Location: Winter Garden
Do Not Show Listings
5778 LAUREL CHERRY AVE, WINTER GARDEN, FL 34787
$530,00069 Days on yellowkey MLS ID: O6395452
REDUCED by $10,000 (1.9%) on 06/04/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2524 Built: 2016Monthly Fee: $195 Tax: $9,031 (2025)Community: Signature LakesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,031
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to this sophisticated, modern and spacious, elegant two-story home in the beautiful neighborhood of Independence in the Horizon West area. Across the pond, this 2,524-square-foot home offers an open concept living space. As you enter through the front door, you are greeted with gorgeous tile floors. The kitchen features beautiful modern espresso cabinetry, a large pantry, stainless steel appliances, and an oversized island overlooking the family room and dining area. This open floor plan provides a great space for entertaining and includes dual primary bedrooms on the main and second levels. The expansive primary suite features a walk-in closet, separate sinks with beautiful cabinetry, a soaking tub and a luxurious walk-in shower. Other features completing this exquisite home include three bedrooms and an upstairs loft on the second level, plus a two-car garage. Capturing some of the best living in Florida, the Independence neighborhood provides a resort-style swimming pool, walking trails, basketball courts, tennis courts, fitness center and a private community boat ramp. Conveniently minutes from Disney World, Orange County National Golf Course, restaurants, shopping, hospitals and zoned for top-rated schools. Schedule your private showing and start enjoying the Florida lifestyle!
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Llin Lu, Pa (954-907-3868)
1968 PANTHEON DR, WINTER GARDEN, FL 34787
$529,90033 Days on yellowkey MLS ID: O6404386
0 Days Off yellowkey (back on 6/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1971 Built: 2015Monthly Fee: $211 Tax: $3,832 (2025)Community: Alexander RdgSingle Family
Taxes:$3,832
Elementary School: Hamlin Elementary
High School: West Orange High
Middle School: Hamlin Middle
Remarks: Beautifully maintained home in the Heart of Winter Garden! Located in the highly sought-after neighborhood of Alexander Ridge, this single story Craftsman-style home embodies the feeling of a peaceful family community, with its stone-covered columns and a welcoming front porch. Continuing through the wide foyer you'll find a den/flex room, well-suited for a home office or playroom. The upgraded kitchen with thick quartz countertops, 42” solid wood cabinets, and a large island, is open to the dining and family rooms, making it ideal for entertaining. At the end of the day, the expansive owners' suite is a true retreat, featuring a massive walk-in closet, dual vanities, a soaking tub, and a large upgraded walk-in shower. Set apart from the Owners' suite, you'll find the two additional bedrooms, a tasteful guest bath, and the spacious laundry room. Step outside to the relaxing covered and screened lanai, perfect for enjoying the evening breezes in privacy. Situated in a fantastic community with a neighborhood park, gazebo, miles of trails, and a refreshing pool, you'll be just minutes from the best of Hamlin and Winter Garden—shopping, dining, and top-rated schools. Although the serenity feels like its own little world, you're only a short drive to Disney World®, Universal Studios® and all the attractions Central Florida has to offer. Don’t miss this incredible opportunity—schedule your showing today!
