Location: Winter Garden
Do Not Show Listings
743 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,499,99915 Days on yellowkey MLS ID: O6392705
0 Days Off yellowkey (back on 4/8/2026)
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4283 Built: 2018Monthly Fee: $298 Tax: $10,715 (2025)Community: Canopy Oaks Ph ISpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,715
Elementary School: Lake Whitney Elem
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: BOM. Buyer decided against stairs. There is a specific kind of silence that exists only within the gated sanctuary of Canopy Oaks. It is the sound of ancient oak leaves stirring in a gentle breeze & the distant, rhythmic splash of a stone fountain. Here, the recipient of the Parade of Homes Grand Award stands as a magnificent testament to what happens when timeless Italian architecture is reimagined for a modern lifestyle. This is not merely a residence. It is a legacy of vertical liberation, a home that breathes with you, scales with your ambitions, and cradles your quietest moments in an embrace of stone and iron. Your journey begins at the threshold of 8-foot, solid double-entry doors. As they swing open, the frantic pace of Central Florida fades, replaced by a two-story foyer that commands immediate respect. A hand forged iron staircase sweeps upward in a graceful arc, mirrored by the delicate charm of a Juliette balcony that suggests a life lived with a touch of Mediterranean flair. Every inch of this grand entrance is a curated experience, designed to transition you into a realm of meticulously crafted prestige where every shadow and light well has been considered. For those who view cooking as a performance art, the professional-grade kitchen is your stage. High-end Kitchen Aid appliances and a natural gas cooktop meet the warmth of artisanal design. The 42-inch upper cabinetry and a hidden walk-in pantry ensure the visual continuity remains unbroken. At the center sits a massive prep island with integrated beverage refrigeration, designed specifically for the art of hosting. Here, the boundary between chef & guest is delightfully blurred. Nearby, the home reveals its most enchanting secret, the drop-down wine cellar. Behind a hand-forged iron gate lies a space that transports you directly to a cobblestone alleyway in Tuscany. With label-forward shelving casting a museum-quality glow & a quaint bistro table within, it evokes the feeling of a private corner in a centuries-old Italian eatery. It is the ultimate setting for an evening pour, a space where time slows down & the modern world feels a thousand miles away. The first-floor owner’s suite is a masterclass in personal seclusion. By design, this space serves as a dedicated haven of quietude, featuring soaring tray ceilings & an atmosphere of total stillness. The spa-inspired bath, featuring a frameless glass walk-through shower & a free-standing soaking tub, offers a daily ritual of total restoration. As you ascend, the lifestyle shifts toward entertainment. The dedicated theater room stands ready for premiere nights, offering a dark, immersive escape. Adjacent, the versatile gathering room opens onto a private balcony overlooking the shimmering resort-style pool & the vast, permanent conservation area. With no rear neighbors, your view is an unbroken tapestry of natural beauty. The outdoor living area features a resort-style pool & spa framed by water/fire bowls & a rainfall pergola. With a full summer kitchen & a backyard that merges into conservation, your privacy is absolute. Enjoy the nightly glow of nearby fireworks from your peaceful terrace, surrounded by the scent of night-blooming jasmine. Strategically along the medical corridor, you are minutes from AdventHealth, Orlando Health & the soul of Winter Garden. Backed by a whole-house natural gas generator & water purification, this home offers security & beauty. Welcome home. Check out the video tour!
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Sean Spencer (407-383-0707)
5679 ORANGE ORCHARD DR, WINTER GARDEN, FL 34787
$649,90027 Days on yellowkey MLS ID: O6389469
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2235 Built: 2021Monthly Fee: $117 Tax: $7,176 (2025)Community: Wincey GrovesSingle Family
Taxes:$7,176
Elementary School: Hamlin Elementary
High School: Horizon High School
Middle School: Hamlin Middle
Remarks: Move-In Ready Home Near Hamlin Town Center with Open Layout and Private Backyard. Built in 2021 and located in the sought-after Wincey Groves community of Winter Garden, this beautifully maintained energy efficient 4-bedroom, 2.5-bath home offers thoughtfully designed living space with modern finishes and a functional open layout. The spacious main living area is filled with natural light and flows seamlessly into the dining space and kitchen, creating an inviting environment for both daily living and entertaining. The Gourmet kitchen upgrade is equipped with premium appliances, ample counter space, and an oversized center island that serves as the heart of the home—perfect for casual meals, gatherings, and hosting friends and family. The primary suite provides a comfortable retreat, featuring two large walk-in closets and a well-appointed en-suite bath. Additional bedrooms are generously sized, offering flexibility for guests, family members, or a dedicated home office. Step outside to enjoy the private fenced backyard with no rear neighbors, providing a peaceful setting for outdoor relaxation. The extensive pavered lanai and trellis area enhances the outdoor lifestyle, making it ideal for entertaining. Other home enhancements include: Custom Shutters, 5 1/4 inch baseboards, Designer lighting, Coffee/Wine Bar, extensive tile plank floors. Conveniently located just minutes from Highway 429, the home offers easy access to the popular Horizon West area. Only 1.3 miles away, Hamlin Town Center features waterfront dining, shopping and family entertainment options. Residents also enjoy proximity to highly rated schools, an extensive network of trails and parks, and nearby world-famous attractions including Walt Disney World. This move-in ready home offers modern construction, privacy, and an exceptional Winter Garden location in one of Central Florida’s most desirable and rapidly growing areas. Make this exceptional home yours today!
