Location: Winter Garden
Do Not Show Listings
441 COURTLEA OAKS BLVD, WINTER GARDEN, FL 34787
$1,199,90043 Days on yellowkey MLS ID: O6385964
INCREASED by $80,900 (7.2%) on 04/02/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4001 Built: 2000Monthly Fee: $83 Tax: $5,551 (2024)Community: Courtlea OaksSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,551
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2024
Middle School: Lakeview Middle
Remarks: One or more photo(s) has been virtually staged. One of the largest homes in the highly desirable Courtlea Oaks community, this spacious 5-bedroom, 4.5-bath pool home offers over 4,000 square feet of living space and an exceptional opportunity in the heart of Winter Garden’s golf cart district. The flexible floor plan includes a rare apartment above the garage connected to the main home, providing ideal space for guests, extended family, a private office, or additional living quarters. Important updates have already been completed by these original to the home owners, including a new roof and A/C systems installed just two years ago, offering peace of mind for the next owner. Step outside to enjoy a beautiful pool and a private setting backing to the West Orange Trail, perfect for biking, walking, and outdoor recreation right from your backyard. Located just minutes from historic downtown Winter Garden, residents enjoy boutique shopping, dining, breweries, and the award-winning Saturday Farmers Market, along with numerous festivals and community events throughout the year. With its generous square footage, versatile layout, and unbeatable location, homes like this rarely come available in Courtlea Oaks.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Jennifer Coon (321-948-8056)
5074 BREEZY ACRES ST, WINTER GARDEN, FL 34787
$1,000,000109 Days on yellowkey MLS ID: O6369788
Bed: 7 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4720 Built: 2021Monthly Fee: $115 Tax: $11,152 (2023)Community: Wincey GrovesSingle Family
Taxes:$11,152
Elementary School: Hamlin Elementary
High School: Horizon High School
Tax Year: 2023
Middle School: Hamlin Middle
Remarks: MOVE-IN READY | EASY OWNER FINANCING AVAILABLE | FURNITURE NEGOTIABLE WITH PURCHASE Welcome to an exceptional opportunity in the heart of Winter Garden’s highly sought-after Wincey Groves community. This beautifully upgraded Sweetwater model by Dream Finders Homes, built in 2021, offers over 4,700 square feet of refined living space with 7 bedrooms and 4.5 bathrooms, plus two additional flex rooms that can easily convert this home into a 9-bedroom layout. Thoughtfully designed for both everyday comfort and elevated entertaining, this move-in-ready residence delivers a rare combination of space, sophistication, and flexibility in one of Central Florida’s most desirable locations. From the moment you arrive, the home’s enhanced elevation, extended driveway, and welcoming front porch set the tone for what awaits inside. The open-concept floor plan is filled with natural light and showcases 9-foot doors, soaring ceilings, upgraded engineered hardwood flooring, and expansive sliding glass doors that create a seamless indoor-outdoor flow. The primary suite is conveniently located on the main level, offering a private retreat complete with additional windows, a spa-inspired en-suite bath featuring a soaking tub for two, upgraded glass-enclosed shower, and refined finishes designed for relaxation. Also on the first floor are a private downstairs office, half bath, and a converted third garage space thoughtfully designed as a dedicated home gym, adding exceptional functionality and value. At the heart of the home, the chef’s kitchen impresses with an oversized gathering island, quartz countertops, wrap-around cabinetry, double ovens, built-in microwave, farmhouse sink, under-cabinet lighting, and an abundance of storage—perfect for entertaining and daily living alike. Upstairs, you’ll find the remaining bedrooms, including a Jack-and-Jill bathroom, generous walk-in closets throughout, and an expansive home theater/game room. Combined with the additional flex rooms, the home offers outstanding adaptability for multi-generational living, guest accommodations, or expanded work-from-home needs. Additional features include smart-home technology, fiber-optic internet, a hardwired security system with cameras, dual AC units for optimal climate control, and both front and rear porches overlooking a private fenced backyard. Ideally located near top-rated schools, community parks, and the vibrant Hamlin area’s shopping and dining, this home also offers a compelling financial advantage. The sellers are offering seller financing with 20% down and a 5.99% interest rate, providing flexibility and potential savings for qualified buyers. Luxury, space, and opportunity converge here—schedule your private tour today to experience it firsthand.
Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)
Listing Agent: Daniel Rodriguez (407-934-0305)
107 TRADITIONS DR, WINTER GARDEN, FL 34787
$499,99531 Days on yellowkey MLS ID: S5145650
REDUCED by $24,980 (4.8%) on 04/01/2026
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
Elementary School: Dillard Street Elem
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. Big backyard fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room in garage- perfect for the handyman. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools! Solar panels will be paid off at closing!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Rick Evans, Ii (407-538-9295)
13043 SANDCASTLE DRIVE, WINTER GARDEN, FL 34787
$846,0001 Day on yellowkey MLS ID: O6399529
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1943 Built: 2022Monthly Fee: $534 Tax: $10,109 (2025)Community: Del Webb OasisSpa: NoSingle Family
Taxes:$10,109
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Experience the perfect blend of luxury and convenience with the Palmary dream home. Formerly a model home, this stunning one-story residence showcases a thoughtfully designed layout with 3 spacious bedrooms, 2 full bathrooms, and a 2-car garage. Enjoy your private outdoor oasis featuring an in-ground pool with a sun shelf and a covered lanai pre-plumbed for an outdoor kitchen. Step inside to the heart of the home, the gourmet kitchen is a standout feature, equipped with 42" Stone Gray cabinetry, quartz countertops, a sophisticated decorative tile backsplash, stainless steel sink, and upgraded faucet. Whirlpool stainless steel appliances, including a refrigerator and natural gas range, complete this culinary haven. The open-concept living area, flooded with natural light from expansive windows and highlighted by tall ceilings and a tray ceiling at the gathering room, creates an airy, welcoming space perfect for relaxing or entertaining. Retreat to the luxurious owner’s suite, a serene sanctuary with a spacious walk-in closet and a spa-like en suite bathroom. Dual vanity sinks, a frameless glass enclosed walk-in shower with a built-in bench, an enclosed toilet, and a linen closet complete the tranquil space. At the front of the home, the two spare bedrooms and bathroom provide ample space for guests or personal use. The practical laundry room, complete with built-in cabinetry, a utility sink trimmed in quartz, and Whirlpool washer and dryer makes everyday tasks a breeze. Designer-curated selections elevate this home with pendant pre-wiring, comfort-height toilets, brushed nickel hardware and plumbing fixtures, Sherwin Williams City Loft interior paint, and wood-look luxury vinyl plank flooring throughout the entire home (except for the bathrooms and laundry rooms which are outfitted with tile). For modern convenience, this home is equipped with a smart thermostat, surround sound pre-wire, security system pre-wire, digital IP camera pre-wire, LED downlights, and additional data ports. Blending luxury, comfort, and cutting-edge connectivity, this home is designed for today’s lifestyle. Schedule an appointment to see it today!
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
6441 WILD PERSIMMON WAY, WINTER GARDEN, FL 34787
$617,9901 Day on yellowkey MLS ID: G5111080
0 Days Off yellowkey (back on 4/15/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2515 Built: 2026Monthly Fee: $150 Tax: $298 (2025)Community: Avalon WoodsSingle Family
Taxes:$298
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. 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.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
6249 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$941,0151 Day on yellowkey MLS ID: G5111078
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4236 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Taxes:$0
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Welcome to Arlington with Bonus! This stunning 4236 square foot, two-story floor plan boasts 6 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio, or head upstairs to discover a generously sized bonus room, ideal for a playroom, home office, or media space. Don’t miss out on the opportunity to make this beautiful home your own!
6159 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$699,7452 Days on yellowkey MLS ID: G5111054
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2235 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria, an award-winning single-story, open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great room to the dining and kitchen areas, creating a bright and welcoming space for family and guests. The kitchen features an oversized island, ample counter space, and an open layout that connects directly to the living areas, making it perfect for everyday living and entertaining. The owner’s suite and additional bedrooms are thoughtfully placed to maximize privacy and comfort. Located in the brand-new Avalon Woods community, residents enjoy boutique-style charm just minutes from top-rated schools, Hamlin Town Center, Hwy 429, and Disney.
