Location: Winter Garden
Keyword(s): Bridgewater Middle
Keyword(s) Middle School: Bridgewater Middle
Do Not Show Listings
14531 CEDAR HILL DR, WINTER GARDEN, FL 34787
$799,0007 Days on yellowkey MLS ID: O6408070
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3510 Built: 2014Monthly Fee: $187 Tax: $6,330 (2025)Community: Orchard Hills Ph 1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,330
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Welcome to 14531 Cedar Hill Dr., a stunning home located in the highly sought-after Orchard Hills community of Winter Garden. This spacious residence offers 5 bedrooms, 4 full bathrooms, and over 3,500 square feet of beautifully designed living space, perfect for both everyday living and entertaining. Enjoy a huge private backyard with no rear neighbors, creating a peaceful retreat ideal for relaxing or hosting gatherings. The expansive screened-in patio extends your living space outdoors, while inside you’ll find a massive loft/game room, perfect for movie nights, play space, or a home office setup. The oversized primary suite is a true sanctuary, featuring ample space to unwind and a luxurious en-suite bath. Additional bedrooms are generously sized, offering comfort and flexibility for family, guests, or multigenerational living. Residents of Orchard Hills enjoy resort-style amenities, including a sparkling pool, fitness center, dog park, playground, and barbecue area. Conveniently located near Horizon West and the popular Hamlin area, this home is just minutes from shopping, dining, entertainment, and downtown Winter Garden. This exceptional home combines space, privacy, and location—don’t miss the opportunity to make it yours!
Listing is courtesy of: REAL BROKER, LLC (407-922-8986)
Listing Agent: Denise Pellegrino (352-978-9720)
15615 HONEYBELL DR, WINTER GARDEN, FL 34787
$389,90010 Days on yellowkey MLS ID: O6406267
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1584 Built: 2017Monthly Fee: $418 Tax: $6,085 (2025)Community: Hamlin ReserveTownhouse
Taxes:$6,085
Elementary School: Independence Elementary
High School: Horizon High School
Remarks: Welcome to this beautifully updated townhome in the highly desirable Hamlin Reserve community of Winter Garden, offering the perfect blend of comfort, style, and low-maintenance living. This move-in ready home stands out from the competition with fresh interior paint and brand new flooring, creating a clean, modern feel from the moment you walk in. Featuring a functional and spacious layout, this property is ideal for both primary residence buyers and investors seeking a well-maintained home in a prime location. Bright, open living spaces flow seamlessly, making it perfect for everyday living and entertaining. Located in Hamlin Reserve, you’ll enjoy easy access to Hamlin Town Center, shopping, dining, and major highways, and you are just a short drive to Walt Disney World, making this area highly attractive for both homeowners and long-term investment potential. You’re also minutes from Horizon West and everything Winter Garden has to offer. As a townhome, it provides the benefit of lower maintenance compared to single-family homes, making it an excellent option for busy homeowners or those looking for a lock-and-leave lifestyle. With its recent upgrades, prime location, and standout condition, this home is a rare opportunity in today’s market. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Arturo Ortiz (407-502-8752)
6421 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787
$539,90076 Days on yellowkey MLS ID: O6386906
1 Days Off yellowkey (back on 3/24/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1863 Built: 2006Monthly Fee: $195 Tax: $6,426 (2024)Community: Signature Lks-Pcl 01BSingle Family
Taxes:$6,426
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Stop your search, this is the home you have been looking for! MOVE-IN READY, fully renovated, located at the well established master planned Independence Community, this stunning 3-bedroom, 2-bathroom residence looks like a model home! This open and split floor-plan offers both, comfort and functionality. Fully upgraded, this home features new LUXURY VINYL flooring, new kitchen and bathrooms with QUARTZ COUNTERS, fresh interior paint, a UPDATED ROOF, a NEW AC SYSTEM, and an ELECTRIC VEHICLE CHARGER and a very charming FULLY FENCED BACKYARD. The bright and integrated living spaces are enhanced by LARGE WINDOWS and abundant NATURAL LIGHT, creating a warm and inviting atmosphere throughout. The modern kitchen showcases QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, and AMPLE CABINETRY seamlessly connecting to the living and dining areas—perfect for everyday living and entertaining. The thoughtfully designed SPLIT FLOORPLAN provides added privacy to the primary suite, while the additional bedrooms provide flexibility for a variety of needs. Spacious primary suite with an ensuite bathroom that features a spa-like GARDEN TUB with separate shower, DUAL VANITIES and a large WALK-IN CLOSET, fully customized. Step outside to a CHARMING FENCED BACKYARD, providing privacy and a wonderful space to relax or entertain. Among so many standout features it is its PRIME LOCATION. It faces a CONSERVATION AREA, POND, and a SCENIC WALKING TRAIL offering peaceful views and easy access to outdoor enjoyment. Residents of this home enjoy opening their front door this beautiful green space and stepping right into the scenic trail for easy morning or evening walks. Experience resort-style living in Independence! Two clubhouses, pools, fitness centers, tennis & basketball courts, trails, and dog parks. Playgrounds, scenic lakes, private boat ramps and community events all year round. Close to shopping, dining, and SR-429 — the perfect blend of comfort, recreation, and convenience. Enjoy FREE INTERNET and up to 3 CABLE connexions, already included on the HOA fee. This is an exceptional opportunity for buyers seeking a truly turnkey residence & the vibrant Winter Garden Lifestyle! Schedule your showing today!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Francine Arroyo Santowski (407-436-4910)
6524 PASTURELANDS PL, WINTER GARDEN, FL 34787
$505,000119 Days on yellowkey MLS ID: S5141842
0 Days Off yellowkey (back on 4/17/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2328 Built: 2005Monthly Fee: $285 Tax: $4,804 (2025)Community: Signature LakesTownhouse
Taxes:$4,804
Remarks: One full year of ***AHS HOME WARRANTY**This townhome is located in a highly desirable community offering exceptional amenities and long-term value. Featuring 4 bedrooms and 3 full bathrooms, this beautifully upgraded residence stands out with a spacious first-floor bedroom and full bath providing convenience, accessibility, and privacy ideal for guests, multigenerational living, or anyone wishing to avoid stairs. From the moment you arrive, the charming front porch invites you to relax while enjoying peaceful water views. Inside, a spacious formal living and dining room combination showcases elegant wall moldings and refined window trim, creating a warm and inviting atmosphere. Waterproof luxury laminate flooring flows throughout the home, offering both durability and modern style. The first-floor bathroom has been fully remodeled and features a walk-in shower with a rain shower head, marble-look tile walls, glass enclosure, modern lighting, new toilet, and tile flooring.The open layout continues into the gourmet kitchen, equipped with high-end stainless steel appliances, including a Viking range and microwave, a newer three-door Bosch refrigerator, and dishwasher. Granite countertops, ample cabinetry, under-stair storage, and space for casual dining make this kitchen perfect for both everyday living and entertaining. A nearby modern laundry room includes LG stainless steel washer and dryer with pedestal bases designed for comfort and ease of use.The staircase makes a striking impression with elegant wood steps and a matching handrail, leading to the second level where French doors open to a generously sized primary suite filled with natural light. The spa-inspired primary bathroom features a walk-in shower, separate soaking tub, and abundant space. Two additional bedrooms and a full bathroom complete the upper floor. Recent updates include fresh interior paint and a new roof installed in 2024.The rear-entry two-car garage is complemented by a patio area that can easily be fenced to create added privacy or a secure outdoor space for pets. The well-managed HOA includes cable, high-speed internet, and ground maintenance, with exterior painting of the townhomes scheduled soon. Residents enjoy an active, welcoming community with walking trails, a swimming pool, fitness center, and park. Ideally located near top-rated schools, shopping, dining, theme parks, and major attractions, this property offers an exceptional opportunity to own or invest in a location that continues to grow in demand. This home must be seen to be fully appreciated. Schedule your private showing today and take the next step toward securing a property that truly delivers on comfort, lifestyle, and value.
