Homes for Sale Near West Orange High in Winter Garden - 169 homes

Remarks: Virtually Staged. Lender Credit of 1% (of loan amount) toward closing costs or rate buy-down (inquire for more info). Welcome to CARRIAGE POINT, a GATED Winter Garden community offering an exceptional location and a thoughtfully designed floor plan. This two-story POOL home delivers the space today’s buyers crave, room for everyone, from dedicated home offices to flexible living and guest areas. With 3,435 square feet of living space, this home features five bedrooms, four full bathrooms, and a large bonus room. As you enter the home, you are welcomed by a spacious living room and dining room before continuing into the heart of the home. The open-concept kitchen features granite countertops, 42-inch cabinetry with crown molding, under-cabinet lighting, a gas range, an expanded pantry, and plenty of space for a breakfast table. The kitchen opens to the family room with sliding doors leading out to the SCREENED-IN POOL and FENCED backyard. The first floor features a desirable three-way split floor plan with four bedrooms and three full bathrooms. The spacious downstairs primary suite offers plenty of room to relax, along with a walk-in closet and private en-suite bathroom. Upstairs provides even more flexibility with a fifth bedroom, fourth full bathroom, and a large living area. Newer luxury vinyl plank flooring extends throughout the upstairs and staircase. The outdoor living space is a true highlight of this home with an expansive screened-in SALT WATER POOL ADDED IN 2021. Designed with both relaxation and fitness in mind, the pool features water jets giving a swim-against-the-current feature, creating the perfect space to enjoy a refreshing swim or get in a low-impact workout. Carriage Pointe offers residents a variety of community amenities including a tennis court, playground, soccer field, and walking path. For those who enjoy an active lifestyle, the area offers miles of scenic trails, including the West Orange Trail, along with parks and outdoor activities nearby. The location is ideal, with convenient access to State Road 429 and Highway 50, making travel throughout Central Florida easy. Enjoy being close to Winter Garden Village, the Hamlin area, restaurants, shopping, entertainment, and AdventHealth Winter Garden. Families will appreciate the HIGHLY RATED SCHOOLS, including Whispering Oak Elementary, Hamlin Middle School, and West Orange High School. Historic Downtown Winter Garden is less than five miles away and offers charming shops, local restaurants, the weekly farmers market, the West Orange Trail, and year-round community events. Additional features include a three-car garage, natural gas service through Lake Apopka Natural Gas District, gas washer and dryer, a 2020 water heater, updated electrical service, and added electrical for a built-in microwave. With its exceptional floor plan, private pool, flexible living spaces, and prime Winter Garden location, this Carriage Pointe home offers exceptional space, comfort, and convenience. Schedule your private tour today!

Listing is courtesy of: EXP REALTY LLC (407-305-4300)

Listing Agent: Justin Core (407-305-4300)

Remarks: *Walkthrough Video Available* Welcome to the gated Emerald Ridge neighborhood that is conveniently located near the 429, Turnpike, shopping and restaurants in Winter Garden, Horizon West and Windermere as well as the charming downtown Winter Garden Plant Street and all of the local activities it brings. Cool off in the COMMUNITY POOL and enjoy staying active on the sidewalks that run throughout the neighborhood. This home has an OPEN FLOOR PLAN that greets you as soon as you enter. The spacious living room has nice natural lighting and opens to the eat-in kitchen which was recently remodeled. You’ll find NEW CABINETRY with soft-close doors, a TILE BACKSPLASH and STAINLESS STEEL appliances. The WALK-IN PANTRY is a dream as it gives storage space for kitchen wares and laundry needs. Sliding doors open to the SCREENED PATIO so you can enjoy the evening breeze. There’s a SPACIOUS LOFT upstairs which makes for a fantastic 2nd living room, home office, play space, or home gym. The primary suite in this model is extra large giving room for a sitting area! The WALK-IN CLOSET offers plenty of space to keep your wardrobe organized and the en-suite bathroom has a garden tub and separate shower. The secondary bedrooms share a hall bathroom. The ROOF, AC, AND WATER HEATER WERE REPLACED IN 2018. Additional upgrades include CROWN MOLDING and canned lighting throughout the home.

Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)

Listing Agent: Tennille Biggers (850-628-4455)

Remarks: 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.

Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)

Listing Agent: Kevin Sullivan (321-663-3457)

Remarks: A home that's finally been paid attention to. Four bedrooms, two-and-a-half baths, 2,891 square feet. A full 2022 refresh. New roof, new water heater, new softener, new stainless appliances, EV charger in the garage. Inside, warm wood flooring runs uninterrupted through the main floor, from the foyer and dedicated office space into the kitchen and living area that anchors the back of the home. Fresh white cabinets, durable granite counters, stainless appliances, custom tile backsplash. A kitchen you'll love to use and to look at. The bay window pulls in the morning light over the breakfast nook, and the living space is big enough for the family gatherings you'll actually host. Then the rarity, a massive fully screened lanai on brick pavers that stretches the width of the home with ample space to entertain a party of two or twenty, along with a long serving counter ready for a grill setup, drinks station, or whatever the party calls for. Past the screen, the yard is vinyl and stone fenced, artificial turf underfoot so you're not wasting Saturdays mowing. Upstairs, the primary suite carries real volume with a tray ceiling, plus a separate flex space that reads as a sitting area, office, or nursery, really whatever you need it to be. Two walk-in closets built out with custom shelving, and a bath with dual vanities, garden tub, and separate shower. The other three bedrooms are generously sized, all fitted with custom built-ins in the closets. You'd be pleased to know the beauty extends beyond the home itself and into where it sits. You're two minutes from Winter Garden Village. Target runs, AdventHealth, restaurants, shopping for the retail-therapy days, all of it. Ten minutes north drops you onto Plant Street: Crooked Can, the Saturday farmers market, the West Orange Trail running twenty-two miles through the middle of it. Disney sits twenty minutes away so close enough for a Tuesday afternoon, far enough that the tourism doesn't reach here. Not to mention the pool, tennis courts, playground, and clubhouse are all a short walk from the front door, so you don't have to leave the neighborhood to have a good time. If a picture is worth a thousand words, walking through is worth a lifetime. Come see it in person!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Romario Gabbidon (352-460-6519)

Remarks: Under contract-accepting backup offers. Experience lakefront living at its finest in this completely reimagined residence in the highly sought-after Westfield Lakes community, where breathtaking panoramic views of Lake Beulah create a stunning backdrop for everyday living. This exceptional home offers an unparalleled lifestyle both inside and out. From the moment you enter, sweeping water views draw your attention through the home's bright, open living spaces. The spacious family room serves as the heart of the home, featuring a beautiful fireplace and uninterrupted views of the water, creating a warm yet sophisticated setting for both entertaining and everyday living. The designer kitchen has been thoughtfully crafted for those who appreciate both style and functionality. Anchored by a large center island, the space showcases stone countertops, LED underlighting, and top of the line stainless steel appliances. A charming breakfast nook overlooks the lake, while the formal dining room provides the perfect setting for hosting larger gatherings. Privately positioned to maximize the home's stunning waterfront setting, the primary suite is a true retreat. Wake up to tranquil lake views and enjoy direct access to the outdoor living areas through private doors leading to the pool deck. The spa-inspired primary bath has been beautifully remodeled and features dual vanities, designer finishes, an oversized walk-in shower, and a spacious custom walk-in closet. The home's thoughtful floor plan continues with two additional on-suite bedrooms, and home office. Upstairs, a large bonus room / fourth bedroom offers endless flexibility and can serve as a media room, game room, fitness studio, or additional gathering space. Step outside and discover a private waterfront paradise designed for year-round enjoyment. The expansive marble pool deck surrounds a resort-style pool and spa, while the oversized covered lanai creates the ultimate outdoor entertaining venue. Complete with a fully equipped summer kitchen, this spectacular space allows you to dine, relax, and entertain while taking in the breathtaking sunsets and unobstructed views across Lake Beulah. Residents of Westfield Lakes enjoy access to an exceptional collection of community amenities, including tennis/pickleball court, 2 playgrounds, 2 docks, and scenic walking trails. Perfectly positioned just minutes from Winter Garden Village, the 22 mile West Orange Trail, top-rated schools, and an abundance of shopping, dining, and entertainment options, this remarkable lakefront residence offers the rare opportunity to enjoy luxury waterfront living in one of Winter Garden's most desirable communities.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Christopher Christensen (407-312-8003)

