Location: Winter Garden
Do Not Show Listings
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,389
Elementary School: Dillard Street Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
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)
12983 HARVEST RAIN AVE, WINTER GARDEN, FL 34787
$750,000Listed 04/08/2026 9:39PM MLS ID: O6397592
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2858 Built: 2026Monthly Fee: $140Community: Harvest At OvationSingle Family
Taxes:$0
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Under Construction. What's Special: Flat Lot | Close to Amenity | Flex Room. New Construction - May Completion! Built by America's Most Trusted Home Builder. Welcome to the Ozark at 12983 Harvest Rain Avenue in Harvest at Ovation! This new home has an inviting gallery-style foyer welcoming you inside and leads past a dedicated study into the open main living area where the dining space flows seamlessly into the gathering room and gourmet kitchen. The kitchen shines with quartz countertops, an apron front stainless steel kitchen sink, cabinets at the kitchen island, and a spacious walk-in pantry designed to keep everything within reach. Pocket sliding doors from the gathering room open to an extended lanai, creating an easy connection between indoor and outdoor living. The primary suite is tucked quietly at the back of the home and features a spa-inspired en-suite bath and a large walk-in closet. Two secondary bedrooms, including one with its own en-suite bath, along with an additional full bath, powder room, nearby laundry area, and a two-car tandem garage complete this thoughtfully designed home. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: Gourmet kitchen, study in place of flex, pocket slider at gathering room, shower at bath 3, extended lanai, 8' interior doors, second sink at bath 2, and whole house blinds. Photos are for representative purposes only. MLS#O6397592
Listing is courtesy of: TAYLOR MORRISON REALTY OF FLORIDA INC (407-756-5025)
Listing Agent: Michelle Campbell (407-756-5025)
14501 GROVE RESORT AVE #1310, WINTER GARDEN, FL 34787
$230,000Listed 04/08/2026 11:20AM MLS ID: O6397317
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1265 Built: 2016Monthly Fee: $608 Tax: $6,200 (2025)Community: Grove Resort And Spa Hotel CondoCondo
Taxes:$6,200
Elementary School: None
High School: None
Middle School: None
Remarks: Fully Furnished & Turn-Key Ready! Welcome to your dream vacation retreat at the highly sought-after Grove Resort & Spa—a full-service luxury resort just 10 minutes from Disney World! This spacious 2-bedroom, 2-bathroom Jasmine Model is located on the 3rd floor and offers 1,265 sqft of comfortable living space, including a screened-in balcony with serene views. Enjoy the ultimate resort lifestyle with incredible on-site amenities: a full water park with dual water slides, a FlowRider® double surf simulator, lazy river, splash zones, multiple pools, private cabanas, restaurants, spa, fitness centers, arcade game room, mini golf, walking trails, and more. The resort also features a convenient alfresco market and offers complimentary shuttle service to Disney for your added ease. The unit is fully furnished with a king-sized bed in the primary suite and a queen bed in the secondary bedrooms—perfect for families or guests. Located just off I-192, you’re minutes from shopping, dining, and all of Orlando’s top attractions. Truly turn-key and resort living at its best—call today to schedule your private showing!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Vinny Apolinario (407-371-2227)
15120 SHONAN GOLD DR, WINTER GARDEN, FL 34787
$1,745,00041 Days on yellowkey MLS ID: O6386104
5 Days Off yellowkey (back on 4/8/2026)
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3487 Built: 2020Monthly Fee: $230 Tax: $16,822 (2025)Community: Overlook At HamlinSpa: YesSingle Family
Taxes:$16,822
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautiful Winter Garden lakefront home with 270-degree lake views, a resort pool, and location, location, location. This one-story, four-bedroom, four-bath open floor plan home features a modern infinity-edge pool overlooking stunning views of Lake Hancock, with an oversized fenced-in backyard. Just three minutes to everything in Hamlin. The home also features an office/flex room and is located three minutes off 429 and New Independence Parkway, 30 minutes to the Orlando International Airport, 25 minutes to downtown Orlando, 20 minutes to Disney World, 12 minutes to Winter Garden Village, and 3 minutes to the movies, theaters, several restaurants, and shopping. This property has one of the best views on Lake Hancock in one of the best locations — a one-of-a-kind lakefront home in Winter Garden, Florida, that you must see for yourself.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jason Ogden (321-320-1449)
17606 LAKE STAR RD, WINTER GARDEN, FL 34787
$870,00050 Days on yellowkey MLS ID: O6382909
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2605 Built: 2023Monthly Fee: $83 Tax: $12,316 (2024)Community: Northlake/Ovation Ph 1Single Family
Taxes:$12,316
Tax Year: 2024
Remarks: Luxury Home for Sale in Winter Garden – Lake View Be enchanted by this beautiful contemporary residence, located in one of the most desirable areas of Winter Garden. This property combines elegance, comfort, and functionality in every detail, offering 4 bedrooms, 3 full bathrooms, and 1 powder room, with spacious and integrated environments in a modern open concept, enhanced by large windows that provide excellent natural lighting. The living room features a charming electric fireplace and sophisticated finishes. The house stands out for its high-standard custom-designed cabinetry, with over US$80,000 in upgrades, including custom-made furniture in the powder room, laundry room, living areas, and other spaces, adding refinement, organization, and exclusivity throughout the home. There is also a private office, ideal for those who work from home or need a quiet environment for studying. The kitchen is a true highlight: fully equipped with appliances and seamlessly integrated with the dining and living rooms. It features a spacious marble countertop, high-quality