Listing is courtesy of: KUNKLE REALTY GROUP (844-978-7750)
Listing Agent: Greer Kunkle (321-250-0106)
15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787
$809,90074 Days on yellowkey MLS ID: O6393190
REDUCED by $10,100 (1.2%) on 06/04/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3902 Built: 2005Monthly Fee: $243 Tax: $7,653 (2025)Community: Stoneybrook WestSingle Family
Taxes:$7,653
Elementary School: Whispering Oak Elem
Middle School: SunRidge Middle
Remarks: One or more photo(s) has been virtually staged. SOLAR SYSTEM WILL BE PAID OFF BY THE SELLER AT CLOSING, $65,000 VALUE! Seller offering RATE BUY-DOWN so Buyer will enjoy lower monthly payments! Nestled on this beautifully remodeled and RECENTLY PAINTED home located on a premier OVERSIZED CORNER LOT within the guard-gated enclave of STONEYBROOK WEST, this stunning 5-bedroom, 3-bathroom residence offers the ultimate Winter Garden lifestyle. The home has been meticulously enhanced with MODERN UPDATES, ensuring a MOVE-IN-READY experience for today’s discerning buyer. SAVE ON UTILITY BILLS WITH THE WHOLE HOUSE SOLAR SYSTEM AND ELECTRIC CAR CHARGER. Inside, the open-concept layout is anchored by a SPACIOUS KITCHEN featuring quartz countertops, a central island, and HIGH-END STAINLESS STEEL APPLIANCES, all flowing into a spacious family room warmed by a classic fireplace. High-volume ceilings—reaching 9.25 feet on the main floor and an impressive 10.50 feet in the massive upstairs bonus room—create an airy, grand atmosphere throughout. The well-appointed laundry room includes a GE ULTRA WASHER AND DRYER, along with a STAINLESS STEEL UTILITY SINK for added convenience. The garage is equally impressive, featuring a heavy-duty Husky organizational system that provides exceptional storage and functionality. Retreat to the primary suite, where tray ceilings and a private walk-out balcony offer a peaceful vantage point overlooking the championship golf course. The lifestyle here extends far beyond the front door. Stoneybrook West is a premier “live-play” community boasting 24-hour staffed security and a spectacular waterfront clubhouse perched on the shores of Black Lake. For the outdoor enthusiast, the amenities are unmatched: enjoy private lake access via a community boat ramp and the rare convenience of an on-site boat storage lot. Whether you are hitting the links on the championship golf course, working out in the fitness center, or relaxing at the resort-style pool, every day feels like a vacation. Perfectly positioned for convenience, you are just 6 minutes from Winter Garden Village, 18 minutes from Walt Disney World, and only 30 minutes from Orlando International Airport. This home combines the security of a gated community, the luxury of recent high-end improvements, and the rare perk of Florida lake living. Call today to schedule your private showing!
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
925 BAINBRIDGE LOOP, WINTER GARDEN, FL 34787
$815,00046 Days on yellowkey MLS ID: O6402075
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3580 Built: 2008Monthly Fee: $72 Tax: $4,880 (2025)Community: Covington ParkSpa: NoSingle Family
Taxes:$4,880
Elementary School: Dillard Street Elem
High School: Ocoee High
Middle School: Lakeview Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to Covington Chase, one of the most sought-after communities in Winter Garden, just minutes from the charm and energy of historic downtown. Situated on an oversized 0.38-acre lot, this 4-bedroom, 4 full bathroom home offers a rare combination of space, functionality, and flexibility. The fully fenced backyard provides plenty of room to relax, entertain, or create your own outdoor retreat, while the long driveway and 3-car garage give you ample parking and storage, including space for a golf cart so you can fully enjoy this golf cart district lifestyle. The floor plan is thoughtfully designed for both everyday living and long-term versatility. The primary suite is located downstairs, creating a private retreat with two walk-in closets and a large bathroom that offers both space and comfort. Also on the first floor is a dedicated office, perfect for working from home or creating a quiet, separate space for productivity. In addition, the first floor features a Jack and Jill bedroom and bathroom setup, ideal for guests, kids, or multigenerational living. This layout allows for privacy while still maintaining a connected and functional flow throughout the home. Upstairs, you will find a spacious loft that can be used as a second living area, media room, or play space, along with a full bedroom and full bathroom. This upstairs setup is perfect for guests, older children, or anyone who would benefit from having their own private area within the home. The overall layout gives