Listing is courtesy of: RE/MAX SELECT GROUP (407-352-5800)
Listing Agent: Helen Thompson (407-766-7537)
14282 CREEKBED CIR, WINTER GARDEN, FL 34787
$924,500116 Days on yellowkey MLS ID: O6365928
REDUCED by $5,000 (0.5%) on 04/08/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3479 Built: 2015Monthly Fee: $180 Tax: $7,163 (2025)Community: Bradford CreekSpa: YesSingle Family
Taxes:$7,163
Elementary School: SunRidge Elementary
Remarks: *Seller is willing to contribute up to $5,000 towards interest rate buy down or closing costs*. Experience refined Florida living in this beautifully upgraded Winter Garden residence in the highly sought after gated Bradford Creek community. Thoughtfully designed for both everyday comfort and elevated entertaining, your new home has a rare and highly desirable floor plan with all 4 bedrooms on the main level, combining convenience with timeless style. The spacious primary suite serves as a private retreat with a luxurious ensuite bath featuring a soaking tub and waterfall shower. Two secondary bedrooms with private ensuite baths including one second master bedroom ideal for guests, multigenerational living, or private office space. Upstairs, the expansive bonus room/loft offers endless flexibility for a media room, game room, fitness studio with a large closet that can be converted to a 5th bathroom. Step outside to your own resort-inspired escape with all the bells and whistles to create exceptional setting for relaxing or entertaining year-round. High-end upgrades include the screened travertine lanai, saltwater gas-heated pool, oversized custom saltwater spa, and fully equipped outdoor kitchen with built-in grill and Big Green Egg. Elegant architectural details include crown molding, wainscoting, coffered ceilings, and designer wood-look ceramic tile creating a polished and sophisticated feel. The extended gourmet kitchen is a standout feature, appointed with white shaker cabinetry, granite countertops, double ovens, pot filler, and a premium gas cooktop, making it as functional as it is beautiful. Set on a .30-acre lot with an extended paved driveway conveniently located near Downtown Winter Garden, The Grove, SR-429, Florida’s Turnpike, and Highway 50, this is an opportunity to own a truly distinctive home in one of Central Florida’s most desirable areas. For added modern convenience, the home also includes an EMA outlet for electric car charging, seamlessly supporting today’s lifestyle. Schedule your appointment today and bring your offers.
Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)
Listing Agent: Gislene Moorman (407-694-2246)
15672 SHOREBIRD LN, WINTER GARDEN, FL 34787
$859,90075 Days on yellowkey MLS ID: O6375411
REDUCED by $10,000 (1.1%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2800 Built: 2017Monthly Fee: $360 Tax: $6,887 (2025)Community: Lakeshore PreserveSingle Family
Taxes:$6,887
Elementary School: Panther Lake Elementary
Middle School: Water Spring Middle
Remarks: One or more photo(s) has been virtually staged. Experience refined Florida living in this elegant Toll Brothers built residence, perfectly located on a premium corner homesite in the sought-after Lakeshore Preserve community. Distinguished by its Tuscan elevation, stone accents, and barrel tile roof, this 4-bedroom, 3.5-bath pool home offers timeless curb appeal and thoughtfully designed living spaces. Inside, soaring ceilings, crown molding, and upscale finishes create an inviting yet sophisticated atmosphere. Designed for seamless entertaining, the open-concept kitchen, living, and dining areas are filled with natural light and enhanced by six oversized sliding glass doors that extend the living space outdoors. The gourmet kitchen is the heart of the home, featuring an impressive 14’ center island, upgraded KitchenAid appliances, abundant cabinetry, walk-in pantry, and a built-in storage/mudroom. Outdoors, enjoy a 39’ x 8’ covered lanai overlooking a saltwater pool added in 2021, complemented by extensive paver decking and an expansive screened enclosure—creating a refined outdoor living space ideal for alfresco dining and entertaining. Enjoy the soothing sounds provided by the waterfall pool feature! The first floor includes a flexible bedroom currently used as an office with an adjacent powder room. Upstairs, a spacious bonus loft provides separation and privacy, leading to the luxurious owner’s suite with dual walk-in closets and a spa-inspired bath offering double vanities, soaking tub, frameless glass shower, and private water closet. Two additional bedrooms—one with ensuite bath—along with a full laundry room complete the upper level. Energy-efficient features include double-pane Low-E windows, gas cooktop and dryer, and a tankless water heater. Community fees include lawn care, internet, cable, and access to resort-style amenities such as a clubhouse, pool, fitness center, playgrounds, dog park, firepit and kayak launch. Ideally located in Horizon West, close to shopping, dining, hospitals, schools, and major highways—with Disney parks just minutes away—this home offers the perfect balance of luxury, lifestyle, and convenience.
