drains along the east-facing gutters and downspouts, and overhead garage storage racks. Located in Winter Garden's sought-after Horizon West area, this is a home that has been intentionally upgraded, carefully maintained and designed to be lived in. Skip the projects and start enjoying the pool, the outdoor living space and everything this home has to offer from day one.

14975 Winter Stay Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Wintermere Harbor Ph 02 48 21 SubDv. ⋅ 34787 Zip Code

Welcome home to this one-story pool home situated on an oversized lot that overlooks a pond! ***NEW WINDOWS, NEW COMMODES, 2022 ROOF, 2020 SMART POOL*** Tucked into the back of this gated community, this spacious oasis is ready for its next owners. One of Florida's most popular floor plans features a formal living space at the entrance of the home, casual living space in the middle of the home, the primary suite privately on one side of the home, and the 3 secondary bedrooms on the other side of the home. Choose to repurpose the "formal living space" into whatever your wants and needs may be, or use them as the formal living room and formal dining room as the builder intended. The primary suite has an extension included and is ready to be used as yet another flex space. French doors open from this extension right onto the covered outdoor living space. The primary bathroom boasts a soaking tub, dual vanities, and 2 custom closets. The casual living space is open and inviting with the kitchen, large dining nook, and family room, and lots of natural light brightens this space up even more by way of a wall of sliding glass doors that lead to the outdoor living space, another door with a window that also leads to the outdoor living space, and a set of bay windows in the dining nook. Bedrooms 2 and 3 are located down a hallway off of the casual living space and have a full bathroom they share. The 4th bedroom is in the back of the home with its own bathroom. Step out back to the screened in patio which holds a gorgeous pool with a sun shelf and waterfall, covered portion, and extension under the screen for total and full enjoyment opportunities! Continue outside of the screen enclosure to the fully fenced in backyard that overlooks a pond. Whether looking for peace and serenity or fun and activity, this home has a solution to it all! Inquire today to for a private viewing to see if this gem will become your next home!

2039 Harbor Cove Way, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 3b-3d SubDv. ⋅ 34787 Zip Code

PRIVATE HEATED POOL & SPA with panoramic screen enclosure on premium pond front lot. Welcome home to 15526 Mango Isle Street, a stunning single-story home nestled in the highly sought-after, resort-style community of Waterleigh in Horizon West. Step inside this spacious 4-bedroom, 3-bathroom open-concept home designed for effortless living and entertaining. The Gourmet Kitchen features a grand island with breakfast bar seating, solid surface countertops, solid wood cabinetry, a walk-in pantry, and stainless steel appliances, including a built-in cooktop and oven. The bright kitchen seamlessly opens to a wide-open family room and dining area framed by large sliding glass doors that draw your eye straight to the water views. Primary Suite feels like a tranquil sanctuary featuring elegant tray ceilings, a large walk-in closet, and an en-suite bath with a double-sink vanity and walk-in shower. Layout offers a generous split-bedroom floorplan offering optimal privacy for family and guests, plus an inside utility room. Enjoy this backyard oasis and step out through the sliding glass doors into your private sanctuary. The custom HEATED pool and integrated spa sit under a picture-frame panoramic screen enclosure, giving you unobstructed, serene views of the peaceful pond. Brick pavers cover the expansive covered lanai and pool deck, offering plenty of space for outdoor dining, lounging, and soaking in Florida's famous sunsets. The Waterleigh Community is renowned for its unmatched resort-style amenities and vibrant neighborhood atmosphere. Amenities: Access to two massive lakefront clubhouses, multiple resort-style pools, splash pads, two fully equipped fitness centers, tennis and pickleball courts, beach volleyball, walking trails, dog parks, playgrounds, and a mini-golf putting course. Location is phenomenal just minutes from Walt Disney World, top-rated Horizon West schools, Hamlin Town Center dining, shopping, golf courses, and quick access to State Road 429 for easy commutes across Central Florida. This home perfectly blends luxury, comfort, and the ultimate Florida indoor-outdoor lifestyle. Schedule your private showing today!

