Location: Winter Garden , 34787
Do Not Show Listings
9354 LAKE HICKORY NUT DR, WINTER GARDEN, FL 34787
$999,99972 Days on yellowkey MLS ID: O6385808
REDUCED by $49,001 (4.7%) on 05/06/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2278 Built: 1983 Tax: $3,375 (2025)Community: Hickory Lake EstatesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,375
Elementary School: Panther Lake Elementary
High School: None
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: Rare find on a tucked away street in the heart of it all. This lakefront home on Lake Hickory Nut, a 403-acre skiable and bass fishing lake in Winter Garden, offers approximately 100 feet of direct waterfront with no HOA and Disney Firework Views. Situated on an oversized lot with the ability to park boats or RVs, the property is set within a peaceful community surrounded by mature landscaping and spacious homesites. Enjoy breathtaking sunrise views over Lake Hickory Nut, with expansive water views visible throughout the house and on your private balcony. The lake is routinely tested by Orange County and is recognized as a high-quality lake in the area, offering exceptional water clarity and cleanliness providing year-round recreational enjoyment. The home is completely upgraded and renovated. Featuring new lighting, flooring, windows, doors, AC, well, plumbing, interior/exterior paint, epoxy garage flooring, kitchen, bathrooms, appliances, garage door, soffits, gutters, and a paver driveway, walkway, and patio. The living areas of this home bask in natural light, making it feel airy and bright. A wood-burning fireplace in the living room and oversized windows overlooking the lake create a warm and inviting space. The kitchen features an eat-in area that flows into a formal dining room and formal living room, providing flexibility for both entertaining and everyday living. A Florida room is lined with oversized windows and trim detail that maximize natural light and panoramic water views, with French doors leading to a paver patio along the shoreline. The private dock, built in 2018, includes covered and open seating areas ideal for relaxing, boating, or fishing. The first floor includes a bedroom with en-suite bath. Upstairs, double doors lead to an oversized primary suite with a private balcony overlooking the lake. The primary bath offers dual separate sinks and a spacious closet. A secondary upstairs bedroom features a window seat, and an additional full bathroom serves the second level. The upstairs is also prepped for a stackable laundry unit (in addition to the garage hookup) for added convenience. Ideally located near Horizon West, Hamlin Town Center, Downtown Winter Garden, and Orange County National Golf Center, this property offers a rare opportunity to own fully updated, skiable lakefront frontage in one of Central Florida’s most desirable locations.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Matt Kester (772-494-8550)
10031 MEMOIR AVE, WINTER GARDEN, FL 34787
$400,00026 Days on yellowkey MLS ID: O6399210
REDUCED by $15,000 (3.6%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1636 Built: 2018Monthly Fee: $268 Tax: $5,910 (2025)Community: Storey Grove Ph 1B-1Townhouse
Taxes:$5,910
Elementary School: Water Spring Elementary
High School: Horizon High School
Remarks: PRICE TO SELL!!! This gorgeous and spacious Townhome will impress you! Absolutely nothing left to do in this beautiful 3-bedroom, 2.5-bath that shows like a model! The first floor features an open floor plan with upgraded tile flooring. The kitchen offers solid surface countertops, a massive island, stainless steel appliances, and a full view of the family room and dining area. The oversized brick paver patio is fenced and would be great for entertaining or your private outdoor retreat. Detached 2-car garage with long driveway for 2 cars. On the second floor, you can find three bedrooms and two full bathrooms. The Main bedroom features a large, en-suite bathroom with dual sinks and a walk-in closet. The HOA includes lawn care. Additional community amenities include a dog park, playgrounds, ponds, and walking trails with outdoor fitness equipment. The clubhouse offers a fully equipped fitness center, resort-style swimming pool, basketball court, Tot-lot, and a party room. Located in an A+ school district. The elementary school, the middle school, and the high school are very close. The property is conveniently located near restaurants, shopping, and attractions. It's a quick drive to downtown Winter Garden, downtown Orlando, the airport, and other major highways. Story Grove is a very well-established community with many activities for the entire family. Do not miss it! This opportunity is fleeting and won't last long.
