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 perfectly blends small-town charm with modern amenities! Nestled just west of Orlando, Winter Garden is renowned for its picturesque downtown area, vibrant community spirit, and an abundance of outdoor recreational opportunities. With its lush parks, scenic lakes, and the popular West Orange Trail, residents enjoy a lifestyle filled with adventure and relaxation.

One of the standout features of homes in Winter Garden is the inclusion of private mailbox exterior features. These charming additions not only enhance the curb appeal of your property but also provide a sense of personal ownership and pride. Imagine coming home to a beautifully designed mailbox that reflects your style and welcomes you at the end of the day. Whether it’s a classic design or a more contemporary look, these private mailboxes add a unique touch to your home’s exterior.

Winter Garden is also celebrated for its excellent schools, friendly neighborhoods, and a thriving local economy. The city hosts a variety of events throughout the year, including farmers' markets, art festivals, and holiday celebrations, fostering a strong sense of community among residents.

Whether you’re a first-time homebuyer, a growing family, or looking to retire in a serene environment, Winter Garden offers a diverse range of housing options. With its delightful homes, including those with private mailbox features, you’ll find the perfect place to create lasting memories in this enchanting Florida city. Come discover your dream home in Winter Garden today!

Newest Winter Garden Homes with Private Mailbox Exterior Features

2139 Tillman Avenue, Winter Garden
$825,000
4 Beds ⋅ 4 Baths ⋅ Bronsons Landing SubDv. ⋅ 34787 Zip Code
STOP YOUR SCROLL!!! It's not everyday a GORGEOUS home inside the beautiful gated community of Bronson's Landing is available but this Pool Home offers SO MUCH! This 4 bedroom PLUS OFFICE and POSSIBLE 5th BEDROOM home has 4 FULL bathrooms with multiple living spaces, multiple dining areas as well as an extra large 3 car garage. At the heart of the home is the spacious kitchen with an island, perfectly positioned between the main living areas and designed for both everyday life and entertaining. You’ll find granite counter tops, a large center island, double ovens, plenty of cabinetry, and a pantry. One of the best features is that the primary suite and three additional bedrooms are all located on the main floor. The primary bedroom feels like its own private retreat on it's own side of the house with two walk-in closets, dual vanities, a soaking tub, and separate shower. Being a split floor plan, 2 bedrooms share a Jack-and-Jill bathroom that makes this home super functional. This home can easily handle generational living. Upstairs, the over-sized bonus room with its own full bathroom gives you even more possibilities. Use it as a game room, movie room, guest suite, home gym, second office, or even a possible 5th bedroom. There is plenty of flexibility to make the space work for your lifestyle. The backyard is where the Florida lifestyle really shines! Step outside to your own private oasis with a screened saltwater pool, covered lanai, paver deck, and convenient pool bath. The home backs to a beautiful tree-lined green space, giving you extra privacy and a peaceful setting with no home directly behind you. Imagine starting the morning with coffee by the pool, spending the afternoon soaking up the Florida sunshine, and ending the evening relaxing under the lanai. And YES! Location matters! Bronson’s Landing is a sought-after gated community in one of Winter Garden’s most desirable areas, with access to highly regarded schools and an amazing Central Florida location. You’re close to Winter Garden Village, shopping, dining, 429, and all the charm of Historic Downtown Winter Garden. ALSO! Walt Disney World is just a short drive away, making spontaneous trips to the parks, dinner at Disney Springs, or a night watching fireworks that much easier! This home gives you the space of a true family home, the privacy of a beautiful gated community, your own Florida pool, and easy access to everything that makes Winter Garden and the Disney area such a MAGICAL place to live. If you’ve been waiting for a home that offers space, flexibility, privacy with a pool, and a fantastic location, THIS IS THE ONE!

