Winter Garden/Oakland Homes with Street Lights Community Features

Winter Garden/Oakland Homes with Street Lights Community Features

Welcome to Winter Garden and Oakland, Florida—a vibrant tapestry of charm, community, and natural beauty nestled in the heart of Central Florida. Known for its picturesque landscapes and a rich history, this region offers a unique blend of small-town warmth and modern conveniences, making it an ideal place to call home.

Winter Garden is renowned for its historic downtown area, where you can stroll along brick-paved streets lined with boutique shops, cozy cafes, and delightful eateries. The community is alive with events throughout the year, from farmers' markets to seasonal festivals, fostering a strong sense of camaraderie among residents. Just a stone's throw away, the tranquil town of Oakland complements Winter Garden with its lush parks and scenic trails, perfect for outdoor enthusiasts and families alike.

One of the standout features of homes in this region is their commitment to community living, exemplified by the Homes with Street Lights community. This thoughtfully designed neighborhood not only enhances safety and accessibility but also promotes a welcoming atmosphere for evening strolls and neighborhood gatherings. Picture yourself walking along tree-lined streets illuminated by charming street lights, where neighbors become friends and children play freely.

With a variety of housing options ranging from cozy single-family homes to spacious estates, Winter Garden and Oakland cater to diverse lifestyles and budgets. Whether you're seeking a peaceful retreat or a family-friendly environment, this area offers the perfect backdrop for creating lasting memories. Come discover the magic of Winter Garden and Oakland—where community spirit shines as brightly as the Florida sun!

Newest Winter Garden/Oakland Homes with Street Lights Community Features

no property photo
$1,300,000
3 Beds ⋅ 2 Baths ⋅ S5160667 MLS
LOCATION, ACREAGE, AND ENDLESS POSSIBILITIES! Discover an exceptional opportunity to own 4.98 acres (approximately 216,929 square feet) of prime real estate in the highly desirable and growing Winter Garden area! Whether you are looking for a private residential estate, an agricultural property, an equestrian retreat, or land with future development potential, this unique property offers tremendous possibilities for homeowners, investors, builders, and developers. EXCELLENT POTENTIAL FOR FUTURE DEVELOPMENT! Currently zoned A-1 Agricultural, this expansive parcel offers the opportunity to explore subdivision into up to three individual parcels, subject to Orange County review and approval. Buyers may also investigate the possibility of rezoning for commercial, residential, or other permitted uses through the appropriate application and approval process with Orange County. This flexibility makes the property especially attractive to investors and developers seeking land for future projects in Central Florida. AN ADDED BONUS – AN EXISTING HOME ON THE PROPERTY! The property features a charming single-story residence offering 3 bedrooms, 2 bathrooms, and approximately 1,440 square feet of living space. The home includes tile flooring throughout, granite kitchen countertops, a tile roof, and comfortable living areas. The property also features a pole barn, additional outbuildings, storage sheds, fenced pasture areas, and beautiful mature trees, creating an inviting country atmosphere with plenty of room to enjoy. Retreat to the inviting primary bedroom, featuring elegant marble-look tile flooring, abundant natural light, recessed lighting, and a contemporary ceiling fan. The spacious layout offers room for a desk or sitting area, while generous closet space provides convenient storage. The adjoining bathroom showcases striking marble-look wall and floor tile, a double-sink vanity with cabinetry, gold-tone faucets, and an illuminated mirror. A soaking tub and separate glass-enclosed shower with a rainfall showerhead create a relaxing retreat, complemented by dramatic dark tile accents. THE BEST OF BOTH WORLDS – COUNTRY LIVING WITH CITY CONVENIENCE! Enjoy the privacy, space, and freedom of acreage living while remaining conveniently located near Winter Garden's expanding residential communities, shopping, dining, major roadways, and Central Florida attractions, including Walt Disney World. LIVE, INVEST, OR EXPLORE FUTURE DEVELOPMENT! The existing residence provides immediate residential utility while the surrounding acreage offers opportunities for agricultural activities, equestrian use, a private estate, or potential future development. DON'T MISS THIS OPPORTUNITY TO OWN NEARLY FIVE ACRES IN WINTER GARDEN! Large parcels with an existing home and multiple potential uses are worth exploring. Bring your vision and discover what this exceptional property could become!