Listing is courtesy of: BROKERS REAL ESTATE GROUP INC (407-770-1464)
Listing Agent: Beatriz E Dominguez (321-303-4832)
7832 FREESTYLE LN, WINTER GARDEN, FL 34787
$1,075,00096 Days on yellowkey MLS ID: G5107680
REDUCED by $25,000 (2.3%) on 05/06/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2650 Built: 2018Monthly Fee: $300 Tax: $16,616 (2025)Community: Isles Of Lake HancockSingle Family
Taxes:$16,616
Elementary School: Independence Elementary
Middle School: Hamlin Middle
Remarks: Welcome to your new dream home! Located within the exclusive, gated and luxurious community of Isles of Lake Hancock, this stunning 4-bedroom, 3-bath home offers refined design, thoughtful layout, and an elevated way of living. A beautifully pavered driveway and manicured front lawn lead to a three-car garage and covered front patio, setting the tone for the elegance that awaits inside. French doors open to a bright, welcoming foyer where soaring ceilings, recessed lighting, and abundant natural light immediately impress. Just off the entry, the formal dining room is designed for unforgettable gatherings, featuring a dramatic double tray ceiling, striking statement lighting, and a wet bar area with storage that makes hosting feel effortless and elevated. The heart of the home brings together the family room and kitchen in a space that is both inviting and beautifully finished. Exposed ceiling beams add architectural interest to the family room, while the kitchen delivers true luxury with a large island and breakfast bar offering additional storage, premium stainless steel appliances, a stunning range hood, crown-molded cabinetry, and a spacious pantry. Whether you’re preparing a weeknight dinner or hosting a celebration, this kitchen is designed to handle it all with ease. A sunlit dinette just off the kitchen features an angled bay window and elegant lighting, creating the perfect spot for casual meals and morning coffee. A split-bedroom layout enhances privacy, with the primary suite tucked away on its own side of the home. This serene retreat includes private access to the lanai, a generous walk-in closet, and a spa-inspired en suite bath complete with dual vanities, a deep soaking tub, and an expansive walk-in shower, making it an ideal space to unwind at the end of the day. The additional bedrooms are thoughtfully designed with ample storage, natural light, and comfortable space for family or guests. Step outside to the covered lanai featuring retractable patio screens, allowing you to customize your outdoor experience while enjoying al fresco dining or relaxing in the shade. The fully fenced backyard provides peace of mind and room to play, perfect for four legged friends, little ones, or hosting weekend gatherings in the Florida sun. Residents of Isles at Lake Hancock enjoy exceptional community amenities including tennis courts, a residents-only boat ramp, playground, and recreation areas. Known as a nationally recognized water-skiing destination that hosts world-class tournaments, the community also offers convenient access to Walt Disney World, excellent shopping and dining options, upscale golf courses, top-rated schools, and easy access to SR-429 so everything you could need is right at your fingertips. Don't miss out on the opportunity to call this stunning, luxurious home your own. Schedule a private showing TODAY!!!
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Mario Deniz (407-704-0780)
3167 WINESAP WAY, WINTER GARDEN, FL 34787
$575,00018 Days on yellowkey MLS ID: O6400764
0 Days Off yellowkey (back on 4/30/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2115 Built: 2016Monthly Fee: $190 Tax: $5,408 (2025)Community: Orchard Pk/Stillwater XingSingle Family
Taxes:$5,408
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Welcome to 3167 Winesap Way, a beautifully appointed home nestled in the highly sought-after Orchard Park community of Winter Garden. This thoughtfully designed residence offers the perfect blend of comfort, efficiency, and modern style, featuring a spacious open-concept floor plan ideal for both everyday living and entertaining. Located minutes away from top Windermere Schools, Grocery stores, Shopping and entertainment, this home give you all you need right at your door. Enjoy energy efficiency and peace of mind with solar panels, a Tesla charger, Tesla power banks, and a reliable hurricane backup power system. Inside, the home showcases seamless flow between the living, dining, and kitchen areas, all filled with natural light and designed for today’s lifestyle. Step outside to your own private retreat, complete with a dedicated outdoor entertaining area and a cozy fire pit—perfect for relaxing evenings or hosting friends and family on beautiful Florida nights. With its combination of sustainable features, functional layout, and inviting indoor-outdoor living spaces, this home presents a rare opportunity to enjoy both luxury and practicality in one of Winter Garden’s most desirable neighborhoods.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Andrew Tinkler (407-595-9581)
