Explore Winter Garden, FL Homes for Sale

Winter Garden, FL 5 Bedroom Homes for Sale Map Search

5 Bedroom Homes for Sale in Winter Garden, FL

Welcome to your dedicated resource for 5 bedroom homes for sale in Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 5 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

< Back to all Homes for Sale in Winter Garden, FL

All 5 Bedroom Homes for Sale in Winter Garden, FL

$1,100,000
5 Beds 4 Baths Hickory Hammock Ph 1d SubDv. 34787 Zip Code
Welcome to this exceptional pool home in the highly sought-after gated community of Hickory Hammock in Winter Garden. Offering more than 3,600 square feet beautifully designed living space, this impressive five bedroom, four bathroom, 4 car garage residence blends timeless elegance with everyday functionality. From the moment you step inside, you'll be captivated by soaring ceilings, georgous formal dining space, elegant coffered and wainscoting details, custom built-ins, and an abundance of natural light. The open concept floor plan creates an effortless flow, making the home ideal for both intimate gatherings and grand entertaining. At the heart of the home, the gourmet kitchen overlooks the expansive living and dining areas, it features quartz counter tops, abundant cabinetry, generous prep space, and a layout designed for both entertaining and everyday living. A downstairs private home office offers a refined work from home setting, while the expansive upstairs loft is an entertainer's dream, complete with a projector and oversized movie screen, creating the perfect setting for cinematic experiences, game days, or a stylish media lounge. The luxurious primary suite serves as a peaceful retreat with a spacious walk-in closet and spa-inspired ensuite bath. Thoughtfully designed secondary bedrooms and bathrooms provide comfort and privacy for family and guests. Step outside to your own private outdoor oasis where a screened resort-style pool and covered lanai create the ultimate setting for year-round Florida living. Whether hosting guests or enjoying a quiet evening at home, this backyard is designed for relaxation and entertaining. Recent enhancements that showcase true pride of ownership, including a freshly repainted interior, whole home pressure washing, new landscape, and a professionally serviced and cleaned air conditioning system. Residents of the gated community of Hickory Hammock enjoy an exceptional lifestyle with resort-style amenities including a clubhouse, fitness center, community pool, playgrounds, dog park, scenic walking trails, fishing pier, and boat ramp access to the beauty of Johns Lake. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, top rated schools, shopping, dining, SR 429, Walt Disney World, and Orlando's world class attractions, this remarkable home offers the perfect balance of luxury, lifestyle, and convenience. Schedule your showing today!

16044 Citrus Knoll Drive, Winter Garden

$1,195,000
5 Beds 4 Baths Oakland Park Unit 1b-1b SubDv. 34787 Zip Code
Virtually Staged. More than a home, this is a lifestyle. Perfectly positioned in the highly sought-after Oakland Park community, this exceptional residence combines timeless design, generous living spaces, and effortless indoor-outdoor living just a golf cart ride from the heart of downtown Winter Garden. With 5 large bedrooms plus a den spread across over 3,500 square feet, the home provides ample space for everyday living and entertaining. Upon arrival, a welcoming front porch sets the tone, offering the perfect place to enjoy a quiet morning coffee or unwind with a glass of wine at sunset. Inside, elegant French doors open to a private home office, while engineered hardwood flooring flows throughout the main living areas. The open-concept floor plan is filled with natural light, creating an inviting space for both everyday living and entertaining. At the heart of the home, the spacious kitchen overlooks the living area and seamlessly connects to the expansive screened lanai through double French doors. The first-floor primary suite is a private retreat, highlighted by a tray ceiling and a spa-inspired bath featuring dual vanities, a soaking tub, a separate walk-in shower, and an oversized walk-in closet. A secondary bedroom and full bath on the main level provide ideal accommodations for guests or multigenerational living. Upstairs, a spacious loft offers endless possibilities as a media room, game room, or additional gathering space. Three generously sized secondary bedrooms—each with its own walk-in closet—along with two full bathrooms provide comfort and privacy for family and guests alike. Step outside to one of the home's most impressive features: an expansive screened lanai overlooking a fully fenced backyard with ample room to design the pool of your dreams. Completing the property is a coveted three-car garage, offering abundant space for vehicles, storage, and recreation. Residents of Oakland Park enjoy a picturesque, tree-lined community known for its welcoming atmosphere, resort-style amenities, seasonal community events and unmatched location. Just minutes from the award-winning shops, restaurants, farmers market, and West Orange Trail in historic downtown Winter Garden, this home offers the perfect balance of luxury, convenience, and the quintessential Central Florida lifestyle.

