Winter Garden/Oakland Homes with Community Mailbox Community Features

Winter Garden/Oakland Homes with Community Mailbox Community Features

Welcome to Winter Garden and Oakland, a picturesque blend of small-town charm and modern convenience located in the heart of Orange County, Florida. Nestled just a short drive from the vibrant city of Orlando, this region is renowned for its lush landscapes, scenic lakes, and a thriving community atmosphere. With a rich history that dates back to the 19th century, Winter Garden boasts a delightful downtown area filled with quaint shops, delightful cafes, and a bustling farmers market that brings residents together every Saturday.

The homes in this enchanting region are designed with community in mind, featuring charming neighborhoods that often include community mailboxes. These community mailbox setups foster a sense of camaraderie among residents, encouraging friendly interactions and a neighborly spirit. Imagine stepping outside your door to collect your mail, exchanging smiles and greetings with fellow residents as you stroll through the beautifully manicured streets.

Winter Garden and Oakland offer a variety of housing options, from cozy single-family homes to modern townhouses, ensuring there's something for everyone. Residents enjoy access to top-rated schools, numerous parks, and recreational facilities, making it an ideal location for families and retirees alike.

With the enchanting backdrop of Florida's natural beauty and a strong sense of community, Winter Garden and Oakland invite you to discover your dream home. Whether you’re seeking a peaceful retreat or an active lifestyle, this region promises a warm welcome and a vibrant place to call home. Come explore the possibilities and experience the charm of Winter Garden and Oakland today!

Newest Winter Garden/Oakland Homes with Community Mailbox Community Features

$229,900
2 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Beautifully refreshed and ready to move in today, this charming 2-bedroom, 1-bath corner condo offers an inviting combination of modern updates, natural light, and exceptional community amenities. The bright, crisp interior is filled with loads of natural light and features fresh paint throughout, brand-new carpet, new door handles, and stylish modern finishes. All appliances are included, making this home truly move-in ready. The attached garage has also been washed and painted, creating a clean and functional space for parking and storage. And when it comes to value, this one is hard to beat. This is currently the most aggressively priced 2-bedroom condo with an attached garage on the market, making it a rare opportunity for a buyer looking for the combination of price, updates, and convenience. The A/C system was newly installed in June 2026, adding another significant update and valuable peace of mind. The community offers an impressive lineup of amenities designed to enhance everyday living, including a resort-style pool and relaxing hot tub, fully equipped fitness center, indoor basketball and racquetball courts, tennis court, and a convenient car wash area. Conveniently located near 429 and the Florida Turnpike, this home provides easy access to shopping, dining, major roadways, and a short drive to Orlando's theme parks and either coastline. With its desirable corner-unit location, attached garage, extensive updates, incredible amenities, and unmatched price point, this is a rare find that won't be easy to duplicate. If you're looking for a move-in-ready 2-bedroom with an attached garage at the best value currently available, this one deserves a look!

