Winter Garden/Oakland Homes with Community Mailbox Community Features

Winter Garden/Oakland Homes with Community Mailbox Community Features

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area seamlessly blends the charm of small-town living with the conveniences of modern life, making it an ideal destination for families, retirees, and everyone in between.

Winter Garden is renowned for its picturesque streets lined with historic buildings, quaint shops, and delightful eateries, all set against the backdrop of lush greenery and scenic lakes. The nearby Oakland offers a serene atmosphere, boasting beautiful parks and nature trails that invite residents to explore the great outdoors. With its close-knit community vibe, Winter Garden and Oakland provide a warm and welcoming environment where neighbors become friends.

One of the standout features of this region is the Homes with Community Mailbox community. These thoughtfully designed homes offer not only a place to live but also a sense of belonging. Residents enjoy the convenience of a centralized mailbox, fostering social interactions and a sense of community. Imagine gathering with neighbors for a friendly chat while collecting your mail or exchanging pleasantries during your daily stroll.

In addition to the charming homes, the community features a range of amenities designed to enhance your lifestyle. From beautifully landscaped parks to recreational facilities, there’s always something to do. Whether you’re enjoying a sunny afternoon at the local playground or participating in community events, the sense of camaraderie is palpable.

Explore the delightful neighborhoods of Winter Garden and Oakland, where your dream home awaits amidst a vibrant community and a wealth of amenities!

Newest Winter Garden/Oakland Homes with Community Mailbox Community Features

$675,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
Seller may consider buyer concessions if made in an offer ~ LIKE-NEW LIVING in one of Winter Garden’s most sought-after communities! Just four years old, this beautiful DAVID WEEKLEY SUMMERTON MODEL is located in McKinnon Square within award-winning Oakland Park – and the GOLF CART IS INCLUDED! High ceilings, abundant natural light and an OPEN CONCEPT design create a bright, welcoming interior made for everyday living and entertaining. At the heart of the home, the GOURMET CHEF’S KITCHEN flows seamlessly into the main living and dining spaces, while the inviting FRONT PORCH adds to the neighborhood feel Oakland Park is known for. All of the bedrooms are upstairs along with a versatile BONUS/LOFT offering endless possibilities as a home office, playroom, media space or second living area. Life here extends well beyond the front door – Oakland Park is a GOLF CART-FRIENDLY COMMUNITY offering a clubhouse, COMMUNITY POOLS, parks, playgrounds, a dog park and recreational amenities, plus easy access to the WEST ORANGE TRAIL and LAKE APOPKA. Cruise by golf cart to HISTORIC DOWNTOWN WINTER GARDEN for award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, seasonal festivals and the popular Winter Garden Farmers Market. Everyday convenience is equally impressive, with the elementary school approximately .5 miles away, middle school 1.1 miles, high school 3 miles and Orlando Health Hospital approximately 1.8 miles away. Hamlin Town Center, SR-429, SR-50 and Florida’s Turnpike are easily accessible, with shopping, dining, Disney and Central Florida attractions within reach. MOVE-IN READY, nearly new and complete with a golf cart, this Oakland Park home delivers the lifestyle that makes Winter Garden such a desirable place to call HOME!

923 Colie Alley, Winter Garden
$1,085,669
5 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12528 Gold Honeysuckle Street, Winter Garden
$475,000
3 Beds ⋅ 3 Baths ⋅ Hickory Hammock Ph 1c SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome Home to 15163 Orange Harvest Drive! YOUR oportunity to live in this incredible neighborhood, is HERE! Move-in ready and beautifully maintained, this townhome offers 3 bedrooms, 2.5 baths, and a bright, open layout perfect for modern living. A paver driveway and charming stucco exterior with mature landscaping set the tone before you even step inside. The main level features a spacious open-concept living and dining area with tile flooring throughout. Sliding glass doors lead out to a private patio, offering a peaceful spot to unwind while overlooking green common space. The kitchen is a standout, showcasing rich espresso cabinetry, gleaming granite countertops, a designer mosaic tile backsplash, stainless steel appliances, and a large island with pendant lighting — ideal for entertaining or casual family meals. Upstairs, the generously sized primary suite includes plush carpet and an en-suite bath with dual sinks, a walk-in shower, and a linen closet. A second full bath serves the additional bedrooms with a dual-sink vanity and a tub/shower combo, and a convenient half bath is located on the main level for guests. As part of a sought-after community, residents enjoy resort-style amenities including a sparkling community pool, tennis courts, a playground, and scenic lakefront views — all just minutes from Winter Garden's shops, dining, and amazing schools. Don't miss your chance to own this stylish, low-maintenance townhome in one of Winter Garden's most desirable communities!

