Displaying: For Sale
Location: Winter Garden
Property Type(s): Single Family
Living Area Square Feet: 2500 to 2999
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Winter Garden - 155 properties found
15591 GENTLE RAIN DR, WINTER GARDEN, FL 34787
$730,00026 Days on yellowkey MLS ID: O6411803
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2896 Built: 2025Monthly Fee: $99 Tax: $1,890 (2025)Community: Osprey Ranch Ph 1Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,890
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: Welcome to this beautifully upgraded home in Winter Garden, where style, comfort, and thoughtful design come together seamlessly. From the moment you step inside, you’re greeted by an open, bright, and airy layout, enhanced by elegant farmhouse-inspired finishes and abundant natural light throughout. The main home features no carpet, creating a clean and modern aesthetic, while stunning custom built-in cabinetry in the kitchen, living room, and bedrooms adds both sophistication and functionality. At the center of the home, the spacious kitchen is designed to impress, featuring a large island perfect for entertaining, elegant finishes, and seamless flow into the living and dining spaces. Every detail has been thoughtfully selected, and with tons of upgrades throughout, this home feels elevated at every turn. One of the standout features is the private studio above the garage, ideal for guests, extended family, a home office. Located in the desirable Osprey Ranch community, this home is just minutes from Walt Disney World and everyday conveniences. Even better, you are just steps from the resort style amenities, including the community pool, splash pad, cabana, and playground, offering the perfect blend of lifestyle, convenience, and community living.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Carolina Fortes Ribeiro (407-956-7674)
15143 KIRSTY ALY, WINTER GARDEN, FL 34787
$654,900280 Days on yellowkey MLS ID: O6344886
REDUCED by $4,100 (0.6%) on 05/24/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2934 Built: 2017Monthly Fee: $328 Tax: $9,868 (2025)Community: Overlook 2/Hamlin Ph 2 & 5Single Family
Taxes:$9,868
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Welcome to this beautifully maintained 5-bedroom, 3.5-bathroom move in ready home, ideally situated on a desirable corner lot in the heart of Hamlin, Winter Garden. With a thoughtfully designed layout, this home features one bedroom on the main floor—perfect for guests or multi generational living—and three additional bedrooms upstairs, offering plenty of space and privacy for the whole family. The home boasts soaring open ceilings that create a bright, airy atmosphere throughout. The upgraded kitchen is a true highlight, featuring modern finishes, high-end appliances, and ample space for cooking and entertaining. Adding even more value is the detached mother-in-law suite, offering flexibility for extended family, a private office, or rental income potential. Recently repainted exterior, elegant plantation shutters throughout the entire home, upgraded carpet, screen enclosure, upgraded 8 feet door downstair and upstairs, and the advantage of a spacious corner lot offering extra privacy and curb appeal. Located just minutes from top-rated schools, shopping, dining, and entertainment, this home perfectly combines luxury, functionality, and location in one of Winter Garden’s most sought-after communities.
Listing is courtesy of: ARION REALTY (407-564-8888)
Listing Agent: Jin Cheng (561-346-5225)
5443 BOWMAN DR, WINTER GARDEN, FL 34787
$649,00037 Days on yellowkey MLS ID: O6408812
0 Days Off yellowkey (back on 5/29/2026)
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2656 Built: 2015Monthly Fee: $339 Tax: $7,564 (2025)Community: Overlook 2/HamlinSpa: NoSingle Family
Taxes:$7,564
Remarks: Under contract-accepting backup offers. Luxury lakeview living with private apartment above the garage. Welcome to your dream home, where luxury, comfort and thoughtful design come together in one of Hamlin’s sought-after communities. This exceptional residence features four spacious bedrooms, each with its own en-suite bath on the second floor, including one bedroom with en-suite bath conveniently on the first floor, plus an additional half bath for guest convenience. A standout feature is the desirable private Next Gen suite above the garage, offering incredible flexibility for multigenerational living, extended guests, a home office or potential rental income. Enjoy peaceful water views that create the perfect backdrop for both relaxing mornings and beautiful Florida sunsets. In a top-rated A-rated school district, this home offers not only luxury living but also outstanding educational opportunities. Enjoy a walkable lifestyle with direct access to dining, cafés, boutique shopping, fitness studios, parks and entertainment all nearby. This vibrant, growing community offers unmatched convenience and everyday enjoyment right outside your doorstep. More than just a home, this is a place where neighbors become friends and lasting memories are made in one of Central Florida's desirable areas. Schedule your private showing today and experience it for yourself!