233 Southern Pecan Circle Unit 101, Winter Garden
$849,000
5 Beds ⋅ 5 Baths ⋅ Lakeview Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully upgraded five-bedroom, five-bath home in the gated community of Lakeview Preserve. Built in 2022 and offering 4,495 square feet, this impressive corner-lot home features a three-car garage, spacious living areas, thoughtful upgrades, and an incredible backyard designed for entertaining and enjoying the Florida lifestyle. The main level features an open and functional floor plan with luxury vinyl plank flooring throughout, a spacious living room, separate dining area and a beautifully appointed kitchen with quartz countertops, oversized island, soft-close cabinetry, under-cabinet lighting and a custom-designed pantry. The living room and kitchen open through multi-slide pocket doors to the covered lanai, creating an ideal indoor-outdoor living space. The backyard is a standout feature, with a stunning saltwater pool complete with five waterfalls, lighting, a sun shelf, Badu swim jets and an attached spa (not heated). The covered lanai includes two fans, surround sound, a full bath and is prepped for an outdoor kitchen. It is the ideal setting for relaxing, entertaining and enjoying beautiful Florida weather. The spacious primary suite is on the first floor and features a custom-designed walk-in closet, tray ceiling, and beautifully upgraded bath with dual shower heads and soft-close cabinetry. Two additional bedrooms are downstairs, including one with a private en-suite bath, along with a versatile flex room featuring a custom built-in wall unit that can easily serve as an office or additional living space. Upstairs offers even more room to spread out with a large loft, two additional bedrooms, a full bath and an impressive private theater featuring a 120-inch screen, projector, surround sound and motorized blackout shades. The home also offers an extensive list of upgrades and conveniences, including whole-home water filtration, hybrid water heater, recessed lighting, built-in TV wiring, Wi-Fi boosters, two air-conditioning units, security cameras, alarm system, and smart-home controls for many of the home's lights, air conditioner, garage doors and locks. The three-car garage features a durable polyaspartic floor. Lakeview Preserve offers residents an array of amenities, including a fitness center, resort-style pool, cabana, splash pad, playground, and direct access to Johns Lake with a kayak launch and dock. The community is conveniently near shopping, dining, golf, the West Orange Trail, Disney, Universal, Winter Garden, and major roadways including SR 50 and the 429. This is a home that offers the space, upgrades and outdoor living that make Florida living so enjoyable.

3362 Hanging Tide Street, Winter Garden
$659,310
4 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12325 Silk Mimosa Alley, Winter Garden
$870,000
5 Beds ⋅ 5 Baths ⋅ Harvest/Ovation Ph 2 SubDv. ⋅ 34787 Zip Code
A truly special luxury residence in the highly desirable Harvest at Ovation community of Winter Garden. Professionally designed and curated by a team of high-end architects and interior designers, this magazine-worthy home features soaring ceilings, premium finishes, designer furnishings, elegant décor, and exceptional attention to detail throughout. A standout feature is the fully finished private studio above the garage, complete with full bathroom, walk-in closet, and independent access—perfect as a guest suite, additional apartment, executive office, or private workspace. The gourmet kitchen features premium finishes and a state-of-the-art smart double-door refrigerator with internet connectivity. Enjoy Florida living in the screened outdoor area with mosquito protection, electric retractable awning, outdoor grill, and fenced yard. Additional upgrades include fully paid solar panels, whole-home water filtration, premium kitchen water purification, epoxy garage flooring, LED ceiling lighting, EV charger, and paver waterproofing. Ideally located near excellent schools, shopping, dining, major highways, and Central Florida attractions. **Designer furnishings and décor are negotiable.** A rare opportunity to own a beautifully designed luxury home where every detail has been thoughtfully perfected. This is one you truly need to see in person.

16192 Honey Harvest Street, Winter Garden
$999,270
4 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Discover the perfect blend of luxury, comfort, and convenience in this stunning Mahogany Grand home. Thoughtfully designed for both everyday living and entertaining, this exceptional two-story residence offers 4 bedrooms, 3 full bathrooms, a convenient first-floor powder room, an enclosed flex room, and a spacious 3-car garage. The open-concept living area seamlessly connects the gourmet kitchen, café, and gathering room, creating an expansive and inviting space. Soaring ceilings and an elegant tray ceiling enhance the sense of openness, while a large pocket sliding glass door extends the living space onto the covered lanai, filling the home with natural light and creating the perfect blend of indoor and outdoor living. At the heart of the home, the gourmet kitchen showcases stacked soft-close cabinetry, quartz countertops, a decorative tile backsplash, farmhouse sink, and built-in Whirlpool stainless steel appliances, including a natural gas cooktop, range hood, and 48-inch side-by-side refrigerator. Whether preparing everyday meals or hosting special gatherings, this kitchen is designed to impress. Privately situated in the back corner of the home, the spacious owner's suite offers a peaceful retreat and features an owner's suite extension, providing additional space for a sitting area, fitness nook, workspace, or whatever best suits your lifestyle. The spa-inspired en suite bath includes a walk-in closet, linen closet, walk-in shower with a rain shower head, and a private enclosed water closet. The enclosed flex room at the front of the home adds valuable versatility and can easily function as a home office, fitness room, playroom, or creative studio. Two additional first-floor bedrooms located in the opposite back corner of the owner’s suite provide comfort and privacy for everyone. A conveniently located powder room further enhances the home's thoughtful design. Upstairs, enjoy an additional 884 square feet of flexible living space, complete with a generous loft, private fourth bedroom, and full bathroom, making it ideal for a media room, guest suite, home office, or multigenerational living. Completing the home is a spacious 3-car garage with ample room for vehicles, storage, and hobbies. Don't miss the opportunity to tour this exceptional home and experience everything it has to offer.