844 Oakland Park Boulevard, Winter Garden

$1,046,000
5 Beds 4 Baths Twinwaters SubDv. 34787 Zip Code
Back on the market through no fault of the seller! This home successfully passed the buyer’s 4-Point Inspection, Wood-Destroying Organism (WDO) Inspection, and appraisal, demonstrating its excellent condition. The appraisal has already been completed, and the seller has the appraisal and inspections in hand for you peace of mind. Unfortunately, the previous buyer was unable to secure financing, creating a second opportunity for you to own this beautiful home. The seller is highly motivated and welcomes all reasonable offers. This move-in-ready property is ready for its next owner with no inspection surprises from the previous transaction.Welcome to this stunning architectural masterpiece nestled in the heart of Twinwaters, one of Winter Garden’s most sought-after communities. This elegant two-story home seamlessly blends sophistication and comfort, offering over 3,600 square feet of beautifully designed living space. Step through the grand entryway to find soaring ceilings, expansive windows that fill the home with natural light, and designer finishes that exude contemporary luxury. The gourmet chef’s kitchen is a true showpiece—featuring 42” custom cabinetry, gleaming quartz countertops, a massive entertainment island, stainless steel appliances, and a walk-in pantry, perfect for culinary enthusiasts and family gatherings alike. The open-concept great room flows effortlessly into a spacious dining area and covered lanai, ideal for both indoor and outdoor entertaining. Upstairs, the luxurious primary suite offers a serene retreat with a spacious walk-in closets, a spa-inspired bathroom with a deep soaking tub, frameless glass shower, and dual vanities. A versatile loft provides additional space for a home theater, gym, or play area, while the first-floor guest suite ensures comfort and privacy for visitors. The private backyard invites you to create your own oasis—whether adding a pool, summer kitchen, or lush garden escape. Enjoy resort-style amenities including a community pool, playground, and picturesque walking trails, all surrounded by pristine lakes and lush landscaping. Twinwaters is ideally situated near Horizon West, top-rated schools, fine dining, boutique shopping, and major highways for an easy commute to downtown Orlando and world-famous attractions. This home truly embodies the ultimate blend of luxury, location, and lifestyle—a rare opportunity to live beautifully in one of Central Florida’s premier communities. Special financing options may be available! Qualified buyers may be able to purchase this home with NO MONEY DOWN or through NO INCOME VERIFICATION loan programs, subject to lender approval, program availability, and borrower qualifications. Don’t miss this incredible opportunity. Schedule your private showing today and ask how this home could be yours with little to no money out of pocket!

