Winter Garden Homes with Community Mailbox Community Features

Winter Garden Homes with Community Mailbox Community Features

Welcome to Winter Garden, Florida—a charming city nestled in the heart of Orange County, where picturesque landscapes meet vibrant community life. Known for its rich history and a delightful blend of small-town charm and modern convenience, Winter Garden offers residents an idyllic lifestyle. With its historic downtown brimming with boutique shops, delightful eateries, and a lively farmers' market, you’ll find plenty of opportunities to engage with your neighbors and enjoy the local culture.

One of the standout features of homes in Winter Garden is the Community Mailbox, which fosters a sense of unity among residents. This thoughtfully designed community feature encourages social interaction and creates a welcoming atmosphere as neighbors gather to collect their mail. Imagine stepping outside your door to greet friendly faces and share a smile while picking up your letters—a simple pleasure that enhances the sense of belonging in this close-knit community.

In addition to the Community Mailbox, Winter Garden boasts an array of amenities that cater to an active lifestyle. With beautiful parks, scenic trails, and recreational facilities, outdoor enthusiasts will find endless opportunities to explore and enjoy nature. The city also hosts various community events throughout the year, from festivals to outdoor concerts, ensuring there’s always something happening to bring residents together.

Whether you’re looking to settle down in a cozy single-family home or a modern townhouse, Winter Garden offers a diverse selection of properties that cater to every taste. Embrace the warmth and charm of Winter Garden, where your dream home awaits in a community that feels like family.

Newest Winter Garden Homes with Community Mailbox Community Features

14747 Field Daisy Drive, Winter Garden
$573,147
3 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Close to Amenities | Gas Range | 1st Floor Guest Suite. New Construction - December Completion! Welcome to the Newberry at 14747 Field Daisy Drive in Harvest at Ovation! This thoughtfully designed two-story home offers three bedrooms, three-and-a-half baths, and inviting spaces that blend comfort with everyday convenience. The bright kitchen with a spacious island opens to the casual dining area and great room, creating a warm and welcoming setting for gathering with family and friends. A first-floor secondary bedroom with an ensuite full bath is perfect for guests, while upstairs, the private primary suite provides a peaceful retreat with a generous walk-in closet and well-appointed bath. A versatile loft adds flexible living space, and the covered lanai is ideal for relaxing or enjoying time outdoors. Complete with a two-car garage, this home is as functional as it is charming. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: Shower in place of tub at secondary bath, 8' interior doors, pre-plumb for future laundry tub, LVP flooring throughout, and whole house blinds. Photos are for representative purposes only. MLS#O6449322

14747 Field Daisy Drive, Winter Garden
14795 Field Daisy Drive, Winter Garden
$609,481
4 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Popular Plan | Flat Lot. New Construction - December Completion! Welcome to the Ashwood at 14795 Field Daisy Drive in Harvest at Ovation! This beautifully designed two-story home offers a bright, open-concept layout perfect for everyday living and entertaining. The first floor features a spacious great room that flows into the kitchen and dining area, along with a private study and convenient half bathroom. The second floor includes the primary suite with a generous walk-in closet and bathroom, two secondary bedrooms, full bathroom, and a laundry room. Enjoy outdoor living on the lanai and the convenience of a detached two-car garage with a large game room above with a full bathroom providing flexible space for relaxing or hosting guests. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: wet bar at game room, pre-plumbed for future laundry sink, gas appliance package, quartz countertops, and refrigerator. Photos are for representative purposes only. MLS#O6449311

14795 Field Daisy Drive, Winter Garden
14775 Field Daisy Drive, Winter Garden
$635,572
4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Game Room | Balcony | Close to Amenities | Gas Range. New Construction - November Completion! Welcome to the Newberry at 14775 Field Daisy Drive in Harvest at Ovation! This inviting two-story home offers an open-concept design with a spacious great room that flows seamlessly into the casual dining area and kitchen, creating the perfect space for gathering and entertaining. A secondary bedroom with a nearby bathroom is conveniently located on the first floor, while upstairs features the private primary suite, two additional bedrooms, full bathroom, a game room, and laundry room. Relax outdoors on the lanai and enjoy the convenience of a detached two-car garage. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails, all in a highly coveted location. Additional Highlights Include: Wet bar at game room, whole house 8' interior doors, 42" upper kitchen cabinets, quartz counter tops and crown molding package at kitchen. Photos are for representative purposes only. MLS# O6449282

