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

Perfectly positioned on a quiet cul-de-sac in the sought-after Oakland Hills community near historic downtown Winter Garden. This FULLY FURNISHED and thoughtfully designed custom home on a single level, combines timeless modern farmhouse architecture with today's finest technology and craftsmanship. Curb appeal abounds with a classic mix of Hardie board siding and brick, anchored by a large, shaded front porch glowing with authentic gas lanterns from New Orleans — a true farmhouse welcome. When evening arrives, intentional landscape lighting accentuates the lush grounds and craftsmanship evident in every corner. Inside, the statement grand great room makes an unforgettable first impression with soaring 22+ foot ceilings, exposed beams, and dormer windows that fill the room with natural sunlight from morning to evening. Throughout the home, ten-foot ceilings, custom moldings and baseboards, LBU lighting with LED bulbs, and natural hardwood floors (in all but the media room) keep the ambiance light and welcoming. The heart of this custom residence is a true chef's kitchen: Monogram appliances, two oversized islands, a 36" gas range, paired with Moen and Kohler fixtures, all wrapped in custom Wellborn cabinetry with soft-close doors and drawers. A back second kitchen — the ultimate working pantry — adds double ovens, a microwave, a commercial Keurig, and abundant storage for effortless entertaining. Just off the main living space, a warm and welcoming library/office with custom-built bookcases and Zoom room offers a quiet retreat. The generous primary suite is a luxurious escape, complete with a spa-inspired bathroom centered around an oversized Kohler clawfoot tub. Two additional guest suites offer king beds and ensuite baths with double vanities, while a thoughfully designed bunk room with its own private bath means every guest feels right at home. Movie nights reach a new level in the dedicated media room with a 4K projector and Atmos surround sound. Outdoor living takes center stage on the expansive covered lanai, where a fully equipped summer kitchen with 36" Coyote natural gas grill, exhaust vent, steel doors, and retractable screen — makes alfresco entertaining effortless. Beyond, a private backyard with a heated pool and natural gas fire pit invites year-round gatherings that won't be forgotten. Enjoy smart home living at it's best with a Crestron home automation system, WattBox® UPS battery, Uniview Turret security cameras monitored by Future Home Integration, plus whole-home Wi-Fi with service options from Spectrum or Quantum. Custom closets, two laundry rooms, and an oversized three-car garage with an incredible amount of extra storage. Oakland Hills is an exclusive enclave of just 17 custom homes, minutes from the West Orange Trail, downtown Winter Garden, and Winter Garden Village. Perfectly positioned with easy access to the Turnpike, SR 429, and SR 408, it makes commuting, theme park visits, and airport runs a breeze. Schedule your private tour today and experience everything this meticulous one-of-a-kind home has to offer!

15217 Farm Stand Court, Winter Garden

$887,066

5 Beds ⋅ 5 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Located off the family room is a den with French doors perfect for work or play and a powder room. Customize this area to meet your needs with an optional bedroom and full bathroom. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey includes Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11869 Shine View Lane, Winter Garden

$850,000

5 Beds ⋅ 5 Baths ⋅ Highlands/Summerlake Grvs Ph 2 SubDv. ⋅ 34787 Zip Code

TURNKEY OPPORTUNITY IN HORIZON WEST! This beautifully maintained residence is offered with a long-term tenant in place through April 2027, providing immediate and stable rental income from day one. Whether you’re seeking a cash-flowing investment property or planning a future primary residence, this home offers the unique benefit of current income with the potential for future owner occupancy upon lease expiration. Located in one of Central Florida’s most desirable and consistently high-demand communities, the property combines strong rental appeal with long-term ownership potential. The home features a modern layout, spacious living areas, quality finishes, and a floor plan that continues to attract and retain quality tenants. Its prime Horizon West/Winter Garden location offers convenient access to major employment centers, shopping, dining, entertainment, top attractions, and major roadways, making it a highly desirable area for both renters and homeowners alike. HOA includes cable and internet, helping reduce owner expenses. Tenant is responsible for all utilities and lawn maintenance, creating a low-management ownership structure. Home includes a brand-new washer and dryer that will convey with the sale. Current lease income and contract can be provided upon request. Tenant occupied through April 2027. Showings by appointment only with advance notice.