289 Crystal Wood Drive, Winter Garden
$480,085
3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Ready in December 2026! 3 Level Townhome with 3 Bedrooms! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms with a powder room, spanning 1,846 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by a Study room. As you continue up, you will find luxury vinyl plank flooring that that leads you to the open concept living room, dining room and stunning kitchen. Delighted by the large eat-in island, 42 in. cabinets with crown molding, quartz counters and soft-close drawers. Your eyes will be drawn to the bank of windows flooding your dining room and kitchen with light. Moving to the third level, you have quick access to the generously sized primary suite that accesses your ensuite bathroom with glass-enclosed shower, dual vanities, and the roomy, well-lit walk-in closet. Adjacent to the primary suite is your laundry room with adjacent, secondary bedrooms and guest bath.

15213 Groveside Road, Winter Garden
$1,395,000
4 Beds ⋅ 3 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Newly remodeled in 2026 and presented in like-new condition, this exceptional single-story lakefront home blends an elevated luxe coastal feel with relaxed Florida waterfront living. Set on a rare oversized lot along skiable Huckleberry Lake, the property offers exceptional privacy and space, with approximately 40 feet of separation between neighboring homes. The light and inviting interior features (4) four bedrooms, (3) three full baths, and a spacious open-concept floor plan. The beautifully updated kitchen showcases quartz countertops and flows seamlessly into the main living and entertaining areas. A generously sized open flex room offers additional versatility as a formal dining room, home office, formal living room, or sitting room and can easily be enclosed for additional privacy. Step outside to a large fenced backyard with a private pool and spa, all overlooking Huckleberry Lake. Enjoy direct lake frontage and water access, with the opportunity for a private dock, subject to applicable HOA approval and permitting. The (3) three-car garage includes a Tesla EV charger, and the expansive driveway accommodates up to (6) six additional vehicles. Lakeview Pointe offers a community dock on Huckleberry Lake, resort-style pool with splash area, and fully equipped fitness center. The HOA also takes care of the home's exterior lawn maintenance, giving you more time to enjoy the lake, pool, and Florida lifestyle. Ideally located in Winter Garden's Horizon West area, with easy access to SR 429 and minutes from shopping, dining, entertainment, and everyday conveniences. The property is currently zoned for A-rated Summerlake Elementary, Hamlin Middle School, and Horizon High School. Nearby early-learning options include Primrose School of Horizon West, The Learning Experience - Horizon West, and KLA Schools of Horizon West. Walt Disney World is approximately 20 minutes away. Buyers should independently verify current school assignments and grades. A rare opportunity to own a beautifully remodeled single-story pool home on skiable Huckleberry Lake, combining privacy, flexible living spaces, an oversized lakefront lot, and true Florida waterfront living.

