Location: Winter Garden
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)
16294 HONEY HARVEST ST, WINTER GARDEN, FL 34787
$685,00021 Days on yellowkey MLS ID: O6403794
REDUCED by $25,000 (3.5%) on 05/15/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2812 Built: 2024Monthly Fee: $229 Tax: $9,329 (2025)Community: Harvest/OvationSingle Family
Taxes:$9,329
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: USE PREFERRED LENDER AND RECEIVE CLOSING COST ASSISTANCE! Welcome Home! Don't wait for your home to be built...step inside this gorgeous 2024-built bungalow-style home featuring a fully detached STUDIO apartment with its own entrance, perfect for guests, in-laws, or potential rental income. FULLY UPGRADED! This 5-bedroom, 4.5-bathroom home offers the perfect blend of space, style, and flexibility. Inside the main home, you’re welcomed by tall ceilings, an open layout, and a convenient downstairs bedroom and full bathroom. The modern kitchen is beautifully designed with a gas range, quartz countertops, shaker cabinets, and an open-concept flow overlooking the main living spaces. Upstairs, you’ll find two additional guest bedrooms, a shared full bathroom, and a conveniently located laundry room. The grand primary suite is a true retreat, featuring a spacious layout with soaring ceilings and a stunning en-suite bathroom complete with a walk-in shower, generous counter space, and an oversized walk-in closet. The studio apartment is privately accessed just outside of the garage and is fully equipped with its own full bathroom, kitchenette, and closet—making it ideal for guests or income-producing potential. Located in one of Horizon West’s most desirable communities, this home offers unbeatable convenience just minutes from Flamingo Crossings, Walt Disney World, and Hamlin Town Center.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Elliott Hunt (770-355-9149)
16004 OLLIVETT ST, WINTER GARDEN, FL 34787
$859,000325 Days on yellowkey MLS ID: S5130060
Bed: 7 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4704 Built: 2014Monthly Fee: $110 Tax: $9,493 (2024)Community: Verde Park Ph 1Single Family
Taxes:$9,493
Elementary School: Grassy Lake Elementary
High School: Lake Minneola High
Tax Year: 2024
Middle School: East Ridge Middle
Remarks: Welcome to this exceptional home with abundant natural light. Perfect for those looking for a home that is large or suitable for multi-generational living. The home features 7 bedrooms with two full master suites, on downstairs and one upstairs. Both have spa bathrooms with his and hers vanities, soaking tubs and separate shower, large oversized closets and spacious additional flex spaces. There are 5 additonal spacious secondary bedrooms that includes a guest bedroom on first floor with remaining bedrooms upstairs with walk in closets. With a 5 way bedroom split, this home offers true privacy for everyone. The family room is light and bright and open to the gourmet kitchen and nook area. In the gourmet kitchen there is a large center island, 42" cabinets, Kitchenaid stainless steel appliances with built in oven and microwave and cooktop, pot filler, touch faucet, granite counter tops and Samsung refrigerator. A large butler pantry is perfect for a morning coffee bar, wine bar or snack station. Off of the foyer is the dining room and additional living room that can be used as a home office, den, playroom or flex space. Upstairs you will find entertainment options with a large light and bright bonus room compete with wet bar and an additional TRUE media room for fun movie nights. Overlooking the kitchen/family room is the open lanai area that overlooks the sparkling salt water with fountain. The yard and patio allows for seamless indoor/outdoor living space and tv hookup. The 3 car tandem garage has custom built in metal storage cabinets and overhead garage racks for plenty of storage. Freshly painted exterior. Don't miss out on the opportunity to own this stunning home in the Verde Park Community. Not only does this exceptional home offer a luxurious lifestyle, but it's also conveniently located near the Florida Turnpike, 429, 408 ensuring an easy commute to downtown Orlando, the attractions and airport. Close to incredible shopping and dining options in Winter Garden and Clermont, as well as top public and private schools, hospitals, parks, lakes, and the West Orange Trail that is steps from the community entrance. This home is the perfect blend of convenience and luxury. And, it has a Winter Garden mailing address but is located in Lake County with Lake County taxes.