17706 Marsh Road, Winter Garden
15530 Sunquat Dr, Winter Garden
$599,999
4 Beds ⋅ 4 Baths ⋅ O6455496 MLS
Virtually Staged. Welcome to this stunning 4-bedroom, 3.5-bath home located in the highly desirable Hamlin Reserve community in Horizon West, Winter Garden! Thoughtfully designed with spacious living areas, modern finishes, and a versatile floor plan, this home offers the perfect setting for comfortable everyday living and effortless entertaining. Upon entering, you are greeted by an inviting foyer featuring soaring volume ceilings and stylish vinyl flooring throughout the entire first floor. A versatile flex room just off the entry provides endless possibilities and can be customized to suit your needs as a home office, den, formal living room, or additional dining space. The open-concept layout seamlessly connects the spacious family room, kitchen, and dining area, creating a warm and welcoming atmosphere. The well-appointed kitchen is sure to impress with its oversized island with seating, granite countertops, solid wood cabinetry, gas range, stainless steel appliances, and beautiful decorative backsplash. Conveniently located nearby are a half bath, a dedicated mudroom area with access to the garage, and sliding glass doors that open to the covered rear patio, offering the perfect spot to unwind or enjoy outdoor gatherings. Upstairs, you'll discover a spacious loft that provides additional flexible living space, ideal for a media room, playroom, or secondary family gathering area. The thoughtfully designed split-bedroom floor plan offers added privacy and functionality. The generously sized primary suite serves as a peaceful retreat, featuring a private en-suite bathroom with dual sinks, a standalone shower, and a walk-in closet. The second floor is completed by a conveniently located laundry room just off the loft, a private en-suite bedroom with its own standalone shower, two additional spacious bedrooms, and a full bathroom. For added convenience and modern appeal, all four bathrooms feature smart toilets. Residents of Hamlin Reserve enjoy wonderful community amenities, including a community pool, playground, and clubhouse. Ideally situated in the heart of Horizon West, this home is within walking distance of local dining and everyday conveniences, with Cinepolis, PopStroke, an exciting variety of restaurants, breweries, shopping, and entertainment just minutes away. Experience the best of the Horizon West lifestyle with this beautiful home offering space, comfort, community amenities, and an unbeatable location. Schedule your private showing today!

15530 Sunquat Dr, Winter Garden
925 Butter Oaks Court, Winter Garden
$619,000
3 Beds ⋅ 3 Baths ⋅ O6455077 MLS
Timeless Craftsman Charm Meets the Best of Winter Garden Living! Welcome to this inviting Craftsman-style home in the highly desirable Winter Oaks community, where small-town charm meets the convenience of modern Florida living. Located in a golf-cart-friendly neighborhood and within minutes of Historic Downtown Winter Garden, this home provides an opportunity to enjoy everything this sought-after area has to offer and more! From the welcoming double front porches to the spacious, thoughtfully designed interior, this home combines character, comfort, and functionality. The kitchen features beautiful quartz countertops, wood cabinetry, stainless steel appliances, a gas range, and a versatile island with additional storage and seating. Absolutely perfect for everyday living and entertaining! The first-floor's open concept, high ceilings and abundant natural light is an ideal way to be welcomed inside. The primary suite, also located on the first floor, is a private retreat, complete with a walk-in closet and an en-suite bathroom featuring dual vanities, a jetted soaking tub, and a separate shower. The second story, also full of character and charm, is an amazing space for loved ones and/or valued guest. Step outside to enjoy the screened lanai, fenced backyard, and separate patio ideal for friends and family gatherings, weekend barbecues or simply relaxing in the Florida sun. Residents of Winter Oaks enjoy community activities & amenities including a swimming pool, cabana, and playground. The location is equally impressive, offering convenient access to the West Orange Trail, shopping, dining, and the unique shops, restaurants, and year-round activities of Historic Downtown Winter Garden. Hurry, as this opportunity has too many amenities to list! Call today before it's gone tomorrow!