1711 Amsel Falls Park Terrace, Winter Garden

$689,900
5 Beds 3 Baths Belle Meade-Ph I B D & G SubDv. 34787 Zip Code
Welcome to this beautifully maintained 5-bedroom, 3-bathroom single-story home in the highly sought-after gated community of Belle Meade — zoned for Whispering Oak Elementary (10/10 GreatSchools rating, top 5% of all schools in Florida), SunRidge Middle, and West Orange High School. With 2,918 square feet of thoughtfully designed living space, a 3-car garage, and a fenced corner lot spanning 0.27 acres, this home offers the space, privacy, and top-tier school access today's families are searching for. Major systems have already been taken care of for you — enjoy true peace of mind with a brand new roof (February 2024), backed by a CertainTeed SureStart warranty that's fully transferable to the new owner, and a brand new Trane 5-ton AC system (2025) with a 10-year warranty through 2035. No surprise repairs, no looming replacements — just move in and relax. Inside, soaring cathedral and vaulted ceilings, tray ceilings, crown molding, and wood flooring create an elegant, open feel throughout. A separate laundry room adds everyday convenience, and the fifth bedroom functions as a versatile den/utility space — ideal for a home office, playroom, or guest suite. The primary suite is a true retreat, featuring dual walk-in closets, dual vanities, a spa-style soaking tub, a separate standing shower, and a private water closet. Step outside to your fully screened and covered patio — perfect for entertaining or simply enjoying Florida's year-round sunshine, rain or shine — overlooking the private, fenced backyard. Belle Meade is a secure, gated community known for its lush landscaping, sidewalks, welcoming neighbors, and an on-site dog park. You're just minutes from Winter Garden Village at Fowler Groves — Central Florida's premier outdoor shopping and dining destination — and a short drive from historic Downtown Winter Garden's Plant Street, home to the award-winning Saturday Farmers Market, Crooked Can Brewing Company, and some of the area's best restaurants. Lake Apopka and several highly rated golf courses, including West Orange Country Club and Orange County National Golf Center (home to PGA Tour and LIV Golf events), are also just minutes away. Commuters and theme park lovers alike will appreciate the unbeatable location: Walt Disney World is approximately 15–25 minutes away via SR 429, with Universal Studios and SeaWorld each roughly 20–30 minutes via the Florida Turnpike. Downtown Orlando is approximately 20–25 minutes away via SR 408 or SR 50, and Orlando International Airport is about 30–35 minutes via the Turnpike. This is a rare opportunity to own a move-in ready home with major systems already updated, zoned for one of Florida's top-rated elementary schools, in one of Winter Garden's most desirable gated communities. Schedule your private showing today!

1642 Chandelle Lane, Winter Garden

$934,999
5 Beds 4 Baths Orchard Hills Ph 1 SubDv. 34787 Zip Code
Virtually Staged. Beautifully maintained 5-bedroom, 3.5-bath home with over 4,000 square feet in the highly sought-after Orchard Hills community. Situated on a spacious corner lot, this home offers an ideal floor plan with the primary suite on the first floor and expansive living spaces designed for both everyday living and entertaining. The gourmet kitchen features stainless steel appliances, double wall ovens, an oversized center island, abundant cabinetry, a butler’s pantry, and a large walk-in pantry, all overlooking the open family room and screened lanai. This home is loaded with valuable upgrades, including a SOLAR energy system that helps keep electric costs exceptionally low, with most monthly electric bills averaging around just $33. Additional improvements include a HYBRID energy-efficient water heater, a Pelican whole-house WATER FILTRATION system, and CUSTOM his-and-hers walk-in closets in the primary suite. There is NO CARPET throughout the home, with luxury vinyl plank flooring covering the entire second floor for a modern, low-maintenance finish. The spacious first-floor primary suite offers a private retreat with dual custom walk-in closets and an elegant en-suite bath featuring dual vanities, a makeup station, an oversized walk-in shower, and a soaking tub. Upstairs, you’ll find four additional bedrooms, two full bathrooms, a large loft, and a separate bonus/media room, providing flexible space for family, guests, or working from home. The back yard is fully fenced and plenty of room for a pool. Residents of Orchard Hills enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, dog park, and walking trails with the pool and clubhouse being a couple of minutes walk. The home is zoned for highly rated schools and is conveniently located just minutes from Walt Disney World, the rapidly growing Hamlin Town Center, shopping, dining, and entertainment. With easy access to SR 429, the Florida Turnpike, and SR 408, commuting is simple, and Orlando International Airport is within easy reach. Combining energy efficiency, extensive upgrades, generous living space, and an exceptional location, this home is truly move-in ready.