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Carolina Medeiros (305-753-1943)
1209 CASTLEPORT RD, WINTER GARDEN, FL 34787
$659,000102 Days on yellowkey MLS ID: O6390760
REDUCED by $5,900 (0.9%) on 05/29/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2812 Built: 2001Monthly Fee: $243 Tax: $4,030 (2025)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$4,030
Elementary School: Whispering Oak Elem
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Welcome to 1209 Castleport Rd — your next chapter in Stoneybrooke West, a gorgeous golf-course community where everyday feels like a getaway. From the moment you arrive you’ll love the manicured fairways, peaceful walking paths, and neighborhood pride that make this community stand out. Step inside and imagine family mornings and movie nights in the bright, open living spaces. This home offers 5 spacious bedrooms and 3 full bathrooms — plenty of room for guests, a home office, or a hobby room. Thoughtful finishes and flexible room spaces make entertaining effortless and daily life comfortable. Location is everything: you’re minutes from theme parks, with fast highway connections for stress-free commutes and weekend escapes, plus easy access to shopping, dining, and services. Whether you’re teeing off on the greens, grabbing dinner nearby, or heading out for a day at the parks, 1209 Castleport Rd combines comfort, convenience, and that warm, community feel you’ve been looking for.
Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)
Listing Agent: Angela Magac (407-744-5557)
15043 PIGEON PLUM LN, WINTER GARDEN, FL 34787
$594,000136 Days on yellowkey MLS ID: S5143009
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2695 Built: 2016Monthly Fee: $241 Tax: $8,470 (2024)Community: Summerlake Pd Ph 2C 2D 2ESingle Family
Taxes:$8,470
Elementary School: Summerlake Elementary
Tax Year: 2024
Middle School: Hamlin Middle
Remarks: Welcome to this beautifully maintained 4-bedroom, 3.5-bath home located in the desirable Winter Garden area. This spacious residence offers a well-designed floor plan with generous living areas, ideal for both everyday living and entertaining. The home features a bright and open layout with abundant natural light, a large kitchen with ample cabinetry and counter space, and a seamless flow into the dining and living areas. The primary suite offers a private retreat with an en-suite bathroom and walk-in closet. Upstairs and/or additional bedrooms provide flexibility for guests, a home office, or multigenerational living. The 3.5 bathrooms ensure comfort and convenience for family and visitors alike. Enjoy outdoor living with a private backyard space perfect for relaxing or hosting gatherings. Conveniently located near major highways, shopping, dining, and entertainment, this property offers easy access to everything Winter Garden, and surrounding areas.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ceila Morales (888-883-8509)
14345 WABASSO LOOP, WINTER GARDEN, FL 34787
$735,000139 Days on yellowkey MLS ID: O6376609
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2878 Built: 2022Monthly Fee: $192 Tax: $10,615 (2025)Community: Tilden Place/Winter GardenSingle Family
Taxes:$10,615
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Remarks: Located within the gated community of Tilden Place, this thoughtfully designed home offers exceptional flexibility and everyday comfort in one of Winter Garden’s most convenient locations. The main level features a private primary suite along with three additional bedrooms, including an en suite option ideal for guests, multigenerational living, or a home office. Upstairs, a spacious loft, bedroom, and full bath create a separate retreat perfect for teens, visitors, or work-from-home needs. Light-filled living and dining areas flow into the kitchen, which is well-appointed with a gas range, double ovens, generous counter space, a walk-in pantry, and breakfast bar—designed to support both everyday living and effortless entertaining. Sliding doors open to a screened porch, extending the living space outdoors for relaxed mornings and evenings. Enjoy close proximity to A-rated schools, including Keene’s Crossing, Bridgewater Middle, Windermere High, and nearby Foundation Academy. Just minutes from downtown Winter Garden, the West Orange Trail, shopping, dining, and daily conveniences, with easy access to SR 429, Orlando International Airport, and the attractions Central Florida is known for.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Hilary Hall (407-902-9311)
