Winter Garden Homes with Pool View

Winter Garden Homes with Pool View

Welcome to Winter Garden, Florida—a charming city that beautifully blends small-town warmth with vibrant urban energy. Nestled in the heart of Orange County, Winter Garden is renowned for its picturesque landscapes, friendly community, and rich history. With a thriving downtown area filled with delightful shops, delectable dining options, and an array of recreational activities, it's no wonder that Winter Garden has become a sought-after destination for families and individuals alike.

One of the standout features of this lovely city is its stunning homes with pool views. Imagine waking up each morning to the serene sight of shimmering water, surrounded by lush greenery and vibrant florals. These homes offer an idyllic retreat where you can unwind and entertain friends and family in your own private paradise. Whether you’re looking for a cozy single-family home or a spacious estate, Winter Garden boasts a diverse range of properties that cater to every lifestyle and budget.

In addition to the beautiful homes, Winter Garden is also home to a number of parks, walking trails, and recreational facilities that encourage an active lifestyle. The West Orange Trail, for example, is perfect for biking, jogging, or leisurely strolls, allowing residents to soak in the natural beauty of the area.

With its perfect blend of community spirit, outdoor adventure, and stunning homes with pool views, Winter Garden, FL is not just a place to live—it's a place to thrive. Come discover your dream home in this enchanting city!

Newest Winter Garden Homes with Pool View

234 N Lakeview Avenue, Winter Garden
$2,199,900
5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Welcome to The Birdhouse, one of Downtown Winter Garden's most iconic residences. Situated just blocks from Plant Street, the West Orange Trail, and the shores of Lake Apopka, this remarkable property offers a rare opportunity to own a thoughtfully restored home that seamlessly blends timeless architecture with modern luxury. Set on an expansive and highly coveted 0.51-acre lot, The Birdhouse delivers an unrivaled combination of character, sophistication, and downtown living. Originally built in 1920, this meticulously restored home preserves its historic charm through exposed brick walls, wood-beamed ceilings, vintage glass doorknobs, original lighting fixtures, multiple fireplaces, beautifully maintained hardwood floors and more. Natural light pours through original diamond-pane windows into the spacious family room, while the formal living and dining rooms showcase timeless character and thoughtful custom details. The chef's kitchen is a true focal point with a distinctive mix of old-world charm and modern design that combine luxury and function. Features include Cambria Portrush quartz countertops, custom floor-to-ceiling cabinetry, premium ZLINE appliances with an 8 burner gas stove range below exposed brick walls, a statement tile backsplash and custom range hood. Floating wood shelves, an expansive breakfast bar and cozy breakfast nook with built-in seating complete its design. A spacious mudroom and custom laundry room offer extensive cabinetry and counterspace for both storage and everyday convenience and a dedicated home office includes a custom built in desk. Set apart from the living areas and secondary bedrooms, the newly designed primary suite serves as a private sanctuary. Accessed through its own hallway, this spacious retreat features vaulted wood-paneled ceilings, an enormous walk-in closet, and a spa-inspired bath with dual vanities, two private water closets, a large glass-enclosed shower and elevated finishes throughout. Four additional generously sized bedrooms provide exceptional flexibility, including a second primary suite with dual closets and an ensuite bath, an additional ensuite bedroom overlooking the pool, and two bedrooms with a full guest bath positioned in between. The enormous fully fenced backyard is designed for year round enjoyment with a gas-heated saltwater sport pool, outdoor kitchen, expansive brick paved deck, detached covered lanai, and low-maintenance turf. Towering above it all is one of the property's most extraordinary features: a majestic 390-year-old oak tree, recognized as the oldest recorded oak tree in Orange County, providing unparalleled beauty and shade. Equally noteworthy, the home's original exterior waterspout remains in place and fully operational, offering a unique connection to the property's storied past. A double carport includes both a Tesla and golf cart charging station as well as a large storage closet equipped with power and a shop desk. Recent home improvements include a new roof (May 2026), updated PVC plumbing and drain field, new air handler, new tankless hot water heater, new water filtration system and new structural support trusses installed beneath the home to enhance long-term stability and strengthen the property's foundation for generations to come. A rare blend of historic significance, modern luxury, and premier location, The Birdhouse represents one of Downtown Winter Garden's most exceptional residential offerings. Schedule your private viewing today!

