Winter Garden Homes with Private Mailbox Exterior Features

Winter Garden Homes with Private Mailbox Exterior Features

Welcome to Winter Garden, Florida—a charming city that beautifully blends small-town warmth with modern conveniences. Nestled in the heart of Orange County, Winter Garden boasts a rich history, vibrant community, and an array of outdoor activities that make it a perfect place to call home. Just a short drive from Orlando, this picturesque locale offers an inviting atmosphere with its historic downtown area, featuring unique shops, delightful eateries, and a lively farmer’s market that draws residents and visitors alike.

One of the standout features of homes in Winter Garden is the inclusion of private mailbox exteriors, which add a touch of personalization and charm to each property. Imagine strolling through your neighborhood, where every mailbox reflects the character of its owner—this is the essence of community in Winter Garden. These private mailboxes not only enhance curb appeal but also provide a sense of pride in homeownership.

In addition to its charming homes, Winter Garden is surrounded by stunning natural beauty, with numerous parks and recreational facilities perfect for outdoor enthusiasts. Whether you enjoy hiking, biking, or simply taking a leisurely stroll, the scenic West Orange Trail offers breathtaking views and a peaceful escape from the hustle and bustle.

With a commitment to fostering a close-knit community and providing top-notch amenities, Winter Garden is truly a hidden gem in Florida. From its delightful homes with private mailbox features to its vibrant local culture, this city has something for everyone. Discover the charm of Winter Garden and find your dream home today!

Newest Winter Garden Homes with Private Mailbox Exterior Features

$859,900
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to 9572 Waterway Passage in the highly sought-after community of Winter Garden! This beautifully move-in ready upgraded D.R. Horton Cresswell floor plan offers the perfect blend of modern style, comfort, and energy efficiency. From the moment you arrive, you'll appreciate the thoughtful enhancements that make this home truly stand out. Inside, laminate flooring flows seamlessly throughout the home, creating a clean, cohesive look with easy maintenance. A stunning geometric accent wall adds a designer touch to the loft and staircase, making a striking first impression. The spacious primary suite has been transformed into a luxurious retreat with a fully customized walk-in closet and a beautifully updated en suite bathroom. The guest bathroom has also been tastefully renovated with contemporary finishes. Step outside to your own private backyard oasis. Enjoy Florida living year-round with a sparkling pool and spa, a fully equipped outdoor kitchen, and built-in Bluetooth speakers—perfect for entertaining family and friends. Privacy bushes and low-maintenance artificial turf create a lush, secluded setting, while permanent exterior lighting enhances both curb appeal and year-round ambiance. Additional highlights include owned solar panels that help improve energy efficiency and reduce utility costs, making this home as practical as it is beautiful. Every detail has been carefully curated, offering move-in-ready luxury in one of Winter Garden's most desirable locations. Don't miss the opportunity to make this exceptional home your own!

9572 Waterway Passage Drive, Winter Garden
$1,800,000
6 Beds ⋅ 4 Baths ⋅ Na SubDv. ⋅ 34787 Zip Code
TWO HOMES FOR THE PRICE OF ONE.... Explore this stunning 10-acre lakefront estate in southwest Winter Garden with everything you’ve been dreaming of within 20 minutes of all the major theme parks in Central Florida. This beautiful tree-lined property offers privacy, shade, and plenty of space for both you and your animals. The owners have enjoyed using the land as a family ranch and oasis for many years, making it an ideal home for horse owners or those who just want to get away to relax and create lasting memories. You’ll also love the peaceful waterfront setting, where you can enjoy breathtaking sunsets. Beyond the incredible land, the property includes a spacious 3,196-square-foot main home with four bedrooms, three bathrooms, fireplace, screened patio and swimming pool with outdoor spa. In 2017 owners built a 1,200-square-foot guest house with a two-car garage, perfect for visitors or extra living space. Both homes are equipped with metal roof and screened porches. Despite its peaceful country feel, you’re still conveniently close to hospitals, restaurants, and shopping. If you’re looking for a property that combines the beauty of ranch living with laid back comfort and convenience, this is the perfect place to call home. Video https://youtu.be/FU5ZvzJ_3PM