16006 GILDEN WAY, WINTER GARDEN, FL 34787
$1,150,00012 Days on yellowkey MLS ID: O6392997
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
Elementary School: Water Spring Elementary
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, five bedrooms and four 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)
14416 TRAVOIS WAY, WINTER GARDEN, FL 34787
$794,00040 Days on yellowkey MLS ID: O6382140
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3324 Built: 2022Monthly Fee: $70 Tax: $7,567 (2025)Community: Lake Apopka SoundSpa: NoSingle Family
Taxes:$7,567
Elementary School: None
High School: None
Middle School: None
Remarks: Experience luxury living in one of Winter Garden’s most desirable communities near Hwy 50 & Florida’s Turnpike—just 25 minutes to Downtown Orlando and 20 minutes to Disney. This upgraded Summerlin floor plan offers 5 bedrooms, 4.5 baths, and designer finishes throughout. The fully remodeled kitchen is the true centerpiece—featuring a stunning waterfall-edge island, new cabinetry, upgraded countertops, pantry door, designer lighting, and premium Samsung built-in oven/microwave combo, hood, and pot filler. The oversized island creates the perfect space to gather, entertain, and enjoy everyday living, all open to the main living areas for a seamless flow. This home is loaded with smart and functional improvements, including a Tesla charger, whole-home security system with six cameras and entry sensors, smart front door lock, water softener with reverse osmosis system, new shower heads, additional electrical outlets, and upgraded smoke detection. Step outside to a large, private backyard with a perimeter privacy fence and ample space to design the pool of your dreams The spacious primary suite includes a custom-designed closet and updated bath cabinetry, while a guest bedroom with full bath provides flexibility for visitors or multigenerational living. Step outside to a large fenced backyard with room for a pool. Enjoy an added bonus in the garage of epoxy-coated garage floors and cabinets for additional storage. Conveniently located near Lake Apopka, Hamlin, Horizon West, Winter Garden Village, Downtown Winter Garden, the West Orange Trail, and Walt Disney World—offering the best of Central Florida living with easy access to shopping, dining, and major roadways. Only 11 minutes away from Montverde Academy, one of Florida's most prestigious private schools, and top-rated Oakland Charter School, one of the highest-rated elementary schools in the area.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Carla Robles (407-462-2347)
408 S BOYD ST, WINTER GARDEN, FL 34787
$835,0008 Days on yellowkey MLS ID: O6394810
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2295 Built: 1939 Tax: $2,572 (2025)Community: G T Smith Sub 3Spa: NoSingle Family
Taxes:$2,572
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: Charming home located just blocks from Winter Garden's historical downtown in the highly sought-after GOLF CART DISTRICT! This 3 bedroom, 3 Bath house blends timeless character with modern living, featuring hardwood floors, vintage tiled bathroom, built-ins, and a traditional layout with separate dining room. The kitchen opens to a comfortable family room, ideal for everyday living. The primary suite offers a spacious, spa-like bath with freestanding tub, walk-in shower, and custom vanity. A recent addition includes an oversized two-car garage , HVAC , large pantry, and bathroom to the third bedroom, creating a private en-suite with separate exterior entrance, ideal for guests or flexible living. Situated on a fenced, .41-acre corner lot, enjoy the screened-in back porch, expansive yard with mature landscaping, and the pavered pool area-perfectly designed for entertaining. Live the Historical Downtown Winter Garden Life-Style with convenient access to dining, shopping, farmer's market, Lake Apopka sunsets, and more.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
238 N MAIN ST, WINTER GARDEN, FL 34787
$600,000Listed 04/08/2026 5:13PM MLS ID: O6397340
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1005 Built: 1950 Tax: $5,389 (2025)Community: Orange Grove SubSingle Family
Taxes:$5,389
Remarks: CAN'T GET MUCH CLOSER TO ***HISTORIC DOWNTOWN WINTER GARDEN *** THAN THIS! SERIOUSLY! REFINED OWNER REDO ON THIS FRESH & ADORABLE 3 BEDROOM/2 BATH FENCED YARD SOLID CONCRETE BLOCK CHARMER. *** NO HOA *** HOOOORAY! & WITHIN STEPS TO DOWNTOWN PLANT STREET, TONY'S, HARLOW GROVE RESTAURANT, CHURCHES, FARMERS MARKET, CROOKED CAN FOOD HALL, JESSIE BROCK COMMUNITY PARK, PUBLIC BOAT RAMP AT NEWTON PARK, AND ALL THAT FAST GROWING DOWNTOWN HISTORIC WINTER GARDEN HAS TO OFFER!!! AMAZING CHANGE IS ON THE HORIZON!!!----GET YOURS NOW!!!----- (LOCATED WITHIN THE ZONED GOLF CART DISTRICT). WITHIN MINUTES TO HWY 50, FOWLER GROVES/LOWES/TARGET & 429 FREEWAY ENTRANCE, AS WELL AS FLORIDA TURNPIKE AND E-W EXPRESSWAY ENTRANCES BEING MERE MINUTES AWAY ON EAST PLANT STREET. OH SO CENTRALLY LOCATED DIRECTLY IN "TOWN PROPER" JUST A FEW LOTS UP FROM PLANT STREET. JUST A LITTLE FURTHER AND YOU ARE AT THE PUBLIC BOAT RAMP, NEWTOWN PARK AND FARNSWORTH CITY POOL!!! BEYOND EXCELLENT ACCESS TO MULTIPLE GROCERIES, TAILOR & SHOPPING OPTIONS AT HWY 50, PARK AVENUE, DILLARD STREET AND NEARBY OAKLAND! ALSO, THE WEST ORANGE TRAIL RUNS PERPENDICULAR TO MAIN STREET (YOUR STREET) & IS STEPS FROM YOUR HOME-----CONCRETE BLOCK CONSTRUCTION BUILT W/TERMITE BOND/MONTHLY PEST TREATMENT-ALL WITH MASSEY SENTRICON & TRANSFERABLE BOND TO THE NEW OWNER--- HOME HAS GROOMED MATURE OAKS WITH FENCED IN BACK YARD (WOOD PLANK AND VINYL) WITH ELEVATED WOOD DECK FOR BARBECUES AND ENTERTAINING!!! ***EXCELLENT VALUE/EXCELLENT LOCATION/GOLF CART DISTRICT/NO HOA!***--WHY RENT WHEN YOU CAN (OWN) YOUR OWN PROPERTY FOR JUST A FEW HUNDRED DOLLARS MORE PER MONTH? CHECK LEASE RATES,...YOU'LL SEE....RENTS ARE HIGH IN WINTER GARDEN, SO WHY MAKE YOUR LANDLORD RICH WHEN YOU CAN HAVE A LONG TERM INVESTMENT AND (OWN) WHILE APPLYING THAT MONTHLY PAYMENT TO YOUR OWN MORTGAGE, RATHER THAN THE LANDLORD?------HOME WARRANTY OPTIONS AVAILABLE. THANK YOU!