15625 SYLVESTER PALM DR, WINTER GARDEN, FL 34787
$1,105,00094 Days on yellowkey MLS ID: O6379346
REDUCED by $10,000 (0.9%) on 05/06/2026
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
Tax Year: 2024
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 gently lived in by only a couple. From the moment you enter, the barrel ceiling foyer and soaring 10’ 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. 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, and major highways. 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)
1532 SCARLET OAK LOOP #70B, WINTER GARDEN, FL 34787
$345,00082 Days on yellowkey MLS ID: S5143993
REDUCED by $4,000 (1.1%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1544 Built: 2012Monthly Fee: $282 Tax: $3,423 (2024)Community: Tucker OaksTownhouse
Taxes:$3,423
Elementary School: None
Middle School: None
Remarks: Wonderful primary residence or rental investment opportunity! This beautifully maintained 3-bedroom, 2.5-bath condo in the central and peaceful Tucker Oaks community offers the perfect blend of comfort and convenience with a spacious and practical layout. The main level offers a well-appointed kitchen with granite countertops, 42” cabinetry, and a newer refrigerator, seamlessly connected to the living and dining areas, plus a generous laundry room and half bath. The second level offers three generously sized bedrooms, including a comfortable owner’s suite featuring high-velocity impact windows for added efficiency and peace of mind, along with a spacious primary bathroom complete with a relaxing garden tub. The two additional bedrooms share a well-maintained hall bath. Major updates provide peace of mind: NEW A/C (2025), NEW roof (2024), and hot water heater (2023). The attached two-car garage offers secure parking and valuable additional storage space. Residents enjoy access to the community pool — ideal for relaxing weekends or cooling off on warm Florida days. Centrally located just off Route 50 with easy access to major highways, this home is minutes from historic downtown Winter Garden, known for its charming shops, dining options, weekly Farmers Market, and events throughout the year. Outdoor enthusiasts will love the proximity to the West Orange Trail and Oakland Nature Preserve as well as the Arts and Heritage Center in Town of Oakland. The new Costco in Clermont adds even more convenience. Move-in ready and waiting for its next owner, this condo offers low-maintenance living in a prime location. Schedule your private showing today!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Mae Stigell (631-377-1205)
514 DUNBAR AVE, WINTER GARDEN, FL 34787
$295,00039 Days on yellowkey MLS ID: O6394414
0 Days Off yellowkey (back on 4/3/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1162 Built: 2006 Tax: $2,616 (2025)Community: Joe Louis ParkSingle Family
Taxes:$2,616
Elementary School: Maxey Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Welcome to this charming and beautifully updated 3-bedroom, 2-bath bungalow located minutes from the heart of highly desirable Winter Garden! This move-in ready home offers the perfect blend of character, comfort, and modern upgrades—including a brand-new roof for peace of mind. Step inside to discover a warm and inviting layout with stylish updates throughout, creating a light and airy feel that’s perfect for both everyday living and entertaining. The cozy bungalow design offers functionality and charm, making it an ideal primary residence, second home, or investment opportunity. Living in Winter Garden means enjoying one of Central Florida’s most sought-after communities, known for its historic downtown, vibrant lifestyle, and strong sense of community. Just minutes away, you’ll find the award-winning Winter Garden Farmers Market, held every Saturday and featuring over 100 vendors, live music, and a lively, family-friendly atmosphere . Stroll along the charming brick-lined streets of downtown, filled with boutique shops, local dining, and cultural attractions. Don’t miss your opportunity to own this adorable, updated bungalow in one of Central Florida’s most beloved communities—schedule your private showing today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Tara Heard (407-637-4634)
1112 JUNIPER HAMMOCK CT, WINTER GARDEN, FL 34787