18309 OLIVER TWIST WAY, WINTER GARDEN, FL 34787
$725,000118 Days on yellowkey MLS ID: O6386008
0 Days Off yellowkey (back on 5/27/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2832 Built: 2023Monthly Fee: $281 Tax: $497 (2024)Community: Waterleigh Ph 4B & 4CSingle Family
Taxes:$497
Remarks: Welcome to 18309 Oliver Twist Way, a beautifully maintained five bedroom, four bathroom home located in the highly sought after Waterleigh community in Winter Garden. Designed for both everyday comfort and effortless entertaining, this spacious home offers a thoughtful layout with flexible living spaces and modern finishes throughout. One of the standout features is the private downstairs guest ensuite, ideal for multigenerational living, visiting family, or a dedicated office space. The open concept main living area creates a warm and inviting atmosphere, seamlessly connecting the kitchen, dining, and living spaces while offering plenty of natural light. Upstairs, generously sized bedrooms provide space for everyone, while the primary suite serves as a peaceful retreat after a long day. Every detail has been carefully maintained, making this home truly move in ready.nLocated within Waterleigh, residents enjoy access to resort style amenities including multiple pools, walking trails, fitness centers, playgrounds, and community green spaces. The home is also conveniently positioned near local schools, shopping, dining, and just a short drive to Walt Disney World, offering both convenience and lifestyle. If you are looking for a home that blends space, functionality, and the vibrant community feel that Waterleigh is known for, this is one you will not want to miss.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Kerstin Crow (615-428-7046)
15852 SHOREBIRD LN, WINTER GARDEN, FL 34787
$799,000217 Days on yellowkey MLS ID: O6361580
INCREASED by $14,000 (1.8%) on 05/24/2026
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2766 Built: 2019Monthly Fee: $385 Tax: $10,928 (2024)Community: Lakeshore Preserve Ph 5Single Family
Taxes:$10,928
Elementary School: Hamlin Elementary
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. Stunning 2-Story Home in Winter Garden – 4 Bedrooms, Solar Panels, and Exceptional Features This beautiful two-story home in the highly sought-after Winter Garden neighborhood offers everything you need for luxury living and modern convenience. With 4 spacious bedrooms, including a luxurious master suite complete with a walk-in closet, this home is designed to provide comfort and style for every member of the family. The additional three bedrooms are equipped with ample built-in closets, perfect for all your storage needs. The home boasts 4 full bathrooms and an additional half bathroom, ensuring convenience and privacy for all. The open floorplan seamlessly connects the expansive great room and formal dining area, creating an ideal space for both everyday living and entertaining. The kitchen is a chef’s dream, featuring beautiful solid wood cabinets, sleek stone countertops, and top-of-the-line appliances that are included with the home. Step outside to enjoy Florida's beautiful weather on the front porch, or retreat to the private backyard with an outdoor kitchen and spacious patio – perfect for relaxing, grilling, and entertaining guests. The home is also equipped with solar panels, making it energy-efficient and helping to lower utility costs. Additional features include a 2-car attached garage, providing plenty of space for vehicles and storage, and a prime location near major roadways and top-rated schools, offering the perfect balance of privacy and accessibility. This home truly has it all – don’t miss the opportunity to make it yours! Please note: The solar panel financing is $90.00 per month, offering long-term savings on energy costs.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Joao Freitas De Souza Freitas, Jr (407-342-6363)
11271 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$869,99656 Days on yellowkey MLS ID: O6403252
3 Days Off yellowkey (back on 5/27/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2866 Built: 2025Monthly Fee: $199 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Elementary School: None
High School: None
Middle School: None
