Winter Garden/Oakland Homes with Pond Frontage

Winter Garden/Oakland Homes with Pond Frontage

Nestled in the heart of Orange County, Florida, the enchanting communities of Winter Garden and Oakland offer a delightful blend of small-town charm and modern convenience. With its picturesque landscapes, vibrant downtown, and rich history, this region has become a sought-after destination for families, retirees, and anyone seeking a tranquil lifestyle close to the bustling Orlando area.

One of the standout features of homes in Winter Garden and Oakland is their stunning pond frontage. Imagine waking up to the gentle sounds of water lapping against the shore, with the sun casting a golden hue over tranquil waters. Many homes in this area boast serene views, providing a perfect backdrop for morning coffees or evening gatherings. Living by the water not only enhances the aesthetic appeal of your home but also offers a unique lifestyle, where outdoor activities such as kayaking, fishing, and birdwatching are just steps away from your doorstep.

The communities here are known for their friendly atmosphere and excellent schools, making it an ideal place for families. The historic downtown Winter Garden is a hub of activity, featuring charming boutiques, delicious dining options, and lively farmers’ markets that celebrate local produce and craftsmanship.

Whether you’re drawn to the peaceful allure of pond-front living or the vibrant community spirit, Winter Garden and Oakland promise a fulfilling lifestyle in a picturesque setting. Discover your dream home in this beautiful region and embrace the joys of lakeside living!

Newest Winter Garden/Oakland Homes with Pond Frontage

$574,900
3 Beds ⋅ 2 Baths ⋅ Signature Lks-Pcl 01b SubDv. ⋅ 34787 Zip Code
Discover refined living in this charming 3-bedroom, 2-bathroom home located in the desirable Independence community. This property offers a serene backdrop, backing directly onto a tranquil pond and conservation area. Relax on your screened-in rear porch overlooking the water, or enjoy the classic appeal of the L-shaped front porch—complete with a swing for those quiet afternoons. Inside, you will find an expansive formal dining area seamlessly connected to the living room, ideal for entertaining. The home features a recently replaced A/C system in 2025, premium tile and laminate flooring throughout, providing a clean, low-maintenance, and modern aesthetic in every room. The heart of the home is the open kitchen, featuring 42-inch cabinetry, granite countertops, a functional breakfast bar, and a cozy casual dining nook. The primary suite serves as a true retreat, boasting double-door entry, a spacious walk-in closet, and a bath equipped with a garden tub and dual vanities. Independence living offers unmatched value, with HOA fees covering your Spectrum cable and high-speed internet. Residents enjoy a premium lifestyle with access to two clubhouses, two resort-style pools, fitness centers, tennis and basketball courts, dog parks, and boat access to both Lake Speer and Lake Hancock.

14543 Whittridge Drive, Winter Garden
$737,900
4 Beds ⋅ 3 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code
Welcome to this spacious waterfront pool home located in the highly desirable Westfield Lakes community of Winter Garden! Situated on a scenic pond-front lot, this home offers beautiful water views and an open floor plan designed for comfortable living and effortless entertaining. The expansive kitchen overlooks the main living areas and features abundant cabinetry, a center island, and seamless flow throughout the home. Large windows fill the space with natural light while showcasing the peaceful backyard setting. The split-bedroom layout provides added privacy, while the screened pool and covered lanai create the perfect setting to enjoy Florida living year-round. The pool also features solar heating installed in 2022 for added efficiency and extended enjoyment throughout the seasons. Major updates include a newer roof (2019), updated HVAC system (2024), and newer water heater (2026), offering valuable peace of mind for the next owner. This home offers a fantastic opportunity for buyers looking to personalize a property with solid major-system updates and exceptional bones. Featuring a spacious layout and prime waterfront setting, the home is ideally located near shopping, dining, major highways, West Orange High School, Winter Garden Village, and downtown Winter Garden. With so much potential in a highly desirable area, this property is ready for someone to bring their vision and make it truly shine. Call today for your private showing!

