Location: Winter Garden
Keyword(s): West Orange High
Keyword(s) High School: West Orange High
Do Not Show Listings
2496 BARONSMEDE CT, WINTER GARDEN, FL 34787
$875,000Listed 06/26/2026 10:35AM MLS ID: G5114233
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4184 Built: 2002Monthly Fee: $210 Tax: $8,903 (2025)Community: Stoneybrook West 47/78Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,903
Elementary School: Whispering Oak Elem
High School: West Orange High
Tax Year: 2025
Middle School: SunRidge Middle
Remarks: Welcome home to 2496 Baronsmeade Ct Winter Garden situated in the much sought after golfing community of Stoneybrook West !!! This 4 Bedroom, 41/2 Bath pool home backing onto the golf course offers over 4,000sqft of living space with so many upgrades and 3 car garage with paved driveway. The tile ROOF was replaced in 2022, the AC's were replaced in 2021, kitchen and bathrooms fully renovated, new flooring throughout, all windows have custom vinyl shutters to keep the Florida heat out and save on utility bills. As you enter the home we have a formal living and dining area with built in wine bar, a huge open space with double story entry. The kitchen was fully remodled with a large center Island with Quartz countertops with waterfall edge. Lots of cabinet space and a walk in pantry, bar seating and breakfast nook. The kitchen over looks the great room wih vaulted ceilings and a gas fireplace as the focal part of the room. New sliding glass doors lead out to the huge screaned lanai with a salt water pool and spa and a built in BBQ that comes with the sale of the home. Plenty of space to enjoy the Florida lifestyle with a full sized bathroom. The Primary bedroom is downstairs and offers a large bedroom with bonus living space/home office/work out area, walk in closet and a renovated bathroom with dual vanities, large walk in shower and separate tub. Upstairs we have a enourmous loft space with built in desk space, ideal for home office/pool table/media/living space. There are 3 additional oversized bedrooms and 2 additional bathrooms to complete the upstairs. The laundry room is situated downstairs just off the garage. Stoneybrook West has so much to offer with a golf course, Restaurant, Fitness Center, Olympic Sized Swimming Pool, Playground, tennis courts, pickle ball, bastket ball and so much more. The low HOA fee covers Cable/Internet/Guarded gated community and access to all the amenities. Ideally located next to major HWYs, Disney, short commute to Orlando, Restaurants and shopping. This home has so much to offer with all the major upgrades already completed. Call today for your own private tour !!!
Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)
Listing Agent: Sarah Gholami (352-346-7857)
402 E MAPLE ST, WINTER GARDEN, FL 34787
$900,00015 Days on yellowkey MLS ID: O6412747
Bed: 6 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 2876 Built: 2021 Tax: $7,658 (2025)Community: East Garden Manor Add 03 RepSingle Family
Taxes:$7,658
Elementary School: Maxey Elem
Middle School: Lakeview Middle
Remarks: Coming Soon - An excellent opportunity for those seeking flexible living arrangements in two connected residences. Each side features the same floor plan and has been well maintained. This tour showcases the main residence. The adjoining residence offers a similar layout with its own unique décor, finishes, and upgrades. The design provides flexibility for a variety of living, guest, work-from-home, or ownership needs while maintaining a connected yet private setting.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: David Dorman (407-948-8295)
14252 CREEKBED CIR, WINTER GARDEN, FL 34787
$799,90016 Days on yellowkey MLS ID: O6408908
