Winter Garden Real Estate

Homes for Sale in Winter Garden, FL Between $1,500,000 to $2,000,000

Welcome to your dedicated resource for Homes for Sale Between $1,500,000 to $2,000,000 in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Winter Garden, FL agents, Zen Home Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $1,500,000 to $2,000,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Winter Garden, FL Homes for Sale Between $1,500,000 to $2,000,000

$1,849,000
5 Beds 6 Baths Waterleigh Ph 1 SubDv. 34787 Zip Code
Virtually Staged. SPECTACULAR LAKEFRONT HOME with 99 Feet of Shoreline! Start Enjoying LIFE ON THE LAKE in this Special Home built with the HIGHEST LEVEL OF UPGRADES! Enter this 4,641 sq ft Home with 5 Bedroom Suites and 6 Full Baths through a PRIVATE COURTYARD. Double Doors with Leaded Glass Welcome you to a life of LUXURY! First Floor has Soaring 12 Foot Ceilings, Tray Ceilings, 7 ¼” Baseboards and four Ten Foot Tall Sliders that open to the nearly HALF ACRE Premium Lot with Wide Open Lake Views! Build a DOCK and enjoy Boating, Fishing, Kayaking or try the WATER SKI COURSE on 420 Acre Lake Hickorynut just minutes from DISNEY! Outstanding Features include: Premium Lot that is over 200 Feet Deep, a true GOURMET Kitchen with all WOLF Appliances: Sub-Zero 36” SS Refrigerator, Sub-Zero 36” SS Freezer, Wolf E Series Wall Oven, Convection Steam Oven, Warming Drawer and Wolf Induction Cooktop. The DOUBLE Stacked Raised Panel Cabinetry features a HIDDEN Pantry with CUSTOM Shelving! The Great Room has a Custom Built-In and a Butler Pantry was added near the Dining Room. Oversized Covered Patio is enhanced with Electronic RETRACTABLE Screens, and the Pool Bath is just steps away. Impressive FIRST FLOOR PRIMARY SUITE with Hickory Flooring opens to Spa Bath with DOUBLE Vanities, FREESTANDING TUB, Spacious Shower and Large WALK-IN CUSTOM Closet PLUS a LAUNDRY ROOM with Sink and a STORAGE Closet! Private Suite 2 has Lake Views, Custom Built-In Shelving, Large Bath and Custom Closet. Private Suite 5 overlooks the Courtyard. The CUSTOM Staircase with Oak treads leads upstairs to 2 more Bedroom Suites with 10’ ceilings and Custom Closets, a LARGE Bonus Space wired for SURROUND SOUND is an Ideal THEATER ROOM and a large Covered Balcony with Electronic Screens that is a perfect spot for Relaxing while Enjoying the Sunset over the Lake! Upstairs Laundry Room with original plumbing has been converted to Mini Kitchen – great opportunity for a Mother-In-Law Suite! Outstanding Upgrades Include Engineered Hickory Flooring in entire 2nd Floor and Bedrooms, WATER FILTRATION system, Gutters, Drop Zone with Cabinetry, SOLID CORE Doors throughout home and UV Light in AC Units. Property is very ENERGY EFFICIENT with Double Pane Lo E Windows, Radiant Barrier and Extra Insulation in the Concrete Block. Waterleigh is a Lifestyle Community with 4 Community Pools, 3 Clubhouses with Fitness Centers, Tennis, Pickleball, Mini Golf, Parks, Playgrounds, Community Fishing Dock and MORE! HOA Does all Yard Maintenance. Schools Include Panther Lake Elementary, Water Spring Middle and NEW Horizon High School. Close to Shopping, Dining, NEW Publix, DISNEY and convenient to 429, 1-4 and 417!

