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16098 Johns Lake Overlook Drive, Winter Garden
$2,125,000
5 Beds ⋅ 5 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code
This LAKEFRONT Home with PRIMARY AND 3 SECONDARY BEDROOMS ON the MAIN FLOOR was RENOVATED FROM TOP TO BOTTOM and is located in the very desirable GATED Community of HICKORY HAMMOCK. The moment you walk through the front door, you will have gorgeous VIEWS OF THE BEAUTIFUL 2400-ACRE JOHN’S LAKE. The interior continues with the COUNTLESS UPDATED CUSTOM FINISHES including VERY HIGH-END LUXURY VINYL PLANK FLOORING throughout the entire first floor, QUARTZ COUNTERTOPS, 53” EUROPEAN-STYLE KITCHEN CABINETS, TWO-PIECE CROWN MOLDING, and 7” BASE MOLDING. ALL 5 BEDROOMS HAVE WALK-IN CLOSESTS WITH CUSTOM BUILT-INS. You will find one additional Bedroom and Full Bathroom upstairs alongside a HUGE BONUS ROOM with plush carpet and extra thick padding. Entering the home from the garage, you will find a beautifully designed MUD SPACE and then enter the laundry room to find a BUILT-IN SMOOTHIE/COFFEE BAR with upper and lower cabinets, drawers, and a BUILT-IN SINK. There’s also an ingenious “SECRET” SPACE that’s currently being used as an art room. The home features a whole-home filtration/softener and R.O. water system. Alarm system and cameras are paid in full and included. Additionally, this home provides a SCREENED-IN SALTWATER POOL. Inside the screened patio, you’ll enjoy entertaining with a SUMMER KITCHEN, complete with a built-in grill, refrigerator, sink, and granite countertop. This home provides extraordinary entertaining space, both inside and out. This home also features an OVERSIZED 3-car garage with Lots of OVERHEAD STORAGE RACKS and a SPLIT AIR CONDITIONER. The PRIVATE DOCK IS EQUIPPED WITH WATER AND ELECTRICITY AND BOAT LIFT. There is a FULLY FENCED backyard leading to your dock where you can watch DISNEY FIREWORKS OR GO ENJOY BOATING, PADDLE BOARDING, KAYAKING, OR JET SKIING ON THE INCREDIBLE 2400 ACRE JOHN’S LAKE. *BONUS - SOLAR PANELS ARE OWNED – NO ADDITIONAL PAYMENTS – SAVE MONEY ON YOUR ELECTRIC BILL* THIS EXCEPTIONALLY DESIGNED AND UPDATED LAKEFRONT HOME TRULY OFFERS IT ALL. Schedule your private showing today.

16098 Johns Lake Overlook Drive, Winter Garden

15783 Tangerine Dream Court, Winter Garden
$2,100,000
5 Beds ⋅ 6 Baths ⋅ Hickory Hammock Emerald Pointe SubDv. ⋅ 34787 Zip Code
LUXURY ISLAND HOME IN POPULAR GATED COMMUNITY. Experience modern lakefront luxury in Emerald Point, an exclusive gated island of only 28 homes within the desirable Hickory Hammock community, offering a rare blend of luxury, privacy and premium lakefront living. Perfectly positioned on Johns Lake, this contemporary two-story home showcases clean architectural lines, sophisticated finishes, and breathtaking water views, offering the ultimate in Florida living. Privacy and serenity are exceptional with wide lake views from nearly every room and a charming, landscaped park with towering oaks directly across the street. From the moment you enter, a dramatic two-story foyer with upgraded crystal light fixtures and a striking clear view of the lake sets the tone for this modern masterpiece. The formal dining area flows seamlessly into the expansive great room, where an open concept design, stacked stone accent wall, and a rear wall of stackable sliding glass doors creating a true indoor-outdoor living experience. The oversized gourmet kitchen is a chef’s dream, featuring dual islands, pot filler, built-in side-by-side stainless steel refrigerator and freezer, double ovens with convection, built-in microwave, and a dedicated wine and beverage cooler. White shaker cabinetry with illuminated glass inserts, crown molding, quartz countertops, glass tile backsplash, and an oversized walk-in pantry elevate the space. The breakfast nook is perfectly positioned to capture tranquil lake views with every meal. The main level offers a thoughtfully placed half bath for guests, along with a private guest suite featuring sliding doors to the covered lanai and an ensuite bath, ideal for extended stays or multigenerational living. Upstairs, modern glass and stainless-steel railing lead to a spacious bonus room with a full wet bar and additional wine and beverage cooler. This impressive entertaining space opens to a generous balcony with sweeping, unobstructed views of Johns Lake. A convenient laundry room with LG washer and dryer and a second half bath add to the home’s functionality. The primary suite is a serene lakefront retreat, boasting dual walk-in closets, private balcony overlooking Johns Lake, and a spa-inspired ensuite with oversized walk-in shower with rain shower head, garden tub, and dual quartz vanities. Three additional upstairs bedrooms include generous closets, ceiling fans, and either ensuite or Jack-and-Jill baths with tile flooring, quartz counters, and tub/shower combinations; perfect for family or guests. Modern conveniences abound, including a Nest home system, motorized rolling shades, whole-house water filtration with reverse osmosis, and an oversized 3-car garage. The east-facing rear yard offers approximately 102 feet of lake frontage, thoughtfully oriented to avoid the harsh afternoon sun while maximizing shimmering water views throughout the day. Residents of Hickory Hammock enjoy resort-style amenities including a zero-entry pool, clubhouse, fitness center, tennis and volleyball courts, fishing pier, playgrounds, walking trails, and a dog park. Located just minutes from historic Downtown Winter Garden, Winter Garden Village, area attractions, Disney, and Orlando International Airport, this residence perfectly blends contemporary design, lakefront luxury, and everyday convenience. Schedule your private showing today and experience lakefront sophistication at Emerald Point at Hickory Hammock.

15783 Tangerine Dream Court, Winter Garden

5340 Bowman Drive, Winter Garden
$2,050,000
5 Beds ⋅ 7 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code
Lakefront living, done at scale. Set along approximately 160 feet of shoreline on Lake Hancock, this five-bedroom, six-and-a-half-bath residence delivers expansive water views, refined finishes, and a layout designed for both everyday living and effortless entertaining. From the moment you enter, soaring ceilings, arched architectural details, and wide-plank hardwood floors create a sense of openness and flow. A wall of arched windows floods the home with natural light and draws your eye straight through to the lake beyond. At the center, a chef’s kitchen anchors the space—featuring a generous island, porcelain farm sink, custom cabinetry, glass tile backsplash, and a full suite of Wolf and Sub-Zero appliances. The kitchen opens seamlessly to the family room and breakfast area, all positioned to capture the view. The primary suite is tucked privately on the main level, offering a true retreat with tranquil lake views, a spa-style bath with soaking tub and walk-in shower, dual vanities, and an oversized closet. Upstairs, four additional bedrooms with en-suite baths are complemented by a spacious game room and dedicated media room—creating separation and flexibility for guests or family. Outdoor living is just as compelling. A covered lanai and upper-level balcony overlook the water, with ample space to design a custom pool and private dock. Located near Hamlin Town Center, Winter Garden Village, and major roadways, the home offers both convenience and a true waterfront lifestyle, with community amenities including a pool, fitness center, playgrounds, and dock access