7562 SPRING VALLEY ST, WINTER GARDEN, FL 34787
$582,4902 Days on yellowkey MLS ID: G5111052
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2102 Built: 2026Monthly Fee: $140Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Berkley floorplan by Dream Finders Homes features 2,102 square feet of well-designed living space across two stories. This home includes 3 bedrooms, 3 full bathrooms, and a 2-car garage. The open-concept main floor boasts a spacious family room, dining area, and a modern kitchen with ample counter space—ideal for both daily living and entertaining. The primary suite is located on the first floor for added privacy, with a luxurious bath and walk-in closet. Upstairs, two additional bedrooms and a full bath provide flexible living options for guests or family members. Located near major roadways and just minutes from the shopping, dining, and entertainment options of Hamlin Town Center, Winter Garden Village, and Walt Disney World, Silverleaf offers the perfect balance of connectivity and tranquility. Orange County schools, including Hamlin Elementary, Hamlin Middle, and Horizon High School, enhance the appeal of this vibrant community.
6050 FLOWERING CHERRY BND, WINTER GARDEN, FL 34787
$712,6342 Days on yellowkey MLS ID: G5111051
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2515 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Carter, a thoughtfully designed bungalow that combines style, comfort, and modern functionality. This brand-new home offers 4 bedrooms, 3.5 bathrooms, and 2,520 sq. ft. of living space. The inviting front porch creates charming curb appeal, while inside, abundant natural light enhances the open-concept layout. The first floor features a bedroom with private bath, perfect for guests or multi-generational living, while the upstairs showcases spacious secondary bedrooms and a well-appointed primary suite. Outdoor living shines with a covered breezeway and private courtyard, ideal for gatherings, dining, or quiet relaxation. Located in Avalon Woods, residents will enjoy proximity to top-rated schools, Hamlin Town Center, Hwy 429, and Disney, all just minutes away.
15142 TEA TREE DR, WINTER GARDEN, FL 34787
$858,1202 Days on yellowkey MLS ID: G5111049
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3498 Built: 2026Monthly Fee: $150 Tax: $298 (2025)Community: Avalon WoodsSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Venice is a two-story home designed for efficient and flexible living. The first floor features an open-concept layout with a centrally located kitchen overlooking the dining area and main living space. The primary bedroom is located on the main level and includes a walk-in closet and en-suite bathroom, offering privacy and convenience. A flex room with walk in closet and a half bathroom are also located on the first floor, along with direct access to the garage and additional storage. The second floor includes additional secondary bedrooms with access to full bathrooms, a central loft providing flexible living space, and a dedicated laundry area. A secondary primary bedroom is also located on the second floor, featuring its own en-suite bathroom and walk-in closet, making it ideal for multi-generational living or extended stays.
18191 CIDER MILL LN, WINTER GARDEN, FL 34787
$470,5002 Days on yellowkey MLS ID: O6399312
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1817 Built: 2025Monthly Fee: $190 Tax: $1,424 (2025)Community: WaterleighSpa: NoTownhouse
Taxes:$1,424
Remarks: Under Construction. Waterleigh presents the Sandhill. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As we head upstairs, you are greeted with a loft area. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Sandhill includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *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)
13536 SUNSET LAKES CIR, WINTER GARDEN, FL 34787
$1,200,0001 Day on yellowkey MLS ID: O6399227
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3389 Built: 1998Monthly Fee: $69 Tax: $10,940 (2025)Community: Sunset LakesSpa: YesSingle Family
Taxes:$10,940
