Winter Garden Homes with Community Mailbox Community Features

Winter Garden Homes with Community Mailbox Community Features

**Discover the Charm of Winter Garden, Florida**

Nestled in the heart of Central Florida, Winter Garden is a picturesque city that beautifully blends small-town charm with modern amenities. Known for its vibrant downtown area, Winter Garden boasts a rich history that dates back to the early 1900s, and today, it offers an inviting atmosphere filled with delightful shops, restaurants, and a thriving community spirit. Residents and visitors alike can enjoy the scenic West Orange Trail, perfect for walking, biking, or simply soaking in the stunning Florida sunshine.

When it comes to finding your dream home, Winter Garden presents an array of options, including the sought-after Homes with Community Mailbox. This unique community feature fosters a sense of togetherness among neighbors, encouraging friendly interactions and building lasting relationships. Imagine stepping outside to collect your mail and exchanging pleasantries with those who share your street. It’s the perfect blend of convenience and camaraderie.

The Homes with Community Mailbox not only enhance the neighborhood’s charm but also offer an array of amenities designed for a fulfilling lifestyle. Many of these homes feature spacious layouts, modern designs, and access to community parks and recreational facilities. Whether you’re a first-time homebuyer or looking to downsize, Winter Garden’s real estate market has something for everyone.

With its stunning natural beauty, rich culture, and a strong sense of community, Winter Garden is more than just a place to live—it’s a place to call home. Explore the possibilities and discover why so many are choosing to make Winter Garden their forever home today!

Newest Winter Garden Homes with Community Mailbox Community Features

$265,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
$319,000
2 Beds ⋅ 3 Baths ⋅ Daniels Lndg A-J SubDv. ⋅ 34787 Zip Code
LISTED AT APPRAISED VALUE! Welcome to this beautifully updated townhome in the highly desirable gated community of Daniels Landing in Winter Garden. Combining modern upgrades with an ideal location, this move-in-ready residence offers the perfect blend of style, comfort, and convenience. Step inside to discover an inviting open-concept main level featuring a spacious living room, a well-appointed kitchen with granite countertops, ample cabinetry, a dining area, and a convenient half bath for guests. Luxury wood plank flooring flows throughout the living room and both bedrooms, creating a warm and cohesive feel. Upstairs, you'll find two generously sized primary suites, each complete with walk-in closets and private en-suite bathrooms. The bathrooms were fully renovated in 2025 with designer tile flooring, new vanities, LED mirrors, beautifully tiled showers, new toilets, and contemporary fixtures, creating spa-inspired spaces you'll love. A conveniently located upstairs laundry area adds to the home's thoughtful layout. Extensive recent improvements provide exceptional peace of mind, including a complete HVAC system replacement (2022), new garage door and garage door opener (2025), professionally cleaned air ducts with a UV air purification system (2025), new ceiling fans throughout (2025), and a full suite of brand-new LG stainless steel appliances including the refrigerator, dishwasher, microwave, washer, and dryer (2025). Enjoy Florida living in your private courtyard, accessible from the rear-entry garage, offering a quiet outdoor retreat for relaxing or entertaining. Residents of Daniels Landing enjoy an array of community amenities, including a resort-style pool, fitness center, clubhouse, playground, and gated entry. Ideally situated just minutes from the award-winning Downtown Winter Garden, the West Orange Trail, shopping, dining, major highways, and approximately 20 minutes from Walt Disney World, this exceptional home offers the perfect combination of low-maintenance living and an unbeatable location.

241 Deepcove Road, Winter Garden
$494,890
3 Beds ⋅ 3 Baths ⋅ Parkview At Hamlin SubDv. ⋅ 34787 Zip Code
Under Construction. Under Construction. Ready in November 2026! This new construction, three-story townhome (The Lantana) is a showstopper with its popular farmhouse exterior. This townhome features 3 bedrooms, 2 full bathrooms, a powder room, spanning 1,881 sq. ft. As you enter this home through the 8 ft. entry-door, you are welcomed by your spacious flex space. 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. Your inner gourmet will be 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.