5340 Bowman Drive, Winter Garden

1017 Johns Point Drive, Oakland
$2,050,000
5 Beds ⋅ 6 Baths ⋅ Johns Cove 43/104 SubDv. ⋅ 34787 Zip Code
A rare lakefront estate on one of Central Florida?s most celebrated lakes, John?s Lake. Positioned on nearly one acre in a private, gated enclave, this custom 5-bedroom, 6-bath residence offers sweeping open-water views, dramatic sunsets, and direct access to boating, jet skiing, and year-round fishing from its private dock. With approximately 250 feet of pristine shoreline, this home delivers lakefront living at its finest. Inside, the residence features soaring 11-foot ceilings, elegant architectural details, and refined formal living and dining spaces. The beautifully updated gourmet kitchen includes high-end stainless-steel appliances, granite countertops, custom cabinetry, dual center islands, and a spacious walk-in pantry. An entertainment lounge with a wet bar, dishwasher, ice maker, under-counter refrigerator, and dual beer taps creates an exceptional setting for hosting. Notably, in 2024, the homeowner replaced two first-floor air-conditioning units, ensuring modern comfort and efficiency. The luxurious first-floor owner?s suite offers direct lanai access, a cozy fireplace, two custom California Closets, and a spa-inspired bath. Additional first-floor amenities include a private guest suite, an executive office, a fitness room, and a well-appointed laundry room. Upstairs, three generously sized bedrooms each feature private baths and walk-in closets, with two enjoying beautiful lake views. Outdoor living is truly exceptional, with a fully screened custom pool featuring water elements, an expansive brick-paver lanai, lush landscaping, and a private dock equipped with an electric boat lift, dual jet ski lift, floating dock, screened sitting area, and full power and water connections. This property is not only a rare lakefront masterpiece but also an outstanding value for those seeking luxurious living. With the recent 2024 upgrade of the first-floor air-conditioning units, it offers an exceptional blend of elegance, comfort, and an unbeatable lakefront lifestyle?an ideal opportunity for discerning buyers looking for a home that delivers both luxury and remarkable value.

1017 Johns Point Drive, Oakland

9008 Morgana Court, Winter Garden
$2,050,000
5 Beds ⋅ 5 Baths ⋅ Avalon Cove SubDv. ⋅ 34787 Zip Code
Set along the shoreline of Lake Hickorynut in Avalon Cove, this 2022-built lakefront residence blends refined design with the ease of modern Florida living. Positioned on a cul-de-sac corner lot of approximately 0.35 acres, the home offers long, open-water views and a lifestyle centered around indoor–outdoor connection, afternoon breezes off the lake, and sunsets enjoyed from the covered balcony or the resort-style pool terrace. The home spans approximately 4,934 square feet of living space (total 6,907 square feet), with five bedrooms and five full baths, and features tall ceilings, expansive windows, and sliding glass doors that frame the water view from the main living areas. The main level includes an open kitchen with upgraded cabinetry, soft-close doors and drawers, an oversized island, a natural-gas cooktop, a walk-in pantry, and a glass-enclosed wine room. An electric fireplace anchors the family room, and double sliding barn doors open to a dedicated theater room equipped with a projector, automated screen, and integrated sound. A first-floor guest suite with a walk-in closet and an additional full bath is perfect for visitors or multi-generational living. A large flex space, currently used as a gym, completes the first floor. Upstairs, a spacious loft with custom cabinetry, beverage drawers, and a triple-TV setup leads to the 40-foot covered balcony overlooking the lake — perfect for enjoying the sunset. The primary suite shares the same view and offers a large spa-style bath with a freestanding tub, an oversized shower with multiple shower heads, dual sinks, and a walk-in closet with built-in storage and direct access to the laundry room. Three additional bedrooms and two more full baths are also located on this level. The fenced backyard is designed for low-maintenance year-round enjoyment, featuring turf, lush landscaping, and a custom outdoor kitchen under the covered lanai. The natural-gas heated pool includes a waterfall, bubbler, oversized spa, built-in table with umbrella, sun shelf, lighting, auto-fill and drain, and complete smartphone control. A composite, covered dock — built in 2022 — extends the lifestyle onto the water with a boat lift, electricity, water, and rail lighting. Additional features include an EV charging station in the oversized three-car garage, custom garage cabinetry with a dedicated workbench, plantation shutters, upgraded tile plank flooring on the first floor with hardwood upstairs, a tile roof, smart-home systems (Control4, Lutron lighting, and Sonos), a water filtration system with reverse osmosis, and a security system with video capability. Located minutes from great schools, dining, parks, and attractions in Horizon West, this lakefront home offers both privacy and connection in one of Winter Garden’s most desirable areas.

9008 Morgana Court, Winter Garden

811 Civitas Way, Winter Garden
$2,040,000
4 Beds ⋅ 5 Baths ⋅ Oakland Park Un # 2a SubDv. ⋅ 34787 Zip Code
Price Improvement!!! Experience elevated living in this exceptional custom home by J&J Building, perfectly positioned in one of Winter Garden’s most desirable locations directly across from the iconic West Orange Trail. Offering over 5,000 square feet of thoughtfully designed luxury, 811 Civitas Way blends sophisticated style, flexible living spaces, and impressive functionality rarely found in today’s market. Designed for both everyday comfort and unforgettable entertaining, the home features a truly jaw-dropping media room that delivers the ultimate cinematic experience. Multiple office and flex space options provide incredible versatility for remote work, creative pursuits, fitness, or multigenerational living. With bedrooms thoughtfully positioned on both the first and second floors, the layout offers ideal privacy and convenience for guests and family alike. Luxury details and custom upgrades are showcased throughout, including a whole-home generator, a one-year-old Sub-Zero refrigerator, two stunning crystal chandeliers installed last year, and elegant solid brass door hardware throughout the home. You'll fall in love with the large island in the garage that even includes a built-in gift wrapping station! Every space reflects exceptional craftsmanship and thoughtful design, with countless additional custom touches that elevate the home’s overall sophistication and character. One of the property’s standout features is its exceptionally rare amount of parking for 7 cars plus a golf cart— a coveted luxury that sets this home apart. Combined with its prime location near Downtown Winter Garden, scenic trail access, dining, shopping, and commuter routes, this residence offers a lifestyle that is as refined as it is practical. **There is room to add a pool and ADU on this lot, as well! Artist renderings with the pool included in the photos.

811 Civitas Way, Winter Garden

15555 Panther Lake Drive, Winter Garden
$2,025,000
5 Beds ⋅ 6 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Award-Winning Toll Brothers Model Home on the Lake | Infinity Pool + Designer Estate Welcome to luxury waterfront living in the highly sought-after Panther Lake community in Winter Garden. This award-winning Maranello model sites on a premium lakefront homesite and is designed for both elevated everyday living and effortless entertaining, the home showcases expansive open living areas, designer finishes, and seamless indoor-outdoor flow. Property Highlights & Amenities: * Seller pays $10,000.00 towards buyer's closing costs * Infinity pool with heated spa providing breathtaking water views * Large pocket sliders create a true open-air living experience, connecting the living and dining spaces with the pool, lanai, and lake * Private mother-in-law suite offering a comfortable and private retreat for guests or extended family, ideal for multi-generational living or a quiet home office * Chef’s kitchen with JennAir appliances designed for both everyday living and elevated entertaining * Top rated schools a bike ride from Independence Elementary School and Horizon High School * Outdoor living with a fully equipped kitchen, fireplace, fire pit and TV creating a complete outdoor living space perfect for hosting or relaxing year-round * Private balcony with expansive views of the Lake, pool and community * Butler’s kitchen providing additional prep space, storage, and functionality for seamless entertaining * Spacious loft with built-ins and workspace offering flexible space for work, study, or casual gathering * First-floor primary suite with spa-style bath and walk-in closet creating a private retreat with comfort and convenience on the main level * Professionally designed model home finishes throughout delivering a cohesive, high-end aesthetic in every space * Furnishings convey, presenting an opportunity to acquire the home’s professionally curated design elements. Enjoy access to Panther Lake’s resort-style community amenities, including a clubhouse with event space for private parties and receptions, fitness center, community pool, playground, walking trails, and a private dock with canoe/kayak storage—perfect for embracing the lakefront lifestyle. A rare opportunity to own a premier waterfront model home with resort-style amenities - this home delivers the perfect blend of privacy, luxury, and convenience. Schedule your private showing today.