custom wood cabinetry, and an excellent layout for entertaining friends and family. The bedrooms offer carpeting and built-in closets, ensuring comfort and practicality. Additionally, all bedroom windows are equipped with remote-controlled blackout shades, providing privacy, convenience, and enhanced comfort at the touch of a button. The master suite is spacious and elegant, featuring a large bathroom and a generous walk-in closet. The laundry room comes fully equipped, adding even more convenience to daily life. The garage accommodates up to 3 vehicles. Outside, the residence impresses with a large covered and screened veranda, perfect for relaxing and enjoying leisure time, with direct access to the backyard and an enchanting lake view that creates a peaceful and welcoming atmosphere. Located in the Northlake community, the property offers excellent amenities, including a swimming pool, clubhouse, park, walking trails, and a safe, family-friendly environment. The location is truly privileged, just minutes from Hamlin Town Center, offering a variety of restaurants, shops, and a movie theater, as well as major supermarkets like Publix and Walmart. It also provides easy access to FL-429 and is conveniently close to the world-famous attractions of Walt Disney World and the greater Orlando area. A unique opportunity for those seeking quality of life, sophistication, and a spectacular lake view in Winter Garden. Schedule your visit and come see your new home.
Listing Agent: Daniel Pavel (407-747-3408)
743 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,499,99916 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
Taxes:$10,715
Elementary School: Lake Whitney Elem
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
$649,90028 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
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
$924,500117 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
$859,90076 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
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
$1,150,00013 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
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
$794,00041 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
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
$835,0009 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
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)
317 SOUTHERN PECAN CIR #102, WINTER GARDEN, FL 34787
$232,00044 Days on yellowkey MLS ID: O6384866
REDUCED by $8,000 (3.3%) on 04/08/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 738 Built: 2005Monthly Fee: $309 Tax: $245 (2025)Community: Southern Pines CondominiumCondo
Taxes:$245
Remarks: Welcome to Southern Pines in the heart of Winter Garden! This clean and well-maintained 1-bedroom, 1-bath upstairs condo offers bright, open living with a rare combination of features you won’t often find in the community. Positioned on the upper level, the home enjoys enhanced privacy and abundant natural light with windows on both sides of the building, creating an airy and inviting atmosphere throughout the open-concept living and dining area. The kitchen flows seamlessly into the main living space and features granite countertops, ample storage, and all appliances convey with the sale — making this home truly move-in ready. Enjoy peaceful views overlooking the community tennis courts and resort-style pool. Downstairs, the attached 1-car garage and generous under-stair storage closet provide exceptional storage space — a true rarity within the neighborhood. Enjoy maintenance-free living, with HOA fees covering lawn care, cable, internet and water. Spend your weekends exploring Winter Garden Village, just 1.5 miles away, or immerse yourself in the charm of historic Downtown Winter Garden, filled with cozy cafés, boutique shops, farmers markets, and more. Outdoor enthusiasts will appreciate easy access to the West Orange Trail, perfect for biking, jogging, or leisurely strolls. Commuting is effortless with quick connections to the Florida Turnpike, SR 408, and SR 429. The gated Southern Pines community offers impressive amenities, with the pool, hot tub, and clubhouse located across the street. Additional features include a covered playground, movie theater, game room, office space, outdoor kitchen with grills, tennis court, indoor basketball and racquetball courts, sand volleyball, and even a car wash station. Don’t miss your opportunity to own in one of Winter Garden’s most convenient and amenity-rich communities. Schedule your showing today.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Anna Gay Hunter (407-446-9878)
10031 BEDTIME STORY DR, WINTER GARDEN, FL 34787
$669,000258 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)
15663 KINNOW MANDARIN LN, WINTER GARDEN, FL 34787
$405,000131 Days on yellowkey MLS ID: O6363767
REDUCED by $11,000 (2.6%) on 04/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1868 Built: 2017Monthly Fee: $347 Tax: $6,304 (2025)Community: Highlands/Summerlake Grvs #1Townhouse
Taxes:$6,304
Elementary School: Summerlake Elementary
Remarks: MASSIVE PRICE REDUCTION !! THIS PROPERTY IS LISTED OVER $10,000 BELOW CURRENT MARKET VALUE - SELLERS ARE HIGHLY MOTIVATED!! Look no further, this meticulously maintained townhouse checks all the boxes. Brand NEW ROOF (2025) and NEW CARPET with a 10-year WARRANTY makes this home feel brand new. Stainless steel kitchen appliances complete with a BOSCH DISHWASHER. the OPEN CONCEPT is inviting and there is a BONUS ROOM downstairs that could be used as an office, playroom, formal dining room, or sitting room. Enjoy the outdoors with an enclosed private courtyard. Rated one of the best neighborhoods in the country, Summerlake Groves, where small-town charm meets modern conveniences, TOP-RATED SCHOOLS and TOP-NOTCH RESORT-STYLE AMENITIES with the endless dining options, shopping and entertainment options of DISNEY & the booming HAMLIN TOWN CENTER less than 5 miles away! Location matters - this unit backs up to a quiet street not on a main road just a short walk to the community pool. At home you’ll enjoy LOW MAINTENANCE high-style living from your welcoming front porch to your private courtyard.