Remarks: Under Construction. Waterleigh presents the Cresswell. This two-story all concrete block construction single-family home features 5 bedrooms and 4 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find the 5th bedroom along with a full bathroom. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Cresswell includes a Home is Connected smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
7580 SPRING VALLEY ST, WINTER GARDEN, FL 34787
$693,23061 Days on yellowkey MLS ID: G5111519
0 Days Off yellowkey (back on 4/24/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2515 Built: 2026Monthly Fee: $122Community: Hamlin Meadows At HamlinSingle Family
Taxes:$0
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE PRE DESIGN CENTER PRICING The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model by Dream Finders Homes. This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 17' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with a walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location. Enjoy being minutes away from the vibrant Hamlin Town Center and major expressways.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
912 LANDRUM DR, WINTER GARDEN, FL 34787
$1,300,00042 Days on yellowkey MLS ID: O6407616
0 Days Off yellowkey (back on 5/26/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2834 Built: 2024Monthly Fee: $208 Tax: $13,517 (2025)Community: Oakland ParkSingle Family
Taxes:$13,517
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Welcome to your new dream home! Built by J&J Building and located in one of Central Florida’s most sought-after communities, this stunning 4-bedroom, 3-bath custom home in Oakland Park offers elevated design, thoughtful upgrades, and a lifestyle that blends luxury with everyday convenience. From the manicured front lawn to the spacious covered front porch, every detail creates an unforgettable first impression. Step inside to a breathtaking foyer and staircase landing where custom trim-accented walls, crown molding and designer light fixtures immediately set the tone for the craftsmanship found throughout the home. The open-concept design seamlessly connects the living, dining, and kitchen spaces, creating an effortless flow perfect for entertaining and everyday living. The kitchen is truly a chef’s dream, featuring a large center island, stunning range with a custom-crafted hood, Casablanca white tile backsplash, Fisher & Paykel panel-ready refrigerator, built-in wine bar, abundant storage, and a spacious walk-in pantry. Natural gas service powers both the cook top and tank-less water heater, adding both efficiency and elevated functionality. The dining area makes a bold statement with its designer wallpaper accent wall and striking light fixture, creating a memorable setting for intimate dinners and lively gatherings alike. Just beyond, the living room offers a warm and inviting atmosphere with abundant natural light and a beautiful fireplace with mantle detail. A first-floor bedroom and full bath provide ideal privacy for guests or multi-generational living. Upstairs, additional bedrooms are generously sized with abundant natural light and storage, while the primary suite offers a luxurious private retreat. Crown molding enhances the space, while the oversized custom walk-in closet provides exceptional organization. The spa-inspired en-suite bath features two separate vanities, a stunning freestanding soaking tub, and a spacious walk-in shower designed for ultimate relaxation. Outdoor living is just as impressive. The screened and covered lanai creates the perfect setting for al fresco dining or enjoying Florida’s beautiful weather year-round. Pre-wiring for outdoor speakers extends the entertainment potential, while the fenced backyard offers peace of mind for four legged friends and play. Additional thoughtful upgrades include keyless patio entry, an expanded pavered driveway leading to a detached two-car garage, a Tonal Home Gym in the garage, plus dedicated outlets for both golf cart and EV charging. Life in Oakland Park offers an unmatched lifestyle, with the West Orange Fitness Trail running through the center of the community and downtown Winter Garden’s renowned Plant Street just a short golf cart ride away. Residents enjoy access to two resort-style pools, a clubhouse, parks, walking trails, a dog park, and a full calendar of community events, all with quick access to the Florida Turnpike for effortless commuting. This home puts you in the heart of a thriving community, with everything you could need close by. Don't miss out on this amazing home, schedule your private showing TODAY!!
