Homesinorlando.forsale Search Results

$1,170,000

NEW PRICE and Brand New Renewal by Anderson Double Paned Windows coming soon ($60,000 value)!!! Welcome to Courtlea Oaks, one of Winter Garden’s most timeless and charming communities, perfectly positioned in the heart of the golf cart district. This beautiful 4-bedroom, 2.5-bath home with a 3-car garage and screened pool has been freshly painted inside and out, offering a bright, clean, move-in-ready feel from the moment you arrive. Inside, you’ll love the functional layout featuring a downstairs office, formal dining room, and spacious family room—plus a stunning open entry with soaring ceilings that extend to the second floor, creating an airy, grand feel. The home also features a generously sized primary suite, complete with a newly renovated bathroom and a spacious walk-in closet—your own private retreat. Upstairs, a versatile loft/bonus space provides the perfect flex area for a media room, playroom, or second living space. Step outside to your backyard oasis with a screened-in pool, ideal for relaxing and entertaining year-round. Enjoy being just minutes from Historic Downtown Winter Garden, with its boutique shopping, casual and fine dining, the Saturday Farmers Market, local breweries, the Winter Garden Theatre, and the West Orange Trail. Conveniently located near major highways including 408, 429, and the Florida Turnpike for an easy commute. Don’t miss your opportunity to own in Courtlea Oaks—schedule your private showing today!

4 Beds ⋅ 3 Baths ⋅ Courtlea Oaks SubDv. ⋅ 34787 Zip Code

NEW PRICE and Brand New Renewal by Anderson Double Paned Windows coming soon ($60,000 value)!!! Welcome to Courtlea Oaks, one of Winter Garden’s most timeless and charming communities, perfectly positioned in the heart of the golf cart district. This beautiful 4-bedroom, 2.5-bath home with a 3-car garage and screened pool has been freshly painted inside and out, offering a bright, clean, move-in-ready feel from the moment you arrive. Inside, you’ll love the functional layout featuring a downstairs office, formal dining room, and spacious family room—plus a stunning open entry with soaring ceilings that extend to the second floor, creating an airy, grand feel. The home also features a generously sized primary suite, complete with a newly renovated bathroom and a spacious walk-in closet—your own private retreat. Upstairs, a versatile loft/bonus space provides the perfect flex area for a media room, playroom, or second living space. Step outside to your backyard oasis with a screened-in pool, ideal for relaxing and entertaining year-round. Enjoy being just minutes from Historic Downtown Winter Garden, with its boutique shopping, casual and fine dining, the Saturday Farmers Market, local breweries, the Winter Garden Theatre, and the West Orange Trail. Conveniently located near major highways including 408, 429, and the Florida Turnpike for an easy commute. Don’t miss your opportunity to own in Courtlea Oaks—schedule your private showing today!

308 Forest Haven Drive, Winter Garden

$930,000

One or more photo(s) has been virtually staged. Virtually staged. Wake each morning to tranquil lake views and soft natural light that set a serene tone for the day. Built in 2021, this refined residence is positioned on an expansive premium lot within Winter Garden’s sought-after Hawksmoor community, offering the rare luxury of no rear or front neighbors—only open space, conservation views, and uninterrupted privacy. The paved driveway and oversized three-car garage create an impressive arrival and hint at the thoughtfully designed interiors beyond. Inside, soaring ceilings and an open, light-filled layout create an effortless sense of elegance and flow. At the center of the home, the chef-inspired kitchen makes a striking statement with a waterfall island, gleaming quartz countertops, 42-inch cabinetry, and stainless steel appliances—perfectly suited for both intimate mornings and entertaining. From the main living areas, expansive windows frame breathtaking sunset views across the lake and conservation land, seamlessly blending indoor and outdoor living. French doors open to a private office or fifth bedroom featuring a versatile bonus nook—ideal for a home office, creative studio, or serene retreat. Upstairs, a spacious loft provides endless flexibility, whether envisioned as a media lounge, game room, or additional living space. The primary suite is a true sanctuary, highlighted by elegant tray ceilings, dual walk-in closets, and remote-controlled blinds that allow you to reveal the picturesque views at your leisure. Outdoors, the covered lanai invites relaxed evenings and elevated entertaining, all set against the calming backdrop of water and nature. Residents of Hawksmoor enjoy resort-style amenities including a sparkling pool, splash pad, state-of-the-art fitness center, and scenic walking trails. Ideally located just minutes from SR 429, Hamlin Town Center, historic downtown Winter Garden, and world-renowned theme parks, this home offers the perfect balance of privacy, luxury, and convenience

5 Beds ⋅ 3 Baths ⋅ Hawksmoor Ph 4 SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Virtually staged. Wake each morning to tranquil lake views and soft natural light that set a serene tone for the day. Built in 2021, this refined residence is positioned on an expansive premium lot within Winter Garden’s sought-after Hawksmoor community, offering the rare luxury of no rear or front neighbors—only open space, conservation views, and uninterrupted privacy. The paved driveway and oversized three-car garage create an impressive arrival and hint at the thoughtfully designed interiors beyond. Inside, soaring ceilings and an open, light-filled layout create an effortless sense of elegance and flow. At the center of the home, the chef-inspired kitchen makes a striking statement with a waterfall island, gleaming quartz countertops, 42-inch cabinetry, and stainless steel appliances—perfectly suited for both intimate mornings and entertaining. From the main living areas, expansive windows frame breathtaking sunset views across the lake and conservation land, seamlessly blending indoor and outdoor living. French doors open to a private office or fifth bedroom featuring a versatile bonus nook—ideal for a home office, creative studio, or serene retreat. Upstairs, a spacious loft provides endless flexibility, whether envisioned as a media lounge, game room, or additional living space. The primary suite is a true sanctuary, highlighted by elegant tray ceilings, dual walk-in closets, and remote-controlled blinds that allow you to reveal the picturesque views at your leisure. Outdoors, the covered lanai invites relaxed evenings and elevated entertaining, all set against the calming backdrop of water and nature. Residents of Hawksmoor enjoy resort-style amenities including a sparkling pool, splash pad, state-of-the-art fitness center, and scenic walking trails. Ideally located just minutes from SR 429, Hamlin Town Center, historic downtown Winter Garden, and world-renowned theme parks, this home offers the perfect balance of privacy, luxury, and convenience

16975 Wingspread Loop, Winter Garden

$810,000

Homes like this rarely come to market. Located behind the gates of the highly sought-after Carriage Pointe community in Winter Garden, this pool home delivers west-facing sunsets, a premium lot with no rear neighbors, and a level of updates that checks every box. Set on an oversized homesite, this Ravenwood floor plan by Taylor Morrison offers exceptional curb appeal with a covered front porch, expansive driveway, and a 3-car garage. Step through the double door front entry into soaring ceilings and one of the most functional layouts, featuring 5 bedrooms, a dedicated office, and an upstairs bonus room. The primary and 3 guest bedrooms are located on the first floor. French doors lead to a front-facing dedicated home office. The office is adjacent to the formal dining room. The open concept great room features a wall of sliding glass doors that frame stunning views of the private, screened, heated saltwater pool, pond, and conservation. The kitchen, renovated in 2023 with quartz countertops, a new backsplash and soft close cabinetry, opens seamlessly to the great room. It also features 42-inch wood cabinetry, a center island, and all new appliances. Upstairs offers an ideal suite or teen retreat with a full bedroom, bathroom, and a spacious 21’ x 14’ loft overlooking the rear views. This home has been meticulously maintained and extensively upgraded, including a newer roof (2021), all windows have been replaced and come with a transferable warranty. The windows are double-pane, hurricane-rated, energy-efficient vinyl windows. Both HVAC systems have been replaced, all bathrooms have been updated, new pool equipment, exterior repainted in 2023, gutters added, semi-custom closets, no carpet in the bedrooms, an active termite bond, and MORE! Inquire for a full list of upgrades and features of the home. The oversized side yard provides ample space for pets and play. Carriage Pointe offers a gated entrance and amenities including a park, playground, and tennis courts, all just minutes from shopping, dining, and the 429 Expressway. The community is zoned for highly sought-after K–12 public schools with numerous private school options also nearby. Call today to schedule your private tour.

5 Beds ⋅ 4 Baths ⋅ Carriage Pointe SubDv. ⋅ 34787 Zip Code

Homes like this rarely come to market. Located behind the gates of the highly sought-after Carriage Pointe community in Winter Garden, this pool home delivers west-facing sunsets, a premium lot with no rear neighbors, and a level of updates that checks every box. Set on an oversized homesite, this Ravenwood floor plan by Taylor Morrison offers exceptional curb appeal with a covered front porch, expansive driveway, and a 3-car garage. Step through the double door front entry into soaring ceilings and one of the most functional layouts, featuring 5 bedrooms, a dedicated office, and an upstairs bonus room. The primary and 3 guest bedrooms are located on the first floor. French doors lead to a front-facing dedicated home office. The office is adjacent to the formal dining room. The open concept great room features a wall of sliding glass doors that frame stunning views of the private, screened, heated saltwater pool, pond, and conservation. The kitchen, renovated in 2023 with quartz countertops, a new backsplash and soft close cabinetry, opens seamlessly to the great room. It also features 42-inch wood cabinetry, a center island, and all new appliances. Upstairs offers an ideal suite or teen retreat with a full bedroom, bathroom, and a spacious 21’ x 14’ loft overlooking the rear views. This home has been meticulously maintained and extensively upgraded, including a newer roof (2021), all windows have been replaced and come with a transferable warranty. The windows are double-pane, hurricane-rated, energy-efficient vinyl windows. Both HVAC systems have been replaced, all bathrooms have been updated, new pool equipment, exterior repainted in 2023, gutters added, semi-custom closets, no carpet in the bedrooms, an active termite bond, and MORE! Inquire for a full list of upgrades and features of the home. The oversized side yard provides ample space for pets and play. Carriage Pointe offers a gated entrance and amenities including a park, playground, and tennis courts, all just minutes from shopping, dining, and the 429 Expressway. The community is zoned for highly sought-after K–12 public schools with numerous private school options also nearby. Call today to schedule your private tour.

1826 Jean Marie Drive, Winter Garden

$767,000

One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3.5-bath home located in the peaceful and highly desirable Story Grove community. Positioned on one of the largest lots in the neighborhood and situated on a quiet street, this home offers exceptional privacy with no homes in front or behind. The first floor features an open and spacious layout with elegant ceramic tile throughout. The bright kitchen offers granite countertops, 42-inch cabinets, a walk-in pantry, and a dedicated coffee bar area—perfect for everyday living and entertaining. The primary suite is conveniently located on the first floor and includes a walk-in closet and a private en-suite bathroom with dual sinks, a soaking tub, a separate shower, and an enclosed toilet area. Large windows provide tranquil views of the patio and conservation area. Also on the first level are a guest half bath, a front-facing office ideal for working from home, and a spacious laundry room. Upstairs, you’ll find a second primary bedroom with its own private bathroom, perfect for guests or multigenerational living. A large bonus room offers flexible space for a family room, media room, or entertainment area. A third full bathroom with double sinks and a private toilet area completes the second floor. Sliding glass doors from the living area lead to a spacious terrace overlooking the fully fenced backyard and conservation area, offering complete privacy—ideal for outdoor gatherings, relaxing, or enjoying Florida’s year-round sunshine. Story Grove offers resort-style amenities including a community pool, playground, basketball court, fitness center, dog park, walking trails, and a community center with regular events. The monthly HOA includes lawn maintenance. Zoned for great schools and conveniently located just minutes from Walt Disney World, Hamlin shopping center, SR-429, restaurants, supermarkets, and hospitals.