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Jason Fulmer (321-303-6670)
10031 BEDTIME STORY DR, WINTER GARDEN, FL 34787
$669,000257 Days on yellowkey MLS ID: O6329801
REDUCED by $6,000 (0.9%) on 04/08/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2722 Built: 2018Monthly Fee: $209 Tax: $912 (2023)Community: Storey Grove 50Single Family
Taxes:$912
Tax Year: 2023
Remarks: ***This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.*** Welcome to 10031 Bedtime Story Drive—where comfort, convenience, and community come together in one incredible home. Perfectly positioned on a premium corner lot in the sought-after Storey Grove neighborhood, this spacious 4-bedroom, 4-bathroom residence offers over 2,700 square feet of upgraded living space on a generous quarter-acre lot with a 2-car garage. Inside, you’ll find fresh updates throughout, including brand-new carpet and padding, new ceiling fans, modern pendant lighting in the kitchen, updated door hardware, and a fresh coat of paint that gives the home a like-new feel. The open-concept layout flows seamlessly from the chef-style kitchen—now featuring freshly refinished upper cabinets paired with gray lowers, stainless steel appliances, and a sliding door has been added to the pantry for improved space and style—to the inviting living and dining areas with crown molding, ideal for entertaining or relaxing. The bathrooms have also been upgraded with new fixtures and striking navy blue cabinetry for a modern, designer look. Closet organizers were installed in both the primary suite and one of the downstairs bedrooms for added function. One of the standout features is the enclosed upstairs loft with its own full bathroom, added closet, making it perfect as a mother-in-law suite, second master bedroom, game room, or fifth bedroom. The primary suite on the main level offers a spacious walk-in closet and a spa-inspired bathroom. Step outside to a covered patio and enjoy private backyard views, where you can even watch Disney fireworks and rocket launches in the distance. Additional highlights include a dedicated laundry room, security system, thermal windows, pest control service, and lawn care included with the HOA. Storey Grove offers residents access to top-rated schools, including Horizon High School and Water Springs K–8, along with an impressive list of community amenities such as a clubhouse, fitness center, dog park, playground, resort-style pool, tennis courts, and beautifully maintained parks and trails. This home blends thoughtful upgrades, a flexible layout, and a prime location—making it the perfect fit for families or those seeking multigenerational living. Don’t miss your chance to tour this exceptional Winter Garden property. Schedule your showing today.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Tyler Somers (561-713-8728)
11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$899,990114 Days on yellowkey MLS ID: O6367437
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3327 Built: 2025Monthly Fee: $200 Tax: $1,989 (2024)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Tax Year: 2024
Remarks: Under Construction. Waterleigh presents the Seacliff. 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. Customize this area to meet your needs with an optional den. Go down the hallway and you’ll find a powder room and laundry room tucked behind the stairwell leading up to the second floor. 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 a walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one bathroom impresses with separate vanities, shower/tub space, toilet room with privacy door as well as a spacious walk in closet. As we head upstairs, you are greeted with a loft area and all three bedrooms. Two bedrooms share an upstairs bathroom with double bowl vanity while the additional bedroom is complete with ensuite bathroom. Like all homes in Waterleigh the Seacliff includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. This home is open for self-touring 7 days a week. *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)
441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787
$1,199,90034 Days on yellowkey MLS ID: O6385964
INCREASED by $80,900 (7.2%) on 04/02/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4001 Built: 2000Monthly Fee: $83 Tax: $5,551 (2024)Community: Courtlea OaksSpa: YesSingle Family
Taxes:$5,551
Elementary School: Tildenville Elem