2139 Tillman Avenue, Winter Garden

14656 Pylon Court, Winter Garden
$2,300,000
7 Beds ⋅ 7 Baths ⋅ Isles/Lk Hancock Ph Iii SubDv. ⋅ 34787 Zip Code
Welcome to this beautiful lake-view home in the desirable, gated Isles of Lake Hancock community in Horizon West / Winter Garden! This spacious 7-bedroom, 6.5-bathroom home offers approximately 4,634 square feet of living space on an oversized 0.43-acre lot, with beautiful lake views from both the front and back of the property. The first floor features a spacious primary suite with a sitting area and his-and-hers walk-in closets, three additional bedrooms with bathrooms, and a separate office perfect for working from home, and a formal dining area for family meals and entertaining.The split-bedroom floor plan offers added privacy and flexibility. Upstairs, you'll find three more bedrooms, two bathrooms, and a den, providing plenty of space for family and guests. The home also offers two separate garage spaces, with one currently enclosed and used as a gym that can be converted back into a garage if desired. Enjoy Florida living with a screened-in pool, summer kitchen, solar panels, and beautiful sunset views over the lake. Residents of this gated community enjoy tennis courts, playground and a private boat ramp. Lake Hancock is a nationally recognized water-skiing destination that hosts world-class tournaments. Located in the sought-after Horizon West / Winter Garden area, the community offers convenient access to Walt Disney World, shopping, dining, upscale golf courses, top-rated schools, and SR-429. With plenty of space, beautiful lake views, and a great location, this home has so much to enjoy. Schedule your private showing today!

14656 Pylon Court, Winter Garden

16773 Broadwater Avenue, Winter Garden
$2,575,000
7 Beds ⋅ 6 Baths ⋅ Waterside On Johns Lake SubDv. ⋅ 34787 Zip Code
Experience the ultimate in luxury lakefront living in this exceptional 7-bedroom Mansfield floor plan, offered for sale for the first time by its original owner. Perfectly positioned along nearly 100 feet of shoreline on the spectacular 2,600-acre Johns Lake, this remarkable residence offers approximately 6,300 heated square feet of thoughtfully designed living space, breathtaking panoramic water views, and a rare walkout basement ideal for multigenerational living. Impressive curb appeal and a welcoming courtyard entrance set the stage for soaring ceilings, expansive living areas, and unforgettable lake views from the moment you enter. The magnificent great room is flooded with natural Florida sunshine, featuring an electric fireplace and sweeping views of Johns Lake. The recently renovated gourmet kitchen is a showpiece, boasting an oversized center island, freestanding natural gas range, and separate full-size refrigerator and freezer. The main level features a luxurious owner's suite, dedicated home office, and additional ensuite bedroom. Upstairs, an expansive bonus room complements three generously sized bedrooms and two full bathrooms, providing exceptional flexibility for family and guests. What truly distinguishes this extraordinary lakefront estate is the enormous walkout basement, offering endless possibilities for a home theater, fitness center, entertainment lounge, game room, or custom bar. A SECOND OWNER'S SUITE provides an incredible opportunity for an in-law retreat, extended family accommodations, or private multigenerational living quarters. Thoughtful planning by the original owners includes future pool connections, natural gas stub-outs for additional coach lighting, preplumbing and gas connections for an outdoor summer kitchen, and numerous additional ceiling fan locations. Additional enhancements include plantation shutters, custom closets, and a whole-home natural gas backup generator. Step outside to an expansive backyard showcasing breathtaking 180-degree panoramic views of Johns Lake. Your private covered boat dock with low-maintenance composite decking and boat lift creates the ultimate waterfront lifestyle, with boating, fishing, watersports, and sunset cruises right from your backyard. Spanning Orange and Lake counties, Johns Lake is renowned for its expansive open waters, scenic shoreline, and exceptional fishing. Located within the gated community of Waterside on Johns Lake, residents enjoy resort-style amenities including a beautiful clubhouse, state-of-the-art fitness center, community swimming pool, and playground. This highly desirable Clermont and Winter Garden corridor offers access to sought-after K–12 schools & Foundation Academy, Montverde Academy, and Windermere Prep School. Ideally situated along Marsh Road, this exceptional location places you minutes from outstanding shopping, dining, and entertainment in both Clermont and Winter Garden. Enjoy convenient access to Walt Disney World, SR 429, SR 408, Florida's Turnpike, and Downtown Orlando. Historic Downtown Winter Garden is just minutes away, offering charming boutiques, acclaimed restaurants, the West Orange Trail, community festivals, and its famous Saturday Farmers Market. Combining extraordinary square footage, a rare walkout basement, dual owner's suites, private boating access, and nearly 100 feet of pristine Johns Lake frontage, this remarkable property delivers an unparalleled opportunity to embrace the Florida lakefront lifestyle.