234 N Lakeview Avenue, Winter Garden
1069 Glenharbor Circle, Winter Garden
$565,000
3 Beds ⋅ 2 Baths ⋅ Glenview Estates 1st Add SubDv. ⋅ 34787 Zip Code
Welcome to 1069 Glenharbor Circle — a turn-key, 3 bedroom, 2 bathroom Winter Garden sanctuary offering complete freedom with NO HOA and located within the highly sought-after Winter Garden Golf Cart District! Situated on an expansive, shade-draped lot just under half an acre featuring a magnificent mature oak tree, this home features major recent upgrades for complete peace of mind. Inside, enjoy fully renovated bathrooms — including a luxury primary bath (renovated Aug 2024) and a beautifully appointed second bath (renovated May 2026). Other major updates include a recent full roof replacement (Dec 2025), complete replacement of all AC ductwork (Nov 2025), and energy-efficient windows installed across 2021 and 2025. The backyard showcases a private, resort-style paradise featuring a custom, screen-enclosed pool and an oversized sun shelf perfect for lounge chairs. With no HOA restrictions, you have total freedom to park boats, RVs, or trailers on your sprawling half-acre lot. Located just minutes from the West Orange Trail, Winter Garden Downtown Historic District, top-rated schools, and major highways, this home delivers the ultimate Winter Garden lifestyle.

1069 Glenharbor Circle, Winter Garden
14501 Grove Resort Avenue Unit 1218, Winter Garden
$235,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condo 1 SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park, where vacation ownership meets the full Orlando resort lifestyle! This beautifully furnished 2-bedroom, 2-bath condo-hotel residence offers a spacious, comfortable retreat just minutes from Walt Disney World and Central Florida’s world-famous attractions. Designed for both relaxation and convenience, the residence features an open living and dining area, a fully equipped kitchen with stainless steel appliances, generous cabinetry and counter space, in-suite washer and dryer, and a private screened balcony—the perfect place to enjoy your morning coffee or unwind after a day at the parks. The spacious primary suite offers a private bath with dual vanities, soaking tub and separate shower, while the second bedroom and full bath provide plenty of room for family and guests. At The Grove, the resort itself is part of the experience. Spend the day at Surfari Water Park featuring a 695-foot lazy river, dual water slides, zero-entry pool, kids’ activity pool and exciting FlowRider® Double surf simulator. Looking for a slower pace? Relax at The Springs Pools with three full-size pools and an oversized hot tub, enjoy the natural beauty of Lake Austin, work out in the 24-hour fitness center, or take advantage of the resort’s restaurants, bars, family activities and recreation. The resort also offers transportation to Walt Disney World, Universal Orlando and SeaWorld, making it easy for guests to experience everything Orlando has to offer. Disney Springs is approximately 11 miles away, with SeaWorld, Universal Orlando, Epic Universe and countless dining, shopping and entertainment destinations all within easy reach. Ownership is made even more convenient by an association fee that includes many of the expenses normally handled separately, including electricity, water, sewer, trash, cable, internet, pest control, security, common-area and building maintenance, and recreational facilities.* Whether you're searching for your own Florida vacation getaway, a second home near the theme parks, or a furnished resort property with vacation-rental potential, Unit 1218 offers the opportunity to own where millions of visitors come to vacation every year. Come for the parks. Stay for the resort. Own a piece of the Orlando vacation lifestyle at The Grove Resort & Water Park.