15526 Mango Isle Street, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Bradford Creek SubDv. ⋅ 34787 Zip Code

Welcome to your ideal Florida sanctuary at 14145 Creekbed Cir! Nestled in the highly sought-after, gated community of Bradford Creek in Winter Garden, this stunning, 4-bedroom, 4-bathroom residence offers the ultimate blend of luxury, comfort, and flexibility. Designed with an expansive open-concept floor plan, gourmet kitchen, and private ensuite bedrooms, the home flows effortlessly out to your private backyard oasis. Step outside into a resort-style, fully screened enclosure featuring a sparkling heated pool and relaxing spa—perfect for year-round outdoor dining, entertaining guests, or unwinding in complete privacy. As a resident of Bradford Creek, you'll enjoy a secure gated entrance and close access to the famous West Orange Trail. Located just minutes from historic Downtown Winter Garden, Winter Garden Village, and major highways, you are seamlessly connected to Central Florida’s world-class theme parks, premier dining, and upscale shopping. Whether you are searching for a move-in-ready primary residence to settle into right away or a high-value investment opportunity in a booming market, this beautiful pool home delivers exceptional versatility, long-term equity potential, and true Florida lifestyle living.

14145 Creekbed Circle, Winter Garden

4 Beds ⋅ 5 Baths ⋅ Black Lake Park Ph 01 SubDv. ⋅ 34787 Zip Code

Welcome to an exceptional Winter Garden residence where modern luxury, thoughtful design, and resort-style living come together in one truly unique home. This extensively renovated property offers a sophisticated interior, generous living spaces, and an extraordinary outdoor entertainment and wellness area designed for the Florida lifestyle. The **second floor features 4 spacious bedrooms**, including **2 private suites**: the elegant **primary suite** and a **newly created second suite**, ideal for guests, extended family, or added privacy. In total, the home offers **3 full bathrooms upstairs**, including the private bathrooms serving both suites, plus **2 half bathrooms on the first floor** for added convenience when entertaining family and guests. The interior features a bright, open-concept layout with high ceilings, abundant natural light, and a seamless connection between the kitchen, dining, and living spaces. The renovated gourmet kitchen includes quartz countertops, custom cabinetry, stainless steel appliances, and a large center island perfect for everyday living and entertaining. The outdoor space is where this property truly stands apart. Designed as a private resort, the backyard features a **custom swimming pool and spa**, an expansive **approximately 800 sq. ft. covered pergola**, and a fully equipped **summer kitchen** with grill, sink, and generous entertaining space. A spectacular **high-definition outdoor LED video wall** creates an impressive entertainment experience for watching sports, movies, and special events from the pool, spa, or covered outdoor area. The property also includes a **private steam sauna**, a dedicated relaxation and meditation space, and professionally designed **landscaping** that enhances privacy and creates a lush, resort-style atmosphere. Located in highly desirable **Winter Garden, Florida**, this home offers convenient access to shopping, dining, recreation, major roadways, and Central Florida’s premier attractions. This is more than a renovated home—it is a private resort, entertainment destination, and luxury residence designed for exceptional everyday living. **Property Highlights** • 4 bedrooms, all located on the second floor • 2 private suites: primary suite and new secondary suite • 3 full bathrooms upstairs • 2 half bathrooms on the first floor • Approximately 2,800 sq. ft. of living space • Extensively renovated interior and exterior • Gourmet kitchen with quartz countertops and custom cabinetry • Custom swimming pool and spa • High-definition outdoor LED video wall • Private steam sauna • Fully equipped summer kitchen • Approximately 800 sq. ft. covered pergola • Dedicated relaxation and meditation area • Professionally designed landscaping • Resort-style outdoor entertainment area • Prime Winter Garden location

526 First Cape Coral Drive, Winter Garden

5 Beds ⋅ 6 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Prepare to be awed by this stunning estate from the Toll Brothers executive collection in the renowned community of Lakeshore Preserve. This home presents an ultra modern layout bringing you an environment that caters to both entertaining and every day life. The first floor is open and has 2 sets of triple pane sliding glass doors that fully open to your personal oasis. Beyond the covered lanai is a beautiful pool, spa and cabana area, perfect for a mid day swim or watching Disney fireworks at night. The kitchens, indoor and outdoor, and sure to impress even the most fastidious of chefs with the natural gas cooktop, multiple mounted range hoods, quartz countertops and more. This property is not only a "smart home" but also environmentally conscientious with newly installed solar panels and an electric car charger. All furniture is included with the sale of this home, the only thing you need is the keys to begin living your best central Florida life. Virtual Tour Available.

15680 Panther Lake Drive, Winter Garden

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