4 Beds ⋅ 4 Baths ⋅ Storey Grove Ph 3 SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 3.5-bath home located in the peaceful and highly desirable Story Grove community. Positioned on one of the largest lots in the neighborhood and situated on a quiet street, this home offers exceptional privacy with no homes in front or behind. The first floor features an open and spacious layout with elegant ceramic tile throughout. The bright kitchen offers granite countertops, 42-inch cabinets, a walk-in pantry, and a dedicated coffee bar area—perfect for everyday living and entertaining. The primary suite is conveniently located on the first floor and includes a walk-in closet and a private en-suite bathroom with dual sinks, a soaking tub, a separate shower, and an enclosed toilet area. Large windows provide tranquil views of the patio and conservation area. Also on the first level are a guest half bath, a front-facing office ideal for working from home, and a spacious laundry room. Upstairs, you’ll find a second primary bedroom with its own private bathroom, perfect for guests or multigenerational living. A large bonus room offers flexible space for a family room, media room, or entertainment area. A third full bathroom with double sinks and a private toilet area completes the second floor. Sliding glass doors from the living area lead to a spacious terrace overlooking the fully fenced backyard and conservation area, offering complete privacy—ideal for outdoor gatherings, relaxing, or enjoying Florida’s year-round sunshine. Story Grove offers resort-style amenities including a community pool, playground, basketball court, fitness center, dog park, walking trails, and a community center with regular events. The monthly HOA includes lawn maintenance. Zoned for great schools and conveniently located just minutes from Walt Disney World, Hamlin shopping center, SR-429, restaurants, supermarkets, and hospitals.

11120 Robert Frost Drive, Winter Garden

$1,200,000

Behind the private gates of the highly sought-after Waterside on Johns Lake community in Winter Garden, this exceptional and extensively updated estate offers a rare blend of refined luxury, thoughtful architectural design, and seamless indoor-outdoor living. Designed to impress, this five-bedroom residence lives primarily as a single-story home, complemented by a private upstairs retreat featuring a spacious loft, full bedroom, and bathroom—ideal for guests, multi-generational living, or a secluded home office. From the moment you enter, the home exudes timeless sophistication. Authentic solid wood flooring flows throughout, creating warmth and character that elevate every space. Expanded living areas provide a bright, open layout perfectly suited for both intimate daily living and elegant entertaining. Luxury countertops define the gourmet kitchen and gathering spaces, blending modern elegance with classic craftsmanship. The home is thoughtfully designed for true Florida living, with interiors opening seamlessly to an expansive screened-in lanai, creating a year-round indoor-outdoor lifestyle. Electric automatic blinds in the living room allow effortless control of natural light, while the fully fenced backyard reveals a stunning infinity-edge pool, offering a resort-style atmosphere ideal for relaxation and entertaining. Inside, the residence continues to impress with custom built-in cabinetry, high-end finishes, and a floor plan that balances functionality with refined design. Five generously sized bedrooms and beautifully appointed bathrooms are thoughtfully positioned to maximize privacy, comfort, and flow throughout the home. Located within gated Waterside, one of Winter Garden’s most desirable lakefront communities, residents enjoy privacy, exclusivity, and direct access to Johns Lake, while remaining conveniently close to top-rated schools, dining, shopping, and major roadways. This is more than a home—it is a lifestyle, defined by space, craftsmanship, and exceptional outdoor living. Opportunities of this caliber on Johns Lake are truly rare, and this residence stands apart in both design and execution.

5 Beds ⋅ 5 Baths ⋅ Waterside/Johns Lk-Ph 1 SubDv. ⋅ 34787 Zip Code

Behind the private gates of the highly sought-after Waterside on Johns Lake community in Winter Garden, this exceptional and extensively updated estate offers a rare blend of refined luxury, thoughtful architectural design, and seamless indoor-outdoor living. Designed to impress, this five-bedroom residence lives primarily as a single-story home, complemented by a private upstairs retreat featuring a spacious loft, full bedroom, and bathroom—ideal for guests, multi-generational living, or a secluded home office. From the moment you enter, the home exudes timeless sophistication. Authentic solid wood flooring flows throughout, creating warmth and character that elevate every space. Expanded living areas provide a bright, open layout perfectly suited for both intimate daily living and elegant entertaining. Luxury countertops define the gourmet kitchen and gathering spaces, blending modern elegance with classic craftsmanship. The home is thoughtfully designed for true Florida living, with interiors opening seamlessly to an expansive screened-in lanai, creating a year-round indoor-outdoor lifestyle. Electric automatic blinds in the living room allow effortless control of natural light, while the fully fenced backyard reveals a stunning infinity-edge pool, offering a resort-style atmosphere ideal for relaxation and entertaining. Inside, the residence continues to impress with custom built-in cabinetry, high-end finishes, and a floor plan that balances functionality with refined design. Five generously sized bedrooms and beautifully appointed bathrooms are thoughtfully positioned to maximize privacy, comfort, and flow throughout the home. Located within gated Waterside, one of Winter Garden’s most desirable lakefront communities, residents enjoy privacy, exclusivity, and direct access to Johns Lake, while remaining conveniently close to top-rated schools, dining, shopping, and major roadways. This is more than a home—it is a lifestyle, defined by space, craftsmanship, and exceptional outdoor living. Opportunities of this caliber on Johns Lake are truly rare, and this residence stands apart in both design and execution.

16740 Turtle Hatch Drive, Winter Garden

$570,000

GATED COMMUNITY !! ENTICING CURB APPEAL !! 3 CAR GARAGE !! Welcome home to Carriage Pointe !! One of the most highly desired communities in Winter Garden !! This home has beautifully manicured lush landscaping and complimented by a BRICK PAVER DRIVEWAY AND WALK leading to the COVERED FRONT PORCH with DOUBLE LEADED GLASS ENTRY DOORS !! ROOF 2022 !! This 4 bed/ 3 bath VERSATILE FLOOR PLAN boasts 2,916 climate controlled sq. ft. The grand foyer with SOARING CEILINGS opens to the formal Living Room and the elegant trey ceiling Dining Room both providing plentiful NATURAL LIGHT !! The chef friendly kitchen has ABUNDANT CABINETRY, granite counters, tasteful backsplash, SS appliances, BREAKFAST BAR ISLAND and spacious Dinette/Nook that flows seamlessly into the oversized Family Room that overlooks the lanai. The EXPANSIVE PRIMARY ENSUITE has a trey ceiling, bay window-sitting area, an enormous walk-in closet, dual vanities, garden tub and large shower stall. The opposite side of the home has two additional bedrooms with a shared bath, and a GUEST SUITE complete with full bath and separate entry. The SCREENED LANAI overlooks the backyard with a HOT TUB !! The community has a tennis court, playground, soccer field and walking path. Location benefits include close drive to Disney/Theme parks, shopping, Toll 429, and numerous activities in downtown HISTORIC WINTER GARDEN !! Make this home your new address !!

4 Beds ⋅ 3 Baths ⋅ Carriage Pointe A-I & L SubDv. ⋅ 34787 Zip Code

GATED COMMUNITY !! ENTICING CURB APPEAL !! 3 CAR GARAGE !! Welcome home to Carriage Pointe !! One of the most highly desired communities in Winter Garden !! This home has beautifully manicured lush landscaping and complimented by a BRICK PAVER DRIVEWAY AND WALK leading to the COVERED FRONT PORCH with DOUBLE LEADED GLASS ENTRY DOORS !! ROOF 2022 !! This 4 bed/ 3 bath VERSATILE FLOOR PLAN boasts 2,916 climate controlled sq. ft. The grand foyer with SOARING CEILINGS opens to the formal Living Room and the elegant trey ceiling Dining Room both providing plentiful NATURAL LIGHT !! The chef friendly kitchen has ABUNDANT CABINETRY, granite counters, tasteful backsplash, SS appliances, BREAKFAST BAR ISLAND and spacious Dinette/Nook that flows seamlessly into the oversized Family Room that overlooks the lanai. The EXPANSIVE PRIMARY ENSUITE has a trey ceiling, bay window-sitting area, an enormous walk-in closet, dual vanities, garden tub and large shower stall. The opposite side of the home has two additional bedrooms with a shared bath, and a GUEST SUITE complete with full bath and separate entry. The SCREENED LANAI overlooks the backyard with a HOT TUB !! The community has a tennis court, playground, soccer field and walking path. Location benefits include close drive to Disney/Theme parks, shopping, Toll 429, and numerous activities in downtown HISTORIC WINTER GARDEN !! Make this home your new address !!

1923 Jean Marie Drive, Winter Garden

$2,098,000

Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!

4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!

1258 Ridge Lake Way, Oakland

$999,000

BETTER THAN BRAND NEW! Welcome home to 1185 Wilder Oaks Way, ideally located in the coveted and quaint neighborhood of Oakland Park. This barely lived-in highly desirable Seaside floor plan presents an exclusive opportunity to own a fully turn-key home showcasing an extensive collection of top-tier builder upgrades complemented by thoughtful owner enhancements (see attached list). Opportunities like this are rare, as there are no remaining options to build new construction by David Weekley within Oakland Park. Designed for both elegance and livability, the home offers a first-floor primary suite with a walk-in closet, three additional bedrooms and a spacious loft upstairs. Premium builder upgrades include an enclosed office with glass French doors, a designer kitchen with cabinetry extended to the ceiling, luxury white quartz slab countertops, a 36” gas GE cooktop, architectural details such as crown molding and 5” baseboards and more! Luxury Mohawk flooring flows seamlessly throughout the entire first floor and stairway, creating a cohesive and elevated aesthetic. Every detail has been carefully considered, from custom Hunter Douglas Duette top-down blinds on every window, offering both privacy and light control, to custom closet shelving in every closet for exceptional organization. Kichler ceiling fans in every room provide comfort and efficiency, while the three-bay garage connects to a rare 20-foot driveway and is enhanced with epoxied floors and overhead storage. Experience the signature Oakland Park lifestyle, defined by front porch living, walkability, lush green spaces, two resort-style community pools, and direct access to the West Orange Trail. Located within the golf-cart district, historic downtown Winter Garden is just moments away, offering dining, boutique shopping, the weekly farmers market, and year-round community events. Less than a 5 minute drive to the Florida Turnpike. This is the perfect home, in the perfect neighborhood.