15555 Panther Lake Drive, Winter Garden

770 W Bay Street, Winter Garden
$2,010,000
34787 Zip Code
Amazing warehouse located blocks from Downtown Winter Garden. The warehouse is currently broken up into 3 spaces plus 2200 square feet of A office space. The building is completely in grated with cameras, door lock and lighting in the office space. There is also a sound booth if needed. The property does have fire sprinkler system, 3 phase electrical, insulated. Office space has been completely updated there is a kitchen and 4 baths in the office, and additional bath in the warehouse. This property is set for an owner user or value add with rent way below market value all tenants are on a month to month! This property is easy access to Highway 50, 429, 408 and Florida Turnpike and blocks from Downtown Winter Garden were prices per sq ft are reaching a $900 per sq ft. This property is price for a Quick Sale! Do Not Miss the Deal of a Lifetime!

770 W Bay Street, Winter Garden

20 W Crest Avenue, Winter Garden
$2,000,000
5 Beds ⋅ 5 Baths ⋅ Boyd-Lutz Sub SubDv. ⋅ 34787 Zip Code
Virtually Staged. Built by the owner with uncompromising construction standards, this Winter Garden masterpiece delivers the kind of quality and engineering you simply don’t find in today’s market. And with the seller just reducing the price, this luxury home is now an even more exceptional opportunity. Custom built pool renderings and pricing available. Concrete structural design, hurricane-rated engineering, impact windows, full foam insulation, fiber-cement siding, and an Ipe hardwood porch set the tone for durability and refinement. Inside, natural light pours across level-5 walls, rich wood flooring, crown molding, and custom shutters—creating a warm, polished, magazine-worthy aesthetic. The open living and chef’s kitchen are built for elevated living: gas range, pot filler, handcrafted cabinetry, and a dramatic retractable pocket door that dissolves the boundary between indoors and out. The resort-style back porch is a showpiece—pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, and a half bath—perfect for hosting unforgettable evenings. The primary suite is pure indulgence, featuring a spa-inspired bath with dual shower heads, soaking tub, digital controls, a custom closet, and a private concrete safe room. A butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring elevate everyday convenience. Upstairs, the bonus/game room and oversized balcony create a luxe hangout zone. Storage is abundant with walk-in closets throughout. And the finished two-story garage loft—pre-plumbed and air-conditioned—offers endless possibilities: in-law suite, golf simulator lounge, gym, office, or creative studio. Outside, curated landscaping, gas lanterns, an architectural driveway, and a heated concrete hot tub with Wi-Fi controls complete the experience. All just moments from Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre. Craftsmanship, luxury, and location—now at an even more compelling price.

20 W Crest Avenue, Winter Garden

14640 Pylon Court, Winter Garden
$2,000,000
5 Beds ⋅ 6 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code
Welcome to 14640 Pylon Court, an extraordinary waterfront home located in the highly sought after gated community of the Isles of Lake Hancock—one of Florida’s most exclusive water ski neighborhoods. This custom-designed residence offers over 4,400 square feet of luxurious living space, five bedrooms, five full and one-half baths, a 4-car garage, and sweeping water views from both the front and back of the home. Set on a premium lot with direct views of the world-renowned championship ski courses, this home offers the ultimate blend of privacy, elegance, and recreational lifestyle. Inside, rich hardwood flooring flows through spacious, light-filled living areas, including a formal dining room with detailed ceilings, a private study, and a great room with soaring ceilings, custom built-ins, a fireplace, and expansive sliding glass doors. The gourmet kitchen features a massive island, gas appliances, double ovens, and ample cabinetry—perfect for both casual family living and entertaining on a grand scale. The luxurious primary suite includes a sitting area with lake views, dual walk-in closets, a soaking tub, walk-in shower, and dual vanities. The first-floor media room offers the perfect space for movie nights or game-day gatherings, while two additional bedrooms and a balcony complete the home’s thoughtful layout. The expansive screened lanai is ideal for outdoor living, featuring a sparkling pool, summer kitchen, manicured grounds, and tranquil water vistas. As a resident of this exclusive 54-home community, you’ll enjoy access to a residents-only boat ramp, tennis courts, playground, and recreation area. Located just minutes from all of the shopping and amenities at Hamlin, yet tucked away in a quiet, gated enclave, this home offers a rare opportunity to own one of Central Florida’s most sought-after waterfront properties—where luxury meets lifestyle.

14640 Pylon Court, Winter Garden

4230 Rex Drive, Winter Garden
$2,000,000
9 Beds ⋅ 6 Baths ⋅ Lake Avalon Grvs 2nd Rep SubDv. ⋅ 34787 Zip Code
**A RARE OPPORTUNITY YOU WON’T WANT TO MISS!!** 9.75 PRIME ACRES IN THE HEART OF WINTER GARDEN ~ MAIN HOME CUSTOM BUILT BY HANNIGAN HOMES 5BD/4BA/3-CAR- 5,423 SQFT, INCLUDING AN ABOVE GARAGE APARTMENT WITH 1/BD/1/BA/+KITCHENETTE ~ SECOND HOME ON PROPERTY INCLUDES 4BD/2BA/2-CAR - 2,082SQFT ~ 10-STALL + TACKROOM HORSE BARN - 2,592 SQFT, 3 PASTURES ~ FENCED IN RIDING RING AND MUCH MORE! This countryside estate is an exclusive opportunity to own two homes, a horse barn, an adorable chicken coop, Koi pond, paver fire pit, built-in playground and so much more in the heart of the sought-after Winter Garden! Bring your horses and enjoy all that this massive CORNER LOT has to offer and being just minutes from the 429 gives you easy access to every convenience including neighboring HORIZON WEST and DISNEY THEME PARKS. Being sold all as one gives you endless opportunities in the ADDITIONAL SINGLE FAMILY HOME with the main home ready with charm for a family to make it their own. The long covered front porch welcomes you home and gives you front row seats to the riding ring. Built by Hannigan Homes, the main home was modeled after Disney’s Grand Floridian, and the thoughtful and unique features throughout are the perfect blend of comfort and quiet luxury. The roof was updated in 2019, the office space can serve as an additional bedroom, light and bright with views of the property, there is a movie/media room currently being used as an indoor trampoline park, WALK-IN WINE CELLAR for the adults, a fun HIDDEN WALK-IN PANTRY for ample kitchen storage and an energy saving SOLAR WATER HEATER. The new owner will absolutely fall in love with the PRIVATE PRIMARY SUITE that takes up the entirety of the second floor with sweeping views overlooking your estate, large WALK-IN CLOSET and well appointed ensuite bath. The additional bedrooms on the main floor give room to grow, and the additional home and garage apartment graciously allow for multi-general living. This gorgeous property is best experienced in person (stunning sunsets included!) so it can speak for itself - call today to schedule your private tour today!

