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

Remarks: Within the gated community of Canopy Oaks in Winter Garden, Parade of Homes award-winning Delray model by renowned builder A.R. Bailey Homes combines timeless architecture with curated upgrades rarely found in today’s market. Within an intimate enclave of only 49 homesites, this meticulously maintained home offers over 4,000 square feet of flexible multigenerational living, entertaining spaces and seamless indoor-outdoor Florida living. Ideally just minutes from Historic Downtown Winter Garden, Winter Garden Village, Orlando Health, the Roper YMCA, shopping, dining, recreation and major roadways including Florida’s Turnpike, SR 429, SR 408 and Interstate 4. A paver driveway, concrete tile roof, stone-accented exterior, wood-look garage doors, three-car garage and grand solid wood double-entry doors create a striking first impression. Inside, 10-foot ceilings in the great room, architectural details, abundant natural light, elegant finishes, and wood-look porcelain tile flooring throughout the first floor create a sophisticated yet welcoming atmosphere. The chef’s kitchen serves as the heart of the home, designed for everyday living and entertaining. Highlights include a natural gas cooktop with exterior vent, built-in wall oven, upgraded appliances, pot filler, oversized center island, 42-inch cabinetry with crown molding, under-cabinet lighting, designer tile backsplash and an expansive walk-in pantry overlooking the coffered-ceiling great room. A gated wine cellar adds a distinctive feature rarely found at this price point. The luxurious first-floor primary suite was designed as a spa-inspired retreat, featuring a beautifully appointed primary bath with premium finishes, dual vanities, an oversized walk-in shower, freestanding soaking tub and a spacious walk-in closet. A separate first-floor en-suite bedroom provides flexibility for guests, extended family, multigenerational living or a private home office. Upstairs, a second primary suite is complemented by two additional en-suite bedrooms, a spacious loft, guest powder bath and covered balcony, providing privacy and versatility for family and guests. Designed to embrace Florida’s indoor-outdoor lifestyle, dramatic corner-opening glass doors and expansive stacking sliders open to the covered lanai with a motorized retractable screen, creating effortless entertaining year-round. The backyard, accented by a stucco privacy wall, offers ample space for a custom pool, outdoor kitchen and additional outdoor living areas. The three-car garage provides generous space for vehicles, golf carts, storage and recreational equipment. Additional highlights include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, mudroom, reading nook and generous storage throughout. Residents of Canopy Oaks enjoy scenic recreational trails, a community playground and an exceptional Winter Garden location near shopping, dining, healthcare, recreation and everyday conveniences. Offering five en-suite bedrooms, seven baths, dual primary suites, a spa-inspired first-floor primary suite, wood-look porcelain tile throughout the first floor, a three-car garage, natural gas, award-winning design and an exceptional location within Canopy Oaks, this beautifully maintained residence presents an outstanding opportunity to experience refined Winter Garden living. Also available for lease (MLS #O6416527).

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Lisa Rutkowski (407-793-2416)

Remarks: Welcome to 14252 Creekbed Circle, a spacious and beautifully designed home located in the heart of Winter Garden, in Bradford Creek, one of Central Florida's most sought-after communities. Perfectly situated near Downtown Winter Garden, you'll enjoy convenient access to popular restaurants, boutique shopping, farmers markets, community events, walking trails, and entertainment year-round. This expansive 4-bedroom, 3.5-bath residence offers plenty of room for everyone with a versatile floor plan designed for modern living. The oversized bonus room provides endless possibilities and can be used as a home office, game room, media room, playroom, fitness area, or additional living space to fit your needs. The spacious layout features generous living and dining areas, creating the perfect setting for entertaining guests or enjoying everyday life. The large kitchen with a center island for entertaining and an abundance of cabinets for all of your cooking needs. The private owner's suite offers a relaxing retreat, while the additional bedrooms provide comfort and flexibility for family and visitors. With abundant living space, a desirable location, and easy access to everything Winter Garden has to offer, this home combines convenience, functionality, and lifestyle in one exceptional package. Near Winter Garden Village, Disney and Advent Health in Winter Garden with easy access to 429/408 and the Turnpike. Don't miss the opportunity to make this your next home. Garage equipped with Tesla Charger, Upstairs HVAC replaced 8/2025, Downstairs HVAC replaced 1/2026, Dishwasher replaced 12/2024, Luxury Vinyl Plank flooring installed 12/2025 and new interior paint 5/2026.