16945 W Phil C Peters Road, Winter Garden
$489,990
4 Beds ⋅ 2 Baths ⋅ Fullers Crossing Ph 02 49 31 SubDv. ⋅ 34787 Zip Code
Welcome home to this beautiful 4-bedroom, 2-bathroom single-family residence located in the heart of Winter Garden! Spanning 2,199 square feet of living space, this home features a highly desirable split floor plan with soaring volume ceilings that create an open and airy atmosphere. The spacious layout includes a welcoming living area, laminate flooring in the bedrooms, and an attached 2-car garage. Step outside to your private, screened-in patio overlooking an expansive 8.125-square-foot lot, offering plenty of space for outdoor entertaining or relaxation. Nestled in a quiet neighborhood, this property offers unbeatable convenience. Enjoy fast access to SR 429, the Florida Turnpike, and charming historic downtown Winter Garden. Furniture can also be negotiated! Don't miss the opportunity to own a piece of this highly sought-after community—schedule your private tour today!

1815 Americus Minor Drive, Winter Garden
$870,000
4 Beds ⋅ 4 Baths ⋅ Bronsons Lndgs F & M SubDv. ⋅ 34787 Zip Code
Tucked inside a sought-after gated community, this beautifully designed 4-bedroom, 4-bath home with office/den, offers the perfect blend of comfort, elegance, and everyday livability. From the moment you arrive, you’ll appreciate the sense of privacy, space, and thoughtful design that make this home truly special. With formal living and dining rooms, a private office/study, and a spacious bonus room with a full bath, there is room for everyone to live, work, gather, and unwind. At the heart of the home, the centrally located kitchen brings everything together, opening naturally to the main living areas and creating an ideal setting for both entertaining and daily life. Appointed with granite countertops, a center island, double ovens, and a pantry, it is as functional as it is inviting. Beautiful crown molding, decorative wall details, and tile flooring throughout the main living spaces add warmth and character, while the bedroom spaces provide comfort and privacy. The primary suite is a peaceful retreat, privately positioned and complete with two walk-in closets, dual vanities, a soaking tub, and a separate shower. Secondary bedrooms are thoughtfully arranged, including a Jack-and-Jill bath, while the bonus room provides flexible space for guests, a media room, a playroom, or multi-generational living. Step outside and enjoy your own private Florida oasis. The screened saltwater pool, convenient pool bath, and expansive paver deck with both covered and open-air areas create the perfect backdrop for quiet mornings, weekend gatherings, and year-round outdoor living. Backing to a green area, the setting feels peaceful and private, offering a rare sense of escape while still being close to everything. Located near Winter Garden Village, Highway 429, top-rated schools, shopping, and dining, this exceptional home offers not just a place to live, but a lifestyle to love. Make sure to check out the 3D tour and Virtual tours.

2139 Tillman Avenue, Winter Garden
$474,900
3 Beds ⋅ 2 Baths ⋅ Summerlake Pd Ph 01b SubDv. ⋅ 34787 Zip Code
Virtually Staged. BRAND NEW ROOF! This 3-bedroom, 2-bathroom home features open concept design that connects the main spaces into one flowing layout. The primary suite is located upstairs, and a loft bonus room provides flexible space for a home office or guest retreat. The property combines practical design with convenient access to shopping, dining, and recreation throughout the Winter Garden area. The gourmet kitchen showcases stainless steel appliances and a custom tile backsplash, with solid surface countertops providing durable workspace. Luxury vinyl plank flooring runs through the formal dining area and open-concept great room, while ceramic tile anchors the foyer entryway and kitchen. The primary bedroom features carpet, as do the upstairs bedrooms, loft area, and second floor hallway. Sliding glass patio doors open the interior spaces to outdoor areas, bringing in natural light and creating visual connection to the exterior. The primary bathroom includes dual sinks for convenience, with ceramic tile flooring throughout. A laundry room with storage keeps essentials organized and accessible. The covered lanai extends outdoor enjoyment with shade and shelter, while the fenced backyard provides privacy and security. A covered front porch welcomes visitors at the entry. The architectural shingle roof protects the home, and a smart thermostat manages energy efficiency. The secluded patio offers a quiet retreat, and on clear evenings, you can catch distant Disney fireworks from the property. The community resort-style pool provides year-round recreation and social opportunities for residents. Hamlin Town Center shopping is nearby for everyday needs, while Horizon West Town Center offers expanded retail and dining options. Cinepolis Luxury Cinemas and Publix Super Market are within convenient reach. Golf enthusiasts will appreciate proximity to Orange County National Golf Center. Contact us to schedule a showing and explore this home's location and lifestyle benefits. Seller will entrain offers 5 days after list date.