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Maritza Jimenez (407-579-8972)
7104 TICKLEGRASS ST, WINTER GARDEN, FL 34787
$1,100,000303 Days on yellowkey MLS ID: O6329696
REDUCED by $146,000 (11.7%) on 05/12/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3347 Built: 2014Monthly Fee: $195 Tax: $552 (2024)Community: Signature Lakes Parcel 1DSpa: YesSingle Family
Taxes:$552
Remarks: SELLER MOTIVATED! Seller is offering a concession of up to $10,000 toward Buyer Pre-paids and Closing costs. Welcome to your dream oasis! This stunning 5-bedroom, 3.5-bath single-family home on Lake Hancock is a true masterpiece, offering the ultimate in luxury and comfort. With a contemporary design and exceptional features, this residence is a rare gem in the world of real estate. Upon entering this exquisite residence, you'll find a spacious living room and an elegant dining room, both thoughtfully designed for special occasions and entertaining. Continuing through the home, you'll be greeted by an exquisite open floor plan that seamlessly connects the kitchen, complete with top-of-the-line appliances, to the inviting family room. This perfect layout ensures that you're never far from the action, whether you're preparing a gourmet meal or enjoying quality time with family and friends. Natural light pours in through retractable sliding doors, creating an indoor-outdoor experience like no other. These doors lead to a captivating saltwater infinity pool and spa, perfect for relaxing on warm days or entertaining under the stars. With five generously sized bedrooms, there's plenty of space for your family and guests. The master suite is a sanctuary, featuring a spacious walk-in closet and an ensuite bath with all the luxurious amenities you deserve. Situated on a large corner lot, the property offers privacy and ample outdoor space for gardening, play, or simply basking in the sun. Your options are endless when it comes to creating your own outdoor paradise. This residence is not just a home; it's a lifestyle. Experience the epitome of elegance and modern living in every corner of this property. This home is just minutes from top-rated schools, shopping, dining, and moments away from the enchantment of Disney and Orlando's premier attractions.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: Michele Acosta Gladding (407-963-6431)
5637 WATER ROSE RD, WINTER GARDEN, FL 34787
$419,490126 Days on yellowkey MLS ID: O6373923
REDUCED by $500 (0.1%) on 04/30/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1617 Built: 2016Monthly Fee: $393 Tax: $5,741 (2025)Community: IndependenceSpa: NoTownhouse
Taxes:$5,741
Remarks: ***WINDERMERE HIGH SCHOOL*** Price improvement – great opportunity in Signature Lakes / Winter Garden. Enjoy the best of Florida living in this beautiful townhome located in the highly desirable Signature Lakes / Independence community in Winter Garden. *Seller offering $4,490 toward buyer’s closing costs — great opportunity to reduce out-of-pocket expenses!* This well-maintained 3-bedroom, 2.5-bath home offers a functional layout with comfortable living spaces and plenty of natural light. The kitchen opens to the living and dining areas, creating the perfect space for everyday living and entertaining. Step outside to a private screened patio, ideal for relaxing, enjoying your morning coffee or hosting friends while taking advantage of Florida’s outdoor lifestyle. Residents of Signature Lakes enjoy resort-style amenities, including community pools, walking trails, parks, playgrounds and beautiful lakes throughout the neighborhood. Conveniently located just minutes from Disney, shopping, dining and top-rated schools, this home offers both comfort and an unbeatable location. A great opportunity to own in one of Winter Garden’s most sought-after communities. Seller is offering a generous $4,990 contribution toward the buyer’s closing costs, a great opportunity to help reduce your upfront expenses and make homeownership even more affordable! Schedule your private showing today.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Luciana Amorim Panajotti (917-853-0353)
1711 AMSEL FALLS PARK TER, WINTER GARDEN, FL 34787
$1,000,000222 Days on yellowkey MLS ID: O6346377
0 Days Off yellowkey (back on 5/8/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3863 Built: 2017Monthly Fee: $180 Tax: $10,792 (2024)Community: TwinwatersSingle Family
Taxes:$10,792
Elementary School: Hamlin Elementary
High School: West Orange High
Remarks: Under contract-accepting backup offers. Welcome to this stunning architectural masterpiece nestled in the heart of Twinwaters, one of Winter Garden’s most sought-after communities. This elegant two-story home seamlessly blends sophistication and comfort, offering over 3,600 square feet of beautifully designed living space. Step through the grand entryway to find soaring ceilings, expansive windows that fill the home with natural light, and designer finishes that exude contemporary luxury. The gourmet chef’s kitchen is a true showpiece—featuring 42” custom cabinetry, gleaming quartz countertops, a massive entertainment island, stainless steel appliances, and a walk-in pantry, perfect for culinary enthusiasts and family gatherings alike. The open-concept great room flows effortlessly into a spacious dining area and covered lanai, ideal for both indoor and outdoor entertaining. Upstairs, the luxurious primary suite offers a serene retreat with a spacious walk-in closets, a spa-inspired bathroom with a deep soaking tub, frameless glass shower, and dual vanities. A versatile loft provides additional space for a home theater, gym, or play area, while the first-floor guest suite ensures comfort and privacy for visitors. The private backyard invites you to create your own oasis—whether adding a pool, summer kitchen, or lush garden escape. Enjoy resort-style amenities including a community pool, playground, and picturesque walking trails, all surrounded by pristine lakes and lush landscaping. Twinwaters is ideally situated near Horizon West, top-rated schools, fine dining, boutique shopping, and major highways for an easy commute to downtown Orlando and world-famous attractions. This home truly embodies the ultimate blend of luxury, location, and lifestyle—a rare opportunity to live beautifully in one of Central Florida’s premier communities.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Jay Winston (407-497-1112)