Listing is courtesy of: REMAX PREMIER PROPERTIES (407-343-4245)
Listing Agent: Paola Almonte (407-968-7511)
241 N DILLARD ST, WINTER GARDEN, FL 34787
$1,499,999214 Days on yellowkey MLS ID: O6353975
REDUCED by $100,001 (6.3%) on 04/13/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3507 Built: 1953 Tax: $2,959 (2024)Community: J L Dillard Sub 3Single Family
Taxes:$2,959
Elementary School: Dillard Street Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
636 S PARK AVE, WINTER GARDEN, FL 34787
$249,90034 Days on yellowkey MLS ID: O6400433
0 Days Off yellowkey (back on 5/19/2026)
REDUCED by $10,000 (3.8%) on 05/19/2026
Bed: 4 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 1272 Built: 1953 Tax: $3,751 (2025)Community: BurchshireSingle Family
Taxes:$3,751
Elementary School: None
High School: None
Middle School: None
Remarks: Location! Location! Investor Alert! This 4 bedroom 1 1/2 bath Winter Garden home is a block away from Veterans Memorial Park, and close to Downtown Historic Winter Garden. Home appears larger than records indicate, and has 4 full bedrooms and 1 1/2 baths. Almost 1/4 Acre Lot (.22). NEWER ROOF (2021), NEWER A/C, NEWER KITCHEN with Wood Cabinets, Granite, and SS Appliances. Tile floors in Great Room, and wood laminate floors in bedrooms. Large 544 Sq Ft 2 Car Garage with Work Shop Area. Large partially fenced lot. REDUCED FOR QUICK SALE. BUYER MAY OBTAIN FINANCING, BUT OFFERS SHOULD NOT BE CONTINGENT UPON FINANCING. INSPECTIONS BEST PRIOR TO PRESENTING CONTRACT, OR LIMIT INSPECTION PERIOD TO 2 CALENDAR DAYS.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: David Kravitz (407-656-7653)
345 WINTER ST, WINTER GARDEN, FL 34787
$285,00028 Days on yellowkey MLS ID: O6402105
2 Days Off yellowkey (back on 4/28/2026)
INCREASED by $5,100 (1.8%) on 04/26/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 700 Built: 1951 Tax: $211 (2025)Community: Shadow LawnSingle Family
Taxes:$211
Remarks: Under contract-accepting backup offers. Step into a storybook setting with this Enchanting, Turnkey Bungalow nestled in the heart of Winter Garden—a true must-see that captures both charm and modern comfort. From the welcoming front porch to the beautiful luxury vinyl plank flooring and picturesque backyard, every detail invites you to slow down and feel at home. Thoughtfully and completely remodeled, this darling residence offers 2 bedrooms, 1 bathroom, and a bright, airy layout designed for easy living and is staged to absolute perfection. Beyond the front door, discover a lifestyle that’s simply unmatched. Take a short stroll to Plant Street or hop onto the scenic West Orange Trail, where the beauty of Winter Garden unfolds all around you. Winter Garden, Florida feels like a place where charm and sunshine quietly linger year-round. Brick-lined streets wind through a historic downtown filled with beautifully restored storefronts, local boutiques, and inviting cafés that spill out onto the sidewalks. Towering oak trees draped in Spanish moss provide shade as the West Orange Trail weaves its way through town, alive with cyclists, joggers, and families enjoying the breeze. Just steps away, the shimmering waters of Lake Apopka create a peaceful backdrop, where golden sunsets stretch across the horizon and birds glide effortlessly over the marshlands. The weekly farmers market brings the community together with fresh blooms, local flavors, and the kind of small-town warmth that’s hard to find elsewhere. Blending old Florida charm with thoughtful growth, Winter Garden offers a lifestyle that feels both relaxed and vibrant—where every corner seems to invite you to slow down, take it in, and stay awhile. Back at home, enjoy peace of mind with extensive updates including a new roof, AC, flooring, kitchen, bathroom, plumbing, and electrical—truly move-in ready. With NO HOA and NO CDD, this property is ideal for a first-time buyer, downsizer, or anyone seeking a slice of charm close to it all. Step outside into an absolutely stunning outdoor retreat, where a beautifully landscaped gravel backyard sets the stage for relaxation and connection. Your private patio invites you to grill, unwind, and gather with loved ones—sharing stories, laughter, and unforgettable memories under the open sky. Opportunities like this don’t come around often—schedule your private showing today before it’s gone.