Remarks: Under contract-accepting backup offers. Seller Offering Up to $7,000 Toward Buyer Closing Costs and a one YEAR AHS Home Warranty. Use our Preferred Lender and they will contribute $1000 towards closing costs with loan approval at closing! $8000 total value to BUYER at closing!! Move-in ready and priced under $298,000, this beautifully updated condominium in the gated Southern Pines community offers exceptional value just minutes everything needed for a balanced lifestyle. Located only 7 minutes from Historic Downtown Winter Garden, this second-floor residence combines modern upgrades, generous storage, and resort-style amenities in one of the area's most convenient locations. The open-concept floor plan features spacious living and dining areas accented by engineered hardwood flooring that extends throughout the main living spaces and into a dedicated office alcove with custom built-in shelving. Fresh interior paint, updated lighting fixtures, ceiling fans and plenty of windows create a bright, contemporary feel throughout. The primary suite offers brand-new carpet, a generous walk-in closet, and a private bath featuring a large walk-in shower, granite-topped vanity, and updated lighting. Two additional bedrooms also feature new carpeting, updated fans and lighting fixtures, and oversized walk-in closets. A well-appointed secondary bath includes an extended granite vanity with abundant storage and a versatile tub/shower combination. At the center of the home, the upgraded kitchen showcases white cabinetry, granite countertops, a new stainless-steel sink with drying rack and pull-down faucet, plus a complete suite of brand-new appliances including refrigerator, range, microwave, and dishwasher. A dedicated laundry area with storage shelving and a separate adjacent linen closet provide added convenience, while multiple walk-in closets in the bedrooms have an uncommon amount of storage for condominium living. Major systems have already been addressed for peace of mind. The HVAC system has recently had seasonal servicing. The hot water heater is awaiting permitting and will be replaced in June 2026, and the home is protected by a transferable home warranty plan. (Covers Appliances, Ceiling Fans, HVAC, HWH, disposal, plumbing and more) Southern Pines residents enjoy an impressive amenity package including gated entry, on-site management, resort-style pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and even a resident car wash station. Conveniently located just minutes from Publix, Winter Garden Village, the West Orange Trail, Downtown Winter Garden, major shopping, dining, and entertainment, with quick access to the Turnpike, SR 429, I-4, Orlando attractions, and area employers. HOA dues include internet, basic cable, recreational amenities, trash service, and exterior lawn and maintenance. No worries here about Roof Replacement or Exterior Maintenance cost, true worry free living. This is the complete condominium lifestyle package—updated with NEW NEW NEW is really move-in ready in an amenity-rich, and ideally located community. Come see it today, we would love to show it to you.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Mildred Hershiser (407-758-5263)

Remarks: Under contract-accepting backup offers. Welcome to 13822 Jomatt Loop! This stunning home offers 4 spacious bedrooms, 3 full bathrooms, a bonus loft space, private office and a 3 car garage off of an expansive driveway, all perfectly situated on an OVERSIZED FULLY FENCED LOT. Designed for both comfort and entertaining, the open-concept floor plan features generous living and dining spaces filled with natural light, and was just freshly painted throughout. The primary bedroom is located on the first floor and features his and hers walk in closets with CUSTOM BUILT INS, dual vanity spaces, a free-standing soaker tub, and spa like shower. Located on the second level is a large bonus room that's perfect for kids to play, a movie room, game room, and so much more. Step back outside to your personal backyard oasis where you can enjoy year-round Florida living with a heated sparkling pool and spa that's peacefully nestled between lush landscaping and a fully fenced yard. The expansive covered lanai is enhanced by a stunning outdoor kitchen by Paradise Grills, ideal for hosting gatherings, weekend barbecues, or simply unwinding at sunset. Additional upgrades include GAS APPLIANCES, custom living room built in entertainment center, automated pool pump, and various other thoughtful finishes throughout that elevate both style and function. This home is zoned for A-rated schools including Sunridge Elementary School and Sunridge Middle School, making it an exceptional choice for families seeking top-tier education options. Schedule your showing today! With its rare oversized conservation lot, luxury outdoor living, and prime location, this home truly checks every box. Schedule your private showing today and experience the lifestyle you’ve been waiting for.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Jenna Palmero (407-697-8727)