8750 Bayview Crossing Drive, Winter Garden

$1,795,000
4 Beds 4 Baths Oakland SubDv. 34787 Zip Code
Welcome to this exceptional ONE-OWNER CUSTOM HOME, sitting on a ONE-ACRE HOMESITE in one of Oakland’s most sought-after locations. Offering 3,515 square feet of living space (4,890 total square feet), this thoughtfully designed 4-bedroom, 3.5-bath residence combines timeless Old Florida charm with OUTSTANDING QUALITY CONSTRUCTION, FEATURING ALL-STEEL CONSTRUCTION—INCLUDING STEEL ROOF TRUSSES—for exceptional durability and peace of mind. A circular driveway and side-entry OVERSIZED TWO-CAR GARAGE create impressive curb appeal, while double front doors welcome you into a spacious, OPEN FLOOR PLAN with 17.5' VAULTED CEILINGS in living area and 10' CEILING HEIGHT in bedrooms.This home has been designed for both everyday living and entertaining. At the heart of the home is a stunning DOUBLE-SIDED FIREPLACE with Tennessee Stone which creates a beautiful focal point between the formal living room and the inviting family room. The living areas flows seamlessly into the kitchen, separated only by a short wall between the kitchen and dining room that preserves the home’s open, airy feel. The EXPANSIVE KITCHEN is designed to bring everyone together, featuring TWO SINKS, a WRAPAROUND BREAKFAST BAR with seating for up to eight, a center ISLAND WITH COOKTOP, generous eat-in dining area, WALK-IN PANTRY with custom built-in shelving, and abundant countertop workspace. The open layout allows the kitchen, dining, and living areas to remain connected, making this home ideal for entertaining, holidays, and family gatherings. The desirable THREE-WAY SPLIT FLOOR PLAN offers both privacy and flexibility. Two secondary bedrooms and a full bath are located toward the front of the home, while a separate guest wing features an additional bedroom, full bath, oversized laundry room with storage, and a convenient half bath. Privately tucked away on the opposite side of the home, the spacious primary suite offers two walk-in closets and an ensuite bath with a walk-in shower. Double glass doors open to an expansive screened lanai that extends the living space outdoors, complete with a summer kitchen and peaceful views of the lush backyard. Additional updates include a tile roof (2015), HVAC ductwork (2020), exterior stucco upgrades and fresh paint (2021), one water heater replaced in 2018 and the second in February 2025, Connection to city water in 2019, The well was retained exclusively for lawn irrigation. Perfectly located with convenient access to the Florida Turnpike, Highway 50, shopping, dining, and area attractions. This meticulously maintained custom home offers the rare combination of quality construction, timeless design, generous living spaces, and an unbeatable Oakland location. This is Florida living at its finest.

15717 E Oakland Avenue, Winter Garden

$1,765,000
5 Beds 4 Baths Oakland Park B-2 SubDv. 34787 Zip Code
Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for entertaining, gas stove, Bosch appliances, pot filler, walk-in pantry, and an appliance garage. The living area flows seamlessly to the outdoors through fully retractable sliding glass doors, complemented by surround sound and custom-tinted windows for comfort and privacy. With 4 bedrooms and 3 full baths—including one with direct patio access—the layout is designed for both convenience and flexibility. One bedroom is located on the main level, while upstairs you’ll find a Jack-and-Jill setup and a spacious primary suite featuring a tray ceiling, spotlight accents, and a spa-inspired bath with walk-in shower, separate soaking tub, and a stunning built-in closet with natural light. An exceptional bonus is the private in-law suite above the garage, complete with its own kitchen, living area, bedroom, and stackable washer/dryer—perfect for guests or multi-generational living. The outdoor oasis is a destination of its own, surrounded by bamboo, olive, lime, and persimmon trees. The covered patio invites year-round enjoyment, and the fully fenced property offers privacy and space to unwind. From your backyard, you can even watch Space Shuttle launches light up the sky. Located in the highly desirable golf cart district, this home places you just a 2-minute walk from the West Orange Trail and only 3 miles from historic Downtown Winter Garden. Unbeatable location, unmatched lifestyle. Schedule your private showing today.