INCREASED by $900 (0.1%) on 06/17/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3572 Built: 2014Monthly Fee: $180Community: Bradford CreekSingle Family
Taxes:$0
Elementary School: SunRidge Elementary
Remarks: Welcome to 14252 Creekbed Circle, a spacious and beautifully designed home located in the heart of Winter Garden, in Bradford Creek, one of Central Florida's most sought-after communities. Perfectly situated near Downtown Winter Garden, you'll enjoy convenient access to popular restaurants, boutique shopping, farmers markets, community events, walking trails, and entertainment year-round. This expansive 4-bedroom, 3.5-bath residence offers plenty of room for everyone with a versatile floor plan designed for modern living. The oversized bonus room provides endless possibilities and can be used as a home office, game room, media room, playroom, fitness area, or additional living space to fit your needs. The spacious layout features generous living and dining areas, creating the perfect setting for entertaining guests or enjoying everyday life. The large kitchen with a center island for entertaining and an abundance of cabinets for all of your cooking needs. The private owner's suite offers a relaxing retreat, while the additional bedrooms provide comfort and flexibility for family and visitors. With abundant living space, a desirable location, and easy access to everything Winter Garden has to offer, this home combines convenience, functionality, and lifestyle in one exceptional package. Near Winter Garden Village, Disney and Advent Health in Winter Garden with easy access to 429/408 and the Turnpike. Don't miss the opportunity to make this your next home. Garage equipped with Tesla Charger, Upstairs HVAC replaced 8/2025, Downstairs HVAC replaced 1/2026, Dishwasher replaced 12/2024, Luxury Vinyl Plank flooring installed 12/2025 and new interior paint 5/2026.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Carla Robles (407-462-2347)
1646 HOLCOMB CREEK ST, WINTER GARDEN, FL 34787
$909,00089 Days on yellowkey MLS ID: O6394506
REDUCED by $20,000 (2.2%) on 06/17/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3841 Built: 2017Monthly Fee: $184 Tax: $12,543 (2025)Community: TwinwatersSingle Family
Taxes:$12,543
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: Welcome to 1646 Holcomb Creek Street. Your beautifully appointed five bedroom, 4.5-bath Meritage home offers 3,824 sq ft of thoughtfully designed living space in one of Winter Garden’s most desirable communities. Built in 2017, this energy-efficient floorplan features spray foam insulation, whole house water filtration system, a spacious open layout, high-end finishes, and multiple flexible living areas. The gourmet kitchen impresses with 42" cabinetry, quartz countertops, stainless steel appliances, extended storage, walk in pantry and a large eat-in dining area. The family room includes an electric fireplace with a floor-to-ceiling stone accent wall and triple sliding glass doors leading to the screened lanai and fenced backyard. The first-floor primary suite offers a tray ceiling and a spa-inspired bath with direct access to the laundry room. A guest suite with private bath, third bedroom with an additional private bath, powder room, and a convenient pocket office completes the main level. Upstairs, a large bonus/game room that provides endless possibilities for a media room, playroom or office, two additional bedrooms and a full bathroom. Your garage offers overhead storage and a Tesla-E/V charger. Exterior features include a tile roof, stone accents, extended front porch, in ground irrigation and lush landscaping. Located minutes from top-rated schools, shopping, dining, major highways and attractions. This exceptional home offers the perfect blend of luxury, comfort, and efficiency—move-in ready and meticulously maintained.