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including the Primary Bedroom), with the 5th Bedroom, a full bath and a bonus loft located on the second level. Inside, the home features designer ENGINEERED HARDWOOD FLOORING throughout the main living areas and the downstairs primary suite. The CHEF'S KITCHEN is a showpiece, boasting THREE SLABS OF PERMIUM CALCUTTA QUARTZ, an ITALIAN MARBLE BACKSPLASH, 60-inch DOUBLE-STACKED ALL WOOD SHAKER CABINTRY, a handy FOOD PREP ISLAND, a BREAKFAST BAR and TOP-OF-THE-LINE SAMSUNG APPLIANCES! The family room features AUTOMATIC ROLLER SHADES and is open to the kitchen and features Cathedral ceilings, a huge picture window and French Doors to the inviting lanai and sparkling pool. The primary suite is a retreat of its own, offering a FULLY-RENOVATED, SPA-INSPIRED bathroom with floor to ceiling CALCUTTA TILE, a frameless glass shower, a freestanding soaking tub, tall custom cabinetry with WHITE EXOTIC CARERRA QUARTZ COUNTERS and a massive walk-in closet! Architectural details elevate every room, including Plantation Shutters, multiple sets of French Doors, tray ceilings, volume and cathedral ceilings, extensive crown molding, transom windows, recessed lighting, bead boarding and elegant custom millwork. Step outside to a stunning outdoor oasis. The completely remodeled pool and spa area is surrounded by 2100 sq. ft. of travertine decking that extends across the covered lanai and additional outside patio space—perfect for entertaining! The lanai ceiling is finished with tongue and groove wood planks, adding warmth and sophistication. Other major upgrades include NEW DOUBLE-PANE, THERMAL WINDOWS (2023), a 2019 ROOF a 2019 AC SYSTEM and rain gutters. The extended brick paver driveway and matching walkway enhance curb appeal, while the well-fed irrigation system coupled with the well water (filtered by the whole house WATER SOFTENER) help keep utility costs low. All of this is just 5 minutes from the 429, offering quick access to Orlando and surrounding areas. Downtown Winter Garden & Winter Garden Village are also nearby as well as numerous championship golf courses for all your shopping, dining and recreational needs! Nearby top-rated schools are just another plus! Call for your showing today if you want to be the lucky one to snag this one-of-a-kind home before someone else does!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Diane Sterling (407-761-0512)
15359 MARITIME PINE DR, WINTER GARDEN, FL 34787
$828,1053 Days on yellowkey MLS ID: G5110994
0 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 2026Monthly Fee: $150Community: Avalon WoodsSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. 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!
15058 SAWGRASS BLUFF DR, WINTER GARDEN, FL 34787
$579,9002 Days on yellowkey MLS ID: O6396640
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: 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 is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Lauren Marason (610-223-7086)
5685 SURPRISE LILY DR, WINTER GARDEN, FL 34787
$685,000182 Days on yellowkey MLS ID: O6353593
1 Days Off yellowkey (back on 2/4/2026)
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2902 Built: 2021Monthly Fee: $80 Tax: $513 (2024)Community: Hamilton Gardens Ph 2A & 2BSingle Family
Taxes:$513
Remarks: Short Sale. Bank Approved Price! Welcome to this meticulously maintained 5-bedroom, 2.5-bath home in the sought-after Hamilton Gardens Community. Designed for modern living, this home offers an open-concept layout where the kitchen seamlessly flows into the dining area and spacious family room, perfect for both everyday life and entertaining. The modern kitchen is a chef's delight, featuring Stainless Steel Appliances, a Gas Range, Granite Countertops, and a large island. The first floor also includes a formal dining room and Flex Room ideal for a home office, bedroom or den. Upstairs, we have a versatile loft, a spacious primary suite with a huge walk-in closet, dual vanities, a soaking tub, and a separate shower, plus three additional bedrooms bathroom and conveniently located Laundry Room. Enjoy thoughtful upgrades like a Water Softener, Water Treatment System, and Tankless Water Heater for ultimate efficiency. The fully fenced backyard comes equipped with water and gas lines ready for your Outdoor Kitchen. Residents enjoy fantastic community amenities, including a pool, playground, dog park, and soccer field. Located in the desirable Hamlin area of Winter Garden, this home is just minutes from Hamlin Town Center's shopping, dining, and entertainment, top-rated Orange County schools, the 429 Expressway, and a short drive to Walt Disney World and other Orlando attractions.