15784 Sweet Limetta Drive, Winter Garden

$1,099,000

4 Beds ⋅ 5 Baths ⋅ Estates At Lakeview Preserve SubDv. ⋅ 34787 Zip Code

New Price! Welcome to this beautifully appointed residence in Estates at Lakeview Preserve. Situated on an oversized homesite within this gated Winter Garden community, this exceptional home showcases over $100,000 in owner-added custom upgrades in addition to premium builder selections. Thoughtfully designed and meticulously maintained, it offers an incredible combination of luxury finishes, modern convenience, and resort-style outdoor living that's ready to be enjoyed from day one. Designed with both everyday living and entertaining in mind, the spacious open floor plan features a first-floor owner's suite, generously sized secondary bedrooms, a private flex room ideal for a home office, an oversized upstairs loft with an additional guest suite and full bath, and a three-car garage with included electric vehicle chargers. The heart of the home is the beautifully designed kitchen, complete with quartz countertops, premium cabinetry, abundant workspace, and an open layout that flows seamlessly into the main living area and covered lanai. Throughout the home you'll find custom built-in cabinetry, professionally designed closet systems, and motorized window treatments that add both style and functionality. The backyard was designed to be enjoyed year-round. Relax by the heated pool, entertain from the fully equipped summer kitchen, enjoy your favorite music through the built-in surround sound system, or take advantage of the convenient cabana bath after a day outdoors. Every space was thoughtfully designed to make Florida living as enjoyable as possible. This home is equally impressive behind the walls, featuring an owned solar panel system, whole-home CAT6 networking, enhanced Wi-Fi, smart TV connections, integrated surround sound, security and camera prewiring, and numerous smart-home features that provide modern convenience and energy efficiency. Living in Estates at Lakeview Preserve means enjoying gated access and outstanding community amenities including a resort-style pool, clubhouse, fitness center, playground, scenic walking trails, and beautiful lake views. Conveniently located just minutes from SR-429, Winter Garden Village, Walt Disney World, shopping, dining, and highly rated schools, the location is just as impressive as the home itself. From the extensive custom upgrades to the exceptional attention to detail, this home has been lovingly maintained and thoughtfully improved throughout. Opportunities to own a property finished to this level are few and far between. Schedule your private showing today.

4708 Weatherbell Road, Winter Garden

$1,099,000

6 Beds ⋅ 5 Baths ⋅ Cypress Reserve Ph 2 SubDv. ⋅ 34787 Zip Code

Experience luxury living in this exceptional 6-bedroom, 5-bathroom residence located in the highly sought-after Cypress Reserve community of Winter Garden. Perfectly positioned on a premium homesite with no rear neighbors, this impressive home offers exceptional privacy, tranquil conservation views, and a versatile floor plan designed for today’s lifestyle. The open-concept design showcases beautifully appointed living spaces throughout both floors, making it ideal for multigenerational living or hosting extended family and guests. A dramatic second-floor loft overlooks the main living area, creating an open and inviting atmosphere while providing additional living space. Upstairs also features a second primary suite, three additional spacious bedrooms, a dedicated theater/media room, and a flex room that serves perfectly as a home office, den, or playroom. At the heart of the home is a chef-inspired gourmet kitchen designed to impress, featuring stainless steel appliances, a gas cooktop, double wall ovens, quartz countertops, and an oversized center island with an undermount sink, generous seating, and double-sided cabinetry that provides exceptional storage for both everyday living and entertaining. Motorized shades throughout the main living area add a touch of sophistication and everyday convenience. The spacious family room opens effortlessly to the outdoor living space through triple pocket sliding glass doors, creating a seamless indoor-outdoor lifestyle. Relax year-round on the screened lanai overlooking peaceful conservation views or entertain with ease around the sparkling pool and fully equipped outdoor kitchen featuring a Paradise Grill, built-in sink, and refrigerator. Luxurious owner's suite is a private retreat featuring a spa-inspired bath with dual vanities, a relaxing garden tub, a zero-entry walk-in shower with seamless glass enclosure, and double-door entry to an expansive custom-designed walk-in closet that is sure to impress. A private hallway just off the main living area leads to a spacious guest suite with direct access to the pool, along with a generously sized laundry room for added convenience. Upstairs, you'll find a second primary suite, three additional bedrooms, an expansive loft, a dedicated theater/media room, and a versatile flex room—offering abundant space for family, guests, a home office, fitness room, or additional living area. Additional highlights include a three-car tandem garage offering abundant storage and ample room for a home gym, workshop, or hobby space. LOCATED just minutes from Downtown Winter Garden, the award-winning Winter Garden Farmers Market, Winter Garden Village, shopping, dining, top-rated schools, and major roadways including State Road 429 and Florida’s Turnpike, this exceptional home offers the perfect blend of luxury, comfort, convenience, and location *** This is a rare opportunity to own one of Cypress Reserve’s premier residences and experience the very best of the Winter Garden and true Florida lifestyle. ***