14629 Bahama Swallow 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
$510,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
Located in the Golf Cart District and less than one mile from Historic Downtown Winter Garden and directly across from the West Orange Trail, this beautifully maintained 3 bedroom, 2 bath home in the Gated Community of Lakeview Reserve offers the perfect blend of location, comfort, and updates. The desirable split floor plan features spacious living and dining areas with an open concept kitchen at the heart of the home. Large windows throughout provide abundant natural light, while the kitchen offers a cozy breakfast nook and overlooks the backyard. The primary suite is a private retreat featuring a custom wood accent wall, soaking tub, and separate walk in shower. Two additional bedrooms are situated on the opposite side of the home, providing privacy for family or guests. Step outside to enjoy the spacious fenced backyard and screened lanai, perfect for relaxing or entertaining. Recent updates include a new roof (2018), exterior paint (2018), fence (2022), screened lanai (2022), gutters (2022), new sod (2025), and brand new carpet. Residents of Lakeview Reserve enjoy the security of a gated entrance, a covered community dock with scenic lakefront seating, and a prime location near shopping, dining, and all that Downtown Winter Garden has to offer. Top rated elementary and middle schools are within walking distance, making this move in ready home an exceptional opportunity in one of Central Florida's most sought after communities.

132 Zachary Wade Street, Winter Garden
$440,000
2 Beds ⋅ 1 Baths ⋅ Borders & Woosley Sub SubDv. ⋅ 34787 Zip Code
Located within Winter Garden’s golf cart district and just minutes from Plant Street, this property offers a distinctive combination of current residential use, C-2 General Commercial zoning, and no HOA. The single-story, concrete-block home includes 2 bedrooms, 1 bathroom, 1,034 square feet of heated living space, an enclosed porch that provides additional flexible space, and a roof replaced in 2023. The interior is ready for renovation, allowing the next owner to update the property according to their intended use and vision. Situated on an approximately 0.19-acre homesite, the property also features mature shade trees, a concrete driveway, and fenced sections of the yard. Its central Winter Garden location provides convenient access to the restaurants, shops, farmers market, community events, and West Orange Trail surrounding downtown and Plant Street, while nearby golf-cart-friendly roadways offer another way to explore the area. Whether considered for continued residential use, a renovation project, or a future business opportunity, this property presents a range of possibilities in a well-connected location. Buyers should independently verify all intended uses, permitting requirements, and zoning regulations with the City of Winter Garden.

721 S Woodland Street, Winter Garden
$719,000
5 Beds ⋅ 3 Baths ⋅ Johns Lake Pointe SubDv. ⋅ 34787 Zip Code
Welcome to 552 Egret Place in beautiful Winter Garden, Florida—an exceptional Meritage Homes residence thoughtfully designed to combine modern style, everyday comfort, and outstanding energy efficiency. From the moment you arrive, you'll appreciate the quality craftsmanship and attention to detail that Meritage Homes is known for. Inside, an open and inviting floor plan creates the perfect setting for both daily living and entertaining. The spacious living areas flow seamlessly into the well-appointed kitchen, featuring abundant cabinetry, generous counter space, a large island, and modern finishes that make gathering with family and friends effortless. The private owner's suite provides a peaceful retreat with a spacious bedroom, an elegant en-suite bath, and a generous walk-in closet. Additional bedrooms provide flexibility for family, guests, or a dedicated home office. One of the standout features of this home is its energy-efficient construction. This home incorporates advanced energy-saving features designed to provide year-round comfort while helping reduce utility costs. Spray foam insulation and energy efficient windows are just some of the certified features that contribute to a more efficient home. Step outside to enjoy the outdoor living space—ideal for morning coffee, weekend barbecues, or simply relaxing while enjoying Florida's beautiful weather. Located in one of Winter Garden's most desirable areas, you'll enjoy convenient access to top-rated schools, shopping, dining, parks, major highways, and the charm of Historic Downtown Winter Garden, known for its award-winning farmers market, local restaurants, boutique shopping, and the West Orange Trail. Whether you're looking for a move-in-ready family home or a smart investment in one of Central Florida's fastest-growing communities, 552 Egret Place offers the perfect blend of quality construction, energy efficiency, modern amenities, and an unbeatable location. Don't miss this opportunity to own a beautifully crafted home where comfort, savings, and Florida living come together.