you multiple living zones and flexibility, making it easy to adapt the home to your lifestyle, whether that means working from home, hosting guests, or simply enjoying extra space. The roof was replaced just a few years ago, offering added peace of mind and reducing one of the major future expenses for a new owner. Beyond the home itself, the lifestyle here is what truly stands out. You are just minutes from the Downtown Winter Garden Historic District, known for its brick-lined streets, locally owned restaurants, coffee shops, boutiques, and the popular weekly farmers market. Living in the golf cart district means you can easily head downtown for dinner, events, or a casual night out without needing to get in your car. You are also close to the West Orange Trail, a 22-mile scenic trail perfect for biking, walking, and enjoying the outdoors. Homes with this kind of lot size, a flexible floor plan with a downstairs primary suite, office, additional bedroom, plus an upstairs loft and private guest space, and a 3-car garage are hard to find this close to downtown. This is a unique opportunity to own a home that offers both the space you need and the lifestyle you want.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
16185 TALIESIN ST, WINTER GARDEN, FL 34787
$660,00026 Days on yellowkey MLS ID: O6407177
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2372 Built: 2020Monthly Fee: $127 Tax: $6,048 (2025)Community: HawksmoorSpa: NoSingle Family
Taxes:$6,048
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: One or more photo(s) has been virtually staged. Beautifully maintained 4-bedroom, 3-bathroom two-story home located in the highly desirable Winter Garden area. Featuring over $58,000 in builder upgrades and premium features, including a premium corner lot, this home offers the perfect blend of comfort, style, and functionality. Fully paid solar panels and a fully owned whole-house water filtration system add even more value and energy efficiency. From the charming front porch and landscaped entry to the thoughtfully designed interior, every detail has been carefully selected. The open-concept first floor features tile flooring throughout the main living areas and is filled with natural light, creating a bright and airy feel. The spacious living and dining areas flow seamlessly into the gourmet kitchen, complete with stainless steel appliances, elegant upgraded cabinetry, quartz countertops, designer backsplash, and generous counter space, making it ideal for everyday living and entertaining. A first-floor bedroom and full bathroom provide the perfect setup for guests, multi-generational living, or a private home office. Upstairs, a spacious loft offers a great flex space for a media room, game room, or additional living area. The expansive primary suite serves as a relaxing retreat with a tray ceiling, large walk-in closet, and private bath featuring dual sinks. Additional bedrooms provide comfortable space and ample storage. Additional upgrades include upgraded lighting fixtures, enhanced tile and carpet flooring, 8-foot first-floor doors, added laundry room cabinetry, and an attached two-car garage with epoxy flooring, custom cabinetry, and an additional refrigerator. Residents enjoy access to fantastic community amenities including a clubhouse, resort-style pool, park, playground, and sidewalks throughout the neighborhood. Conveniently located just minutes from Hamlin Town Center, shopping, dining, entertainment, Walt Disney World, and major highways with easy access to Orlando and surrounding areas. This exceptional home combines modern upgrades, energy-efficient features, functional living spaces, and an unbeatable location. Schedule your private showing today.
11864 SHINE VIEW LN, WINTER GARDEN, FL 34787
$599,990203 Days on yellowkey MLS ID: O6361583
REDUCED by $25,000 (4.0%) on 06/04/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2489 Built: 2025Monthly Fee: $190 Tax: $1,989 (2024)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Tax Year: 2024
Remarks: Under Construction. Waterleigh presents the Clearden. 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’ll find a bedroom and downstairs powder room. 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 three 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. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Clearden 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)
1432 MARBLE CREST WAY, WINTER GARDEN, FL 34787
$824,50057 Days on yellowkey MLS ID: O6398054
4 Days Off yellowkey (back on 6/2/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3734 Built: 2005Monthly Fee: $243 Tax: $7,963 (2025)Community: Stoneybrook West 44/134Spa: YesSingle Family
Taxes:$7,963