14067 Jomatt Loop, Winter Garden

$905,000

5 Beds ⋅ 5 Baths ⋅ Watermark Ph 4a SubDv. ⋅ 34787 Zip Code

Built by Meritage Homes, this beautifully designed two story home offers the perfect blend of style, functionality, and energy efficiency with solar panels. Step inside and you’re welcomed by a versatile flex room just off the foyer, currently serving as a home office but easily adaptable to fit your lifestyle. The first floor also features a full bedroom and full bathroom, providing added flexibility for guests, multi-generational living, or a private workspace. Continue into the heart of the home where the open concept floor plan features tile flooring throughout the main living areas, a spacious kitchen with a large center island overlooking the living room, and a custom stone entertainment wall with built in shelving that creates a striking focal point. Upstairs, you’ll find a generous loft offering additional living space, along with a spacious primary suite featuring a custom designed walk in closet. The thoughtfully upgraded laundry room includes built in cabinetry and countertop workspace for added convenience. The remaining bedrooms are also located on the second floor, two of the secondary bedrooms are connected by a convenient Jack and Jill bathroom, offering a functional layout that provides privacy while maintaining easy access for family or guests. Step outside to a screened lanai overlooking an expansive backyard that provides exceptional space for future enhancements, including a custom pool, outdoor kitchen, or extended entertaining area. Residents enjoy exceptional community amenities, including a resort style pool with water slides and splash features, a clubhouse, fitness center, playground, tennis courts, and pickleball courts offering something for everyone to enjoy.

15031 Guava Bay Drive, Winter Garden

$945,000

4 Beds ⋅ 5 Baths ⋅ Watermark SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully upgraded 5-bedroom, 5-bathroom floorplan, where comfort meets style in the highly sought-after Watermark community. One of the bedrooms has been thoughtfully converted into a spacious media room by the original owners in 2019, but it can easily function as a fifth bedroom if needed. From the charming front porch to the shining luxury tile floors, this home is filled with elegant touches throughout. As you step inside, you’re greeted by a custom full-length glass wall in the hallway, adding depth and openness to the floorplan. The first room on the left is a fully equipped office. Adjacent is a sophisticated formal dining room with stylish wallpaper. The soaring ceilings and oversized family room are designed for both entertaining and everyday comfort, featuring stunning window treatments, a high-resolution projector, and a built-in surround sound system—perfect for cinematic nights at home. The gourmet kitchen is a chef’s dream, featuring stainless steel appliances, a large quartz countertop, a summer kitchen layout, and designer pendant lights, all of which can remain with the home. The first-floor master suite is a true retreat with blackout window treatments, a spa-like bath with a soaking tub, and a generous walk-in closet. Upstairs, you’ll find three additional bedrooms, a spacious loft, a study/den, and a one-of-a-kind themed game room with a hand-painted moon mural, cloud accents, twinkling ceiling lights, and a second surround sound system. Step outside to a covered patio with a heat-block screen and ambient ceiling lighting—ideal for evening gatherings. Located just a short walk from the luxury clubhouse and nearby commercial plaza, you’ll enjoy resort-style amenities including pool, a fitness center, fire pit, waterslides, tennis and basketball courts—all with a low HOA. This home offers the perfect combination of luxury, convenience, and community living. There are four lights have been removed compared to the original listing photos: • The fixture in the front study room • The one in the formal dining room • The light above the staircase• The one in the morning/breakfast area Please call for showing. Currently occupied by tenant. Tenant will move out Jan 2027.