Remarks: One or more photo(s) has been virtually staged. One of the largest homes in the highly desirable Courtlea Oaks community, this spacious 5-bedroom, 4.5-bath pool home offers over 4,000 square feet of living space and an exceptional opportunity in the heart of Winter Garden’s golf cart district. The flexible floor plan includes a rare apartment above the garage connected to the main home, providing ideal space for guests, extended family, a private office, or additional living quarters. Important updates have already been completed by these original to the home owners, including a new roof and A/C systems installed just two years ago, offering peace of mind for the next owner. Step outside to enjoy a beautiful pool and a private setting backing to the West Orange Trail, perfect for biking, walking, and outdoor recreation right from your backyard. Located just minutes from historic downtown Winter Garden, residents enjoy boutique shopping, dining, breweries, and the award-winning Saturday Farmers Market, along with numerous festivals and community events throughout the year. With its generous square footage, versatile layout, and unbeatable location, homes like this rarely come available in Courtlea Oaks.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Jennifer Coon (321-948-8056)
813 MARSH REED DR, WINTER GARDEN, FL 34787
$609,000288 Days on yellowkey MLS ID: O6321149
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3148 Built: 2015Monthly Fee: $128 Tax: $8,220 (2024)Community: Johns Lake PointeSpa: NoSingle Family
Taxes:$8,220
Remarks: One or more photo(s) has been virtually staged. Significant Price Improvement! This spacious residence offers refined finishes and a thoughtfully designed layout, beginning with elegant porcelain tile in the main living areas and luxury vinyl plank flooring in all bedrooms and throughout the upper level. The chef-inspired kitchen serves as the heart of the home, featuring granite and quartz countertops, abundant cabinetry, and a generous walk-in pantry for exceptional storage and functionality. A versatile flex room on the main floor, accented with French doors, provides the ideal space for a guest suite, home office, or private den. The secluded owner’s retreat is a true sanctuary with a split-bedroom layout, expansive walk-in closet, dual granite vanities, and a relaxing garden tub. Upstairs, a spacious loft creates additional living or entertainment space, while a second suite impresses with dual vanities, granite counters, a separate shower and soaking tub, and two oversized walk-in closets. Two additional bedrooms, two full baths, and a conveniently located laundry room complete the upper level. Storage is abundant throughout, including a large under stair closet. Step outside to a serene backyard with tranquil water views from the screened, covered patio. Envision enhancing the space with a privacy fence and mature landscaping to create your own peaceful retreat. With a recent price improvement, this home presents outstanding value, flexibility, and the opportunity to personalize to your taste. Ideally located less than 20 minutes from Disney, Johns Lake Pointe is a beautifully maintained community offering resort-style amenities including a clubhouse with pool and kitchen, fitness center, yoga room, tennis courts, playground, and access to a public boat ramp on the 2,500-acre Johns Lake. Enjoy an exceptional lifestyle in a prime location, priced to allow the next owner to create a private oasis. Don’t miss the opportunity to make this remarkable home your own.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Carla Scherer (407-443-7482)
16391 ADMIRALS COVE LN, WINTER GARDEN, FL 34787
$540,000321 Days on yellowkey MLS ID: O6311344
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2200 Built: 2020Monthly Fee: $254 Tax: $8,126 (2024)Community: Waterleigh Ph 3B & 3CSingle Family
Taxes:$8,126
Remarks: Price reduced – motivated seller! Welcome to this stunning home in the highly desirable Waterleigh community in Winter Garden! This beautiful two-story residence features 3 spacious bedrooms, 2.5 bathrooms, and a versatile flex space perfect for an office, playroom, or guest area. With over 2,200 sq ft of living space and a smart, open-concept layout, this home offers both comfort and functionality. Enjoy a modern kitchen with stainless steel appliances, granite countertops, and a large island — perfect for entertaining. Upstairs, the oversized master suite includes a walk-in closet and a luxurious ensuite bathroom. Additional highlights include a two-car garage, smart thermostat, and irrigation system. One of the standout features is the solar energy contract, which keeps energy bills incredibly low — just $162.31 monthly, significantly less than traditional electricity costs for a home of this size. The solar contract will be transferred to the new owner, providing long-term savings and eco-friendly living from day one. The Waterleigh community offers resort-style amenities, including swimming pools, fitness centers, tennis courts, mini golf, playgrounds, walking trails, and more — all just minutes from top-rated schools, shopping, and Disney. Don’t miss this incredible opportunity to own a well-maintained, income-producing property in one of Winter Garden’s most sought-after neighborhoods! This home is currently leased at $3,150/month with a responsible tenant in place. The tenant is open to renewing the lease if the buyer is an investor, or is also willing to vacate the property within 30 days of notice without penalty if the new owner wishes to occupy it.