4 Beds ⋅ 4 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code

BETTER THAN BRAND NEW! Welcome home to 1185 Wilder Oaks Way, ideally located in the coveted and quaint neighborhood of Oakland Park. This barely lived-in highly desirable Seaside floor plan presents an exclusive opportunity to own a fully turn-key home showcasing an extensive collection of top-tier builder upgrades complemented by thoughtful owner enhancements (see attached list). Opportunities like this are rare, as there are no remaining options to build new construction by David Weekley within Oakland Park. Designed for both elegance and livability, the home offers a first-floor primary suite with a walk-in closet, three additional bedrooms and a spacious loft upstairs. Premium builder upgrades include an enclosed office with glass French doors, a designer kitchen with cabinetry extended to the ceiling, luxury white quartz slab countertops, a 36” gas GE cooktop, architectural details such as crown molding and 5” baseboards and more! Luxury Mohawk flooring flows seamlessly throughout the entire first floor and stairway, creating a cohesive and elevated aesthetic. Every detail has been carefully considered, from custom Hunter Douglas Duette top-down blinds on every window, offering both privacy and light control, to custom closet shelving in every closet for exceptional organization. Kichler ceiling fans in every room provide comfort and efficiency, while the three-bay garage connects to a rare 20-foot driveway and is enhanced with epoxied floors and overhead storage. Experience the signature Oakland Park lifestyle, defined by front porch living, walkability, lush green spaces, two resort-style community pools, and direct access to the West Orange Trail. Located within the golf-cart district, historic downtown Winter Garden is just moments away, offering dining, boutique shopping, the weekly farmers market, and year-round community events. Less than a 5 minute drive to the Florida Turnpike. This is the perfect home, in the perfect neighborhood.

1185 Wilder Oaks Way, Oakland

$1,725,000

Discover the pinnacle of custom-built luxury in Winter Garden with this spectacular 5-bedroom, 3-bathroom Modern Farmhouse, crafted by the esteemed Justice & Wood Builders. This home is situated within Oakland Hills, a truly exclusive enclave of just 17 homesites, offering a private and peaceful lifestyle while remaining mere moments from the energy of Historic Downtown Winter Garden. Set on a rare and expansive 0.47-acre lot, the property is graced by the majestic, moss-draped canopy of towering old oak trees, creating an idyllic, tranquil setting from the moment you arrive. Step inside to an airy, open-concept living space where natural light floods the wide-plank wood floors. The heart of the home is defined by dramatic cathedral ceilings, beautifully accentuated by rich, exposed timber ceiling beams. The kitchen is a masterful fusion of high design and functionality—a space that moves beyond standard "gourmet." It features premium shaker cabinetry, a massive center island finished in a striking blue-gray hue for contrast, and luxurious quartz countertops. Chefs will appreciate the professional stainless steel appliances, the deep farmhouse sink, and the dedicated natural gas range for precision cooking. The home's thoughtfully designed layout provides versatile living areas for every need. The three-car garage offers not just ample storage and parking, but the convenience of an EV adapter in the third bay, ready for your electric vehicle. Escape to the generous private bedrooms, the upstairs bedroom offers a flexible space that can easily serve as a dedicated home office, home gym, media room, or guest suite. This room comes with the significant advantage of both air-conditioned storage and a large walk-in attic, ensuring clutter-free living. Bathrooms feature clean lines, modern fixtures, and striking custom tilework. The dedicated laundry room is equally impressive, boasting extensive cabinetry, quartz counters, and an eye-catching patterned tile backsplash. The fully fenced backyard provides exceptional privacy for your personal resort. The stunning private pool and spa are surrounded by a spacious paver patio, complemented by a charming fire pit area, making this the ultimate space for both lavish entertaining and quiet relaxation. Crucially, this exceptional home is zoned for highly-rated schools offering excellent educational opportunities. The coveted location ensures you are only minutes from the vibrant, golf-cart-friendly atmosphere of Historic Downtown Winter Garden, with its acclaimed Farmers Market, Plant Street Market, unique boutiques, and fine dining. This is a rare opportunity to own a meticulously crafted, custom home in one of Winter Garden's most desirable and private communities--priced BELOW APPRAISED VALUE. Schedule your private showing today to experience this unparalleled lifestyle in Oakland Hills!

5 Beds ⋅ 3 Baths ⋅ Oakland Hills SubDv. ⋅ 34787 Zip Code

Discover the pinnacle of custom-built luxury in Winter Garden with this spectacular 5-bedroom, 3-bathroom Modern Farmhouse, crafted by the esteemed Justice & Wood Builders. This home is situated within Oakland Hills, a truly exclusive enclave of just 17 homesites, offering a private and peaceful lifestyle while remaining mere moments from the energy of Historic Downtown Winter Garden. Set on a rare and expansive 0.47-acre lot, the property is graced by the majestic, moss-draped canopy of towering old oak trees, creating an idyllic, tranquil setting from the moment you arrive. Step inside to an airy, open-concept living space where natural light floods the wide-plank wood floors. The heart of the home is defined by dramatic cathedral ceilings, beautifully accentuated by rich, exposed timber ceiling beams. The kitchen is a masterful fusion of high design and functionality—a space that moves beyond standard "gourmet." It features premium shaker cabinetry, a massive center island finished in a striking blue-gray hue for contrast, and luxurious quartz countertops. Chefs will appreciate the professional stainless steel appliances, the deep farmhouse sink, and the dedicated natural gas range for precision cooking. The home's thoughtfully designed layout provides versatile living areas for every need. The three-car garage offers not just ample storage and parking, but the convenience of an EV adapter in the third bay, ready for your electric vehicle. Escape to the generous private bedrooms, the upstairs bedroom offers a flexible space that can easily serve as a dedicated home office, home gym, media room, or guest suite. This room comes with the significant advantage of both air-conditioned storage and a large walk-in attic, ensuring clutter-free living. Bathrooms feature clean lines, modern fixtures, and striking custom tilework. The dedicated laundry room is equally impressive, boasting extensive cabinetry, quartz counters, and an eye-catching patterned tile backsplash. The fully fenced backyard provides exceptional privacy for your personal resort. The stunning private pool and spa are surrounded by a spacious paver patio, complemented by a charming fire pit area, making this the ultimate space for both lavish entertaining and quiet relaxation. Crucially, this exceptional home is zoned for highly-rated schools offering excellent educational opportunities. The coveted location ensures you are only minutes from the vibrant, golf-cart-friendly atmosphere of Historic Downtown Winter Garden, with its acclaimed Farmers Market, Plant Street Market, unique boutiques, and fine dining. This is a rare opportunity to own a meticulously crafted, custom home in one of Winter Garden's most desirable and private communities--priced BELOW APPRAISED VALUE. Schedule your private showing today to experience this unparalleled lifestyle in Oakland Hills!

15210 E Oakland Avenue, Winter Garden

$825,000

Welcome to your private oasis in the highly desirable Winter Garden, Florida – just 20 minutes from Orlando’s world-famous attractions! This beautifully updated home offers the perfect blend of modern comforts, low-maintenance luxury, and peaceful privacy with no rear neighbors and lush greenery backing the property. Step inside to find elegant tray ceilings, recessed lighting, a dedicated formal dining room, and a flexible extra room ideal for a home office. All bedrooms, loft, and upstairs hallway provide luxury premium laminate flooring. The kitchen shines with fresh granite countertops, brand-new microwave and dishwasher, and plenty of natural light. The primary suite is your personal retreat, featuring a massive walk-in closet, a spacious garden tub, and a large walk-in shower – pure relaxation awaits. Outside, the low maintenance saltwater pool (complete with a new heater) is fully surrounded by a bird cage enclosure for year-round enjoyment without the bugs. Relax on the covered porch sitting area while enjoying total privacy and beautiful greenery. Imagine evenings like this in your own backyard paradise: Additional highlights include: • Pavered driveway and charming courtyard entry in front • Classic tile roof, rain gutters, French drains, and a brand-new irrigation system • Two AC units (only 2 years old), full-house water softener, termite bond, and extra storage racks in the garage • Convenient pool bathroom, small loft area at the top of the stairs, and sidewalks with street lights throughout the neighborhood • All TVs, projector screen in primary bedroom, patio furniture, loungers, and fire pit stay with the purchase! This move-in-ready home sits in a highly rated school district and offers the Florida lifestyle you’ve been dreaming of – privacy, updates, and proximity to everything Central Florida has to offer. Don’t miss this rare opportunity – schedule your private showing today! Video link: https://www.youtube.com/watch?v=tIeVrqvqRHE

5 Beds ⋅ 4 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code

Welcome to your private oasis in the highly desirable Winter Garden, Florida – just 20 minutes from Orlando’s world-famous attractions! This beautifully updated home offers the perfect blend of modern comforts, low-maintenance luxury, and peaceful privacy with no rear neighbors and lush greenery backing the property. Step inside to find elegant tray ceilings, recessed lighting, a dedicated formal dining room, and a flexible extra room ideal for a home office. All bedrooms, loft, and upstairs hallway provide luxury premium laminate flooring. The kitchen shines with fresh granite countertops, brand-new microwave and dishwasher, and plenty of natural light. The primary suite is your personal retreat, featuring a massive walk-in closet, a spacious garden tub, and a large walk-in shower – pure relaxation awaits. Outside, the low maintenance saltwater pool (complete with a new heater) is fully surrounded by a bird cage enclosure for year-round enjoyment without the bugs. Relax on the covered porch sitting area while enjoying total privacy and beautiful greenery. Imagine evenings like this in your own backyard paradise: Additional highlights include: • Pavered driveway and charming courtyard entry in front • Classic tile roof, rain gutters, French drains, and a brand-new irrigation system • Two AC units (only 2 years old), full-house water softener, termite bond, and extra storage racks in the garage • Convenient pool bathroom, small loft area at the top of the stairs, and sidewalks with street lights throughout the neighborhood • All TVs, projector screen in primary bedroom, patio furniture, loungers, and fire pit stay with the purchase! This move-in-ready home sits in a highly rated school district and offers the Florida lifestyle you’ve been dreaming of – privacy, updates, and proximity to everything Central Florida has to offer. Don’t miss this rare opportunity – schedule your private showing today! Video link: https://www.youtube.com/watch?v=tIeVrqvqRHE

2145 Tillman Avenue, Winter Garden

$550,000

This stunning 5 BEDROOM + LOFT + DEN, 3.5 BATH home is situated on a spacious CONSERVATION LOT in the all-new Oakland Trail community. Once you step inside you will immediately appreciate the modern open first floor feat NEW VINYL PLANK flooring int the living room/ dining room. The spacious kitchen feat stainless steel appliance package, lots of cabinet storage under beautiful granite counters, and center island with breakfast bar. The family room and the rear lanai feat peaceful views of the rear lawn and conservation area. The first floor master suite feat a large walk in closet and the master bath complete with dual sinks, walk in shower, and garden tub. Upstairs you will find 4 additional bedrooms all with large closets, and served by 2 additional full baths. The flexibility of this home is endless as the upstairs features an additional LOFT SPACE as well as a 2nd Floor DEN. You get a large house without large energy bills as Meritage Homes is relentless with energy efficiency in their products. The Oakland Trails community centers around a generous park area and includes community pool, playground, and dog park! The community is located near the West Orange Trail, historic downtown Plant Street, and a short drive from Winter Garden Village. The location of this home can't be beat for ease of access to the Turnpike, shopping, and dining. Call today to see this home!