Listing is courtesy of: REAL LIVING R E SOLUTIONS (407-253-1377)
Listing Agent: Steven Tsukamoto (407-625-1027)
8024 BLUEJACK OAK DR, WINTER GARDEN, FL 34787
$490,000118 Days on yellowkey MLS ID: O6366553
2 Days Off yellowkey (back on 3/9/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1784 Built: 2018Monthly Fee: $312 Tax: $4,624 (2025)Community: SummerlakeTownhouse
Taxes:$4,624
Remarks: Welcome to this cozy and modern 3-bedroom, 2.5-bath townhouse located in the highly sought-after Summerlake community of Winter Garden. Featuring a well-designed split floor plan. Upstairs, the owner suite is a private retreat with a walk-in closet, dual sinks, a stand-up shower, and a separate garden tub, while the additional bedrooms are positioned on the opposite side for added privacy. The main level boasts a formal dining area, a spacious living or family room, and a beautifully appointed kitchen with, granite countertops, and ample prep space. A laundry closet upstairs adds extra convenience. Step outside to enjoy your paved, privately fenced courtyard, perfect for relaxing or entertaining, with easy access to the detached 2-car garage. The garage also offers a pull-down staircase that leads to extra storage in the attic with added subflooring. Just 7.6 miles from Magic Kingdom, with quick access to SR-429, this home offers a lifestyle filled with comfort, convenience, and everyday magic. Perfectly positioned with a lake view and direct access to the community’s exceptional amenities, you’ll enjoy tennis and basketball courts, a playground, boardwalk, clubhouse, resort-style pool, and fitness center—all just a short walk away. Situated directly behind Summerlake Elementary and the neighborhood park, the location is ideal for families. From your doorstep, take in the nightly Disney fireworks, enjoy front-row access to the community parade route, and embrace the sense of community Summerlake is known for. This home is just minutes from top-rated schools, Hamlin Town Center, Cinépolis Luxury Cinema, and Orange County National Golf Center. A rare opportunity to own a home that blends modern comfort with unmatched neighborhood charm—schedule your showing today!
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-891-1220)
Listing Agent: Rachael Connors (321-443-4475)
15381 HONEYBELL DR, WINTER GARDEN, FL 34787
$426,00017 Days on yellowkey MLS ID: O6391881
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2034 Built: 2016Monthly Fee: $418 Tax: $4,853 (2025)Community: Hamlin ReserveTownhouse
Taxes:$4,853
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Remarks: Live in the heart of Hamlin Reserve, this stylish executive townhome sits directly across from the community pool and playground, just a five-minute drive or short distance to Hamlin Town Center for convenient shopping, dining and everyday essentials in Horizon West. Spanning over 2,000 square feet, this four-bedroom, three-bath home with two-car garage and private patio is thoughtfully designed for comfortable, modern living. The main level features an open-concept layout with a guest bedroom and full bath, along with a well-appointed kitchen complete with a large granite island, stainless steel appliances and a spacious pantry, ideal for everyday living and entertaining. A private, partially covered courtyard offers a comfortable outdoor space and leads to an oversized rear-entry two-car garage. The second level features a split floor plan with three bedrooms, two full baths and a laundry room. Relax and unwind in the serene primary suite, complete with a private balcony offering picturesque views of the pool and playground, an ideal vantage point for nightly views of Walt Disney World fireworks. The primary suite also includes an en-suite bath with dual vanities, a glass-enclosed shower and a generously sized walk-in closet. Residents enjoy a maintenance-free lifestyle with HOA-covered exterior care, landscaping, roofing and access to resort-style amenities including a pool, clubhouse, playground, dog park and scenic green spaces, all just near your front door. Positioned near Hamlin Town Center, you’ll experience a vibrant, accessible community with boutique shopping, dining and entertainment, including Cinépolis Luxury Cinemas. With proximity to Orlando Health Horizon West Hospital, Orange County National Golf Center and Horizon West Regional Park, plus easy access to major highways, this home offers a balance of luxury, convenience and lifestyle in one of Central Florida’s sought-after communities. A 2016 roof (HOA maintains), 2016 air conditioner and 2026 water heater.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jj Mackle (321-217-9553)
11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$899,990115 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
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
$1,199,90035 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
$609,000289 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)
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