552 Egret Place Drive, Winter Garden
$900,000
6 Beds ⋅ 6 Baths ⋅ East Garden Manor Add 03 Rep SubDv. ⋅ 34787 Zip Code
Rare opportunity to own a unique corner-lot property featuring two attached residences, each with its own street frontage, private entrance, covered front porch, two-car garage, no HOA, and identical floor plan. Unlike a traditional side-by-side duplex, each residence faces a different street, creating the appearance and feel of two individual homes while offering the convenience of a connected design. Designed for both comfort and flexibility, each home features a spacious living and dining area, a bright kitchen with French doors leading to the backyard, and a convenient first-floor guest powder bath. Upstairs, all bedrooms are thoughtfully positioned for added privacy. The primary suite includes a private ensuite bath, while the secondary bedrooms are generously sized and complemented by abundant storage throughout each residence. The Wilson Street residence has been thoughtfully upgraded with luxury vinyl flooring, an enhanced kitchen with stone counters and gas cooking, beautifully updated bathrooms, and an attractive staircase that adds character and style. The Maple Street residence has been a consistently popular rental and has been exceptionally maintained, offering a spotless interior that reflects pride of ownership. The location offers exceptional convenience with nearby access to Downtown Winter Garden, one of Central Florida’s most sought-after destinations. Enjoy a vibrant mix of locally owned restaurants, cafés, boutiques, specialty shops, the award-winning Winter Garden Farmers Market, seasonal festivals, live entertainment, and the renowned West Orange Trail. The property also provides convenient access to the Florida State Road 429, Florida State Road 408, and Florida’s Turnpike, making travel throughout Central Florida simple. Popular destinations, including Winter Garden Village, Walt Disney World Resort, major employment centers, shopping, dining, entertainment, parks, and everyday conveniences, are all nearby. Whether you’re seeking a property that offers exceptional flexibility for evolving lifestyle needs, the opportunity to generate rental income, or the convenience of two complete residences under one roof, this distinctive property delivers a rare combination of privacy, functionality, and long-term versatility. Opportunities like this are seldom available, especially with a layout that allows each residence to maintain its own identity while remaining connected.

402 E Maple Street, Winter Garden
$289,000
2 Beds ⋅ 2 Baths ⋅ Joe Louis Park First Add SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully renovated 2-bedroom, 2-bath home in the heart of Winter Garden. Blending modern updates with timeless charm, this move-in-ready residence offers stylish finishes, functional living spaces, and a convenient location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright, refreshed interior featuring contemporary flooring, recessed lighting, updated fixtures, and an open, inviting atmosphere. The fully remodeled kitchen showcases elegant white shaker cabinetry, sleek countertops, stainless steel appliances, and modern hardware, creating a clean and sophisticated space for everyday living and entertaining. The renovated bathrooms feature designer-inspired finishes, including a spacious walk-in shower with stunning marble-look tile, upgraded fixtures, and a modern vanity. Thoughtful updates throughout the home provide a fresh, cohesive look while maintaining comfort and functionality. Outside, enjoy a spacious lot shaded by mature trees, offering room for outdoor entertaining, gardening, pets, or future expansion. Fresh exterior improvements and landscaping enhance the home's curb appeal, while the absence of HOA restrictions provides added flexibility and freedom. Conveniently located near shopping, dining, parks, the West Orange Trail, major highways, and all that Downtown Winter Garden has to offer, this turnkey property presents an exceptional opportunity for homeowners and investors alike. Don't miss your chance to own a beautifully updated home in one of Central Florida's most sought-after communities.

1701 E Bay Street, Winter Garden
$800,000
4 Beds ⋅ 2 Baths ⋅ Fries Winter Garden SubDv. ⋅ 34787 Zip Code
Coming Soon! Awesome Opportunity to own in Historic Winter Garden. LOT parcels in the front are being sold seperate.

214 S Woodland Street, Winter Garden
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