15159 Groveside Road, Winter Garden
$908,142
5 Beds ⋅ 5 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Discover elevated living in this thoughtfully designed home at Northlake at Ovation, offering flexible spaces and curated finishes to fit your everyday lifestyle. From the inviting covered lanai to the spacious loft and soaring ceilings, this floor plan provides room to relax, work, and entertain with ease. Inside, you’ll find a balance of bold and neutral finishes from the AW Collection Rosemary. Design upgrades include 8' interior doors, quartz countertops, tiled backsplash, stainless steel appliances and more. Whether you’re hosting gatherings or enjoying quiet evenings at home, the open layout and versatile rooms adapt to your needs. Perfectly located in Winter Garden near some of Central Florida’s most beloved destinations, this home is just 35 minutes from Orlando International Airport, 15 minutes from world-famous Disney theme parks, and 30minutes from charming Celebration. Residents can also enjoy the charm and rich local history of nearby downtown Winter Garden, known for its vibrant shops, and eateries. Paired with great local schools and a peaceful community setting, this home delivers the ideal blend of comfort, convenience, and Central Florida living. Residents also enjoy a clubhouse, community pool, playground areas and dog park. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17625 Lake Star Road, Winter Garden
$419,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 2 SubDv. ⋅ 34787 Zip Code
Short Sale. ***SHORT SALE***Built in 2024, this like new 2 bedroom plus den, 2 bathroom home offers modern finishes, thoughtful upgrades, and a private setting tucked toward the back of the community with no rear neighbors. The flexible den features French doors, making it ideal for a home office, hobby room, or additional living space. The open concept layout is filled with natural light and centers around a beautifully appointed kitchen with white cabinetry, white Ice subway tile backsplash, white quartz countertops, stainless steel appliances, and a spacious island perfect for everyday living and entertaining. The primary suite features an upgraded walk in shower, while ceiling fans in the living room, both bedrooms, and the den provide added comfort throughout the home. Enjoy Florida living from the covered front porch with space for seating or unwind on the screened lanai overlooking the peaceful backyard with exceptional privacy. The 2 car garage includes two overhead storage racks for added organization. Located just minutes from Walt Disney World, Flamingo Crossings, Horizon West shopping and dining, major roadways, and everyday conveniences, this home combines a desirable location with low maintenance, move in ready living.

13640 Splashing Isla Drive, Winter Garden
$555,000
3 Beds ⋅ 3 Baths ⋅ Watermark Ph 4 SubDv. ⋅ 34787 Zip Code
Welcome to 10439 Austrina Oak Loop, a beautifully upgraded 3-bedroom, 2.5-bath home with over 2,080 square feet of thoughtfully designed living space in the highly sought-after Watermark community. From the moment you step inside, you'll appreciate the luxury vinyl flooring throughout the first floor, upgraded 8-foot interior doors, designer hardware, and abundant natural light that enhances the home's bright, open-concept layout. The spacious main room flows seamlessly into the dining area and gourmet kitchen, creating the perfect space for everyday living and entertaining. The kitchen features stainless steel appliances, upgraded cabinetry lighting above and below the cabinets, modern stairs with wire handrails, and stylish finishes that blend beauty with functionality. Upstairs, a versatile loft provides the ideal space for a home office, media room, fitness area, or playroom. All three bedrooms are conveniently located on the second floor, offering privacy and comfort. The spacious primary suite features an elegant tray ceiling, oversized walk-in closets, and a luxurious ensuite bath with dual vanities, a large walk-in shower, and plenty of natural light. The secondary bathroom also offers dual sinks, providing added convenience for family and guests. The upstairs laundry room is both practical and well-appointed with upgraded cabinetry and a large utility sink. For those who work remotely, the dedicated office area includes hard-wired internet for reliable high-speed connectivity. The oversized two-car garage is equipped with a 240-volt outlet, making it ready for electric vehicle charging. Enjoy the added benefit of a professional installed whole-water treatment system with dual treatment tanks and pre-filter, helping provide cleaner, conditioned water throughout the home while protecting plumbing and appliances. Enjoy relaxing on the inviting covered front porch, and each evening step outside to catch views of the spectacular Magic Kingdom fireworks. Residents of Watermark enjoy exceptional resort-style amenities, including a clubhouse, resort pool, splash pad, fitness center, tennis courts, playgrounds, scenic walking trails, and beautifully maintained green spaces. The home is just minutes from The Mark at Watermark, featuring Starbucks, Walgreens, New York Beer Project, restaurants, and everyday conveniences. You'll also enjoy close proximity to Orange County National Golf Center, Winter Garden Village, Walt Disney World Resort, highly rated local schools, and convenient access to State Road 429. Offering an exceptional combination of premium upgrades, an unbeatable location, and outstanding community amenities, this move-in-ready home presents an incredible opportunity to enjoy the very best of Central Florida living.

10439 Austrina Oak Loop, Winter Garden
$650,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Pointe/Horizon West P SubDv. ⋅ 34787 Zip Code
Great house fronting the park, gym, and community pool. Tons of upgrades inside and out. Beautiful screened pool with motorized shade for privacy on patio. Saltwater pool. Luxury Vinyl Plank throughout the house. NO Carpet! Kitchen has lots of upgrades as well. KitchenAid appliances. Wall oven and cooktop. Samsung refrigerator included. Washer and Dryer also stay! 5 mounted TV's will convey as well! Ring alarm system with cameras as well. Plantation shutters throughout.