Listing is courtesy of: WATSON REALTY CORP (407-323-3200)

Listing Agent: Carla Robles (407-462-2347)

Remarks: Virtually Staged. Rarely does a property offer over an acre of land in the heart of Winter Garden. Tucked away in an intimate lake-access community, this beautifully refreshed pool home combines privacy, mature trees, and an unbeatable location just minutes from everything Central Florida has to offer. Set on a beautifully landscaped 1.1-acre lot with no rear neighbors, this stunning residence offers a rare opportunity to enjoy space, serenity, and flexibility in one of Winter Garden's most desirable locations. Designed for both everyday living and effortless entertaining, the home features fresh interior paint, new luxury vinyl plank flooring throughout the main living areas and bedrooms, a newer roof, new water heater, oven, range, custom woodwork, and a beautiful wood-burning brick fireplace that anchors the living space. The expansive covered lanai, refinished screened-in pool with a new pump, and spa create a true indoor-outdoor lifestyle, with multiple access points from the home and a kitchen pass-through window that opens directly to the entertaining area. Privately situated on the opposite side of the main 3 bedrooms, the light-filled bonus room features two closets, French doors, its own exterior entrance, and tranquil views of the mature landscaping. Paired with the adjacent full bath, it offers exceptional flexibility as a potential 4th bedroom, private guest suite, in-law suite, home office, or creative space. The 3rd full bath also serves as a convenient pool bath with direct outdoor access to the lanai. Outside, enjoy beautifully maintained gardens, mature trees, a fully fenced backyard, abundant outdoor living space, and a large detached storage building with electricity. Residents also enjoy private access to Black Lake and Lake Tilden, complete with a boat ramp, tennis court, pavilion, and the peaceful charm of one of Winter Garden's hidden-gem communities. Just minutes from Winter Garden Village, historic Downtown Winter Garden, major highways, area hospitals, and world-famous attractions including Disney World, Universal Orlando, and SeaWorld, this property delivers a combination of land, location, and lifestyle that is rare to find.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Erin Rison (407-844-8168)

Remarks: Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.

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

Listing Agent: Trevor Zwick (863-303-6114)

Remarks: Welcome to this first floor condo in the heart of Winter Garden! This 2 bedroom, 2 bath unit offers an excellent opportunity for both homeowners and investors. Enjoy the convenience of ground floor living with a private screened in patio, perfect for relaxing with your morning coffee or unwinding after a long day. Inside, you'll find a functional floor plan with a washer and dryer included, making move in even easier. The home is priced to reflect its potential and is ready for your personal touch with fresh paint and new flooring, allowing you to customize the space while adding instant value. Residents enjoy a variety of community amenities, including a swimming pool, basketball court, clubhouse, and community mailbox. The unit also comes with two designated parking spaces for added convenience. Ideally located near shopping, dining, entertainment, and major roadways, this condo offers affordability, convenience, and the opportunity to make it your own in one of Winter Garden's most desirable areas.

