Location: Winter Garden
Do Not Show Listings
12103 EASTMOOR DR, WINTER GARDEN, FL 34787
$445,00023 Days on yellowkey MLS ID: O6409071
REDUCED by $5,000 (1.1%) on 06/04/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1604 Built: 2024Monthly Fee: $225 Tax: $6,795 (2025)Community: Encore/Ovation Ph 4BSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,795
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: Welcome to this BEAUTIFULLY MAINTAINED 3-bedroom, 2-bath home in the highly desirable Encore at Ovation community in Winter Garden, where modern style, energy efficiency, and LOW-MAINTENANCE LIVING come together perfectly. Built in 2024, this single-story residence still FEELS BRAND NEW and currently stands out as the only home available in the neighborhood, making it a RARE OPPORTUNITY in one of Winter Garden’s most sought-after communities. From the moment you arrive, the home impresses with its beautiful landscaping, charming front porch, and EXCEPTIONAL CURB APPEAL. The HOA even includes LAWN AND LANDSCAPE MAINTENANCE, allowing you to enjoy a carefree lifestyle in this walkable community. Step through the elegant GLASS-PANELED FRONT DOOR into a bright and inviting open-concept layout where the Living Room, Dining area, and Kitchen flow seamlessly together beneath SOARING CATHEDRAL CEILINGS. Windows throughout the home fill the space with ABUNDANT NATURAL LIGHT, enhancing the airy and welcoming atmosphere while STYLISH TILE FLOORING throughout the main living areas adds both beauty and easy maintenance. The bright designer Kitchen is the heart of the home, featuring white cabinetry, quartz countertops, a FARMHOUSE SINK, stainless steel SAMSUNG APPLIANCES, a gas stove, closet pantry, and a spacious breakfast bar, creating the perfect space for entertaining or everyday living.The thoughtfully designed SPLIT-BEDROOM FLOOR PLAN offers both comfort and privacy. Tucked away at one end of the home, the Primary suite serves as a peaceful retreat, featuring a spacious walk-in closet and a BEAUTIFULLY DESIGNED EN SUITE BATH with dual sinks, a step-in shower, and a linen closet. On the opposite side of the home, two additional bedrooms each feature their own WALK-IN CLOSETS and share a full bath, making them ideal for guests, family, or a home office. Conveniently located near the primary suite, the Laundry Room comes complete with STORAGE CABINETRY, washer, and dryer for added functionality. Step outside to enjoy the COVERED SIDE PATIO with paver stone flooring, a perfect private space for morning coffee or evening relaxation. A private entrance from the patio leads directly to the REAR-FACING GARAGE with EPOXY FLOORING, preserving the home’s charming streetscape and curb appeal. Residents of Encore at Ovation enjoy OUTSTANDING AMENITIES, including a sparkling resort-style pool, clubhouse, fitness center, dog park, playground, included internet service, and LAWN AND LANDSCAPE MAINTENANCE—creating a true resort-inspired lifestyle. Located in Winter Garden, this home is JUST MINUTES from Walt Disney World Resort, making world-class entertainment, dining, and shopping incredibly convenient. You’ll also enjoy EASY ACCESS to Hamlin Town Center, featuring popular restaurants, boutiques, movie theaters, and waterfront dining, as well as NEARBY GOLF COURSES, nature trails, and MAJOR ROADWAYS for commuting throughout Central Florida. Zoned for TOP-RATED SCHOOLS and offering a perfect blend of modern design, ENERGY EFFICIENCY, and low-maintenance living, this exceptional Encore at Ovation home is an incredible opportunity to enjoy the very best of the Winter Garden lifestyle. Call and schedule your tour today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
8275 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$555,00064 Days on yellowkey MLS ID: TB8496196
REDUCED by $10,000 (1.8%) on 06/09/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2019 Built: 2017Monthly Fee: $312 Tax: $5,109 (2025)Community: Waterleigh Ph 1BSpa: YesSingle Family
Taxes:$5,109
Elementary School: Panther Lake Elementary
Remarks: **New landscaping completed** Welcome to Waterleigh Phase 1 in Horizon West, Winter Garden, one of the most desirable communities in the area, known for resort-style amenities, scenic lakes, and top-rated schools. This rare one-story Arbor floor plan offers an open-concept layout with a highly sought after private fenced backyard - perfect for relaxing, entertaining, and enjoying Florida living at its best. This home features an extended screened-in lanai & patio upgrade, private backyard with a hot tub, cozy electric fireplace, dedicated home gym space, tandem 3-car garage, fresh exterior and interior paint. This home is move-in ready with thoughtful upgrades. Minutes from Hamlin Town Center, shopping, dining, and entertainment, plus quick access to Disney and major highways. Please schedule a showing to come view this rare opportunity to own a single-story home in Waterleigh Phase 1.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Timothy Shepard (727-204-9618)
5963 GLORY BOWER DR, WINTER GARDEN, FL 34787
$523,000359 Days on yellowkey MLS ID: O6318887
