Location: Winter Garden
Do Not Show Listings
5024 PALMETTO PARK DR, WINTER GARDEN, FL 34787
$805,00050 Days on yellowkey MLS ID: O6414749
REDUCED by $14,000 (1.7%) on 07/20/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3061 Built: 2017Monthly Fee: $187 Tax: $10,816 (2025)Community: Orchard Hills Ph 3Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,816
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to this beautifully upgraded home in the heart of Winter Garden. Featuring luxury vinyl flooring throughout with no carpet, this home offers a clean, modern feel and a functional layout designed for everyday living and entertaining. The main living area showcases custom millwork and built-in details, while the elegant powder room adds a touch of sophistication. With over $150,000 in improvements, this home showcases a level of quality rarely found at this price point. Designed and improved by an owner who planned to live in the home long-term, no expense was spared in creating a space that is both beautiful and highly functional. The gourmet kitchen serves as the heart of the home, offering ample space for cooking and gathering. Step outside to a fully equipped outdoor living area featuring a complete summer kitchen with sink, cooktop, refrigerator, built-in grill, and a traditional parrilla grill. With no rear neighbors, the backyard provides added privacy and the perfect setting for relaxing or entertaining guests. Additional improvements include a whole-home water softener system and numerous thoughtful enhancements throughout the property. Located just steps from the community clubhouse, residents enjoy access to resort-style amenities including a swimming pool, fitness center, social hall with event kitchen, playground, sports courts, walking and biking trails, dog park, community green spaces, and parks. Conveniently located near shopping, dining, and major roadways, and zoned for highly rated A-rated schools, this home offers an exceptional opportunity to enjoy the best of Winter Garden living. PROPERTY FEATURES LEASED SOLAR PANELS. THE SOLAR LEASE MUST BE ASSUMED BY THE NEW BUYER PRIOR TO CLOSING. THE CURRENT OWNER’S MONTHLY SOLAR PAYMENT IS $145, PROVIDING SOLAR ENERGY THAT HELPS OFFSET ELECTRICITY USAGE AND REDUCE TRADITIONAL UTILITY COSTS.
Listing is courtesy of: PRISTINE INTERNATIONAL REALTY LLC (407-286-3846)
Listing Agent: Bruna Canesin Motta (407-580-1367)
8768 SONOMA COAST DR, WINTER GARDEN, FL 34787
$890,00052 Days on yellowkey MLS ID: O6414519
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3416 Built: 2022Monthly Fee: $275 Tax: $11,513 (2024)Community: WaterleighSpa: NoSingle Family
Taxes:$11,513
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2024
Middle School: Water Spring Middle
Remarks: UNBEATABLE OPPORTUNITY IN WATERLEIGH! This stunning move-in ready home offers the perfect combination of luxury, privacy, and Florida lifestyle. Enjoy a premium lot, spacious open floor plan, designer finishes, and access to resort-style amenities including pools, fitness center, walking trails, and parks. Ideally located near top-rated schools, shopping, dining, major highways, and Disney. Homes like this at this value don't last! Priced to sell and ready for a quick closing—schedule your private showing today before this incredible opportunity is gone!
Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)
Listing Agent: Martha Leighton, Pa (407-223-7767)
12241 ENCORE AT OVATION WAY, WINTER GARDEN, FL 34787
$1,190,00085 Days on yellowkey MLS ID: O6403198
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3693 Built: 2021Monthly Fee: $225 Tax: $12,882 (2025)Community: Encore/Ovation Ph 1Single Family
Taxes:$12,882
Remarks: Welcome to this stunning 2021-built residence in the highly sought-after Encore at Ovation community in Winter Garden, where modern elegance meets exceptional comfort and thoughtful design. This beautifully upgraded home showcases an open-concept floor plan filled with abundant natural light, soaring ceilings, and exquisite, professionally curated finishes throughout. rom the moment you arrive, you’re greeted by impressive curb appeal, lush landscaping, a charming front porch, and a grand, custom-designed entry hall that sets the tone for the home’s refined interior. Inside, you’ll find designer lighting, including high-end chandeliers and custom pendant fixtures, enhancing both the common and private living spaces. The gourmet kitchen is a true showstopper, featuring next-generation stainless steel appliances, premium cabinetry, stunning stone countertops, a spacious center island, and a large walk-in pantry, perfectly designed for both everyday living and entertaining. The seamless flow into the living and dining areas creates an inviting atmosphere for gatherings of any size. Retreat to the expansive primary suite, where the spa-inspired master bathroom offers a truly luxurious experience with oversized proportions and high-end finishes, complemented by custom-designed closets. Additional bedrooms are generously sized, offering flexibility for guests, a home office, or multi-generational living. This home also features a spacious loft, an oversized laundry room, and beautiful flooring throughout with no carpet, providing both style and easy maintenance. Step outside to your private backyard oasis, designed for unforgettable moments. Enjoy a covered summer kitchen complete with modern features and a cozy fireplace, perfect for barbecues and al fresco dining. The breathtaking pool and spa, enhanced by elegant landscaping and design, create a resort-style ambiance. A fire pit gathering area and outdoor shower complete this exceptional space, your guests may never want to leave. Additional highlights include a Tesla charger, solar panel system for significant energy savings, and a garage equipped with storage racks and ample space. Situated on a premium lot, this home truly offers it all. Ideally located near top-rated schools, shopping, dining, and major highways, and just minutes from Walt Disney World and Orlando’s world-class attractions, this move-in-ready masterpiece delivers the perfect combination of luxury, efficiency, and prime location.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Any Alves (407-455-0618)
1698 JUNIPER HAMMOCK ST, WINTER GARDEN, FL 34787
$1,399,000102 Days on yellowkey MLS ID: V4948569
REDUCED by $51,000 (3.5%) on 06/06/2026
Bed: 7 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4700 Built: 2019Monthly Fee: $97 Tax: $9,199 (2025)Community: Mcallister LndgSingle Family
Taxes:$9,199
Remarks: Welcome to an extraordinary Winter Garden retreat where luxury, flexibility, and resort-style living come together in one remarkable residence. Situated on a premium corner lot, this expansive 7-bedroom, 4-bath home offers over-the-top living spaces designed for entertaining, multi-generational living, and creating unforgettable memories. Step inside to soaring ceilings, abundant natural light, and an open-concept floor plan that effortlessly blends elegance with everyday comfort. The chef-inspired kitchen serves as the heart of the home, featuring an oversized island, breakfast bar, abundant cabinetry, and seamless flow into the spacious family room and café dining area. The thoughtfully designed layout includes both the owner's suite and a guest bedroom on the main level, providing ideal accommodations for extended family or visitors. Upstairs, a sprawling game room, dedicated home theater, and additional bedrooms create the ultimate entertainment hub for family and guests alike. Outside, your private backyard oasis awaits. Relax by the sparkling in-ground pool, entertain under the covered lanai, or host gatherings in the fully equipped summer kitchen. The fully fenced yard provides privacy while maximizing enjoyment of Florida's year-round sunshine. Perfectly positioned just minutes from Historic Downtown Winter Garden, Orlando's world-famous attractions, premier dining, shopping, and entertainment, this exceptional home offers the lifestyle today's buyers are seeking—space to gather, room to grow, and amenities that make every day feel like a vacation.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-862-9966)
Listing Agent: Nell Adams (386-315-3967)
14301 WHITE MOSS WAY, WINTER GARDEN, FL 34787
$949,99929 Days on yellowkey MLS ID: G5114391
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4053 Built: 2015Monthly Fee: $190 Tax: $9,701 (2026)Community: Orchard HillsSpa: NoSingle Family
Taxes:$9,701
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2026
Middle School: Bridgewater Middle
Remarks: Virtually Staged. Beautifully maintained 5-bedroom, 3.5-bath home with over 4,000 square feet in the highly sought-after Orchard Hills community. Situated on a spacious corner lot, this home offers an ideal floor plan with the primary suite on the first floor and expansive living spaces designed for both everyday living and entertaining. The gourmet kitchen features stainless steel appliances, double wall ovens, an oversized center island, abundant cabinetry, a butler’s pantry, and a large walk-in pantry, all overlooking the open family room and screened lanai. This home is loaded with valuable upgrades, including a SOLAR energy system that helps keep electric costs exceptionally low, with most monthly electric bills averaging around just $33. Additional improvements include a HYBRID energy-efficient water heater, a Pelican whole-house WATER FILTRATION system, and CUSTOM his-and-hers walk-in closets in the primary suite. There is NO CARPET throughout the home, with luxury vinyl plank flooring covering the entire second floor for a modern, low-maintenance finish. The spacious first-floor primary suite offers a private retreat with dual custom walk-in closets and an elegant en-suite bath featuring dual vanities, a makeup station, an oversized walk-in shower, and a soaking tub. Upstairs, you’ll find four additional bedrooms, two full bathrooms, a large loft, and a separate bonus/media room, providing flexible space for family, guests, or working from home. The back yard is fully fenced and plenty of room for a pool. Residents of Orchard Hills enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, dog park, and walking trails with the pool and clubhouse being a couple of minutes walk. The home is zoned for highly rated schools and is conveniently located just minutes from Walt Disney World, the rapidly growing Hamlin Town Center, shopping, dining, and entertainment. With easy access to SR 429, the Florida Turnpike, and SR 408, commuting is simple, and Orlando International Airport is within easy reach. Combining energy efficiency, extensive upgrades, generous living space, and an exceptional location, this home is truly move-in ready.