14301 White Moss Way, Winter Garden

$715,000
5 Beds 4 Baths Carriage Pointe A-I & L SubDv. 34787 Zip Code
Virtually Staged. Lender Credit of 1% (of loan amount) toward closing costs or rate buy-down (inquire for more info). Welcome to CARRIAGE POINT, a GATED Winter Garden community offering an exceptional location and a thoughtfully designed floor plan. This two-story POOL home delivers the space today’s buyers crave, room for everyone, from dedicated home offices to flexible living and guest areas. With 3,435 square feet of living space, this home features five bedrooms, four full bathrooms, and a large bonus room. As you enter the home, you are welcomed by a spacious living room and dining room before continuing into the heart of the home. The open-concept kitchen features granite countertops, 42-inch cabinetry with crown molding, under-cabinet lighting, a gas range, an expanded pantry, and plenty of space for a breakfast table. The kitchen opens to the family room with sliding doors leading out to the SCREENED-IN POOL and FENCED backyard. The first floor features a desirable three-way split floor plan with four bedrooms and three full bathrooms. The spacious downstairs primary suite offers plenty of room to relax, along with a walk-in closet and private en-suite bathroom. Upstairs provides even more flexibility with a fifth bedroom, fourth full bathroom, and a large living area. Newer luxury vinyl plank flooring extends throughout the upstairs and staircase. The outdoor living space is a true highlight of this home with an expansive screened-in SALT WATER POOL ADDED IN 2021. Designed with both relaxation and fitness in mind, the pool features water jets giving a swim-against-the-current feature, creating the perfect space to enjoy a refreshing swim or get in a low-impact workout. Carriage Pointe offers residents a variety of community amenities including a tennis court, playground, soccer field, and walking path. For those who enjoy an active lifestyle, the area offers miles of scenic trails, including the West Orange Trail, along with parks and outdoor activities nearby. The location is ideal, with convenient access to State Road 429 and Highway 50, making travel throughout Central Florida easy. Enjoy being close to Winter Garden Village, the Hamlin area, restaurants, shopping, entertainment, and AdventHealth Winter Garden. Families will appreciate the HIGHLY RATED SCHOOLS, including Whispering Oak Elementary, Hamlin Middle School, and West Orange High School. Historic Downtown Winter Garden is less than five miles away and offers charming shops, local restaurants, the weekly farmers market, the West Orange Trail, and year-round community events. Additional features include a three-car garage, natural gas service through Lake Apopka Natural Gas District, gas washer and dryer, a 2020 water heater, updated electrical service, and added electrical for a built-in microwave. With its exceptional floor plan, private pool, flexible living spaces, and prime Winter Garden location, this Carriage Pointe home offers exceptional space, comfort, and convenience. Schedule your private tour today!

1830 Burdock Drive, 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

$765,000
5 Beds 4 Baths Waterleigh Ph 3b 3c & 3d SubDv. 34787 Zip Code
Welcome to resort-style living in Waterleigh, one of Horizon West's most sought-after master-planned communities. This stunning 5-bedroom, 4-bathroom home offers the perfect blend of space, serenity, and lifestyle, all anchored by breathtaking pond views right from your own backyard. Step outside to your private patio and take in the tranquil water view, the ideal backdrop for morning coffee, evening entertaining, or simply unwinding after a full day. The spacious backyard offers room to play, relax, and make memories, while the lush, HOA-maintained landscaping keeps everything looking its best year-round, no weekends spent on yard work required. Inside, five generous bedrooms and four full bathrooms provide all the flexibility a growing family, multigenerational household, or work-from-home setup could need. The open-concept design flows effortlessly from the heart of the home out to the patio, making indoor-outdoor living feel completely natural. Beyond your front door, Waterleigh delivers a lifestyle that rivals any resort. Enjoy four community pools, two clubhouses, a state-of-the-art fitness center, beach volleyball courts, a miniature golf course, a dog park, a community garden, fishing piers on the stunning 350-acre Hickorynut Lake, and miles of nature trails all within your neighborhood. On clear evenings, catch Walt Disney World's nightly fireworks right from the community. Location puts everything at your fingertips. Hamlin Town Center is just minutes away with dining, PopStroke's Tiger Woods-designed putting experience, Cinépolis Luxury Cinema, and a Publix literally within the community. Historic Downtown Winter Garden, with its beloved Saturday Farmers Market, Garden Theatre, and Crooked Can Brewing, is a short drive. Orlando Health Horizon West Hospital is 10 minutes away, and SR-429 makes commuting to Orlando, Disney, or the airport effortless. Top-rated Orange County Public Schools serve the community, including Water Spring Elementary, Water Spring Middle, and Horizon High School all within 1.5 miles. No CDD. HOA includes lawn maintenance. This is the one.

8807 Sonoma Coast Drive, Winter Garden

Start Your Search