$520,00061 Days on yellowkey MLS ID: O6388013
REDUCED by $5,000 (1.0%) on 04/01/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2545 Built: 2002Monthly Fee: $44 Tax: $6,455 (2024)Community: Fullers Crossing Ph 02 49 31Spa: NoSingle Family
Taxes:$6,455
Elementary School: Dillard Street Elem
High School: Ocoee High
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-bedroom, 2-bath home located in the desirable Fullers Crossing Community in charming Winter Garden. This well-maintained residence has over 2,500 square feet of comfortable living space, perfect for families and those who love to entertain. Step inside to discover a bright open floor plan featuring generous living and dining areas, a large kitchen with plenty of cabinet space, and a welcoming family room that flows seamlessly for everyday living. Conveniently located just minutes from shopping, dining, major highways, and the historic downtown district of Winter Garden, known for its popular farmers market, scenic trails and vibrant community events. You couldn't miss this incredible opportunity to own a beautiful home in one of the Central Florida's most sought-after areas. Contact agent to request your showing today! Some photos have been virtually staged.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Dulce Moise (407-697-4754)
900 WALKERS GROVE LN, WINTER GARDEN, FL 34787
$475,000108 Days on yellowkey MLS ID: O6376036
REDUCED by $10,000 (2.1%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1905 Built: 2015Monthly Fee: $280 Tax: $3,950 (2024)Community: Walkers Grove TwnhmsTownhouse
Taxes:$3,950
Remarks: Downtown Winter Garden – Golf Cart District! Don’t miss this amazing opportunity to own a well maintained 3-bedroom, 2.5-bath townhome in the heart of Downtown Winter Garden, right in the highly desirable Golf Cart District—with no rear neighbors! Built in 2015, this home features a spacious layout with tile flooring throughout the first floor, a welcoming foyer, and an open-concept kitchen with granite countertops, stainless steel appliances, pantry, and built-in microwave. The kitchen flows into the dining area and large Great Room—perfect for entertaining. Upstairs, the owner’s suite offers a tray ceiling, walk-in closet, dual sinks, walk-in shower, and a separate soaking tub. Two additional bedrooms, a full bath, and a versatile loft complete the second level. Enjoy your private back patio and a 2-car garage for added convenience. -- Zoned for golf cart use -- Downstairs powder room -- All tile flooring on main level Schedule your showing today—this one won’t last long!
Listing is courtesy of: SPECTRUM PROPERTY GROUP LLC (407-250-5170)
Listing Agent: Laura Taylor (407-496-1162)
6212 ARALIA IVY LN, WINTER GARDEN, FL 34787
$434,90044 Days on yellowkey MLS ID: O6394386
REDUCED by $5,100 (1.2%) on 05/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1560 Built: 2020Monthly Fee: $289 Tax: $6,732 (2025)Community: Hamilton Gardens Ph 2A & 2BTownhouse
Taxes:$6,732
Elementary School: Hamlin Elementary
Remarks: LOCATION! LOCATION! LOCATION! Take advantage of $5,000 in seller concessions! This spacious and beautiful two-story townhome offers the perfect blend of comfort, privacy, and convenience in the highly desirable Hamilton Gardens community. Enjoy an open-concept floor plan, freshly painted interior, and a private outdoor courtyard leading to a rear-entry two-car detached garage. The bright kitchen features granite countertops, a spacious pantry, and overlooks the dining area and great room, creating a seamless space ideal for entertaining. Large windows with blinds fill the home with natural light, enhancing the open feel throughout. Storage is abundant with a pantry, an under-stairs closet, and a generous walk-in closet in the owner’s suite. Upstairs, you’ll find 3 generous bedrooms, 2 bathrooms, and a convenient second-floor laundry. The owner’s suite boasts an enormous walk-in closet and peaceful views of beautiful mature trees. With no neighbors behind, this home offers a quiet, private setting that’s truly rare. Hamilton Gardens provides exceptional amenities, including a resort-style beach-entry pool, cabana, dog park, sports lawn, playgrounds, and scenic garden paths. Residents also enjoy nightly views of the Disney fireworks right from the community. Located just moments from Hamlin Town Center, you’ll have restaurants, cafés, entertainment, and a weekly farmers market less than a mile away. Convenient to SR 429, A-rated schools, top medical facilities, Winter Garden Village, Historic Downtown Winter Garden, and Windermere. A perfect combination of privacy, convenience, and resort-style living—come see it today!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Olga Recean (253-285-2595)