8156 WOOD SAGE DRIVE, WINTER GARDEN, FL 34787
$449,00071 Days on yellowkey MLS ID: V4947783
REDUCED by $10,000 (2.2%) on 04/30/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1853 Built: 2018Monthly Fee: $315 Tax: $3,792 (2025)Community: SummerlakeTownhouse
Taxes:$3,792
Remarks: Winter Garden – Rare, immaculate end-unit townhome in highly sought-after Summerlake, fully updated and truly MOVE-IN READY. Step onto the charming front porch—perfect for morning coffee as the neighborhood comes to life—and then into a bright, open interior with soaring ceilings, a freshly painted interior, and an inviting floor plan. The chef’s kitchen features abundant real wood cabinetry, upgraded granite countertops, and a cozy eat-in area, all overlooking a spacious family room ideal for gatherings. Large windows fill the space with natural light and frame your private rear courtyard—an outdoor area with serious potential. Think Italian courtyard villa vibes: brick pavers, twinkling lights, lush greenery, and maybe that pizza oven you’ve been dreaming about. The courtyard serves as a true extension of your living space, whether you envision a gardener’s paradise, a peaceful retreat, or a stylish entertaining area. Beyond the courtyard, you’ll find a generous 2-car garage, perfect for vehicles and extra storage. Upstairs, the home offers 3 bedrooms and 2.5 baths, all meticulously maintained, including NEW carpet upstairs and tasteful updates throughout. Living in Summerlake means more than owning a home—it’s a lifestyle. With top-tier amenities, nearby shopping, dining, and everything Winter Garden has to offer, this is the perfect place to call home.
Listing is courtesy of: APARO-GRIFFIN PROPERTIES INC (386-738-2845)
Listing Agent: Kathy Aparo-Griffin (386-748-0173)
4122 SHEPPERDS HOLLOW ALY, WINTER GARDEN, FL 34787
$549,990140 Days on yellowkey MLS ID: O6370363
1 Days Off yellowkey (back on 5/8/2026)
REDUCED by $5,000 (0.9%) on 05/04/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2459 Built: 2021Monthly Fee: $281 Tax: $8,150 (2024)Community: Enclave/HamlinSingle Family
Taxes:$8,150
Remarks: Under contract-accepting backup offers. Income producing opportunity! This home includes a private one-bedroom garage apartment with separate entrance and kitchenette. Welcome to the Enclave at Hamlin, one of Winter Garden’s desirable communities, featuring the popular Taylor Morrison Ashwood floor plan that blends style, space and versatility. This beautifully designed two-story home offers two bedrooms, 2.5 baths, a spacious loft that can be converted into a third bedroom and a private one-bedroom with kitchenette garage apartment, providing exceptional flexibility for multi-generational living, guests or potential rental income. Upon entry, you are greeted by a welcoming foyer that opens into an expansive great room, ideal for entertaining and everyday living. Overlooking the space is the gourmet kitchen, complete with a large island, quartz countertops, stainless steel appliances and ample cabinetry. The kitchen flows seamlessly to the covered lanai, creating an ideal indoor-outdoor living experience. Also on the first floor is versatile flex space that can be used as a home office, formal dining room or additional bedroom. Upstairs, the primary suite serves as a private retreat, featuring a spa-inspired bath with dual quartz vanities, a walk-in shower, private water closet and a generous walk-in closet. The second floor also includes a secondary bedroom, a full bath with tub/shower combination, a private laundry room and a loft with built-in features, ideal for a playroom, craft room, media space or easily converted bedroom. Adding tremendous value is the one-bedroom, one-bath garage apartment with kitchenette, walk-in closet and private entrance, offering an excellent income opportunity or private accommodations for guests or family. The HOA maintains the lawn, including areas inside the fenced yard, providing a low-maintenance lifestyle. Community amenities include a resort-style pool with cabana overlooking Lake Hartley, a tot lot and peaceful open recreation areas with benches positioned to capture scenic lake views. The location is exceptional, with a quick half-mile experience, bike ride or visit to Hamlin, a vibrant 900-acre destination featuring a luxury theater, shopping, dining, salons, waterfront restaurants and entertainment. Convenient access to SR 429, theme parks, and major roadways makes commuting easy. Residents will also enjoy being within distance of the anticipated Horizon West Regional Park, a 215-acre destination park under development. Once complete, the park will offer miles of scenic trails, playgrounds, picnic pavilions, open green spaces, a splash pad, lake access for kayaking and community event areas, delivering an outstanding outdoor lifestyle right outside your door. This home offers a combination of comfort, convenience and future-forward living in one of Winter Garden’s fastest-growing areas.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-581-7888)