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Lenee Magnuson (407-902-4488)
15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787
$579,90070 Days on yellowkey MLS ID: O6396640
1 Days Off yellowkey (back on 5/5/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2626 Built: 2013Monthly Fee: $128 Tax: $6,746 (2025)Community: Johns Lake Pointe A & SSingle Family
Taxes:$6,746
Remarks: Under contract-accepting backup offers. Accepting Backup Offers! Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjacent to the John Lake Conservation Area, you'll also enjoy easy walking and biking access to Tucker Ranch, the future site of a holistic wellness center, teaching farm, playground and family activity hub. Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe community! This expansive 2,626 sq. ft. home sits on a generous 0.25-acre corner lot. Enjoy the comfort of a newer A/C unit and handler installed in January 2025 and freshly painted interiors (2022) that create a crisp, modern ambiance. The spacious eat-in kitchen features a large island with seating for four, ample cabinetry, a custom pantry, and extensive counter space—perfect for gatherings or morning routines. The first floor features a flexible private bonus room that can easily serve as a home office, study, or a welcoming fifth bedroom for overnight guests. The primary suite includes a beautifully crafted walk-in closet, while the custom laundry room offers built-in cabinetry and a convenient hanging bar for added functionality. Just beyond the living space, the screened-in lanai invites you to relax and unwind. Situated on a prime corner lot, the property also boasts a generously sized yard with endless potential for outdoor enjoyment. The epoxy-coated two-car garage is both functional and stylish, freshly painted and equipped with motion-sensor lighting for your convenience. This Meritage home is solid construction with 6 panel doors throughout and spray foam insulation in the attic. Community amenities include a pool, clubhouse, fitness center, yoga studio, pickleball and tennis courts—everything you need for a vibrant, active lifestyle. With its thoughtful design, abundant amenities, and unbeatable location, this home offers the perfect blend of comfort, convenience, and community.
Listing Agent: Lauren Marason (610-223-7086)
2200 ROMANUM DR, WINTER GARDEN, FL 34787
$560,00040 Days on yellowkey MLS ID: O6408190
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2561 Built: 2015Monthly Fee: $211 Tax: $8,843 (2025)Community: Alexander RdgSpa: NoSingle Family
Taxes:$8,843
Remarks: Come see 2200 Romanum Dr, recently updated with fresh interior paint and partial flooring replacement throughout. The kitchen features a functional island, all stainless steel appliances, and an accent backsplash. The primary bedroom includes a walk in closet, while its bathroom provides double sinks and a separate tub and shower. An exterior covered patio extends to a fenced in backyard. This updated property combines modern comfort and outdoor enjoyment. Included 100-Day Home Warranty with buyer activation
Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)
Listing Agent: Karen Albright (480-462-5392)
7212 DESERT MANDARIN ST, WINTER GARDEN, FL 34787
$650,00062 Days on yellowkey MLS ID: O6401040
0 Days Off yellowkey (back on 5/1/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2605 Built: 2018Monthly Fee: $64 Tax: $5,661 (2025)Community: Highlands/Summerlake Grvs Ph 2Spa: NoSingle Family
Taxes:$5,661
Remarks: Under contract-accepting backup offers. Welcome to your beautifully upgraded home in the heart of Winter Garden! This spacious 4-bedroom, 2.5-bath residence offers the perfect blend of comfort, style, and functionality, complete with a versatile flex room ideal for a home office, study, or playroom. From the moment you step inside, you’ll notice the thoughtful upgrades throughout—enhanced cabinetry, a stylish backsplash, upgraded appliances, and modern light fixtures that elevate the living space. The first-floor flooring has been fully updated, and the front door adds a fresh, inviting touch to the home’s curb appeal. Fresh interior paint (2026) keeps everything feeling clean and move-in ready. The kitchen is equipped with a gas range and flows seamlessly into the main living areas, perfect for everyday living and entertaining. Upstairs and throughout, you’ll appreciate the well-designed layout offering both privacy and open gathering spaces. The Harry Potter closet has been repurposed as a reading nook equipped with a chalk board for young ones to stay entertained. Major system updates provide peace of mind, including a newer HVAC system (approx. 8 years), roof (approx. 8 years), water heater, upgraded HVAC blower motor, and garage door opener mechanism. A tankless water heater, Tesla charger, and security system add modern convenience and efficiency. Step outside to enjoy the fenced backyard with a sprinkler system, and a location that’s tucked away—not on a main road—offering added privacy while still being close to everything. The home is also just a short distance from the community playground. The low HOA covers your cable bill and enhances your lifestyle with access to amenities including a pool, dog park, two playgrounds, and clubhouse, all while maintaining the community’s beautifully kept common areas. Perfectly positioned just minutes from world-renowned attractions like Walt Disney World and Universal Orlando, this home offers unbeatable access to the best of Central Florida’s theme parks. Enjoy the convenience of nearby grocery stores, shopping centers, and everyday essentials just minutes from your doorstep, making errands and retail therapy effortlessly accessible. Don’t miss your opportunity to own this well-maintained, thoughtfully upgraded home in one of Winter Garden’s most desirable areas!