5 Beds ⋅ 4 Baths ⋅ Oakland Trls Ph 2 SubDv. ⋅ 34787 Zip Code

This stunning 5 BEDROOM + LOFT + DEN, 3.5 BATH home is situated on a spacious CONSERVATION LOT in the all-new Oakland Trail community. Once you step inside you will immediately appreciate the modern open first floor feat NEW VINYL PLANK flooring int the living room/ dining room. The spacious kitchen feat stainless steel appliance package, lots of cabinet storage under beautiful granite counters, and center island with breakfast bar. The family room and the rear lanai feat peaceful views of the rear lawn and conservation area. The first floor master suite feat a large walk in closet and the master bath complete with dual sinks, walk in shower, and garden tub. Upstairs you will find 4 additional bedrooms all with large closets, and served by 2 additional full baths. The flexibility of this home is endless as the upstairs features an additional LOFT SPACE as well as a 2nd Floor DEN. You get a large house without large energy bills as Meritage Homes is relentless with energy efficiency in their products. The Oakland Trails community centers around a generous park area and includes community pool, playground, and dog park! The community is located near the West Orange Trail, historic downtown Plant Street, and a short drive from Winter Garden Village. The location of this home can't be beat for ease of access to the Turnpike, shopping, and dining. Call today to see this home!

1490 Stone Arrow Court, Winter Garden

$755,000

This Winter Garden Solar home located in MCALLISTER LANDING is a stunning pool home with tons of upgrades. Gorgeous 5 bedroom and 3.5 baths, this home is perfect for families who want to enjoy a luxurious lifestyle without compromising on comfort. The home boasts a beautiful solar heated salt-water pool. Entertain family and friends at your private Tiki Bar by Paradise Grills with GS-32 Premium Grill*Stainless Refrigerator*Wine Refrigerator*Stainless Storage Door *Stainless Outlets*Stainless Bar Rail*TV for watching football games*Outdoor Marine Stereo with Speakers *Smart App Controlled LED Lighting with a value of $40,000. Stunning chef-style kitchen features large island for family gatherings, built-in oven, cook top, 42" cabinets, granite countertops, walk-in pantry and cafe overlooks pool. Large dining room*Private office*Large master suite is located on first floor and overlooks pool. Huge master bath includes soaking tub, separate shower, his and her vanities and huge walk-in closet. Large secondary bedrooms have walk-in closets. Upgrades include: plantation shutters throughout house, pool bath door added, fence, artificial turf in backyard, curbs around planters and luxury vinyl added to master bedroom, bedroom 5 and bonus room. Electricity bill's during the summer were $200 or less to cool this 3628 square foot home. Inside laundry room*Tons of storage*3 CAR Garage - Tandem. Large privacy fenced yard offers privacy. The community amenities include a lake side park, playground and dock by a serene conservation area for bird and animal watching on Lake Apopka. Historic downtown Winter Garden is just minutes away with the famous & best Farmers Market, West Orange Trail, shopping, restaurants, a brewery with Artisan kiosks, great community events and more. Hospitals, Churches, Schools and major highways: 408, 429 and the Turnpike are an easy short drive. Winter Garden is a fabulous place to be in Central Florida., and it's even in close proximity to the major theme parks throughout Central Florida! Ocoee High School has an "A" rating!

5 Beds ⋅ 4 Baths ⋅ Mcallister Lndg Ph 2 SubDv. ⋅ 34787 Zip Code

This Winter Garden Solar home located in MCALLISTER LANDING is a stunning pool home with tons of upgrades. Gorgeous 5 bedroom and 3.5 baths, this home is perfect for families who want to enjoy a luxurious lifestyle without compromising on comfort. The home boasts a beautiful solar heated salt-water pool. Entertain family and friends at your private Tiki Bar by Paradise Grills with GS-32 Premium Grill*Stainless Refrigerator*Wine Refrigerator*Stainless Storage Door *Stainless Outlets*Stainless Bar Rail*TV for watching football games*Outdoor Marine Stereo with Speakers *Smart App Controlled LED Lighting with a value of $40,000. Stunning chef-style kitchen features large island for family gatherings, built-in oven, cook top, 42" cabinets, granite countertops, walk-in pantry and cafe overlooks pool. Large dining room*Private office*Large master suite is located on first floor and overlooks pool. Huge master bath includes soaking tub, separate shower, his and her vanities and huge walk-in closet. Large secondary bedrooms have walk-in closets. Upgrades include: plantation shutters throughout house, pool bath door added, fence, artificial turf in backyard, curbs around planters and luxury vinyl added to master bedroom, bedroom 5 and bonus room. Electricity bill's during the summer were $200 or less to cool this 3628 square foot home. Inside laundry room*Tons of storage*3 CAR Garage - Tandem. Large privacy fenced yard offers privacy. The community amenities include a lake side park, playground and dock by a serene conservation area for bird and animal watching on Lake Apopka. Historic downtown Winter Garden is just minutes away with the famous & best Farmers Market, West Orange Trail, shopping, restaurants, a brewery with Artisan kiosks, great community events and more. Hospitals, Churches, Schools and major highways: 408, 429 and the Turnpike are an easy short drive. Winter Garden is a fabulous place to be in Central Florida., and it's even in close proximity to the major theme parks throughout Central Florida! Ocoee High School has an "A" rating!

665 Brooks Field Drive, Winter Garden

$2,075,000

Under contract-accepting backup offers. This is more than a house ~ Lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare “water-on-water” moment – breathtaking panoramic lake views that frame the entire living space and set the tone for everything that follows. Designed for effortless living and unforgettable entertaining, Come home and immediately dive into the lake life. Expansive sliding glass doors dissolve the line between indoors and out, opening to a resort-style backyard featuring a saltwater pool, heated spa, pool ledge loungers, integrated lighting, and a pool crawler cleaning system. Motorized lanai screens, a built-in outdoor kitchen with gas grill, and a gas fire pit creating the ultimate sunset and entertainment zone – complete with water views and space to gather - there or on your private dock! Inside, the chef’s kitchen anchors the home with an oversized island seating up to eight, custom wood vent hood, gas cooktop, designer finishes, barn door accents, and thoughtful upgrades throughout. Custom wood beams add warmth and architectural interest, while the open layout flows seamlessly to living, dining, and outdoor spaces – ideal for hosting or relaxing in style. Luxury meets intelligence with over $30,000 in smart home upgrades, including full Alarm automation, indoor and outdoor security cameras, remote access controls, Sonos audio, and Bluetooth sound zones throughout the kitchen, living room, loft, lanai, and balcony. Motorized shades on both floors provide privacy and convenience at the touch of a button. A reverse osmosis water system enhances everyday living, and the first-floor laundry adds to the home’s thoughtful functionality. Both primary suites are beautiful, a spa-inspired primary bath, and a custom walk-in closet. A dedicated gaming room offers a turnkey entertainment space – perfect for family & friends fun for all ages. Step onto the front-facing balcony in the evenings and enjoy nightly Disney fireworks, a magical reminder of how close you are to it all. The epoxy-finished three-car garage includes an additional storage bay, offering space for vehicles, toys, and lake-life essentials. Outside, low-maintenance AstroTurf landscaping keeps the focus on enjoyment, not upkeep. Just minutes from Disney theme parks, shopping, dining, and with easy access to SR-429, this home is approximately 30–40 minutes from Orlando International Airport, making it ideal as a primary residence, second home, or luxury retreat. Comfortable, elevated, and completely move-in ready – this is lakefront living done right! Call today to schedule your tour and let us welcome you home!

5 Beds ⋅ 5 Baths ⋅ Avalon Cove SubDv. ⋅ 34787 Zip Code

Under contract-accepting backup offers. This is more than a house ~ Lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare “water-on-water” moment – breathtaking panoramic lake views that frame the entire living space and set the tone for everything that follows. Designed for effortless living and unforgettable entertaining, Come home and immediately dive into the lake life. Expansive sliding glass doors dissolve the line between indoors and out, opening to a resort-style backyard featuring a saltwater pool, heated spa, pool ledge loungers, integrated lighting, and a pool crawler cleaning system. Motorized lanai screens, a built-in outdoor kitchen with gas grill, and a gas fire pit creating the ultimate sunset and entertainment zone – complete with water views and space to gather - there or on your private dock! Inside, the chef’s kitchen anchors the home with an oversized island seating up to eight, custom wood vent hood, gas cooktop, designer finishes, barn door accents, and thoughtful upgrades throughout. Custom wood beams add warmth and architectural interest, while the open layout flows seamlessly to living, dining, and outdoor spaces – ideal for hosting or relaxing in style. Luxury meets intelligence with over $30,000 in smart home upgrades, including full Alarm automation, indoor and outdoor security cameras, remote access controls, Sonos audio, and Bluetooth sound zones throughout the kitchen, living room, loft, lanai, and balcony. Motorized shades on both floors provide privacy and convenience at the touch of a button. A reverse osmosis water system enhances everyday living, and the first-floor laundry adds to the home’s thoughtful functionality. Both primary suites are beautiful, a spa-inspired primary bath, and a custom walk-in closet. A dedicated gaming room offers a turnkey entertainment space – perfect for family & friends fun for all ages. Step onto the front-facing balcony in the evenings and enjoy nightly Disney fireworks, a magical reminder of how close you are to it all. The epoxy-finished three-car garage includes an additional storage bay, offering space for vehicles, toys, and lake-life essentials. Outside, low-maintenance AstroTurf landscaping keeps the focus on enjoyment, not upkeep. Just minutes from Disney theme parks, shopping, dining, and with easy access to SR-429, this home is approximately 30–40 minutes from Orlando International Airport, making it ideal as a primary residence, second home, or luxury retreat. Comfortable, elevated, and completely move-in ready – this is lakefront living done right! Call today to schedule your tour and let us welcome you home!