Listing is courtesy of: THE NAVY HOUSE (321-438-1318)
Listing Agent: Katie Nguyen (321-438-1318)
16749 HARPER COVE DR, WINTER GARDEN, FL 34787
$499,99933 Days on yellowkey MLS ID: O6400511
REDUCED by $15,001 (2.9%) on 05/19/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2014 Built: 2019Monthly Fee: $257 Tax: $7,287 (2024)Community: Waterleigh Ph 2C-1Single Family
Taxes:$7,287
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2.5-bath two-story home featuring a rear-load 2-car garage, ideally located in one of the area’s most desirable master-planned communities. Designed for modern living, the open-concept floor plan showcases durable tile flooring throughout the main level for easy maintenance. The kitchen is a true centerpiece, complete with granite countertops, white cabinetry, stainless steel appliances, and a large center island—perfect for entertaining or everyday living. The spacious first-floor primary suite is filled with natural light and features a walk-in closet, dual-sink granite vanity, and an oversized walk-in shower. Upstairs, you’ll find brand new carpet, a versatile loft space, two additional bedrooms, and a full bathroom with a dual-sink vanity and tub/shower combination—ideal for guests or family. Waterleigh continues to stand out as one of the premier communities in Horizons West, offering resort-style amenity centers, multiple pools, splash pads, indoor and outdoor fitness areas, scenic lakes and ponds, walking and nature trails, beach volleyball courts, playgrounds, and sports fields. A Publix is conveniently located at the community entrance, and lawn maintenance is included for added ease. This is Florida living at its best—whether you're an investor or end user. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Tara Garkowski (407-405-8829)
3306 HANGING TIDE ST, WINTER GARDEN, FL 34787
$585,000260 Days on yellowkey MLS ID: G5101402
4 Days Off yellowkey (back on 3/23/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2894 Built: 2022Monthly Fee: $138 Tax: $9,355 (2024)Community: Lakeview Preserve Ph 2Single Family
Taxes:$9,355
Elementary School: Lost Lake Elem
High School: East Ridge High
Middle School: Windy Hill Middle
Remarks: Short Sale. Welcome to this amazing two-story home, 2800 sqft, 4 beds, 2.5 bath with a premium lot overlooking the retention pond. No back neighbors, tons of upgrades and enough place to build a pool. Lakeview Preserve is a waterfront gated community with access to Johns Lake. The community offers many amenities such as fitness center, pool, pavilion, kayak launch, splash pad, playground and picnic areas. The floorplan is very desirable for families with the master on the first floor and the remaining bedrooms on the second floor including loft area. The home features an open floor plan with the Kitchen area open to the Family Room and Dining Room and luxury flooring on the first floor. The master suite includes a garden tub, oversized shower, dual sinks with a quartz counter top, linen and walk-in closet. An upgraded gourmet kitchen features a walk-in pantry, large center island, built-in stainless-steel appliances, 42” cabinetry, and quartz countertops. Tons of natural light brightens the space. The large retractable screen and sliding door is a unique future, giving you flexibility of having the space open or closed to the outdoors. The location is in close proximity to the major theme parks throughout Central Florida!