REDUCED by $6,950 (1.3%) on 06/09/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2128 Built: 2020Monthly Fee: $91 Tax: $5,092 (2024)Community: Hamilton Gardens Ph 2A & 2BSingle Family
Taxes:$5,092
Elementary School: Hamlin Elementary
Tax Year: 2024
Middle School: Hamlin Middle
Remarks: Welcome to 5963 Glory Bower Drive, Winter Garden, FLorida a beautifully maintained Home 3 bedroom, 2.5 bathrooms, plus office space, offering over 2,120 square feet of thoughtfully designed living space. This modern residence features an open-concept layout perfect for both everyday living and entertaining. The gourmet kitchen is equipped with granite countertops, stainless steel appliances, ample cabinetry, and a gas range. The home also features a gas water heater, providing efficiency and convenience. The spacious primary suite offers a walk-in closet and a luxurious en-suite bath, creating a comfortable and private retreat. One of the standout features of this home is the solar panel system, providing incredible energy efficiency and keeping the average monthly electric bill at just $33. Enjoy the Florida lifestyle in the private patio perfect for relaxing or hosting guests. Conveniently located near top-rated schools, shopping, dining, and just minutes from Disney. This move-in ready home is the perfect blend of comfort, sustainability, and location.
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Maria Poleo (407-622-9247)
15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787
$595,0005 Days on yellowkey MLS ID: O6414996
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2420 Built: 2024Monthly Fee: $96 Tax: $8,683 (2025)Community: Osprey Ranch Ph 1Single Family
Taxes:$8,683
Remarks: Welcome to 15143 Blue Peacock Lane in Winter Garden’s Osprey Ranch, a beautifully finished two-story home offering a bright open concept layout, updated finishes, and easy indoor-outdoor living. The main level features light wood-look flooring, recessed lighting, and a spacious living and dining area that flows seamlessly into the chef’s kitchen. Designed with both everyday function and entertaining in mind, the kitchen showcases white cabinetry, stone counters, a large center island, tile backsplash, stainless steel appliances, a gas cooktop, wall oven, and modern pendant lighting. Sliding glass doors open to a covered rear patio and fenced backyard, creating a comfortable extension of the living space. Upstairs, the primary suite offers soft carpet, a tray ceiling, ceiling fan, walk-in closet, and a spa-inspired en suite bath with dual sinks, a large glass-enclosed shower, private water closet, and modern finishes. Additional bedrooms feature carpet and natural light, while the upstairs bonus/flex area provides useful extra space for work, play, or relaxation. Osprey Ranch offers attractive community amenities, including a resort-style pool, clubhouse area, playground, open green space, and walking areas, all in a convenient Winter Garden location near shopping, dining, and everyday conveniences.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Jorge Martinez, Jr (407-513-2366)
15419 UGLIS ALY, WINTER GARDEN, FL 34787
$565,00044 Days on yellowkey MLS ID: O6403047
REDUCED by $10,000 (1.7%) on 06/03/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2270 Built: 2018Monthly Fee: $60 Tax: $8,121 (2025)Community: Highlands/Summerlake Grvs Ph 2Single Family
Taxes:$8,121
Elementary School: Summerlake Elementary
Remarks: Welcome to 15419 Uglis Aly, a uniquely positioned Horizon West home offering rare privacy, lifestyle, and convenience just minutes from Disney. This property faces open green space with no immediate front neighbors, creating a rare sense of privacy and openness. Enjoy nightly Disney fireworks views from home, with Grand Floridian approximately 12 minutes door to door. Built by K. Hovnanian, this open-concept home features surround sound, full ethernet wiring throughout, a bright sunroom, double ovens, stainless appliances, and flexible living spaces ideal for modern family life. Upstairs offers 3 spacious bedrooms, a dedicated laundry room, and a versatile loft—an option many similar homes in the area have converted into a 4th bedroom. The primary suite includes dual walk-in closets and an en-suite bath. The backyard is designed for low-maintenance entertaining with premium artificial turf, a covered lanai, and extended pavers. An oversized 20’ x 24’ garage plus one of the longest driveways in the neighborhood provide exceptional parking and storage. Just steps from the playground, green space, and mailboxes without crossing a street, plus access to resort-style amenities including pool, tennis, dog park, grills, and golf-cart-friendly access to shops, dining, and top-rated schools. A rare move-in ready opportunity combining privacy, smart upgrades, and the Horizon West lifestyle.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Evan Caulfield (407-432-9767)
17167 WRITING ALY, WINTER GARDEN, FL 34787
$535,00032 Days on yellowkey MLS ID: O6406920
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2486 Built: 2020Monthly Fee: $110 Tax: $7,916 (2025)Community: Storey Grove Ph 1BSingle Family
Taxes:$7,916