9014 Morgana Court, Winter Garden

$1,350,000

The Sanibel model: a champion among estates. To own this residence is to inherit a legacy. Known locally as The Castle, this 4,713-square-foot Mediterranean masterpiece is not merely a home, it is a decorated champion. Having secured the SEBC Excel Award for Best Model in Florida and the Parade of Homes Award, this estate stands as a testament to architectural perfection. It offers a rare opportunity to acquire a pedigree property that balances status of a trophy home with intimate sanctuary of a primary residence. Grandeur at the threshold: The arrival experience is nothing short of cinematic. Framed by a classic Terra Cotta barrel tile roof and sweeping front balconies, the façade commands immediate respect. As you push open the imposing 8-foot arched wood double doors, the world behind you fades. You are greeted by a breathtaking foyer where an elegant wood staircase, adorned with custom decorative iron railings, spirals upward. Your gaze is instantly drawn through the home, past the volume ceilings and sun-drenched corridors, directly to the shimmering fountains and pool, establishing a seamless visual connection with the outdoors. Unrivaled entertaining: Designed for the host who refuses to compromise, the main level is a triumph of open-concept design. Whether hosting a grand gala or an intimate wine tasting, the flow is effortless. The culinary center, featuring natural gas cooking, anchors the great room, allowing conversations to drift naturally through 8-foot interior doors onto the expansive lanai. This is the epitome of Florida’s indoor-outdoor lifestyle, sophisticated, airy and undeniably impressive. With four bedrooms, each boasting private en-suite baths, every guest is treated to comfort of a five-star hotel. The crown jewel, the owner’s suite: The pièce de résistance, however, awaits upstairs. The owner's suite is not just a bedroom, it is an architectural event. Entry is granted through a jaw-dropping rotunda, a dramatic vestibule that signals you are entering a private realm of luxury. Under soaring ceilings, the suite expands into a sanctuary of solitude, complete with private balcony access that invites the morning breeze. It is a retreat worthy of the estate’s royal moniker. Experience the award-winning lifestyle of The Castle.

4 Beds ⋅ 5 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code

The Sanibel model: a champion among estates. To own this residence is to inherit a legacy. Known locally as The Castle, this 4,713-square-foot Mediterranean masterpiece is not merely a home, it is a decorated champion. Having secured the SEBC Excel Award for Best Model in Florida and the Parade of Homes Award, this estate stands as a testament to architectural perfection. It offers a rare opportunity to acquire a pedigree property that balances status of a trophy home with intimate sanctuary of a primary residence. Grandeur at the threshold: The arrival experience is nothing short of cinematic. Framed by a classic Terra Cotta barrel tile roof and sweeping front balconies, the façade commands immediate respect. As you push open the imposing 8-foot arched wood double doors, the world behind you fades. You are greeted by a breathtaking foyer where an elegant wood staircase, adorned with custom decorative iron railings, spirals upward. Your gaze is instantly drawn through the home, past the volume ceilings and sun-drenched corridors, directly to the shimmering fountains and pool, establishing a seamless visual connection with the outdoors. Unrivaled entertaining: Designed for the host who refuses to compromise, the main level is a triumph of open-concept design. Whether hosting a grand gala or an intimate wine tasting, the flow is effortless. The culinary center, featuring natural gas cooking, anchors the great room, allowing conversations to drift naturally through 8-foot interior doors onto the expansive lanai. This is the epitome of Florida’s indoor-outdoor lifestyle, sophisticated, airy and undeniably impressive. With four bedrooms, each boasting private en-suite baths, every guest is treated to comfort of a five-star hotel. The crown jewel, the owner’s suite: The pièce de résistance, however, awaits upstairs. The owner's suite is not just a bedroom, it is an architectural event. Entry is granted through a jaw-dropping rotunda, a dramatic vestibule that signals you are entering a private realm of luxury. Under soaring ceilings, the suite expands into a sanctuary of solitude, complete with private balcony access that invites the morning breeze. It is a retreat worthy of the estate’s royal moniker. Experience the award-winning lifestyle of The Castle.

606 Canopy Estates Drive, Winter Garden

$880,000

Discover Florida living at 2320 Wintermere Pointe in Winter Garden, FL - a stunningly updated pool home with breathtaking pond views in a gated community that blends privacy, lifestyle, and convenience near Winter Garden Village, AdventHealth Winter Garden, Disney, Windermere, Orlando, SR 429, and the Florida Turnpike. From the moment you enter, high ceilings, natural light, and an open floor plan create a sense of space and connection. A dedicated office at the front of the home makes working, studying, or running a business from home simple and comfortable. The heart of the house is the recently renovated kitchen - a true chef’s dream with white shaker cabinets, quartz countertops, upgraded hardware, stainless steel appliances, and clear views overlooking the pool and pond. Step outside to the screened lanai, large paver patio, and oversized pool, where peaceful pond and sunset views create the perfect setting for relaxing or entertaining. The split floor plan offers wonderful functionality for multi-generational living or visiting guests, providing comfort and privacy on both sides of the home. The main-floor primary suite feels like a resort retreat with sliders to the lanai, dual vanities plus a makeup vanity, frameless glass shower tiled to the ceiling, refreshed finishes, and double walk-in closets. Upstairs, the spacious bonus room offers unlimited opportunity - ideal for a playroom, game room, home gym, media room, or additional guest space. Inside, updated flooring and fresh interior paint add to the bright, move-in-ready feel. Wintermere Pointe is an established gated community with mature landscaping, beautiful ponds, tennis courts, and playground - all with a low HOA. With the roof replaced in 2020, both AC units replaced in 2023, and the water heater in 2025, major systems are already updated and the home is move in ready. If you’re searching for a beautifully updated Winter Garden home for sale with pond views, a private pool, and easy access to everything Orlando and Central Florida have to offer, this home delivers comfort, convenience, and everyday elegance. Schedule your private tour today.

5 Beds ⋅ 3 Baths ⋅ Wintermere Pointe Ph 02 46/141 SubDv. ⋅ 34787 Zip Code

Discover Florida living at 2320 Wintermere Pointe in Winter Garden, FL - a stunningly updated pool home with breathtaking pond views in a gated community that blends privacy, lifestyle, and convenience near Winter Garden Village, AdventHealth Winter Garden, Disney, Windermere, Orlando, SR 429, and the Florida Turnpike. From the moment you enter, high ceilings, natural light, and an open floor plan create a sense of space and connection. A dedicated office at the front of the home makes working, studying, or running a business from home simple and comfortable. The heart of the house is the recently renovated kitchen - a true chef’s dream with white shaker cabinets, quartz countertops, upgraded hardware, stainless steel appliances, and clear views overlooking the pool and pond. Step outside to the screened lanai, large paver patio, and oversized pool, where peaceful pond and sunset views create the perfect setting for relaxing or entertaining. The split floor plan offers wonderful functionality for multi-generational living or visiting guests, providing comfort and privacy on both sides of the home. The main-floor primary suite feels like a resort retreat with sliders to the lanai, dual vanities plus a makeup vanity, frameless glass shower tiled to the ceiling, refreshed finishes, and double walk-in closets. Upstairs, the spacious bonus room offers unlimited opportunity - ideal for a playroom, game room, home gym, media room, or additional guest space. Inside, updated flooring and fresh interior paint add to the bright, move-in-ready feel. Wintermere Pointe is an established gated community with mature landscaping, beautiful ponds, tennis courts, and playground - all with a low HOA. With the roof replaced in 2020, both AC units replaced in 2023, and the water heater in 2025, major systems are already updated and the home is move in ready. If you’re searching for a beautifully updated Winter Garden home for sale with pond views, a private pool, and easy access to everything Orlando and Central Florida have to offer, this home delivers comfort, convenience, and everyday elegance. Schedule your private tour today.

2320 Wintermere Pointe Drive, Winter Garden

$1,500,000

Welcome to this exceptional RCB custom home with a pool located in the highly desirable Oakland Park community. Ideally positioned directly across from a green area and surrounded by walking trails on both sides, this home offers park and lake views from the front porch and an upstairs bedroom, creating a peaceful and picturesque setting. The residence features 6 bedrooms and 5 full bathrooms, with two bedrooms located on the first floor. One is a full guest suite with walk-in closet, while the second first-floor bedroom—currently used as a home office with elegant glass French doors excellent flexibility work-from-home needs. Designed for both everyday living and entertaining, the home showcases an outstanding kitchen overlooking the main living area, complemented by a large walk-in pantry, enhanced by a hidden oversized pantry/bar area with microwave and mini beverage refrigerator. Outdoor living is a highlight, featuring a resort-style pool and spa, covered patio, and retractable screen, ideal for year-round enjoyment. The home also offers a rare three-and-a-half car oversized garage, including a dedicated roll-up garage door with direct access to the pool area, plus a large built-out storage attic with staircase access. Additional features and upgrades include LVP flooring, wood beams, electric fireplace, crown molding, metal roof over the front porch, CAT 6 wiring throughout, whole-house water softener, whole-house surge protector, and a home that has been consistently maintained under an air-conditioning service plan. Located just three blocks from the West Orange Trail and within a golf-cart-approved community, the property is within walking distance to Tildenville Elementary School (9/10 rating) with magnet and global language programs, as well as Oakland Charter School and the local middle school. Just minutes from downtown Winter Garden, this home offers exceptional access to dining, shopping, and outdoor recreation. This thoughtfully designed residence combines quality craftsmanship, flexibility, and an outstanding location—offering refined Florida living in one of Oakland’s most desirable communities.

6 Beds ⋅ 5 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code

Welcome to this exceptional RCB custom home with a pool located in the highly desirable Oakland Park community. Ideally positioned directly across from a green area and surrounded by walking trails on both sides, this home offers park and lake views from the front porch and an upstairs bedroom, creating a peaceful and picturesque setting. The residence features 6 bedrooms and 5 full bathrooms, with two bedrooms located on the first floor. One is a full guest suite with walk-in closet, while the second first-floor bedroom—currently used as a home office with elegant glass French doors excellent flexibility work-from-home needs. Designed for both everyday living and entertaining, the home showcases an outstanding kitchen overlooking the main living area, complemented by a large walk-in pantry, enhanced by a hidden oversized pantry/bar area with microwave and mini beverage refrigerator. Outdoor living is a highlight, featuring a resort-style pool and spa, covered patio, and retractable screen, ideal for year-round enjoyment. The home also offers a rare three-and-a-half car oversized garage, including a dedicated roll-up garage door with direct access to the pool area, plus a large built-out storage attic with staircase access. Additional features and upgrades include LVP flooring, wood beams, electric fireplace, crown molding, metal roof over the front porch, CAT 6 wiring throughout, whole-house water softener, whole-house surge protector, and a home that has been consistently maintained under an air-conditioning service plan. Located just three blocks from the West Orange Trail and within a golf-cart-approved community, the property is within walking distance to Tildenville Elementary School (9/10 rating) with magnet and global language programs, as well as Oakland Charter School and the local middle school. Just minutes from downtown Winter Garden, this home offers exceptional access to dining, shopping, and outdoor recreation. This thoughtfully designed residence combines quality craftsmanship, flexibility, and an outstanding location—offering refined Florida living in one of Oakland’s most desirable communities.