925 Butter Oaks Court, Winter Garden
14253 Country Estate Drive, Winter Garden
$1,675,000
5 Beds ⋅ 5 Baths ⋅ O6453112 MLS
Lakefront living with room to spread out. Welcome to 14253 Country Estate Drive. Set on nearly three acres along Black Lake, this two-story brick pool home pairs timeless character with expansive water views in an established community of custom homes. Mature oaks frame the circular driveway, creating a welcoming arrival to a residence offering approximately 5,504 square feet, five bedrooms, four full baths, and one half bath. Lake views greet you from the foyer and draw you into the soaring great room, where a wood-burning stone fireplace, tall windows, and French doors create an inviting setting for everyday living and entertaining. The spacious kitchen features a generous center island, extensive cabinetry, and adjoining casual dining, while a separate formal dining room provides space for larger gatherings. The main-floor primary suite offers its own screened lanai, a quiet place to start the day overlooking the grounds. An office with a closet provides flexibility for a potential fifth bedroom, and two upstairs bonus rooms offer additional space for recreation, hobbies, or working from home. Outside, the pool, lanai, and expansive backyard make the waterfront setting the centerpiece of the home. Enjoy afternoons by the water, outdoor dining, or time on Black Lake boating, fishing, paddleboarding, and jet skiing. A side-entry three-car garage completes the property. Conveniently located near the shopping and dining at Winter Garden Village at Fowler Groves, with access to SR 429, SR 408, and Florida’s Turnpike, this home brings together spacious interiors, generous grounds, and the Florida lakefront lifestyle.

14253 Country Estate Drive, Winter Garden
17316 Melogold Way, Winter Garden
$530,047
3 Beds ⋅ 3 Baths ⋅ TB8565503 MLS ⋅ 19 BLDG.
Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a two-car garage, perfectly located in the heart of Winter Garden. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. This popular Walden plans features finishes from the AW Collection Milan with clean, modern touches. The kitchen boards 42" cabinets, quartz countertops and tiled backsplash. Additional highlights include a detached two-car garage with private fenced courtyard space and upgraded 8' doors. Ideally situated, you’re just 37 minutes from Orlando International Airport, 20 minutes from world-famous Disney theme parks, and 30 minutes from Celebration. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

17316 Melogold Way, Winter Garden
12818 Sunset Walk, Winter Garden
$659,008
4 Beds ⋅ 3 Baths ⋅ O6455470 MLS ⋅ Toll Brothers BLDG.
Under Construction. New Construction by Toll Brothers in Winter Garden’s Horizon West! Estimated completion in early 2027. Don't miss the opportunity to show your clients this beautiful corner-unit townhome! A welcoming covered entry leads into a thoughtfully designed, spacious living area featuring a dedicated dining space, gourmet kitchen with breakfast bar, and inviting great room with access to a private courtyard, perfect for relaxing or entertaining. The spacious primary suite offers a generous walk-in closet and a private ensuite bathroom featuring dual vanities, a separate shower, and a private water closet. Experience the quality, style, and thoughtful design of Toll Brothers in one of Winter Garden's desirable locations!

12818 Sunset Walk, Winter Garden
557 Lake Cove Pointe Circle, Winter Garden
$2,249,999
5 Beds ⋅ 5 Baths ⋅ O6447759 MLS
Virtually Staged. Some homes are updated. Other are completely reimagined. Welcome to an extraordinary lakefront retreat in the highly sought-after golf cart district of historic Downtown Winter Garden where an extensive, designer-led transformation has brought fresh style, thoughtful functionality and an entirely new feel to this exceptional property. Offering 5 bedrooms, 4.5 bathrooms, a dedicated office, and a theater/loft area, this home delivers the space and flexibility to fit the way you live. The interior has been gutted and beautifully redesigned with light, bright airy living spaces and curated finishes that make an impression from the moment you walk through the door. The stunning kitchen is a true centerpiece: open, inviting and designed to bring everyone together, whether it's a relaxed weeknight dinner or a house full of guests. Beautifully renovated bathrooms carry the designer aesthetic throughout, creating a cohesive balance of comfort and sophistication. Every gathering space feels connected, yet the layout still provides plenty of places to find a little privacy. Two primary suites give this floor plan rare versatility for multigenerational living, visiting family or simply having room to spread out. The first-floor primary suite offers privacy and convenience, while the upstairs primary retreat features its own balcony overlooking the lake. Imagine starting the day with coffee and a waterfront views or watching the sunset from your private escape. the upstairs suite also has its own laundry and a separate custom laundry room with double washers and dryers keeps busy households running smoothly. Outside is where this home truly becomes a lifestyle. Your private waterfront setting features a swimming pool, poolside cabana, boathouse, dock and direct access to the lake. Spend your afternoons boating or fishing, host unforgettable gatherings by the pool and end the day relaxing by the water. Newly added electric service at the dock adds convenience for evenings spent enjoying the lakefront atmosphere. Whether you love being on the water or simply love looking out over it, the outdoor spaces invite you to slow down and enjoy where you live. There's room here for quiet mornings, lively weekends, and all the moments in between. The improvements extend well beyond the finishes. An upgraded 400-amp electrical service supports modern living, while the whole-home generator and solar panels offer added practicality and peace of mind. This thoughtful combination of beauty and meaningful infrastructure upgrades makes the renovation as functional as it is striking. And the location? It's one of Winter Garden's most loved. Hop in the golf cart and head downtown, then come home to your own peaceful lakefront haven. Few settings offer this kind of everyday convenience while still feeling like a private getaway. Extensively transformed, exceptionally located and ready for its next chapter, this is a rare chance to have the designer finished home you've been dreaming of without giving up the waterfront lifestyle that makes Winter Garden so special. From mornings on the balcony to evenings on the dock, every day here offers another reason to stay a little longer.