4230 Rex Drive, Winter Garden

9014 Morgana Court, Winter Garden
$1,990,000
5 Beds ⋅ 5 Baths ⋅ Avalon Cove SubDv. ⋅ 34787 Zip Code
This is more than a house ~ Lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare “water-on-water” moment – breathtaking panoramic lake views that frame the entire living space and set the tone for everything that follows. Designed for effortless living and unforgettable entertaining, Come home and immediately dive into the lake life. Expansive sliding glass doors dissolve the line between indoors and out, opening to a resort-style backyard featuring a saltwater pool, heated spa, pool ledge loungers, integrated lighting, and a pool crawler cleaning system. Motorized lanai screens, a built-in outdoor kitchen with gas grill, and a gas fire pit creating the ultimate sunset and entertainment zone – complete with water views and space to gather - there or on your private dock! Inside, the chef’s kitchen anchors the home with an oversized island seating up to eight, custom wood vent hood, gas cooktop, designer finishes, barn door accents, and thoughtful upgrades throughout. Custom wood beams add warmth and architectural interest, while the open layout flows seamlessly to living, dining, and outdoor spaces – ideal for hosting or relaxing in style. Luxury meets intelligence with over $30,000 in smart home upgrades, including full Alarm automation, indoor and outdoor security cameras, remote access controls, Sonos audio, and Bluetooth sound zones throughout the kitchen, living room, loft, lanai, and balcony. Motorized shades on both floors provide privacy and convenience at the touch of a button. A reverse osmosis water system enhances everyday living, and the first-floor laundry adds to the home’s thoughtful functionality. Both primary suites are beautiful, a spa-inspired primary bath, and a custom walk-in closet. A dedicated gaming room offers a turnkey entertainment space – perfect for family & friends fun for all ages. Step onto the front-facing balcony in the evenings and enjoy nightly Disney fireworks, a magical reminder of how close you are to it all. The epoxy-finished three-car garage includes an additional storage bay, offering space for vehicles, toys, and lake-life essentials. Outside, low-maintenance AstroTurf landscaping keeps the focus on enjoyment, not upkeep. Just minutes from Disney theme parks, shopping, dining, and with easy access to SR-429, this home is approximately 30–40 minutes from Orlando International Airport, making it ideal as a primary residence, second home, or luxury retreat. Comfortable, elevated, and completely move-in ready – this is lakefront living done right! Call today to schedule your tour and let us welcome you home!

9014 Morgana Court, Winter Garden

7757 Summerlake Pointe Boulevard, Winter Garden
$1,980,000
4 Beds ⋅ 4 Baths ⋅ Summerlake Pd Ph 1b A Rep SubDv. ⋅ 34787 Zip Code
Stunning custom-built lakefront pool home on Lake Hancock offering luxury, comfort, and breathtaking views from nearly every room. Designed for entertaining, this remarkable residence features a chef’s dream kitchen with a wrap-around bar, center island, Bertazzoni 5-burner gas range, double ovens, walk-in pantry, granite countertops, stainless steel appliances, and a stylish tile backsplash. The open living and family rooms flow seamlessly to the spacious lanai through elegant French doors, complete with retractable screens and a built-in gas grill for effortless indoor-outdoor living. The luxurious downstairs primary suite boasts a custom tray ceiling, spa-inspired bath with dual vanities, walk-in shower, large soaking tub, and spacious walk-in closets, with direct access to the lanai and pool. Upstairs, a screened lanai accessible from the bedroom, den/office, and gallery provides stunning lake views. Relax in the heated pool and spa with outdoor shower, or follow the travertine walkway to the private boat dock equipped with electronic lifts for a boat and jet ski. Architectural details include high ceilings, custom crown molding, and elegant curved walls in the breakfast nook and primary bath. Set on 1.64 acres of professionally landscaped and fenced grounds, a portion extending into the lake, this home also enjoys access to the desirable Summerlake community with a resort-style clubhouse, pool, tennis courts, fitness center, park, dog park, and playground — the perfect blend of elegance, comfort, and Florida lakefront living.

7757 Summerlake Pointe Boulevard, Winter Garden

15986 Johns Lake Overlook Drive, Winter Garden
$1,962,500
5 Beds ⋅ 6 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code
Experience breathtaking lakefront living in this exceptional estate home with a private dock in one of Winter Garden’s most sought-after gated communities: Hickory Hammock at Johns Lake. Perfectly positioned on the shores of Johns Lake, this spacious 5-bedroom, 4 full-bath, 2 half-bath residence offers the ideal combination of elegance, comfort, and outdoor adventure. Whether unwinding on the dock at sunset, setting out for a day of boating and fishing, or simply enjoying the serenity of the water from the private backyard, this home provides a rare opportunity to embrace the Florida lifestyle. Designed for both entertaining and everyday living, the thoughtfully crafted interior features an expansive open floor plan with abundant natural light. The chef-inspired kitchen boasts double islands, premium cabinetry, Silestone countertops, a stylish glass tile backsplash, and a reverse osmosis system, with an adjacent walk-in pantry for added convenience. The family room is designed for comfort, complete with built-in surround sound and seamless indoor-outdoor connectivity through triple sliding doors leading to a covered lanai with retractable screens. A first-floor guest suite includes a private bath and custom Murphy bed, offering flexible space for visitors or a home office, with its own lanai access. Upstairs, the game room with office nook provides additional living space, while the primary suite is a true retreat, featuring French doors opening to a screened balcony with stunning lake views. The luxurious primary bath includes dual vanities, upgraded cabinetry, a walk-in shower, and a garden tub, creating a spa-like atmosphere. Three additional bedrooms, including one with an en-suite bath and two sharing a Jack-and-Jill bathroom, complete the second level, along with a fully equipped laundry room. Outside, the 40’ x 20’ saltwater pool and expansive deck create the perfect setting for entertaining or quiet relaxation. The fully fenced backyard offers both privacy and space to enjoy the beautiful lakefront setting. As part of the prestigious Hickory Hammock community, residents have access to resort-style amenities, including a clubhouse, fitness center, tennis and volleyball courts, a fishing pier, playground, dog park, picnic areas, and scenic walking trails—plus, golf carts are welcome. Conveniently located near Winter Garden Village, historic downtown Winter Garden, top-rated hospitals, and major highways, this home also offers easy access to Disney, Universal, fine dining, luxury shopping, and entertainment.

15986 Johns Lake Overlook Drive, Winter Garden

60 N Park Avenue, Winter Garden
$1,950,000
4 Beds ⋅ 5 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code
Experience Elevated Living in the Heart of Historic Downtown Winter Garden Welcome to 30 N Park Avenue—where luxury, location, and lifestyle converge in one of Central Florida’s most coveted addresses. Nestled in an exclusive enclave of just nine residences, this rarely available corner unit offers over 3,800 square feet of thoughtfully designed living space across four stunning levels. From the moment you arrive, you’re greeted by sophistication—professionally decorated interiors, curated high-end furnishings, and seamless indoor-outdoor flow. This fully furnished, turnkey home even includes a 6-person golf cart, inviting you to explore the charming boutiques, acclaimed restaurants, and award-winning West Orange Trail just steps from your door. Every detail was designed with both elegance and functionality in mind. A private elevator ensures effortless access to all levels, while soaring ceilings and rich finishes elevate every room. The chef’s kitchen features a gas range, premium appliances, and custom cabinetry—perfect for entertaining or quiet evenings at home. Retreat to your primary suite sanctuary with a spa-inspired bath including a soaking tub, dual vanities, and walk-in shower. A second ensuite bedroom on the ground floor offers privacy and convenience for guests or multigenerational living. Head up to the rooftop terrace and indulge in unforgettable sunsets from your private outdoor kitchen and hot tub, or unwind by the gas fireplace on the front terrace with views of the Trail. Additional features include: whole-house generator, spacious secondary bedrooms, and ample storage throughout. Located just steps from Winter Garden’s famed Farmers Market, historic museums, and vibrant community events, this is more than a home—it’s a lifestyle. Schedule your private tour today and discover the ultimate in luxury townhome living.