15613 Orange Harvest Loop, Winter Garden
$359,999
3 Beds ⋅ 3 Baths ⋅ Orchard SubDv. ⋅ 34787 Zip Code
Some photos are Virtually Staged. WELCOME to a HOME that truly stands out in THE ORCHARD, a desirable GATED COMMUNITY in WINTER GARDEN! This beautifully updated 3-BEDROOM, 2.5-BATHROOM TOWNHOME is perfectly positioned with NO REAR NEIGHBORS and a BEAUTIFUL OPEN GREEN SPACE BEHIND THE HOME, offering a peaceful and private setting. From the moment you arrive, the inviting PRIVATE ENTRYWAY and spacious ATTACHED 2-CAR GARAGE set the tone for the comfort and convenience this home offers. Step inside to discover NO CARPET ON THE FIRST FLOOR, UPDATED LAMINATE FLOORING, and numerous recent updates throughout. The home features NEW LIGHT FIXTURES AND CEILING FANS (2026), NEW FAUCETS (2026), and NEW CARPET UPSTAIRS (2026). Major systems have also been thoughtfully updated, including a NEW HVAC SYSTEM (2025) and ROOF (2020). The WASHER AND DRYER (2024) add even more value and convenience. The open-concept main living area seamlessly connects the living room, dining area, and kitchen, creating a warm and welcoming space for both everyday living and entertaining. The kitchen features GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, ABUNDANT CABINETRY, a LARGE WALK-IN PANTRY, and a BREAKFAST BAR WITH PENDANT LIGHTING. A versatile FLEX ROOM just off the main living area provides endless possibilities and can easily serve as a HOME OFFICE, PLAYROOM, EXERCISE ROOM, OR ADDITIONAL SITTING AREA. A convenient HALF BATH WITH UPDATED FIXTURES, large storage closet, and direct access to the garage complete the first floor. A DEDICATED LAUNDRY AREA adds even more convenience to the home’s thoughtful design. From the dining area, sliding glass doors open to the PEACEFUL BACKYARD SETTING, where you can relax and enjoy the expansive green space and the added privacy of NO REAR NEIGHBORS. Upstairs, the NEW CARPET INSTALLED IN 2026 continues into the spacious loft, currently used as an office and complemented by additional cabinetry. The generous PRIMARY SUITE features a MASSIVE WALK-IN CLOSET WITH A WINDOW and a private ensuite bathroom offering DUAL SINKS, a STANDING SHOWER, SEPARATE JETTED SOAKING TUB, and PRIVATE WATER CLOSET. Two additional bedrooms are thoughtfully located on the opposite side of the primary suite and share a full bathroom featuring a TUB AND SHOWER COMBINATION. The HOA COVERS THE EXTERIOR OF THE HOME, LAWN MAINTENANCE, AND COMMON AREAS, providing added convenience and peace of mind. Residents of THE ORCHARD enjoy GATED SECURITY, a TRANQUIL COMMUNITY POOL, and PLAYGROUND, all in a prime WINTER GARDEN LOCATION just minutes from shopping, dining, top-rated schools, and the charm of DOWNTOWN WINTER GARDEN. TASTEFULLY UPDATED, WELL-MAINTAINED, AND MOVE-IN READY, this townhome offers an exceptional combination of STYLE, COMFORT, PRIVACY, AND CONVENIENCE, with many of the major updates already completed for you. Come see why you will love calling THE ORCHARD HOME!