Listing is courtesy of: REVEL REALTY LLC (407-876-6448)

Listing Agent: Karen Grau (407-383-3230)

Remarks: Welcome to your own piece of Downtown Winter Garden paradise! This beautifully maintained 3-bedroom, 2.5-bathroom residence, built in 2019, offers the perfect blend of modern comfort, thoughtful design, and an unbeatable location just moments from one of Central Florida's most sought-after historic downtowns. Ideally situated just a short stroll from the award-winning Winter Garden Farmers Market, this exceptional home places you in the heart of one of Florida's most vibrant communities. Walk to the renowned Crooked Can Brewing Company, Garden Theatre, boutique shopping, charming cafés, and an outstanding selection of local restaurants, wine bars, and entertainment venues. Whether enjoying a weekend brunch, an evening out, or one of the many community events held throughout the year, everything Downtown Winter Garden has to give is just minutes from your front door. Inside, you'll immediately appreciate the bright, open-concept layout designed for comfortable everyday living and effortless entertaining. The spacious kitchen overlooks the living and dining areas, creating a warm, inviting atmosphere where family and guests naturally gather. Featuring modern finishes, generous cabinetry, quality appliances, and ample counter space, the kitchen is ideal for casual meals or hosting dinner parties. The highly desirable first-floor primary suite provides privacy and convenience with an en-suite bathroom and generous closet space. Also on the first floor are the laundry room, convenient half bath, and direct access to the attached two-car garage. Upstairs are two additional well-proportioned bedrooms and a full bathroom, creating the ideal setup for family, guests, or a dedicated home office. A standout feature is the dedicated surround-sound movie theatre, creating the ultimate in-home entertainment experience for movies, sporting events, and family movie nights. Step outside to your own peaceful retreat. The recently created butterfly garden provides a colorful outdoor sanctuary, thoughtfully landscaped to attract butterflies and pollinators while creating the perfect place to relax with your morning coffee or unwind after a busy day. Built in 2019, this home offers the advantages of modern construction, energy-efficient features, and low-maintenance living while combining timeless curb appeal with an exceptional floor plan. Opportunities to own a newer home within minutes of Historic Downtown Winter Garden are rare. Whether you're looking for a primary residence, a lock-and-leave lifestyle, or simply want to enjoy one of Central Florida's most desirable communities, this property delivers an exceptional combination of location, comfort, and lifestyle. Experience everything that makes Winter Garden one of Florida's most celebrated places to live—from its tree-lined streets and award-winning Farmers Market to the renowned West Orange Trail, live entertainment, breweries, dining, shopping, and year-round community events—all just a short walk from your front door. Agent is the Owner.

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

Listing Agent: Lloyd Hart (855-450-0442)

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

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Diane Sterling (407-761-0512)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home located in the highly desirable gated golf community of Stoneybrook West in Winter Garden. This move-in-ready residence features an open and spacious floor plan with separate living and dining areas, high ceilings, abundant natural light, and ceramic tile throughout. The upgraded kitchen offers granite countertops, ample cabinet space, and all appliances are included. The spacious primary suite features a large walk-in closet and an updated bathroom with skylights, dual vanities, a garden tub, and a separate shower. Enjoy outdoor living in the fully fenced backyard with a large patio, perfect for entertaining or relaxing. Recent updates and meticulous care make this home a true standout. Roof replaced in 2022. Property comes with solar panels. Residents enjoy resort-style amenities including a community pool, fitness center, tennis and basketball courts, playgrounds, lake access, fishing pier, boating, and 24-hour guarded gate security. Conveniently located near top-rated schools, shopping, dining, major highways, downtown Winter Garden, and Orlando's world-famous attractions. Don't miss this exceptional opportunity—schedule your private showing today!

Listing is courtesy of: REALTY ONE GROUP EVOLUTION (786-477-4715)

Listing Agent: Milena Nunez (407-247-1814)