Listing is courtesy of: PREFERRED RE BROKERS III (407-440-4900)
Listing Agent: Cristina Mcguire (321-217-6199)
11265 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$870,33116 Days on yellowkey MLS ID: O6405351
2 Days Off yellowkey (back on 5/19/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3225 Built: 2025Monthly Fee: $200 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Taxes:$1,989
Remarks: Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 5 bedrooms and 4.5 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 and butler’s pantry. 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 walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Located off the family room is 5th bedroom and a full bathroom. As we head up to the second floor, we are greeted with a game room and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey 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.*
Listing is courtesy of: DR HORTON REALTY OF CENTRAL FLORIDA LLC (407-250-7299)
Listing Agent: Stephen Cline (407-250-7299)
16809 HOBE SOUND CT, WINTER GARDEN, FL 34787
$559,990134 Days on yellowkey MLS ID: O6372242
REDUCED by $10,000 (1.8%) on 05/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2216 Built: 2025Monthly Fee: $248 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Remarks: Under Construction. Waterleigh presents the Bellake. This amazing all concrete block construction single-family home features 3 bedrooms and 2.5 bathrooms optimizing living space with an open concept feel. The kitchen overlooks the dining and great room, while having view to the covered lanai outside. Ample windows and a set of sliding glass doors allow lighting into the living area. The well-appointed kitchen features an island with bar seating, plentiful cabinet and counter space and stainless steel appliances, making entertaining a breeze. The first floor also features a flex room that provides an area for work or play and half bathroom. As we head up to the second floor, we are greeted with Bedroom one which includes a spacious walk-in closet as well as ensuite bathroom with double vanity. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. Your laundry room is located on the second floor as well. This home features a two car garage located at the rear of the home complete with drop zone as you enter the home. Like all homes in Waterleigh, the Bellake 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.*
11217 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$849,99038 Days on yellowkey MLS ID: O6399115
REDUCED by $16,821 (1.9%) on 04/22/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3327 Built: 2025Monthly Fee: $199 Tax: $1,989 (2025)Community: WaterleighSpa: NoSingle Family
Remarks: 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 a 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. *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.*
14784 FIELD DAISY DR, WINTER GARDEN, FL 34787
$690,0007 Days on yellowkey MLS ID: O6408277
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2841 Built: 2026Monthly Fee: $229Community: Harvest At OvationSingle Family
Taxes:$0
Remarks: Under Construction. What's Special: Covered Extended Lanai | Secondary Bedroom with an Attached Bath | North Facing Lot | Game Room. New Construction - August Completion! Built by America's Most Trusted Home Builder. Welcome to the Baldwin at 14784 Field Daisy Drive in Harvest at Ovation! This new bungalow-style home welcomes you with a charming entry that flows past a main level guest bedroom with a private bath and into a spacious, open great room. The kitchen overlooks the main living area and connects to a casual dining space, creating an easy setting for everyday living and gathering. At the back of the home, an extended lanai offers a sunny outdoor retreat perfect for relaxing under the Florida sky. Upstairs, the primary suite provides a private escape with a dual-sink vanity, walk-in shower, and a relaxing atmosphere, while two additional bedrooms, a full bathroom, and a conveniently located laundry room share the level and overlook the open living space below. A game room with a full bath above the two-car garage adds flexible space for entertaining, hobbies, or overnight guests. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: wet bar in game room and custom 42" cabinets throughout. Photos are for representative purposes only. MLS#O6408277
Listing is courtesy of: TAYLOR MORRISON REALTY OF FLORIDA INC (407-756-5025)
Listing Agent: Michelle Campbell (407-756-5025)
1101 EAGLES PASS WAY, WINTER GARDEN, FL 34787
$1,725,0004 Days on yellowkey MLS ID: O6408835
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4104 Built: 2023Monthly Fee: $203 Tax: $19,016 (2024)Community: Oakland ParkSingle Family
Taxes:$19,016
Elementary School: Tildenville Elem
Remarks: One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two miles from the historic downtown shops and restaurants, this home beautifully blends modern luxury with small-town charm. Step inside to discover designer finishes and thoughtful craftsmanship throughout. The gourmet kitchen features top-end Monogram appliances, including a 36” dual-fuel range, warming oven, and a 48” side-by-side refrigerator and freezer. Upgraded quartz countertops, a brick backsplash and hearth with built-in electric fireplace, and engineered hardwood floors elevate the open-concept main living areas. Additional luxury touches include Brizo faucets, custom plantation shutters, and floating shelving systems in every bedroom closet. The owner’s suite offers a spa-inspired retreat with a 6-foot soaking tub, while the upgraded pantry with butcher block countertop, dimmer switches, and ceiling fans throughout enhance everyday comfort. An in-law suite featuring a full bath, family room, and a private staircase above the garage provides the perfect space for guests, extended family, or a private home office. Enjoy peaceful mornings and sunset evenings from the screened front and side porches, adding to the home’s charm and livability. Located in Oakland Park, residents enjoy resort-style amenities including two community pools, multiple parks and playgrounds, scenic walking and biking trails, a clubhouse, and direct access to the West Orange Trail. With tree-lined streets, lake views, and friendly front-porch living, this award-winning community captures the very best of Winter Garden living.
Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)
Listing Agent: Kevin Sullivan (321-663-3457)
1692 HIGHBANKS CIR, WINTER GARDEN, FL 34787
$760,0004 Days on yellowkey MLS ID: O6408620
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2848 Built: 2017Monthly Fee: $142 Tax: $5,936 (2025)Community: Roper ReserveSingle Family
Taxes:$5,936
Remarks: Located in the highly desirable Roper Reserve gated community, this beautifully maintained 4-bedroom, 3.5-bath home offers the perfect combination of comfort, space, and privacy. Situated on a premium lot with peaceful pond and conservation views, enjoy no rear neighbors and a tranquil setting just minutes from everything Winter Garden has to offer. The home features an open-concept layout with a newly upgraded kitchen showcasing quartz countertops, new cabinetry, stainless steel appliances, a large center island, and an oversized walk-in pantry. Upstairs, the oversized 4th bedroom/loft offers endless potential as a guest suite, game room, office, media room, or additional living space. Additional highlights include a formal dining area, spacious living areas, and a 3-car split garage. Conveniently located near top-rated schools, shopping, hospitals, major highways, Downtown Winter Garden, and just a short drive to Walt Disney World Resort. Community amenities include a fitness pavilion, playground, and direct access to the West Orange Trail.
Listing is courtesy of: VESTI LLC (407-749-5489)
Listing Agent: Juan Vanegas Montoya (407-749-5489)
17124 BEACHGRASS ALY, WINTER GARDEN, FL 34787
$559,9904 Days on yellowkey MLS ID: O6408024
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1983 Built: 2026Monthly Fee: $112 Tax: $6,874 (2025)Community: Lake Star At OvationSpa: NoSingle Family
Taxes:$6,874
Remarks: Under Construction. Welcome to 17124 Beachgrass Alley, in Winter Garden, Florida: a new construction home built by M/I Homes, offering 1,983 square feet of thoughtfully designed living space. This home features a well-crafted floorplan combining quality design with everyday functionality. This home features 3 bedrooms, 2.5 bathrooms, an open-concept living space perfect for daily living and entertaining, a lanai, and a 2-car rear-load garage This home showcases an open-concept living space that creates a seamless flow between the family room, kitchen, and dining area, making it ideal for both relaxed evenings and hosting guests. The floorplan is designed with intention, ensuring each room serves a clear purpose while maintaining a cohesive feel throughout. Upstairs, the owner's bedroom offers a private retreat, complete with an en-suite bathroom and walk-in closet for added convenience. The overall layout reflects a commitment to quality design, with clean lines and functional spaces that make everyday living comfortable. Situated in a desirable Winter Garden neighborhood, this home benefits from proximity to parks and outdoor recreation areas, providing easy access to green spaces for families and individuals alike. The surrounding neighborhood offers a welcoming atmosphere with well-maintained streets and a sense of connection to the outdoors.