14048 Larkspur Lake Drive, Winter Garden
$895,260
5 Beds ⋅ 4 Baths ⋅ Winter Grove SubDv. ⋅ 34787 Zip Code
Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Step into the Imperial, where luxury and convenience seamlessly combine to create a truly elevated living experience. This remarkable 5-bedroom, 3.5-bathroom home with a 2-car garage situated on a conservation view homesite offers unparalleled craftsmanship and thoughtful design throughout. The open-concept layout flows effortlessly, creating an expansive, airy feel that exudes both sophistication and comfort. On the first floor, discover a private en suite bedroom with a walk-in closet and elegant quartz countertops—a perfect retreat for guests. At the heart of the home, the chef-inspired kitchen is a true masterpiece, featuring Winstead White stacked cabinetry, striking quartz countertops and a decorative tile backsplash. Built-in Whirlpool stainless steel appliances, including a refrigerator and natural gas cooktop, make cooking a pleasure. The kitchen seamlessly connects to the café and gathering room, where a sliding glass door opens to the covered lanai, featuring pre-plumbing for an outdoor kitchen to enhance indoor-outdoor living, all overlooking tranquil conservation views. The first floor also offers a convenient powder room, perfect for guests, as well as a bedroom with an attached bathroom. Upstairs, the luxurious owner’s suite is a private sanctuary, featuring a spacious walk-in closet and a spa-like en suite bathroom with quartz-topped dual vanity sinks and a frameless glass enclosed shower. The loft area provides the perfect space to unwind, while three additional bedrooms and another bathroom complete the upper level. For added convenience, a thoughtfully located upstairs laundry room simplifies everyday tasks. Beautiful wood-look tile flooring is found throughout the first floor, laundry room, and bathrooms, while plush, stain-resistant carpet complements the loft and bedrooms. Designer-curated finishes elevate every corner of this home, including thoughtfully placed brushed nickel plumbing fixtures and hardware, comfort height toilets, Whirlpool washer and dryer, 2” faux wood blinds, and wood treads and risers at the staircase. This home is equipped with a smart thermostat, video doorbell, and LED down lights ensuring your home is as connected as it is beautiful. This home offers the perfect combination of luxury, convenience, and modern design—an ideal place to live and relax. Schedule a tour today!

427 Winter Grove Boulevard, Winter Garden
$975,000
5 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3a SubDv. ⋅ 34787 Zip Code
Welcome to 9566 Bolero Rd, where luxury, space, and location come together in one of Central Florida’s most desirable and rapidly growing communities—Winter Garden. Situated on a premium 60-foot lot with beautiful pond views, this impressive North Haven model offers 5 bedrooms, 3.5 baths, a first-floor primary suite, spacious loft, and oversized fenced yard, all tucked away on a quiet cul-de-sac. Step inside through the dramatic two-story foyer and discover a bright, modern floor plan designed for both everyday living and entertaining. The gourmet kitchen features 42” cabinetry with crown molding, upgraded stainless-steel appliances, a vent hood, generous workspace, and an open layout overlooking the family room and picturesque pond beyond. Extend your living outdoors to the spacious backyard featuring a pergola, fenced yard, and tranquil water views—the perfect setting for morning coffee, entertaining, or relaxing at the end of the day. The first-floor primary suite offers privacy and convenience with a spacious walk-in closet and ensuite bath featuring dual vanities, a large walk-in shower, and garden tub. Upstairs, a generous loft provides flexible space for a media room, playroom, home office, or second living area. Bedrooms 2 and 3 share a full bath, while Bedrooms 4 and 5 are connected by a convenient Jack-and-Jill bath. The laundry room is also pre-plumbed for a utility sink. Enjoy the benefits of a resort-style, maintenance-free community while being surrounded by everything that makes Winter Garden such an exceptional place to call home. The area continues to flourish with new restaurants, shopping, grocery stores, entertainment, and everyday conveniences, while still offering the charm and lifestyle Winter Garden is known for. Enjoy easy access to Walt Disney World, Disney Springs, Publix, SR-429, I-4, and SR-417, connecting you to Orlando’s world-class attractions, employment centers, and entertainment. Whether you're enjoying peaceful pond views from your backyard, exploring nearby dining and shopping, or heading out for a day at Disney, 9566 Bolero Rd offers the space, lifestyle, and location you've been looking for. Welcome home!