Remarks: Under contract-accepting backup offers. GOLF COURSE POOL HOME + TILE ROOF + GUARD-GATED LIVING in one of Winter Garden’s most sought-after communities. Welcome to 1432 Marble Crest Way, located in the Fox Hunt section of Stoneybrook West, a 24-hour manned, guard-gated golf community known for its distinctive Mediterranean-style homes, mature landscaping, and resort-style amenities. This 5-bedroom, 3.5-bath home offers over 3,700 square feet of flexible living space with multiple living areas, a private office, and recent buyer-visible updates throughout. Designed for both everyday living and entertaining, the layout includes formal dining, two spacious first-floor living areas, and an oversized upstairs bonus room ideal for a media room, game room, fitness space, playroom, or secondary retreat. The private office offers flexibility for remote work, hobbies, or a quiet study space. The kitchen opens to the main family room, creating a comfortable flow for gathering and everyday living, while natural light fills the home throughout. Recent improvements include NEW UPSTAIRS FLOORING, FRESH INTERIOR PAINT in many rooms, and UPDATED FIXTURES, giving the home a refreshed and move-in-ready feel. Step outside to a SCREENED-IN POOL overlooking the golf course, complete with a BUILT-IN OUTDOOR KITCHENETTE and a RECENTLY REFINISHED POOL—perfect for relaxing evenings, entertaining, and enjoying Florida living year-round. Stoneybrook West offers an amenity-rich lifestyle including 24-hour guard-gated security, golf, clubhouse, fitness center, resort-style pool, tennis, pickleball, basketball, playgrounds, fishing dock, boat ramp with Black Lake access, and the Stoneybrook West Golf Club with SB Prime restaurant and bar. Ideally located just minutes from Winter Garden Village, downtown Winter Garden, SR-429, Disney, shopping, dining, and everyday conveniences.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
10705 PETRILLO WAY, WINTER GARDEN, FL 34787
$725,00083 Days on yellowkey MLS ID: O6391807
1 Days Off yellowkey (back on 4/28/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2528 Built: 2020Monthly Fee: $102 Tax: $9,936 (2025)Community: Winding Bay Ph 1BSingle Family
Taxes:$9,936
Remarks: Under contract-accepting backup offers. Set against stunning private CONSERVATION VIEWS this SINGLE STORY four bedroom three FULL bathroom home is the one you've been waiting for! Just 10 minutes from the gates of Walt Disney World, this Winter Garden residence in the heart of HORIZON WEST offers a rare blend of luxury and flexibility. A spacious front porch paired with a paver driveway creates a striking first impression. No need to call the interior designer, this home has already been beautifully designed with wainscoting, double crown molding, illuminated tray ceilings, an electric LED fireplace, and a shiplap feature wall. 8FT INTERIOR DOORS create an immediate sense of scale and sophistication, enhancing natural light flow and giving the home a more open feel. TRIPLE SLIDING GLASS DOORS overlook the LARGE PRIVATE FENCED IN BACKYARD. This home delivers on the Florida indoor/outdoor living that everyone desires! The shady back Lanai has a PANORAMIC SCREEN and A SUMMER KITCHEN with sink, grill, and mini fridge. The GOURMET KITCHEN is the heart of this home. 13 FOOT QUARTZ ISLAND with seating for eight, SOFT CLOSE CABINETS and DRAWERS, PULL OUT DRAWERS in the kitchen cabinets for easy storage and organization, under cabinet lighting, and the VENT HOOD vents out of the house. The Primary Suite overlooks the green backyard's private conservation view. The room is spacious enough for a king size bed and additional furniture. The illuminated tray ceiling feels both modern and timeless, adding depth, dimension, and a polished finish to the space. The primary bathroom features double sinks, a separate tub and shower, and a custom built-in closet. The SECOND FRONT DOOR is a PRIVATE ENTRANCE that leads to the 320 square foot GUEST SUITE. The guest suite is perfect for multi-generational living, guests, or a home office. The GUEST SUITE has 1 BEDROOM, 1 FULL BATHROOM with WALK-IN SHOWER, living room, dedicated laundry with STACKABLE WASHER AND DRYER, and a dine-in KITCHENETTE with a full-size refrigerator, microwave, and sink! Additional features to note include 2020 ROOF, NO CARPET, PENTAIR Non-Salt Water Filtration System, ALEXA SMART HOME Controls, DROP ZONE, DEDICATED LAUNDRY ROOM WITH CABINETS and UNDERMOUNT SINK, STORAGE RACK and CABINETS in the TWO CAR GARAGE, NO CDD fee. Winding Bay offers a resort-style, zero-entry pool, 4 tot lots, 2 open play fields, a dog park, and covered picnic areas. Located only minutes from the HAMLIN SHOPPING CENTER, FLAMINGO CROSSING, Advent Health, Orlando Health, Highway 429, DISNEY SPRINGS, A-RATED PUBLIC SCHOOLS, and so much more! Schedule your private tour today.