Listing is courtesy of: HOMESMART (407-476-0451)
Listing Agent: Jennifer Micheli (321-229-3704)
15480 SANDFIELD LOOP, WINTER GARDEN, FL 34787
$749,90056 Days on yellowkey MLS ID: O6399241
1 Days Off yellowkey (back on 5/22/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2574 Built: 2013Monthly Fee: $114 Tax: $7,534 (2025)Community: Reserve/Carriage Point Ph 1Spa: YesSingle Family
Taxes:$7,534
Remarks: Under contract-accepting backup offers. One or more photo(s) have been virtually staged. Set within one of Winter Garden’s most sought-after communities, 15480 Sandfield Loop presents a thoughtfully updated residence defined by clean, modern finishes, soaring interior volume, and a seamless connection to outdoor living. A welcoming front elevation and expansive paver driveway introduce the home with presence, leading to a light-filled interior where elevated ceiling heights and continuous wood-look tile flooring create an immediate sense of openness and cohesion. The main living area is anchored by volume and natural light, with large sliding glass doors framing views of the covered lanai and screened pool beyond. The kitchen has been completely redesigned with all-new cabinetry and features granite countertops and a functional island layout that offers both everyday practicality and an ideal setting for gathering. Pendant lighting and stainless steel appliances complete the space, maintaining a clean, timeless aesthetic. All secondary bathrooms have been fully updated with modern finishes, including sleek vanities, updated fixtures, and sliding glass door showers, delivering a polished, move-in ready experience throughout. The primary suite offers a spacious layout with the opportunity to further personalize, creating a private retreat tailored to your vision. Outdoor living is where this home truly shines. The covered lanai extends seamlessly from the interior, overlooking a screened-in pool and spa designed for year-round enjoyment. Beyond, the fully fenced backyard opens to a rare sense of privacy, backing to a rural settlement with no direct rear neighbors, creating a setting that feels both open and secluded. Positioned on a corner homesite along a gently curved street, the property benefits from added spacing, enhanced curb presence, and a more open feel than typical interior lots. Situated just minutes from shopping, dining, and major roadways, this home combines thoughtful interior updates, strong architectural volume, and a highly livable indoor-outdoor layout, an increasingly rare offering at this price point.