14048 Lake Abbotts Drive, Winter Garden
$1,249,990
5 Beds ⋅ 4 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code
Virtually Staged. Modern architecture. Total effortlessness. This five-bedroom residence is a masterclass in high-end finish designs, featuring high ceilings, iron-rod accents, and a dramatic, gallery-inspired aesthetic. At its heart, a chef-caliber kitchen serves as the ultimate hub for refined entertaining. Step into a home where luxury meets thoughtful innovation. This sprawling corner-lot property, crafted by the renowned Meritage Homes, is a rare find that perfectly balances grand proportions with everyday comfort. Boasting five spacious bedrooms, three full baths, and two half baths, the layout is designed for those who love to host and move freely through their space. The heart of the home is an expansive, sun-drenched open floor plan that flows effortlessly toward your own private oasis. Step outside to find a beautiful screened-in pool area, ideal for afternoon swims or evening gatherings without the worry of the elements. What truly sets this residence apart is the commitment to quality and efficiency. Protected by a timeless tile roof, the home features high-energy windows and spray-foam attic insulation, keeping the interior cool. The oversized three-car garage even comes equipped with a Tesla charger, ready for your electric vehicle. From the numerous high-end upgrades found throughout the interior to the curb appeal of its prominent corner position, every detail has been considered. This is more than just a house; it’s a modern, energy-efficient sanctuary built for a lifestyle. The experience extends to a private pool house, complete with a game room and a theater-style loft. Outside, the pool anchors an at home retreat. This is luxury without the logistics. Your residency is entirely turnkey and ready for you to move in.

1734 Amsel Falls Park Terrace, Winter Garden
$830,186
3 Beds ⋅ 3 Baths ⋅ Northlake At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to Northlake at Ovation! This gorgeous new construction home is located in the highly desirable Horizon West area of Winter Garden. This beautiful two story home features 3 bedrooms, 3 baths and flexible loft space. The open kitchen boasts plenty of upgrades from the AW Collection Milan such as beautiful 42 inch cabinets, tiled backsplash, and stainless steel appliances. Large island with upgraded quartz countertops perfect for gatherings that is open to the family room with soaring two story ceiling with plenty of windows bringing in natural light throughout. Main living space features wood look tile flooring and bedrooms with upgraded carpet for comfort, plus 8' interior and exterior doors throughout the home. Enjoy the amenities with a swim in the community pool, clubhouse, shaded playground, and dog park. This home is conveniently located to top rated schools, shopping, grocery stores, Horizon West restaurants, and Walt Disney World. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17631 Lake Star Road, Winter Garden
$199,999
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens SubDv. ⋅ 34787 Zip Code
Welcome to this first floor condo in the heart of Winter Garden! This 2 bedroom, 2 bath unit offers an excellent opportunity for both homeowners and investors. Enjoy the convenience of ground floor living with a private screened in patio, perfect for relaxing with your morning coffee or unwinding after a long day. Inside, you'll find a functional floor plan with a washer and dryer included, making move in even easier. The home is priced to reflect its potential and is ready for your personal touch with fresh paint and new flooring, allowing you to customize the space while adding instant value. Residents enjoy a variety of community amenities, including a swimming pool, basketball court, clubhouse, and community mailbox. The unit also comes with two designated parking spaces for added convenience. Ideally located near shopping, dining, entertainment, and major roadways, this condo offers affordability, convenience, and the opportunity to make it your own in one of Winter Garden's most desirable areas.

93 Windtree Lane Unit 102, Winter Garden
$520,000
3 Beds ⋅ 3 Baths ⋅ Longleaf At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to Longleaf at Oakland by Pulte! Built in 2020, this move-in-ready three-bedroom, 2.5-bath home offers 1,811 square feet of stylish living space featuring brand-new luxury vinyl plank flooring throughout, fresh interior paint, quartz countertops, stainless steel appliances and an open-concept layout designed for comfortable everyday living and effortless entertaining. Located less than five minutes from the new Oakland Town Center, you’ll be close to an exciting new lifestyle destination featuring chef-driven restaurants, boutique shopping, fitness and wellness concepts, medical services, outdoor gathering spaces and everyday conveniences. Historic Downtown Winter Garden, the West Orange Trail and major highways are also just minutes away. Residents of Longleaf at Oakland enjoy a community pool, playground and beautifully maintained green spaces, all within one of West Orange County’s most desirable communities. Don’t miss the opportunity to own this beautifully updated, move-in-ready home in one of Oakland’s most sought-after neighborhoods. Schedule your private showing today!

2766 Bobcat Chase Boulevard, Winter Garden
$1,030,000
4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!

13852 Jomatt Loop, Winter Garden
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