16773 Broadwater Avenue, Winter Garden

13618 Larsen Lane, Winter Garden
$888,000
4 Beds ⋅ 4 Baths ⋅ Glynwood Ii SubDv. ⋅ 34787 Zip Code
Virtually Staged. A true pride-of-ownership home showcasing architectural elegance, extensive upgrades, and the ultimate Florida lifestyle! Welcome to this stunning Winter Garden residence featuring a freshly painted exterior, tropical landscaping, paver driveway, and spacious three-car garage. Inside, soaring 13.5-foot ceilings, architectural arches, double-tiered tray ceilings, and a custom coffered family room ceiling create an impressive atmosphere. The gourmet kitchen features a sprawling granite island with prep sink, 42-inch solid wood cabinetry custom-painted in November 2025, premium GE Profile stainless steel appliances, a cooktop, double ovens, and a separate butler’s pantry ideal for entertaining or a coffee station. Enjoy seamless indoor-outdoor living through 16-foot, four-panel sliding pocket doors opening to a spacious brick-paver, screened lanai. Relax beneath the covered patio with flush-mounted speakers or beside the oversized saltwater pool with a new variable-speed pump installed in October 2025. The private quarter-acre backyard features mature privacy hedging and a convenient pool-access bathroom with a glass-enclosed walk-in shower. The main-level primary suite offers an elegant tray ceiling, a custom walk-in closet system installed in February 2026, and luxury linen and blackout window treatments. More than $100,000 in reported premium upgrades enhance comfort, efficiency, and peace of mind. Improvements include a 2-ton Daikin 15.6 SEER2 HVAC system (September 2025), upgraded R-38 attic insulation (September 2025), zoned 5-ton variable-speed Trane HVAC. Whole house hot water hybrid system: Tankless water heater fed by propane tank as a main source (electric tank can be used as a back-up). Aquasure Harmony whole-house water softener (August 2024), and a roof replaced in August 2016. Smart-home features include pre-wired 7.1 family room surround sound, multi-zone audio, window-tint film, security cameras with hybrid DVR, motion-activated lighting, smart front-door and garage locks, smart thermostats, and a Rachio irrigation controller. The gated subdivision adds another layer of appeal. Located in desirable Glynwood II at StoneCrest, residents enjoy a clubhouse, resort-style pool, playground, tennis courts, and scenic walking trails with pond views, a fountain, and green spaces. Conveniently close to Winter Garden Village, shopping, dining, parks, and the West Orange Trail, the community also offers access to major roadways, Orlando’s employment and entertainment centers, world-famous theme parks, Orlando International Airport, and Florida’s beautiful beaches. Experience exceptional architecture, modern technology, privacy, and effortless entertaining in this remarkable Winter Garden home! Note: The last four photos have been virtually staged.