Remarks: Welcome to 17314 Bal Harbour Drive, a beautifully upgraded pool home in the sought-after Waterside community in Winter Garden, where luxury finishes, smart-home technology, and breathtaking water views come together in one exceptional property. From the moment you arrive, the home’s elegant curb appeal, fully fenced backyard, and impressive architectural details set the tone for what awaits inside. Step through the front entry into a bright and inviting foyer featuring ceramic tile plank flooring, tray ceilings throughout, and thoughtfully designed living spaces filled with upscale finishes. At the front of the home, Bedroom 2 offers a custom California walk-in closet, making it ideal for guests or multigenerational living. Nearby, Bathroom 2 features a stylish stand-alone shower, tile backsplash, and upgraded vanity. The flex room is perfect for a home office, media room, or playroom and showcases decorative shiplap accents, double-pane windows, custom-made glass double doors, and window treatments that complement the space. Continue into the heart of the home, where the gourmet kitchen is designed to impress with quartz countertops, stainless steel appliances, under-cabinet lighting, a convection oven, spacious pantry, pendant lighting with dimmers, and two coffee bars. The adjacent formal dining room is ideal for entertaining and includes designer lighting, shades, and curtains that convey with the home. The expansive great room is perfect for everyday living and gatherings, featuring built-in surround sound and beautiful views of the outdoor living area. Privately situated on the main floor, the primary suite offers tray ceilings, can lighting, a decorative light fixture, and elegant window treatments. The spa-inspired primary bathroom includes dual quartz vanities, a tiled walk-in shower with twin shower heads, a water closet, linen closet, and an oversized California walk-in closet. Upstairs, engineered hardwood stairs lead to a spacious loft area and Bedrooms 3, 4, and 5. Bedroom 3 features French closet doors, Bedroom 4 includes a walk-in closet and ceiling fan, and Bedroom 5 offers French doors, making it ideal as a bedroom, office, or hobby room. Bathroom 3 is appointed with dual sinks, granite countertops, and a tub/shower combination. Step outside to your private backyard retreat. The covered lanai overlooks a stunning saltwater pool with a 5-foot deep end, sundeck, and serene views of Avalon Lake. Entertain with ease using the outdoor kitchen featuring a gas grill, sink, and mini fridge while enjoying the Florida lifestyle. Additional upgrades include Ecobee smart thermostats, a Lutron lighting system with dimmers, Alexa voice-controlled lighting, motion-activated closet lights, reverse osmosis system, water softener, washer and dryer, and Simply Safe doorbell and security cameras. For added peace of mind, the home also features a brand-new AC system with a 10-year warranty. Residents of Waterside enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, dock, and pavilion. Don’t miss this opportunity to own a move-in-ready luxury home with premium upgrades, exceptional outdoor living, and stunning water views in one of Winter Garden’s most desirable communities.

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

Listing Agent: Regina Cruz (352-988-7488)

Remarks: Commanding stunning views of Johns Lake, 16038 Johns Lake Overlook Dr rests in the desirable Hickory Hammock community of Winter Garden a lakefront enclave where natural beauty meets elevated, everyday luxury. This is more than a home; it's a lifestyle designed for those who appreciate space, comfort, and the calming presence of water just beyond their windows. Inside, 4,139 square feet unfold across a thoughtful, flexible layout with five bedrooms and five bathrooms. The main level anchors the home with two generous suites, including a refined primary and an oversized guest suite. Each offers serene water views, spa-inspired bathrooms, and a true sense of privacy that makes hosting effortless. Venture upstairs to discover a second secluded primary suite your personal sanctuary. Here, you can wake to panoramic lake views, relax in the garden bath, or step onto your private balcony to take in unforgettable sunsets over the water. The heart of the home is an open concept living area that flows seamlessly into a chef's dream kitchen. Premium appliances, gleaming granite countertops, and custom cabinetry create a space equally suited for quiet mornings and lively gatherings. When it's time to unwind, a dedicated theatre loft provides the perfect setting for movie nights and lazy weekend afternoons. Step outside, and the entertaining possibilities feel endless. The expansive outdoor living area boasts a full outdoor kitchen finished in Brazilian granite, a sparkling pool with an infinity edge hot tub, and multiple spaces for lounging and dining beneath the Florida sky. Just steps away, your covered private boat dock complete with boat and jet ski lifts opens the door to endless days of boating, fishing, and watersports on Johns Lake. For those who love to play, the backyard even includes a 5-hole putting green and a 2-hole chipping green, ideal for sharpening your short game without ever leaving home. Every detail here reflects a rare blend of craftsmanship, comfort, and connection to the water. Surrounded by natural beauty and premium amenities, this property delivers the kind of tranquil lakefront living that so many search for and so few ever find. Opportunities to own a home like this, in one of Winter Garden's most sought after communities, simply don't come along often. Come experience it for yourself, and imagine the life waiting here. Schedule your private showing today before this exceptional retreat is gone!

