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$1,500,000
4 Beds ⋅ 4 Baths ⋅ Hickory Hammock Ph 1d SubDv. ⋅ 34787 Zip Code
Experience true lakefront living in the highly sought-after Hickory Hammock community in Winter Garden on the shores of Johns Lake. This stunning 4-bedroom, 3.5-bath home, showcases breathtaking sunset views and a seamless blend of luxury and comfort. Inside, rich wood flooring flows throughout the main living areas and most bedrooms, complemented by custom finishes, accent walls, and an open-concept layout designed for both everyday living and entertaining. The designer kitchen features an oversized island, upgraded cabinetry, stainless steel appliances, and stylish lighting, all overlooking a spacious living area with custom ceiling details and expansive sliding glass doors framing the lake. The primary suite offers a private retreat with a custom feature wall and a spa-inspired bath with dual vanities and a large walk-in shower. Additional highlights include a built-in bar/wine area, spacious laundry room, and a dedicated fitness room with sauna. Step outside to a true resort-style setting featuring an infinity-edge pool and spa overlooking the water, an expansive screened lanai, and a fully equipped outdoor living area with fireplace, TV, spacious seating area, refrigerator, stainless steel grill, and Big Green Egg. Enjoy direct lake access from your private dock complete with boat lift and automatic enclosure, perfect for boating, fishing, and year-round waterfront living. Located in one of Winter Garden’s premier communities with top-rated schools, clubhouse, fitness center, tennis courts, and convenient access to shopping and dining, this exceptional property offers the ultimate Florida lakefront lifestyle.

Winter Garden
$750,000
5 Beds ⋅ 3 Baths ⋅ Johns Lake Pointe SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to 940 Marsh Reed Drive, a beautifully upgraded 5 bedroom, 3 bathroom, SOLAR HEATED POOL HOME offering just under 3,500 square feet of well-designed living space in the highly sought-after Johns Lake Pointe community! Additional OFFICE and LOFT / BONUS ROOM. Solar panels are paid off! From the moment you arrive, the home makes a strong impression with its tile roof, enhanced landscaping, and well manicured appearance, setting the tone for what’s inside. The interior opens to a bright, expansive layout with high ceilings, neutral finishes, and multiple living and dining areas designed for both everyday comfort and entertaining. The heart of the home is the open-concept kitchen, featuring abundant cabinetry, walk-in pantry, granite countertops, stainless steel appliances, extended butler's pantry style prep area, and a large center island that flows seamlessly into the main living area. Natural light fills the space, creating an inviting atmosphere that connects effortlessly to the indoor and outdoor living areas. The first floor dedicated office provides the ideal work-from-home setup or can easily function as a flex space to suit your needs. Upstairs, a spacious loft/bonus area offers additional versatility—perfect for a media room, playroom, or secondary living space. The primary suite is generously sized and features tray ceilings, large windows, and a relaxing, private feel. The en-suite bathroom includes dual vanities, a walk-in shower, walk-in closet, and ample storage, creating a comfortable retreat at the end of the day. Step outside to your private backyard oasis, where the SCREENED-IN POOL and covered lanai deliver the ultimate Florida lifestyle. The pool is equipped with SOLAR HEATING for year-round enjoyment and a NEW POOL PUMP for efficiency. A standout feature is the $7,000 integrated smart exterior lighting system, including the pool enclosure, creating a stunning nighttime ambiance perfect for entertaining. Additional upgrades include a new gutter drainage system and overhead garage storage racks, offering both convenience and functionality. Located in Johns Lake Pointe, residents enjoy access to resort-style amenities including a community pool, fitness center, playground, and sports courts, all while being just minutes from major highways, shopping, dining, Winter Garden's Historic Plant Street, and everything Central Florida has to offer. Only a short drive to Disney! Close to HIGH-RATED SCHOOLS. This is a rare opportunity to own a move-in ready home that combines space, upgrades, and lifestyle in one exceptional package. Call now for your private showing!