13618 Larsen Lane, Winter Garden

15725 Signature Drive, Winter Garden
$569,000
6 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code
MOVE-IN READY & EASY TO SHOW! Nestled in the highly sought-after Independence community of Winter Garden, this beautifully maintained Lennar “Rio” floor plan offers the perfect combination of location, lifestyle, and resort-style amenities. This spacious two-story home features 6 bedrooms, 3 full baths, a versatile loft, and 2,714 sq. ft. of living space, all situated on a desirable corner lot. Freshly painted, vacant, and in impeccable condition, this home is ready for its next owner. The thoughtfully designed layout offers generous living spaces, a spacious kitchen with solid wood cabinetry and granite countertops, stainless steel appliances, an interior laundry room, smart thermostat, security cameras, and a private side - backyard. Additional improvements include a newer A/C system, insulated garage, and garage door opener. A covered and screened outdoor area provides additional space to relax and enjoy the Florida lifestyle. Independence is one of Horizon West’s desirable master-planned communities, offering an exceptional array of amenities including clubhouses, resort-style community pools, fitness facilities, tennis courts, playgrounds, parks, sidewalks, and private community boat ramps with lake access. Ideally located near shopping, dining, entertainment, schools, and everyday conveniences, with easy access to SR-429 and Central Florida’s world-famous attractions. Enjoy convenient access to the growing Horizon West area, Winter Garden destinations, restaurants, cinemas, Publix, Walmart, and Walt Disney World Resort. Immaculate, spacious, vacant, and truly move-in ready, this is an exceptional opportunity to enjoy the Independence lifestyle in one of Winter Garden’s most desirable locations. Schedule your private showing today!

15725 Signature Drive, Winter Garden

14807 Winter Stay Drive, Winter Garden
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Panther View SubDv. ⋅ 34787 Zip Code
Welcome to 14807 Winter Stay Drive, a beautifully upgraded luxury residence located in the heart of Horizon West in Winter Garden. Spanning 3,856 square feet of refined living space on an oversized lot, this 5-bedroom, 4-bathroom home combines upscale comfort, privacy, and resort-style living. The outdoor sanctuary is custom-built for the Florida lifestyle, featuring a fully fenced backyard, a heated saltwater pool and spa, a spacious covered lanai with retractable awnings, and scenic sunset views overlooking the prestigious Orange County National Golf Course. Inside, the open-concept layout flows effortlessly for everyday living and grand entertaining. The gourmet kitchen boasts premium appliances, upgraded finishes, and an expansive quartz center island. The primary suite offers a private retreat with a spa-inspired bathroom, complemented by custom closets and a dedicated drop zone for extra organization. Upstairs, a large bonus room provides flexible space for a home theater, media room, or executive office, while an oversized 3-car garage offers generous vehicle and storage space. Value-adding upgrades include an owned solar panel system to significantly reduce energy costs. Situated just 0.5 miles from The Mark Plaza and minutes from Horizon West Hospital, top-rated dining, and shopping, this home offers fast access to SR 429, Florida’s Turnpike, and Walt Disney World. Schedule your private tour today.

14807 Winter Stay Drive, Winter Garden

190 Roper Drive, Winter Garden
$795,000
3 Beds ⋅ 2 Baths ⋅ Westlake Manor 1st Add SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully renovated, turn-key home located just a 10-minute walk north of Downtown Winter Garden, tucked away in a beautiful established neighborhood with mature surroundings and an oversized 0.34-acre lot. With no HOA, a large fenced yard, and extensive upgrades inside and out, this property offers a rare combination of location, space, and quality. The home features block and slab construction with new stucco and approximately 1,750 square feet under air, including the original 1,500-square-foot footprint plus an additional 250-square-foot enclosed and finished porch. The well-designed floor plan offers 3 bedrooms and 2 bathrooms, along with an oversized interior storage/laundry room and an oversized two-car garage. The exterior has been completely refreshed with new stucco, fresh exterior paint, new vinyl fence, new soffits, updated exterior lighting, a new paver driveway, and a new landscaping package, creating exceptional curb appeal. The expansive lot is fully enclosed by a new vinyl privacy fence with a double gate providing convenient access to the rear yard for large vehicles, trailers, boats, or recreational equipment. A motion-sensor security light adds an additional layer of convenience and security. Roof 2019 and AC 2024. Inside, the renovation continues with new insulation, new ductwork, fresh paint and texture, new baseboards, luxury vinyl plank flooring, new ceiling fans and lighting, and updated door hardware throughout. The bathrooms have been completely redesigned with high-end custom tile work and designer finishes. The kitchen is a standout feature, offering 42-inch cabinetry, new appliances, a counter-depth Frigidaire Gallery refrigerator, slide-in range, and an oversized island finished with a stunning marble waterfall edge that coordinates beautifully with the marble backsplash. Bright, dimmable recessed lighting completes the space and creates an inviting atmosphere for both everyday living and entertaining. Additional features include an oversized storage/laundry room under air and an oversized two-car garage equipped with a new garage door opener and recessed lighting. Every detail has been thoughtfully addressed, creating a home that is truly move-in ready. Four-point, WDO, and wind mitigation reports are available in the MLS for review. With its proximity to Downtown Winter Garden, no HOA, expansive 0.40-acre lot, extensive renovation, and exceptional outdoor space, this is a property that offers the best of convenience, privacy, and modern living.