Remarks: COMPLETELY REMODELED WATERFRONT HOUSE WITH COVERED PRIVATE DOCK AND BOAT LIFT ON THE LARGEST LAKE IN CENTRAL FLORIDA!!! A highly energy-efficient house with owned solar panels ($30 monthly grid surcharge vs. $500-600 electric bill before). The cost of solar panels is included in the purchase price. The price can be reduced by $37K if the buyer assumes a solar panel loan at 3.49%. Experience the ultimate LAKEFRONT living with this stunning, COMPLETELY REMODELED HOUSE ($400K investment) on Lake Apopka in Winter Garden, in the heart of a highly desirable GOLF CART DISTRICT. Boasting over 3,700 sq. ft. of beautifully remodeled living space, this 4-bedroom, 3.5-bathroom residence combines modern luxury with waterfront charm. Every inch of this home has been meticulously upgraded, creating a move-in-ready oasis with high ceilings, open-concept living, designer lighting and upgraded finishes throughout. Gorgeous porcelain tile and hardwood floors flow seamlessly across two stories, complemented by abundant natural light from all-new, PANORAMIC WINDOWS. The gourmet kitchen is a chef’s dream, featuring quartz countertops, a large island with built-in cabinetry, stainless steel appliances, a backlit quartz bar, a wine fridge and a modern backsplash. Entertain effortlessly in the expansive high-ceiling dining room and living room, framing incredible LAKE APOPKA VIEWS, GORGEOUS SUNRISES AND BREATHTAKING SUNSETS! The spacious master suite on the ground floor is a serene retreat with a high ceiling, two walk-in closets, an oversized bathroom with two sinks, Jacuzzi and a massage shower and a private screened patio. Two additional bedrooms on the ground floor boast lake views, California closets and high ceilings. A second-floor oversized loft offers a full bathroom, a walk-in closet, separate HVAC and noise-reducing flooring and window treatment —perfect for another master bedroom or entertainment room. Two Florida rooms on both floors provide stunning panoramic lake views. A dedicated office/den on the ground floor is ideal for work or study. All bathrooms have windows and exhaust. Enjoy 90 feet of open-view waterfront—perfect for skiing, boating, fishing, or relaxing. The oversized COVERED BOAT DOCK has electric BOAT LIFT, lighting, WATER, and a Margaritaville-themed bar. The backyard features a RECENTLY RESURFACED SALTWATER POOL with a NEW PUMP, NEW POOL FILTER, a REFENCED PRIVATE YARD, fruit trees & mature, landscaped greenery. Additional highlights include NEW WINDOWS, HVAC, SOLAR PANELS, SMART THERMOSTAT, upgraded irrigation and landscaping, a TWO-CAR GARAGE with a lot of built-in storage and an OVERSIZED DRIVEWAY to park multiple boats or vehicles. Located in a quiet, family-friendly GATED COMMUNITY with golf-cart-friendly streets and DIRECT ACCESS to the scenic WEST ORANGE TRAIL and high-rated elementary and middle SCHOOLS NEARBY. Enjoy Winter Garden’s historic downtown just minutes away, with A-rated schools, shopping, dining, and the farmer's market. Only 20 minutes to Downtown Orlando and close to Disney, Universal, and major highways. There are 6 highly rated Golf Clubs within a 5-mile radius. This is more than a home—it’s a boater’s and fisherman’s paradise, a lakefront retreat, and a perfect family haven all in one. Don’t miss this rare opportunity to own a completely remodeled luxury waterfront home with unmatched views and lifestyle amenities on Lake Apopka, offering over 30,000 acres of endless water fun!

Listing is courtesy of: KELLER WILLIAMS EAGLE REALTY (305-757-1700)

Listing Agent: Marina Kostic (240-421-6466)

Remarks: Under contract-accepting backup offers. Experience refined luxury in this stunning Parade of Homes Award-Winning Delray Model, now professionally designed and extensively renovated with today's most sought-after finishes and truly move-in ready. From the moment you arrive, you'll appreciate the home's impressive Italian-inspired architecture, soaring two-story foyer, elegant balconies, and exceptional craftsmanship. The first floor has been transformed with beautiful wood-look porcelain tile throughout, creating a seamless and sophisticated living space. Fresh interior and exterior paint, professionally redesigned landscaping, and a newly finished outdoor terrace accented with white stone provide outstanding curb appeal and exceptional outdoor living. At the heart of the home is a spectacular chef's kitchen featuring an oversized natural stone island, designer backsplash, 42-inch cabinetry with illuminated upper display cabinets, soft-close drawers and doors, crown molding, under- and over-cabinet lighting, premium KitchenAid appliances, a gas cooktop with pot filler, walk-in pantry, and abundant storage. Entertain with ease while enjoying the custom wine cellar tucked beneath the staircase with wrought-iron gate and wine refrigeration. The luxurious first-floor primary suite has been completely remodeled into a spa-inspired retreat, showcasing a beautifully redesigned bathroom with premium finishes, an oversized walk-in shower, freestanding soaking tub, and spacious walk-in closet. A primary owner suite with its own en-suite bath is also conveniently located on the main level. Upstairs, an expansive gathering room with rich wood flooring, tray ceiling, and built-in workspace opens to an impressive 22-foot balcony. The dedicated theater room features a wet bar and beverage cooler, while three additional en-suite bedrooms—including a second primary suite—offer comfort and privacy for family and guests. The covered lanai seamlessly extends the indoor living space through dramatic three-panel stacking glass doors and is pre-plumbed for a future summer kitchen. The beautifully designed backyard with lash landscaping and privacy bamboo trees are complementing a stylish white stone terrace offering the perfect blend of comfort and sophistication, creating an inviting outdoor retreat for relaxing and entertaining or your own private sanctuary. Located within the exclusive gated community of Canopy Oaks in Winter Garden, this exceptional residence combines timeless architecture with extensive modern upgrades rarely found in today's market. Every detail has been thoughtfully updated, making this a truly one-of-a-kind luxury home ready for its next owner.