Listing Agent: Teresa White (904-994-9075)
16136 WIND VIEW LN, WINTER GARDEN, FL 34787
$587,900134 Days on yellowkey MLS ID: O6372050
1 Days Off yellowkey (back on 5/7/2026)
REDUCED by $21,100 (3.5%) on 05/04/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2291 Built: 2016Monthly Fee: $341 Tax: $92,223 (2025)Community: Waterleigh Ph 1BSingle Family
Taxes:$92,223
Elementary School: Water Spring Elementary
Remarks: Under contract-accepting backup offers. Beautiful Waterfront 4-3 home in Waterleigh with large green space in front of the home and INCREDIBLE pond and lake views in back. This desirable Calder model is a 1 story home and offers 4 bedroom, 3 baths, plus a den/office with many upgrades and great views. The front drive and walkway are paved and lead up to a large porch with a peaceful view of a wide green space with mature trees. The home is detailed with tall ceilings and 8-foot, 6 panel decor doors throughout, recessed tray ceilings, elegant arches, and a tasteful light beige-colored walls throughout. Décor tile floor through the main home, and beautiful wood floor style plank tile in all bedrooms. The Designer kitchen has moco-colored, tiered, 42-inch cabinets with crown molding and under cabinet lights to accent the tumbled marbled backsplash, café` series kitchen stainless-steel appliances, and accented by gorgeous granite counters. It offers a glass top stove, French door fridge with bottom freezer, large walk-in pantry, and large sink island with breakfast bar, lite with pendant lights overlooking the family and dining area. The family room sliding door leads out to a covered and screened lanai with incredible serene water views. A second patio is outside for the cooler days to soak up the sun. The Primary Bedroom has water views, tray ceiling with fan and recessed lighting. The Primary bathroom has a walk-in shower with glass enclosure, a large 8x9 ft walk-in closet, separate linen closet, separate toilet room and dual sink vanity with extra storage. The floor plan splits the primary bedroom away from the secondary bedrooms for privacy. Two bedrooms share a jack and jill bath with dual sinks and separate toilet and tub room for more efficient use. The 4th bedroom shares a hall bath near the laundry. The laundry room provides a washer and dryer installed and many cabinets and granite counters for storage. The office/den/flex room also faces the back with the awesome water views. All bedrooms, living room, and den/office/flex room all have ceiling fans. Lawn care is included in the HOA fees. This amazing home is in the highly desirable community “Waterleigh.” Located just off the 429 west of Disney, This community amenities include 3 resort style pools, 2 fitness gyms, club houses, putt-putt golf, dog park, huge sports fields, playground, beach volleyball, Tennis, lake dock and view BBQ/picnic area, with walking paths and exercise stations that wind around the scenic lakes, nature, and community for a relaxing and enjoyable lifestyle. Fast and easy access anywhere. Hospitals, restaurants and shopping are all close and many more are being built nearby. Great schools; Water Spring Elementary, Water Spring Middle, and Horizon Highschool. All information here is deemed reliable but not guaranteed. Please email for more information or to get started in making this incredible home, YOUR home.
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Bryce Rysewyk (407-340-1754)
7187 WILD STRAWBERRY RUN, WINTER GARDEN, FL 34787
$723,00019 Days on yellowkey MLS ID: O6403837
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3602 Built: 2007Monthly Fee: $200 Tax: $11,214 (2025)Community: Signature Lks-Pcl 01D Ph 02Spa: NoSingle Family
Taxes:$11,214
Remarks: There are homes that simply check the boxes… And then there are homes that instantly make you feel something the moment you walk through the door. This former model home tucked inside one of Winter Garden’s most loved communities, Independence. From the soaring ceilings to the warm engineered wood floors flowing throughout the home, every space feels bright, open, and inviting. Picture slow mornings in the beautiful open kitchen with granite countertops and beautiful color cabinetry while sunlight pours into the living spaces. Imagine family gatherings that effortlessly flow from the spacious living room to the dining area, creating the perfect setting for birthdays, holidays, movie nights, and everyday moments that matter most. The layout was designed for real life and comfort. Downstairs, the private primary suite creates a peaceful retreat, while the additional guest suite and the office flexibility for multigenerational living, remote work, or welcoming visitors. Upstairs opens into oversized bedrooms, a Jack and Jill bathroom, and a huge bonus space ready for game nights, a media room, or a second family lounge. But what truly makes this home special is the lifestyle waiting right outside your front door. Located in the highly desirable Independence community in Winter Garden, residents enjoy one of Horizon West’s most vibrant master planned communities filled with scenic walking and biking trails, beautifully maintained green spaces, community parks, playgrounds, clubhouses, fitness centers, resort style pools, and sports courts. Top rated schools, shopping, restaurants, Outside, life becomes even better. Disney just minutes away create the kind of Florida lifestyle.
Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)
Listing Agent: Carmelo Nuccio (321-441-6951)
5755 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$455,00019 Days on yellowkey MLS ID: O6404161
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1797 Built: 2019Monthly Fee: $338 Tax: $4,506 (2025)Community: Orchard Hills Ph 4Townhouse
Taxes:$4,506
Remarks: Welcome to this beautifully maintained corner townhouse in the sought-after Orchard Hills community of Winter Garden, offering 3 bedrooms, 2.5 baths, a 2-car garage, and abundant natural light throughout. As you enter the home, you are welcomed into the dining area which then flows seamlessly into the spacious living room and kitchen, creating an inviting layout perfect for everyday living and entertaining. Tile flooring extends throughout the downstairs living areas, kitchen, and wet areas for style and easy maintenance. The kitchen features stunning granite countertops that contrast beautifully with the white cabinetry, along with stainless steel appliances all included. Upstairs, you’ll find all three bedrooms with comfortable carpet flooring, as well as a convenient laundry room complete with washer and dryer. The primary bedroom offers private access to a balcony where you can enjoy peaceful water views and relax in a serene outdoor setting. Residents of Orchard Hills enjoy exceptional amenities including a clubhouse, fitness center, picnic area with grills, dog park, playground, and a vibrant community atmosphere with events and social clubs designed to build lasting relationships.
Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)
Listing Agent: Francisco Nieves-Taranto (321-248-4149)
15524 AVIATION ALY, WINTER GARDEN, FL 34787
$560,00041 Days on yellowkey MLS ID: O6398331
0 Days Off yellowkey (back on 5/6/2026)
REDUCED by $10,000 (1.8%) on 04/29/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2414 Built: 2015Monthly Fee: $328 Tax: $8,711 (2025)Community: Overlook 2/Hamlin Ph 1 & 6Single Family
Taxes:$8,711
Remarks: Welcome home to this updated 3 bedroom, 3.5 bath urban cottage in The Cove at Hamlin with large covered front porch that overlooks a greenbelt. The home offers a bright and sunny 2-story foyer, an inviting kitchen with breakfast area, a large great room with recessed lighting, crown molding and a wall of sliders that open to the covered, screened lanai which allows for that indoor-outdoor Florida living. The kitchen offers 42” cabinets, granite countertops, stainless steel appliances, including a gas range, a large walk-in pantry and center island with space for stools. You will also find a guest bedroom suite with walk-in closet and full bath on the main level in addition to the half bath off the kitchen area. The owner’s suite is found on the second level and is highlighted by French doors, tray ceiling and large windows. The en-suite bathroom has duel sinks, large counter space, frameless glass shower and a walk-in closet with custom closet organizer. You will also find on the second level a quiet nook with a window (perfect for a desk), the third bedroom and bath and the laundry room with cabinets. Some of the additional upgrades in the home are 8’ doors, Plantation blinds, wrought iron bannister, crown molding and a tankless water heater. The exterior features a screened paved lanai, fenced yard, and new turf that was just added to the side yard. The home has a rear two car garage with ample ceiling storage racks. This sought after community is walkable to the Hamlin Town Center that features stores, restaurants, medical services and is highlighted by Popstroke miniature golf and the Cinepolis movie theater. The community offers a resort style pool with splash pad, clubhouse, fitness center, playgrounds and dog park and is located with easy access to SR429 and the Florida Turnpike. A bonus is the accessibility to Disney and nightly views of the fireworks throughout the community. Come make this your NEW home!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Nancy Foltz (703-772-0215)
15143 KIRSTY ALY, WINTER GARDEN, FL 34787
$659,000247 Days on yellowkey MLS ID: O6344886
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
Remarks: Under contract-accepting backup offers. 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)
3167 WINESAP WAY, WINTER GARDEN, FL 34787
$575,00030 Days on yellowkey MLS ID: O6400764
0 Days Off yellowkey (back on 4/30/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2115 Built: 2016Monthly Fee: $190 Tax: $5,408 (2025)Community: Orchard Pk/Stillwater XingSingle Family
Taxes:$5,408