14501 Grove Resort Avenue Unit 1218, Winter Garden
1316 Southern Sun Drive, Oakland
$1,050,000
5 Beds ⋅ 4 Baths ⋅ Hull Island SubDv. ⋅ 34787 Zip Code
Discover a private retreat in Hull Island at Oakland, an intimate community of limited residences offering a peaceful, exclusive feel near charming downtown Winter Garden and the celebrated West Orange Trail. Enjoy community amenities and a dock for taking in sunrise along Lake Apopka. With no immediate rear neighbors or neighbors on one side, this home backs to a conservation area for added privacy and a natural backdrop. Featuring 5 bedrooms, 4 full bathrooms and 3,658 square feet, the home offers an open kitchen, a versatile loft and a primary suite with its own screened porch overlooking nature. A rear patio with pavers and a covered screened enclosure creates an inviting setting for relaxing and entertaining. Room to gather, space to unwind and a setting to enjoy. Schedule your private showing.

1316 Southern Sun Drive, Oakland
15210 E Oakland Avenue, Winter Garden
$1,924,999
4 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code
Custom-built by Justice & Wood Builders, this 4-bedroom, 3-bathroom Modern Farmhouse sits on a rare 0.47-acre lot in Oakland Hills, an intimate community of just 17 homesites minutes from Historic Downtown Winter Garden. Towering, moss-draped oaks frame the property and set a peaceful tone from the moment you arrive. Inside, wide-plank wood floors and abundant natural light flow through an open-concept living space crowned by cathedral ceilings and exposed timber beams. The kitchen goes well beyond standard gourmet, with shaker cabinetry, quartz countertops, a massive blue-gray center island, a deep farmhouse sink, professional stainless steel appliances, and a natural gas range built for serious cooking. The bedrooms are generously sized and well separated. The upstairs bedroom is flexible enough to serve as a home office, gym, media room, or guest suite, and it has air-conditioned storage and a large walk-in attic. The bathrooms feature clean lines, modern fixtures, and custom tilework. The laundry room has extensive cabinetry, quartz counters, and a patterned tile backsplash. The three-car garage includes an EV adapter in the third bay. Out back, the fully fenced yard feels like your own resort, with a pool and spa surrounded by a spacious paver patio and a fire pit area for evenings outside. Downtown Winter Garden's Farmers Market, Plant Street Market, boutiques, and restaurants are minutes away by car or golf cart.

15210 E Oakland Avenue, Winter Garden
1720 Lake Roberts Landing Drive, Winter Garden
$1,399,999
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
15680 Panther Lake Drive, Winter Garden
$1,950,000
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
14501 Grove Resort Avenue Unit 1420, Winter Garden
$249,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
***Amazing views from this two-bedroom, two-bathroom fully-furnished condo in the beautiful Grove Resort and Water Park Resort! Fourth floor views over the Springs Pools, with Lake Austin beyond that! Enjoy the morning sunrise with a coffee on your screened-in balcony!! These condos are fully managed by the onsite rental company, so when you are not using it, you can earn some income from guest bookings! These are ideal for snowbirds who wish to spend up to 179 nights per year in their unit, and then have the hands free experience of management renting it out when they are not using it! Full kitchen, full size washer and dryer, dining area, sleeper sofa, deep comfortable mattresses, all lend to a home from home for owners and guests! The Valencia Restaurant is located next to the Springs Pools area, which has three separate pools and a hot tub, and the 24/7 gym is also in this area. Take a stroll down the boardwalk to Lake Austin and paddle a swan boat, or try some fishing from the dock! A leisurely stroll takes you to the Surfari water park, with large heated pool, lazy river, water slides, splash area, and the Surfari surfing experience! The Longboard Bar and Grill is excellent for food and refreshing beverages while spending your day there! The Flip Flop games room has over 6000sf of exciting games and mini golf! The Marketplace sells all you need for snacks, food, small necessities, and the gift shop has souvenirs, clothes, sun cream, etc for essentials. The concierge located in the front lobby sells theme park tickets, and will book your seat on the FREE daily shuttle to the Disney Parks! Call NOW for more information!!***