9567 Meadow Hunt Way, Winter Garden

$669,900

5 Beds ⋅ 5 Baths ⋅ Harvest/Ovation SubDv. ⋅ 34787 Zip Code

Exceptional opportunity in Winter Garden. This stunning 2024 home offers 5 bedrooms, 4.5 bathrooms, and a fully independent Next Gen suite featuring its own private entrance, living room, bedroom, full bathroom, and kitchenette—perfect for multigenerational living, a private home office, or even generating additional rental income. With over $60,000 in completed upgrades, this property delivers exceptional value and a truly move-in-ready experience. Ideally located just minutes from Disney, Flamingo Crossings, Hamlin Town Center, top-rated schools, hospitals, shopping, dining, and entertainment, this home blends modern comfort with unbeatable convenience. The open-concept layout showcases high ceilings, a beautifully remodeled kitchen, porcelain tile flooring throughout the first floor, upgraded second-floor flooring, wood stairs, premium interior paint, a paver driveway and patio, epoxy-coated garage flooring, and numerous additional enhancements. A rare chance to own a nearly new, highly upgraded home in one of Winter Garden’s most desirable areas. Buyer and buyer’s agent to verify all information, including room sizes, HOA details, school zoning, rental restrictions, lease terms, and all property information.

15026 Summer Harvest Street, Winter Garden

$1,699,000

5 Beds ⋅ 5 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to this exceptional lakefront retreat on the shores of Lake Apopka, where breathtaking water views, luxury upgrades, and exceptional outdoor living come together to create the ultimate Florida lifestyle. Offering 5 bedrooms, 4.5 bathrooms, and over 4,000 square feet of thoughtfully designed living space, including a convenient first-floor bedroom, this beautifully updated residence showcases more than $500,000 in improvements, creating a move-in-ready experience for the next owner. From the moment you arrive, you'll appreciate the extensive upgrades throughout the home, including porcelain tile throughout the main living areas on the first floor, engineered white oak hardwood flooring throughout the second level, a custom wood and iron staircase, upgraded cabinetry, quartz countertops, designer finishes, and a beautifully appointed kitchen featuring premium KitchenAid appliances, a gas cooktop, and custom soft-close cabinetry. Designed for both everyday living and entertaining, the backyard is a true showpiece. Enjoy a resort-style saltwater pool and spa, gas-heated for year-round enjoyment, expansive outdoor living areas, and a fully equipped summer kitchen featuring premium Blaze appliances. Electric screens allow you to enjoy outdoor dining and entertaining comfortably while taking in the peaceful lakefront setting and stunning sunset views. Boating enthusiasts will appreciate the private dock complete with a 5,000-pound boat lift, offering direct access to Lake Apopka, one of Florida's largest lakes. With more than 30,000 acres of open water to explore, the lake offers endless opportunities for boating, fishing, watersports, and unforgettable sunset cruises. Known for its trophy bass fishing, abundant wildlife, and expansive waterfront views, Lake Apopka provides a rare opportunity to enjoy true lakefront living with the freedom and space that few Central Florida lakes can offer. This property delivers the waterfront lifestyle Florida is known for. Additional highlights include a convenient first-floor bedroom, a second-floor laundry room, solar panels that will be paid off at closing, natural gas service, a Culligan water filtration system, dual pool pumps, and city sewer, a significant advantage for a waterfront property. Ideally located just minutes from Downtown Winter Garden, shopping, dining, and major roadways, this exceptional lakefront residence offers the perfect balance of luxury, recreation, and everyday convenience.