1008 Tilden Oaks Trail, Oakland

$700,000

This stunning 4-bedroom, 3.5-bath home sits on a corner lot in the highly sought-after Orchard Hills community. Perfectly positioned just minutes from Magic Kingdom, Hamlin Town Center, the new Horizon West Regional Park, and Horizon West Library, the location truly can’t be beat. Designed with both functionality and entertaining in mind, the home features a three-car tandem garage, a spacious loft, a formal dining room, and a dedicated first-floor office. The open-concept layout flows seamlessly from the living and dining areas into the upgraded kitchen; ideal for everyday living and hosting guests. The kitchen is equipped with a reverse osmosis system, and the home also includes a whole-house water softening system. Recent updates elevate the space, including fresh interior paint (2025), new bamboo flooring on the stairs and throughout the second floor, stylish accent walls, and upgraded modern handrails. Upstairs, all four bedrooms are thoughtfully arranged alongside a generous loft. The primary suite is a true retreat, offering an expansive layout and dual closets for ample storage. Step outside to a screened-in backyard designed for relaxation and entertaining, complete with a fire pit, private putting green, and custom screen lighting that sets the perfect evening ambiance. Orchard Hills offers a vibrant sense of community with a clubhouse, fitness center, community pool, dog park, playground, year-round community events, and HOA-maintained landscaping. With modern updates, an exceptional outdoor entertaining space, and a prime location, this home delivers comfort, style, and community. Step inside and feel instantly at home—schedule your private tour today.

4 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 3 SubDv. ⋅ 34787 Zip Code

This stunning 4-bedroom, 3.5-bath home sits on a corner lot in the highly sought-after Orchard Hills community. Perfectly positioned just minutes from Magic Kingdom, Hamlin Town Center, the new Horizon West Regional Park, and Horizon West Library, the location truly can’t be beat. Designed with both functionality and entertaining in mind, the home features a three-car tandem garage, a spacious loft, a formal dining room, and a dedicated first-floor office. The open-concept layout flows seamlessly from the living and dining areas into the upgraded kitchen; ideal for everyday living and hosting guests. The kitchen is equipped with a reverse osmosis system, and the home also includes a whole-house water softening system. Recent updates elevate the space, including fresh interior paint (2025), new bamboo flooring on the stairs and throughout the second floor, stylish accent walls, and upgraded modern handrails. Upstairs, all four bedrooms are thoughtfully arranged alongside a generous loft. The primary suite is a true retreat, offering an expansive layout and dual closets for ample storage. Step outside to a screened-in backyard designed for relaxation and entertaining, complete with a fire pit, private putting green, and custom screen lighting that sets the perfect evening ambiance. Orchard Hills offers a vibrant sense of community with a clubhouse, fitness center, community pool, dog park, playground, year-round community events, and HOA-maintained landscaping. With modern updates, an exceptional outdoor entertaining space, and a prime location, this home delivers comfort, style, and community. Step inside and feel instantly at home—schedule your private tour today.

14588 Magnolia Ridge Loop, Winter Garden

$870,000

PRICED TO SELL! Welcome home to this stunning two-story residence in the gated community of Tilden Place, ideally located in the heart of Winter Garden. Just minutes from Winter Garden Village with its abundant shopping, dining, fast-casual options, hospital access, and everyday conveniences—and only a short drive to Walt Disney World Resort, this home offers the perfect blend of luxury, comfort, and location. Built by MI Homes, known for exceptional energy efficiency, this 5-bedroom, 4-bath home showcases sleek, modern upgrades throughout. The pavered driveway and porch set the tone, opening to a thoughtfully designed floor plan that includes a first-floor bedroom with a full bathroom, ideal for guests, multigenerational living, or a private home office. The main living areas feature LVP flooring, striking iron stair railings, and incredible custom trim work along the staircase. The gourmet kitchen will keep even the pickiest of chefs happy, featuring dark cabinetry that beautifully contrasts with a bright white waterfall island, pendant lighting, stainless steel appliances, gas cooking, and stunning upper cabinetry that elevates the space. A built-in pocket office offers the perfect spot for quick correspondence, bill pay, remote work, or a homework station. The family room is anchored by a dramatic wall of custom built-in shelving with accent lighting and a fireplace, creating a warm and inviting focal point for everyday living and entertaining. Upstairs, a spacious loft continues the custom design theme with floating shelves and integrated storage. The expansive upstairs primary suite features LVP flooring, generous space, and access to a private balcony, perfect for morning coffee or evening relaxation. With no rear neighbors, enjoy a private backyard retreat complete with an extended lanai, while the coastal-style balcony off the loft provides even more opportunities for entertaining and unwinding. The intimate gated community is centered around a beautiful pond with a fountain, and just a short walk down the street brings you to the community green space and playground. This stunning home truly offers modern luxury, functional living, privacy, and an unbeatable Winter Garden location. WELCOME HOME!

5 Beds ⋅ 4 Baths ⋅ Tilden Place/Winter Garden SubDv. ⋅ 34787 Zip Code

PRICED TO SELL! Welcome home to this stunning two-story residence in the gated community of Tilden Place, ideally located in the heart of Winter Garden. Just minutes from Winter Garden Village with its abundant shopping, dining, fast-casual options, hospital access, and everyday conveniences—and only a short drive to Walt Disney World Resort, this home offers the perfect blend of luxury, comfort, and location. Built by MI Homes, known for exceptional energy efficiency, this 5-bedroom, 4-bath home showcases sleek, modern upgrades throughout. The pavered driveway and porch set the tone, opening to a thoughtfully designed floor plan that includes a first-floor bedroom with a full bathroom, ideal for guests, multigenerational living, or a private home office. The main living areas feature LVP flooring, striking iron stair railings, and incredible custom trim work along the staircase. The gourmet kitchen will keep even the pickiest of chefs happy, featuring dark cabinetry that beautifully contrasts with a bright white waterfall island, pendant lighting, stainless steel appliances, gas cooking, and stunning upper cabinetry that elevates the space. A built-in pocket office offers the perfect spot for quick correspondence, bill pay, remote work, or a homework station. The family room is anchored by a dramatic wall of custom built-in shelving with accent lighting and a fireplace, creating a warm and inviting focal point for everyday living and entertaining. Upstairs, a spacious loft continues the custom design theme with floating shelves and integrated storage. The expansive upstairs primary suite features LVP flooring, generous space, and access to a private balcony, perfect for morning coffee or evening relaxation. With no rear neighbors, enjoy a private backyard retreat complete with an extended lanai, while the coastal-style balcony off the loft provides even more opportunities for entertaining and unwinding. The intimate gated community is centered around a beautiful pond with a fountain, and just a short walk down the street brings you to the community green space and playground. This stunning home truly offers modern luxury, functional living, privacy, and an unbeatable Winter Garden location. WELCOME HOME!

14423 Wabasso Loop, Winter Garden

$900,000

Six bedrooms PLUS an office, PLUS a media room, PLUS a pool, PLUS a fully fenced yard, PLUS fully paid off solar panels, and PLUS a three-car garage. This home truly has it all. From the moment you enter, you will appreciate the flexible and functional floor plan featuring a formal living room and formal dining room, ideal for entertaining. The spacious kitchen is the heart of the home and offers a center island, breakfast bar, dinette area, and open flow into the family room. The first floor includes a private office PLUS a guest bedroom and a full bathroom. Triple sliding glass doors open to the screened back patio, where you will find a covered seating and dining area and a sparkling pool, all within the screened enclosure. The private, fully fenced backyard surrounds the outdoor space and features multiple fruit trees along with room to relax or play. Upstairs is the true family hub, featuring the primary suite PLUS four additional bedrooms, a loft area, and a dedicated media or theater room. A large balcony, accessible from both the primary suite and the media room, provides an additional outdoor retreat. Additional highlights include fully paid off solar panels for impressive energy savings PLUS maintenance-free lawn care included in the HOA dues. This exceptional home offers space, function, and value. Schedule your private showing today.

6 Beds ⋅ 4 Baths ⋅ Alexander Ridge SubDv. ⋅ 34787 Zip Code

Six bedrooms PLUS an office, PLUS a media room, PLUS a pool, PLUS a fully fenced yard, PLUS fully paid off solar panels, and PLUS a three-car garage. This home truly has it all. From the moment you enter, you will appreciate the flexible and functional floor plan featuring a formal living room and formal dining room, ideal for entertaining. The spacious kitchen is the heart of the home and offers a center island, breakfast bar, dinette area, and open flow into the family room. The first floor includes a private office PLUS a guest bedroom and a full bathroom. Triple sliding glass doors open to the screened back patio, where you will find a covered seating and dining area and a sparkling pool, all within the screened enclosure. The private, fully fenced backyard surrounds the outdoor space and features multiple fruit trees along with room to relax or play. Upstairs is the true family hub, featuring the primary suite PLUS four additional bedrooms, a loft area, and a dedicated media or theater room. A large balcony, accessible from both the primary suite and the media room, provides an additional outdoor retreat. Additional highlights include fully paid off solar panels for impressive energy savings PLUS maintenance-free lawn care included in the HOA dues. This exceptional home offers space, function, and value. Schedule your private showing today.

2069 Nerva Road, Winter Garden

$979,520

Welcome to this beautifully built home located in a desirable Winter Garden community. This property offers a functional floor plan with spacious living areas and plenty of natural light. The kitchen features ample cabinetry and counter space and opens to the main living area, making it ideal for everyday living. The primary bedroom includes an en-suite bath, with additional bedrooms suitable for family, guests, or a home office. Enjoy outdoor space perfect for relaxing or entertaining. Conveniently located near downtown Winter Garden, the West Orange Trail, shopping, dining, and major roadways for an easy commute. A great opportunity to own in a sought-after area.

5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully built home located in a desirable Winter Garden community. This property offers a functional floor plan with spacious living areas and plenty of natural light. The kitchen features ample cabinetry and counter space and opens to the main living area, making it ideal for everyday living. The primary bedroom includes an en-suite bath, with additional bedrooms suitable for family, guests, or a home office. Enjoy outdoor space perfect for relaxing or entertaining. Conveniently located near downtown Winter Garden, the West Orange Trail, shopping, dining, and major roadways for an easy commute. A great opportunity to own in a sought-after area.

350 Crystal Wood Drive, Winter Garden

$1,585,480

MI HOMES NEW CONSTRUCTION | NEWPORT XL FLOORPLAN

5 Beds ⋅ 4 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code

MI HOMES NEW CONSTRUCTION | NEWPORT XL FLOORPLAN

17378 Glossy Pomelo, Winter Garden

$650,000

One or more photo(s) has been virtually staged. Stunning and spacious Winter Garden home offering over 3,000 square feet of thoughtfully designed living space. This 5-bedroom, 4-bath residence features a gourmet kitchen complete with double ovens, quartz countertops, stainless steel appliances, and a large center island—perfect for entertaining. A formal dining room and expansive great room create an inviting atmosphere for gatherings and everyday living. The first floor includes secondary bedroom along with full bath and showcases luxury vinyl flooring throughout, along with designer wainscoting in the foyer and primary bedroom. Upstairs offers a split floor plan with additional bedrooms, Jack & Jill bath, and a versatile bonus room, ideal for a home office, media room, or play space. The luxurious primary suite is a true retreat, featuring a walk-in closet with custom built-ins, double sink vanity, a garden tub, separate shower, and private water closet. Enjoy outdoor living on the extended screened lanai overlooking the fenced yard. Plenty of room for a pool!! Additional highlights include excellent storage throughout, two hot water tanks, and a 3-car garage with air conditioning. This exceptional home combines elegance, comfort, and functionality—perfect for modern living. Located just a few minutes from the shops, restaurants and entertainment in Historic Downtown Winter Garden, McAllister Landing offers lakeside living. This home is better than new!!!