242 Winter Nellis Circle, Winter Garden
$514,900
4 Beds ⋅ 3 Baths ⋅ Summerlake Grvs SubDv. ⋅ 34787 Zip Code
Virtually Staged. ~Seller may consider buyer concessions if made in an offer~Perfectly situated in sought-after Summerlake Groves of Winter Garden, this BEAUTIFULLY MAINTAINED 4-bedroom, 2.5-bath two-story home offers a light and bright OPEN CONCEPT floor plan, over 2,000 SQUARE FEET of living space, a convenient rear-entry garage and the peace of mind that comes with a home built in 2018. MOVE-IN READY and thoughtfully designed for comfortable family living, this home combines everyday functionality with the lifestyle that makes Winter Garden such a desirable place to call HOME. Step inside to find easy-care CERAMIC TILE FLOORS throughout the main living areas and an inviting flow from the spacious Living Room into the Kitchen and Dining area. An abundance of windows fills the Living Room with NATURAL LIGHT, while the open sight lines make gathering with family or entertaining friends effortless. At the heart of the home, the Kitchen overlooks the living space and features GRANITE COUNTERTOPS, stainless steel appliances, a closet pantry and a generous ISLAND with BREAKFAST BAR SEATING and room for counter-height stools. Just beyond, the bright Dining area offers sliding glass door access to the COVERED BRICK-PAVER PATIO, creating an easy transition for morning coffee, weekend cookouts or relaxing outdoors. Upstairs, the PLUSH CARPETED BEDROOMS provide a comfortable retreat away from the main living spaces. The spacious Primary Suite features a decorative TRAY CEILING, DUAL WALK-IN CLOSETS and a private en-suite bath with dual sinks, STEP-IN SHOWER and private WATER CLOSET. Three additional Bedrooms offer plenty of room for family, guests, a home office or hobbies, with some Bedrooms featuring their own WALK-IN CLOSETS. A second Full Bath has been recently retiled, and the conveniently located second-floor Laundry Room comes with a UTILITY TUB and includes the WASHER and DRYER. Outside, the BRICK-PAVER DRIVEWAY and REAR-ENTRY GARAGE add curb appeal while keeping the front of the home welcoming and attractive. Summerlake Groves offers a wonderful FAMILY-FRIENDLY atmosphere with a LOW HOA and amenities designed for enjoying the Florida lifestyle, including a clubhouse, RESORT-STYLE POOL, playground, dog park and TENNIS COURTS. Community events and SEASONAL FESTIVITIES create even more opportunities to get to know your neighbors and enjoy where you live.The Winter Garden location is hard to beat, with DISNEY WORLD just minutes away and HAMLIN TOWN CENTER nearby for shopping, dining and everyday conveniences. Spend the weekend exploring local parks, enjoying the WEST ORANGE TRAIL, grabbing dinner in Hamlin or heading to the nearby attractions. Zoned for EXCELLENT SCHOOLS and surrounded by the shopping, dining, recreation and entertainment that make Winter Garden so popular, this home provides the ideal combination of comfort, community and convenience. Well maintained, MOVE-IN READY, NEWER CONSTRUCTION and perfectly positioned in one of Winter Garden’s most sought-after areas — this is the one you’ve been waiting for! Call today to schedule your private showing and make Summerlake Groves your next HOME.

8016 Sweet Orange Avenue, Winter Garden
$2,600,000
6 Beds ⋅ 6 Baths ⋅ Summerlake Pd Ph 3a SubDv. ⋅ 34787 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 7693 Green Mountain Way in Winter Garden, an impressive two-story lakefront home offering 6 bedrooms, 6 bathrooms, dual primary suites, a spacious loft, balcony, and multiple indoor and outdoor living areas. Designed to accommodate both everyday living and large-scale entertaining, this expansive residence combines flexible living spaces with standout waterfront amenities and scenic lake views. The interior provides an abundance of space across two levels, highlighted by two primary bedrooms that offer added flexibility for multigenerational households, extended guests, or those who simply prefer multiple private retreats. Four additional bedrooms and six full bathrooms provide generous accommodations throughout the home. A large loft adds another dedicated living area that can easily function as a media room, game room, secondary family room, or entertainment space. The balcony extends the living area outdoors and provides another inviting place to unwind while taking in the surrounding views. Multiple gathering areas throughout the home allow plenty of room for entertaining while still providing separation and privacy when desired. The outdoor spaces are designed to make the most of the home's scenic lakefront setting. A welcoming front porch adds curb appeal, while the rear of the home opens to a covered patio, spacious deck, and outdoor kitchen, creating a well-equipped setting for dining, grilling, and entertaining. The centerpiece is the in-ground infinity pool and spa overlooking the lake, where the water's edge blends beautifully with the waterfront backdrop. With dedicated areas for cooking, lounging, swimming, and gathering, the combination of the outdoor kitchen, covered patio, deck, infinity pool, spa, and expansive lake views creates a resort-inspired outdoor retreat ideal for both everyday relaxation and entertaining. Situated in Winter Garden, the property offers access to a vibrant Central Florida community known for its parks, recreational opportunities, shopping, dining, and convenient connections to major roadways and Orlando-area destinations. With six bedrooms, dual primary suites, six bathrooms, a loft, balcony, expansive outdoor living areas, and a lakefront infinity pool and spa, 7693 Green Mountain Way delivers exceptional space, flexibility, and waterfront living in one impressive property