14775 Field Daisy Drive, Winter Garden
14779 Field Daisy Drive, Winter Garden
$625,000
4 Beds ⋅ 5 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: Game Room | Close to Amenities | 1st Floor Guest Suite. New Construction - November Completion! Welcome to the Newberry at 14779 Field Daisy Drive in Harvest at Ovation! Step into this thoughtfully designed four-bedroom home featuring flexible living spaces and inviting areas to gather. The open-concept main level showcases a bright kitchen with a large island overlooking the casual dining area and spacious great room, creating the perfect setting for everyday living and entertaining. A secondary bedroom and full bath on the main floor offer flexibility for guests, a home office, or multi-generational living. Upstairs, the private primary suite provides a relaxing retreat, while two additional bedrooms, a versatile game room, and convenient laundry room offer plenty of space to fit your lifestyle. Enjoy seamless indoor-outdoor living with a covered lanai that extends your living space year-round. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: 8' interior doors, wet bar at game room, shower in place of tub at bath 2, luxury vinyl plank flooring and quartz countertops. Photos are for representative purposes only. MLS#O6449273

14779 Field Daisy Drive, Winter Garden
13037 Serene Glade Road, Winter Garden
$539,990
3 Beds ⋅ 3 Baths ⋅ Serenade At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Brand New Home in Winter Garden, Florida | The Brantley Model Welcome to the stunning Brantley Model, a brand-new bungalow-style single-family home in desirable Winter Garden, Florida, where modern luxury meets timeless charm. Offering 1,836 square feet of thoughtfully designed living space, this beautiful 3-bedroom, 2.5-bath home features an inviting open-concept layout, oversized windows, and abundant natural light throughout. The heart of the home is the beautifully upgraded gourmet kitchen, showcasing premium finishes, elegant quartz countertops, custom cabinetry, and stainless steel appliances. Perfect for entertaining or everyday living, the kitchen flows seamlessly into the bright and spacious living areas, creating a warm and welcoming atmosphere. Step outside through the charming breezeway to your private paver courtyard—an ideal setting for al fresco dining, morning coffee, or relaxing evenings outdoors. Additional highlights include a convenient two-car garage, stylish architectural details, and a thoughtfully designed layout that balances comfort, functionality, and sophistication. With its blend of contemporary upgrades, classic bungalow character, and seamless indoor-outdoor living, the Brantley Model offers an exceptional opportunity to enjoy the best of new construction in Winter Garden. Experience the perfect place to call home!

13037 Serene Glade Road, Winter Garden
13013 Serene Glade Road, Winter Garden
$529,990
3 Beds ⋅ 3 Baths ⋅ Serenade At Ovation SubDv. ⋅ 34787 Zip Code
Welcome to the stunning Brantley Model, a brand-new bungalow-style single-family home in desirable Winter Garden, Florida, where modern luxury meets timeless charm. Offering 1,836 square feet of thoughtfully designed living space, this beautiful 3-bedroom, 2.5-bath home features an inviting open-concept layout, oversized windows, and abundant natural light throughout. The heart of the home is the beautifully upgraded gourmet kitchen, showcasing premium finishes, elegant quartz countertops, custom cabinetry, and stainless steel appliances. Perfect for entertaining or everyday living, the kitchen flows seamlessly into the bright and spacious living areas, creating a warm and welcoming atmosphere. Step outside through the charming breezeway to your private paver courtyard—an ideal setting for al fresco dining, morning coffee, or relaxing evenings outdoors. Additional highlights include a convenient two-car garage, stylish architectural details, and a thoughtfully designed layout that balances comfort, functionality, and sophistication. With its blend of contemporary upgrades, classic bungalow character, and seamless indoor-outdoor living, the Brantley Model offers an exceptional opportunity to enjoy the best of new construction in Winter Garden. Experience the perfect place to call home!