Remarks: Located in the heart of Horizon West, 17167 Writing Aly offers the space, flexibility, and location buyers are looking for in Winter Garden. Just minutes from Hamlin Town Center, the 429, Disney, and Downtown Winter Garden, this home is positioned in one of Central Florida’s fastest-growing areas while still offering a true neighborhood feel with community green spaces, walking paths, and resort-style amenities nearby. Inside, the freshly repainted interior feels bright, clean, and move-in ready. The open-concept main living area flows seamlessly into the kitchen and dining spaces, creating a layout that works well for both everyday living and entertaining. One of the standout features of this floorplan is the rare dual primary suite setup, with one primary bedroom conveniently located downstairs and a second oversized primary suite upstairs, giving flexibility for multi-generational living, guests, or added privacy. Step outside to your private outdoor courtyard, perfect for grilling, relaxing, or creating an inviting entertaining space between the home and detached two-car garage. With thoughtful layout options, fresh interior updates, and a location close to everything Horizon West has to offer, this home checks boxes that are hard to find at this price point.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787
$499,90089 Days on yellowkey MLS ID: O6391117
REDUCED by $5,100 (1.0%) on 05/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2082 Built: 2017Monthly Fee: $159 Tax: $7,996 (2025)Community: Watermark Ph 2CSingle Family
Taxes:$7,996
Remarks: Welcome to 9107 Grand Island Way, a beautiful Corner Lot Home in the heart of Horizon West’s Watermark community! This home is the perfectly balance of comfort, style, and convenience, designed for both everyday living and entertaining. Upon entering the front door, you will see your updated, modern kitchen with granite countertops, modern 42" cabinets and modern pendant lights overlooking your spacious living room. You will space for a nice dining room table to entertain as well as a half bathroom and the entrance to the 2 car garage! Upon walking up the modern staircase, you will find a very nice spaced loft/entertainment room, to where you can have your private second living room, office or movie theater room! The primary bedroom provides a relaxing and spacious space with a nice sized primary bathroom and walk in closet, while the additional bedrooms offer flexibility for family, guests, or a home office. As this is a corner lot, there home is filled with natural light. flowing seamlessly into the kitchen and dining space. One of the most unique aspects of this property is its prime corner location directly across from the vibrant Horizon West Retail Center, placing you just steps from such stores like Starbucks, New York Beer Project, 7-11 and Walgreens and more! Enjoy the rare ability to walk or bike to dining, entertainment, and local hotspots while still enjoying the privacy of a residential neighborhood. Residents of Summerlake enjoy resort-style amenities including a community pool, clubhouse, fitness center, dog parks, playgrounds and more! With easy access to Interstate 429, Hamlin Town Center, top-rated schools, Orange County National Golf Center and Walt Disney World just minutes away, this home offers the perfect balance of lifestyle and location in one of Winter Garden’s most sought-after communities conveniently located in the middle of everything!
Listing is courtesy of: FHG REALTY, LLC (407-505-7600)
Listing Agent: Jeff Inman (407-505-7600)
15625 SYLVESTER PALM DR, WINTER GARDEN, FL 34787
$1,093,000128 Days on yellowkey MLS ID: O6379346
REDUCED by $12,000 (1.1%) on 06/08/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3886 Built: 2018Monthly Fee: $360 Tax: $9,571 (2024)Community: Lakeshore Preserve Ph 1Single Family
Taxes:$9,571
High School: None
Remarks: WELCOME TO A TRULY EXCEPTIONAL HOME in the highly sought-after community of Lakeshore Preserve in Winter Garden, where luxury, comfort, and lifestyle come together seamlessly. This beautifully upgraded Toll Brothers Madeira floor plan offers 5 bedrooms, 4.5 bathrooms, and a 3-car tandem garage, and feels practically brand new, having been gently lived in by only a couple. This home features a private lot and a tranquil backyard, offering the peace and privacy many buyers desire while still enjoying all the benefits and conveniences of a vibrant community. From the moment you enter, the barrel ceiling foyer and soaring 10-foot ceilings create a grand yet inviting first impression. Natural light fills the open layout, drawing you into the heart of the home, a stunning gourmet kitchen designed for both everyday living and entertaining. Enjoy upgraded cabinetry, designer hardware and faucets, pull-out drawers, a wood plank backsplash accent wall, a spacious center island with breakfast bar, and a butler’s pantry for added functionality and elegance. The kitchen flows seamlessly into the family room, highlighted by a tray ceiling and pocket sliders that open to your private outdoor oasis. The extended screened lanai overlooks a gorgeous custom pool featuring a waterfall, LED illumination, and