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

Listing Agent: Drew Belani (407-203-9441)

Remarks: Located in the highly desirable gated community of Glynwood in Winter Garden, this spacious 5-bedroom, 4-bath pool home offers over 3,500 square feet of living space on a private cul-de-sac lot. The versatile floor plan features a first-floor owner's suite, dedicated office/den, formal and casual living areas, and an upstairs bonus/media room with an additional bedroom and bath—ideal for guests, multi-generational living, or a home theater. The screened pool and spa create a private backyard retreat, while the 3-car garage (AC by Modern Wall Unit and Upgraded Garage Floor Coating) provides ample storage and parking. Residents enjoy access to community amenities including a pool, tennis courts, playground, and gated entry. Conveniently located near Winter Garden Village, historic downtown Winter Garden, major highways, shopping, dining, and area attractions.

Listing is courtesy of: CHOICEPOINTE REALTY, INC. (888-246-5758)

Listing Agent: Mary Dees (407-468-8285)

Remarks: Welcome to this stunning, like-new home that perfectly blends luxury, comfort, and modern design in the highly desirable community of Hull Island. Boasting five spacious bedrooms and four full bathrooms, this thoughtfully designed residence offers an ideal layout for both everyday living and entertaining. This home offers two spacious owner’s suites, one conveniently located on the first floor and another upstairs, making it ideal for multigenerational living, extended guests, or added privacy. Step inside to soaring high ceilings and an open-concept floor plan filled with natural light. The heart of the home is the gourmet gas kitchen, featuring 42-inch cabinetry, elegant quartz countertops, a large center island, built-in convection oven, stainless steel appliances and premium finishes throughout. A dedicated beverage station with a separate bar refrigerator provides the perfect space for entertaining guests. Upstairs, you'll find an expansive loft that offers endless possibilities as a media room, game room, home office, or additional living space. Outside, enjoy your own private backyard retreat complete with a sparkling pool, ideal for relaxing or hosting family and friends year-round. The garage is equipped with overhead storage shelving, providing ample space to keep seasonal items and equipment neatly organized. With its spacious layout, upscale finishes, abundant storage, and exceptional amenities, this beautifully maintained home is truly move-in ready and offers the perfect combination of elegance, functionality, and Florida living at its finest. This community features a pool pool, nature trails, playground, dog park, and private dock. Conveniently located near shopping, dining, main highway and more.

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: Vilmari Caraballo (407-583-9870)