Listing is courtesy of: MY HOME INTERNATIONAL REALTY LLC (813-735-0319)

Listing Agent: Zana Dobrilovic (813-735-0319)

Remarks: Short Sale. Don't miss this beautifully updated 2-bedroom, 2-bathroom townhouse offering the perfect blend of comfort, convenience, and unbeatable location. Tucked away in a quiet community, this home is just minutes from all the charm and excitement of downtown Winter Garden, known for its boutique shopping, top-rated restaurants, farmers market, splash pad, and the scenic West Orange Trail. Inside, you'll find a thoughtfully updated interior offering easy, low-maintenance living. Perfect for first-time buyers, downsizers, or investors looking for a move-in ready property in one of Central Florida's most sought-after towns. With its prime location close to shopping, dining, parks, and major roadways, this townhouse offers an unbeatable opportunity to enjoy the best of downtown Winter Garden living without the downtown price tag. Schedule your showing today!

Listing is courtesy of: REAL BROKER, LLC (407-922-8986)

Listing Agent: Denise Pellegrino (352-978-9720)

Remarks: Welcome to this beautifully designed 2022-built home freshly painted, move in ready and located in the highly sought-after Waterside at Johns Lake community in Winter Garden! Offering 4 bedrooms, 3 full bathrooms, and over 2,030 square feet of thoughtfully designed living space, this move-in ready home combines modern style, functionality, and an unbeatable location. Step inside to an open-concept floorplan featuring a spacious great room, abundant natural light, ceramic tile flooring in the main living areas, and seamless flow between the kitchen, dining, and living spaces — ideal for entertaining and everyday living. The kitchen features solid surface countertops, modern appliances, ample cabinetry, and overlooks the main gathering areas for easy living and hosting. The flexible layout includes a desirable first-floor bedroom and full bath perfect for guests, multigenerational living, or a private home office. Upstairs, the spacious primary suite offers a walk-in closet and relaxing retreat feel, while additional bedrooms provide generous space and versatility. Additional features include central air, public utilities, inside laundry, ceiling fans, walk-in closets, split-bedroom design, and modern finishes throughout. Located in Waterside on Johns Lake, residents enjoy resort-style community amenities including a community pool, playground, walking trails, green spaces, and scenic surroundings. Conveniently located near Downtown Winter Garden, Horizon West, Hamlin, Winter Garden Village, SR-429, Florida Turnpike, Disney, shopping, dining, hospitals, golf, and top-rated schools. Enjoy easy access to everything Central Florida has to offer while living in one of Winter Garden’s fastest-growing and most desirable communities.

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Cassie Lamoureux (407-432-9180)

Remarks: Welcome to this beautifully updated 4-bedroom, 2.5-bath pool home nestled within the highly sought-after gated community of Lake Amberleigh in the heart of Winter Garden. Offering 2,762 square feet of thoughtfully designed living space, this meticulously maintained residence combines timeless elegance with modern updates, making it the perfect place to call home. From the moment you arrive, you'll be captivated by the home's charming curb appeal, lush landscaping, and the peaceful ambiance that defines this desirable neighborhood. Inside, soaring vaulted ceilings and oversized windows fill the open-concept living areas with abundant natural light, creating a warm and inviting atmosphere ideal for both everyday living and entertaining. The spacious kitchen serves as the heart of the home, featuring modern appliances, abundant cabinetry, and generous prep space, all flowing seamlessly into the dining and living areas. Just beyond, the cozy family room offers a wood-burning fireplace, creating the perfect gathering spot for relaxing evenings with family and friends. The first-floor primary suite provides a private retreat with a spacious walk-in closet and a beautifully remodeled en-suite bathroom featuring a soaking tub and separate shower. Upstairs, three additional bedrooms offer plenty of space for family, guests, or a home office. All bathrooms throughout the home have been tastefully remodeled, and new luxury vinyl plank flooring adds style, durability, and a fresh contemporary feel. Step outside to your own private Florida oasis. The enclosed, solar-heated pool invites year-round enjoyment, while the expansive side yard overlooking the pond provides exceptional outdoor living space. A fenced garden area and beautifully landscaped grounds complete this tranquil backyard retreat. Major updates provide peace of mind for years to come, including a new roof (2022), a new pool screen enclosure (2021), and numerous additional improvements that enhance both comfort and value. Ideally located in the heart of Winter Garden, Lake Amberleigh offers convenient access to charming downtown shops and restaurants, top-rated schools, major highways, Orlando International Airport, and world-famous Walt Disney World and other Central Florida attractions. This exceptional home truly offers the perfect blend of comfort, style, and location. Don't miss your opportunity to own this incredible property. Call today to schedule your private showing!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Joseph Newstreet (407-230-9901)