Listing is courtesy of: CENTURY 21 CARIOTI (407-770-0322)
Listing Agent: Kavita Uttamchandani (239-691-2289)
14050 FAIRWAY WILLOW LN, WINTER GARDEN, FL 34787
$749,00024 Days on yellowkey MLS ID: O6392994
REDUCED by $46,000 (5.8%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2027 Built: 1989Monthly Fee: $322 Tax: $4,924 (2025)Community: Woodbridge On GreenSingle Family
Taxes:$4,924
Remarks: Welcome to this beautifully maintained home in the highly sought-after Woodbridge on the Green community, overlooking West Orange Country Club and perfectly situated in the hub of Winter Garden. This waterfront home offers a blend of comfort, style, and convenience—ideal for anyone looking to enjoy the best of Central Florida living. Step inside to an inviting, light-filled layout featuring spacious living areas, high ceilings, and thoughtfully designed spaces that make everyday living effortless. The kitchen offers generous counter space, ample cabinetry, and a functional layout perfect for cooking, entertaining, or gathering with family. The primary suite provides a peaceful retreat with a well-appointed bathroom and plenty of closet space. Additional bedrooms are comfortably sized and versatile—ideal for guests, a home office, or a growing household. Outside, enjoy a very large private backyard on the pond, with room to relax, garden, or entertain. New concrete tile roof was installed in 2023. Woodbridge on the Green is known for its mature landscaping (fully HOA maintained), quiet streets, and welcoming atmosphere; the HOA also covers house painting on a rotating schedule, helping to ensure an immaculate community aesthetic. Located just minutes from Windermere, top-rated schools, major highways, and the charming Historic Downtown Winter Garden, this home offers unmatched convenience with shopping, dining, and entertainment right at your fingertips. This is a wonderful opportunity to own a home in one of Winter Garden’s most desirable neighborhoods—move-in ready and full of potential.
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Drew Ross (407-383-6497)
1035 CHASE DR, WINTER GARDEN, FL 34787
$465,0007 Days on yellowkey MLS ID: O6396474
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1793 Built: 1995Monthly Fee: $44 Tax: $3,337 (2025)Community: Island Pointe SubSpa: NoSingle Family
Taxes:$3,337
High School: Ocoee High
Remarks: Under contract-accepting backup offers. Welcome to a home that feels right the moment you arrive. Set beneath the shade of mature oak trees on a 100-foot-wide lot in Winter Garden’s golf cart district, this beautifully maintained single-story home in Island Pointe invites you to slow down, breathe a little deeper, and truly enjoy where you live. The wide, covered front porch stretches across the entire front of the home, creating the perfect place for morning coffee, evening conversations, and everything in between. Step inside and you’re greeted by soaring vaulted ceilings and natural light that pours in from every angle, giving the home an open, airy feel that lives larger than its footprint. The layout flows effortlessly with multiple living and dining spaces designed for both connection and flexibility. At the center of it all is a generously sized kitchen with abundant counter space and a center island that opens seamlessly to the family room. This is where life happens. Holidays, casual dinners, and late-night conversations all find their place here. The split floor plan offers privacy and comfort. The owner’s suite is tucked away and serves as a peaceful retreat with a walk-in closet and a spacious en-suite bath featuring dual sinks, a garden tub, and a separate shower. On the opposite side of the home, two additional bedrooms provide the ideal setup for family, guests, or a home office. This home has been lovingly cared for and offers something buyers are always searching for but rarely find: solid construction with major system updates already done, including a newer roof, updated HVAC, and a brand new water heater. The finishes reflect its original character, giving you the opportunity to modernize at your own pace and build meaningful equity along the way. But what truly sets this home apart is the lifestyle. Located in the highly sought-after Golf Cart District of historic Downtown Winter Garden, you are just minutes from everything that makes this area so special. Hop on your golf cart or bike and head to Plant Street where you’ll find charming boutiques, incredible dining, live music, festivals, and the beloved Saturday Farmers Market. Enjoy local favorites like Crooked Can Brewery and Food Hall and Scoops Ice Cream only a quick ride away. Spend your weekends exploring the West Orange Trail or relaxing at nearby Newton Park, the City Pool, playground, fishing pier, and public boat ramp. Whether it’s a morning ride, an afternoon on the water, or an evening out, everything you need is right at your fingertips. Daily convenience is just as impressive, with multiple grocery options nearby and shopping along Highway 50. You are also close to top-rated schools, Winter Garden Village, AdventHealth, and have easy access to the 429 and Florida Turnpike. All of this, paired with low HOA dues and a welcoming, established neighborhood, makes this home not just a great purchase, but a smart investment in both lifestyle and long-term value. Homes like this do not come around often. A single-story layout, a prime location, strong bones, and the chance to make it truly your own. Come see it in person. Walk the space. Feel the openness. Sit on the front porch and imagine life unfolding here.