5 Beds ⋅ 4 Baths ⋅ Mcallister Lndg SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Stunning and spacious Winter Garden home offering over 3,000 square feet of thoughtfully designed living space. This 5-bedroom, 4-bath residence features a gourmet kitchen complete with double ovens, quartz countertops, stainless steel appliances, and a large center island—perfect for entertaining. A formal dining room and expansive great room create an inviting atmosphere for gatherings and everyday living. The first floor includes secondary bedroom along with full bath and showcases luxury vinyl flooring throughout, along with designer wainscoting in the foyer and primary bedroom. Upstairs offers a split floor plan with additional bedrooms, Jack & Jill bath, and a versatile bonus room, ideal for a home office, media room, or play space. The luxurious primary suite is a true retreat, featuring a walk-in closet with custom built-ins, double sink vanity, a garden tub, separate shower, and private water closet. Enjoy outdoor living on the extended screened lanai overlooking the fenced yard. Plenty of room for a pool!! Additional highlights include excellent storage throughout, two hot water tanks, and a 3-car garage with air conditioning. This exceptional home combines elegance, comfort, and functionality—perfect for modern living. Located just a few minutes from the shops, restaurants and entertainment in Historic Downtown Winter Garden, McAllister Landing offers lakeside living. This home is better than new!!!

1474 Juniper Hammock Street, Winter Garden

$741,000

One or more photo(s) has been virtually staged. Welcome home to a lifestyle of space, comfort, and effortless entertaining in this beautifully designed two-story residence with charming exterior stone accents, set on an almost ¼-acre lot in a gated community. From the moment you step inside, you’ll appreciate the open, airy layout, high ceilings, and bamboo flooring throughout — no carpet anywhere for a clean, modern feel. At the heart of the home, the gourmet kitchen shines with stainless steel appliances and a stylish tile backsplash, perfectly positioned to flow into the main living areas for gatherings both big and small. Step outside to the huge screened lanai and screened-in porch, ideal for morning coffee, weekend barbecues, or relaxing evenings enjoying the Florida breeze. The primary suite on the main level offers a true retreat, featuring dual walk-in closets that connect directly to a spa-inspired bathroom with split vanities, a center garden tub, and an extra-long walk-in shower with dual shower heads. A dedicated office or den on the first floor makes working from home easy, while a convenient guest half bath, laundry room, and generous storage add everyday practicality. Upstairs, three additional bedrooms with ceiling fans provide comfortable private spaces, while the expansive game room creates the perfect hub for movie nights, playtime, or hosting friends. A 3-car garage completes the package, offering room for vehicles, hobbies, and storage. Designed for both everyday living and memorable entertaining, this home delivers the space, flexibility, and lifestyle today’s buyers are looking for — indoors and out.

4 Beds ⋅ 5 Baths ⋅ Reserve At Carriage Pointe SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Welcome home to a lifestyle of space, comfort, and effortless entertaining in this beautifully designed two-story residence with charming exterior stone accents, set on an almost ¼-acre lot in a gated community. From the moment you step inside, you’ll appreciate the open, airy layout, high ceilings, and bamboo flooring throughout — no carpet anywhere for a clean, modern feel. At the heart of the home, the gourmet kitchen shines with stainless steel appliances and a stylish tile backsplash, perfectly positioned to flow into the main living areas for gatherings both big and small. Step outside to the huge screened lanai and screened-in porch, ideal for morning coffee, weekend barbecues, or relaxing evenings enjoying the Florida breeze. The primary suite on the main level offers a true retreat, featuring dual walk-in closets that connect directly to a spa-inspired bathroom with split vanities, a center garden tub, and an extra-long walk-in shower with dual shower heads. A dedicated office or den on the first floor makes working from home easy, while a convenient guest half bath, laundry room, and generous storage add everyday practicality. Upstairs, three additional bedrooms with ceiling fans provide comfortable private spaces, while the expansive game room creates the perfect hub for movie nights, playtime, or hosting friends. A 3-car garage completes the package, offering room for vehicles, hobbies, and storage. Designed for both everyday living and memorable entertaining, this home delivers the space, flexibility, and lifestyle today’s buyers are looking for — indoors and out.

2015 Sandy Garden Lane, Winter Garden

$2,299,990

Sold Data entry only.

5 Beds ⋅ 4 Baths ⋅ Lake Star At Ovation - Phase 1a SubDv. ⋅ 34787 Zip Code

Sold Data entry only.

Winter Garden

$1,005,000

Waterfront Elegance in Winter Garden’s Golf Cart District Discover a rare opportunity to own a waterfront home in one of Downtown Winter Garden’s most desirable gated communities, nestled within the highly sought-after golf cart district. This beautifully appointed residence offers a seamless blend of luxury, comfort, and natural serenity. The oversized three-car garage provides ample space for vehicles, storage, and hobbies, while generous closet space throughout the home ensures convenience and organization. A whole-house water softener and purifier system, including an under-sink purifier, delivers pristine water quality for everyday living. Inside, the home is flooded with natural light, creating a warm and inviting atmosphere in every room. The home includes an upgraded electrical package including recessed lighting, multi-room switching, and multiple Ethernet/Coax jacks in every room. The gourmet kitchen is thoughtfully designed with a double sink, an island prep sink, a pasta arm faucet, upgraded cabinetry with soft-close hardware, and a spacious island that adds both functionality and extra storage. Step outside to your recently resurfaced covered boat dock with lift, lights/fan and sink; perfect for enjoying one of Florida’s largest lakes, the spring fed headwater of the Harris lake chain, extending to the St. John’s River and the Atlantic Ocean. The expansive backyard is home to prolific fruit trees bearing mango, avocado, star fruit, and citrus, creating a lush and edible landscape. Nature lovers will be captivated by the presence of over 300 bird species, including graceful blue herons and great white egrets, which frequent the property year-round. Breathtaking sunrises and sunsets can be enjoyed from the living room, patio, dock, or any of the three northern-facing bedrooms. Whether you're entertaining guests or enjoying a quiet evening at home, this property offers a lifestyle defined by tranquility, beauty, and waterfront charm. Experience refined waterfront living in the heart of Winter Garden’s iconic golf cart district, where luxury, charm, and everyday convenience meet.

4 Beds ⋅ 3 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code

Waterfront Elegance in Winter Garden’s Golf Cart District Discover a rare opportunity to own a waterfront home in one of Downtown Winter Garden’s most desirable gated communities, nestled within the highly sought-after golf cart district. This beautifully appointed residence offers a seamless blend of luxury, comfort, and natural serenity. The oversized three-car garage provides ample space for vehicles, storage, and hobbies, while generous closet space throughout the home ensures convenience and organization. A whole-house water softener and purifier system, including an under-sink purifier, delivers pristine water quality for everyday living. Inside, the home is flooded with natural light, creating a warm and inviting atmosphere in every room. The home includes an upgraded electrical package including recessed lighting, multi-room switching, and multiple Ethernet/Coax jacks in every room. The gourmet kitchen is thoughtfully designed with a double sink, an island prep sink, a pasta arm faucet, upgraded cabinetry with soft-close hardware, and a spacious island that adds both functionality and extra storage. Step outside to your recently resurfaced covered boat dock with lift, lights/fan and sink; perfect for enjoying one of Florida’s largest lakes, the spring fed headwater of the Harris lake chain, extending to the St. John’s River and the Atlantic Ocean. The expansive backyard is home to prolific fruit trees bearing mango, avocado, star fruit, and citrus, creating a lush and edible landscape. Nature lovers will be captivated by the presence of over 300 bird species, including graceful blue herons and great white egrets, which frequent the property year-round. Breathtaking sunrises and sunsets can be enjoyed from the living room, patio, dock, or any of the three northern-facing bedrooms. Whether you're entertaining guests or enjoying a quiet evening at home, this property offers a lifestyle defined by tranquility, beauty, and waterfront charm. Experience refined waterfront living in the heart of Winter Garden’s iconic golf cart district, where luxury, charm, and everyday convenience meet.

243 Zachary Wade Street, Winter Garden

$1,850,000

One or more photo(s) has been virtually staged. Get behind the gate of the highly sought-after Waterside community in Winter Garden. This extraordinary waterfront estate offers a rare blend of refined luxury, thoughtful design, and true lakefront living on Johns Lake. Built just six years ago and meticulously enhanced, this five-bedroom residence is primarily single-story, with the added flexibility of a private upstairs retreat featuring a spacious loft, full bedroom, and bathroom—ideal for guests, multi-generational living, or a quiet home office escape. From the moment you enter, the home makes a statement. Real, solid wood flooring flows throughout, adding warmth and authenticity that cannot be replicated with engineered alternatives. The expansive living areas were extended to create an open and inviting layout, perfectly suited for both everyday comfort and grand-scale entertaining. Dramatic waterfall-edge countertops anchor the kitchen and gathering spaces, blending modern elegance with timeless craftsmanship. The heart of the home extends seamlessly outdoors. An expansive, screened-in lanai overlooks the water, creating a true indoor-outdoor lifestyle. The electric, automatic screening system allows you to adjust the space effortlessly, making it enjoyable year-round. The outdoor kitchen is exceptional, designed for serious cooking and entertaining. It includes a Coyote gas grill, a Recteq pellet grill, a power burner, two outdoor refrigerators, a full-size sink, and a dedicated television—everything needed to host unforgettable evenings with friends and family. Beyond the lanai, the backyard opens to a large, fenced lawn that gently leads to your private dock on Johns Lake. The dock is fully equipped with a boat lift, as well as water and electricity, making lake access effortless and spontaneous. Whether you enjoy boating, fishing, or sunset cruises, this setting delivers the ultimate waterfront lifestyle. The saltwater infinity-edge pool is a showpiece, stretching an impressive 50 feet and designed to visually merge with the lake beyond. Heated by gas, the pool is ideal for both leisurely afternoons and evening swims, offering breathtaking views and a true resort-style experience in your own backyard. Inside, the home continues to impress with high-end features that elevate daily living. A tankless water heater ensures endless hot water, while a central vacuum system adds convenience and ease. The floor plan is both functional and elegant, offering five generously sized bedrooms and well-appointed bathrooms, all thoughtfully positioned to maximize privacy and flow. The property is further enhanced by lush landscaping and an abundance of fruit-bearing trees, including bananas, cherries, kumquats, and papayas, along with a beautifully maintained rose garden. These natural charms create a garden-like atmosphere that complements the lakefront setting. Located in gated Waterside, one of Winter Garden’s most desirable communities, this home offers privacy, exclusivity, and direct access to one of Central Florida’s most beautiful lakes, while remaining close to top-rated schools, dining, shopping, and major roadways. This is more than a house—it is a lifestyle defined by water, space, craftsmanship, and unforgettable outdoor living. Opportunities like this on Johns Lake are rare, and this residence stands apart in both design and execution.