16834 HOBE SOUND CT, WINTER GARDEN, FL 34787
$599,99048 Days on yellowkey MLS ID: O6401373
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2494 Built: 2026Monthly Fee: $190 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Remarks: Under Construction. Waterleigh presents the Clearden. This amazing 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’ll find the first bedroom complete with ensuite bathroom and a powder room across the hall. 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 additional three 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 sinks and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor for convenience. This home features a two car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterleigh, the Clearden includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*
10043 SEQUEL ALY, WINTER GARDEN, FL 34787
$560,000106 Days on yellowkey MLS ID: O6384246
0 Days Off yellowkey (back on 6/2/2026)
REDUCED by $9,000 (1.6%) on 05/05/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2502 Built: 2018Monthly Fee: $100 Tax: $8,237 (2024)Community: Storey Grove Ph 1B-2Single Family
Taxes:$8,237
Remarks: Under contract-accepting backup offers. About 10 minutes to Disney. Corner lot facing open green space. Main floor primary suite with a second upstairs. Opportunity to secure a BELOW MARKET rate through an ASSUMABLE MORTGAGE for qualified buyers. Located in Storey Grove in the heart of Horizon West, this home is positioned for both convenience and day to day livability. You are about 5 minutes to Publix and 15 minutes to Hamlin Town Center for dining, shopping, and everything you need close to home. The lot and orientation are what set this home apart. Instead of looking into another backyard, you face open park space and green views, bringing in more natural light and a more open feel throughout the home. All carpet on the stairs and second floor has been replaced with wood look luxury vinyl flooring, crown molding has been added throughout, and the interior has been freshly repainted so there are no immediate projects waiting after closing. The layout is flexible and practical. Two primary suites, including one on the main level, create options for guests, multigenerational living, or a private office without sacrificing bedroom space. The main living and dining areas are open and functional, while the upstairs loft works well as a playroom, media space, or work from home area. The backyard is fully fenced with an in ground sprinkler system, giving you usable outdoor space that is easy to maintain. The rear facing garage with alley access keeps the curb appeal clean and includes an EV charger, while the corner lot allows for additional nearby parking for guests. Storey Grove offers a community pool, clubhouse with gym, parks, playgrounds, and miles of sidewalks, with green space directly across the street extending your everyday living area. Zoned for Water Spring Elementary, Water Spring Middle, and Horizon High School.
13846 FRESH IVY ST, WINTER GARDEN, FL 34787
$649,900252 Days on yellowkey MLS ID: O6346706
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2108 Built: 2024Monthly Fee: $534 Tax: $2,180 (2024)Community: Del Webb Oasis Ph 3Single Family
Taxes:$2,180
Remarks: Welcome to 13846 Fresh Ivy Street, nestled in the highly desirable Winter Garden area, just minutes away from world-famous Orlando attractions. This home is easy on the eyes and offers the perfect blend of comfort, convenience, and luxury living. This beautifully designed two-bedroom, two-and-a-half-bath home features over 2,100 square feet of living space. With spacious interiors, thoughtful finishes, and modern upgrades, this home provides both style and functionality. Inside you will discover bright, open living areas, a gourmet kitchen, and bedrooms designed as your own personal sanctuary. Whether you’re hosting guests or enjoying a quiet evening at home, every detail has been styled with comfort in mind. Imagine mornings spent in the fitness center, afternoons sunbathing on a zero entry sun shelf by a cabana, and nights gathering with friends by the fire pits underneath the stars. This home and community is about freedom, fun, and comfort all in one place. This isn’t just a home, it’s the lifestyle you’ve earned.
8018 BOWERY DR, WINTER GARDEN, FL 34787
$699,900329 Days on yellowkey MLS ID: O6325853
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3075 Built: 2017Monthly Fee: $208 Tax: $5,724 (2024)Community: Lake Hancock PreserveSingle Family
Taxes:$5,724
Elementary School: Summerlake Elementary
Remarks: Welcome to 8018 Bowery Drive, a spacious 5-bedroom, 3-bathroom home perfectly positioned in Winter Garden right on the edge of Windermere. This layout offers flexibility and comfort for everyday living while also providing the space to entertain. Upstairs, you’ll find the private primary suite, a generous loft, a full bathroom, and three additional bedrooms, two of which offer nightly views of Disney fireworks right from the window. Downstairs features two separate living spaces, plus a conveniently located bedroom and full bathroom ideal for guests or in-laws. Step outside through the telescoping sliding glass door to enjoy a large covered porch and private backyard with no rear or side neighbors. Curb appeal shines with a paver driveway and charming wrap-around front porch. Just minutes from the 429, Disney, and all that Windermere has to offer, this home blends location, privacy, and everyday convenience. Don’t miss the chance to make this beautiful home yours!