14501 Grove Resort Avenue Unit 1420, Winter Garden
2202 Redmark Lane, Winter Garden
$824,900
5 Beds ⋅ 4 Baths ⋅ Carriage Pointe A-I & L SubDv. ⋅ 34787 Zip Code
Welcome to a home where thoughtful design, custom details, and relaxed Florida living come together. Located in a gated Winter Garden community, this 5-bedroom, 3.5-bath residence offers generous space for everyday living and entertaining, including a private office, formal dining room, spacious living room, great room, and versatile upstairs bonus room. The first-floor primary suite provides privacy and convenience, while an interior laundry room with a utility sink adds everyday functionality. This home has been maintained as a smoke-free, pet-free residence. At the heart of the home, the great room opens seamlessly to an expansive kitchen with generous storage and a welcoming eat-in area. Custom built-ins, a stone-surround electric fireplace, and ceiling speakers make the great room an inviting place to gather or unwind. Crown molding, upgraded lighting, Pottery Barn curtain rods, and plentiful closet space reflect the attention to detail throughout. Fresh interior paint enhances the move-in-ready appeal, while custom office cabinetry creates a beautiful and functional workspace. An upgraded wrought-iron staircase adds architectural character and leads upstairs, where the flexible bonus room offers space for a media room, playroom, fitness area, or additional living room. Sliding glass doors open to a screened outdoor retreat featuring a covered lanai and sparkling saltwater pool with a sheer-fall water feature. Enjoy leisurely Florida afternoons, sunset views, and evenings spent entertaining. The outdoor living area is pre-wired for television and equipped for speaker connectivity, making it easy to personalize your gathering space. Recent updates include a new HVAC system installed in January 2026 with a damper system and remotely controlled thermostat, a water heater installed in 2024, and fresh exterior paint completed in 2026. A spacious three-car garage with an additional storage closet beneath the stairs, an elegant paver driveway, and a transferable Massey termite bond further enhance the home’s appeal. Community amenities include a playground, tennis and pickleball courts, soccer field, and picnic area. Ideally located for enjoying Walt Disney World and other Central Florida attractions, this home also offers access to top-rated schools and Winter Garden’s dining, shopping, entertainment, and recreation. Convenient access to State Road 429, Florida’s Turnpike, and State Road 535 makes traveling throughout Central Florida easy. Orlando International Airport is approximately 33 miles away.

2202 Redmark Lane, Winter Garden
14501 Grove Resort Ave Unit 1707, Winter Garden
$239,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort & Spa SubDv. ⋅ 34787 Zip Code
Exceptional opportunity to own a spacious top-floor 3-bedroom, 3-bathroom condo at The Grove Resort & Water Park, just minutes from Walt Disney World! This fully furnished 1,544 sq. ft. “Sable” floor plan offers an ideal combination of personal vacation use and income-producing potential through The Grove’s professionally managed hotel rental program. Located on the 7th and top floor of Building 1, the condo features a spacious split-bedroom layout, three full bathrooms, a well-equipped kitchen with granite countertops, comfortable living and dining areas, and a screened balcony with elevated views. The Grove delivers the complete Orlando resort experience with Surfari Water Park featuring water slides, a lazy river, splash areas and private cabanas, multiple onsite dining options, a full-service spa, fitness center, arcade, and a 20-acre activity lake offering fishing and water activities. When you're not enjoying the condo yourself, the turnkey rental program provides professional management for vacation rentals. Whether you're looking for your own Orlando getaway or a furnished vacation rental investment near Disney, this top-floor 3-bedroom residence offers an outstanding opportunity at one of Central Florida's most amenity-rich resort destinations.