Listing is courtesy of: ERA GRIZZARD REAL ESTATE (407-203-5800)
Listing Agent: Jennifer Grimes (352-223-9588)
1101 EAGLES PASS WAY, WINTER GARDEN, FL 34787
$1,674,99939 Days on yellowkey MLS ID: O6408835
REDUCED by $25,000 (1.5%) on 06/22/2026
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4104 Built: 2023Monthly Fee: $203 Tax: $19,016 (2024)Community: Oakland ParkSingle Family
Taxes:$19,016
Elementary School: Tildenville Elem
Tax Year: 2024
Remarks: Virtually Staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36” dual-fuel range, warming oven, and a 48” side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner’s suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home’s charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Kevin Sullivan (321-663-3457)
721 S WOODLAND ST, WINTER GARDEN, FL 34787
$450,000Listed 06/26/2026 10:11AM MLS ID: O6419636
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1034 Built: 1955 Tax: $508 (2025)Community: Borders & Woosley SubSingle Family
Taxes:$508
Elementary School: Dillard Street Elem
Remarks: Located within Winter Garden’s golf cart district and just minutes from Plant Street, this property offers a distinctive combination of current residential use, C-2 General Commercial zoning, and no HOA. The single-story, concrete-block home includes 2 bedrooms, 1 bathroom, 1,034 square feet of heated living space, an enclosed porch that provides additional flexible space, and a roof replaced in 2023. The interior is ready for renovation, allowing the next owner to update the property according to their intended use and vision. Situated on an approximately 0.19-acre homesite, the property also features mature shade trees, a concrete driveway, and fenced sections of the yard. Its central Winter Garden location provides convenient access to the restaurants, shops, farmers market, community events, and West Orange Trail surrounding downtown and Plant Street, while nearby golf-cart-friendly roadways offer another way to explore the area. Whether considered for continued residential use, a renovation project, or a future business opportunity, this property presents a range of possibilities in a well-connected location. Buyers should independently verify all intended uses, permitting requirements, and zoning regulations with the City of Winter Garden.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Christopher Bessette (407-292-5400)
1830 BURDOCK DR, WINTER GARDEN, FL 34787
$725,000Listed 06/26/2026 9:12AM MLS ID: O6419559
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3435 Built: 2008Monthly Fee: $90 Tax: $6,900 (2025)Community: Carriage Pointe A-I & LSingle Family
Taxes:$6,900
Remarks: Virtually Staged. Lender Credit of 1% (of loan amount) toward closing costs or rate buy-down (inquire for more info). Welcome to CARRIAGE POINT, a GATED Winter Garden community offering an exceptional location and a thoughtfully designed floor plan. This two-story POOL home delivers the space today’s buyers crave, room for everyone, from dedicated home offices to flexible living and guest areas. With 3,435 square feet of living space, this home features five bedrooms, four full bathrooms, and a large bonus room. As you enter the home, you are welcomed by a spacious living room and dining room before continuing into the heart of the home. The open-concept kitchen features granite countertops, 42-inch cabinetry with crown molding, under-cabinet lighting, a gas range, an expanded pantry, and plenty of space for a breakfast table. The kitchen opens to the family room with sliding doors leading out to the SCREENED-IN POOL and FENCED backyard. The first floor features a desirable three-way split floor plan with four bedrooms and three full bathrooms. The spacious downstairs primary suite offers plenty of room to relax, along with a walk-in closet and private en-suite bathroom. Upstairs provides even more flexibility with a fifth bedroom, fourth full bathroom, and a large living area. Newer luxury vinyl plank flooring extends throughout the upstairs and staircase. The outdoor living space is a true highlight of this home with an expansive screened-in SALT WATER POOL ADDED IN 2021. Designed with both relaxation and fitness in mind, the pool features water jets giving a swim-against-the-current feature, creating the perfect space to enjoy a refreshing swim or get in a low-impact workout. Carriage Pointe offers residents a variety of community amenities including a tennis court, playground, soccer field, and walking path. For those who enjoy an active lifestyle, the area offers miles of scenic trails, including the West Orange Trail, along with parks and outdoor activities nearby. The location is ideal, with convenient access to State Road 429 and Highway 50, making travel throughout Central Florida easy. Enjoy being close to Winter Garden Village, the Hamlin area, restaurants, shopping, entertainment, and AdventHealth Winter Garden. Families will appreciate the HIGHLY RATED SCHOOLS, including Whispering Oak Elementary, Hamlin Middle School, and West Orange High School. Historic Downtown Winter Garden is less than five miles away and offers charming shops, local restaurants, the weekly farmers market, the West Orange Trail, and year-round community events. Additional features include a three-car garage, natural gas service through Lake Apopka Natural Gas District, gas washer and dryer, a 2020 water heater, updated electrical service, and added electrical for a built-in microwave. With its exceptional floor plan, private pool, flexible living spaces, and prime Winter Garden location, this Carriage Pointe home offers exceptional space, comfort, and convenience. Schedule your private tour today!