Listing Agent: Stacie Brown Kelly (407-221-4954)
17106 BEACHGRASS ALY, WINTER GARDEN, FL 34787
$799,9904 Days on yellowkey MLS ID: O6407735
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1983 Built: 2025Monthly Fee: $172 Tax: $10,166 (2025)Community: Lake Star At OvationSpa: NoSingle Family
Taxes:$10,166
Remarks: **Model Home for Sale** Step inside the Jensen model home and experience a thoughtfully designed space that blends modern style with everyday livability. This two-story home welcomes you with a bright, open-concept first floor where the family room, dining area, and kitchen flow together effortlessly—perfect for hosting friends or enjoying a relaxed night in. The kitchen is the heart of the home, showcasing crisp white cabinetry, sleek hardware, built-in stainless steel appliances, and an oversized island with seating that’s ideal for casual meals and entertaining. Designer pendant lighting and light wood-look flooring add warmth and sophistication throughout the main living space. Upstairs, the private owner’s suite creates a peaceful retreat, complete with tray ceiling detail, a spacious walk-in closet, and a well-appointed en-suite bath. Two additional secondary bedrooms, a full hall bath, and an conveniently located laundry room make the second floor both functional and comfortable. At the back of the home, the covered lanai extends your living space outdoors and creates the ultimate entertaining zone. Wood-plank ceilings, a ceiling fan, built-in grill area, and a spa-style hot tub set the stage for relaxing evenings and weekend gatherings in true Florida style. With its charming exterior, rear-load garage, and designer finishes throughout, the Jensen model home perfectly reflects the lifestyle waiting for you at Lake Star at Ovation.
706 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,287,00053 Days on yellowkey MLS ID: O6394059
REDUCED by $30,000 (2.3%) on 05/09/2026
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4019 Built: 2018Monthly Fee: $298 Tax: $17,895 (2025)Community: Canopy Oaks Ph 1Single Family
Taxes:$17,895
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: A rare opportunity in a desired luxury neighborhood. A home designed for the way you live today, where walls of glass open completely, blending indoor and outdoor spaces into one seamless experience. In the gated community of Canopy Oaks, this A.R. Bailey Homes LLC Delray model offers elevated design, flexibility and everyday convenience. Well-maintained and only eight years young, this residence is set within an intimate enclave of just 49 homesites, offering a rare sense of privacy while remaining ideally positioned on Roper Road between Winter Garden’s historic downtown district and the Winter Garden Village shopping complex. From moment you arrive, the home makes a lasting impression with high-end driveway pavers, a durable concrete tile roof, woodgrain garage doors, stone facade accents and grand 8-foot solid wood arched double entry doors. Inside, the layout unfolds with intention, balancing elegant design and functional living. At the center of the home, the kitchen is designed to bring people together, featuring a natural gas cooktop with exterior venting, a built-in oven, upgraded appliances, a pot filler, 42-inch cabinetry with crown molding, a tile backsplash, under-cabinet lighting, a walk-in pantry and a large island that opens to the great room with coffered ceilings. Just beyond, a wine cellar with an iron gate adds a distinctive focal point for entertaining. The first-floor primary suite offers a peaceful retreat with a soaking tub, an oversized walk-in shower with dual heads and a bench, dual granite vanities and a custom closet system. A secondary first-floor, en-suite bedroom or office provides flexibility, while upstairs features a second primary suite, two additional en-suite bedrooms, a loft, a guest half bath and a covered rear balcony for added privacy and comfort. The standout is the home’s seamless indoor-outdoor connection. A full corner-opening glass wall, along with three-panel stackable sliding doors, extends the dining and great rooms to a covered lanai with a motorized retractable screen, creating a natural flow for entertaining or everyday living. The spacious backyard, framed by a concrete stucco privacy wall, offers a blank canvas for a future pool or custom outdoor retreat. Thoughtful upgrades continue throughout, including motorized custom light filtering roller shades in the dining and great rooms, dual tankless water heaters, two air-conditioning units with zoned climate control, mudroom, a reading nook and elegant iron stair railings. Residents of Canopy Oaks also enjoy a nature trail and a children’s play park. With proximity to downtown Winter Garden, Winter Garden Village, area hospitals, shopping, dining and major roadways including Florida Turnpike, state roads 429 and 408, and Interstate 4, this home presents a compelling opportunity to experience a lifestyle where design, comfort and location come together effortlessly.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Lisa Rutkowski (407-793-2416)