13013 Serene Glade Road, Winter Garden
341 Southern Pecan Circle Unit 202, Winter Garden
$220,000
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
WINTER GARDEN GEM! NEW KITCHEN • NEW APPLIANCES • NO CARPET • PRIVATE GARAGE • RESORT-STYLE AMENITIES! Welcome to 341 Southern Pecan Circle, Unit 202, Winter Garden, FL 34787! Discover this beautifully updated, move-in-ready 1-bedroom, 1-bathroom condo featuring modern upgrades, open-concept living, a private garage, and outstanding resort-style community amenities in desirable Winter Garden, Central Florida! Step inside to enjoy bright, inviting living and dining areas filled with natural light, fresh interior paint, and NO CARPET THROUGHOUT! Attractive wood-look flooring enhances the living areas and bedroom, complemented by easy-to-maintain tile flooring in the kitchen and bathroom. The NEW KITCHEN showcases beautiful cabinetry, attractive countertops, a spacious breakfast bar, stainless steel appliances, and a NEW REFRIGERATOR AND MICROWAVE! The open layout provides an inviting space for everyday living and entertaining. The spacious bedroom offers generous closet space, while the UPDATED BATHROOM features attractive tile finishes and a convenient vanity. Additional conveniences include an IN-UNIT WASHER AND DRYER and a PRIVATE GARAGE for parking and extra storage. ENJOY RESORT-STYLE LIVING! This amenity-rich community features a sparkling swimming pool, fitness center (gym), basketball court, tennis courts, sand volleyball court, playground, and car wash station. The COMMUNITY CLUBHOUSE also offers a community kitchen, computer room, nursery room, and meeting room, providing excellent spaces for recreation, convenience, and community activities. DESIRABLE WINTER GARDEN LOCATION! Enjoy convenient access to shopping, dining, entertainment, parks, major roadways, and the greater Orlando area. IDEAL FOR LOW-MAINTENANCE LIVING OR INVESTMENT! Whether you're seeking a primary residence, seasonal retreat, convenient home for work or studies, or a potential rental investment, this updated Winter Garden condo offers comfort, functionality, and lifestyle amenities. Rental opportunities are subject to association rules and restrictions. NEW KITCHEN • NEW APPLIANCES • UPDATED BATHROOM • NO CARPET • PRIVATE GARAGE • IN-UNIT LAUNDRY • RESORT-STYLE AMENITIES! SCHEDULE YOUR PRIVATE SHOWING TODAY!

341 Southern Pecan Circle Unit 202, Winter Garden
2107 Gopher Tortoise Terrace, Oakland
$364,900
2 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code
Beautifully maintained fully furnished six-year-old townhome in the charming town of Oakland! This 2-bedroom, 2.5-bath home features a covered front porch, abundant natural light, and thoughtful upgrades throughout. The open great room welcomes you with Shaw luxury vinyl tile flooring, neutral colors, recessed LED lighting, and dual-pane Low-E windows with cordless faux wood blinds. The kitchen features 42-inch cabinetry, granite countertops, a gray subway tile backsplash, and a spacious island with upgraded pendant lighting and a large undermount sink. Appliances include a Whirlpool Gold microwave, range, and dishwasher, plus an LG French-door refrigerator. A generous pantry with a California Closets shelving system provides exceptional organization. The adjoining dining area features upgraded lighting and access to a private 19-by-15-foot paver courtyard through a full-glass door with built-in blinds. A convenient desk nook with granite countertops, drawers, and cabinetry offers space to work from home. The first-floor laundry room includes a California Closets laundry station and access to ample storage beneath the stairs. A half bath is conveniently located off the stair landing. Upstairs, both spacious bedrooms feature walk-in closets and private bathrooms. The primary suite offers a beautifully organized California Closets system with a built-in vanity. Its ensuite bath includes dual sinks, granite countertops, Moen faucets, a private water closet, and a tiled shower with decorative accents, frameless glass, and an upgraded showerhead. The second bedroom’s bathroom features granite countertops and a tiled tub/shower combination with an accent inlay. The private courtyard connects to a two-car garage with epoxy flooring and a Bluetooth-enabled opener. Additional features include gutters, a Taexx built-in pest control system, Nest thermostat, Ring security system and doorbell, Alexa-compatible front porch lighting, and prewiring for ceiling fans in the great room and bedrooms. Enjoy community walking paths, a playground, and a pool, with lawn care included in the HOA. Conveniently located near the West Orange Trail, downtown Winter Garden, downtown Clermont, Florida’s Turnpike, and Winter Garden Village. Bring your pups—this community has no dog breed restrictions!