940 Marsh Reed Drive, Winter Garden
$646,090
5 Beds ⋅ 4 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Berkley model features 2,102 square feet of well-designed living space across two stories, with an above-garage Apt 576 sqft.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. The apartment is above the garage with a private entrance. This neighborhood features a variety of townhomes and single-family homes on multiple-sized homesites, with spacious floor plans designed to support a wide range of lifestyles, from growing families to move-up buyers seeking more room to live and entertain. Located just minutes from Hamlin Town Center, Winter Garden Village, and historic Downtown Winter Garden, Hamlin Meadows places shopping, dining, and entertainment close to home. Residents will also enjoy access to nearby parks, trails, and outdoor recreation, along with proximity to highly regarded Orange County schools, including Hamlin Elementary, Hamlin Middle, and Horizon High School.

17031 Haggerty Hollow Drive, Winter Garden
$740,205
6 Beds ⋅ 5 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage

17428 Sunset Prairie Drive, Winter Garden
$831,500
4 Beds ⋅ 3 Baths ⋅ Sunset Lakes SubDv. ⋅ 34787 Zip Code
Beautifully updated single-story home featuring 4 bedrooms and 3 bathrooms, situated on an expansive lot of over half an acre in the desirable Sunset Lakes community. This residence offers a spacious layout ideal for comfortable living and has been fully remodeled throughout. The home features a great gourmet kitchen with a large island and sleek Dekton countertops, perfect for both everyday living and entertaining. Step outside to a stunning backyard retreat with a private pool and screened enclosure, ideal for year-round enjoyment. Ideally located just minutes from Highway 429, Winter Garden Village, and world-renowned attractions like Walt Disney World, this property also benefits from access to highly rated A-grade schools, making it an exceptional opportunity in one of Winter Garden’s most sought-after areas.

13393 Sunset Lakes Circle, Winter Garden
$760,000
4 Beds ⋅ 3 Baths ⋅ Overlook 2/Hamlin Ph 3 SubDv. ⋅ 34787 Zip Code
Fantastic Jamestown model with 4 bedrooms, 2.5 bath with screened lanai and backing to common area. Home upgrades include Solar Panels, under eaves lighting, water filtration system, new flooring and updated secondary bath. The home is located close to the Hamlin Town Center and is located in a sought after planned community with pool, clubhouse, parks, fitness center and dog park. Easy access to SR429 and the Florida Turnpike.

5637 Tiger Way, Winter Garden
$780,000
7 Beds ⋅ 4 Baths ⋅ Belle Meade Ph 02 H SubDv. ⋅ 34787 Zip Code
Priced below market value and packed with exceptional upgrades, this stunning home in the highly sought-after Belle Meade community is an incredible opportunity. Offering over 4,400 square feet of living space, this spacious 7-bedroom, 4-bathroom residence features oversized bedrooms and soaring ceilings on both levels, creating an open and airy feel throughout. Designed for both comfort and entertaining, the upstairs bonus room includes its own bar, while the air-conditioned sunroom provides the perfect space to relax and enjoy year-round. Step outside to a fully fenced backyard set on more than a quarter acre, complete with two mature mango trees for a true Florida touch. This home also offers outstanding peace of mind with major recent improvements, including a new roof in 2023, new windows, a whole-house water filtration system, and fully paid-off solar panels—an incredible value and long-term savings for the next owner. Families will love the top-rated school zoning for Whispering Oak Elementary, Sunridge Middle, and West Orange High, along with the added convenience of being directly across from Foundation Academy, one of Winter Garden’s premier private schools. For recreation and leisure, West Orange Country Club is just one mile away, offering golf, tennis, and more. Ideally located near Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and New Independence, this home also provides easy access to Disney, Universal, Orlando International Airport, and major highways including the 429, Turnpike, and 408. This is the perfect blend of size, upgrades, location, and value—schedule your private showing today.