6100 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$950,0008 Days on yellowkey MLS ID: O6412033
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3777 Built: 2016Monthly Fee: $195 Tax: $11,678 (2025)Community: Signature Lakes Ph 3B-4 3B-5 & 3Single Family
Taxes:$11,678
Elementary School: Independence Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: One or more photo(s) has been virtually staged. HUGE CORNER LOT featuring 5 bedrooms, 3 full bathrooms and a 3 car garage with Epoxy flooring in a highly desirable neighborhood! With new fresh paint throughout, this move-in-ready home offers space, comfort, and versatility. The oversized backyard offers endless possibilities for customization, outdoor entertaining, and recreation. The spacious owner's suite is complete with two walk-in closets and a private en-suite bathroom. Upstairs, the expansive bonus room offers endless possibilities as a home theater, game room, in-law suite, or large bedroom. In addition to the owner's suite and bonus room, you'll find three generously sized secondary bedrooms upstairs that provide ample space and flexibility. Downstairs features another room with a closet and it has a connecting full bathroom, making it ideal for an office or additional guest room. The beautifully upgraded kitchen is the heart of the home, offering the perfect space for cooking, dining, and creating lasting memories. Featuring two expansive living rooms on the main level plus a formal dining room, this home is ideal for both entertaining guests and enjoying quality time together. With a versatile floor plan, generous living spaces, and endless possibilities, come experience everything this remarkable property has to offer. This is more than a house, it's a place to call home. Some photos have been virtually staged to illustrate potential furniture placement, room functionality, and design possibilities, helping buyers envision the home's full potential.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Crystal Taylor (407-607-6585)
2621 SHIREHALL LN, WINTER GARDEN, FL 34787
$475,00095 Days on yellowkey MLS ID: O6386585
0 Days Off yellowkey (back on 5/14/2026)
REDUCED by $25,000 (5.0%) on 04/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 2003Monthly Fee: $243 Tax: $3,181 (2024)Community: Stoneybrook West Ut 04 48 48Spa: NoSingle Family
Taxes:$3,181
Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT. Welcome to this beautifully maintained 3-bedroom, 2-bath home nestled in a 24 hour guard-gated golf community offering resort-style living. Enjoy tranquil mornings from the screened lanai overlooking a serene pond, creating the perfect setting for relaxation or entertaining. The thoughtfully designed floor plan features spacious living areas, abundant natural light, and comfortable bedrooms ideal for both everyday living and guests. The spacious primary suite has a beautiful water view with ensuite having dual sinks, garden tub and walk in shower. This spilt bedroom plan adds to the convenience of privacy, noise reduction and efficient space management. The open Kitchen overlooks the family room and has a breakfast area with center island and granite countertops. The interior has just been painted first of March, New water heater 4/2026. Residents enjoy access to an impressive array of amenities, including a championship golf course, clubhouse, resort-style pool, fitness center, tennis and pickleball courts, walking and biking trails, and an active social calendar. Conveniently located near shopping, dining, and entertainment, this home offers the perfect blend of comfort, security, and lifestyle. Please call for your showing today.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Barbara Waltman (407-616-2790)
869 BENDING OAK TRL, WINTER GARDEN, FL 34787
$520,000211 Days on yellowkey MLS ID: O6358341
REDUCED by $10,000 (1.9%) on 05/05/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1975 Built: 2012Monthly Fee: $109 Tax: $5,262 (2024)Community: Oaks/Brandy Lake 01 Rep A & BSingle Family
Taxes:$5,262
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home located in The Oaks at Brandy Lake; Situated in the highly desirable golf cart district of Winter Garden. The home offers an open-concept layout featuring a spacious dining and living area with sliding glass doors that leads to a covered patio and FENCED back and side yard. The kitchen includes stainless steel appliances (New Refrigerator 2024), (New Garbage Disposal 2025) and generous counter space. The home features FULLY PAID SOLAR PANELS and rear 2-car garage (New Garage Door Opener 2025) and ample parking in the front of the home. Residents have access to community amenities including a pool and playground. Conveniently located a little over 1 mile away from Downtown Winter Garden, you can enjoy the weekly Farmer's Market and plethora of shops and restaurants. You also have access to major highways (about a 5 minute drive to 429 and Turnpike).