Listing is courtesy of: FLORIDA PLUS REALTY, LLC (352-901-9100)
Listing Agent: Claire Brooks (407-967-5829)
16149 WIND VIEW LN, WINTER GARDEN, FL 34787
$495,000137 Days on yellowkey MLS ID: O6389892
REDUCED by $3,000 (0.6%) on 05/30/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2036 Built: 2016Monthly Fee: $332 Tax: $4,472 (2025)Community: Waterleigh Ph 1BSingle Family
Taxes:$4,472
Elementary School: Panther Lake Elementary
Remarks: Welcome home to one of the most popular DR Horton floor plans- the Cordale! With a first floor primary suite, spacious open floor plan downstairs, and additional living space upstairs, it is easy to see how the functionality of this home will make it a great fit for you. This home has had 1 owner who has meticulously cared for the home as will be evident immediately upon entering. The open concept living space greets you with the kitchen, dining space, and living room. Lined with windows and recessed lighting, this space feels bright and welcoming. Stainless steel appliances, granite countertops, and ample counterspace equip the kitchen. The downstairs laundry room is tucked away in the front of the home to keep tending to that chore quiet. The primary suite is nestled in the back of the home for privacy and features and en suite bathroom. A walk-in shower, dual vanity, and walk-in closet make this room fit for luxury and comfort. An elongated drop zone leads you to the 2-car garage and has granite countertops and cabinetry in the same colors as in the kitchen for continuity of the downstairs space. The remaining 2 bedrooms are located upstairs where a loft also provides these rooms with another living space. They also share a bathroom with a shower/bathtub combination. The fun continues out back where you'll find a covered brick-paved patio. Relish in the view of not having any rear neighbors, admire the rarity of having a corner lot, and indulge in the unique green space view out of the front of the home. The Waterleigh community is known for its vast array of resort-style amenities include community pools, playgrounds, fitness centers, sports courts, walking trails, dog parks, and more! Primely located in Horizon West, this home is ready for its new owners to make memories here for years to come. Inquire today to make this gem your own! ***NEW HVAC INDOOR BLOWER UNIT, NEW HVAC OUTDOOR CAPACITOR UNIT***
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Jacquelyn Voigt (941-356-3956)
16038 JOHNS LAKE OVERLOOK DR, WINTER GARDEN, FL 34787
$2,125,0006 Days on yellowkey MLS ID: O6426648
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4139 Built: 2015Monthly Fee: $235 Tax: $23,164 (2025)Community: Hickory HammockSpa: YesSingle Family
Taxes:$23,164
Elementary School: Whispering Oak Elem
High School: West Orange High
Middle School: Hamlin Middle
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)
16004 OLLIVETT ST, WINTER GARDEN, FL 34787
$834,99931 Days on yellowkey MLS ID: S5152585
INCREASED by $5,000 (0.6%) on 06/29/2026
Bed: 7 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4704 Built: 2014Monthly Fee: $110 Tax: $9,493 (2024)Community: Verde Park Ph 1Single Family
Taxes:$9,493
Elementary School: Grassy Lake Elementary
High School: Lake Minneola High
Middle School: East Ridge Middle
Remarks: Welcome to 16004 Ollivet, an exceptional residence where thoughtful design, high-end upgrades, and everyday functionality come together in one of Winter Garden's most desirable communities. Meticulously maintained and beautifully appointed, this move-in-ready home offers the perfect balance of elegant living, modern convenience, and timeless style. From the moment you enter, you'll appreciate the bright, open floor plan, soaring ceilings, and abundance of natural light that create an inviting and spacious atmosphere. Designed for both entertaining and everyday living, the expansive main living area flows seamlessly into the dining space and gourmet kitchen, making it easy to host family gatherings or enjoy quiet evenings at home. The chef-inspired kitchen is the heart of the home, featuring abundant cabinetry, generous countertop space, a large center island, quality appliances, and ample storage. Whether you're preparing a weeknight dinner or entertaining guests, this space offers both beauty and functionality. The spacious primary suite serves as a private retreat, offering a relaxing escape at the end of the day. One of its standout