15183 Serenade Drive, Winter Garden
$1,250,000
4 Beds ⋅ 4 Baths ⋅ Overlook At Hamlin SubDv. ⋅ 34787 Zip Code
Welcome to Horizon West living at its finest in the highly sought-after Overlook at Hamlin community, home of top-rated schools. This exceptional pool home is perfectly positioned on a premium oversized lot offering over 4k SF with lake views in the front and fireworks views in the back. The thoughtfully designed living space has a northwest-facing orientation, allowing you to enjoy breathtaking sunrise views from your backyard oasis and stunning sunset views from the front. This luxurious and meticulously maintained upgraded home features 4 to 6 bedrooms, 3.5 bathrooms, and a highly desirable first-floor primary suite designed for comfort and privacy. The open-concept floor plan is enhanced by a spacious loft and multiple flex spaces, including dedicated offices or additional bedrooms on both levels, each with elegant French doors. The expansive living area is anchored by a custom 20-foot entertainment wall complete with built-ins, a fireplace, and integrated sound, creating the perfect setting for both relaxation and entertaining. The chef’s kitchen is a true showpiece, upgraded with brand-new commercial-style Café luxury appliances (2026), gas cooktop, custom cabinetry with soft-close features, designer backsplash, upgraded lighting, and an oversized custom pantry with a butler’s area. Multiple dining spaces, including a formal dining room and eat-in kitchen, offer versatility for gatherings both large and intimate. Additional major upgrades provide peace of mind and modern efficiency; two brand-new Carrier AC systems (2026) with a 10-year warranty, whole-house water purification and softener system, and new LED lighting in the pool. The home also includes 2 tankless gas water heaters and features high-end finishes throughout, including commercial-grade luxury vinyl flooring, premium carpeting, fresh interior paint, designer lighting, and smart home enhancements such as remote-controlled window treatments and extensive wall-mounted TV connections. Step outside to your private resort-style retreat, featuring a custom 600-square-foot saltwater pool with marble decking, sun shelf, waterfall features, and panoramic screened enclosure designed to maximize views of Disney fireworks. A separate spa, added in 2024, creates the ultimate relaxation experience. The outdoor living space is complete with a fully equipped summer kitchen, built-in bar, tongue-and-groove ceilings, and professionally designed landscaping with privacy hedges and palm trees. With no direct rear neighbors and a dry retention pond behind, this home offers exceptional privacy and serene surroundings. Additional exterior highlights include an extended driveway, oversized two-car garage with space for a golf cart, full fencing with multiple access points, exterior lighting, gutters, and security features, including cameras and motion lighting. Located just a half-mile from Hamlin Town Center, this home is accessible via walking trails, golf cart, or a 1-minute drive to shopping, dining, and entertainment. Residents of the Overlook community enjoy resort-style amenities, including a clubhouse, fitness center, community pool with splash area, walking trails, dog park, playgrounds, fishing pier, and private boat ramp access to Lake Hancock. This is a rare opportunity to own a move-in-ready luxury home in one of Winter Garden’s most desirable locations, where you can experience elevated Florida living at its best. Set up a showing today before it's gone.

5401 Bowman Drive, Winter Garden
$797,398
4 Beds ⋅ 4 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering FOUR bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully positioned for privacy. An additional bedroom and a flexible bonus room on the second floor provide ample space for family members or guests.

15111 Tea Tree Drive, Winter Garden
$551,990
3 Beds ⋅ 2 Baths ⋅ Avalon Woods SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to the Amelia, a charming single-story bungalow, located in the highly sought-after new community of Avalon Woods in Hamlin, Winter Garden. This thoughtfully designed home features a welcoming front porch, a covered breezeway, and a private courtyard, perfect for both relaxing and entertaining. Inside, additional windows have been added throughout, filling the home with abundant natural light and creating a bright, open feel. With its functional single-level layout, the Amelia offers effortless living while combining modern comfort with timeless bungalow charm. Located just minutes from the popular shopping and dining destinations of Winter Garden Village and historic downtown Winter Garden, Avalon Woods places residents close to everything they need. Nearby parks, trails, and recreational areas offer plenty of opportunities for outdoor enjoyment, while the area’s top-rated schools make it an excellent choice for families. With easy access to major roadways like SR-429 and the Florida Turnpike, commuting to Downtown Orlando, the theme parks, or neighboring communities is convenient and efficient. Avalon Woods delivers the perfect balance of comfort, connection, and community in one of Central Florida’s most desirable locations.

6327 Wild Persimmon Way, Winter Garden
$584,000
4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion end of 2026. Single family Bungalow. The Montpelier home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a primary suite is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet. There's still time to personalize this home with your preferred design upgrades.

