Homes for Sale Near Lakeview Middle in Winter Garden - 45 homes

Remarks: Under contract-accepting backup offers. Welcome to this charming and beautifully updated 3-bedroom, 2-bath bungalow located minutes from the heart of highly desirable Winter Garden! This move-in ready home offers the perfect blend of character, comfort, and modern upgrades—including a brand-new roof for peace of mind. Step inside to discover a warm and inviting layout with stylish updates throughout, creating a light and airy feel that’s perfect for both everyday living and entertaining. The cozy bungalow design offers functionality and charm, making it an ideal primary residence, second home, or investment opportunity. Living in Winter Garden means enjoying one of Central Florida’s most sought-after communities, known for its historic downtown, vibrant lifestyle, and strong sense of community. Just minutes away, you’ll find the award-winning Winter Garden Farmers Market, held every Saturday and featuring over 100 vendors, live music, and a lively, family-friendly atmosphere . Stroll along the charming brick-lined streets of downtown, filled with boutique shops, local dining, and cultural attractions. Don’t miss your opportunity to own this adorable, updated bungalow in one of Central Florida’s most beloved communities—schedule your private showing today!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Tara Heard (407-637-4634)

Remarks: Under contract-accepting backup offers. *Ask about a lender provided credit up to $12,500 on this home!* Welcome to 327 S Lakeview Ave, a rare opportunity in the heart of the golf cart district in Downtown Winter Garden. Built in 2014 and tastefully updated, this move-in ready property offers the perfect blend of character, comfort, and flexibility with no HOA. This unique property features a 2-bedroom, 2-bath main home plus a detached 1-bedroom, 1-bath guest cottage, ideal for buyers seeking a multi-generational home, income-producing property, or a home with an in-law suite. Situated on an oversized, fenced corner lot, the property is enhanced by lush, mature landscaping and a charming mini vineyard with sweet muscadine grapevines perfect for homegrown wine or fresh snacking. Inside, the main residence offers a desirable split floor plan with bright, open living spaces and abundant natural light. The inviting living room features a cozy fireplace perfect for relaxing evenings or entertaining guests. The spacious kitchen flows seamlessly into the main living area and is equipped with a gas range, making it ideal for home chefs. The private primary suite is tucked away, creating a peaceful retreat, while the secondary bedroom offers comfort and privacy for guests or family. The detached guest cottage features its own private entrance, making it ideal for rental income, a home office, or private accommodations for extended family. Step outside to the covered back patio, accessible from both the living area and primary suite perfect for entertaining and relaxing. Pre-plumbed with natural gas you can create your dream summer kitchen. The fully fenced backyard and garden space provide both privacy and room to enjoy Florida outdoor living. Located just blocks from the West Orange Trail, Plant Street Market, and the award-winning Winter Garden Farmers Market, you’ll enjoy walkable access to top-rated restaurants, coffee shops, boutiques, and year-round community events. Whether you're searching for a primary residence with rental income potential, a flexible investment property, or a home with a guest house in Winter Garden, this property offers unmatched versatility in one of Central Florida’s most sought-after locations. Don’t miss your chance to own a home near Downtown Winter Garden with income potential and no HOA, schedule your private showing today.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Ryan Leitter (321-684-9699)

Remarks: Under contract-accepting backup offers. Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed enclosed outdoor living, creating seamless indoor to outdoor living. Positioned within the private gated enclave of Deer Island and presented in impeccable condition since its 2015 construction, the home reflects meticulous care and pride of ownership. Thoughtfully designed for a life well lived by owners and guests alike, every detail was executed with intention. Arrival is elegant and memorable, welcomed by a central fountain and expansive motor court leading to an oversized three-car garage, while two bedrooms on the main level, including the primary and guest suite, provide comfort, privacy and effortless livability for generations. Designed for entertaining, walls of fully retractable sliding glass doors dissolve the boundary between indoors and out, allowing the living and great rooms to open to the terrace beyond. The covered outdoor lounge, finished with a wood-paneled ceiling, gas fireplace and fully equipped outdoor kitchen, extends daily living outdoors. The infinity pool and spa, framed by gas fire bowls, merge seamlessly with the lake view itself, while a dedicated pool access bath enhances convenience. Privately positioned to capture sweeping lake views, the primary suite opens directly to the lanai and features dual walk-in closets. Its bath is anchored by a freestanding copper soaking tub, hammered copper sinks set within custom vanities, and a full stone walk-in shower with multiple showerheads and built-in bench. The kitchen features custom wood cabinetry, oversized island, induction cooktop, separate built-in refrigerator and freezer, professional-grade appliances, and walk in pantry. Architectural details include travertine flooring, coffered and tray ceilings, refined millwork and wrought iron staircase. All closets feature custom built-ins. The second-floor media room may also serve as a spacious fifth bedroom with private balcony overlooking the lake. Beyond the terrace, tiered gardens descend toward the shoreline, where Four Seasons marble statuary is thoughtfully placed throughout the grounds, like a work of art set within the landscape. A private putting green, fire pit and manicured lawn enhance the setting. The composite dock includes dual lifts for boat and jet ski, water and electric service, and upper level sun deck positioned for sunset views. John’s Lake spans over 2,500 acres and is known for exceptional clarity, ideal for skiing, boating, water sports and fishing. Deer Island offers gated entry with waterside tennis, pickleball and basketball courts. The home is serviced by a private well. Less than one mile from the Florida Turnpike and 25 minutes to downtown Orlando. Contact for your private viewing.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Candace Cassidy (407-529-8630)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful and spacious 4-bedroom, 2-bath home located in the desirable Fullers Crossing Community in charming Winter Garden. This well-maintained residence has over 2,500 square feet of comfortable living space, perfect for families and those who love to entertain. Step inside to discover a bright open floor plan featuring generous living and dining areas, a large kitchen with plenty of cabinet space, and a welcoming family room that flows seamlessly for everyday living. Conveniently located just minutes from shopping, dining, major highways, and the historic downtown district of Winter Garden, known for its popular farmers market, scenic trails and vibrant community events. You couldn't miss this incredible opportunity to own a beautiful home in one of the Central Florida's most sought-after areas. Contact agent to request your showing today! Some photos have been virtually staged.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Dulce Moise (407-697-4754)

Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bathroom single-story home in highly desirable Winter Garden, Florida! This light and bright residence features an inviting open floor-plan with soaring high ceilings that create a spacious and airy feel throughout. The cozy wood-burning fireplace serves as a beautiful focal point in the main living area—perfect for relaxing evenings at home. The property sits on a spacious corner lot with a fully fenced backyard, offering privacy and plenty of room for outdoor entertaining, pets, or play. A large storage shed (10x16) designed to match the home provides excellent space for tools, hobbies, or additional storage. Located within Winter Garden’s popular golf-cart district, you’ll enjoy easy access to the vibrant historic downtown area. Cruise over to the shops, restaurants, and the beloved weekly farmers market, or take part in the many community festivals and events that make Winter Garden such a special place to live. With its desirable location, open layout, and charming features, this home offers the perfect blend of comfort, convenience, and small-town charm. Call today as these opportunities tend to go fast!

Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)

Listing Agent: Jim Kernohan (407-450-3861)