15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787
$820,00044 Days on yellowkey MLS ID: O6393190
REDUCED by $3,900 (0.5%) on 05/01/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3902 Built: 2005Monthly Fee: $243 Tax: $7,653 (2025)Community: Stoneybrook WestSingle Family
Taxes:$7,653
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: One or more photo(s) has been virtually staged. Paid-off whole-house Solar System! Seller offering RATE BUY-DOWN so Buyer will enjoy lower monthly payments! Closing-Cost Assistance! Nestled on this beautifully remodeled and RECENTLY PAINTED home located on a premier OVERSIZED CORNER LOT within the guard-gated enclave of STONEYBROOK WEST, this stunning 5-bedroom, 3-bathroom residence offers the ultimate Winter Garden lifestyle. The home has been meticulously enhanced with MODERN UPDATES, ensuring a MOVE-IN-READY experience for today’s discerning buyer. SAVE ON UTILITY BILLS WITH THE WHOLE HOUSE SOLAR SYSTEM AND ELECTRIC CAR CHARGER. Inside, the open-concept layout is anchored by a SPACIOUS KITCHEN featuring quartz countertops, a central island, and HIGH-END STAINLESS STEEL APPLIANCES, all flowing into a spacious family room warmed by a classic fireplace. High-volume ceilings—reaching 9.25 feet on the main floor and an impressive 10.50 feet in the massive upstairs bonus room—create an airy, grand atmosphere throughout. The well-appointed laundry room includes a GE ULTRA WASHER AND DRYER, along with a STAINLESS STEEL UTILITY SINK for added convenience. The garage is equally impressive, featuring a heavy-duty Husky organizational system that provides exceptional storage and functionality. Retreat to the primary suite, where tray ceilings and a private walk-out balcony offer a peaceful vantage point overlooking the championship golf course. The lifestyle here extends far beyond the front door. Stoneybrook West is a premier “live-play” community boasting 24-hour staffed security and a spectacular waterfront clubhouse perched on the shores of Black Lake. For the outdoor enthusiast, the amenities are unmatched: enjoy private lake access via a community boat ramp and the rare convenience of an on-site boat storage lot. Whether you are hitting the links on the championship golf course, working out in the fitness center, or relaxing at the resort-style pool, every day feels like a vacation. Perfectly positioned for convenience, you are just 6 minutes from Winter Garden Village, 18 minutes from Walt Disney World, and only 30 minutes from Orlando International Airport. This home combines the security of a gated community, the luxury of recent high-end improvements, and the rare perk of Florida lake living. Call today to schedule your private showing!
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
15828 SHOREBIRD LN, WINTER GARDEN, FL 34787
$900,00026 Days on yellowkey MLS ID: O6398059
1 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3058 Built: 2020Monthly Fee: $360 Tax: $11,042 (2025)Community: Lakeshore Preserve Ph 5Spa: NoSingle Family
Taxes:$11,042
Remarks: Under contract-accepting backup offers. Welcome to 15828 Shorebird Lane — a beautifully upgraded Toll Brothers home built in 2020, featuring 4 bedrooms, 3.5 baths, and more than $200,000 in thoughtful enhancements throughout. From the moment you walk in, the home feels bigger, brighter, and more open. The expanded layout adds extra space where it matters most — in the main living areas, bedrooms, and the upstairs loft — giving the whole home an easy, comfortable flow. The kitchen sits right at the heart of the home with upgraded cabinetry, premium appliances, and a large island that makes cooking, gathering, and entertaining feel effortless. It opens directly to the living room and backyard, so everything stays connected. Step outside and you’ll find a space designed to be enjoyed. The screened-in pool and outdoor gas kitchen create a true backyard hangout — perfect for hosting friends or relaxing on a quiet evening. Upstairs, the loft offers a flexible second living area that works as a media room, office, or play space. The three additional bedrooms are well-sized and tucked away for privacy. Details like open stair railings and an extended lanai add to the home’s open, airy feel. Beyond the visible upgrades, the home includes a security system, water softener, epoxy garage flooring, built-in speakers, gutters, and a transferable termite bond for added peace of mind. Located in the Lakeshore community, you’ll enjoy included lawn care and access to amenities along Panther Lake — a zero-entry pool, clubhouse, fitness center, playground, beach volleyball court, dock, and kayak launch. Plus, you’re just minutes from Hamlin Town Center, Orange County National Golf Center, major highways, and Walt Disney World.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