557 Lake Cove Pointe Circle, Winter Garden
17906 Hither Hills Circle, Winter Garden
$560,000
4 Beds ⋅ 4 Baths ⋅ O6454564 MLS
3.99 ASSUMABLE MORTGAGE OPPORTUNITY! Built in 2022, this four-bedroom home in Lake Apopka Sound offers single-story living, a three-car garage, and an open layout perfect for entertaining. The spacious kitchen features an oversized island, granite countertops, stainless steel appliances, and ample storage overlooking the inviting great room. A split-bedroom design provides privacy, while the primary suite includes dual vanities, a soaking tub, separate shower, and walk-in closet. Enjoy nearby outdoor adventures at the West Orange Trail and Oakland Nature Preserve, plus dining, boutiques, Plant Street Market, and the Saturday farmers market in historic Downtown Winter Garden. Shopping at Winter Garden Village and access to Florida’s Turnpike, SR 429, and Highway 50 add everyday convenience. Schedule your private showing today! Mortgage assumption subject to lender approval, buyer qualification, and applicable loan terms.

17906 Hither Hills Circle, Winter Garden
17778 Sedona Street, Winter Garden
$814,139
3 Beds ⋅ 4 Baths ⋅ O6455189 MLS
Under Construction. What's Special: Deep Backyard | 1st Floor Primary Bedroom | Loft | Dedicated Study. New Construction – April Completion! Welcome to the Genoa at 17778 Sedona Street in Esplanade at McKinnon Groves! This thoughtfully designed two-story home offers a spacious and inviting layout with a stunning great room that flows seamlessly into the dining area, gourmet kitchen, and expansive lanai, perfect for everyday living and entertaining. The first floor features a private primary suite with large walk-in closet and well-appointed bath, a secondary bedroom suite, half bathroom, and a study, while upstairs includes a versatile loft, flex room, additional bedroom, and full bathroom. Additional Highlights Include: 10' ceilings at first floor, whole house 8' interior doors, door at primary closet to laundry room, outdoor kitchen rough-in, and whole house blinds. Photos are for representative purposes only. MLS#O6455189 Esplanade at McKinnon Groves offers resort-style living in a gated Winter Garden community surrounded by natural beauty. Planned amenities include a fitness center, movement studio, resort pool and spa, Bahama Bar, pickleball, tennis, and bocce courts. Residents will also enjoy yoga lawns, a Bark Park, rose garden, scenic trails, concierge services, and year-round events. Zoned for Lake County schools, it blends everyday convenience with an active lifestyle.