fully automated smart controls accessible from your phone, true resort-style living at home. The patio is pre-plumbed for an outdoor kitchen with water hookups, and the outdoor space is elevated with Shell Beach Tumbled Versailles Pattern pavers, a fully fenced yard, landscape lighting, a retaining wall, and an additional 10x10 paver patio for even more entertaining space. Downstairs, guests will appreciate a private bedroom and full bath, plus an additional half bath for convenience. Home theater speakers are pre-wired on both the first and second floors, adding built-in entertainment value. Upstairs, a spacious loft anchors the remaining bedrooms, creating the perfect second living area. The owner’s suite is a true retreat featuring dual vanities, a soaking tub, a glass-enclosed walk-in shower, and a custom built-in closet. Additional bedrooms include a Jack-and-Jill setup, a private en-suite, and a flexible room ideal for an office, gym, or craft space. Laundry is conveniently located upstairs. Bonus Magic: Enjoy nightly views of the Magic Kingdom fireworks right from your home. Families will appreciate the proximity to highly rated, A-rated schools, providing excellent educational opportunities just minutes away. Living in Lakeshore Preserve means access to resort-style amenities including a lakefront clubhouse, pool, fitness center, playgrounds, dog park, sand volleyball, canoeing, and community events: all in the heart of the Hamlin area, close to top shopping, dining, major highways, and everyday conveniences. This isn’t just a home: it’s a lifestyle!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Deep Mehta, Pa (407-702-7029)
10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787
$1,170,000205 Days on yellowkey MLS ID: O6361968
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4305 Built: 2020Monthly Fee: $159 Tax: $13,997 (2024)Community: Watermark Ph 4Single Family
Taxes:$13,997
Remarks: Welcome Home! This beautifully renovated 4,305 sq. ft. single-family residence offers the perfect blend of modern upgrades and inviting comfort, located in one of Winter Garden’s well sought-after communities. Discover elegant porcelain tile flooring throughout the first floor, leading to a spacious, updated kitchen featuring quartz countertops, a smart cooktop, and decorative glass cabinetry, ideal for both everyday living and entertaining. The gorgeous master suite includes a custom built-in walk-in closet, providing both style and functionality. With 6BR/5BA, there’s plenty of space for family and guests alike. Enjoy Florida living at its finest in your outdoor oasis, complete with a gazebo and a built-in fire pit seating area, perfect for relaxing evenings or weekend gatherings. The three-car split garage adds convenience and ample storage.Recently renovated and freshly painted, this home is truly move-in ready. Located in a wonderful community offering two sparkling pools and a playground, you’ll love the nearby amenities that make Winter Garden such a special place to live. Tour Today!
Listing Agent: Shi Knoblock (407-719-8651)
12362 BRACCO ST, WINTER GARDEN, FL 34787
$515,00043 Days on yellowkey MLS ID: O6404125
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2094 Built: 2023Monthly Fee: $105 Tax: $8,231 (2025)Community: Highland Rdg Ph 2Single Family
Taxes:$8,231
Remarks: Welcome to this exceptional home located in the highly sought-after Highland Ridge community. This beautifully maintained 4-bedroom, 2 full bathroom and 1 half bathroom residence offers generous living space and a unique blend of classic curb appeal with modern interior upgrades. The home features an open-concept layout designed for both everyday living and entertaining. The kitchen is designed for both function and style, showcasing a large island, stainless steel appliances, ample counter space, and a convenient corner pantry. It seamlessly connects to the dining and family areas, creating a welcoming and cohesive living space. Wood-look luxury vinyl plank flooring throughout main living areas on the first floor. Upstairs, you’ll find a spacious loft that can be used as a media room or flexible living area, along with a conveniently located laundry room and four bedrooms. The primary suite offers a well-designed en-suite bathroom and a walk-in closet, while the remaining bedrooms share a full bath. Ideally situated in the vibrant Winter Garden area, Highland Ridge residents enjoy access to a pool, playground, and half basketball court. The community is just minutes from the Hamlin shopping and dining district, with convenient access to major highways. Located less than 15 minutes from Walt Disney World, under 30 minutes from Universal Orlando and Downtown Orlando, and approximately 35 minutes from Orlando International Airport. Several renowned golf courses are also nearby. The property is located at the end of a quiet street with minimal traffic, this home offers exceptional privacy and tranquility, backing onto a natural preserve with no rear neighbors. Currently tenant occupied; tenants agree to vacate the property with a 30-day notice if requested by the buyer. Watch the attached professional video.