Remarks: Under contract-accepting backup offers. Welcome to 3167 Winesap Way, a beautifully appointed home nestled in the highly sought-after Orchard Park community of Winter Garden. This thoughtfully designed residence offers the perfect blend of comfort, efficiency, and modern style, featuring a spacious open-concept floor plan ideal for both everyday living and entertaining. Located minutes away from top Windermere Schools, Grocery stores, Shopping and entertainment, this home give you all you need right at your door. Enjoy energy efficiency and peace of mind with solar panels, a Tesla charger, Tesla power banks, and a reliable hurricane backup power system. Inside, the home showcases seamless flow between the living, dining, and kitchen areas, all filled with natural light and designed for today’s lifestyle. Step outside to your own private retreat, complete with a dedicated outdoor entertaining area and a cozy fire pit—perfect for relaxing evenings or hosting friends and family on beautiful Florida nights. With its combination of sustainable features, functional layout, and inviting indoor-outdoor living spaces, this home presents a rare opportunity to enjoy both luxury and practicality in one of Winter Garden’s most desirable neighborhoods.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Andrew Tinkler (407-595-9581)
5340 BOWMAN DR, WINTER GARDEN, FL 34787
$2,195,00038 Days on yellowkey MLS ID: O6398618
0 Days Off yellowkey (back on 5/1/2026)
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 5749 Built: 2017Monthly Fee: $230 Tax: $16,854 (2026)Community: The Cove At HamlinSingle Family
Taxes:$16,854
Tax Year: 2026
Remarks: Under contract-accepting backup offers. Lakefront living, done at scale. Set along approximately 160 feet of shoreline on Lake Hancock, this five-bedroom, six-and-a-half-bath residence delivers expansive water views, refined finishes, and a layout designed for both everyday living and effortless entertaining. From the moment you enter, soaring ceilings, arched architectural details, and wide-plank hardwood floors create a sense of openness and flow. A wall of arched windows floods the home with natural light and draws your eye straight through to the lake beyond. At the center, a chef’s kitchen anchors the space—featuring a generous island, porcelain farm sink, custom cabinetry, glass tile backsplash, and a full suite of Wolf and Sub-Zero appliances. The kitchen opens seamlessly to the family room and breakfast area, all positioned to capture the view. The primary suite is tucked privately on the main level, offering a true retreat with tranquil lake views, a spa-style bath with soaking tub and walk-in shower, dual vanities, and an oversized closet. Upstairs, four additional bedrooms with en-suite baths are complemented by a spacious game room and dedicated media room—creating separation and flexibility for guests or family. Outdoor living is just as compelling. A covered lanai and upper-level balcony overlook the water, with ample space to design a custom pool and private dock. Located near Hamlin Town Center, Winter Garden Village, and major roadways, the home offers both convenience and a true waterfront lifestyle, with community amenities including a pool, fitness center, playgrounds, and dock access
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Steve Healy (407-230-1441)
14090 AVENUE OF THE GROVES, WINTER GARDEN, FL 34787
$339,00020 Days on yellowkey MLS ID: O6404288
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1116 Built: 2011Monthly Fee: $415 Tax: $2,320 (2025)Community: IndependanceTownhouse
Taxes:$2,320
Remarks: Tucked away in the sought-after community of Independence, this beautifully renovated 2-bedroom, 2.5-bath townhouse offers comfort, style, and an unbeatable location just minutes from Walt Disney World. Thoughtfully updated throughout, the home features stylish new flooring, fresh interior paint, modern lighting fixtures, and a brand-new roof—providing a truly move-in-ready experience. The inviting living area enjoys peaceful, unobstructed views with no front-facing neighbors, creating the perfect backdrop to enjoy the Magic Kingdom’s dazzling nightly fireworks. Ample guest parking is conveniently located directly in front of the home, adding to the everyday convenience. Step outside to a spacious backyard and enjoy the covered walkway leading to the two-car garage—an ideal combination of comfort and functionality. Residents of Independence enjoy access to two resort-style clubhouses featuring pools, state-of-the-art fitness centers, tennis and basketball courts, and playgrounds, offering endless opportunities for recreation and relaxation. The HOA includes internet, cable, exterior maintenance, grounds maintenance, and pest control, making this property an excellent choice as a primary residence, vacation home, or investment opportunity.
