Winter Garden/Oakland Homes with Street Lights Community Features

Winter Garden/Oakland Homes with Street Lights Community Features

Welcome to the enchanting neighborhoods of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant region is renowned for its rich history, picturesque landscapes, and a warm sense of community that welcomes residents and visitors alike. With its charming downtown area, lined with boutique shops and delightful eateries, Winter Garden offers a perfect blend of small-town charm and modern convenience.

One of the standout features of this area is the stunning array of homes that grace its tree-lined streets, particularly those in the Homes with Street Lights community. Imagine evening strolls under the soft glow of street lamps, where neighbors greet each other with friendly waves, and children ride their bikes with carefree laughter. This community fosters an inviting atmosphere, making it an ideal place for families, retirees, and everyone in between.

Residents of Winter Garden and Oakland enjoy easy access to beautiful parks, scenic trails, and the sparkling waters of Lake Apopka. The area is also conveniently located near major highways, providing seamless connectivity to Orlando's world-famous attractions, shopping, and dining options.

Whether you’re seeking a cozy bungalow or a spacious family home, the real estate options here cater to diverse preferences and lifestyles. Living in Winter Garden and Oakland means embracing a lifestyle filled with outdoor adventures, community events, and a strong sense of belonging. Come discover the magic of this remarkable region, where every day feels like a celebration of life!

Newest Winter Garden/Oakland Homes with Street Lights Community Features

$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
$699,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1a SubDv. ⋅ 34787 Zip Code
Experience refined Florida living in this impeccably maintained single-story 4BD/3BA residence set on an oversized corner lot in the prestigious Waterleigh community. Thoughtfully designed interiors blend elegance with comfort, highlighted by rich finishes, abundant natural light, and a seamless open layout. The gourmet kitchen showcases espresso cabinetry, granite surfaces, a striking center island, modern lighting, stylish backsplash, and a spacious pantry — all appliances included. The primary suite offers a serene retreat with luxury vinyl plank flooring, tray ceiling, quartz dual vanities, a soaking tub, glass-enclosed shower, and an expansive walk-in closet. Step outside to a private oasis featuring a covered screened lanai, brick patio, and a fully fenced yard ideal for quiet relaxation or elevated entertaining. Additional enhancements include a Ring security system, upgraded blinds, garage storage systems, and specialty garage flooring. Just a short stroll from a resident-exclusive clubhouse with a zero-entry pool, fishing pier, lake views, and sand volleyball. Waterleigh’s resort-style amenities elevate daily living with three pools, two fitness centers, tennis and basketball courts, mini golf, splash pad, dog parks, and scenic trails. HOA includes lawn care, irrigation, and tree maintenance. Located near top-rated schools, a nearby fire station, golf, and evening Disney fireworks views, this smoke-free, pet-free home delivers luxury, convenience, and lifestyle in one of Winter Garden’s most coveted communities.

8711 Eden Cove Drive, Winter Garden
$450,000
3 Beds ⋅ 3 Baths ⋅ Winding Bay Preserve SubDv. ⋅ 34787 Zip Code
Move-in ready 3-bedroom, 2.5-bath townhome in Winding Bay Preserve, built in 2020 with 1,868 heated square feet across two stories. Carpet and ceramic tile flooring throughout, and the washer, dryer, range, microwave and refrigerator all convey. A rear-facing two-car garage with alley access adds everyday convenience. Community amenities include a pool, playground, park and dog park. Located in Horizon West, minutes from Winter Garden shopping and dining, with quick access to SR-429, Avalon Road and the Central Florida attractions corridor. A rare find in one of Horizon West’s most convenient locations.

11102 Hanlon Terrace Alley, Winter Garden
$959,990
5 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12534 Gold Honeysuckle Street, Winter Garden
$909,990
5 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12529 Gold Honeysuckle Street, Winter Garden
$839,990
4 Beds ⋅ 3 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12523 Gold Honeysuckle Street, Winter Garden
$560,000
4 Beds ⋅ 3 Baths ⋅ John Lake Pointe SubDv. ⋅ 34787 Zip Code
Motivated seller! Located in the community of Johns Lake Pointe, this beautifully designed 4-bedroom, 2.5-bath home offers a desirable split floor plan and a spacious 2-car garage. A welcoming front porch sets the tone for this inviting residence. The living room overlooks the private fenced backyard, creating the perfect setting for relaxing or entertaining. The kitchen features chestnut cabinetry, stainless steel appliances, a center island with a sit-in bar, and a separate dining area ideal for gatherings. The primary suite includes a well-appointed primary bathroom with dual sinks, a garden tub, and a walk-in shower. The back porch is protected by a screen. With a recent price improvement, this home presents outstanding value, flexibility, and the opportunity to personalize to your taste. Ideally located less than 20 minutes from Disney, Johns Lake Pointe is a beautifully maintained community offering resort-style amenities, including a clubhouse with a pool and kitchen, fitness center, yoga room, tennis courts, and playground. Enjoy an exceptional lifestyle in a prime location, priced to allow the next owner to create a private oasis. Don’t miss the opportunity to make this remarkable house your home!