16277 HONEY HARVEST ST, WINTER GARDEN, FL 34787
$670,00032 Days on yellowkey MLS ID: O6400235
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2930 Built: 2024Monthly Fee: $229 Tax: $9,784 (2025)Community: Harvest/OvationSingle Family
Taxes:$9,784
Remarks: One or more photo(s) has been virtually staged. This 2024-built Baldwin in Harvest at Ovation offers nearly 2,900 total square feet with 5 bedrooms and 4.5 bathrooms, *set on a premium CONSERVATION LOT with no rear neighbors.* The main home features an open-concept layout with a first-floor bedroom and en suite full bath, spacious living and dining areas, and a gourmet kitchen with quartz countertops, upgraded cabinetry, and a walk-in pantry. Above the garage, a fully detached private suite adds approximately 530 square feet, complete with its own entrance, living area, kitchenette, bedroom, and full bath - ideal for guests, multigenerational living, or a private workspace. Located minutes from Walt Disney World, Hamlin Town Center, and Flamingo Crossings in one of Horizon West’s most desirable communities.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
17100 BEACHGRASS, WINTER GARDEN, FL 34787
$834,9907 Days on yellowkey MLS ID: O6407707
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2781 Built: 2025Monthly Fee: $172 Tax: $10,646 (2025)Community: Lake Star At OvationSpa: NoSingle Family
Taxes:$10,646
Remarks: Experience elevated everyday living in the Wekiva model home, a beautifully designed two-story floorplan that blends spacious living areas with designer finishes and thoughtful details throughout. From the inviting front porch to the bright, open living spaces inside, this home is crafted to impress at every turn. The main level features a wide-open layout that connects the family room, dining space, and kitchen, creating an ideal setting for both entertaining and everyday life. The kitchen shines with crisp white cabinetry, quartz-style countertops, built-in stainless steel appliances, and an oversized island with seating—all highlighted by statement pendant lighting and rich, warm flooring. A walk-in pantry and adjacent powder bath add convenience, while a private guest suite on the first floor offers flexibility for visitors or a home office. Upstairs, the owner’s suite feels like a private retreat, complete with tray ceiling detail, dual-sink vanity, a large walk-in shower, and a spa-inspired soaking tub. Three additional bedrooms, multiple full bathrooms, a bright loft space, and an upstairs laundry room create a functional layout designed to support busy, modern living. Step outside to the covered lanai to find a peaceful outdoor extension of the home—perfect for morning coffee or evening get-togethers. With its charming exterior, rear-load garage, and professionally designed interiors, the Wekiva model offers a true sense of luxury and comfort.
16385 ADMIRALS COVE LN, WINTER GARDEN, FL 34787
$469,90058 Days on yellowkey MLS ID: O6393056
0 Days Off yellowkey (back on 5/18/2026)
REDUCED by $100 (0.0%) on 04/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1705 Built: 2020Monthly Fee: $257 Tax: $4,805 (2025)Community: WaterleighSingle Family
Taxes:$4,805
Remarks: Under contract-accepting backup offers. Unique financing opportunities make this Waterleigh home a standout. Buyers can take advantage of a 2-1 buy-down paid by the seller’s preferred lender for added affordability and potential monthly savings in today’s market. Plus, the sellers are now offering $5,000 in concessions! This beautifully maintained 3-bedroom, 2-bath home features a bright, open-concept layout designed for both everyday living and easy entertaining. The spacious kitchen is the heart of the home, complete with stainless steel appliances, a walk-in pantry, and a large center island. The private owner’s suite offers a relaxing retreat with a generous walk-in closet and en-suite bath. Located in highly sought-after Waterleigh in Winter Garden, this home offers the lifestyle buyers are looking for, with golf cart-friendly streets, resort-style amenities, breathtaking Disney fireworks views, and the added convenience of a pool and playground directly across the street. Two schools are also located within the community, making this location as practical as it is desirable. Schedule your private showing today!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Shaheda Gordon-Jefferson (646-456-7410)
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