120 Blue Stone Circle, Winter Garden
$1,549,000
5 Beds ⋅ 5 Baths ⋅ Avalon Cove SubDv. ⋅ 34787 Zip Code
Nestled within one of Central Florida's most exclusive neighborhoods this stunning home offers the perfect blend of luxury, comfort, and effortless entertaining. Located on a quiet cul-de-sac street boasting 5 bedrooms, 4.5 baths, a large loft and open floor plan this home is designed for everyday living and seamless hosting! Step outside to your private resort style salt water pool and enjoy nightly views of the Disney fireworks lighting up the sky! The upgraded "picture frame" pool screen design offers an uninterrupted view of the serene pond and the diverse wildlife that visits it! On the main level you will find the PRIMARY SUITE COMPLETE WITH A LUXURIOUS SPA LIKE BATH AND HUGE walk-in closet, a guest bedroom with its own full bath, the glass enclosed wine room and a convenient half bath for guests. The GOURNET KITCHEN flows to the expansive great room where 4 large sliders can open to the covered patio for the "outside inside" living!! Upstairs, in addition to the large loft are 2 bedrooms that share a full bath and another private en-suite bedroom. Recent upgrades include beams on the main level ceiling, beautiful built-in wall unit in the loft, outdoor kitchen and outdoor lighting. Located just minutes from Walt Disney World, premier shopping, dining, and everyday conveniences, and approximately 30 minutes to Orlando International Airport, this beautiful home is perfect for that unbeatable central Florida lifestyle!

9103 Morgana Court, Winter Garden
$499,000
4 Beds ⋅ 4 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code
Wake up to serene pond views and end your evenings watching the magic of fireworks light up the sky — welcome home to 8012 Bluejack Oak. Nestled on a desirable corner lot, this Energy Star Certified townhome offers the perfect blend of comfort, style, and convenience in the sought-after Summerlake community with resort-style amenities. This spacious 4-bedroom, 3.5-bath home was thoughtfully designed for modern living. The heart of the home is a large, open kitchen featuring 42-inch cabinetry, flowing seamlessly into a generous living room — perfect for entertaining. Upstairs, a versatile loft provides additional living space to suit your lifestyle. Retreat to the first-floor primary suite, where a beautifully appointed walk-in shower creates a true spa-like escape. Step outside to your private rear courtyard, ideal for relaxing or hosting guests, with the added convenience of a 2-car garage. Location couldn’t be better — just 10 minutes from Walt Disney World, minutes from the vibrant Hamlin shopping district, and close to the National Golf & Lodge. Whether you’re a theme park enthusiast, an avid golfer, or simply someone who loves a well-connected community, this home checks every box.

8012 Bluejack Oak Drive, Winter Garden
$1,025,000
5 Beds ⋅ 4 Baths ⋅ Sunset Lakes SubDv. ⋅ 34787 Zip Code
Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including the Primary Bedroom), with the 5th Bedroom, a full bath and a bonus loft located on the second level. Inside, the home features designer ENGINEERED HARDWOOD FLOORING throughout the main living areas and the downstairs primary suite. The CHEF'S KITCHEN is a showpiece, boasting THREE SLABS OF PERMIUM CALCUTTA QUARTZ, an ITALIAN MARBLE BACKSPLASH, 60-inch DOUBLE-STACKED ALL WOOD SHAKER CABINTRY, a handy FOOD PREP ISLAND, a BREAKFAST BAR and TOP-OF-THE-LINE SAMSUNG APPLIANCES! The family room features AUTOMATIC ROLLER SHADES and is open to the kitchen and features Cathedral ceilings, a huge picture window and French Doors to the inviting lanai and sparkling pool. The primary suite is a retreat of its own, offering a FULLY-RENOVATED, SPA-INSPIRED bathroom with floor to ceiling CALCUTTA TILE, a frameless glass shower, a freestanding soaking tub, tall custom cabinetry with WHITE EXOTIC CARERRA QUARTZ COUNTERS and a massive walk-in closet! Architectural details elevate every room, including Plantation Shutters, multiple sets of French Doors, tray ceilings, volume and cathedral ceilings, extensive crown molding, transom windows, recessed lighting, bead boarding and elegant custom millwork. Step outside to a stunning outdoor oasis. The completely remodeled pool and spa area is surrounded by 2100 sq. ft. of travertine decking that extends across the covered lanai and additional outside patio space—perfect for entertaining! The lanai ceiling is finished with tongue and groove wood planks, adding warmth and sophistication. Other major upgrades include NEW DOUBLE-PANE, THERMAL WINDOWS (2023), a 2019 ROOF a 2019 AC SYSTEM and rain gutters. The extended brick paver driveway and matching walkway enhance curb appeal, while the well-fed irrigation system coupled with the well water (filtered by the whole house WATER SOFTENER) help keep utility costs low. Note: The wooden planter at the back of the pool and the retaining wall at the back of the lot needs some work and conveys 'AS IS.' All of this is just 5 minutes from the 429, offering quick access to Orlando and surrounding areas. Downtown Winter Garden & Winter Garden Village are also nearby as well as numerous championship golf courses for all your shopping, dining and recreational needs! Nearby top-rated schools are just another plus! Call for your showing today if you want to be the lucky one to snag this one-of-a-kind home before someone else does!