Listing is courtesy of: ORLANDO PROPERTY ADVISORS (407-808-3695)
Listing Agent: Kayla Devoogel (407-493-5452)
9942 SUMMERLAKE GROVES ST, WINTER GARDEN, FL 34787
$899,00055 Days on yellowkey MLS ID: O6402319
REDUCED by $20,000 (2.2%) on 05/21/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2935 Built: 2019Monthly Fee: $164 Tax: $11,696 (2025)Community: WatermarkSpa: NoSingle Family
Taxes:$11,696
Elementary School: Panther Lake Elementary
Remarks: Former model home now available for sale in the highly desirable Watermark community of Horizon West! This nearly new residence has been lightly used as a second home and remains in pristine condition, offering the perfect blend of luxury, comfort, and convenience—without the wait for new construction. This beautifully upgraded home showcases custom designer finishes throughout, including extensive wood wall paneling, modern vinyl flooring with no carpet, and fully renovated bathrooms that elevate the overall design. The thoughtfully designed layout features a spacious gourmet kitchen with quartz countertops, elegant cabinetry, and a large center island—ideal for entertaining and everyday living. The main level offers a private guest suite, a half bath with direct access to the pool area, and a versatile flex space currently used as a gym, easily adaptable as a formal dining room or home office. An additional open area near the living room provides the perfect setting for a workspace or playroom. Upstairs, the owner’s suite serves as a relaxing retreat, complemented by two additional bedrooms, a shared bathroom, and ample storage space. Step outside to your private outdoor oasis featuring a north-facing pool that allows for natural sunlight throughout the day while maintaining a shaded and comfortable lanai area. The fully fenced backyard provides added privacy—perfect for enjoying Florida living year-round. Located in the heart of Winter Garden, within the sought-after Horizon West area, residents of Watermark enjoy resort-style amenities including a pool, splash pad, playground, tennis courts, recreational center, and outdoor amphitheater. Conveniently situated just minutes from Disney and with easy access to SR-429, offering seamless connectivity throughout Central Florida.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Mulcy Tenorio (407-403-8229)
17453 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787
$757,99066 Days on yellowkey MLS ID: G5111222
0 Days Off yellowkey (back on 4/19/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $150Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGES Welcome to the Arlington! This single-story floor plan features 4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,726 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The Arlington is perfect for families of all sizes!
10187 MERRYMEETING BAY DR, WINTER GARDEN, FL 34787
$679,00048 Days on yellowkey MLS ID: O6404599
0 Days Off yellowkey (back on 5/20/2026)
REDUCED by $10,000 (1.5%) on 05/11/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2840 Built: 2020Monthly Fee: $250 Tax: $9,595 (2025)Community: Waterleigh Ph 2C-2 & 2C-3Single Family
Taxes:$9,595
Remarks: Under contract-accepting backup offers. Welcome to the highly sought-after Cresswell model in the desirable Waterleigh community of Horizon West — where resort-style living meets everyday convenience! From the moment you enter, you’re greeted by a grand, palm tree-lined entrance that sets the tone for a private tropical retreat. Waterleigh is thoughtfully designed around picturesque ponds and lakes, with beautifully maintained landscaping throughout the community — all included in the HOA — making it one of the most visually stunning neighborhoods in the area. Residents enjoy an impressive array of resort-style amenities, including multiple swimming pools, splash pads, a fully equipped fitness center, tennis courts, sand volleyball courts, fishing piers, scenic walking trails, dog parks, and a grand clubhouse with a full-service event hall. This community perfectly balances the feel of a private resort with a warm, welcoming neighborhood atmosphere. This move-in ready home features 4 spacious bedrooms, 4 full bathrooms, and approximately 2,840 square feet of living space, offering the perfect blend of comfort, style, and modern design to suit today’s lifestyle. Located in a golf cart-friendly community, the home is just minutes from Publix, top-rated schools, and the best shopping, dining, and entertainment that Horizon West has . Enjoy unbeatable convenience with Walt Disney World only 15 minutes away, Orlando International Airport just 30 minutes away, and quick access to Highway 429 for easy travel throughout Central Florida. Waterleigh also hosts weekly and monthly community events, fostering a strong sense of connection and pride among residents. Don’t miss this rare opportunity to own one of Winter Garden’s most desirable homes — where luxury, convenience, and resort-style living come together. Schedule your private showing today and experience the very best of Waterleigh living!