features is the professionally designed custom walk-in closet, providing exceptional organization, premium built-ins, and a luxurious boutique-style feel. The en-suite bathroom complements the space with modern finishes. A versatile flex room adds even more value to the home and has been enhanced with custom built-in cabinetry, making it an ideal home office, executive workspace, library, study, craft room, or media room. The custom storage solutions maximize functionality while adding a design element that sets this home apart. The additional bedrooms are generously sized and thoughtfully positioned to provide comfort and privacy for family members or guests. Every room reflects the pride of ownership found throughout the home. One of the rare features you'll appreciate is the three-car garage, offering plenty of room for multiple vehicles, golf carts, recreational equipment, a workshop, fitness area, or additional storage. Step outside to the covered lanai, where you can enjoy your morning coffee, unwind after a long day, or entertain family and friends while overlooking the backyard. The outdoor living space provides the perfect extension of the home's interior. Conveniently located near Historic Downtown Winter Garden, Horizon West, shopping, dining, entertainment, parks, walking trails, major highways, and Central Florida's world-famous attractions, this home offers both convenience and an exceptional lifestyle. With its designer upgrades, custom built-in features, spacious open floor plan, rare three-car garage, and outstanding location, this home truly stands out. Every detail has been thoughtfully curated to create a residence that is as functional as it is beautiful. Schedule your private showing today and experience everything this remarkable property has.
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)
Listing Agent: Rafael Ortiz Pena (407-371-8773)
15139 CANOPY COVER DR, WINTER GARDEN, FL 34787
$699,00043 Days on yellowkey MLS ID: O6415871
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2000 Built: 2023Monthly Fee: $642 Tax: $5,682 (2025)Community: Del Webb OasisSingle Family
Taxes:$5,682
Remarks: Welcome to this ELEGANTLY UPGRADED and nearly new 2-bedroom, 2-bath residence in the highly sought-after Del Webb Oasis of Winter Garden, a GUARD-GATED 55+ community where resort-style living meets everyday sophistication. Perfectly situated on one of ONLY TWO PREMIUM HOMESITES of its kind within the community, this exceptional property enjoys a truly rare distinction: an EXCLUSIVE SIDE EASEMENT that creates exceptional privacy, expanded green space, and a level of openness rarely found in community living, with no immediate neighbor on one side and convenient proximity to the clubhouse area. From the moment you arrive, the home impresses with its REFINED CURB APPEAL, lush landscaping, and a spacious 2-car garage enhanced with CUSTOM STORAGE SOLUTIONS. Inside, a bright OPEN-CONCEPT LAYOUT welcomes you with abundant natural light and meticulous attention to detail throughout every space. The Kitchen is a TRUE SHOWPIECE, equipped with premium stainless steel appliances, a GAS COOKTOP, BUILT-IN OVEN, a CUSTOM BUILT-IN PANTRY WITH PULL-OUT DRAWERS, generous cabinetry, and stone countertops, all seamlessly flowing into the living and dining areas. The Living Room has been elevated with an INTEGRATED SURROUND SOUND SYSTEM, creating the perfect setting for daily enjoyment and entertaining. The Primary Suite is a private retreat featuring a CUSTOM-DESIGNED WALK-IN CLOSET SYSTEM and a well-appointed en-suite bath with dual vanities, generous storage, and a walk-in shower. An additional SECONDARY BEDROOM provides comfortable accommodations for family or guests, while the DEDICATED DEN, enhanced with UPGRADED HIGH BASEBOARDS and RECESSED LIGHTING, offers the flexibility of a home office, hobby room, or formal sitting area. CUSTOM CLOSET SYSTEMS throughout ensure every space is as functional as it is beautiful. Step outside to where this property truly STANDS APART. The expansive SCREENED-IN LANAI opens to an EXTENDED OUTDOOR DECK and a fully appointed BUILT-IN OUTDOOR KITCHEN (BBQ Area), all framed by CUSTOM OUTDOOR LIGHTING, creating an exceptional outdoor retreat designed for year-round Florida living. Additional highlights include a WHOLE-HOME WATER FILTRATION AND SOFTENER SYSTEM, FRESH INTERIOR PAINT throughout, and additional RECESSED LIGHTING both inside and