190 Roper Drive, Winter Garden

24 W Garden Avenue, Winter Garden
$698,800
4 Beds ⋅ 4 Baths ⋅ Winter Garden Shores Rep SubDv. ⋅ 34787 Zip Code
RARE OPPORTUNITY IN THE HEART OF WINTER GARDEN’S HIGHLY SOUGHT-AFTER GOLF CART DISTRICT! Completely remodeled and move-in ready, this impressive 4-bedroom, 4-bath, single-story home sits on an oversized lot directly across from Tanner Hall, Newton Park and the public boat ramp to Lake Apopka—and best of all, there is NO HOA! Extensive renovations have transformed this home with a beautiful new kitchen ( NATURAL GAS RANGE! ), remodeled bathrooms, new flooring, fresh interior and exterior paint, and updated windows, creating a fresh, modern feel throughout. The roof was replaced in 2017 and the water heater in 2013. The spacious open great room floor plan is ideal for both everyday living and entertaining, while the oversized owner’s suite provides a private retreat. Two additional bedrooms feature true ensuite baths, offering exceptional flexibility for family, guests, multigenerational living or a private home office. Step outside to the huge covered and screened rear patio overlooking the expansive backyard with plenty of room to relax, entertain and enjoy the Florida lifestyle. The location is truly hard to beat. Walk across the street to Newton Park, Tanner Hall, the Lake Apopka fishing pier and public boat launch, or hop in your golf cart for a short ride to historic Downtown Winter Garden and everything Plant Street has to offer. Enjoy an incredible collection of restaurants, breweries, coffee shops, boutiques and entertainment, along with year-round festivals, community events and the famous Saturday Winter Garden Farmers Market. Outdoor enthusiasts will love being just a quick bike ride from the popular West Orange Trail and minutes from Lake Apopka. Located in a sought-after K-12 school district with convenient access to SR 429, this location provides an outstanding combination of small-town charm, recreation and accessibility to the greater Orlando area. With four bedrooms, four full baths, extensive renovations, an oversized lot, NO HOA and an exceptional location in the Downtown Winter Garden golf cart district, opportunities like this are increasingly difficult to find. Exceptional value, incredible lifestyle and truly move-in ready—this one is PRICED TO SELL!