1144 Hull Island Drive, Winter Garden

$879,831

5 Beds ⋅ 5 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 5 bedrooms and 4.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual dining area, family room and outdoor lanai. This home features a spacious kitchen island with built in sink and dishwasher to optimize counter space, and walk-in pantry for extra storage. All homes in this community will have stainless steel appliances, making cooking a piece of cake. Off the Family room is a bedroom and full bathroom. As we head up to the second floor, we are greeted with a loft area and all four bedrooms. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity and separate toilet area. Two additional bedrooms share a second upstairs bathroom and linen closet for extra storage. While a fourth bedroom is complete with ensuite bathroom. Your laundry room is located on the second floor for convenience. Like all homes in Waterleigh, the Torrey includes a Smart home technology package which allows you to control your home with your smart device while near or away. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

11827 Shine View Lane, Winter Garden

$950,000

5 Beds ⋅ 5 Baths ⋅ Silverleaf Reserve/Hamlin Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to Silverleaf in Horizon West, where luxury, space, and convenience come together just minutes from world-class attractions and approximately 25 minutes from Disney. Hamlin Town Center is also just a few minutes down the road, offering all of the staples in addition to dining, shopping, and nightlife. This stunning 5-bedroom, 4.5-bath residence offers nearly 4,000 square feet of thoughtfully designed living space with exceptional upgrades throughout. The heart of the home is the beautifully appointed gourmet kitchen featuring ceiling-height cabinetry, quartz countertops, an extended designer backsplash, and abundant storage, all opening seamlessly to the spacious great room—perfect for entertaining and everyday living. A private guest area with a full bath off the rear hallway provides comfort and flexibility for visitors or multigenerational living. Step outside to an expansive backyard with no rear or side neighbors, creating a private setting for relaxation and recreation. The covered lanai is pre-plumbed for an outdoor kitchen and ready for your vision of the ultimate backyard oasis. A striking open staircase with modern wire railing leads to the second floor, where a massive loft serves as a central gathering space surrounded by three secondary bedrooms and the luxurious primary suite. The spacious primary retreat includes a versatile bonus room ideal for a home office, fitness area, nursery, or private sitting room. The spa-inspired primary bath features a large soaking tub, frameless glass shower, a tasteful tile package, and a walk-in closet with a custom organization system. Additional highlights include a second-floor laundry room with upgraded cabinetry and utility sink, extra recessed lighting throughout, a newly installed EV charger,, and an epoxy-coated garage floor, and a covered front porch with room for chairs to sit and watch the world go by. You are also just steps from Hamlin Elementary and Hamlin Middle school making it easy to avoid that dreaded drop off/pick up loop by walking or biking your kiddos to school. Located in the highly desirable Horizon West area near shopping, dining, top-rated schools, and major roadways, this exceptional home offers the perfect blend of elegance, functionality, and Florida living.

16043 Silver Brook Way, Winter Garden

$2,190,000

5 Beds ⋅ 5 Baths ⋅ Boyd-Lutz Sub SubDv. ⋅ 34787 Zip Code

Virtually Staged. Built by the owner with uncompromising construction standards, this Winter Garden masterpiece delivers the kind of quality and engineering you simply don’t find in today’s market. And with the seller just reducing the price, this luxury home is now an even more exceptional opportunity. Custom built pool renderings and pricing available. Concrete structural design, hurricane-rated engineering, impact windows, full foam insulation, fiber-cement siding, and an Ipe hardwood porch set the tone for durability and refinement. Inside, natural light pours across level-5 walls, rich wood flooring, crown molding, and custom shutters—creating a warm, polished, magazine-worthy aesthetic. The open living and chef’s kitchen are built for elevated living: gas range, pot filler, handcrafted cabinetry, and a dramatic retractable pocket door that dissolves the boundary between indoors and out. The resort-style back porch is a showpiece—pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, and a half bath—perfect for hosting unforgettable evenings. The primary suite is pure indulgence, featuring a spa-inspired bath with dual shower heads, soaking tub, digital controls, a custom closet, and a private concrete safe room. A butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring elevate everyday convenience. Upstairs, the bonus/game room and oversized balcony create a luxe hangout zone. Storage is abundant with walk-in closets throughout. And the finished two-story garage loft—pre-plumbed and air-conditioned—offers endless possibilities: in-law suite, golf simulator lounge, gym, office, or creative studio. Outside, curated landscaping, gas lanterns, an architectural driveway, and a heated concrete hot tub with Wi-Fi controls complete the experience. All just moments from Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre. Craftsmanship, luxury, and location—now at an even more compelling price.

20 W Crest Avenue, Winter Garden

5 Bathroom Homes for Sale in Winter Garden, FL

All 5 Bathroom Homes for Sale in Winter Garden, FL

The Nest Group

Search

Resources

About