outside that elevates the home's ambiance day and night. Residents of Del Webb Oasis enjoy RESORT-STYLE AMENITIES, including a 12,000 SF clubhouse with coffee bar, lounge, and wine lockers, a sparkling pool, state-of-the-art fitness center, tennis courts, and a vibrant social calendar, along with included cable and internet, fostering the active and connected lifestyle that Del Webb is famous for. IDEALLY LOCATED in Winter Garden, you are just minutes from the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for boutique shops, dining, and a weekly farmers market. Enjoy outdoor recreation along the WEST ORANGE TRAIL, or take a short drive to WORLD-CLASS ATTRACTIONS including Walt Disney World Resort and Universal Studios. Convenient access to FL-429 and major roadways makes it easy to enjoy the very best of Central Florida. This exceptional residence offers a RARE OPPORTUNITY to enjoy elevated, low-maintenance living on one of the community's most coveted homesites, where every upgrade has been thoughtfully chosen and every detail meticulously executed. Homes of this caliber and setting are a TRUE RARITY in Del Webb Oasis. Now is the time, don't miss your chance to call this home.
Listing is courtesy of: INTERNATIONAL TEAM INC (321-388-1372)
Listing Agent: Jo Costa (321-388-1372)
15143 BLUE PEACOCK LN, WINTER GARDEN, FL 34787
$589,00050 Days on yellowkey MLS ID: O6414996
REDUCED by $6,000 (1.0%) on 07/16/2026
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)
217 W BAY ST, WINTER GARDEN, FL 34787
$1,349,00080 Days on yellowkey MLS ID: S5149527
REDUCED by $46,000 (3.3%) on 07/21/2026
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2800 Built: 2025 Tax: $5,958 (2025)Community: Cooper & Sewell AddSingle Family
Taxes:$5,958
Remarks: Stunning family home with an option to purchase the fully renovated 3 bed, 2 bath home next door - perfect for inlaws home, investment property, or just extra family space (call agent for details)!! Experience the best of Historic Winter Garden living in this brand-new Craftsman-style home, ideally located just steps from downtown dining, shopping, entertainment, and the renowned West Orange Trail. Originally a charming 1950s bungalow, the 576 sq. ft. home has been completely renovated and thoughtfully expanded into a stunning 2,800 sq. ft. residence offering 5 bedrooms, 4 bathrooms, and exceptional modern upgrades throughout. Relax on the inviting front porch and enjoy the charm and atmosphere of this idyllic golf cart community. Inside, a bright and spacious open floor plan welcomes you with designer finishes, 10-foot ceilings, luxury waterproof vinyl plank flooring, plantation shutters, 8-foot doors, and elegant architectural details throughout. The heart of the home is the spectacular chef’s kitchen featuring premium LG stainless steel appliances, built-in oven and microwave, induction cooktop, wine fridge, oversized island with seating and storage, 42” refrigerator, and an enormous walk-in pantry complete with an additional retro-style refrigerator. The adjoining family room showcases a custom fireplace with built-in storage and two sets of French doors opening to a large covered lanai with summer kitchen, overlooking the beautifully landscaped and fully fenced backyard with additional deck space for entertaining and relaxing. The luxurious primary suite offers custom walk-in closets, a spa-inspired en-suite bath, and private French doors leading to a secluded patio and deck area. A separate lower-level wing includes two additional bedrooms, a full bath, and utility room, creating endless possibilities for an in-law suite, home office, theater room, or private guest retreat. Upstairs, you’ll find two spacious bedrooms, including one with en-suite bath, an additional full bath, linen storage, and generous extra storage space. Additional highlights include a covered carport with EV charging outlet, oversized driveway with parking for at least 6 cars, 2-zone A/C system, gutters with leaf guards, upgraded lighting, charming picket fencing, lush landscaping, and a 10x8 storage/workshop. Live the coveted Winter Garden lifestyle with golf cart access to charming boutiques, restaurants, breweries, parks, the weekly farmers market, Lake Apopka, splash pad, and more. This exceptional home perfectly combines historic charm with luxurious modern living in one of Central Florida’s most sought-after communities. Don’t miss this rare opportunity!