Listing is courtesy of: EXP REALTY LLC (407-305-4300)
Listing Agent: Justin Core (407-305-4300)
1144 HULL ISLAND DR, WINTER GARDEN, FL 34787
$1,799,000Listed 06/25/2026 4:09PM MLS ID: O6418306
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4102 Built: 2021Monthly Fee: $165 Tax: $13,885 (2025)Community: Hull Island/OaklandSpa: YesSingle Family
Taxes:$13,885
Remarks: Welcome to this exceptional lakefront retreat on the shores of Lake Apopka, where breathtaking water views, luxury upgrades, and exceptional outdoor living come together to create the ultimate Florida lifestyle. Offering 5 bedrooms, 4.5 bathrooms, and over 4,000 square feet of thoughtfully designed living space, including a convenient first-floor bedroom, this beautifully updated residence showcases more than $500,000 in improvements, creating a move-in-ready experience for the next owner. From the moment you arrive, you'll appreciate the extensive upgrades throughout the home, including porcelain tile throughout the main living areas on the first floor, engineered white oak hardwood flooring throughout the second level, a custom wood and iron staircase, upgraded cabinetry, quartz countertops, designer finishes, and a beautifully appointed kitchen featuring premium KitchenAid appliances, a gas cooktop, and custom soft-close cabinetry. Designed for both everyday living and entertaining, the backyard is a true showpiece. Enjoy a resort-style saltwater pool and spa, gas-heated for year-round enjoyment, expansive outdoor living areas, and a fully equipped summer kitchen featuring premium Blaze appliances. Electric screens allow you to enjoy outdoor dining and entertaining comfortably while taking in the peaceful lakefront setting and stunning sunset views. Boating enthusiasts will appreciate the private dock complete with a 5,000-pound boat lift, offering direct access to Lake Apopka, one of Florida's largest lakes. With more than 30,000 acres of open water to explore, the lake offers endless opportunities for boating, fishing, watersports, and unforgettable sunset cruises. Known for its trophy bass fishing, abundant wildlife, and expansive waterfront views, Lake Apopka provides a rare opportunity to enjoy true lakefront living with the freedom and space that few Central Florida lakes can offer. This property delivers the waterfront lifestyle Florida is known for. Additional highlights include a convenient first-floor bedroom, a second-floor laundry room, solar panels that will be paid off at closing, natural gas service, a Culligan water filtration system, dual pool pumps, and city sewer, a significant advantage for a waterfront property. Ideally located just minutes from Downtown Winter Garden, shopping, dining, and major roadways, this exceptional lakefront residence offers the perfect balance of luxury, recreation, and everyday convenience.
Listing is courtesy of: ALIGN REAL ESTATE LLC (305-389-2922)
Listing Agent: Tiffany Pantozzi (407-955-9716)
16614 HARBOR SAIL WAY, WINTER GARDEN, FL 34787
$1,495,00018 Days on yellowkey MLS ID: O6414639
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4882 Built: 2016Monthly Fee: $168 Tax: $11,216 (2025)Community: Waterside/Johns Lake Ph 1Spa: YesSingle Family
Taxes:$11,216
Remarks: An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining. While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life. The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary. Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the entire home. While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets. Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center and community pool. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping. This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.
Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)
Listing Agent: Garry Walmsley (407-923-2134)
107 TRADITIONS DR, WINTER GARDEN, FL 34787
$444,975101 Days on yellowkey MLS ID: S5145650
REDUCED by $10,000 (2.2%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1582 Built: 1999Monthly Fee: $45 Tax: $1,458 (2024)Community: Traditions SubSingle Family
Taxes:$1,458
Remarks: You found it with this Location! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Private / separate laundry room. Separate office or workshop in garage is UNDER AIR UNDER & perfect for the handyman! The backyard is fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Rick Evans, Ii (407-538-9295)
397 ERON WAY #42, WINTER GARDEN, FL 34787
$225,000Listed 06/25/2026 4:30PM MLS ID: O6420092
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 930 Built: 1988Monthly Fee: $424 Tax: $276 (2025)Community: Townhomes Winter GardenCondo
Taxes:$276
Remarks: Virtually Staged. Welcome to one of the cutest townhomes in the heart of Downtown Winter Garden! This charming 3 Bedroom, 2 bath home offers the perfect blend of comfort, covenience and one of Central Florida's most sought-after lifestyles. Whether you're a first-time homebuyer, looking to downsize or searching for a fantastic investment opportunity, this home checks all the boxes. Inside, you'll find a functional floor plan with comfortable living spaces, spacious bedrooms and low-maintenance living so you can spend more time enjoying everything the area has to offer. Location is everything, and this one is hard to beat! Just minutes from the award-winning Historic Downtown Winter Garden, you'll love spending weekends exploring the nationally recognized Winter Garden Farmers Market, browsing unique boutiques, enjoying locally owned restaurants, coffee shops, breweries and year-round community events. Living here means embracing the famous Golf Cart District lifestyle. Hop in your golf cart and head downtown for dinner, live music, festivals or an evening stroll along Plant Street. Outdoor enthusiasts will appreciate easy access to the scenic West Orange Trail, offering miles of paved paths for walking, running and biking. Winter Garden continues to be one of Central Florida's most desirable communities thanks to its small-town charm, top-rated amenities, vibrant downtown, and convenient access to major highways, Orlando, world-famous attractions, shopping, dining and entertainment. Whether you're looking for a place to call home or an income-producing property in a highly desirable location, this adorable townhome offers incredible value and endless potential. Don't miss your opportunity to own a piece of the Downtown Winter Garden lifestyle! Schedule your private showing today and discover why so many people are proud to call Winter Garden home.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
15340 OAK APPLE COURT CT #16B, WINTER GARDEN, FL 34787
$350,0001 Day on yellowkey MLS ID: O6419809
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1544 Built: 2008Monthly Fee: $282 Tax: $4,127 (2025)Community: Tucker Oaks Condo Ph 4Condo
Taxes:$4,127
Remarks: Welcome to Tucker Oaks, one of Winter Garden's most desirable gated communities! This beautifully maintained 3-bedroom, 2.5-bathroom townhome-style condo offers 1,544 square feet of comfortable living space, an attached two-car garage providing secure parking and additional storage, and a prime location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright and inviting interior featuring laminate flooring installed throughout the living areas and bedrooms, complemented by ceramic tile in the kitchen and bathrooms. Fresh interior paint creates a clean, modern feel, while crown molding adds an elegant touch to the main living area. The well-appointed kitchen is designed for both style and function, featuring granite countertops, 42-inch cabinetry, updated countertops, a new kitchen sink, decorative backsplash, and an abundance of workspace. A huge under-stair storage area provides valuable extra storage rarely found in similar homes. Upstairs, all three bedrooms are thoughtfully positioned for privacy. The spacious primary suite features crown molding, an en-suite bath and ample closet space, while two additional bedrooms offer flexibility for family, guests, or a home office. Additional upgrades and features include a recently replaced A/C system (2021), washer and dryer (2024).Residents of Tucker Oaks enjoy access to a community pool and low-maintenance living in a peaceful setting. Ideally located just 1.4 miles from Historic Downtown Winter Garden and the popular Plant Street Market, you'll enjoy easy access to boutique shopping, dining, entertainment, farmers markets, and year-round community events. Outdoor enthusiasts will appreciate the nearby West Orange Trail, Oakland Nature Preserve, and Oakland Arts & Heritage Center. Commuters will love the quick access to Florida's Turnpike and major highways, while the new Costco in Clermont adds even more convenience.Move-in ready and meticulously cared for, this exceptional home offers the perfect combination of comfort, convenience, and location. Schedule your private showing today!