Listing is courtesy of: FLORIDA 360 REALTY LLC (561-513-5162)
Listing Agent: Valquiria Pidgeon (954-325-2625)
6408 FLAT LEMON DR, WINTER GARDEN, FL 34787
$570,0001 Day on yellowkey MLS ID: O6396757
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1979 Built: 2019Monthly Fee: $142 Tax: $8,155 (2025)Community: Hamlin ReserveSingle Family
Taxes:$8,155
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Tucked inside Hamlin Reserve in the heart of Horizon West, this beautifully maintained one-story home offers the kind of lifestyle buyers are looking for: modern, low-maintenance, and close to everything. Built in 2019 and still feeling like new, this 3-bedroom, 2-bath home with 1,979 heated square feet blends comfort, function, and thoughtful upgrades in all the right ways. From the moment you step inside, the open layout feels bright, welcoming, and easy to live in. Hardwood Laminate flooring runs throughout the entire home, including the bathrooms, creating a clean and cohesive look. The flexible dining room offers extra versatility and could easily become a private office, playroom, or enclosed flex space with French doors. The backyard is set up to be enjoyed, with a fully fenced yard ideal for pets, plus a built-in patio deck and firepit that make it easy to picture cozy evenings outside, weekend gatherings, or quiet mornings at home. Solar panels help drastically reduce the monthly electric bill, and the sellers will pay them off at closing, giving the next owner an added benefit from day one. Living in Hamlin Reserve means enjoying a community pool and being just minutes from the 429, Disney, shopping, grocery stores, dining, and all the energy and convenience that make Horizon West one of Central Florida’s most desirable places to call home. With no CDD, a move-in ready condition, and a location that continues to grow, this home is an ideal fit for buyers looking for both lifestyle and value. SAVE BIG: 1% Broker credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred broker.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Clementine Costantini (407-692-5453)
720 LAKE BRIM DR, WINTER GARDEN, FL 34787
$1,850,00033 Days on yellowkey MLS ID: O6387519
REDUCED by $49,000 (2.6%) on 04/01/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3781 Built: 2020Monthly Fee: $203 Tax: $14,831 (2025)Community: Oakland ParkSpa: NoSingle Family
Taxes:$14,831
Remarks: Experience refined Florida living in the heart of Winter Garden, where timeless architecture, thoughtful design, & an unbeatable location come together in this exceptional custom-built residence. Situated on an expansive corner lot (~1/4 of an acre) overlooking one of the community’s most beloved PARKS, this four-bedroom (w/ room for a 5th & office), four-bath luxury HEATED POOL home offers privacy, space, & picturesque views. You’re moments from stunning sunsets, a walk by the LAKE, multiple parks & playgrounds, the community clubhouse, & direct access to the scenic WEST ORANGE TRAIL— a 22-mile paved trail ideal for biking, jogging, & casual strolls. From the moment you arrive, the stunning brick-accented front porch sets the tone, offering a welcoming space to relax while enjoying tranquil park views. Inside, rich wood flooring flows throughout the main living areas, complementing the home’s elevated finishes, such as crown molding, wainscoting, trim work, & custom built-ins. At the heart of the home, the chef’s kitchen is a true showpiece. Outfitted with premium Thermador & JennAir appliances, QUARTZITE counters, custom cabinetry, designer fixtures, a walk-in pantry, & spacious gathering space, this kitchen was designed for both everyday living & elegant entertaining. The adjacent dining & living areas are bathed in natural light, enhanced by multiple French doors that frame panoramic views of the pool and backyard retreat. The indoor-outdoor connection is simply spectacular. Step outside to your private oasis featuring a sparkling resort-style pool (runs with an ozonator) with travertine decking, generous covered lanai, & an outdoor kitchen equipped with a mini fridge & 48 inch griddle. Each of the four bedrooms is generously sized, offering comfort & versatility for family & guests. One generously sized bedroom is downstairs, which has access to the pool & park through French doors. The primary suite serves as a luxurious retreat with a spa-like bath & dual closets, while all four baths (three en-suite) are thoughtfully designed with quality finishes (marble upstairs, quartzite downstairs). Need an elevator? There's space for the addition! A well-appointed MUDROOM adds everyday convenience & organization, seamlessly blending practicality with style. Additional FEATURES: whole house water filtration system, in-ceiling speakers in the living room, the lanai by the pool, & front porch, tankless water heaters, hard wired cameras inside/out, ample storage, landscape lighting, Cat 6 wiring w/ WiFi access points, & an OVERSIZED garage (~2 1/2). Just a short GOLF CART ride away, you’ll find the charm & vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, community connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks. Custom built POOL homes are RARE to market in Oakland Park. Make this DREAM home your reality today!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Ashley Boyd (321-209-5540)
16230 CARRAWAY BAY ALY, WINTER GARDEN, FL 34787
$573,00072 Days on yellowkey MLS ID: NS1087076
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2474 Built: 2024Monthly Fee: $291 Tax: $2,273 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$2,273
Remarks: Welcome to 16230 Carraway Bay Alley, a beautifully maintained home located in the heart of Winter Garden. Situated in a desirable community with convenient access to shopping, dining, and major highways, this property offers a perfect blend of comfort, style, and location. The home features a thoughtfully designed layout with spacious living areas, abundant natural light, and modern finishes throughout. The kitchen opens to the main living space, making it ideal for both everyday living and entertaining. The primary suite provides a private retreat with ample closet space and an en-suite bathroom. Enjoy low-maintenance living with outdoor space perfect for relaxing or hosting guests. Community amenities and nearby attractions enhance the lifestyle appeal, with close proximity to downtown Winter Garden, top-rated schools, and scenic trails. Convenient access to SR-429 and the Florida Turnpike makes commuting easy.