Remarks: Welcome to this beautifully maintained 5-bedroom, 3-bathroom single-story home in the highly sought-after gated community of Belle Meade — zoned for Whispering Oak Elementary (10/10 GreatSchools rating, top 5% of all schools in Florida), SunRidge Middle, and West Orange High School. With 2,918 square feet of thoughtfully designed living space, a 3-car garage, and a fenced corner lot spanning 0.27 acres, this home offers the space, privacy, and top-tier school access today's families are searching for. Major systems have already been taken care of for you — enjoy true peace of mind with a brand new roof (February 2024), backed by a CertainTeed SureStart warranty that's fully transferable to the new owner, and a brand new Trane 5-ton AC system (2025) with a 10-year warranty through 2035. No surprise repairs, no looming replacements — just move in and relax. Inside, soaring cathedral and vaulted ceilings, tray ceilings, crown molding, and wood flooring create an elegant, open feel throughout. A separate laundry room adds everyday convenience, and the fifth bedroom functions as a versatile den/utility space — ideal for a home office, playroom, or guest suite. The primary suite is a true retreat, featuring dual walk-in closets, dual vanities, a spa-style soaking tub, a separate standing shower, and a private water closet. Step outside to your fully screened and covered patio — perfect for entertaining or simply enjoying Florida's year-round sunshine, rain or shine — overlooking the private, fenced backyard. Belle Meade is a secure, gated community known for its lush landscaping, sidewalks, welcoming neighbors, and an on-site dog park. You're just minutes from Winter Garden Village at Fowler Groves — Central Florida's premier outdoor shopping and dining destination — and a short drive from historic Downtown Winter Garden's Plant Street, home to the award-winning Saturday Farmers Market, Crooked Can Brewing Company, and some of the area's best restaurants. Lake Apopka and several highly rated golf courses, including West Orange Country Club and Orange County National Golf Center (home to PGA Tour and LIV Golf events), are also just minutes away. Commuters and theme park lovers alike will appreciate the unbeatable location: Walt Disney World is approximately 15–25 minutes away via SR 429, with Universal Studios and SeaWorld each roughly 20–30 minutes via the Florida Turnpike. Downtown Orlando is approximately 20–25 minutes away via SR 408 or SR 50, and Orlando International Airport is about 30–35 minutes via the Turnpike. This is a rare opportunity to own a move-in ready home with major systems already updated, zoned for one of Florida's top-rated elementary schools, in one of Winter Garden's most desirable gated communities. Schedule your private showing today!

Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)

Listing Agent: Nikhil Vashist (352-901-3786)

Remarks: Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside community, you will find this beautifully designed residence, blending timeless sophistication with modern comfort, offering an open floor plan, designer finishes, and exceptional indoor-outdoor living. From the moment you arrive, the charming covered front porch, mature landscaping, and inviting curb appeal set the tone. Inside, you're greeted by wide-plank luxury vinyl flooring, soaring ceilings, crown molding, and sun-filled living spaces designed for both everyday living and effortless entertaining. The gourmet kitchen is a true showpiece featuring granite countertops, an oversized center island with seating, farmhouse sink, shaker cabinetry, stainless steel appliances, gas cooktop, double ovens, subway tile backsplash, a custom, handmade hood and designer pendant lighting. Flowing seamlessly into the spacious dining area and family room, this home is ideal for gathering with family and friends. Large sliding glass doors open to an expansive covered lanai with a stunning wood-finished ceiling, creating the perfect space to dine outdoors or just relax. The fully fenced backyard provides privacy, while maintaining a low-maintenance lifestyle. As you journey to the second level, you are greeting by a spacious loft, creating a retreat for unwinding and more closet space. Two large, additional bedrooms and a full bathroom are set off from the primary suite. Escape to your luxurious primary suite, offering a spacious walk-in closet and a beautifully upgraded spa-inspired bath, complete with a custom dual-sink vanity with quartz countertops, elegant gold fixtures, an oversized walk-in shower, and designer tile extending to the ceiling. Additional highlights include double-pane windows, custom window treatments, upgraded light fixtures, abundant storage, an oversized laundry room and pantry and thoughtful designer touches throughout. Residents enjoy outstanding resort-style amenities including a lakeside community pool, clubhouse, fitness center, playground, unfenced dog park and community dock. Ideally located in the heart of Winter Garden, this exceptional home is just minutes from shopping, dining, entertainment, theme parks, major highways, and top-rated schools. This isn't just a home; it's a lifestyle. Book your showing today!

Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-394-5900)

Listing Agent: Wendy Moore (678-575-5596)

Remarks: Located in the Golf Cart District and less than one mile from Historic Downtown Winter Garden and directly across from the West Orange Trail, this beautifully maintained 3 bedroom, 2 bath home in the Gated Community of Lakeview Reserve offers the perfect blend of location, comfort, and updates. The desirable split floor plan features spacious living and dining areas with an open concept kitchen at the heart of the home. Large windows throughout provide abundant natural light, while the kitchen offers a cozy breakfast nook and overlooks the backyard. The primary suite is a private retreat featuring a custom wood accent wall, soaking tub, and separate walk in shower. Two additional bedrooms are situated on the opposite side of the home, providing privacy for family or guests. Step outside to enjoy the spacious fenced backyard and screened lanai, perfect for relaxing or entertaining. Recent updates include a new roof (2018), exterior paint (2018), fence (2022), screened lanai (2022), gutters (2022), new sod (2025), and brand new carpet. Residents of Lakeview Reserve enjoy the security of a gated entrance, a covered community dock with scenic lakefront seating, and a prime location near shopping, dining, and all that Downtown Winter Garden has to offer. Top rated elementary and middle schools are within walking distance, making this move in ready home an exceptional opportunity in one of Central Florida's most sought after communities.

Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)

Listing Agent: Jennifer Mitchell (803-414-1133)

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

Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)

Listing Agent: Janelle Conway (407-595-0009)

Remarks: Looking for a move-in ready home in Winter Garden with modern upgrades, an ideal location, and a true sense of community? Welcome to this beautifully maintained 3-bedroom, 3-bathroom home in the highly desirable Oakland Park neighborhood. Designed for today's lifestyle, this home features a bright open-concept floor plan, abundant natural light, spacious living areas, and a functional layout that's perfect for both everyday living and entertaining. Premium upgrades include gas appliances, elegant plantation shutters, and stylish finishes throughout, offering a turnkey, low-maintenance home you can enjoy from day one. Located in one of Winter Garden's most sought-after golf cart communities, Oakland Park offers resort-style amenities, scenic trails, parks, green spaces, and top-rated schools, creating the perfect setting for an active, connected lifestyle. Just minutes from Historic Downtown Winter Garden, you'll have easy access to the nationally recognized farmers market, local restaurants, boutique shopping, coffee shops, seasonal festivals, live entertainment, and the West Orange Trail. Whether you're searching for a close knit neighborhood, a home near downtown Winter Garden, or a community with exceptional amenities, this property checks every box. Don't miss this opportunity to own a beautifully upgraded home in one of Central Florida's most desirable communities.

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

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Under contract-accepting backup offers. Price Improvement! Seller says Sell it! Offering $5,000 Buyers Incentive at closing. Welcome to established Regency Oaks subdivision in Stonecrest, in the heart of Winter Garden! Situated on a desirable corner lot, this screened-in POOL home offers an incredibly flexible floor plan designed to fit today's lifestyle. Listed as a 3-bedroom home, it also features a spacious flex room overlooking the pool and backyard, along with a separate oversized bonus room that can easily serve as an additional bedroom, home office, media room, playroom, fitness studio, guest retreat, or additional living space. The split-bedroom layout provides privacy, while the primary suite features a walk-in closet, garden tub, and separate shower. Fresh interior paint and updated laminate flooring enhance the home's inviting feel. Step outside to your private backyard oasis complete with a sparkling pool, mature shade trees, a side yard for gardening and a pool safety fence—creating the perfect setting for entertaining or relaxing while enjoying Florida's indoor-outdoor lifestyle. Recent improvements include a new roof (2023), 2017 air handler, 2018 A/C condenser, and a recently serviced irrigation system for added peace of mind. Residents of Regency Oaks enjoy low monthly HOA fees and outstanding community amenities including scenic walking trails around a picturesque pond with benches, a clubhouse, community pool, and two neighborhood parks/playgrounds. Ideally located walking distance of Winter Garden Village at The Grove and just minutes from Historic Downtown Winter Garden, the West Orange Trail, major highways, shopping, dining, entertainment, top rated schools and Central Florida's world-famous attractions. Orlando International Airport and Florida's east coast beaches are both approximately an hour away.