Listing is courtesy of: COLEDEV REAL ESTATE LLC (407-915-0456)
Listing Agent: Aileen Frauman (407-928-0211)
16707 SANCTUARY DR, WINTER GARDEN, FL 34787
$717,0001 Day on yellowkey MLS ID: O6419784
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2516 Built: 2020Monthly Fee: $165Community: Sanctuary/Twin WatersSingle Family
Remarks: Welcome home to Sanctuary at Twin Waters — one of Winter Garden's most sought-after communities! This beautifully designed 2020-built home offers soaring high ceilings, tile throughout, and a wide open floor plan that instantly makes you feel at home. The heart of the home is the stunning kitchen, featuring a massive island with rich granite countertops and gorgeous 42-inch Espresso cabinets — perfect for gathering and entertaining. Whether it's a casual morning in the eat-in nook or a formal dinner with guests, this home was built for making memories. With a versatile bonus room and a luxurious owner's retreat tucked away in the back for ultimate privacy, there is space to truly live. The spa-like ensuite features a soaker tub, subway-tiled shower, dual sinks with quartz counters, and a generous walk-in closet — your own personal sanctuary at the end of every day. Even the water feels different here, thanks to a whole-home purification system. A rare find in Central Florida — this is a gas community, adding both value and everyday convenience. The garage features a mini split AC unit, keeping the space cool and comfortable year-round — perfect for a workshop, home gym, or hobby space. Step outside to your fully fenced, spacious corner lot with a covered porch and plenty of room to add your dream pool. The community itself offers so much to love — a pool, fishing dock, playground, and picnic area, plus breathtaking views of Lake Avalon right in the neighborhood. This is more than a home — it's the lifestyle you've been waiting for. Come see it and stay forever.
Listing is courtesy of: YOUR HOME SOLD GUARANTEED REALTY (407-566-2555)
Listing Agent: Laura Petersen (407-566-2555)
914 TROWMAN ALY, WINTER GARDEN, FL 34787
$649,00031 Days on yellowkey MLS ID: O6410871
REDUCED by $26,000 (3.9%) on 06/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1642 Built: 2022Monthly Fee: $356 Tax: $6,421 (2025)Community: Oakland ParkSingle Family
Taxes:$6,421
Remarks: Virtually Staged. Nestled in the highly sought-after Oakland Park community, this beautifully maintained 3-bedroom, 3-bath home is the definition of move-in ready living. Featuring desirable upgrades throughout, including gas appliances, elegant plantation shutters, and a turnkey design, this home offers the perfect blend of comfort, style, and convenience. Enjoy open-concept living spaces filled with natural light, spacious bedrooms, and a layout designed for modern living and entertaining. Pride of ownership shines in every detail, making this home truly stand out. Located in a charming golf cart community with resort-style amenities, residents enjoy access to parks, schools, walking trails, and more. Just minutes from vibrant Downtown Winter Garden, you'll love being close to the award-winning farmers market, lively festivals, boutique shopping, dining, and entertainment. This is your opportunity to own a well-maintained, upgraded home in one of Winter Garden's most desirable communities!