Listing is courtesy of: WATSON REALTY CORP (386-428-7355)
Listing Agent: Matthew Eads (804-651-6911)
16736 OAKBORO ST, WINTER GARDEN, FL 34787
$585,00020 Days on yellowkey MLS ID: O6388784
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2020Monthly Fee: $257 Tax: $6,967 (2024)Community: WaterleighSpa: NoSingle Family
Taxes:$6,967
Remarks: WHOLE HOUSE SOLAR PANELS INCLDED IN PURCHASE! Be delighted with the reduced energy expenses from the day you move in. Don't wait to build! Great opportunity to make homeownership a reality in the beautiful community of Waterleigh in Horizon West. Waterleigh offers resort style amenities catering to any lifestyle, including a large club house with community room and fitness center that opens to a freeform pool, grilling stations and plenty of deck space to relax in the Florida sun. The sports enthusiast will fall in love with the multiple ball fields, tennis courts, beach volleyball court, pickle ball and outdoor fitness circuit. Playgrounds, gazebos and parks are scattered throughout the community for your pleasure. Phase three has a separate pool that is a great alternative to the main pool complex. This Clearden model offers many options and versatility. Natural light is amazing in every room! The first floor features an open plan with a bright white kitchen featuring a center island, stainless steel appliances, walk-in pantry as well as a coffee or dry bar area and overlooks the spacious family room that leads to the covered lanai. Main floor full bedroom with a private bath is ideal for guests, an office or an in-law suite. Upstairs there is an open loft, three additional bedrooms and a large laundry room. The expansive primary suite has an ensuite bathroom equipped with a double vanity, walk-in shower and plenty of closet space. The entertaining expands to the outside with covered front and rear lanais perfect for morning coffee or an evening BBQ. The fully fenced yard, whole home water softener, security system and solar panels add to the many upgrades in this beautiful home. Attached rear entry oversized two car garage provides plenty of room to park two vehicles and the brick paver driveway can accommodate up to four additional vehicles. Take advantage of the many community activities that are sponsored by the HOA for your pleasure year-round. Zoned for top rated schools including the elementary and middle schools within walking distance. Shopping, restaurants and lifestyle shops are all within the planned community. Minutes to the Walt Disney World complex, major roadways and an easy commute to the Orlando International Airport or Downtown Orlando. Special note, this home is equipped with Solaredge Solar panels that come with a transferrable warranty to the new Owner. This feature significantly reduces the monthly power bill! Call today for a private showing.