17778 Sedona Street, Winter Garden
6266 Sunny Time Avenue, Winter Garden
$429,890
3 Beds ⋅ 3 Baths ⋅ O6454896 MLS ⋅ 21 BLDG.
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! Introducing the Dahlia interior unit townhome, a new construction home that seamlessly combines luxury and convenience. This modern townhome features 3 bedrooms, 2 full bathrooms, a powder room, and a 2-car rear-facing garage. The first floor is designed with entertaining in mind, offering an open-concept kitchen, café, and gathering room that flow together effortlessly. The chef-inspired kitchen is a highlight, featuring a large center island, a spacious storage pantry, Elkins White cabinetry, a decorative tile backsplash, quartz countertops, and stainless-steel appliances, including a refrigerator and vented microwave. The first-floor powder room adds an extra layer of convenience for guests. The entire first floor, including the kitchen, café, and gathering room is finished with elegant tile flooring. At the end of the day, retreat to your private oasis on the second floor. The Owner’s Suite offers a spacious walk-in closet and a luxurious en suite bathroom with a double-sink, quartz-topped vanity and a glass-enclosed shower. Two additional bedrooms, a secondary bathroom, and a linen closet for added storage are located on the opposite side of the floor, ensuring privacy and plenty of space. Soft, stain-resistant Shaw brand carpet adds comfort to the stairs and bedrooms, creating a cozy atmosphere throughout. For added convenience from day one, this home comes complete with 2" faux wood blinds, as well as a brand new Whirlpool washer and dryer! With thoughtful design, high-end finishes, and a focus on everyday convenience, the Dahlia townhome is a perfect blend of style and practicality, offering a truly elevated living experience.

6266 Sunny Time Avenue, Winter Garden
6367 Argent Wood Drive, Winter Garden
$433,490
3 Beds ⋅ 3 Baths ⋅ O6454893 MLS ⋅ 19 BLDG.
Discover Silverleaf Oaks in Winter Garden! This new home community will feature a collection of single-family and townhomes in desirable Horizon West. Located in the heart of Orlando’s attractions, residents will enjoy an array of amenities, including a resort-style pool, cabana, and playground – without a CDD. Plus, minutes to shopping, dining, and entertaining! The new construction Foxtail interior unit townhome features 3 bedrooms, 2 full bathrooms, a powder room, an open concept kitchen, café and gathering room, a private courtyard, and a 2-car rear-facing garage. The first floor is ideal for entertaining, featuring a spacious gathering room, café and kitchen, with a large center island, storage pantry, white cabinetry, a decorative tile backsplash, quartz countertops, and Whirlpool stainless-steel kitchen appliances- including a refrigerator. A powder room and laundry on the first floor add to the thoughtful convenience. Enjoy entertaining loved ones from your private, fenced rear courtyard. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and en suite bathroom with a double sink quartz-topped vanity, private water closet, and a walk-in shower. Two additional bedrooms, the secondary bathroom and extra storage offered by a linen closet are on the opposite side of the second floor, offering privacy and space for everyone. Professionally curated design finishes for this popular Foxtail townhome include wood-look luxury vinyl plank flooring throughout the first floor living areas, tile flooring in the laundry room and bathroom, and soft, stain-resistant, Shaw brand carpet in the bedrooms and second floor living areas, and so much more. This new construction townhome perfectly blends luxury, convenience, and modern design, making it the ideal place to live and unwind. Schedule your tour today!

6367 Argent Wood Drive, Winter Garden
13900 Lanyard Way, Winter Garden
$769,650
5 Beds ⋅ 5 Baths ⋅ O6454639 MLS
Short Sale. Welcome to this spacious 5-bedroom, 5-bathroom home in the desirable Encore at Ovation community in Winter Garden! Featuring a rare dual primary suite layout, this home offers an open-concept design with an upgraded kitchen showcasing a natural gas stove, oversized island, farmhouse sink, and stainless-steel appliances. The kitchen flows seamlessly into the dining and family rooms, perfect for entertaining. The first floor includes a primary suite, private den/office, and additional full bathroom. Upstairs, enjoy a versatile loft, convenient laundry room, and luxurious second primary suite overlooking the conservation area, complete with dual sinks, soaking tub, separate shower, and oversized walk-in closet. Relax on the covered back porch overlooking a private backyard with no rear neighbors. Additional features include fiber-optic internet, surround sound speakers and prewiring for security cameras. All this plus the added benefit of solar panels to help with those electricity bills. Residents enjoy resort-style amenities including a pool, fitness center, playground, dog park, and yard maintenance. Conveniently located minutes from Walt Disney World and Flamingo Crossings, offering shopping, dining, and entertainment. A rare find combining space, privacy, and an unbeatable location!

13900 Lanyard Way, Winter Garden
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