33 TIMBERCREEK PINES CIR, WINTER GARDEN, FL 34787
$545,00036 Days on yellowkey MLS ID: O6408941
REDUCED by $10,000 (1.8%) on 06/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1584 Built: 2004Monthly Fee: $46 Tax: $7,326 (2025)Community: Timbercreek Pines A B C & DSingle Family
Taxes:$7,326
Remarks: Welcome to this beautifully renovated single-story gem nestled in the heart of Historic Winter Garden, one of Central Florida’s most sought-after communities. Perfectly situated just two blocks from vibrant downtown Winter Garden and iconic Plant Street, this home offers the ultimate blend of historic charm, modern luxury, and walkable convenience. Located within the highly desirable golf cart district and just moments from the renowned West Orange Trail, you’ll enjoy easy access to cobblestone streets, boutique shopping, coffee houses, award-winning restaurants, and the beloved Saturday Farmer’s Market — all right outside your door. Completely renovated from top to bottom, inside and out, this move-in ready home showcases exceptional attention to detail and thoughtful upgrades throughout. Step inside to discover a bright open floor plan enhanced by luxury vinyl plank flooring, upgraded 6-inch baseboards, updated light fixtures, neutral designer finishes, and ceiling fans in every bedroom. The stunning remodeled kitchen serves as the heart of the home, featuring crisp white cabinetry, elegant quartz countertops, modern backsplash, dark designer hardware, LED lighting, stainless appliances, and an oversized island with seating for six — perfect for entertaining family and friends. The bathrooms have been tastefully updated to blend timeless character with modern functionality, while the inside laundry room and abundant storage, including two hallway closets near the secondary bedrooms, add everyday convenience. Outdoor living shines with a newly added tiled screened lanai complete with new sliding doors and windows that create seamless indoor-outdoor flow. The expansive fenced backyard is a private oasis featuring fresh landscaping, a Magnolia tree, Orange tree, and Avocado tree — the perfect setting to relax and enjoy Florida living year-round. Additional highlights include a brand-new AC unit, anti-slip garage floor coating, and a 6-foot white vinyl privacy fence. This one-of-a-kind home perfectly captures the charm of Historic Winter Garden while offering the modern updates today’s buyers desire. WELCOME HOME.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Peyton Blanton (407-462-7891)
233 SOUTHERN PECAN CIR #101, WINTER GARDEN, FL 34787
$249,90092 Days on yellowkey MLS ID: S5144851
REDUCED by $3,000 (1.2%) on 06/24/2026
Bed: 2 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 966 Built: 2005Monthly Fee: $343 Tax: $2,537 (2024)Community: Southern Pines CondoCondo
Taxes:$2,537
Remarks: Welcome to this beautifully remodeled 2-bedroom, 1-bath condo with an attached garage. Move right into this stunning corner unit. This light-filled home has been thoughtfully updated throughout with fresh paint and brand-new flooring, and modern finishes that create a clean, contemporary feel. Residents enjoy access to an impressive array of resort-style community amenities, including. Swimming pool with a relaxing hot tub spa, fully equipped fitness center, indoor basketball and racquetball court, tennis court, and a convenient car wash area. Whether you're looking for your next home or a great investment opportunity, this beautifully updated condo combines comfort, style, and exceptional amenities in one attractive package. New A/C was installed on June 11, 2026
Listing is courtesy of: HOMESMART (407-476-0451)
Listing Agent: Maria Lloret (407-929-1994)
483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787
$339,90073 Days on yellowkey MLS ID: O6398208
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1988 Tax: $2,702 (2025)Community: East Garden Manor Add 03Single Family
Taxes:$2,702
Remarks: Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roff, new pluming, close to major roads, schools, minutes to Winter Garden dawn town.
Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)
Listing Agent: Rosa Rodriguez (407-832-1185)
1701 E BAY ST, WINTER GARDEN, FL 34787
$295,00020 Days on yellowkey MLS ID: O6413973
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 825 Built: 1950 Tax: $2,560 (2025)Community: Joe Louis Park First AddSingle Family
Taxes:$2,560
Remarks: Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden. Blending modern updates with timeless charm, this move-in-ready residence offers stylish finishes, functional living spaces, and a convenient location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright, refreshed interior featuring contemporary flooring, recessed lighting, updated fixtures, and an open, inviting atmosphere. The fully remodeled kitchen showcases elegant white shaker cabinetry, sleek countertops, stainless steel appliances, and modern hardware, creating a clean and sophisticated space for everyday living and entertaining. The renovated bathrooms feature designer-inspired finishes, including a spacious walk-in shower with stunning marble-look tile, upgraded fixtures, and a modern vanity. Thoughtful updates throughout the home provide a fresh, cohesive look while maintaining comfort and functionality. Outside, enjoy a spacious lot shaded by mature trees, offering room for outdoor entertaining, gardening, pets, or future expansion. Fresh exterior improvements and landscaping enhance the home's curb appeal, while the absence of HOA restrictions provides added flexibility and freedom. Conveniently located near shopping, dining, parks, the West Orange Trail, major highways, and all that Downtown Winter Garden has to offer, this turnkey property presents an exceptional opportunity for homeowners and investors alike. Don't miss your chance to own a beautifully updated home in one of Central Florida's most sought-after communities.