Listing is courtesy of: ELITE INTERNATIONAL REALTY INC (305-940-6611)
Listing Agent: Diller De Abreu Junior (786-818-0909)
13959 JOMATT LOOP, WINTER GARDEN, FL 34787
$774,90010 Days on yellowkey MLS ID: O6412718
0 Days Off yellowkey (back on 6/9/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2814 Built: 2016Monthly Fee: $75 Tax: $5,426 (2025)Community: Cypress ReserveSpa: YesSingle Family
Taxes:$5,426
Elementary School: SunRidge Elementary
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Stunning Conservation Home in Cypress Reserve – 225 Acres of Protected Nature Views! Welcome to 13959 Jomatt Loop, a beautifully maintained 4-bedroom, 3-bathroom home with 2,814 square feet of living space, ideally situated on one of the most desirable lots in Cypress Reserve, one of Winter Garden's premier communities. Set on a spacious 0.24-acre conservation homesite, this exceptional property enjoys breathtaking views of a 225-acre protected cypress preserve, creating a rare sense of privacy and tranquility that is increasingly difficult to find in today's market. Whether you're enjoying your morning coffee or relaxing at sunset, the peaceful natural backdrop provides a daily connection to Florida's beauty. From the moment you arrive, you'll appreciate the inviting covered front porch, attractive curb appeal, and spacious 3-car garage. Inside, the thoughtfully designed split floor plan offers the perfect balance of privacy and functionality for families and guests alike. At the heart of the home is a spacious kitchen featuring granite countertops, stainless steel appliances, and 42-inch solid wood cabinetry, with ample space for gathering and entertaining. The home is also equipped with natural gas service and a tankless water heater, providing both efficiency and convenience. The generously sized primary suite serves as a true retreat, featuring dual custom walk-in closets, dual vanities, a large glass-enclosed walk-in shower, and a separate garden tub perfect for unwinding after a long day. Step outside to enjoy Florida living at its finest. The home features a beautiful covered and screened rear patio that opens onto a massive paver deck complete with a hot tub, all overlooking the stunning conservation area beyond. A Lifestyle You'll Love: Cypress Reserve is one of Winter Garden's most sought-after communities, offering residents a beautiful community pool, playground, and remarkably low HOA fees of just $75 per month. One of the neighborhood's most desirable features is its proximity to Sunridge K-8 School, one of the area's highly rated schools, located just a short walk from the home. Prime Winter Garden Location: Located just minutes from the charm and energy of Historic Downtown Winter Garden, you'll enjoy easy access to the renowned Plant Street District, featuring award-winning restaurants, boutique shopping, live entertainment, breweries, and one of Central Florida's most popular weekly farmers markets. The future continues to look bright for this area with the nearby Tucker Ranch Recreational Park and Nature Preserve, a transformative 200-acre destination along Johns Lake. Residents will enjoy access to nature trails, playgrounds, picnic areas, canoe and kayak launches, open green spaces, and exciting future additions including boardwalks, fishing areas, and a sustainable teaching farm. Why Settle for Ordinary? Quality homes with this combination of conservation views, privacy, natural gas service, top-rated schools, and a prime Winter Garden location rarely become available. If you've been searching for a home that offers both everyday comfort and an exceptional lifestyle, this is an opportunity you won't want to miss. Schedule your private showing today before this incredible home is gone!
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Matthew Matin (321-948-5857)
16776 BROADWATER AVE, WINTER GARDEN, FL 34787
$1,299,90031 Days on yellowkey MLS ID: O6407043
REDUCED by $24,100 (1.8%) on 05/27/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3713 Built: 2018Monthly Fee: $383 Tax: $9,438 (2025)Community: Waterside/Johns Lk-Ph 1Spa: YesSingle Family
Taxes:$9,438
Remarks: Positioned on a premium homesite with an expansive manicured common area along one side, this property offers added privacy and open space, along with sweeping views of John’s Lake from the front of the home. Inside, the home opens to a formal dining area accented by wood beam ceilings, while custom wall details in the foyer and along the staircase add a refined, designer touch. The main living area features soaring ceilings, abundant natural light, wood beam ceiling accents, and a striking floor-to-ceiling accent wall, creating a dramatic yet inviting focal point that flows seamlessly into the dinette and open kitchen. Designed for both everyday living and entertaining, the kitchen includes a large island with seating, sleek cabinetry, stainless steel appliances, a gas cooktop, built-in oven, and generous pantry space. Just off the pantry, a connecting space between the kitchen and dining room offers the perfect opportunity for a coffee station or butler’s pantry. The main level also offers a spacious primary suite with a well-appointed bath and a custom walk-in closet featuring built-in drawers, cabinetry, and shelving, along with a secondary bedroom and full bath, ideal for guests or multigenerational living. Upstairs, you will find three additional bedrooms, including one with a private bath, while the remaining two share a full bath, plus a generous loft overlooking the living area that provides flexible space for a secondary living area, home office, or play space. The outdoor living space is designed for true Florida living, featuring a saltwater pool and spa added in 2021 with full automation, expansive Travertine tile decking, and a lanai with a motorized screen that extends your living space year-round. The patio is also pre-plumbed for a future outdoor kitchen, offering even more potential for entertaining. Additional highlights include a split three car garage configuration with a separate side entry one car bay and a 2 car garage equipped with an EV charging outlet. Waterside on John’s Landing offers a clubhouse, fitness center, resort-style pool, playground, covered dock, and pavilion on John’s Lake, all conveniently located near Horizon West, Hamlin, shopping, dining, and major roadways.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Alex Vastardis (407-947-6264)