Listing Agent: Michael Morris (407-383-5434)
2439 BALFORN TOWER WAY, WINTER GARDEN, FL 34787
$570,00040 Days on yellowkey MLS ID: O6386373
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2508 Built: 2008Monthly Fee: $243 Tax: $3,490 (2025)Community: Stoneybrook West DSpa: NoSingle Family
Taxes:$3,490
Elementary School: Whispering Oak Elem
Remarks: *Video Tour Available!* Experience the best of Florida living in the heart of Stoneybrook West, where resort-style amenities and a true sense of community come together. Behind 24-HOUR GUARD GATED ENTRANCE, you’ll find everything you need to live like you’re on vacation year-round—an Olympic-sized swimming POOL, splash zone, FITNESS CENTER, playground, tennis, basketball and pickleball courts, a fishing pier, plus a PRIVATE BOAT RAMP on Black Lake. Even better, the quarterly HOA INCLUDES SPECTRUM INTERNET AND CABLE, making life here as convenient as it is enjoyable. Tucked away on a quiet CUL-DE-SAC STREET with no through traffic, this home offers both privacy and charm from the moment you arrive. Warm curb appeal welcomes you inside to rich WOOD FLOORS and soaring ceilings that create a light, airy Florida feel. At the front of the home, the FORMAL LIVING AND DINING ROOMS provide flexible space for entertaining or working from home, highlighted by a welcoming staircase. Designed for gathering, the OPEN FLOOR PLAN seamlessly connects the family room and eat-in kitchen. The kitchen features abundant QUARTZ COUNTERTOPS, upgraded cabinetry, and a pantry to keep everything organized. Double sliding doors from both the kitchen and family room open to a SCREENED PATIO OVERLOOKING A PEACEFUL POND—no rear neighbors, just tranquil views and evening sunsets. Upstairs, you’ll find the bedrooms along with a convenient laundry room. The primary suite is spacious with wood floors, double sinks, quartz countertops, a water closet, and WALK-IN CLOSET. The RENOVATED SECOND BATHROOM offers a beautifully tiled shower and tub with a built-in shampoo niche. Generously sized secondary bedrooms feature deep closets for all your storage needs. Additional upgrades include ceiling fans throughout the home and patio, a convenient half bath downstairs, new irrigation panel, updated faucets and shower head in the primary bath, newer microwave and refrigerator, window blinds and exceptional storage throughout. This is more than a home—it’s your opportunity to embrace the Florida lifestyle, where sunny days, waterfront adventures, and a vibrant community are all right outside your door.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Tennille Biggers (850-628-4455)
9107 GRAND ISLAND WAY, WINTER GARDEN, FL 34787
$505,00023 Days on yellowkey MLS ID: O6391117
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2082 Built: 2017Monthly Fee: $159 Tax: $7,996 (2025)Community: Watermark Ph 2CSingle Family
Taxes:$7,996
Remarks: Welcome to 9107 Grand Island Way, a beautiful Corner Lot Home in the heart of Horizon West’s Watermark community! This home is the perfectly balance of comfort, style, and convenience, designed for both everyday living and entertaining. Upon entering the front door, you will see your updated, modern kitchen with granite countertops, modern 42" cabinets and modern pendant lights overlooking your spacious living room. You will space for a nice dining room table to entertain as well as a half bathroom and the entrance to the 2 car garage! Upon walking up the modern staircase, you will find a very nice spaced loft/entertainment room, to where you can have your private second living room, office or movie theater room! The primary bedroom provides a relaxing and spacious space with a nice sized primary bathroom and walk in closet, while the additional bedrooms offer flexibility for family, guests, or a home office. As this is a corner lot, there home is filled with natural light. flowing seamlessly into the kitchen and dining space. One of the most unique aspects of this property is its prime corner location directly across from the vibrant Horizon West Retail Center, placing you just steps from such stores like Starbucks, New York Beer Project, 7-11 and Walgreens and more! Enjoy the rare ability to walk or bike to dining, entertainment, and local hotspots while still enjoying the privacy of a residential neighborhood. Residents of Summerlake enjoy resort-style amenities including a community pool, clubhouse, fitness center, dog parks, playgrounds and more! With easy access to Interstate 429, Hamlin Town Center, top-rated schools, Orange County National Golf Center and Walt Disney World just minutes away, this home offers the perfect balance of lifestyle and location in one of Winter Garden’s most sought-after communities conveniently located in the middle of everything!
Listing is courtesy of: FHG REALTY, LLC (407-505-7600)
Listing Agent: Jeff Inman (407-505-7600)
9723 LOST CREEK DR, WINTER GARDEN, FL 34787
$669,000149 Days on yellowkey MLS ID: O6359309
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2117 Built: 2021Monthly Fee: $261 Tax: $10,499 (2025)Community: WaterleighSingle Family
Taxes:$10,499
Remarks: Beautiful 4-bedroom, 3 bath water view home in Waterleigh, Horizon West’s Premier Community! Welcome to your next chapter in Waterleigh, where resort-style amenities and thoughtful design come together in one of Horizon West’s most desirable neighborhoods. This impeccably maintained 4-bedroom, 3-bath home offers 2,117 sq. ft. of single-story comfort, ideal for families, first-time buyers, or those seeking a low-maintenance lifestyle. Interior features include a bright open floor plan with elegant archways, a spacious kitchen with stainless steel appliances, stone countertops, ample cabinet and counter space, and a roomy breakfast bar, a large family room with view of the pond and a split floorplan for privacy and versatility. The master suite boasts a beautiful tray ceiling and a master bath with a garden tub, separate shower, dual sinks and a large walk-in closet. The rear lanai has brick pavers and a one of a kind east facing view of the pond where you can enjoy your morning coffee and watch the sunrise. Out front there's a lovely front porch that adds to the neighborhood charm. Enjoy access to multiple clubhouses, resort-style pools, fitness centers, playgrounds, dog parks, walking trails, and year-round community events. HOA dues include landscaping, giving you more time to enjoy the lifestyle. Don't miss this fantastic opportunity.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ping Ma (863-332-0298)
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