24 W Garden Avenue, Winter Garden

12349 Westfield Lakes Circle, Winter Garden
$729,000
5 Beds ⋅ 3 Baths ⋅ Westfield Lakes Ph 04 A-F SubDv. ⋅ 34787 Zip Code
Welcome to Westfield Lakes, a charming community nestled along the shores of Lake Beulah in desirable Winter Garden! This beautifully maintained custom built Morrison Home offers 5 bedrooms, 3 full baths, a 3-way split bedroom floor plan. The thoughtful floor plan includes a private bedroom and full bath separated from both the primary suite and additional bedrooms, making it ideal for guests, extended family, or an in-law suite. The home is on an oversized lot with no rear neighbors. From the moment you step inside, you'll appreciate the soaring 12-foot ceilings, abundant natural light, crown molding, and thoughtful design throughout. The spacious kitchen features 42-inch cabinetry, rich granite countertops, upgraded appliances, and plenty of room to gather with family and friends. The open family room is pre-wired for surround sound and overlooks the extended covered lanai and private backyard, creating an ideal space for entertaining or simply enjoying the peaceful Florida lifestyle. The oversized lot offers plenty of room to add a pool. The private primary suite is thoughtfully separated from the additional bedrooms and features a tray ceiling, direct access to the covered lanai, dual vanities, a large garden tub, and a separate fully tiled shower and a custom closet with built ins, which add both functionality and a custom feel. The fifth bedroom offers flexibility as a home office, den, or guest space. Additional features include 18-inch tile flooring, a spacious 3 car garage with epoxy flooring, brick paver driveway, brick privacy fencing, professional landscape edging, and a recently painted exterior. Major updates provide added peace of mind with a NEW ROOF in February 2026, NEW WATER HEATER and NEW A/C October 2026, plus the freshly painted exterior Sept 2026. Westfield Lakes offers residents a beautiful neighborhood park, tennis courts, and a fishing pier along Lake Beulah. Ideally located near West Orange High School, Roper YMCA Family Center, Winter Garden Village, historic Downtown Winter Garden, dining, shopping, entertainment, dog parks, the West Orange Trail, and major roadways including the 429, Turnpike, and 408. This is more than a home, it's an opportunity to enjoy the space, privacy, and lifestyle that make Westfield Lakes such a special place to call home. Come see it for yourself!

12349 Westfield Lakes Circle, Winter Garden

8836 Lakeshore Pointe Drive, Winter Garden
$1,175,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Turnkey, Toll Brothers model home in Winter Garden. This property occupies one of Lakeshore Preserve’s most open and airy homesites next to expansive open green space inside Lakeshore Preserve. Expansive open green space extends along the entire south side of the home, creating a valuable advantage. No next-door neighbor on the home’s south side—the dining room, great room, kitchen and outdoor living areas face open green space, offering green views, abundant natural light and added privacy. Additional green space behind the property extends the sense of openness. A dramatic two-story foyer upon entering. Key design and home features: Smart home technology, shiplap wall detailing, rich wood-beam ceilings. Plantation shutters throughout. The kitchen features a massive center island, farmhouse sink, abundant cabinetry to include deep drawers. Triple sliding glass doors connect the great room to an expansive screened lanai with a fully equipped outdoor summer kitchen. Outdoor dining and lounge spaces. Motorized retractable screens. Backyard features: outdoor putting green and a built-in stone fireplace with modern glass-rock insert. This home is the ideal Florida seasonal residence or second home. With a resort-style community pool and all grounds maintained by the HOA, this turnkey home is ready for easy seasonal living. First floor primary suite is positioned at the rear of the home. Includes a new walk-in closet, a striking primary bath with opposing vanities, a private water closet and a dramatic walk-in shower. Custom tile extends from the floor up the shower walls, with opposing shower systems, multiple shower heads and built-in bench seating. The second floor features a true second living room, three furnished bedrooms and two full baths. One bedroom includes an ensuite bath and full closet, while the other two share a hall bath. When not occupied by guests, the second living room serves as a private lounge, media room, or office space. Turnkey includes: all living area furniture, décor, artwork, rugs, kitchen equipment, dinnerware, glassware and utensils. Utility features to this home: Tankless water heater, in-wall pest system. Lakeshore Preserve amenities include a clubhouse, fitness center, resort-style pool, playgrounds, sand volleyball court. Cable, one-gig internet and ground maintenance are included in the HOA fee. This executive collection home sits on one of the most unique homesites within Lakeshore Preserve. Privacy and sun-drenched light, Toll Brothers coveted upgrades, and this transitional design style fully finished by an interior designer for this model home.

8836 Lakeshore Pointe Drive, Winter Garden

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