638 AUTUMN OAKS LOOP, WINTER GARDEN, FL 34787
$594,00015 Days on yellowkey MLS ID: G5113531
REDUCED by $26,000 (4.2%) on 06/18/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2044 Built: 2005Monthly Fee: $146 Tax: $3,096 (2025)Community: Winter OaksSpa: NoSingle Family
Taxes:$3,096
Remarks: Experience the quintessential Winter Garden lifestyle in this exceptional 3 bedroom/2.5 bathroom home, perfectly positioned within the highly sought-after Golf Cart District. This residence offers a rare park-side setting, providing picturesque views of majestic oaks with green space. For those who enjoy active community life, you are just steps away from the neighborhood pool and playground. Just a few minutes away from Downtown Winter Garden! Exceptional Curb Appeal & Interior Elegance: from the moment you arrive, the covered front porch welcomes you with outdoor column lights, coach lights, landscaping and a framed transom over the front door. The first-floor features stylish Bahama shutters, formal living room with a double paddle ceiling fan, spacious dining area, a family room that features a gas fireplace, with tile flooring, engineered wood floors and LVP throughout the first floor. Chef-Inspired Kitchen : The heart of the home is the kitchen, which has been upgraded from an electric to a gas stove and features a redesigned pantry to maximize storage. You will also find under-cabinet lighting and modern lighting. Primary suite: The 1st floor Primary Bedroom suite serves as a private sanctuary with new flooring throughout the bedroom, closet, and bathroom, as well as a completely remodeled primary bathroom. The second story split floor plan: The transition to the second floor is highlighted by a staircase and balcony where traditional wood newels have been replaced with elegant rod iron. The second story features 2 spacious bedrooms , a full sized guest bathroom and at center stage of the upstairs landing is a bonus area for additional lounging area/home office or play area. Outdoor Oasis: Step outside to your private retreat: a rear enclosed screened-in room that perfectly encompasses the lanai and soaker pool area. The outdoor space is further enhanced by: An extended patio deck around the pool, a new fan on the lanai for year-round comfort, a rebuilt pool pump with pool equipment housing, a new fence with a leveled concrete retaining wall base, accented by fence and landscape lighting. Systems & StorageSolutions: This home offers incredible peace of mind with a new roof (installed 11/2020) and a brand-new AC system (3 weeks old) with a transferable warranty. Storage is a priority here, with a garage featuring built-in file cabinets, recessed ceiling lights, shelves, appliance storage, and overhead shelving, plus additional attic storage. Functional extras include a built-in wall safe, a generator pad, and a security camera at the rear of the home. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Lorie Gullian (407-928-8078)
14755 MASTHEAD LANDING CIR, WINTER GARDEN, FL 34787
$575,00043 Days on yellowkey MLS ID: O6408082
REDUCED by $5,000 (0.9%) on 06/25/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2258 Built: 2004Monthly Fee: $253 Tax: $8,397 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$8,397
Remarks: Located in the highly desirable Stoneybrook West community, this beautifully maintained 4-bedroom, 2-bath home offers the perfect blend on comfort, style, and convenience. Featuring a newer roof installed in 2019, brand-new 2025 central air conditioning system, newer refrigerator, new range/oven, and new dishwasher. The home welcomes you with abundant natural light, an open concept layout, and spacious living areas enhanced by attractive laminate flooring throughout. One of the home's standout features is the serene pond view from the screened lanai. With four bedrooms and versatile living spaces, this home easily accommodates families of all sizes.
Listing is courtesy of: SUSANA JORDAN STUTSMAN (321-278-0334)
Listing Agent: Susana Stutsman (321-278-0334)
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