398 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787
$1,498,4405 Days on yellowkey MLS ID: O6405194
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4442 Built: 2024Monthly Fee: $240 Tax: $14,707 (2025)Community: Winter GroveSpa: YesSingle Family
Taxes:$14,707
Elementary School: SunRidge Elementary
Remarks: Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Introducing the exquisite Roseland former model home! This stunning 5-bedroom, 5-bathroom, 2-car garage masterpiece boasts a homesite neighboring a pond and a luxury pool, spa, and outdoor kitchen. As you step through the double entry glass doors, you are immediately greeted by a striking foyer that rises to the second floor, setting the tone for the entire home. To one side, an enclosed flex room offers versatility, while the formal dining room invites effortless entertaining. As you travel further into the Roseland you are greeted by a grand staircase, featuring engineered hard wood plank treads and wrought iron balusters with an oak handrail. Tucked just under the staircase is a wine lover’s dream, a wine cave with built-in cabinets, quartz countertops, and stylish tile backsplash. From there, you enter the heart of the home—the open concept kitchen and living area. Equipped with built-in Whirlpool stainless steel appliances, including a beverage cooler, double oven, and built-in cooktop, the kitchen is a dream for culinary enthusiasts. Two-tone soft-close cabinetry is paired with exquisite quartz countertops, creating a timeless and sophisticated look, while a spacious walk-in pantry ensures ample storage. The open-concept design effortlessly connects the kitchen to the gathering room and cafe, where soaring ceilings create an airy, light-filled space, perfect for both intimate gatherings and larger celebrations. Step outside to the covered lanai and enjoy your backyard oasis complete with an inground pool and spa, as well as an outdoor kitchen. Also located on the first floor, is a “Multi-Gen Suite” offering a spacious bedroom with its own linen closet, walk-in closet, and attached bathroom complete with a frameless glass enclosed shower and quartz countertops. Upstairs, the private owner’s suite spans one side of the home, creating a peaceful retreat. The owner’s retreat area, ideal for reading or unwinding, leads into the spa-inspired owner’s bath, where luxury knows no bounds. A free-standing bathtub, frameless glass-enclosed shower, enclosed toilet, and double walk-in closets create a sanctuary of relaxation. The second floor also offers two additional spacious bedrooms connected by a Jack and Jill bathroom, ensuring both privacy and convenience, while a third bedroom enjoys its own en suite bath, providing an added level of comfort and luxury. The upstairs laundry room, with a utility sink trimmed in quartz and cabinets, makes daily tasks a breeze. With an intelligently designed layout and meticulously curated finishes, this home offers the perfect balance of form, function, and style. It's the epitome of luxury living in a highly sought-after location, blending convenience, sophistication, and thoughtful design into a living experience like no other. Schedule a tour today!
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
15038 WINDFLOWER ALY, WINTER GARDEN, FL 34787
$441,0005 Days on yellowkey MLS ID: O6405201
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1536 Built: 2024 Tax: $5,956 (2025)Community: Osprey Ranch Ph 1Spa: NoTownhouse
Taxes:$5,956
Remarks: Welcome to this beautiful and well-maintained home located in the highly desirable community of Winter Garden. This charming property offers a perfect blend of comfort, functionality, and modern living. Featuring a spacious layout, the home provides ample natural light throughout, creating a warm and inviting atmosphere. The kitchen is designed for both convenience and style, with plenty of cabinet space and room to entertain. The living and dining areas flow seamlessly, ideal for gatherings and everyday living. The bedrooms are generously sized, offering comfort and privacy, while the bathrooms are well-appointed. The property also includes a private outdoor space, perfect for relaxing or enjoying Florida’s year-round sunshine. Conveniently located near major highways, shopping centers, restaurants, and top-rated schools, this home offers both tranquility and accessibility. Don’t miss this opportunity to own a home in one of Winter Garden’s most sought-after areas!