60 N Park Avenue, Winter Garden

17261 Heartwood Loop, Winter Garden
$1,910,500
5 Beds ⋅ 7 Baths ⋅ Avalon Estates SubDv. ⋅ 34787 Zip Code
Discover Winter Garden’s best-kept secret in Avalon Estates, a peaceful, horse-friendly enclave where timeless country charm meets modern luxury. This custom-built residence offers an impressive 6,400 sq. ft. under air and nearly 10,000 sq. ft. under roof, set on 4.6 picturesque acres surrounded by nature and serenity. From the moment you arrive, the inviting curb appeal and sprawling front porch set the tone for what awaits inside. Step through the double entry doors into a grand living space filled with soaring ceilings, abundant natural light, and an airy, open feel that defines Florida living at its finest. The modern farmhouse kitchen is a dream for entertaining, featuring two expansive islands, generous counter space, and seamless flow into the family room, where a wood-burning fireplace adds warmth and charm. French doors open to the pool area, complete with two oversized covered lanais, creating an ideal setting for relaxing or hosting guests. The downstairs primary suite is both spacious and inviting, featuring a private fireplace, large walk-in closet, and a magazine-worthy en suite bath. A private office sits just off the primary suite, offering a quiet retreat for work or study. Upstairs, you’ll find a large bonus room with kitchenette, three additional bedrooms, and two full bathrooms—perfect for family or guests. Don’t miss the panoramic views through the large windows—on clear nights, you can watch Disney fireworks sparkle in the distance and even catch NASA rocket launches from the east coast. Built with poured concrete tilt-wall construction, this home is as strong and resilient as it is beautiful. The laundry room doubles as a safe room, featuring metal doors, bullet-resistant glass, and reinforced concrete walls and ceiling. Additional highlights include a new roof (2025), an attached three-car garage, plus a detached 2.5-car garage with studio and full bath—ideal for guest quarters, an office, or hobby space. Located just minutes from shopping, dining, and major highways (Florida Turnpike, 429, and 408), this estate is 11 miles from Disney World, 12 miles from Universal Studios, and 23 miles from Orlando International Airport. With its combination of space, craftsmanship, and location, this property also offers excellent potential as a luxury short-term rental. Experience the tranquility and grandeur of Avalon Estates—schedule your private tour today and start creating lifelong memories in your new home.

17261 Heartwood Loop, Winter Garden

15058 Sunstar Way, Winter Garden
$1,900,000
5 Beds ⋅ 4 Baths ⋅ Highlands/Summerlake Grvs Ph 3 SubDv. ⋅ 34787 Zip Code
Experience LUXURY ~ WATERFRONT LIVING in this FULLY UPGRADED ~ POOL HOME in the sought-after Highlands at Summerlake Groves community of Horizon West! Built in 2021 and situated on a generous .40 ACRE LOT with a FENCED YARD, this exceptional home delivers breathtaking nightly views of DISNEY FIREWORKS reflecting across the water, creating a spectacular backdrop you can enjoy year-round from the comfort of your own home. Designed with both everyday living and unforgettable entertaining in mind, this home offers an OPEN CONCEPT layout filled with natural light, a dramatic two-story living room with a chic FIREPLACE feature wall, CUSTOM BUILT-INS, and WOOD LOOK TILE flooring throughout the main living areas. The spacious MAIN FLOOR PRIMARY SUITE delivers a private retreat, while a dedicated OFFICE with custom built-in cabinetry and desk space makes working from home effortless. Upstairs, you will find three additional bedrooms and one of the home's most impressive features – a PROFESSIONALLY DESIGNED THEATER ROOM with over $350,000 invested in premium finishes and technology, including a $12,000 projector, professional acoustic treatments, custom wall detailing, and seating for eight. No detail was overlooked when it comes to technology and convenience! Whole-home automation controls music, lighting, outdoor fans, LED lighting, water features, and more with the touch of a button. The WHOLE HOME & POOL SOUND SYSTEM further enhances the experience, while the two-car garage includes its own mini-split A/C system. Additional upgrades include a TILE ROOF, water softener, paver driveway, and separate 1-car and 2-car garages offering ample storage and flexibility. Step outside and discover a backyard designed to rival a private resort. The COVERED LANAI features a fully equipped OUTDOOR KITCHEN complete with a built-in grill, pizza oven, stone flat-top grill, vent hood, and oversized ISLAND for gathering. MOTORIZED SHADES provide privacy and comfort, while the CUSTOM POOL & SPA showcase three WATER FEATURES, dramatic FIRE ELEMENTS, and panoramic LAKE VIEWS. A perimeter mosquito misting system helps maintain a comfortable outdoor environment day and night, allowing you to fully enjoy Florida living year-round. Whether you are boating, skiing, entertaining guests, enjoying a movie night in the theater, or watching Disney fireworks dance across the lake each evening, this home offers a lifestyle few properties can match. Residents of the Highlands at Summerlake Groves also enjoy community amenities and a prime Winter Garden location just minutes from Orange County National Golf Center, the New Independence area, Disney parks, shopping, dining, Downtown Winter Garden, farmers markets, community events, and convenient access to SR 429. Waterfront luxury, state-of-the-art technology, unforgettable outdoor living, and one of the most impressive theater rooms you will find in a private residence – this is the opportunity you have been waiting for. Call today to schedule a private tour!

15058 Sunstar Way, Winter Garden

1020 Tildenville School Road, Winter Garden
$1,875,000
5 Beds ⋅ 5 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code
Step into luxury with this brand-new, custom-built J&J home! Featuring 5 spacious bedrooms, 4.5 baths, plus a loft and flex space, this home is designed for both comfort and style. GREEN certified home. The primary bedroom and two additional bedrooms are conveniently located on the main floor, offering easy living. Chef's kitchen with monogram appliances and a scullery kitchen complete with another refrigerator, sink, and tons of shelving. Enjoy quick access to the West Orange Fitness Trail and just 1.2 miles to historic downtown Winter Garden, with all its charming shops and dining options. Located in the Golf Cart District, this home is perfect for an active, convenient lifestyle. Relax in your private backyard oasis with a sparkling pool, spa, outdoor kitchen, and fully fenced-in yard. No HOA, and an oversized 3-car garage complete this exceptional property. Don’t miss your chance to own this one-of-a-kind home!