2107 Gopher Tortoise Terrace, Oakland
17126 Quicksilver Avenue, Winter Garden
$525,000
4 Beds ⋅ 3 Baths ⋅ Waterside On Johns Lake - Phase 2c SubDv. ⋅ 34787 Zip Code
Welcome home to this beautifully cared-for 4-bedroom, 3-bathroom home in the welcoming Waterside community! Built in 2022, the thoughtfully designed floor plan, spacious backyard, and wonderful neighborhood amenities combine to create the perfect blend of comfort, functionality, and everyday family living. Inside, the OPEN-CONCEPT living space flows effortlessly into the kitchen, creating a comfortable gathering place for family time, entertaining, and everything in between. The kitchen features beautiful Silestone QUARTZ COUNTERTOPS, stylish gray cabinetry, and stainless steel appliances. The spacious primary suite offers a HUGE WALK-IN CLOSET, while the primary bathroom features a double-sink vanity and large WALK-IN TILED SHOWER. A bedroom conveniently located downstairs adds incredible flexibility and can easily serve as a guest room, home office, playroom, or a space for visiting family and friends. Throughout the home, you'll find thoughtful upgrades including plantation shutters, built-in features, 9-foot ceilings, and a beautiful wrought-iron stair railing. Situated on an OVERSIZED CORNER LOT, the property features a large fenced-in backyard with plenty of room to play, relax, or gather with friends. The back paver patio is perfect for weekend barbecues and outdoor entertaining, while the covered front porch provides a welcoming spot to enjoy your morning coffee or unwind at the end of the day. Waterside Residents enjoy access to a community clubhouse, pool, fitness center, playgrounds, park, and a dock on Johns Lake. With seasonal community events and monthly food truck nights, there are plenty of opportunities to get to know your neighbors and enjoy everything the community has to offer. Conveniently located near Downtown Winter Garden, Hamlin, and Walt Disney World, you'll be close to a fantastic selection of restaurants, shops, and entertainment. Easy access to FL-429 and the Florida Turnpike makes commuting and exploring Central Florida a breeze. Come see why this home and community are such a wonderful place to put down roots, make memories, and call home!

17126 Quicksilver Avenue, Winter Garden
11079 Sound Shore Drive, Winter Garden
$825,000
5 Beds ⋅ 5 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Welcome to your dream home that checks ALL the boxes! This 2023 built block on block construction popular Torrey floor plan has everything you will need with 5 bedrooms, 4 and a half baths, SOLAR panels included in sale price, a formal dining room, DOWNSTAIRS guest room with attached full bathroom, large lanai, bonus room to create a second living area or playroom, gourmet kitchen, and fenced in yard with no direct rear neighbor. This home is perfect for entertaining, having an open concept layout with a kitchen/living open space, while also boasting classic charm with a formal dining room off the kitchen. The stunning kitchen features a built in wall oven and microwave, cooktop with matching stainless steel hood, and large butler’s pantry. The formal dining room could be used for it’s intended purpose or it can easily be closed in with French doors to create a home office, playroom, formal sitting room, or exercise room! Upstairs you will find the remaining 4 bedrooms, 3 full bathrooms, and huge bonus room. The master retreat is true luxury with a soaking tub and fireworks view from the master bedroom! Currently, the downstairs guest room is being used as a dual purpose room with a desk to be used as an office but also has a custom, built in murphy bed that can be used when you have guests in town. This home features a huge 28x10 covered lanai perfect for dining a la fresca and enjoying the peaceful dry retention pond that this home backs up to that is fleeting with wildlife including many different bird species, hawks, and sand cranes. The spacious, fenced in yard is perfect for your furry friends or children. Located in the sought after Horizon West area zoned for “A” schools including Atwater Bay Elementary, Water Spring Middle School, and Horizon West High. Along with its amazing location, the Waterleigh community also offers a beautiful clubhouse with resort style pool, miniature golf course, beach volleyball, grills, picnic areas, fishing pier on the lake, biking trails, walking trails, tennis courts, pickleball, and "bark parks" for your furry friends; making it a perfect place for the family lifestyle. The clubhouse has a robust calendar of events for all ages such as Mahjong classes, exercise classes, kids dance lessons, beer tasting events, and many more! Living in the gorgeous Waterleigh community surrounded by ponds and lakes is all about nature and outdoor living! Love the outdoors but don't like mowing the lawn and weeding the shrubs? No problem, the HOA takes care of that for you here. Love the Florida golf cart life? You can take your street legal golf to the community pool, and join the neighbors for lots of fun, holiday golf cart parades!! Within minutes you have loads of shopping and activities including Hamlin center, Flamingo Crossings shopping center, and Disney parks and resorts! All you have to do is move in and start enjoying the lifestyle Waterleigh has to offer! Lastly, this well loved house has all the upgrades including: solar panels (sellers will pay off the remaining loan balance at closing), telsa EV charger, motorized blinds in all 4 bedrooms upstairs, (2) alarm.com security systems, 3 ring cameras, 2 garage ceiling storage racks, and built in attachments in the garage for a kids ninja warrior style obstacle course. Green aspects: solar panels and reclaimed water for watering the grass.