Listing is courtesy of: DTB FLORIDA REALTY, INC. (786-543-8296)
Listing Agent: Pedro Henriq Stuart Lima (813-943-7731)
403 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787
$999,9615 Days on yellowkey MLS ID: O6405130
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2681 Built: 2024Monthly Fee: $240 Tax: $9,118 (2025)Community: Winter GroveSpa: NoSingle Family
Taxes:$9,118
Remarks: Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Step into the Imperial, where luxury and convenience seamlessly combine to create a truly elevated living experience. This remarkable 5-bedroom, 3.5-bathroom former model home with a 2-car garage situated on a conservation view homesite offers unparalleled craftsmanship and thoughtful design throughout. The open-concept layout flows effortlessly, creating an expansive, airy feel that exudes both sophistication and comfort. On the first floor, discover a private en suite bedroom with a walk-in closet and elegant quartz countertops—a perfect retreat for guests. At the heart of the home, the chef-inspired kitchen is a true masterpiece, featuring Winstead Quill cabinetry, striking quartz countertops and a decorative tile backsplash. Built-in Whirlpool stainless steel appliances, including a refrigerator and natural gas cooktop, make cooking a pleasure. The kitchen seamlessly connects to the café and gathering room, where a sliding glass door opens to the covered lanai, featuring an outdoor kitchen that enhances indoor-outdoor living. Beyond the covered lanai, the backyard offers a relaxing fireplace with a waterfall feature on either side, all overlooking tranquil conservation views. The first floor also offers a convenient powder room, perfect for guests, as well as a bedroom with an attached bathroom. Upstairs, the luxurious owner’s suite is a private sanctuary, featuring a spacious walk-in closet (in a built-in closet system) and a spa-like en suite bathroom with quartz-topped dual vanity sinks and a frameless glass enclosed shower. The loft area provides the perfect space to unwind, while three additional bedrooms and another bathroom complete the upper level. For added convenience, a thoughtfully located upstairs laundry room simplifies everyday tasks. Beautiful wood-look tile flooring is found throughout the first floor, laundry room, and bathrooms, while plush, stain-resistant carpet complements the loft and bedrooms. Designer-curated finishes elevate every corner of this home, including thoughtfully placed rain gutters, matte black plumbing fixtures and hardware, built-in drop zone, comfort height toilets, Whirlpool washer and dryer, and wood-look luxury vinyl plank treads and risers at the staircase. This home is equipped with a smart thermostat, video doorbell, LED down lights, digital IP camera pre-wire, surround sound pre-wire, smart irrigation control, and smart door lock and garage door opener ensuring your home is as connected as it is beautiful. This home offers the perfect combination of luxury, convenience, and modern design—an ideal place to live and relax. Schedule a tour today!
11253 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$819,2815 Days on yellowkey MLS ID: O6405126
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2113 Built: 2025Monthly Fee: $199 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Remarks: Under Construction. Waterleigh presents the Bellmore This all concrete block constructed, one-story layout features 4 bedrooms and 3 bathrooms. A beautiful patio welcomes you to a home that optimizes living space with an open concept kitchen overlooking the living area, dining room, and outdoor lanai. Entertaining is a breeze, as this popular single-family home features a spacious kitchen island, dining area and a spacious pantry for extra storage. This community has stainless steel appliances, making cooking a piece of cake. Bedroom one, located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with double bowl vanity, and spacious shower/tub space as well as a spacious walk in closet. Towards the front of the home two additional bedrooms share a second full bathroom. Across the hall a drop zone welcomes you from the garage where you will find a fourth bedroom and full bathroom. This home features a space to fit all your needs. Like all homes in Waterleigh, the Bellmore includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
11283 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$909,4665 Days on yellowkey MLS ID: O6405091
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3225 Built: 2025Monthly Fee: $199 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Remarks: Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry and a half bath. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Off of the family room customize this area to meet your needs with an optional bedroom and full bathroom. As we head up to the second floor, we are greeted with a game room and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Wterleigh, the Torrey includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
5150 CITRUS LEAF BLVD, WINTER GARDEN, FL 34787
$995,0005 Days on yellowkey MLS ID: O6404827
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3461 Built: 2023Monthly Fee: $168 Tax: $12,730 (2025)Community: Silverleaf Reserve/Hamlin Ph 2Single Family
Taxes:$12,730
Remarks: TURN KEY ! This stunning 5-bedroom, 4.5-bath home is packed with upgrades — Calacatta countertops, ceiling-height cabinets, automated curtains, under-cabinet lighting, a gourmet kitchen with tower, Tesla charger, and more! Fully furnished and beautifully maintained, it also features custom-built cabinetry in the living room and office, plus a converted garage gym. Only 2 years old and conveniently located near top-rated Hamlin Elementary and Middle Schools, in a community with a low HOA that includes a pool and sports court. A truly exceptional home in the heart of Hamlin — move-in ready and impeccably maintained!
Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)
Listing Agent: Natalia Romanelli Mourao (407-405-4534)
931 KYLEE ALY, WINTER GARDEN, FL 34787
$825,0005 Days on yellowkey MLS ID: O6404673
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2831 Built: 2022Monthly Fee: $393 Tax: $9,637 (2025)Community: Oakland ParkSingle Family
Taxes:$9,637
Elementary School: Tildenville Elem
Remarks: There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place. As you enter the community, everything feels elevated and thoughtfully composed, with the 22-mile West Orange Trail serving as the heartbeat that connects residents to both nature and one another. At 931 Kylee Alley, this lifestyle is fully realized. Positioned on a prominent corner lot, this David Weekley Stoneybrook residence showcases timeless architecture with a clean, sophisticated presence. One of the greatest luxuries here is the ease of ownership. The homeowners' association provides full landscaping maintenance, allowing the property to remain in pristine condition without demanding your time. Your weekends are yours to enjoy, not manage. Inside, the home immediately impresses with intentional sightlines and natural light. Built in 2022, the design feels both current and enduring. Soaring ceilings and expansive windows, complemented by custom plantation shutters, create a bright yet grounded atmosphere. The gourmet kitchen anchors the home, featuring an oversized island with sleek, solid surface countertops that serve as the perfect setting for gathering, entertaining, or everyday living. The floor plan is designed for both connection and privacy. The main level offers a flexible and refined space that can function as a guest suite or executive-style home office. Upstairs, the private quarters provide a peaceful retreat. The primary suite is expansive and serene, complete with a spa-inspired bath designed for relaxation at the end of the day. Living here means immediate access to the West Orange Trail and the best of Winter Garden. Bike to Plant Street, enjoy the Saturday Farmers Market, or simply take in the charm of one of Central Florida’s most sought-after destinations. Within Oakland Park, residents enjoy resort-style amenities, including multiple pools, a clubhouse, and a dog park, all contributing to a true lock-and-leave lifestyle. From an investment perspective, this property stands out. It offers an exceptional price per square foot for Oakland Park, with pricing thoughtfully adjusted to reflect the opportunity for upstairs flooring customization. In a community where demand continues to outpace supply, especially for newer construction on premium corner lots, this home represents both immediate value and long-term upside. 931 Kylee Alley is more than a home. It is a strategic acquisition within one of Winter Garden’s most desirable communities.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Matthew Mckee (407-948-0658)
16006 GILDEN WAY, WINTER GARDEN, FL 34787
$1,084,99944 Days on yellowkey MLS ID: O6392997
REDUCED by $1 (0.0%) on 05/01/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3617 Built: 2023Monthly Fee: $225 Tax: $12,929 (2025)Community: Encore At OvationSingle Family
Taxes:$12,929
Remarks: Exquisite! Enjoy the experience of living in the finest of modern luxury in this "architecturally" designed estate. Situated in one of the Top Rated communities in Winter Garden, at Encore Ovation, on a 0.38-acre premium lot. Boasting over $200,000 in QUALITY UPGRADES, this residence features, 5 bedrooms and 4 bathrooms. Step onto the elegant 48 X 48 ceramic tiling that flows throughout the main level, transitioning to rich engineered hardwood on the second floor. A striking custom wood and TEMPERED glass staircase serves as a focal point, leading to a spectacular second floor entertainment gallery enclosed in TEMPERED glass with private balcony. A GOURMET DREAM KITCHEN , featuring custom wood cabinetry, Exotic Quartzite countertops, and a custom-fitted pantry. Equipped for the foodie enthusiast, with a SUB -ZERO refrigerator for peak freshness, a Wolf precision oven, a Thermador hub, and a dual-zone wine chiller, for years of gatherings and conversations. Retreat to the oversized travertine-floored lanai, overlooking a sprawling backyard already prepped with plumbing for a summer kitchen-the perfect. The perfect canvas for a custom infinity pool. Other features include;motorized designer blinds, custom lighting installations, and high-efficiency ceiling fans. A spacious garage with built-in overhead storage racks. HOA INCLUDES LAWN CARE AND BASIC LANDSCAPING, for true low-maintenance living.Enjoy resort-style community amenities just steps from your home.These include a clubhouse, fitness center, community pool and steps from a dog park and walking trails. End your day on your private Master Suite balcony, embracing breathtaking sunsets over Lake Mac. Welcome to paradise!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Renee Rodriguez (407-927-2055)
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