Listing is courtesy of: METRO CITY REALTY (407-237-3331)

Listing Agent: Beatrice Miranda (407-592-4448)

Remarks: Under contract-accepting backup offers. Luxury At its Finest. This Beautiful Immaculate Open Concept 4 bedrooms, 4 baths residence featuring a spacious loft with a full bath. Loft on 2 nd Floor can potentially be used as a 5th bedroom. Ideal for guests retreat, home office, media lounge, media room or additional entertainment for the entire family. The Amazing Gourmet Chefs kitchen with under cabinet lighting Gas stove, double oven showcases an extra large extended island perfect for entertaining. Complemented by elegant finishes. Open concept living spaces and exceptional comfort throughout the home in its entirety. French Doors gives access to the resort style pool with 4 therapy jets, bubblers on the sun shelf, custom hand rail with multi led lights with a Wet Edge Pool Interior. Elegant Pavers. The Pool is 3 ft on the shallow end and 6 ft on the deep end and measures 15 x 31. This home is taken care with lots of Pride and Tender Loving care. This home sits on a corner Lot with lots of privacy for all entertainment and relaxation. Garage has overhead racks for extra storage. This is a very small community that is peaceful and tranquil for great evening walks. By Appointment Only. Thank You.

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)

Listing Agent: Tracy Hampstead (407-803-3137)

Remarks: Under contract-accepting backup offers. SHOW STOPPER! Welcome to 15587 Hamlin Blossom - in the highly sought-after gated community of HICKORY HAMMOCK. A rare find, this Ashford model by M/I Homes is one of only six Ashford floor plans built in the community. Every detail of the 1860 sq. ft has been thoughtfully designed and meticulously cared-for, creating a TURNKEY experience unlike any other. Start off on your paver driveway and enjoy the handpicked lush new landscaping and welcoming porch-sitting area where you can immediately enjoy the outdoor Florida lifestyle. NEW EXTERIOR PAINT. Once inside you are greeted with perfection. NEW luxury vinyl flooring in each bedroom. NO CARPETS throughout the entire SINGLE STORY home. A foyer that immediately impresses with crafted lighting fixtures and perfectly placed decor. SPLIT FLOOR PLAN creates privacy for the two bedrooms and bath in the front of the home. Double vanity with UPGRADED lighting and hardware to elevate the bathroom space. The OPEN FLOORPLAN and dining room/living room combo is perfect for entertaining guests. Create the ideal ambiance with your ALEXA-enabled recessed lighting. A chef’s dream kitchen with BRAND NEW refrigerator, NEW dishwasher, and NEW garbage disposal. The primary suite is perfectly appointed with classic upgrades and reading nook. The HIGHLIGHT of the home is the wraparound paver patio with outdoor living/dining room space and OUTDOOR KITCHEN all under a screen enclosure overlooking a fully fenced, newly landscaped outdoor and garden area. Other upgrades include NEW washer/dryer, NEW HVAC components, NEW TESLA charging station. Hickory Hammock is a special enclave of Winter Garden that overlooks John’s Lake. Residents enjoy water views, private fishing pier, tennis courts, beach volleyball courts, nature trails, resort-sized swimming pool, fitness center, clubhouse, and nature trails. Located in the heart of Winter Garden and Horizon West, this home is approximately 5 minutes from SR 429, 10 minutes from Hamlin Town Center, 10 minutes from Downtown Winter Garden, and approximately 25 minutes from Walt Disney World. Residents enjoy convenient access to shopping, dining, entertainment, top-rated schools, major employment centers, and everything that makes Winter Garden one of Central Florida's most desirable places to live. Contact list agent for full list of upgrades AND seller’s complete maintenance schedule/records. Homes this well cared for do not come on the market often. See it for yourself today!

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Michelle Zimmerman (732-616-6019)