13014 Sunset Garden Lane, Winter Garden
$644,000
4 Beds ⋅ 4 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion end of 2026 Bungalow featuring a private in-law suite above a detached 2-car garage. A charming covered entry welcomes you into an open and expansive floor plan with seamless flow between the great room, kitchen, and dining area — ideal for both everyday living and entertaining. Enjoy outdoor Florida living with a covered lanai and a spacious private courtyard offering direct access to the detached garage and guest suite. The primary bedroom retreat includes a generous walk-in closet and a well-appointed bath with dual vanities, separate shower, and private water closet. Located in the highly sought-after Horizon West community, this thoughtfully designed home combines elegance, functionality, and flexible living space. Schedule your showing today.

13008 Sunset Garden Lane, Winter Garden
$560,000
3 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code
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!

15524 Aviation Alley, Winter Garden
$640,000
4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 4b SubDv. ⋅ 34787 Zip Code
Elevated Florida Living: Designer 4BR Home in Sought-After Summerlake! Welcome to a refined blend of elegance and modern comfort in the fabulous Summerlake community of Winter Garden. This exceptional two-story residence offers 4 bedrooms and 3 full bathrooms, thoughtfully curated with upscale finishes and timeless design. From the moment you enter, you’re greeted by an abundance of natural light and a seamless open-concept layout that exudes both sophistication and warmth. The expansive living and dining areas flow effortlessly into a beautifully appointed chef’s kitchen, featuring premium countertops, custom cabinetry, and an oversized island designed for both everyday living and elevated entertaining. A main-level guest suite with a full bath provides privacy and flexibility, ideal for visitors or a dedicated executive office. Upstairs, retreat to the luxurious primary suite—your private sanctuary—complete with a spa-inspired en-suite bath and a spacious walk-in closet. Additional bedrooms and a versatile loft adds endless possibilities for relaxation, work, or play. Step outside to your covered lanai and enjoy serene outdoor living, perfect for morning coffee or evening gatherings under the Florida sky. As a resident of Summerlake, you’ll enjoy access to resort-style amenities including a sparkling community pool, state-of-the-art fitness center, scenic walking trails, and beautifully maintained green spaces—all just minutes from top-rated schools, upscale shopping, dining, and convenient highway access. This is more than a home—it’s a lifestyle defined by comfort, convenience, and elevated living.

8150 Gray Kingbird Drive, Winter Garden
$381,000
3 Beds ⋅ 2 Baths ⋅ Westchester Place SubDv. ⋅ 34787 Zip Code
Situated just two blocks outside the Golf Cart District and directly across from Veterans Memorial Park, this property offers a lifestyle that blends convenience, privacy, and outdoor living. BRAND NEW ROOF JUST INSTALLED! (April 2026, 10-yr warranty) Set on a rare double lot, the home welcomes you with mature landscaping, an orchid tree in the front yard, stylish Bermuda hurricane shutters, and a covered front porch that provides a charming place to relax and enjoy the neighborhood. Inside, the spacious layout features durable porcelain wood-grain tile flooring installed in 2017, a bright living area, and a generous kitchen designed for everyday functionality and gathering. Major updates provide peace of mind, including all new double-pane windows installed in 2021, a water heater replaced in 2020, HVAC from 2019 (installed 2021) under warranty with American Air & Heat, and upgraded WiFi. Outside is where the property truly shines. The fully fenced backyard offers exceptional privacy with mature landscaping, fruit trees including kumquat, green apple, mango, and pineapple, along with bananas, plantains, pecan, and raised herb beds featuring aloe, basil, spearmint, and Italian oregano. Entertain or unwind on the recently resealed paver patio or under the pergola, while the powered shed with custom shelving and ramp provides flexible space for hobbies or storage. Additional features include a large private driveway, gutters, double weather-stripped front doors, and a chicken coop. With extensive updates, functional living space, and a backyard designed for gardening, relaxing, and entertaining, this home offers a unique opportunity to enjoy both comfort and outdoor lifestyle.