906 Allendale Lane, Winter Garden

$1,740,000
5 Beds 6 Baths Lake Star/Ovation Ph 1b SubDv. 34787 Zip Code
Price Improvement | One of Horizon West's Most Exclusive Luxury Lakefront Homes Luxury lakefront living at its absolute finest in the heart of Horizon West Ovation. This is a rare opportunity to own one of the most impressive homes in the entire community, now offered at a newly improved price. If you have been waiting for a home that combines luxury, space, privacy, breathtaking views, and exceptional value, this is the opportunity you have been looking for. Built with the builder's largest and most prestigious floor plan, this nearly new residence offers 5 spacious bedrooms, 5 full bathrooms, 1 powder room, and nearly 5,000 square feet of beautifully designed living space where elegance and comfort come together effortlessly. Situated on an oversized premium homesite with exceptional distance from neighboring homes, this property provides a level of privacy rarely found in Central Florida. From the moment you walk through the front door, you are welcomed by stunning lake and conservation views that create an atmosphere of peace, beauty, and exclusivity. What truly makes this home special is something that very few properties in Ovation can offer. This is one of the only homes in the community with direct access to a navigable lake, allowing you to enjoy a true waterfront lifestyle right from your own backyard. Imagine launching a kayak or paddleboard whenever you want, relaxing by the water at sunset, or enjoying Disney fireworks from your private balcony. It is a lifestyle that simply cannot be replicated. To help you visualize the incredible possibilities, two professionally designed 3D renderings are included with the listing, showcasing the potential for a spectacular custom pool and private lakefront deck. This property offers the perfect setting to create one of the most beautiful outdoor living spaces in Horizon West. Inside, every detail reflects quality and thoughtful design. The finishes are comparable to the builder's model home and include expansive open living areas, soaring ceilings filled with natural light, premium flooring, designer finishes, and a stunning gourmet kitchen that is perfect for entertaining or everyday living. The bedrooms are exceptionally spacious, providing comfort for family and guests alike. The oversized laundry room offers abundant cabinetry and a utility sink for added convenience. The owner's suite is a true private retreat, featuring an extended balcony overlooking the lake and conservation area, where you can enjoy breathtaking sunsets and Disney fireworks from the comfort of your own home. Located in the highly desirable Horizon West Ovation community, this home is only minutes from Walt Disney World, top rated schools, shopping, restaurants, entertainment, and major highways, while still offering the tranquility of a luxury waterfront setting. With its recent price improvement, this home represents one of the finest luxury values currently available in Horizon West. Opportunities like this rarely come to market, especially a home offering nearly 5,000 square feet, one of the community's premier floor plans, direct access to a navigable lake, breathtaking views, and the opportunity to build your dream pool and private waterfront deck. Do not miss your chance to own one of the most exclusive waterfront homes in Horizon West. Schedule your private showing today and experience everything this extraordinary property has to offer before someone else does.

17372 Glossy Pomelo Way, Winter Garden

$1,699,000
5 Beds 5 Baths Hull Island/Oakland SubDv. 34787 Zip Code
Virtually Staged. Welcome to this exceptional lakefront retreat on the shores of Lake Apopka, where breathtaking water views, luxury upgrades, and exceptional outdoor living come together to create the ultimate Florida lifestyle. Offering 5 bedrooms, 4.5 bathrooms, and over 4,000 square feet of thoughtfully designed living space, including a convenient first-floor bedroom, this beautifully updated residence showcases more than $500,000 in improvements, creating a move-in-ready experience for the next owner. From the moment you arrive, you'll appreciate the extensive upgrades throughout the home, including porcelain tile throughout the main living areas on the first floor, engineered white oak hardwood flooring throughout the second level, a custom wood and iron staircase, upgraded cabinetry, quartz countertops, designer finishes, and a beautifully appointed kitchen featuring premium KitchenAid appliances, a gas cooktop, and custom soft-close cabinetry. Designed for both everyday living and entertaining, the backyard is a true showpiece. Enjoy a resort-style saltwater pool and spa, gas-heated for year-round enjoyment, expansive outdoor living areas, and a fully equipped summer kitchen featuring premium Blaze appliances. Electric screens allow you to enjoy outdoor dining and entertaining comfortably while taking in the peaceful lakefront setting and stunning sunset views. Boating enthusiasts will appreciate the private dock complete with a 5,000-pound boat lift, offering direct access to Lake Apopka, one of Florida's largest lakes. With more than 30,000 acres of open water to explore, the lake offers endless opportunities for boating, fishing, watersports, and unforgettable sunset cruises. Known for its trophy bass fishing, abundant wildlife, and expansive waterfront views, Lake Apopka provides a rare opportunity to enjoy true lakefront living with the freedom and space that few Central Florida lakes can offer. This property delivers the waterfront lifestyle Florida is known for. Additional highlights include a convenient first-floor bedroom, a second-floor laundry room, solar panels that will be paid off at closing, natural gas service, a Culligan water filtration system, dual pool pumps, and city sewer, a significant advantage for a waterfront property. Ideally located just minutes from Downtown Winter Garden, shopping, dining, and major roadways, this exceptional lakefront residence offers the perfect balance of luxury, recreation, and everyday convenience.