Listing Agent: Xiomara Pratts (407-993-2865)
1028 SPRING LANDING DR, WINTER GARDEN, FL 34787
$550,00014 Days on yellowkey MLS ID: O6410232
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2275 Built: 1990Monthly Fee: $25 Tax: $3,703 (2026)Community: Crown Point SpringsSingle Family
Taxes:$3,703
Tax Year: 2026
Remarks: One or more photo(s) has been virtually staged. 1028 Spring Landing Dr offers the perfect combination of comfort, style, and location in one of Central Florida's most desirable communities. This beautifully upgraded and meticulously maintained 4-bedroom, 3.5-bathroom home features a spacious fenced backyard, ideal for entertaining, pets, or enjoying Florida living year-round. Inside, you'll find gorgeous wood-look tile flooring throughout, adding both elegance and durability to the home's modern feel. Major updates provide peace of mind for the next owner, including a new roof installed in 2019, fresh exterior paint, and a brand-new A/C system replaced in 2025. Pride of ownership shines throughout every detail of this move-in-ready property. Conveniently located just minutes from vibrant Downtown Winter Garden, residents can enjoy easy access to the award-winning farmers market, local dining, boutique shopping, the West Orange Trail, parks, breweries, and community events. With quick access to major highways, Disney attractions, and all that Central Florida has to offer, this home truly delivers both lifestyle and convenience.
16821 HOBE SOUND CT, WINTER GARDEN, FL 34787
$546,990179 Days on yellowkey MLS ID: O6367156
REDUCED by $8,000 (1.4%) on 06/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2027 Built: 2025Monthly Fee: $190 Tax: $1,989 (2024)Community: WaterleighSpa: NoSingle Family
Remarks: Under Construction. Waterleigh presents the Cordale. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the home you’ll find a downstairs powder room and laundry room complete with doors for privacy. The well-appointed kitchen overlooks the family 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. Bedroom one is located off the living space in the back of the home for privacy. The bedroom one-bathroom impresses with double bowl vanities, toilet room with privacy door, shower/tub space, and spacious walk in closet. As we head up to the second floor, we are greeted with a loft area and two additional bedrooms. The upstairs bedrooms share a bathroom and linen closet for extra storage. This home features a two-car garage located at the rear of the home with drop zone as you enter the first floor. Like all homes in Waterlerigh, the Cordale 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.*
113 W DIVISION ST, WINTER GARDEN, FL 34787
$539,90042 Days on yellowkey MLS ID: S5148787
REDUCED by $10,090 (1.8%) on 06/04/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1487 Built: 1951 Tax: $4,920 (2025)Community: Winter Garden Shores RepSingle Family
Taxes:$4,920
Remarks: Welcome a beautifully remodeled Winter Garden home that seamlessly blends classic charm with modern upgrades! step inside to discover an open-concept kitchen, top appliances, quartz countertops, sleek modern bathrooms, new windows, and durable waterproof laminate floors, excellent screen porch. Perfect for everyday living and entertaining alike. New windows flood the interior with natural light, while luxury flooring flows throughout for effortless style and maintenance. This inviting 4-bed, 2-bath residence offers 1,487 sq ft of thoughtfully reimagined living space on a generous 0.17-acre lot in the desirable Winter Garden Shores neighborhood. Relax in sleek, modern bathrooms and enjoy the lush Florida weather from your excellent screened porch, ideal for morning coffee or evening gatherings. The home also includes an attached garage and has been upgraded with central air and updated finishes throughout. Located just moments from top schools, City Hall, dining, parks, and major commute routes, this home offers convenience without compromising. Whether you’re a growing family, first-time buyer, or relocating to the area, this Winter Garden gem is not to be missed! Owner offering 5k to closing cost..
Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)
Listing Agent: Marcelo Garrido (321-502-4448)
11223 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$809,990116 Days on yellowkey MLS ID: O6382359
1 Days Off yellowkey (back on 6/4/2026)
REDUCED by $10,000 (1.2%) on 06/04/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2866 Built: 2025Monthly Fee: $250 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Remarks: Under Construction. Waterleigh presents the Cresswell. This two-story all concrete block construction single-family home features 5 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’ll find a bedroom and 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 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. Customize the second floor of this home to create a space that meets your needs but transforming the loft area to a fifth bedroom with full bath or Guest Suite with ensuite bathroom. 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.*
11145 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$864,990176 Days on yellowkey MLS ID: O6367437
REDUCED by $11,000 (1.3%) on 05/28/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3327 Built: 2025Monthly Fee: $200 Tax: $1,989 (2024)Community: WaterleighSpa: NoSingle Family
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.*
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