745 Marsh Reed Drive W, Winter Garden
$455,000
3 Beds ⋅ 3 Baths ⋅ Osprey Ranch Ph 1 SubDv. ⋅ 34787 Zip Code
Discover an inviting 3-bedroom, 2.5-bath home in Winter Garden, offering a comfortable layout designed for both everyday living and entertaining. The main living areas create an open and welcoming environment, with natural light enhancing the sense of space and connecting the living, dining, and kitchen areas. Upstairs, the bedrooms are thoughtfully separated from the main gathering spaces, providing added privacy and a comfortable retreat at the end of the day. The primary suite offers its own private bath, while the additional bedrooms provide flexibility for family, guests, a home office, or whatever best fits your lifestyle. Beyond the home itself, the location puts you close to everything that makes the Winter Garden area so desirable. Enjoy convenient access to shopping, restaurants, schools, recreation, and major roadways, making it easy to explore Horizon West, greater Orlando, and the many attractions Central Florida has to offer. Whether you're searching for your next home or an investment opportunity in a growing area, this property delivers a combination of location, functionality, and Florida living that is hard to overlook. Schedule your private showing and come see the possibilities for yourself.

15038 Windflower Alley, Winter Garden
$689,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West D SubDv. ⋅ 34787 Zip Code
Welcome to Stoneybrook West—a one-of-a-kind community in Winter Garden! This premier neighborhood offers 24-hour guarded entry, a massive town center, and resort-style amenities including an Olympic-sized pool with a splash zone, state-of-the-art fitness center, playground, tennis, basketball, and pickleball courts. Enjoy lakeside living with a fishing/viewing pier and private boat ramp, plus a full calendar of community events. Best of all, your HOA fees cover both internet and cable! Set on a tranquil pond with no rear neighbors, this home boasts irresistible curb appeal from the moment you arrive. Inside, the thoughtfully designed floor plan balances elegance and ease. The front of the home features formal living and dining areas—perfect for hosting—while the rear opens to a bright, open-concept kitchen and family room ideal for everyday living. The kitchen is a chef's delight with ample counter space, a walk-in pantry, stainless steel appliances, stylish tile backsplash, and a breakfast bar. Step through the sliding doors to a screened patio and fully fenced backyard—a private oasis for pets, play, or peaceful pond gazing. Need space for guests or extended family? A main-floor bedroom with a full bath offers flexibility and privacy. Upstairs, a generous loft awaits—use it as a media room, playroom, or second living area. Both the loft and the primary suite open to a screened balcony with serene views. The primary retreat itself is a showstopper, featuring a garden tub, separate walk-in shower, dual vanities with a makeup station, and an enormous walk-in closet. Convenience continues with an upstairs laundry room equipped with cabinets and a utility sink. Fresh new flooring has been installed throughout the entire upper level, and the home has been treated to a brand-new coat of paint, giving it a clean, modern feel throughout. Recent upgrades also include a new roof (2023), new water heater (2023), and AC (2019). You'll also appreciate surround sound pre-wiring in the family room and loft, ceiling fans throughout, and abundant storage. Located just steps from the resident gate, Balforn Tower Way places you minutes from the community town center, golf clubhouse, top-rated schools, dining, shopping, medical facilities, and entertainment. This is more than a home—it's a lifestyle.

2549 Balforn Tower Way, Winter Garden
$663,065
4 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12331 Silk Mimosa Alley, Winter Garden
$635,000
4 Beds ⋅ 3 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully renovated golf-front home in the gated community of Stoneybrook West. Offering over 2,800 square feet of living space, this home combines a spacious and flexible floor plan with a fantastic setting overlooking the 6th hole and no rear neighbors. Recent improvements include a newer roof and A/C, fresh exterior paint, renovated kitchen, bathrooms, and flooring. The main level offers multiple living and dining spaces, while the kitchen features stone countertops, stainless steel appliances and abundant cabinetry. Upstairs, the spacious primary suite includes a tray ceiling, walk-in closet and private bath with dual vanities and a beautifully remodeled walk-in shower. The oversized loft provides plenty of flexibility for a second living area, media room, playroom or home office. Step outside to a large backyard with expansive golf course views and plenty of room to enjoy the outdoor living. Stoneybrook West offers an impressive collection of amenities, including a community pool, golf, clubhouse, tennis and basketball courts, playgrounds and walking paths. Ideally located near Winter Garden Village, historic Downtown Winter Garden, shopping, dining and major roadways, this home offers a great combination of space, improvements, amenities and community.

15081 Masthead Landing Circle, Winter Garden
$464,990
3 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Under Construction. Waterleigh presents the Sandhill. This spacious townhome features 3 bedrooms and 2.5 baths. As you enter the foyer you are welcomed with powder room, spacious kitchen with bar seating, dining area and a living room overlooking a covered patio. This popular townhome features a single car garage at the rear of the home. This community has upgraded stainless steel appliances and quartz countertops making cooking and cleaning a breeze. As we head upstairs, you are greeted with a loft area. Bedroom one is located just off the loft space and includes a spacious walk-in closet as well as ensuite bathroom with double vanity. The second floor is complete with two guest bedrooms, an additional bathroom, along with laundry room. Like all homes in Waterleigh, the Sandhill includes a Smart home technology package which allows you to control your home with your smart device while near or away. Your new townhome will always have fantastic curb appeal while allowing you time to do the activities your family enjoys most. *Photos are of similar model but not that of exact house. Pictures, photographs, colors, features, and sizes are for illustration purposes only and will vary from the homes as built. Home and community information including pricing, included features, terms, availability and amenities are subject to change and prior sale at any time without notice or obligation. Please note that no representations or warranties are made regarding school districts or school assignments; you should conduct your own investigation regarding current and future schools and school boundaries.*

16534 Barbours Creek Way, Winter Garden
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