1144 Hull Island Drive, Winter Garden

$1,675,000
5 Beds 4 Baths Lakeview Reserve SubDv. 34787 Zip Code
An unparalleled lakefront opportunity in Downtown Winter Garden **Seize the rare chance to own a premier waterfront estate where the true value lies in the spectacular lot, private dock, and an enviable golf-cart lifestyle ** Launch your boat from your private lift for a scenic 30-minute cruise to Mt. Dora or take your golf cart just minutes away to the historic downtown Farmers’ Market and restaurants **Positioned within a private, gated enclave directly across from the West Orange Trail, this property offers the ultimate Florida resort lifestyle outside, featuring a heated saltwater pool, raised spa, and a fully fenced, expansive lakeside yard ** Inside, the home boasts a massive primary suite +/16x26’ with tray ceiling, fireplace and a balcony with lovely lake views and massive +/-23x25 bonus room including a wet bar and fireplace** The kitchen has a large cooking island w/sink plus a separate breakfast bar, stone counters, under cabinet lighting, a Jenn-Air double convection oven and lovely dining area overlooking the lake ** There's even an open wine closet/alcove with wine refrigerator off the kitchen ** First floor bedroom with an oversized walk in closet as a 5th bedroom or den (currently being used as a dining room) ** Other home upgrades include a newer roof +/-2022, 3 newer A/C units, a whole-home Katolight 40KW generator that runs +/- 90% of the home, crown molding throughout the home, ADT security system with cameras, boat house with new roof 2025, resurfaced pool +/-5 yrs ago & Aqualink pool/spa automation system and a 10’ seawall ** Relax on the covered screened patio with the Bose speaker system and prime outdoor living space including additional yard space beyond the pool and patio ** 2 car garage plus a 1 car garage with easy access to the back yard perfect for bringing your boat or lawn equipment through ** LOW HOA fees $200 quarterly ** All room measurements in MLS and on 3d floorplan are approximate. Buyer to verify. Tax record is incorrect - property has 5 bedrooms. Dock measurement is estimated. Buyer to verify. Solar panel lease to be transferred to buyer at closing.

279 Zachary Wade Street, Winter Garden

$1,649,999
6 Beds 5 Baths Oakland Park SubDv. 34787 Zip Code
Virtually Staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36” dual-fuel range, warming oven, and a 48” side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner’s suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home’s charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.

1101 Eagles Pass Way, Winter Garden

$1,600,000
5 Beds 5 Baths Winter Grv SubDv. 34787 Zip Code
Welcome to Winter Grove in the charming city of Winter Garden. Ideally located just 1.2 miles from Winter Garden Village and approximately 2.8 miles from Historic Downtown Winter Garden, this intimate gated community offers the perfect blend of luxury, convenience, and privacy. Featuring spacious homesites and no CDD, residents enjoy easy access to premier shopping, dining, entertainment, and everything that makes this one of Central Florida’s most sought-after locations. Introducing the stunning Roseland model, a beautifully designed 5-bedroom, 5-bathroom residence with a 3-car garage, offering an exceptional balance of elegance, functionality, and thoughtfully curated finishes throughout. As you step through the impressive double glass entry doors, you are welcomed by a dramatic two-story foyer that immediately creates a grand first impression. Just off the entrance, an enclosed flex room provides endless possibilities—ideal as a home office, fitness room or additional living space—while the formal dining room creates the perfect setting for entertaining. Continuing through the home, a striking staircase featuring engineered hardwood plank treads and wrought iron balusters enhances the sophisticated design. Tucked beneath the staircase is a wine lover’s dream: a stylish wine cave complete with built-in cabinetry, quartz countertops, and designer tile backsplash. At the heart of the home, the open-concept kitchen is designed to impress, featuring built-in KitchenAid stainless steel appliances, including a gas-cooktop, oven, and beverage cooler. Beautiful two-tone soft-close cabinetry is paired with elegant quartz countertops, creating a timeless and refined aesthetic, while a spacious walk-in pantry provides abundant storage. The seamless flow between the kitchen, café, and gathering room creates an inviting and light-filled space, ideal for both everyday living and entertaining. Sliding doors lead to the covered lanai, which has already been pre-plumbed and pre-wired for a future outdoor kitchen, including electric, water, sewer, and natural gas connections—allowing the future owner to easily create their dream outdoor living space. Also located on the first floor is a spacious Multi-Gen Suite, perfect for guests or multigenerational living, complete with a walk-in closet and private bathroom. Upstairs, the luxurious owner’s suite occupies its own private wing, creating a peaceful retreat. An additional sitting area provides the perfect place to unwind or enjoy quiet moments. The spa-inspired owner’s bath showcases a freestanding soaking tub, oversized frameless glass shower and generous dual walk-in closets. The second floor also features additional well-appointed bedrooms, including two connected by a Jack-and-Jill bathroom and another with its own private en-suite bath, offering both comfort and privacy for family and guests. The upstairs laundry room, complete with cabinetry and a utility sink with quartz finishes, adds everyday convenience. Residents of Winter Grove also enjoy access to community amenities including a beautiful pond with walking trails. With an intelligently designed floor plan, carefully selected finishes, and a highly desirable location, this exceptional home offers the perfect blend of luxury, comfort, and lifestyle. Schedule your private tour today and experience this extraordinary home has to offer.

325 Crystal Wood Drive, Winter Garden

$1,599,999
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

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