604 Foster Avenue, Winter Garden
$975,000
3 Beds ⋅ 3 Baths ⋅ Country Lakes SubDv. ⋅ 34787 Zip Code
Virtually Staged. Rarely does a property offer over an acre of land in the heart of Winter Garden. Tucked away in an intimate lake-access community, this beautifully refreshed pool home combines privacy, mature trees, and an unbeatable location just minutes from everything Central Florida has to offer. Set on a beautifully landscaped 1.1-acre lot with no rear neighbors, this stunning residence offers a rare opportunity to enjoy space, serenity, and flexibility in one of Winter Garden's most desirable locations. Designed for both everyday living and effortless entertaining, the home features fresh interior paint, new luxury vinyl plank flooring throughout the main living areas and bedrooms, a newer roof, new water heater, oven, range, custom woodwork, and a beautiful wood-burning brick fireplace that anchors the living space. The expansive covered lanai, refinished screened-in pool with a new pump, and spa create a true indoor-outdoor lifestyle, with multiple access points from the home and a kitchen pass-through window that opens directly to the entertaining area. Privately situated on the opposite side of the main 3 bedrooms, the light-filled bonus room features two closets, French doors, its own exterior entrance, and tranquil views of the mature landscaping. Paired with the adjacent full bath, it offers exceptional flexibility as a potential 4th bedroom, private guest suite, in-law suite, home office, or creative space. The 3rd full bath also serves as a convenient pool bath with direct outdoor access to the lanai. Outside, enjoy beautifully maintained gardens, mature trees, a fully fenced backyard, abundant outdoor living space, and a large detached storage building with electricity. Residents also enjoy private access to Black Lake and Lake Tilden, complete with a boat ramp, tennis court, pavilion, and the peaceful charm of one of Winter Garden's hidden-gem communities. Just minutes from Winter Garden Village, historic Downtown Winter Garden, major highways, area hospitals, and world-famous attractions including Disney World, Universal Orlando, and SeaWorld, this property delivers a combination of land, location, and lifestyle that is rare to find.

14140 Country Estate Drive, Winter Garden
$1,149,000
4 Beds ⋅ 2 Baths ⋅ Mt Park Orange Grove SubDv. ⋅ 34787 Zip Code
PRICE IMPROVEMENT! Rare opportunity to own 6.8 acres in the heart of Horizon West! Zoned A1 with NO HOA. Zoned for top rated schools. Bring your horses, goats, chickens and build your dream home. The property is located at the end of a dead end street. Very private and isolated. One side of the property is flanked by retention ponds, the other side is the future home of a community park, and far in the backyard is Hamlin Elementary and Middle Schools. The home has been gutted and ready to customize your ideal floor plan. Plenty of room on the land to add a barn, ADU, or workshop. The lot contains wetland so a pond ebbs and flows on the property bringing all sorts of life to the land. Enjoy the tranquil ranch life with beautiful sunsets while remaining within minutes of shopping, restaurants, Disney, and access to the 429. Refer to Orange County Land Use Table for property use. Check with county to verify all current and future use.

17425 Lake Ingram Road, Winter Garden
$745,000
4 Beds ⋅ 3 Baths ⋅ Watermark Ph 2c SubDv. ⋅ 34787 Zip Code
Welcome to Watermark in Winter Garden one of the most sought-after, resort-style communities in Horizon West. This energy-efficient Meritage home has 4 bedrooms, 2.5 baths, and a super functional layout with high ceilings and great natural light throughout. As soon as you pull up, you’ll notice the stone accents on the exterior, brick paver driveway, and clean curb appeal. Inside, the home has been freshly painted and updated with new luxury vinyl plank flooring upstairs, giving it a modern feel without the maintenance headaches. The layout just makes sense 3 bedrooms and a versatile loft upstairs (perfect for a media room, office, or playroom), and a 4th bedroom downstairs that works great for guests or a private home office. The open-concept kitchen seamlessly connects to the main living area and features granite countertops, ample cabinetry, and an easy flow out to the backyard making it ideal for everyday living or having people over. Out back is where this one really stands out. If you're looking for a backyard oasis, look no further. This home has no rear neighbors backing to a retention pond and conservation beyond that. The pool deck is over 1300 square feet with a heated 6 foot deep 484 square foot custom saltwater pool! Enjoy sunsets, watching Disney fireworks at night or the occasional rocket launch in the distance! It’s a great setup for relaxing or entertaining. Watermark has some of the best amenities around resort-style pool, splash pad, gym, clubhouse, tennis, basketball, dog park, and tons of walking and biking trails. You’re also within walking distance to restaurants and just a short drive to Disney, shopping, and everything Winter Garden and Horizon West have to offer. If you’re looking for a clean, move-in ready home in a great location with a strong lifestyle, this one checks all the boxes!