1020 Tildenville School Road, Winter Garden

16743 Broadwater Avenue, Winter Garden
$1,850,000
5 Beds ⋅ 6 Baths ⋅ Waterside On Johns Lake SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Get behind the gate of the highly sought-after Waterside community in Winter Garden. This extraordinary waterfront estate offers a rare blend of refined luxury, thoughtful design, and true lakefront living on Johns Lake. Built just six years ago and meticulously enhanced, this five-bedroom residence is primarily single-story, with the added flexibility of a private upstairs retreat featuring a spacious loft, full bedroom, and bathroom—ideal for guests, multi-generational living, or a quiet home office escape. From the moment you enter, the home makes a statement. Real, solid wood flooring flows throughout, adding warmth and authenticity that cannot be replicated with engineered alternatives. The expansive living areas were extended to create an open and inviting layout, perfectly suited for both everyday comfort and grand-scale entertaining. Dramatic waterfall-edge countertops anchor the kitchen and gathering spaces, blending modern elegance with timeless craftsmanship. The heart of the home extends seamlessly outdoors. An expansive, screened-in lanai overlooks the water, creating a true indoor-outdoor lifestyle. The electric, automatic screening system allows you to adjust the space effortlessly, making it enjoyable year-round. The outdoor kitchen is exceptional, designed for serious cooking and entertaining. It includes a Coyote gas grill, a Recteq pellet grill, a power burner, two outdoor refrigerators, a full-size sink, and a dedicated television—everything needed to host unforgettable evenings with friends and family. Beyond the lanai, the backyard opens to a large, fenced lawn that gently leads to your private dock on Johns Lake. The dock is fully equipped with a boat lift, as well as water and electricity, making lake access effortless and spontaneous. Whether you enjoy boating, fishing, or sunset cruises, this setting delivers the ultimate waterfront lifestyle. The saltwater infinity-edge pool is a showpiece, stretching an impressive 50 feet and designed to visually merge with the lake beyond. Heated by gas, the pool is ideal for both leisurely afternoons and evening swims, offering breathtaking views and a true resort-style experience in your own backyard. Inside, the home continues to impress with high-end features that elevate daily living. A tankless water heater ensures endless hot water, while a central vacuum system adds convenience and ease. The floor plan is both functional and elegant, offering five generously sized bedrooms and well-appointed bathrooms, all thoughtfully positioned to maximize privacy and flow. The property is further enhanced by lush landscaping and an abundance of fruit-bearing trees, including bananas, cherries, kumquats, and papayas, along with a beautifully maintained rose garden. These natural charms create a garden-like atmosphere that complements the lakefront setting. Located in gated Waterside, one of Winter Garden’s most desirable communities, this home offers privacy, exclusivity, and direct access to one of Central Florida’s most beautiful lakes, while remaining close to top-rated schools, dining, shopping, and major roadways. This is more than a house—it is a lifestyle defined by water, space, craftsmanship, and unforgettable outdoor living. Opportunities like this on Johns Lake are rare, and this residence stands apart in both design and execution.

16743 Broadwater Avenue, Winter Garden

15198 E Oakland Avenue, Winter Garden
$1,790,000
4 Beds ⋅ 4 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code
Welcome to this stunning farmhouse-style home nestled on a premium corner lot in one of the most sought-after communities near Historic Winter Garden. Thoughtfully designed and beautifully maintained, this home offers modern comfort with timeless charm. This is part of one of only 17 exclusive oversized luxury custom residences. Set in a thriving, close-knit neighborhood the area is known for its community charm and excellent schools. Take a short golf cart ride or bike the West Orange Trail to relax and unwind in the heart of downtown Winter Garden just minutes away. Inside, you'll be captivated by the gourmet kitchen, tall ceilings, and exposed wood beams that add warmth and character throughout. The bright, open layout is complemented by plantation shutter blinds, high-end finishes, and plenty of natural light. With a spacious 3-car garage, there's room for vehicles, storage, and more. Enjoy the added bonus of new A/C units in both the garage and attic—providing an additional 278 usable square footage for a home gym, workshop, or flex space. Step outside to your private backyard oasis, featuring a newly added **resort-style pool**, perfect for relaxing or entertaining all year long. Don’t miss your chance to own this rare and beautiful gem—schedule your private tour today!

15198 E Oakland Avenue, Winter Garden

958 Tildenville School Road, Winter Garden
$1,780,000
5 Beds ⋅ 5 Baths ⋅ N/A SubDv. ⋅ 34787 Zip Code
Exquisite New Construction in the Heart of Winter Garden’s Golf Cart District – Over 4,000 Sq Ft of Craftsman Charm! Step into timeless style and modern luxury with this brand new Craftsman-style masterpiece, perfectly situated on a charming cobblestone one-way street in the highly sought-after Golf Cart District of historic Winter Garden. Boasting over 4,000 square feet of beautifully appointed living space, this 5-bedroom, 4.5-bathroom estate offers the perfect blend of character, comfort, and convenience—all with NO HOA dues or restrictions. Set on over a third of an acre, the home impresses at first glance with custom landscaping, a massive covered front porch, and timeless curb appeal. Inside, enjoy warm wood flooring throughout, striking custom wooden beams in the foyer, and a spacious great room with electric fireplace—all flooded with natural light. Designed for entertaining, the open-concept layout includes a chef’s kitchen with custom cabinetry, gas appliances including professional grade gas range, built-in refrigerator and freezer stacks, walk-in pantry, wet bar with wine refrigerator, and a spacious island. Step outside to your private oasis complete with a large covered and pavered back patio, summer kitchen (grill + outdoor refrigerator), fenced yard, and a sparkling pool with heated spa—perfect for entertaining year-round. The downstairs primary suite offers a peaceful retreat with a spa-inspired bath, spacious shower, and massive walk-in closet finished with built-ins. A second downstairs bedroom with its own walk-in closet and nearby bath is perfect for guests or a home office. Upstairs, you'll find three additional bedrooms (each with walk-in closets), a loft living area, and even a second laundry/utility room for added convenience. The main laundry room downstairs is oversized, filled with natural light and extensive cabinetry, and an adorable mudroom just off the garage. Additional features include: Two-car garage PLUS a golf cart garage, dual tankless gas water heaters, gas appliances, and fully fenced back yard. This rare Winter Garden gem offers the best of both worlds—new construction luxury with the charm of Downtown Winter Garden living. Just moments from shops, dining, and everything downtown Winter Garden is known for. Don’t miss this opportunity to own a truly one-of-a-kind home in one of Central Florida’s most desirable communities.

958 Tildenville School Road, Winter Garden

148 Southern Railway Unit 8, Oakland
$1,770,000
34787 Zip Code
Under Construction. Building #08, the largest building, is available for purchase at Oakland Exchange, a premier commercial development in the Town of Oakland. Positioned at the front of the development, this building offers prime visibility from Southern Railway along with easy access. The building is being delivered in dark gray shell condition offering a fully customizable interior, giving buyers complete flexibility to design their ideal layout. The listed price is for a single entrance (option A) with an additional entrance façade (Option B and C) configuration upgrade available (ask for more details). Located off West Colonial Drive (State Road 50 – 56,500 AADT count) near the Florida Turnpike access ramp, it boasts excellent accessibility with high traffic and two entrances to the development. Situated between the rapidly expanding cities of Clermont and Winter Garden, this property offers a prime location for medical practices and businesses seeking to leverage the area's growth. Contact us for more information and to schedule a site tour of this outstanding commercial opportunity.