Remarks: Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat. Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb appeal. A custom front door opens to a partially screened wraparound front porch, perfect for morning coffee or evening chats. Inside, rich hardwood floors span the main level, complemented by abundant natural light, crown molding, plantation shutters, designer lighting, brass floor outlets in the living room & office, and ceiling fans throughout. The kitchen features granite countertops, a farmhouse sink, stainless steel appliances, tile backsplash, under-cabinet lighting, a beverage refrigerator, & a new Bosch dishwasher and microwave (2023). Open to the living & dining areas, it overlooks the front porch & connects seamlessly to outdoor living through French doors. A flexible front room serves as an office, study, or playroom. A powder room serves guests. The first-floor owner's suite overlooks the pool & offers dual granite vanities, a spa-style walk-in shower, linen storage, custom California Closets, & direct laundry room access. Upstairs, hardwood flooring continues throughout 3 spacious bedrooms, including one en-suite, plus two full baths and a generous loft ideal for theater, fitness, playroom, or guest retreat. A whole-home Generac natural gas generator keeps lights, air conditioning, & appliances running during outages. Step outside to one of Oakland Park's rare full-size Jandy-iAqualink-controlled saltwater pool & spa. The pool measures approximately 12' x 30' with depths from 3' to 5' & features an 8' x 12' sun shelf with bubbling fountain and umbrella sleeve. The approximately 6' x 8' spa includes four therapy jets and heats in 20-30 minutes. Equipment includes a 2.7 HP Jandy Variable-Speed Energy-Efficient Pump & Jandy 400,000 BTU natural gas heater. A travertine pool deck, oversized covered rear porch, vinyl-fenced yard with dual gates, & three-car garage with built-in storage racks complete the outdoor experience. Oakland Park offers a waterfront, golf-cart-approved lifestyle with two resort-style pools, a clubhouse, dog park, playgrounds, parks, & spectacular sunsets. Two blocks from the waterfront trail, minutes from the 22-mile West Orange Trail, & near multiple parks. Historic downtown Winter Garden is a golf cart ride away, offering Crooked Can Brewery, rooftop dining, boutique shopping, splash park, Farmers Market, live theater, golf cart parades, 5Ks, book clubs, poker nights, and more. Convenient access to major interstates, premier golf courses, shopping, & Central Florida theme parks. Additional features: fresh interior/exterior paint (2021), Apple HomeKit-compatible door locks, thermostats & ceiling fans, Apple Secure Video cameras at the doorbell, front entry, pool area & indoor locations, new remote-controlled high-velocity fans on both porches, Apple HomeKit-controlled owner's bath fan, outlets inside primary bath cabinetry, & a state-of-the-art termite detection and control system with full warranty. Lovingly maintained & thoughtfully enhanced throughout, this one-of-a-kind Oakland Park pool & spa home is a special opportunity. Your oasis is waiting. Make it yours.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: Under contract-accepting backup offers. Welcome to this exceptional 4-bedroom, 4-bath residence with a private office, expansive loft, and 2,831 square feet of beautifully designed living space in the highly sought-after McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. Perfectly positioned on a private corner end lot, this stunning home is complemented by a welcoming front porch and showcases timeless architecture, upscale designer finishes, and exceptional attention to detail. Step inside to discover soaring ceilings, abundant natural light, and beautiful white oak luxury vinyl plank flooring throughout the main living areas. A private office just off the foyer provides the ideal work-from-home space or flex room, while custom window treatments, plantation shutters, designer wallpaper, elegant accent walls, and custom built-ins create a warm yet sophisticated atmosphere. At the heart of the home, the gourmet chef's kitchen features custom cabinetry with upgraded hardware, quartz countertops, an oversized island with designer pendant lighting, a gas cooktop, custom vent hood, built-in wall oven, decorative tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room, where custom built-ins create the perfect gathering space for entertaining or relaxing. The thoughtfully designed floor plan includes a private first-floor guest suite with a full bath, ideal for guests or multigenerational living. Upstairs, an expansive loft offers flexible living space perfect for a media room, game room, or second family room. The luxurious primary suite is privately situated away from the secondary bedrooms and offers tray ceilings, designer accent walls, a spacious walk-in closet, and a spa-inspired en-suite bath featuring dual quartz vanities, a soaking garden tub, and a separate walk-in shower. Two additional upstairs bedrooms each feature walk-in closets, with one offering its own private en-suite bath, while another full bath serves the remaining bedroom and loft. Even the laundry room has been elevated with designer wallpaper, quartz folding countertops, and an included washer and dryer. Outside, the private corner homesite enhances both curb appeal and privacy, offering additional green space and a peaceful setting to enjoy the Florida lifestyle. Living in Oakland Park means embracing one of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market. With convenient access to Florida's Turnpike, SR-429, downtown Orlando, and Central Florida's world-famous attractions, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Erica Sadelfeld (407-427-0398)