13536 Sunset Lakes Circle, Winter Garden
$714,999
3 Beds ⋅ 2 Baths ⋅ Woodbridge On Green SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring spacious living areas, high ceilings, and thoughtfully designed spaces that make everyday living effortless. The kitchen offers generous counter space, ample cabinetry, and a functional layout perfect for cooking, entertaining, or gathering with family. The primary suite provides a peaceful retreat with a well-appointed bathroom and plenty of closet space. Additional bedrooms are comfortably sized and versatile—ideal for guests, a home office, or a growing household. Outside, enjoy a very large private backyard on the pond, with room to relax, garden, or entertain. New concrete tile roof was installed in 2023. Woodbridge on the Green is known for its mature landscaping (fully HOA maintained), quiet streets, and welcoming atmosphere; the HOA also covers house painting on a rotating schedule, helping to ensure an immaculate community aesthetic. Located just minutes from Windermere, top-rated schools, major highways, and the charming Historic Downtown Winter Garden, this home offers unmatched convenience with shopping, dining, and entertainment right at your fingertips. This is a wonderful opportunity to own a home in one of Winter Garden’s most desirable neighborhoods—move-in ready and full of potential.

14050 Fairway Willow Lane, Winter Garden
$1,000,000
5 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code
Discover refined living in this impressive 5-bedroom, 4-bathroom Spanish-style estate home, beautifully positioned on a serene waterfront lot with peaceful conservation views and nightly Disney fireworks from your own backyard. This exceptional home blends elegance, comfort, and energy efficiency throughout its thoughtfully designed layout. Step through the grand, elegant entrance into a soaring cathedral-ceiling foyer that leads to spacious formal and casual gathering areas. The formal dining room sets the tone for entertaining, while the gourmet kitchen is a true showpiece—featuring an oversized island, dry bar, walk-in pantry, solid wood cabinets, granite countertops, elegant backsplash, and high-end stainless steel appliances. A striking stone accent wall with an electric fireplace adds warmth and style to the main living area, which opens through French doors to breathtaking water and conservation views. The first floor includes a comfortable guest bedroom with a walk-in closet, a full guest bath with convenient pool access, and a luxurious primary suite. The primary bedroom offers a huge walk-in closet, and a spa-inspired ensuite bathroom with garden tub, expansive walk-in shower with multiple rain shower heads, and dual vanities. Upstairs, a spacious loft with surround sound showcases elevated views of the water and conservation area—perfect for a media room or game space. On one side of the loft sits a private bedroom with its own full bath, ideal for guests or extended family. On the opposite side are two additional bedrooms connected by a Jack-and-Jill bathroom, providing comfort and privacy for everyone. Additional highlights include a tile roof, oversized garage, paver driveway, Smart thermostat, water softener and filtration system, and energy-efficient features for year-round comfort. Located in the highly desirable Watermark community, residents enjoy resort-style amenities including a sparkling pool, water park, cabanas, BBQ areas, playground, dog park, tennis and basketball courts, clubhouse with rooftop deck, weekly community activities, fitness center, and scenic walking trails. All of this—just minutes from top-rated schools, dining, shopping, Orange County National Golf Course, and Disney World. A perfect blend of elegance, comfort, and unmatched location—this waterfront estate is truly a must-see.

9207 Busaco Park Way, Winter Garden
$289,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
HUGE PRICE REDUCTION! Welcome to your fully furnished, turn-key 2-bedroom, 2-bath retreat at the Grove Resort & Water Park—just minutes from Disney! Whether you’re searching for the perfect vacation getaway or a smart investment property, this unit has it all. From your private balcony, enjoy peaceful conservation views while knowing your condo is working for you when you’re away. With a strong rental history and enrollment in the resort’s professionally managed short-term rental program, generating income couldn’t be easier. Enjoy the Surfari Water Park, multiple pools, spa, fitness center, restaurants, lakefront pier, and more—everything you and your guests need for a memorable stay. Don’t wait—units like this move quickly! Showings are by appointment only, as this condo is a guest favorite and often booked.

14501 Grove Resort Avenue Unit 3714, Winter Garden
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