148 Southern Railway Unit 8, Oakland

902 Johns Point Drive, Winter Garden
$1,749,000
4 Beds ⋅ 4 Baths ⋅ Johns Cove 43/104 SubDv. ⋅ 34787 Zip Code
Seller financing available! Discover an extraordinary waterfront retreat where luxury, privacy, and breathtaking lake views come together in perfect harmony. This exceptional 4-bedroom, 4-bath custom residence offers over 4,000 square feet of thoughtfully designed living space on the shores of highly sought-after Johns Lake, delivering an unparalleled Florida lifestyle. Designed with both elegance and functionality in mind, the custom-built home features a desirable split-floor plan that provides ultimate privacy. The expansive primary suite occupies its own private wing, creating a true owner's retreat complete with serene lake views, generous sized closets, and a spa-inspired ensuite bath featuring a luxurious steam shower for the ultimate relaxation experience. The additional bedrooms are thoughtfully positioned on the opposite side of the home, offering comfort and privacy for family and guests. From the moment you enter, you'll be captivated by the abundance of natural light, soaring ceilings, and panoramic water views. Recent updates enhance both style and value, including fresh interior paint throughout and brand-new waterproof luxury laminate flooring with a lifetime warranty installed throughout the entire home. These elegant upgrades provide a seamless, modern aesthetic while offering exceptional durability for years to come. Designed for today's lifestyle, the home also features a spacious executive office, ideal for remote work or a private study, along with a highly desirable game room that offers endless possibilities for recreation, media, or entertaining. The heart of the home is a spacious chef's kitchen that opens effortlessly to the main living spaces, allowing you to enjoy lake views while cooking, dining, or entertaining. Expansive windows and glass doors flood the home with natural light while framing the stunning waterfront scenery and creating a seamless connection between indoor and outdoor living. Step outside to your private resort-style oasis featuring a sparkling pool, spa, covered lanai, and private boat dock. Enjoy direct access to Johns Lake, one of Central Florida's premier recreational lakes, offering endless opportunities for boating, fishing, jet skiing, paddleboarding, wakeboarding, and unforgettable sunset cruises right from your backyard. Whether relaxing poolside, entertaining guests, or enjoying a quiet evening overlooking the water, every day feels like a vacation. What's more you have easy access to Florida's turnpike and 429 for seamless access to downtown Orlando, area theme parks, and Orlando International Airport!! Schedule for showing today.

902 Johns Point Drive, Winter Garden

1216 Hull Island Drive, Oakland
$1,730,000
5 Beds ⋅ 5 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code
Experience the ultimate lakefront lifestyle in this stunning MI Homes Endeavor, perfectly positioned on 83 feet of shoreline along Lake Apopka - No Flood Zone - in the highly desirable community of Hull Island. Built just 5 years ago, this exceptional residence offers 4,224 square feet of thoughtfully designed living space featuring 5 bedrooms, 4.5 bathrooms, bonus room, two dedicated office spaces (one on each floor), and a 3-car garage. Every detail of this home has been carefully curated with extensive post-builder upgrades and thoughtful custom touches throughout. With no rear or front neighbors, this property delivers both privacy and breathtaking natural beauty. Enjoy unforgettable sunset views from the newly installed Trex boat dock, the resort-style screened pool and patio, or nearly every west-facing room in the home. Out front, peaceful preserve views create the perfect backdrop for sunrise mornings. From the moment you step inside, you’re welcomed by soaring ceilings, abundant natural light, and stunning water views. The dramatic family room showcases impressive vaulted ceilings, creating an open yet inviting atmosphere ideal for both entertaining and everyday living. The gourmet kitchen is truly a chef’s delight, featuring a massive center island, natural gas cooktop, built-in convection oven, stainless steel appliances, and extensive cabinetry and prep space. The adjoining dinette area offers casual dining convenience, while the formal dining room provides an elegant setting for gatherings and celebrations. The first floor also includes a wine room, private office, guest bedroom, and full pool bath with direct outdoor access. Designed for exceptional indoor-outdoor living, the backyard retreat is nothing short of spectacular. The recently designed luxury pool features elegant waterfall and fountain elements, an oversized jacuzzi, custom natural gas fire pit, turf play area, and expansive covered lanai complete with tongue-and-groove ceiling and travertine flooring — all enclosed within a panoramic screen offering unobstructed lake views. Enjoy direct access to Florida’s natural beauty right from your backyard. Spend your evenings fishing from the private dock, launching your boat with ease from the electric lift for a sunset cruise on Lake Apopka, or exploring the connected Tavares Chain of Lakes and charming downtown Mount Dora by water. Upstairs, a striking staircase with sleek glass railings enhances the home’s modern design. The luxurious owner’s suite offers incredible lake views and a recently renovated spa-inspired ensuite featuring a freestanding soaking tub, oversized walk-in shower, and designer finishes. The spacious game/media room and second office overlooking the preserve offer incredible flexibility for work, entertainment, or multigenerational living. Secondary bedrooms enjoy beautiful views, while the fourth bedroom functions perfectly as a private mini-suite. Ideally located in the charming Town of Oakland, Hull Island offers convenient access to Winter Garden, Clermont, the Florida Turnpike, shopping, dining, and recreation. Community amenities include a pool, playground, dog park, and private dock access on the nature preserve - all with a low HOA. This is a rare opportunity to own an extraordinary lakefront retreat where luxury, comfort, and the Florida lifestyle come together seamlessly. Schedule your private showing today and experience lakeside living at its finest.

1216 Hull Island Drive, Oakland

68 N Park Avenue, Winter Garden
$1,725,000
4 Beds ⋅ 5 Baths ⋅ 30 North Park SubDv. ⋅ 34787 Zip Code
Experience the ultimate in luxury urban living at 68 N Park Ave, a stunning 3-story townhome with rooftop deck located in the heart of Historic Downtown Winter Garden. This sophisticated 4-bedroom, 4.5-bathroom residence offers over 3,500 sq. ft. of meticulously designed space, seamlessly blending modern elegance with the charm of the historic district. The open-concept main level features soaring 11-foot ceilings, expansive industrial-style windows, and a chef’s dream kitchen equipped with an oversized quartz island, natural gas appliances, and custom artisan cabinetry. Accessibility is effortless with your own private elevator serving all floors. Retreat to the third-floor master suite, featuring a spa-inspired bath and massive walk-in closet, or host guests in the versatile first-floor bedroom suite. The "wow factor" continues on the 1,200 sq. ft. private rooftop terrace, offering panoramic views of the city skyline—the perfect spot for evening cocktails or watching local fireworks.Location is everything. Leave your car in the 2-car garage and embrace the golf-cart-friendly lifestyle. You are just steps away from: The award-winning Winter Garden Farmers Market, The vibrant Plant Street Market and Crooked Can Brewing Co, The world-class West Orange Trail for biking and running, Boutique shopping, fine dining, and the historic Garden Theatre. Don’t miss this rare opportunity to own a piece of downtown luxury. Schedule your private showing today!

68 N Park Avenue, Winter Garden

15210 E Oakland Avenue, Winter Garden
$1,725,000
5 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code
Discover the pinnacle of custom-built luxury in Winter Garden with this spectacular 5-bedroom, 3-bathroom Modern Farmhouse, crafted by the esteemed Justice & Wood Builders. This home is situated within Oakland Hills, a truly exclusive enclave of just 17 homesites, offering a private and peaceful lifestyle while remaining mere moments from the energy of Historic Downtown Winter Garden. Set on a rare and expansive 0.47-acre lot, the property is graced by the majestic, moss-draped canopy of towering old oak trees, creating an idyllic, tranquil setting from the moment you arrive. Step inside to an airy, open-concept living space where natural light floods the wide-plank wood floors. The heart of the home is defined by dramatic cathedral ceilings, beautifully accentuated by rich, exposed timber ceiling beams. The kitchen is a masterful fusion of high design and functionality—a space that moves beyond standard "gourmet." It features premium shaker cabinetry, a massive center island finished in a striking blue-gray hue for contrast, and luxurious quartz countertops. Chefs will appreciate the professional stainless steel appliances, the deep farmhouse sink, and the dedicated natural gas range for precision cooking. The home's thoughtfully designed layout provides versatile living areas for every need. The three-car garage offers not just ample storage and parking, but the convenience of an EV adapter in the third bay, ready for your electric vehicle. Escape to the generous private bedrooms, the upstairs bedroom offers a flexible space that can easily serve as a dedicated home office, home gym, media room, or guest suite. This room comes with the significant advantage of both air-conditioned storage and a large walk-in attic, ensuring clutter-free living. Bathrooms feature clean lines, modern fixtures, and striking custom tilework. The dedicated laundry room is equally impressive, boasting extensive cabinetry, quartz counters, and an eye-catching patterned tile backsplash. The fully fenced backyard provides exceptional privacy for your personal resort. The stunning private pool and spa are surrounded by a spacious paver patio, complemented by a charming fire pit area, making this the ultimate space for both lavish entertaining and quiet relaxation. Crucially, this exceptional home is zoned for highly-rated schools offering excellent educational opportunities. The coveted location ensures you are only minutes from the vibrant, golf-cart-friendly atmosphere of Historic Downtown Winter Garden, with its acclaimed Farmers Market, Plant Street Market, unique boutiques, and fine dining. This is a rare opportunity to own a meticulously crafted, custom home in one of Winter Garden's most desirable and private communities--priced BELOW APPRAISED VALUE. Schedule your private showing today to experience this unparalleled lifestyle in Oakland Hills!