7693 Green Mountain Way, Winter Garden
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Hull Island At Oakland SubDv. ⋅ 34787 Zip Code
Welcome to this extraordinary custom lakefront estate offering breathtaking views of Lake Apopka and the ultimate Florida waterfront lifestyle. Designed with luxury and functionality in mind, this one-of-a-kind home showcases premium upgrades, exceptional craftsmanship, and direct lake access. The heart of the home is a chef-inspired kitchen featuring a natural gas cooktop, double ovens, expansive center island, abundant counter space, separate breakfast dinette, and a custom walk-in pantry with floor-to-ceiling shelving. The kitchen opens seamlessly to the spacious family room with soaring 12-foot ceilings and triple sliding glass doors that frame spectacular lake views and fill the home with natural light. Step outside to your private waterfront oasis where a covered, screened lanai overlooks professionally landscaped grounds and unforgettable sunsets. The impressive 20' x 60' brick paver patio leads to a private dock with an electric covered boat lift, providing direct access to Lake Apopka. Enjoy fishing from your dock, boating the scenic Harris Chain of Lakes via the Apopka-Beauclair Canal, or spending the day exploring the waterfront restaurants, shops, and attractions of historic downtown Mount Dora and Tavares. The thoughtfully designed floor plan includes a formal dining room with soaring ceilings and a private office with double doors, ideal for working from home. The luxurious primary suite is a true retreat with panoramic lake views, spa-inspired bath featuring a frameless floor-to-ceiling tiled double shower with dual shower heads and built-in bench, soaking tub, dual vanities, and custom walk-in closets. A hidden Murphy door provides private access to two secondary bedrooms and a full bath, creating the perfect guest or family wing. The oversized fourth bedroom offers an ensuite bath and walk-in closet, ideal for guests or multigenerational living. Additional premium features include a 24kW natural gas whole-house generator, electric vehicle charging station, water softener, security system, surround sound, insulated garage doors and ceiling, garage utility sink, overhead storage, and a spacious laundry room with built-in cabinetry, extensive counter space, and utility sink. The oversized three-car garage and expansive six-car brick paver driveway provide ample parking and storage. Located in the sought-after gated community of Hull Island, residents enjoy resort-style amenities including a community pool, gazebo, playground, bark park, and exclusive private access to the 150-acre Oakland Nature Preserve with miles of scenic trails. Nestled in the charming Town of Oakland, this exceptional home is just minutes from Winter Garden Village, historic Downtown Winter Garden, the award-winning Winter Garden Farmers Market, the West Orange Trail, Downtown Clermont, shopping, dining, major hospitals, Orlando's world-famous attractions, Orlando International Airport, and major highways. Florida's beautiful east and west coast beaches are approximately one hour away.

1112 Hull Island Drive, Oakland
$909,990
5 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12529 Gold Honeysuckle Street, Winter Garden
$834,990
4 Beds ⋅ 3 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12523 Gold Honeysuckle Street, Winter Garden
$230,000
2 Beds ⋅ 2 Baths ⋅ Windtree Gardens Condo Ph 01 SubDv. ⋅ 34787 Zip Code
Welcome home to this bright, beautifully maintained and thoughtfully updated first-floor condo in the heart of Winter Garden. This 2-bedroom, 2-bath residence offers 918 square feet of comfortable living space with tasteful improvements and smart use of space throughout. Step inside to an inviting, open living and dining area featuring wood-look luxury vinyl flooring throughout, recessed lighting and an abundance of natural light. Recently replaced windows are an especially valuable improvement, enhancing the home’s fresh, updated feel while offering an upgrade buyers will appreciate for years to come. The kitchen has been tastefully refreshed with granite countertops, a stylish tile backsplash, breakfast bar and thoughtful cabinetry updates, creating a functional space that opens naturally to the dining and living areas. A standout feature is the custom reconfigured laundry and pantry area, thoughtfully redesigned to make the most of the available space. The stackable washer and dryer provides convenient laundry access while allowing for additional organized pantry and cabinet storage—an incredibly functional upgrade that you won’t find in every unit. Both bedrooms are comfortably sized, and the continuous wood-look flooring creates a clean, cohesive feel throughout the home. Additional improvements include a tankless water heater, updated lighting and numerous thoughtful touches throughout. Enjoy your own large covered and screened front porch, offering additional space to relax and enjoy the Florida weather. Combined with convenient first-floor living and a well-maintained community setting, this home offers an easy, comfortable lifestyle in a desirable Winter Garden location. Bright, clean, thoughtfully updated and truly move-in ready—this is a condo that stands out from the rest.

27 Windtree Lane Unit 102, Winter Garden
$663,065
4 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12331 Silk Mimosa Alley, Winter Garden
$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
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