9256 Grand Island Way, Winter Garden
$3,470,000
5 Beds ⋅ 6 Baths ⋅ Briley Farm - Phase 1b SubDv. ⋅ 34787 Zip Code
Pre-Construction. To be built. Pre Construction. To be Built. Briley Farm rests comfortably on 111 acres of lush landscape in the beautiful town of Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! Each residence will be meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room, planned to be airy yet cozy and ready for your personal touch. At Briley Farm, you'll find a seamless combination of residential luxury and convenience, with homes built for enjoying the best of indoor and outdoor living. Briley Farm boasts serene scenery as a picturesque back drop for new home construction, while still near shopping, restaurants, and major highways. At Briley Farm you'll discover comfortable countryside living under a canopy of welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

521 N Pollard Street, Oakland
$3,894,945
6 Beds ⋅ 7 Baths ⋅ Briley Farm - Phase 1b SubDv. ⋅ 34787 Zip Code
Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres of lush landscape in the beautiful town of Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! Each residence will be meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room, planned to be airy yet cozy and ready for your personal touch. At Briley Farm, you'll find a seamless combination of residential luxury and convenience, with homes built for enjoying the best of indoor and outdoor living. Briley Farm boasts serene scenery as a picturesque back drop for new home construction, while still near shopping, restaurants, and major highways. At Briley Farm you'll discover comfortable countryside living under a canopy of welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

517 N Pollard Street, Oakland
$600,000
3 Beds ⋅ 2 Baths ⋅ Woodbridge On Green SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful single-story home in the desirable Woodbridge on the Green community in Winter Garden, FL. Offering 3 bedrooms, 2 bathrooms, and 2,472 square feet of living space (3,330 total), this residence blends comfort, functionality, and scenic beauty. Step inside to discover a spacious layout designed for easy living and entertaining. The home provides breathtaking views of the pond and golf course, while mature trees provide shade and privacy—creating the perfect backdrop for enjoying stunning afternoon sunsets. The home features a rare 2.5-car garage, including a side golf cart garage door and an air-conditioned storage area—ideal for hobbies, extra storage, or a workshop setup. Enjoy a low-maintenance lifestyle with HOA benefits that include lawn/irrigation care and exterior home painting, along with access to a dedicated community storage lot for boats and RVs. All of this allows for a clean and well-maintained looking community. Perfectly located near shopping, dining, and everyday conveniences, this home offers both tranquility and accessibility in one of Winter Garden’s most sought-after communities. Don’t miss your opportunity to own a home with exceptional views and unmatched convenience—schedule your private showing today!

4136 Willow Bay Drive, Winter Garden
$465,000
3 Beds ⋅ 2 Baths ⋅ Island Pointe Sub SubDv. ⋅ 34787 Zip Code
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.

1035 Chase Drive, Winter Garden
$540,000
3 Beds ⋅ 3 Baths ⋅ Silverleaf Reserve Bungalows SubDv. ⋅ 34787 Zip Code
Located in the highly desirable Silverleaf at Hamlin in Winter Garden, this exceptional bungalow offers the perfect blend of location, lifestyle, and design. Surrounded by top-rated schools within short distance, premier dining, and a rapidly growing area with strong appreciation, this is one of the most sought-after communities in the region. This beautifully designed home features 3 bedrooms, 2/1 bathrooms, and an additional loft room, with a layout that is both functional and inviting. What truly sets this property apart is its interior. Unlike anything else currently available in the area, this home has been fully customized with high-end finishes and a cohesive, thoughtfully curated design throughout. Every element was carefully selected to create a seamless flow of elegance, comfort, and functionality. The home showcases custom-built cabinetry in every space, including closets, storage solutions, and integrated desk areas, all designed specifically for the home. The custom-made curtains were designed to fit each space perfectly, enhancing both aesthetics and comfort. Throughout the home, you’ll find LED lighting and carefully selected fixtures that complement one another, creating a warm, modern, and visually harmonious atmosphere. Custom mirrors, wood panel details, and built-in elements elevate each room, making every space feel intentional and refined. The kitchen is a true highlight a gourmet, built-in design that is highly practical, ideal for everyday living and entertaining. This is a rare opportunity to own a home that is completely move-in ready at a level rarely found, and everything has already been done with impeccable taste. Simply bring your belongings and start living. Homes like this are truly one of a kind in the area, and once you step inside, it’s impossible not to fall in love.