14102 LOCHEND WAY, WINTER GARDEN, FL 34787
$978,80010 Days on yellowkey MLS ID: O6411646
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3606 Built: 2024Monthly Fee: $77 Tax: $11,605 (2025)Community: Westhaven At OvationSingle Family
Taxes:$11,605
Remarks: This beautifully maintained Toll Brothers Delray floor plan is 2 years new and sits on one of the community’s most desirable lots, directly overlooking the scenic community park. With excellent curb appeal, a covered front porch, and a long brick paver driveway, the home welcomes you from the moment you arrive. Step inside the dramatic two-story foyer and discover an open, light-filled floor plan with thoughtfully chosen upgrades, neutral colors, and high-end finishes throughout. The heart of the home is the expansive kitchen featuring a large prep island, built-in ovens, vented cooktop, walk-in pantry, and abundant cabinetry for all your storage needs. A convenient downstairs bedroom with a full bath offers ideal space for guests or multigenerational living. Upstairs, a spacious bonus room provides flexible living options, while the impressive primary suite steals the show with two walk-in closets, a luxurious garden bath, oversized shower, and dual vanities. Every bedroom is generously sized, giving family members their own private retreats. Just around the corner, the brand-new community clubhouse with its modern contemporary design is scheduled to open in July, bringing a state-of-the-art fitness center and sparkling community pool within easy walking distance. Perfectly located just minutes from Disney, major highways, top-rated shopping, and dining, this home is also zoned for highly sought-after K-12 schools. Why wait to build when you can move into this like-new Delray now and settle in before the new school year begins? A rare opportunity to own an upgraded Toll Brothers home in an unbeatable location.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Ronald Ziolkowski (407-592-7653)
617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,139,00093 Days on yellowkey MLS ID: O6389100
REDUCED by $11,000 (1.0%) on 06/01/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3624 Built: 2019Monthly Fee: $255 Tax: $16,181 (2025)Community: Canopy Oaks Ph 1Spa: NoSingle Family
Taxes:$16,181
Elementary School: Lake Whitney Elem
Remarks: One or more photo(s) has been virtually staged. One or more photos are virtually staged. Location. Luxury. Architectural character. Welcome to The Sanibel, affectionately known as “The Castle,” an award-winning home just minutes from the charm and energy of Historic Downtown Winter Garden. This stunning residence blends timeless Italian-inspired architecture with modern comforts, creating a home that feels both elegant and inviting. From the moment you arrive, the home makes a memorable first impression with its arched wood double doors, custom soffit lighting, and classic concrete tile roof. Step inside and you’re greeted by soaring ceilings, detailed beams, and crown molding that add warmth and sophistication to the open-concept living spaces—perfect for both everyday living and entertaining. The gourmet kitchen is designed to impress, featuring premium KitchenAid appliances, a natural gas cooktop, built-in refrigerator, 42” custom cabinetry, a hidden walk-in pantry, and a reverse osmosis water system. Whether hosting guests or enjoying a quiet night at home, this kitchen is the heart of it all. The first floor offers exceptional flexibility with a private office and a Junior Owner’s Suite—ideal for guests or multi-generational living. Upstairs, the primary suite becomes your personal retreat with a unique round spa-inspired bathroom, oversized walk-in closet, wet bar, and access to a private balcony. Two additional en-suite bedrooms, a loft, and an upstairs laundry room complete the second level. Step outside and enjoy multiple spaces designed for relaxing and entertaining, including Trex-decked balconies, a summer kitchen, and a peaceful fountain feature. Additional highlights include surround sound wiring, a whole-home generator, and thoughtful upgrades throughout the home. Beyond the property itself, the location truly sets this home apart. You’re just minutes from Downtown Winter Garden’s award-winning farmers market, vibrant restaurants, charming boutiques, scenic parks, and top-rated schools—with easy access to major highways for commuting throughout Central Florida. Recognized as Florida’s Best Model Home by the SEBC Excel Awards, The Sanibel offers a rare opportunity to own a home that combines architectural distinction, luxury features, and an unbeatable Winter Garden lifestyle. Note: One image includes a virtually added pool to illustrate potential backyard possibilities.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