15210 E Oakland Avenue, Winter Garden

121 W Maple Street, Winter Garden
$1,700,000
4 Beds ⋅ 4 Baths ⋅ G T Smith Sub 2 SubDv. ⋅ 34787 Zip Code
**MULTIPLE OFFERS RECEIVED** Welcome to 121 West Maple Street…a Downtown Winter Garden one-of-a-kind statement home spanning nearly 5,500 square feet of indoor & outdoor living space. Originally constructed in 1999 and thoughtfully expanded in 2019…yet this special residence has the heart & soul of a time long ago when character, craftsmanship and attention to details mattered. Private Pool & Spa. Poolhouse. Drawing Room & Study. Courtyard with Fountain. Renovated Kitchen & Bathrooms. 10’ Ceilings. Wood Floors. Handmade (USA) Solid Wood Doors. Custom Wood Trim Throughout. Three-Car Garage with Carriage House. Three Fireplaces. Natural Gas. Custom Built Wood Fence with Copper Caps. Located on one of the few remaining brick roads just TWO BLOCKS from Plant Street, this home with spectacular curb appeal is situated on a rare corner double lot with extensive landscaping & beautiful mature trees…including the incredible Southern Live Oak in front that is part of the Winter Garden Heritage Trees project & walking tour. Enjoy historical charm appropriate for the location...yet live without the pains & aches of owning an old historic home. The incredible drawing room & study (2019) was designed by the historical architect for the City of Charleston…twenty-nine windows, extensive trim work & built-ins, historically accurate sconces & lighting and automatic privacy shades. Live the Florida lifestyle outdoors in this incredible outdoor oasis with heated pebble tec saltwater pool & spa. Following a 2023 transformation with a cost of $225,000, the outdoor living space now features a custom poolhouse cabana with a gas fireplace, multiple seating areas, outdoor kitchen with island, built-in grill, burner and refrigerator, retractable screen to astroturf lawn, Trex decking, custom lighting, water features, extended covered lanai and SunBrite outdoor television. (Hayward Natural Gas Pool/Spa Heater - 2025; Hayward Tristar Pool Pump - 2023; Filter Unit - 2020; Salt Cell - 2020). Fantastic & FLEXIBLE floor plan...four bedrooms, three full bathrooms and one half bathroom. Primary suite on main floor. The carriage house above the garage features a separate staircase entrance with private bedroom, bathroom and walk-in closet with built-ins. Stunning kitchen renovation (2021) including custom cabinetry, backsplash, quartz countertops, farm sink, designer lighting, new appliances and an open-concept design that flows effortlessly into the family room. Roof -- July 2019. HVAC -- 2025 (upstairs); 2018 (downstairs - damper system). Tankless Gas Water Heater -- Dec 2015. Garage Epoxy Floor. Whole Home Natural Gas Generator. FULL UPGRADE & SPECIAL FEATURES LIST AVAILABLE. Furnishings and decor (inside & outside), golf cart & custom holiday decorations NEGOTIABLE. Zoned R-2. NO HOA...live without rules & restrictions. You COULD NOT be closer to enjoying the lifestyle of Central Florida's most desirable and growing historic downtown...GOLF CART LIFE, the West Orange Trail, HUGE weekly farmer's market, incredible annual festivals, shopping, dining, art gallery, the Crooked Can Brewery & Plant Street Market, parks & recreation...come JOIN THE FUN! Also conveniently located minutes from the Winter Garden Village shopping center and just minutes from HWY 429 with direct connect to the Turnpike and 408 for an easy commute to anywhere in Central Florida. This is THE ONE you have been waiting for in Downtown Winter Garden.

121 W Maple Street, Winter Garden

9072 Bradleigh Drive, Winter Garden
$1,700,000
5 Beds ⋅ 5 Baths ⋅ Latham Park South SubDv. ⋅ 34787 Zip Code
Experience the very best in true lakefront living where every detail has been carefully designed for comfort, style, and enjoyment. Located in the heart of Winter Garden within the highly desirable Latham Park community, this extraordinary residence combines modern luxury with the serenity of waterfront living. Perfectly positioned less than two miles from Walt Disney World and a short stroll to new shops and restaurants, the home captures the essence of convenience and exclusivity. Set on a beautifully landscaped 1.25-acre lot, this five-bedroom, four-and-a-half-bath home with a three-car garage offers sweeping lake views and private access to Lake Lartigue, a tranquil 42-acre freshwater lake ideal for fishing, peace and serenity. The property’s private dock and outdoor living spaces make it perfect place to entertain and live the Florida lifestyle to the fullest extent. Inside, refined design and craftsmanship are evident throughout. The first floor showcases an open-concept layout centered around a stunning gourmet kitchen featuring stacked cabinetry, quartz countertops, and a waterfall island that seamlessly connects to the spacious family room. Fully vented NATYURAL GAS cooktop and the pot filler faucet is always a postive.The formal dining room provides a sophisticated setting for entertaining, while large windows and glass doors fill the home with natural light and offer beautiful views of the pool and lake beyond. The primary suite is a private retreat with direct access to the covered lanai and the heated saltwater pool and spa. Its spa-inspired bath features a floor-to-ceiling glass shower enclosure, modern finishes, and a serene ambiance that creates the perfect place to unwind. A second bedroom on the main level provides flexibility for guests or an office. Upstairs, three additional bedrooms offer generous space, including a Jack-and-Jill bath that connects two of the rooms. The expansive game room opens to a screened-in balcony, where you can take in breathtaking panoramic views of the lake. Elegant wood flooring flows through the main living areas, complemented by tile in all wet spaces and 8-foot doors throughout. The home also includes a premium Sonos surround sound system for an elevated audio experience. With 3,750 square feet of living space, this Grafton floor plan delivers both sophistication and functionality. Residents of Latham Park enjoy access to a community clubhouse, resort-style pool, and scenic nature trails perfect for leisurely walks. The location is unbeatable—just minutes from major highways, world-class dining, the Hamlin retail district, and top-rated schools including Foundation Academy and Windermere Preparatory. Tile roof, security system with google cameras, Culligan water filtration system, storage racks in the finished garages and seamless screen enclosure for perfect views are all worth stating. From the moment you step through the door, you’ll know you’ve found something truly special—an impeccably maintained lakefront haven where luxury meets lifestyle in one of Central Florida’s most sought-after communities.

9072 Bradleigh Drive, Winter Garden

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