4863 Lacewing Drive, Winter Garden
$786,865
4 Beds ⋅ 3 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Sold Data Entry Only.

16783 Muskgrass Drive, Winter Garden
$650,000
3 Beds ⋅ 2 Baths ⋅ 0000 SubDv. ⋅ 34787 Zip Code
Rare opportunity in Winter Garden! This property sits on approximately one acre with no HOA, offering exceptional space, flexibility, and privacy in a highly desirable location. Conveniently located just minutes from Downtown Winter Garden), with easy access to major roadways, shopping, dining, and top-rated schools—and even the option to ride your golf cart into downtown to enjoy everything the area has. The expansive lot provides ample room for RVs, boats, recreational vehicles, and more, making it ideal for those seeking additional space and versatility. The home features generous living areas and a functional layout with great potential for customization or renovation. Outdoor amenities include a private pool, hot tub, and an extended driveway with plenty of parking space. Located approximately 2 miles from Lake Apopka and about 3 miles from Downtown Winter Garden. Properties with this amount of land and no HOA in this area are rare—schedule your showing today!

1261 E Fullers Cross Road, Winter Garden
$865,000
5 Beds ⋅ 5 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
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 include stainless steel appliances, making cooking a piece of cake. Located off the family room is a bedroom with a full bathroom. As you 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. *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.*

11264 Hollow Bay Drive, Winter Garden
$735,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Waterleigh presents the Cresswell. This two-story all concrete block construction single-family home features 5 bedrooms and 4 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you’ll find a bedroom and downstairs bathroom. The well-appointed kitchen overlooking the great room, dining room, and oversized outdoor lanai. The kitchen features quartz countertops, stainless steel appliances, spacious walk-in pantry and an island with bar seating. As we head up to the second floor, we are greeted with a loft area and four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Customize the second floor of this home to create a space that meets your needs but transforming the loft area to a fifth bedroom with full bath or Guest Suite with ensuite bathroom. *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.*

18053 Cider Mill Lane, Winter Garden
$658,000
4 Beds ⋅ 4 Baths ⋅ Encore/Ovation Ph 3 SubDv. ⋅ 34787 Zip Code
Crafted by MI Homes in the exclusive community of Encore at Ovation you will find 12513 Encore At Ovation Way, a gorgeous Wekiva model loaded with upgrades. The impressive floorplan is open and bright featuring neutral tones as the perfect base for your personal touches. The first floor boasts woodgrain tile throughout the main living areas. The kitchen goes well beyond functional with gorgeous upgrades including 42-inch cabinets, several glass front cabinet doors, tile backsplash, stainless steel drop-in farm sink, gas range, stainless steel appliances, frosted glass pantry door, and a huge breakfast bar. The family room, kitchen, dining room, guest bedroom, a full bath and power room are located on the first floor. Climb the beautiful staircase to find the large loft area, two additional bedrooms, a full bath, the laundry room, and the luxurious master suite with a cove ceiling, free standing tub, separate shower, and large walk-in closet. The covered front porch is ideal to relax and enjoy the beautiful pond view across the street, and the covered patio is the perfect place for a quite evening dinner. This home is built with features that meet the Energy Star® 3.1 home building requirements, saving you on the cost of ownership. It’s also backed by M/I Homes' industry leading 10-Year Transferable Warranty. This home has been maintained to perfection and is ready for new owners.