729 MEADOW GLADE DR, WINTER GARDEN, FL 34787
$529,00030 Days on yellowkey MLS ID: O6407943
REDUCED by $1,000 (0.2%) on 06/06/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2070 Built: 2011Monthly Fee: $72 Tax: $3,138 (2025)Community: Covington Park A B D E F G & JSingle Family
Taxes:$3,138
Elementary School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Welcome to the highly sought after GOLF CART DISTRICT of downtown Winter Garden! Located in Covington Chase, this beautifully maintained home offers functionality, charm, and the unbeatable lifestyle that makes Winter Garden one of Central Florida’s most loved communities. Situated on a desirable corner lot, the curb appeal immediately stands out with mature landscaping, lush lawn space, and a welcoming exterior that makes a lasting first impression. Step inside and you will find a spacious open floor plan designed for both comfortable everyday living and entertaining guests. Natural light fills the home and creates a warm and inviting atmosphere throughout. The kitchen is truly the heart of the home featuring granite countertops, beautiful cherry cabinetry, closet pantry, breakfast bar seating, and plenty of prep space for cooking and hosting. The open concept layout allows full views into the family room so you never miss a moment while entertaining or spending time with family and friends. Sliding glass doors lead directly out to the screened lanai creating seamless indoor and outdoor living. The partially vinyl fenced backyard offers both privacy and flexibility with plenty of room to design the pool of your dreams, create an outdoor kitchen, garden space, or simply enjoy the Florida sunshine. Whether hosting weekend barbecues or relaxing after a long day, this outdoor space provides endless possibilities. The split bedroom floor plan offers privacy and convenience for everyone. The spacious secondary bedrooms are thoughtfully positioned with access to a guest bathroom that could easily function as a future pool bath. The primary suite offers a relaxing retreat with generous space and functionality. Inside laundry adds even more convenience to daily living. What truly makes this home special is the incredible Winter Garden lifestyle. Hop on your golf cart and head into historic downtown Winter Garden where you can spend your evenings enjoying local restaurants, boutique shopping, breweries, coffee shops, live entertainment, seasonal festivals, and community events year round. Cool off at the splash pad, bike or walk the scenic West Orange Trail, and experience the award-winning Winter Garden Farmers Market every Saturday morning which has become one of the most beloved attractions in Central Florida. Residents of Covington Chase also enjoy access to community amenities including a pool, playground, parks, and walking areas, all while being conveniently located near major highways, shopping, dining, and top rated schools. The location offers the perfect blend of peaceful neighborhood living with easy access to everything Winter Garden and Orlando have to offer. This is more than just a home. It is a lifestyle that so many are searching for and very few neighborhoods can truly offer. Come experience the charm, convenience, and golf cart lifestyle of downtown Winter Garden for yourself. Schedule your private showing today!
14378 BLACK LAKE PRESERVE ST, WINTER GARDEN, FL 34787
$764,9008 Days on yellowkey MLS ID: O6414181
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3167 Built: 2015Monthly Fee: $140 Tax: $6,855 (2025)Community: Black Lake PreserveSpa: NoSingle Family
Taxes:$6,855
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)
9849 LOST CREEK DR, WINTER GARDEN, FL 34787
$990,000569 Days on yellowkey MLS ID: O6258009
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3910 Built: 2021Monthly Fee: $250 Tax: $10,950 (2023)Community: WaterleighSpa: NoSingle Family
Taxes:$10,950
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. Big Price Reduction!!!!!! Nestled in the heart of Winter Garden’s prestigious Waterleigh community, this 5-bedroom, 4-bathroom masterpiece redefines modern luxury and family living. Boasting 3,910 sq. ft. of beautifully designed space, this 2021-built home is a perfect blend of timeless charm and contemporary convenience. From the moment you arrive, the immaculate landscaping and spacious 3-car garage set the stage for what lies within. Step onto the inviting front porch, and you’ll immediately feel at home. Inside, the gourmet kitchen takes center stage, showcasing gleaming white quartz countertops, custom 42-inch cabinets, and top-of-the-line stainless steel appliances. The oversized island is ready for anything—from morning coffee to lively dinner parties. Natural light floods the open living and dining spaces, where panoramic lake views create a serene backdrop for daily life. Retreat to the main-floor primary suite, a private haven with tranquil lake vistas, a spa-like ensuite, and a walk-in closet. Upstairs, a sprawling loft provides a perfect gathering space, while generously sized bedrooms ensure comfort for everyone. But the magic doesn’t stop indoors. Imagine unwinding on your covered patio as the sun sets, Disney’s iconic fireworks lighting up the sky above the lake. Beyond your doorstep, Waterleigh’s resort-style amenities await—scenic walking trails, sparkling pools, state-of-the-art fitness centers, and even a community garden. With its unbeatable combination of elegance, comfort, and convenience, this home offers more than just a place to live—it’s a lifestyle. Schedule your private tour today and start your next chapter in this extraordinary home!