11079 Sound Shore Drive, Winter Garden
12355 Bracco Street, Winter Garden
$565,000
4 Beds ⋅ 3 Baths ⋅ Highland Rdg Ph 2 SubDv. ⋅ 34787 Zip Code
Virtually Staged. STUNNING 2024-BUILT HOME ON AN OVERSIZED LOT IN ONE OF WINTER GARDEN’S DESIRABLE GATED COMMUNITIES! Why wait to build when you can enjoy the benefits of nearly new construction in this beautiful 4-BEDROOM, 3-BATHROOM HOME offering modern living, exceptional curb appeal, and an OVERSIZED LOT that provides extra space to enjoy the Florida lifestyle! Built in 2024, this impressive home offers the comfort, style, and peace of mind that come with newer construction. With four spacious bedrooms and three full bathrooms, there is plenty of room for comfortable everyday living, entertaining guests, or creating the perfect home office. The oversized lot is a standout feature, offering additional outdoor space with endless possibilities for entertaining, relaxing, gardening, or creating your own backyard paradise! LOCATION, LOCATION, LOCATION! Welcome to beautiful WINTER GARDEN, one of Central Florida’s most sought-after destinations! Discover why so many people love calling this incredible area home. Enjoy the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for its incredible restaurants, boutique shopping, lively farmers market, and vibrant community atmosphere. Explore the scenic WEST ORANGE TRAIL, enjoy nearby parks and recreational opportunities, and take advantage of fantastic shopping, dining, entertainment, and convenient access to Orlando’s world-famous attractions! RESORT-STYLE COMMUNITY AMENITIES WITHOUT THE HIGH HOA FEES! Enjoy the added appeal of a GATED COMMUNITY featuring a beautiful COMMUNITY SWIMMING POOL and PLAYGROUND, all while benefiting from LOW HOA FEES! It’s a wonderful combination of community amenities, convenience, and affordability. With its 2024 CONSTRUCTION, FOUR BEDROOMS, THREE FULL BATHROOMS, OVERSIZED LOT, GATED COMMUNITY, COMMUNITY POOL, PLAYGROUND, AND PRIME WINTER GARDEN LOCATION, this home offers an incredible opportunity to enjoy the Florida lifestyle! DON’T MISS YOUR OPPORTUNITY TO CALL THIS BEAUTIFUL PROPERTY HOME! SCHEDULE YOUR PRIVATE SHOWING TODAY AND DISCOVER EVERYTHING THIS EXCEPTIONAL HOME AND COMMUNITY HAVE TO OFFER!

12355 Bracco Street, Winter Garden
1396 Roxy Lane, Winter Garden
$499,900
4 Beds ⋅ 3 Baths ⋅ Waterside/Johns Lake Ph 2c SubDv. ⋅ 34787 Zip Code
Welcome home to Waterside on Johns Lake, a highly sought-after community in Winter Garden! This 4-bedroom, 3-full-bath, 2,030 sq. ft. single-family home offers an open-concept floor plan with a great blend of functionality and living space. The first floor features the great room that flows seamlessly into the dining area and kitchen, which features 42-inch grey shaker cabinetry, quartz countertops, and a pantry. Also on the first floor is a full bathroom and a bedroom, making it ideal for guests, a home office, or flexible living needs. A convenient mudroom with generous storage provides additional functionality. Step outside to a private patio with a dedicated seating and entertaining area, along with a large fenced-in side yard. The rear of the property features a detached 2-car garage and a private driveway with additional parking for two vehicles. Upstairs, the split-bedroom layout provides privacy and flexibility. The spacious primary suite features an oversized bedroom, walk-in closet, and private en-suite bathroom. Two additional bedrooms, a third full bathroom, and a dedicated laundry room complete the second floor. The location is hard to beat, with convenient access to Winter Garden Village, Hamlin, Horizon West, Downtown Winter Garden, and SR-429. Enjoy an easy drive to Central Florida's major attractions, including Disney, SeaWorld, and Universal Studios, as well as an abundance of shopping, dining, and entertainment options. Waterside on Johns Lake features resort-style amenities including a community pool and clubhouse, playground, park, fitness center, and community dock on Johns Lake. The home is also zoned for highly regarded A-rated schools, including Hamlin Elementary, Hamlin Middle, and West Orange High.

1396 Roxy Lane, Winter Garden
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