Listing is courtesy of: WATSON REALTY CORP. (407-589-1600)
Listing Agent: Sue Webb (407-361-6425)
9218 HOLLISTON CREEK PL, WINTER GARDEN, FL 34787
$890,000150 Days on yellowkey MLS ID: O6386394
REDUCED by $9,000 (1.0%) on 07/16/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3087 Built: 2018Monthly Fee: $164 Tax: $11,801 (2025)Community: Watermark Ph 2BSpa: NoSingle Family
Taxes:$11,801
Remarks: Delight your clients with this unique opportunity in Watermark, one of the most desirable communities in Winter Garden. This elegant two-story residence combines sophistication, comfort, and impeccable finishes in every detail, featuring over $150,000 in upgrades that elevate the home’s overall quality and value. It offers 4 bedrooms, 3 full bathrooms, and 1 powder room, along with a simply enchanting outdoor area designed to provide unforgettable moments. Upon entering, a spacious and welcoming foyer leads to open-concept living areas, where the living room and dining room connect harmoniously, creating a bright and airy space ideal for entertaining family and friends. The beautiful porcelain tile floors enhance the elegance of the property. The kitchen is a true highlight, equipped with appliances, high-quality wood cabinetry, and ample countertop space, combining functionality and style for everyday living. On the second floor, all bedrooms provide greater privacy and comfort. The bedrooms feature closets and carpeting, creating a cozy atmosphere. The primary suite is a special retreat, featuring two walk-in closets and a spacious bathroom with dual sinks, offering both practicality and sophistication. The laundry room is also located on the upper floor and includes a sink, washer, and dryer, providing added convenience to the family’s routine. Outside, the property impresses with a fully equipped summer kitchen featuring a built-in grill, granite countertops, cabinetry, and a sink — perfect for gatherings and family moments — integrated with a private heated pool, allowing year-round enjoyment with comfort and exclusivity. Living in Watermark means enjoying resort-style amenities, including a community pool, modern fitness center, tennis court, playground, green areas, and tree-lined sidewalks for outdoor walks. The location is another major advantage: just minutes from Hamlin Town Center, with excellent restaurants, cafés, movie theater, and supermarkets; easy access to Walt Disney World Resort; and close to Florida State Road 429, providing convenient access to Orlando and the entire region. Additionally, it is surrounded by highly rated schools and all the conveniences that Winter Garden offers. A complete home, offering leisure, comfort, and a prime location. Don’t miss the opportunity to live or invest in one of the best addresses in the region.
Listing Agent: Gustavo Carneiro (407-758-4001)
13856 GLYNSHEL DR, WINTER GARDEN, FL 34787
$850,00043 Days on yellowkey MLS ID: O6416757
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3538 Built: 2003Monthly Fee: $167 Tax: $11,261 (2025)Community: GlynwoodSpa: YesSingle Family
Taxes:$11,261
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
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)
2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787
$589,0004 Days on yellowkey MLS ID: O6428109
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2048 Built: 2000Monthly Fee: $109 Tax: $4,516 (2025)Community: Wintermere PointeSpa: YesSingle Family
Taxes:$4,516
Elementary School: Wheatley Elem
Remarks: Virtually Staged. Welcome to Wintermere—where comfort, privacy, and location come together in one exceptional home. Nestled on a quiet cul-de-sac within the desirable gated Wintermere community, this beautifully maintained 4-bedroom, 2-bath residence offers an ideal blend of indoor and outdoor Florida living. The open split-bedroom floor plan is filled with natural light and features soaring ceilings, spacious living areas, and an updated kitchen complete with a large center island, stainless steel appliances, generous cabinetry, and abundant counter space overlooking the main living area—perfect for everyday living and entertaining. The private primary suite offers a relaxing retreat with dual vanities, a spacious walk-in closet, a garden tub, and a separate shower. Step outside to your own backyard oasis featuring a saltwater pool, expansive lanai, and oversized fenced backyard situated on a generous 0.31-acre lot. Whether you’re hosting family gatherings, enjoying quiet evenings by the pool, or simply taking advantage of Florida’s year-round sunshine, this outdoor space was designed to be enjoyed. Additional highlights include an indoor laundry room, two-car garage, extended driveway, mature landscaping, and the security of a gated neighborhood with sidewalks throughout. Ideally located just minutes from Winter Garden Village, Hamlin Town Center, Walt Disney World, SR-429, Florida’s Turnpike, shopping, dining, hospitals, major employers, and highly regarded schools, this home offers exceptional convenience while maintaining a peaceful residential setting. If you’ve been searching for a move-in ready pool home in one of Winter Garden’s most sought-after gated communities, this property is one you won’t want to miss. Saltwater pool! Screened lanai! Cul-de-sac! Gated community Split floor plan Open concept! Stainless steel appliances! Center island! Fenced backyard! No rear neighbors! Move-in ready! Winter Garden Close to Disney Near Winter Garden Village Near Hamlin Easy access to SR-429 & Florida’s Turnpike Ask about the Incentives that you may QUALIFY FOR!!!