Listing is courtesy of: REAL BROKER, LLC (407-279-0038)
Listing Agent: Jennifer Ibarra (213-500-7525)
8220 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$550,0009 Days on yellowkey MLS ID: O6412974
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2016Monthly Fee: $332 Tax: $8,597 (2025)Community: Waterleigh Ph 1BSingle Family
Taxes:$8,597
Remarks: One or more photo(s) has been virtually staged. Welcome home, to the highly sought-after Waterleigh community in Winter Garden! This spacious 4-bedroom, 3.5-bathroom Cleardon model offers 2,477 square feet of thoughtfully designed living space and is perfectly located just 10 minutes from Walt Disney World. Step inside to an open-concept floor plan ideal for entertaining, featuring a large granite kitchen island, modern NEW stainless-steel appliances, abundant cabinetry, and a walk-in pantry. The first floor includes a private bedroom and full bath, making it perfect for guests, multigenerational living, or a home office. Upstairs, you’ll find a versatile loft, convenient laundry room with NEW washer and dryer, two secondary bedrooms with a shared bath, and a spacious primary suite complete with dual vanities, a walk-in shower, separate water closet, linen storage, and a generous walk-in closet. Recent updates include a NEW HVAC system, NEW appliances, NEW carpet and fresh interior & exterior paint. Enjoy resort-style living with access to community pools, walking trails, dog parks, miniature golf, beach volleyball, fitness center, and a vibrant calendar of neighborhood events. The HOA covers lawn care, sprinkler maintenance, and mulch replacement, making homeownership even easier. Don’t miss this incredible opportunity to own in one of Winter Garden’s most desirable communities. Schedule a showing, today!
Listing is courtesy of: SERHANT (646-480-7665)
Listing Agent: Claire Fernando (850-737-1470)
279 DOE RUN DR, WINTER GARDEN, FL 34787
$599,00015 Days on yellowkey MLS ID: TB8513595
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2435 Built: 2005Monthly Fee: $57 Tax: $2,489 (2025)Community: Deerfield Place 57/1Single Family
Taxes:$2,489
Remarks: One or more photo(s) has been virtually staged. Discover your dream home in the heart of vibrant Winter Garden! This charming 3/2.5 with spacious loft offers modern upgrades galore—brand-new roof & carpet (2026), stunning 2025 kitchen remodel, fresh downstairs flooring, new water heater, epoxy garage with ceiling-mounted storage rack, elegant crown molding, 6” baseboards, wooden trim/chairail moldings, wainscoting picture frames, widened driveway, new exterior paint, and huge walk-in master closet. Enjoy a fully fenced backyard oasis with expansive 24x24 pavers on a generous 6,048 sq ft lot (Flood Zone X). Low HOA in this neighborhood. Minutes to downtown, shops, dining & highways—your perfect Central Florida lifestyle awaits! Some photos are virtually staged.
Listing is courtesy of: FLORIDA EXECUTIVE REALTY 2 (813-832-5400)
Listing Agent: Jerry Cionci (941-779-4717)
708 ORANGE BELT LOOP, WINTER GARDEN, FL 34787
$745,00033 Days on yellowkey MLS ID: G5112211
3 Days Off yellowkey (back on 6/9/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1916 Built: 2019Monthly Fee: $280 Tax: $8,412 (2025)Community: Heritage/Plant StreetSingle Family
Taxes:$8,412
Remarks: LOCATED IN THE HIGHLY SOUGHT AFTER GOLF CART DISTRICT OF DOWNTOWN WINTER GARDEN!!! This beautifully maintained and move-in ready, this immaculate 3-bedroom, 2-bath home offers comfort, style, and convenience in one exceptional package. Featuring all tile flooring throughout with no carpet, stunning plantation shutters, the open and spacious floor plan seamlessly connects the kitchen, dining, and family room areas-perfect for both everyday living and entertaining. The oversized primary suite includes a cozy sitting area, while the en-suite bath features dual sinks, a relaxing garden tub, and a walk-in shower. A desirable split-bedroom layout provides privacy, with two additional bedrooms and a full bath located on the opposite side of the home. The chef's kitchen is fully equipped with stainless steel appliances, 42-inch cabinetry, a built-in DOUBLE oven and microwave, gas cooktop, and an extra-large pantry. The inside laundry room offers added convenience with shelving, storage cabinets, and utility sink. The garage also includes overhead storage for additional organization. Step outside to extended screened porch, offering plenty of room to relax and enjoy the peaceful pond view with no immediate rear neighbors. A dog park is an added community perk and adds even more convenience for pet lovers. Located just blocks from downtown Winter Garden, you'll enjoy easy access to holiday events, local restaurants, charming shops, the award-winning farmers market, and the popular golf cart district. This is a home you do NOT want to miss!!! Schedule your private tour today.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Kristi Lowery (407-235-4920)
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