14501 Grove Resort Ave Unit 1707, Winter Garden
14048 Larkspur Lake Drive, Winter Garden
$1,255,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and presented in like-new condition, this exceptional single-story lakefront home blends an elevated luxe coastal feel with relaxed Florida waterfront living. Set on a rare oversized lot along skiable Huckleberry Lake, with potential for building a private boat dock, subject to permitting. the property offers exceptional privacy and space, with approximately 40 feet of separation between neighboring homes. The light and inviting interior features (4) four bedrooms, (3) three full baths, and a spacious open-concept floor plan. The beautifully updated kitchen showcases quartz countertops and flows seamlessly into the main living and entertaining areas. A generously sized open flex room offers additional versatility as a formal dining room, home office, formal living room, or sitting room and can easily be enclosed for additional privacy. Step outside to a large fenced backyard with a private pool and spa, all overlooking Huckleberry Lake. Enjoy direct lake frontage and water access, with the opportunity to built your own private boat dock, subject to permitting. The (3) three-car garage includes a Tesla EV charger, and the expansive driveway accommodates up to (6) six additional vehicles. Lakeview Pointe offers a community dock on Huckleberry Lake, resort-style pool with splash area, and fully equipped fitness center. The HOA also takes care of the home's exterior lawn maintenance, giving you more time to enjoy the lake, pool, and Florida lifestyle. Ideally located in Winter Garden's Horizon West area, with easy access to SR 429 and minutes from shopping, dining, entertainment, and everyday conveniences. The property is currently zoned for A-rated Summerlake Elementary, Hamlin Middle School, and Horizon High School. Nearby early-learning options include Primrose School of Horizon West, The Learning Experience - Horizon West, and KLA Schools of Horizon West. Walt Disney World is approximately 20 minutes away. Buyers should independently verify current school assignments and grades. A rare opportunity to own a beautifully remodeled single-story pool home on skiable Huckleberry Lake, combining privacy, flexible living spaces, an oversized lakefront lot, and true Florida waterfront living.

14048 Larkspur Lake Drive, Winter Garden
7301 Wild Blackberry Trail, Winter Garden
$2,400,000
6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 - Independence SubDv. ⋅ 34787 Zip Code
Virtually Staged. This statuesque Mediterranean home is perfectly placed along Hancock Lake for maximum lakefront enjoyment. Your private covered dock protects a 20’ +/- boat w/lift as well as the lifts for 2 jet skis. Motor boat or pontoon around the lake, bring your favorite fishing rod or ski on one of the nicest skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, one of a few lakefront properties in the neighborhood that have one, manicured gardening beds for your green thumb and room for outdoor activities and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry and a delightful custom salt pool showcasing a water slide, fiber optic lighting, solar heated spa and pool ledge. Enjoy the lake views then after sunset, pull down the projector screen for your favorite flick before watching the nightly fireworks show from the Disney park. The home's exterior and interior were freshly painted. Notice the wide baseboards and crown trim throughout. Spectacular front entrance with impressive light fixtures that accentuate the formal living and dining areas and frame your first glimpse of the lake. Impressive, upgraded Double Pane Low E sliding doors showcase the patio and lake then pocket to merge your spaces. The Kitchen is equipped with multiple food prep areas, generous walk-in pantry, and a central island workstation with seating for informal gatherings. A hallway behind the Kitchen shares the cabana bath and another first floor bedroom or den or office with a sliding door to the patio and a sizable walk-in closet. The first level’s primary suite has private patio access too and a lovely bay window styled seating area. (The previous owners used this primary as a media room complete with surround sound that remains intact). The loft also has new sliding doors to the screened balcony area overlooking the patio and lake along with projection equipment and bar/kitchen ideal for entertaining. The upper level contains a large ensuite with a private balcony, another ensuite, two bedrooms that share a hall bath and another bedroom with a private balcony overlooking the patio. The security system is located in the upstairs laundry room. Both A/C Systems, all patio doors, exterior balcony railings secured and LR/DR bamboo engineered hardwood flooring are updates you'll appreciate. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy. Plans for the new satellite elementary campus of Windemere Preparatory School are underway that will be located less than 2 miles from this home. ***Photos of fireworks and formal dining area are THE ONLY PHOTOS virtually staged.

7301 Wild Blackberry Trail, Winter Garden
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