12513 Encore At Ovation Way, Winter Garden
$485,000
3 Beds ⋅ 2 Baths ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to 16716 Wingspread Loop, a beautifully maintained single-story home in the highly sought-after Hawksmoor community of Winter Garden. Built in 2019 and cared for by its original owner, this 3-bedroom, 2-bath residence is move-in ready with thoughtful upgrades throughout. The open layout creates an easy flow between the kitchen, dining, and living areas. The kitchen features warm honey-toned cabinetry, granite countertops, and generous storage. The spacious primary suite serves as a private retreat with a large bedroom, walk-in closet, and an en-suite bath with quartz countertops. Additional highlights include built-in cabinetry in the laundry room, with the washer and dryer conveying for added convenience. Enjoy Florida living outdoors on the private patio, perfect for relaxing or hosting friends. The two-car garage includes a durable epoxy-coated floor, and the paved driveway enhances the home’s curb appeal. All kitchen and laundry appliances are included. Located along Avalon Road, this home places you just minutes from Hamlin Town Center, Flamingo Crossings, Walt Disney World, FL-429, Orange County National Golf Center, Clermont, Windermere, and top-rated Orange County schools. Residents of Hawksmoor enjoy a variety of resort-style amenities, including a clubhouse with rentable event space, fitness center, pool and splash pad, outdoor summer kitchen and grill, yoga lawn, shaded playground, dog park, and scenic walking paths. Schedule your private showing today and experience everything this Winter Garden home has to offer. Transferable lifetime termite contract from Massey available.

16716 Wingspread Loop, Winter Garden
$1,225,000
5 Beds ⋅ 7 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
Within the gated community of Canopy Oaks in Winter Garden, Parade of Homes award-winning Delray model by renowned builder A.R. Bailey Homes combines timeless architecture with curated upgrades rarely found in today’s market. Within an intimate enclave of only 49 homesites, this meticulously maintained home offers over 4,000 square feet of flexible multigenerational living, entertaining spaces and seamless indoor-outdoor Florida living. Ideally just minutes from Historic Downtown Winter Garden, Winter Garden Village, Orlando Health, the Roper YMCA, shopping, dining, recreation and major roadways including Florida’s Turnpike, SR 429, SR 408 and Interstate 4. A paver driveway, concrete tile roof, stone-accented exterior, wood-look garage doors, three-car garage and grand solid wood double-entry doors create a striking first impression. Inside, 10-foot ceilings in the great room, architectural details, abundant natural light, elegant finishes, and wood-look porcelain tile flooring throughout the first floor create a sophisticated yet welcoming atmosphere. The chef’s kitchen serves as the heart of the home, designed for everyday living and entertaining. Highlights include a natural gas cooktop with exterior vent, built-in wall oven, upgraded appliances, pot filler, oversized center island, 42-inch cabinetry with crown molding, under-cabinet lighting, designer tile backsplash and an expansive walk-in pantry overlooking the coffered-ceiling great room. A gated wine cellar adds a distinctive feature rarely found at this price point. The luxurious first-floor primary suite was designed as a spa-inspired retreat, featuring a beautifully appointed primary bath with premium finishes, dual vanities, an oversized walk-in shower, freestanding soaking tub and a spacious walk-in closet. A separate first-floor en-suite bedroom provides flexibility for guests, extended family, multigenerational living or a private home office. Upstairs, a second primary suite is complemented by two additional en-suite bedrooms, a spacious loft, guest powder bath and covered balcony, providing privacy and versatility for family and guests. Designed to embrace Florida’s indoor-outdoor lifestyle, dramatic corner-opening glass doors and expansive stacking sliders open to the covered lanai with a motorized retractable screen, creating effortless entertaining year-round. The backyard, accented by a stucco privacy wall, offers ample space for a custom pool, outdoor kitchen and additional outdoor living areas. The three-car garage provides generous space for vehicles, golf carts, storage and recreational equipment. Additional highlights include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, mudroom, reading nook and generous storage throughout. Residents of Canopy Oaks enjoy scenic recreational trails, a community playground and an exceptional Winter Garden location near shopping, dining, healthcare, recreation and everyday conveniences. Offering five en-suite bedrooms, seven baths, dual primary suites, a spa-inspired first-floor primary suite, wood-look porcelain tile throughout the first floor, a three-car garage, natural gas, award-winning design and an exceptional location within Canopy Oaks, this beautifully maintained residence presents an outstanding opportunity to experience refined Winter Garden living. Also available for lease (MLS #O6416527).

706 Canopy Estates Drive, Winter Garden