Remarks: Welcome to this exceptional pool home in the highly sought-after gated community of Hickory Hammock in Winter Garden. Offering more than 3,600 square feet beautifully designed living space, this impressive five bedroom, four bathroom, 4 car garage residence blends timeless elegance with everyday functionality. From the moment you step inside, you'll be captivated by soaring ceilings, georgous formal dining space, elegant coffered and wainscoting details, custom built-ins, and an abundance of natural light. The open concept floor plan creates an effortless flow, making the home ideal for both intimate gatherings and grand entertaining. At the heart of the home, the gourmet kitchen overlooks the expansive living and dining areas, it features quartz counter tops, abundant cabinetry, generous prep space, and a layout designed for both entertaining and everyday living. A downstairs private home office offers a refined work from home setting, while the expansive upstairs loft is an entertainer's dream, complete with a projector and oversized movie screen, creating the perfect setting for cinematic experiences, game days, or a stylish media lounge. The luxurious primary suite serves as a peaceful retreat with a spacious walk-in closet and spa-inspired ensuite bath. Thoughtfully designed secondary bedrooms and bathrooms provide comfort and privacy for family and guests. Step outside to your own private outdoor oasis where a screened resort-style pool and covered lanai create the ultimate setting for year-round Florida living. Whether hosting guests or enjoying a quiet evening at home, this backyard is designed for relaxation and entertaining. Recent enhancements that showcase true pride of ownership, including a freshly repainted interior, whole home pressure washing, new landscape, and a professionally serviced and cleaned air conditioning system. Residents of the gated community of Hickory Hammock enjoy an exceptional lifestyle with resort-style amenities including a clubhouse, fitness center, community pool, playgrounds, dog park, scenic walking trails, fishing pier, and boat ramp access to the beauty of Johns Lake. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, top rated schools, shopping, dining, SR 429, Walt Disney World, and Orlando's world class attractions, this remarkable home offers the perfect balance of luxury, lifestyle, and convenience. Schedule your showing today!

Listing is courtesy of: HOGAN REALTY GROUP INC (321-474-2004)

Listing Agent: Kaitlin Sidders (407-797-2985)

Remarks: Along a charming brick street in one of the desirable areas of southwest Orange County, this beautifully updated 1938 cottage-style home offers a blend of historic character and modern convenience in the heart of downtown Winter Garden. On an oversized, fully fenced corner lot within the sought-after golf cart district, this rare gem is just blocks from historic Plant Street, the famed Plant Street Market, weekend farmers market, premier dining, shopping, entertainment and scenic West Orange Trail. This inviting three-bedroom, two-bath home features 1,273 square feet of thoughtfully updated living space with stylish laminate and ceramic tile flooring throughout, blending timeless charm with modern finishes. Inside, you'll find a functional layout with inside laundry, a warm and welcoming atmosphere, and a newer air-conditioning system for added peace of mind. Enjoy quiet mornings or relaxing evenings from the desired front and rear porches overlooking the fully fenced yard, ideal for entertaining, pets or simply enjoying the Florida lifestyle. The oversized double carport and extended driveway provide abundant parking, while the exterior storage room within the carport offers exceptional flexibility for hobbies, tools, golf cart accessories or additional storage needs. Homes with this level of charm, character and accessibility rarely become available in downtown Winter Garden. Combining an unbeatable location, oversized corner lot and the convenience of golf cart living just near everything Plant Street has to offer, this is a special opportunity to own a piece of one of Central Florida's beloved historic communities.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)