Listing is courtesy of: LANDLORD FINDERS BUILD REAL ESTATE LLC (407-697-4311)
Listing Agent: Heather Grooms (407-697-4311)
16802 OAKBORO ST, WINTER GARDEN, FL 34787
$500,0007 Days on yellowkey MLS ID: O6425489
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1705 Built: 2020Monthly Fee: $257 Tax: $7,269 (2025)Community: Waterleigh Ph 3B 3C & 3DSpa: NoSingle Family
Taxes:$7,269
Remarks: Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Rick Brown (407-393-5901)
2010 BOSS HEWETT ST, WINTER GARDEN, FL 34787
$1,500,00020 Days on yellowkey MLS ID: O6423216
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3781 Built: 2022Monthly Fee: $165 Tax: $11,186 (2025)Community: Hull Island/Oakland Ph 2Single Family
Taxes:$11,186
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
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)
8506 BAYVIEW CROSSING DR, WINTER GARDEN, FL 34787
$1,299,00028 Days on yellowkey MLS ID: O6421255
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3966 Built: 2016Monthly Fee: $380 Tax: $11,330 (2025)Community: Waterleigh Ph 1ASpa: YesSingle Family
Taxes:$11,330
Remarks: LAKEFRONT living with TWO PRIMARY SUITES, this one has it all. Tucked into the highly desirable Phase 1 of Waterleigh, this Emerald Homes former model sits right on HICKORYNUT LAKE with unobstructed water views, plus two of the three secondary bedrooms enjoy DISNEY FIREWORKS VIEWS every night. Featuring 5 bedrooms, 5 bathrooms, a tile roof, and an oversized 3 car garage. Inside you'll find wood look tile floors, a flex space perfect for an office or playroom, and a formal dining room. The kitchen features quartz countertops and stainless steel appliances. The casual dining nook overlooks the lake, making every morning coffee feel like a getaway. The first primary suite sits on the main level near the pool bath, with a walk-in closet, soaking tub, and dual sinks with quartz counters, ideal for guests or multigenerational living. Upstairs, the second primary suite steals the show with an elevated lake view, an oversized walk-in closet, and a spa-style bath with dual vanities and a separate water closet. A spacious loft offers an additional living space or game room. Outside, the pool deck sets the stage for sunset evenings by the pool and hot tub overlooking the lake. Waterleigh's HOA takes care of your landscaping and lawn maintenance, and the community offers a resort-style clubhouse pool, mini golf, beach volleyball, walking trails, and a dog park nearby, all just minutes from the 429 and Disney. Schedule your private tour today.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
1642 CHANDELLE LN, WINTER GARDEN, FL 34787
$689,90027 Days on yellowkey MLS ID: G5114093
REDUCED by $20,000 (2.8%) on 07/20/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2918 Built: 2006Monthly Fee: $167 Tax: $8,474 (2025)Community: Belle Meade-Ph I B D & GSpa: NoSingle Family
Taxes:$8,474
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)
17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$620,00029 Days on yellowkey MLS ID: G5114379
REDUCED by $10,000 (1.6%) on 07/05/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2692 Built: 2017Monthly Fee: $215Community: Waterside/Johns Lake Ph 2ASingle Family
Taxes:$0
Elementary School: Hamlin Elementary
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)
132 ZACHARY WADE ST, WINTER GARDEN, FL 34787
$515,00032 Days on yellowkey MLS ID: O6411394
REDUCED by $10,000 (1.9%) on 07/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1708 Built: 2002Monthly Fee: $67 Tax: $3,813 (2025)Community: Lakeview Reserve 46/149Spa: NoSingle Family
Taxes:$3,813
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)
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