Listing is courtesy of: UPWELL REALTY LLC (407-926-9960)
Listing Agent: Kyle Madorin Pa (407-504-9247)
15162 SPINNAKER COVE LN, WINTER GARDEN, FL 34787
$825,00021 Days on yellowkey MLS ID: O6393190
REDUCED by $25,000 (2.9%) on 04/05/2026
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
Remarks: One or more photo(s) has been virtually staged. Discounted Interest Rates Available Nestled on a premier 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 over the last two years with modern updates, ensuring a move-in-ready experience for today’s discerning buyer. Inside, the open-concept layout is anchored by a gourmet kitchen featuring quartz countertops, a central island, and 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 high-end 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)
14267 AVENUE OF THE GRVS, WINTER GARDEN, FL 34787
$350,00031 Days on yellowkey MLS ID: O6390455
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1289 Built: 2008Monthly Fee: $139 Tax: $3,450 (2025)Community: Signature Lks-Pcl 01D Ph 01Townhouse
Taxes:$3,450
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Welcome to this beautifully maintained townhome in the highly desirable Independence community in Winter Garden! This home features 2 bedrooms and 2.5 bathrooms, with both bedrooms offering their own en-suite bathrooms, making it a comfortable and functional layout. Inside, you’ll find several thoughtful updates throughout. The first floor features tile flooring, while the second floor has been updated with luxury vinyl plank flooring. The stairs feature real wood, and custom-fit window shutters on every window add both style and privacy while still letting in plenty of natural light. Out back, you’ll find a spacious paver patio, perfect for relaxing or entertaining. Living in Independence means access to fantastic community amenities, including two pools and two fitness centers. The HOA also covers cable, internet, exterior maintenance, and the roof was recently replaced, adding extra peace of mind for the next owner. The location is another major highlight. You’re just minutes from Hamlin Town Center for shopping, dining, and entertainment, and less than 5 miles from Walt Disney World property, making it easy to enjoy everything the area has to offer while still living in an established neighborhood.
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Carly Ruecker (727-776-7962)
14423 WABASSO LOOP, WINTER GARDEN, FL 34787
$899,999100 Days on yellowkey MLS ID: O6368408
1 Days Off yellowkey (back on 4/15/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3630 Built: 2023Monthly Fee: $217 Tax: $12,742 (2024)Community: Tilden Place/Winter GardenSingle Family
Taxes:$12,742
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Remarks: Under contract-accepting backup offers. PRICED TO SELL! Welcome home to this stunning two-story residence in the gated community of Tilden Place, ideally located in the heart of Winter Garden. Just minutes from Winter Garden Village with its abundant shopping, dining, fast-casual options, hospital access, and everyday conveniences—and only a short drive to Walt Disney World Resort, this home offers the perfect blend of luxury, comfort, and location. Built by MI Homes, known for exceptional energy efficiency, this 5-bedroom, 4-bath home showcases sleek, modern upgrades throughout. The pavered driveway and porch set the tone, opening to a thoughtfully designed floor plan that includes a first-floor bedroom with a full bathroom, ideal for guests, multigenerational living, or a private home office. The main living areas feature LVP flooring, striking iron stair railings, and incredible custom trim work along the staircase. The gourmet kitchen will keep even the pickiest of chefs happy, featuring dark cabinetry that beautifully contrasts with a bright white waterfall island, pendant lighting, stainless steel appliances, gas cooking, and stunning upper cabinetry that elevates the space. A built-in pocket office offers the perfect spot for quick correspondence, bill pay, remote work, or a homework station. The family room is anchored by a dramatic wall of custom built-in shelving with accent lighting and a fireplace, creating a warm and inviting focal point for everyday living and entertaining. Upstairs, a spacious loft continues the custom design theme with floating shelves and integrated storage. The expansive upstairs primary suite features LVP flooring, generous space, and access to a private balcony, perfect for morning coffee or evening relaxation. With no rear neighbors, enjoy a private backyard retreat complete with an extended lanai, while the coastal-style balcony off the loft provides even more opportunities for entertaining and unwinding. The intimate gated community is centered around a beautiful pond with a fountain, and just a short walk down the street brings you to the community green space and playground. This stunning home truly offers modern luxury, functional living, privacy, and an unbeatable Winter Garden location. WELCOME HOME!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Amy Kidwell Pa (407-848-8042)
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