Listing is courtesy of: RE/MAX TOWN CENTRE (407-996-3200)
Listing Agent: Fernando Barragan (407-325-1085)
14844 DRIFTWATER DR, WINTER GARDEN, FL 34787
$429,99021 Days on yellowkey MLS ID: O6404258
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1990 Built: 2016Monthly Fee: $414 Tax: $7,051 (2025)Community: Signature Lakes Ph 3B-6Townhouse
Taxes:$7,051
Remarks: Welcome to this beautifully maintained townhome located in one of Winter Garden’s most desirable communities. Featuring 4 bedrooms, 2.5 bathrooms, and nearly 2,000 square feet of thoughtfully designed living space, this home delivers the comfort of a single-family residence with the convenience of low-maintenance living. The main floor offers a bright open layout with elegant tile flooring, a modern kitchen featuring granite countertops and 42" upper cabinets, and a spacious primary suite complete with a walk-in closet and private bathroom. Upstairs, you'll find three additional bedrooms and a flexible loft—perfect for a home office, media room, or play area. Step outside to a covered brick-paver patio and enjoy the expansive green lawn located just behind the home, creating the perfect space for outdoor fun, gatherings, or for kids to safely play. A private breezeway connects the home to a detached 2-car garage. The property is located near beautiful lakes and scenic walking areas, adding to the charm of this vibrant community. Residents also enjoy access to exceptional amenities, including resort-style pools, a clubhouse, fitness center, tennis and basketball courts, playgrounds, walking and biking trails, and a private boat ramp. Zoned for top-rated A-rated public schools, this home is just minutes from Hamlin Town Center, with Publix, Walmart, dining options, the new public library, and a picturesque lakefront park all close by. With its unbeatable location, family-friendly setting, and outstanding lifestyle offerings, this is a place you’ll be proud to call home.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Claudio Maciel (407-561-0108)
7766 MINUTEMEN LOOP, WINTER GARDEN, FL 34787
$1,745,000307 Days on yellowkey MLS ID: O6328707
2 Days Off yellowkey (back on 5/1/2026)
REDUCED by $79,888 (4.4%) on 04/22/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4716 Built: 2014Monthly Fee: $201 Tax: $14,959 (2024)Community: West Lake Hancock EstatesSpa: NoSingle Family
Taxes:$14,959
Remarks: Under contract-accepting backup offers. Experience the Best of Florida Living! Enjoy Florida’s natural beauty from the comfort of your own home with breathtaking sunset views over a serene lake. Whether you're watching the full moon rise or catching glimpses of Disney’s nightly fireworks, this modern residence offers a front-row seat to nature’s magic. Designed for both relaxation and entertaining, this spacious home boasts soaring ceilings and elegant interiors that make every day feel regal. With 5 bedrooms and 4.5 bathrooms, there's room for families of all sizes—plus dedicated spaces for a private office, guest accommodations, a home theater, and a game room. The luxurious master suite features stunning lake views, a spa-like bath with a soaking tub, and an expansive walk-in closet that offers more than enough storage for your entire wardrobe. Located in the scenic community of Winter Garden, this home includes exclusive access to a private clubhouse with a resort-style pool and fitness center. Guests will love movie nights and gatherings in your inviting space. Conveniently close to theme parks, downtown Orlando, major highways, top-rated schools, and shopping centers, this home offers the perfect blend of comfort and convenience. Don’t miss your chance to own this exceptional home—schedule your private showing today!
Listing is courtesy of: FL SUNSHINE STATE REALTY (407-619-6745)
Listing Agent: Mae Wang (407-619-6745)
WINTER GARDEN, FL 34787
$619,00036 Days on yellowkey MLS ID: O6399369
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1827 Built: 2001Monthly Fee: $320 Tax: $4,811 (2025)Community: Woodbridge On GreenSingle Family
Taxes:$4,811
Remarks: Welcome to Woodbridge on the Green—one of Winter Garden’s best-kept secrets, ideally situated next to West Orange Country Club. This beautifully maintained waterfront home offers exceptional curb appeal and a spacious, single-story layout designed for comfortable living. Step inside to an inviting open floor plan filled with natural light and waterfront views. High ceilings and stylish luxury flooring enhance the home’s modern feel, creating a bright and airy atmosphere throughout. The well-appointed kitchen features custom countertops, rich wood cabinetry, and a full appliance package, with culinary nook overlooking the peaceful & gorgeous waterfront—perfect for both everyday living and entertainment. The generously sized primary suite provides a peaceful retreat, complete with closet, dual vanities, and a walk-in shower. Unwind on the screened-in lanai, where you can enjoy tranquil water views, mature oak trees, and beautiful Florida sunsets—your own private outdoor oasis. Living in Woodbridge on the Green means embracing a low-maintenance, resort-style lifestyle. The HOA takes care of all landscaping and exterior painting, and residents enjoy access to a private boat and RV storage area within the community. Recent upgrades add even more value and peace of mind, including a new AC system (2025), garage door opener (2026). Located within an “A”-rated school district, including Windermere High School—one of Florida’s top-ranked schools—this home is also just minutes from Winter Garden Village, major roadways, dining, shopping, Disney and the Magic Kingdom and all Central Florida area attractions. It is the responsibility of all prospective buyers and their agents to independently confirm the accuracy of all listing information, including measurements, specifications, and all other material details. No representations or warranties are made as to the completeness or accuracy of such information.
Listing is courtesy of: RAVENSCROFT REALTY GROUP (407-855-0005)
Listing Agent: Tom Ravenscroft, Jr. (407-222-7660)
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