5 Beds ⋅ 6 Baths ⋅ Waterside On Johns Lake SubDv. ⋅ 34787 Zip Code

One or more photo(s) has been virtually staged. Get behind the gate of the highly sought-after Waterside community in Winter Garden. This extraordinary waterfront estate offers a rare blend of refined luxury, thoughtful design, and true lakefront living on Johns Lake. Built just six years ago and meticulously enhanced, this five-bedroom residence is primarily single-story, with the added flexibility of a private upstairs retreat featuring a spacious loft, full bedroom, and bathroom—ideal for guests, multi-generational living, or a quiet home office escape. From the moment you enter, the home makes a statement. Real, solid wood flooring flows throughout, adding warmth and authenticity that cannot be replicated with engineered alternatives. The expansive living areas were extended to create an open and inviting layout, perfectly suited for both everyday comfort and grand-scale entertaining. Dramatic waterfall-edge countertops anchor the kitchen and gathering spaces, blending modern elegance with timeless craftsmanship. The heart of the home extends seamlessly outdoors. An expansive, screened-in lanai overlooks the water, creating a true indoor-outdoor lifestyle. The electric, automatic screening system allows you to adjust the space effortlessly, making it enjoyable year-round. The outdoor kitchen is exceptional, designed for serious cooking and entertaining. It includes a Coyote gas grill, a Recteq pellet grill, a power burner, two outdoor refrigerators, a full-size sink, and a dedicated television—everything needed to host unforgettable evenings with friends and family. Beyond the lanai, the backyard opens to a large, fenced lawn that gently leads to your private dock on Johns Lake. The dock is fully equipped with a boat lift, as well as water and electricity, making lake access effortless and spontaneous. Whether you enjoy boating, fishing, or sunset cruises, this setting delivers the ultimate waterfront lifestyle. The saltwater infinity-edge pool is a showpiece, stretching an impressive 50 feet and designed to visually merge with the lake beyond. Heated by gas, the pool is ideal for both leisurely afternoons and evening swims, offering breathtaking views and a true resort-style experience in your own backyard. Inside, the home continues to impress with high-end features that elevate daily living. A tankless water heater ensures endless hot water, while a central vacuum system adds convenience and ease. The floor plan is both functional and elegant, offering five generously sized bedrooms and well-appointed bathrooms, all thoughtfully positioned to maximize privacy and flow. The property is further enhanced by lush landscaping and an abundance of fruit-bearing trees, including bananas, cherries, kumquats, and papayas, along with a beautifully maintained rose garden. These natural charms create a garden-like atmosphere that complements the lakefront setting. Located in gated Waterside, one of Winter Garden’s most desirable communities, this home offers privacy, exclusivity, and direct access to one of Central Florida’s most beautiful lakes, while remaining close to top-rated schools, dining, shopping, and major roadways. This is more than a house—it is a lifestyle defined by water, space, craftsmanship, and unforgettable outdoor living. Opportunities like this on Johns Lake are rare, and this residence stands apart in both design and execution.

16743 Broadwater Avenue, Winter Garden

$2,700,000

Pre-Construction. To be built. As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in 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! At Briley Farm you will have to opportunity to build with one of three of Central Florida's leading custom home builders, Element Home Builders, Pioneer Builders, and J&J Builders. 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 indoors and out. Briley Farm boasts serene scenery as a picturesque backdrop 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. Stop by our sales office today!

4 Beds ⋅ 6 Baths ⋅ Briley Farm SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in 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! At Briley Farm you will have to opportunity to build with one of three of Central Florida's leading custom home builders, Element Home Builders, Pioneer Builders, and J&J Builders. 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 indoors and out. Briley Farm boasts serene scenery as a picturesque backdrop 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. Stop by our sales office today!

524 N Pollard Street, Oakland

$1,035,833

Beautiful house in Winter Garden.

5 Beds ⋅ 4 Baths ⋅ Lake Star/Ovation Ph 1a SubDv. ⋅ 34787 Zip Code

Beautiful house in Winter Garden.

16795 Muskgrass Drive, Winter Garden

$505,000

Luxury Living in the Gated Community of John’s Landing on Beautiful Johns Lake! This well-maintained, move-in-ready 4-bedroom, 2-bath home offers flexible living in one of Oakland/Winter Garden’s most desirable lakefront communities. Mature landscaping, an oversized driveway, and a 3-car garage provide excellent curb appeal. Inside, abundant natural light, a spacious layout, and thoughtful upgrades create a warm and inviting atmosphere. Beautiful pond view from the rear. The open kitchen and family room flow seamlessly to the rear covered porch and beautifully maintained backyard—perfect for both everyday living and entertaining. Enjoy the outdoors on the large screened-in patio and expansive paver area (sealed in 2025), ideal for relaxing Florida evenings. The 3-car garage includes generous shelving and space for a workshop or storage for kayaks and boating gear—ideal for enjoying the community’s private boat ramp with direct access to Johns Lake. Major Updates Include: New roof, New AC & thermostat (2018), Kitchen & primary bath upgrades: counters, backsplash, cabinet updates; New fence (2024), New outdoor paver patio (2024), Newer appliances: Refrigerator, dishwasher, stove, washer & dryer (2025). John’s Landing residents enjoy amenities such as pickleball, tennis, basketball, a playground, and lake access for boating, fishing, and jet skiing. The location is unbeatable—near top-rated schools, the West Orange Trail, and just minutes from historic Downtown Winter Garden, Plant Street Market, parks, shopping, dining, and the renowned farmers market. Convenient commute to Disney, Universal, Downtown Orlando, the airport, and the area’s new hospital and other upcoming developments. The seller is willing to leave select furniture, including living room and bedroom pieces; final list to be confirmed. All measurements and information are approximate and should be verified by the buyer and/or buyer’s agent. Don’t miss your chance to enjoy the best of Central Florida living—schedule your showing today!

4 Beds ⋅ 2 Baths ⋅ Johns Landing Ph 02 48 138 SubDv. ⋅ 34787 Zip Code

Luxury Living in the Gated Community of John’s Landing on Beautiful Johns Lake! This well-maintained, move-in-ready 4-bedroom, 2-bath home offers flexible living in one of Oakland/Winter Garden’s most desirable lakefront communities. Mature landscaping, an oversized driveway, and a 3-car garage provide excellent curb appeal. Inside, abundant natural light, a spacious layout, and thoughtful upgrades create a warm and inviting atmosphere. Beautiful pond view from the rear. The open kitchen and family room flow seamlessly to the rear covered porch and beautifully maintained backyard—perfect for both everyday living and entertaining. Enjoy the outdoors on the large screened-in patio and expansive paver area (sealed in 2025), ideal for relaxing Florida evenings. The 3-car garage includes generous shelving and space for a workshop or storage for kayaks and boating gear—ideal for enjoying the community’s private boat ramp with direct access to Johns Lake. Major Updates Include: New roof, New AC & thermostat (2018), Kitchen & primary bath upgrades: counters, backsplash, cabinet updates; New fence (2024), New outdoor paver patio (2024), Newer appliances: Refrigerator, dishwasher, stove, washer & dryer (2025). John’s Landing residents enjoy amenities such as pickleball, tennis, basketball, a playground, and lake access for boating, fishing, and jet skiing. The location is unbeatable—near top-rated schools, the West Orange Trail, and just minutes from historic Downtown Winter Garden, Plant Street Market, parks, shopping, dining, and the renowned farmers market. Convenient commute to Disney, Universal, Downtown Orlando, the airport, and the area’s new hospital and other upcoming developments. The seller is willing to leave select furniture, including living room and bedroom pieces; final list to be confirmed. All measurements and information are approximate and should be verified by the buyer and/or buyer’s agent. Don’t miss your chance to enjoy the best of Central Florida living—schedule your showing today!

222 Largovista Drive, Winter Garden

$920,000

Welcome home to 16175 Lew Gem Ct., a luxury 4BR/4BA residence set on a quiet cul-de-sac in the sought-after gated community of Hickory Hammock. A covered entry opens to an impressive foyer with tile flooring, tray ceilings, and sight lines that showcase the home’s spacious, flowing layout. The living room features a beautiful bay window and elegant wall arches leading to the formal dining area, creating an inviting setting for gatherings. The family room transitions seamlessly into the gourmet kitchen, complete with granite countertops, a built-in double oven, stainless steel refrigerator, a large center island for prep and seating, and an airy dinette overlooking the pool. The private primary suite is tucked away at the back of the home and offers two walk-in closets, dual vanities, a garden bathtub, and a separate tiled shower. Two guest bedrooms occupy their own wing, including one with direct access to the pool bath. Upstairs, a spacious loft provides the perfect game or lounge area, accompanied by a full bedroom, full bathroom, and a versatile bonus/media room. Fold-away sliding doors open to an outdoor oasis featuring a screened pool enclosure, expansive deck space, and serene pond views beyond the fenced backyard. Additional highlights include a laundry room and a 3-car side-entry garage. Residents enjoy resort-style amenities—clubhouse, fitness center, community pool, tennis courts, playground, dock, and walking trails. Minutes from Downtown Winter Garden, Winter Garden Village, major highways, and roughly an hour to the nearest beach.

4 Beds ⋅ 4 Baths ⋅ Hickory Hammock Ph 1a SubDv. ⋅ 34787 Zip Code

Welcome home to 16175 Lew Gem Ct., a luxury 4BR/4BA residence set on a quiet cul-de-sac in the sought-after gated community of Hickory Hammock. A covered entry opens to an impressive foyer with tile flooring, tray ceilings, and sight lines that showcase the home’s spacious, flowing layout. The living room features a beautiful bay window and elegant wall arches leading to the formal dining area, creating an inviting setting for gatherings. The family room transitions seamlessly into the gourmet kitchen, complete with granite countertops, a built-in double oven, stainless steel refrigerator, a large center island for prep and seating, and an airy dinette overlooking the pool. The private primary suite is tucked away at the back of the home and offers two walk-in closets, dual vanities, a garden bathtub, and a separate tiled shower. Two guest bedrooms occupy their own wing, including one with direct access to the pool bath. Upstairs, a spacious loft provides the perfect game or lounge area, accompanied by a full bedroom, full bathroom, and a versatile bonus/media room. Fold-away sliding doors open to an outdoor oasis featuring a screened pool enclosure, expansive deck space, and serene pond views beyond the fenced backyard. Additional highlights include a laundry room and a 3-car side-entry garage. Residents enjoy resort-style amenities—clubhouse, fitness center, community pool, tennis courts, playground, dock, and walking trails. Minutes from Downtown Winter Garden, Winter Garden Village, major highways, and roughly an hour to the nearest beach.

Winter Garden