9566 Bolero Road, Winter Garden
$410,000
3 Beds ⋅ 3 Baths ⋅ Ravenna Ph 1 SubDv. ⋅ 34787 Zip Code
BEAUTIFUL two-story townhome in the desirable Ravenna community. This spacious 3 bed/2.5 bath offers low-maintenance living in a prime Winter Garden location. The main level is an open-concept with a half bathroom for guests. The kitchen features QUARTZ countertops, stainless steel appliances, a large kitchen island and a breakfast bar...PERFECT for entertaining! All bedrooms are located on the second floor along with the laundry closet. The primary suite includes a WALK-IN closet and an en-suite bathroom with double vanity sinks. Enjoy outdoor living on the private back patio, which leads to the 2-car garage. The community features a POOL and playground. It is conveniently located in Winter Garden near grocery stores, restaurants and top rated schools.

8013 Basilica Lane, Winter Garden
$989,000
4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to 14038 Jomatt Loop, where impressive curb appeal, spacious living, and exceptional outdoor entertaining come together. This home is located just steps from A rated schools, has fresh exterior paint, and a large driveway with 3 car garage. Inside, the spacious open floor plan creates an inviting flow between the main living areas, offering plenty of room for everyday life and entertaining. A dedicated theater room provides the perfect setting for movie nights, sporting events, and unforgettable gatherings. Step outside and discover your own private retreat. The beautiful pool, surrounded by a freshly screened lanai, creates an ideal space for relaxing, entertaining, and enjoying the Florida lifestyle year-round. A durable metal fence adds both privacy and peace of mind while complementing the beautifully landscaped property. For added convenience, the home is equipped with a state-of-the-art security system. From its attractive exterior and expansive lot to its upgraded outdoor living spaces and versatile interior, this exceptional home offers the perfect blend of comfort, style, privacy, and entertainment. Schedule your private showing today!

14038 Jomatt Loop, Winter Garden
$845,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2c-1 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully RENOVATED home, The SEA CLIFF model -One of the largest floorplans in the Waterleigh community.where modern elegance meets comfortable living. The home has been extensively updated with a sophisticated neutral palette, designer lighting, luxury vinyl plank flooring, custom-style cabinetry, quartz countertops, and upgraded fixtures throughout. . This beautiful 2 story home features 4 bedrooms & 3.5 full baths,as you enter the foyer, you are greeted with a formal dining room. Customize this area to meet your needs with an optional den. The show-stopping kitchen is the heart of the home, featuring a large waterfall-edge island, abundant cabinetry, statement backsplash, upgraded appliances, and beautiful accent lighting. The open-concept design seamlessly connects the kitchen, dining, and living spaces, creating an ideal setting for both everyday living and entertaining. bathrooms have been stylishly renovated with contemporary vanities, quartz countertops, modern black fixtures, designer mirrors, and beautiful tile finishes. Additional highlights include custom wall paneling, upgraded trim, elegant lighting, and carefully curated finishes throughout. within walking distance of the community clubhouse and amenities This amazing home is in the highly desirable community “Waterleigh.” Located just off the 429 west of Disney, This community amenities include a huge resort style pool, fitness gym, club house, dog park, huge sports fields, playground, beach volleyball, Tennis, lake view BBQ/picnic area, with sidewalks that wind around the scenic lakes, nature, and community for a relaxing and enjoyable lifestyle with periodic fitness stops if you choose. Fast and easy access anywhere. Hospitals, restaurants and shopping are all nearby. Great schools; Water Spring Elementary, Water Spring Middle, and Horizon Highschool

10169 Shallow Water Drive, Winter Garden
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