Listing Agent: Michael Mitchell, Jr (352-768-1712)

Remarks: Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: Maria Howard (410-422-3518)

Remarks: Finding nearly 4,000 sqft of beautifully UPDATED living space on an oversized CORNER LOT is increasingly rare. Add a full-width BALCONY overlooking the GOLF course, extensive RENOVATIONS throughout, and a backyard that extends well beyond the existing fence line, and this home immediately stands out. From the moment you step inside, you'll notice how effortlessly this unfurnished home flows. Whether you're looking for multiple living areas, a dedicated home office, fitness space, media room, or simply room to spread out, this flexible layout adapts to the way you live. At the heart of the home is the beautifully REMODELED KITCHEN, redesigned in 2022 with quartz countertops, an oversized island, abundant cabinetry, and a Samsung Bespoke appliance suite installed in 2024. It creates a natural gathering space before flowing seamlessly into the family room, where the fireplace provides a warm focal point for everyday living and entertaining. Luxury vinyl plank flooring runs throughout the home, while EVERY BATHROOM has been tastefully RENOVATED and FRESH interior PAINT gives the home a bright, contemporary, move-in-ready feel. Upstairs, the expansive LOFT has already been transformed into an impressive HOME CINEMA, complete with in-ceiling surround sound, dedicated audio equipment, a high-performance subwoofer, and discreet in-wall cable management. It also offers exceptional flexibility as an additional living area, games room, or creative workspace. One of the home's most distinctive features is the impressive full-width balcony spanning the rear of the property. Accessible from both the primary suite and the adjoining bedroom or office, it's the kind of OUTDOOR SPACE you'll genuinely use, whether that's enjoying your morning coffee overlooking the golf course, catching the evening breeze, or simply taking a quiet moment at the end of the day. Outside, the sense of space continues. The backyard feels like an extension of the home's living space, with a PRIVATE PUTTING GREEN, artificial turf, upgraded deck, patio lighting, and refreshed landscaping creating an inviting setting for relaxing or entertaining outdoors. The FENCED YARD provides a wonderful private outdoor space, but what many buyers won't immediately realise is that the property extends significantly beyond the current fence line, giving you even more usable land than first meets the eye. Combined with the generous side yard afforded by this oversized corner homesite, the amount of outdoor space is truly impressive. Equally valuable are the updates you may not immediately notice. Major improvements include a NEW ROOF (2022), high-efficiency HVAC system (2022), whole-home SOLAR system (2022), whole-home WATER SOFTENER and filtration system (2025), automatic irrigation system with timer, Alexa-compatible smart home features and an electric vehicle charging station. Set within the GUARD-GATED community of Stoneybrook West, residents enjoy championship golf, a WATERFRONT CLUBHOUSE overlooking Lake, resort-style pool, FITNESS center, TENNIS and BASKETBALL courts, playgrounds, PRIVATE BOAT RAMP with lake access, community boat storage, and 24-hour guarded security. Conveniently positioned near one of the community entrances, the home offers quick access to Winter Garden Village, shopping, dining, schools, and major roadways, combining exceptional convenience with one of Winter Garden's most sought-after lifestyles.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Zoe Attwood (407-516-9009)

Remarks: 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. 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. A rare blend of craftsmanship, luxury, and location—now at an even more compelling price.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Lora King (407-947-7653)

Remarks: Under contract-accepting backup offers. Welcome to 1209 Castleport Rd — your next chapter in Stoneybrooke West, a gorgeous golf-course community where everyday feels like a getaway. From the moment you arrive you’ll love the manicured fairways, peaceful walking paths, and neighborhood pride that make this community stand out. Step inside and imagine family mornings and movie nights in the bright, open living spaces. This home offers 5 spacious bedrooms and 3 full bathrooms — plenty of room for guests, a home office, or a hobby room. Thoughtful finishes and flexible room spaces make entertaining effortless and daily life comfortable. Location is everything: you’re minutes from theme parks, with fast highway connections for stress-free commutes and weekend escapes, plus easy access to shopping, dining, and services. Whether you’re teeing off on the greens, grabbing dinner nearby, or heading out for a day at the parks, 1209 Castleport Rd combines comfort, convenience, and that warm, community feel you’ve been looking for.

Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)

Listing Agent: Angela Magac (407-744-5557)