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Chun Cai (951-699-4983)
17059 HARBOR OAK PKWY, WINTER GARDEN, FL 34787
$630,00057 Days on yellowkey MLS ID: O6403063
REDUCED by $5,500 (0.9%) on 05/19/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2692 Built: 2017Monthly Fee: $215 Tax: $8,922 (2025)Community: Waterside/Johns Lake Ph 2ASingle Family
Taxes:$8,922
Remarks: Welcome to this beautiful, well-maintained home located in the Waterside Community at 17059 Harbor Oak Parkway. This inviting property features a spacious living area with modern finishes and newly installed luxury vinyl plank (LVP) flooring great for both everyday living and entertaining.The open-concept layout flows seamlessly into a stylish kitchen equipped with stainless steel appliances, including a newly installed range, along with updated shelving, blinds, and lighting throughout (2024). The first floor also features an additional bedroom, for guests or a home office; whatever suites your needs. Upstairs, you’ll find a versatile loft area great for cozy movie nights, a playroom, or a secondary living space. The primary suite serves as a relaxing retreat, complete with a fully updated master bathroom (2025). Two additional bedrooms provide ample space for family or visitors. Step outside to enjoy the patio, great for entertaining, along with a newly installed fence (2024) that adds both privacy and charm. Conveniently located in a community with A-rated schools and school bus transportation available right on your street. Less than a 2 minute walk to your community pool and gym, with 2 playgrounds and a dock located within the community. This home places you just minutes from the best of Florida living including Disney Resorts, Universal theme parks, and Historic Downtown Winter Garden (award winning Farmers Market) all within a 20-minute drive. With convenient access to Highway 429, commuting and travel throughout Central Florida are a breeze. Plus, you’re less than an hour away from Florida’s beautiful beaches and natural springs.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
3518 TURNINGWIND LN, WINTER GARDEN, FL 34787
$810,00070 Days on yellowkey MLS ID: S5147067
3 Days Off yellowkey (back on 5/19/2026)
REDUCED by $15,000 (1.8%) on 04/30/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2744 Built: 2003Monthly Fee: $115 Tax: $10,313 (2025)Community: Windward Cay 48 125Single Family
Taxes:$10,313
Remarks: Under contract-accepting backup offers. Welcome to 3518 Turningwind Lane, located in a gated upscale community in one of Winter Garden’s most desirable areas! This beautifully maintained 4-bedroom, 3-bathroom home offers the perfect blend of luxury, comfort, and convenience. A classic brick paver driveway and french door entry welcomes you inside, leading to a grand entryway that immediately sets the tone for this light, bright and inviting home. Just to the right of the entry is a spacious bonus room perfect for a home office, den or flex space. Straight ahead, you'll find a large living room with glass french doors that fill the room with natural light from the sparkling pool. To the left is a full sized formal dining area complete with elegant chandelier ideal for hosting family dinners and special occasions. The stunning renovated gourmet kitchen features solid wood cabinetry, beautiful granite countertops, and designer backsplash tile, creating an elegant and functional centerpiece of the home. To the right of the kitchen is an additional dining area featuring a matching bar and wine fridge creating a seamless extension of this beautifully renovated space. The family room offers even more space to gather and entertain also highlighted by french glass doors that lead directly to the pool and outdoor entertaining area, filling the home with abundant natural light throughout. The expansive primary suite is a true retreat, boasting a bay window separate seating area with french door access to the pool, two separate walk in closets and a luxurious en-suite bathroom complete with separate his-and-her vanities, matching windows, and an oversized walk-in shower overlooking a separate relaxing soaker tub. Your private outdoor oasis featuring a covered patio, sparkling screened pool, and large deck is perfect for entertaining. Enjoy peaceful views of the lush conservation area behind the home with no rear neighbors, providing privacy and a serene backdrop for relaxation. A convenient door from the patio leads directly to the pool bath and into the thoughtfully designed guest wing offering three additional bedrooms and a third full bathroom. Buyers will appreciate the added peace of mind with major updates already completed, including a brand new water heater, 2021 roof and HVAC replaced in 2019. Additional highlights include a 3-car garage, a laundry room with sink and cabinetry (washer & dryer included), gorgeous ceramic tile and real wood floors throughout and zoned for excellent schools. Conveniently located just minutes from highways, shopping/dining (Winter Garden Village) parks/recreation (West Orange Trail and West Orange Country Club) and entertainment (Orlando’s world-famous theme parks and tourist attractions) - it's truly a gem! This exceptional property offers Florida living at its finest in an exclusive highly sought after community. A home like this is a rare opportunity, so schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Melanie Shenosky (603-674-9405)
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