Winter Garden/Oakland Homes with No Deed Restriction Community Extras

Winter Garden/Oakland Homes with No Deed Restriction Community Extras

Welcome to the charming community of Winter Garden and Oakland, nestled in the heart of Central Florida. This enchanting region is known for its picturesque landscapes, rich history, and vibrant local culture. With its close proximity to Orlando, residents enjoy the perfect blend of small-town charm and urban convenience, making it an ideal place to call home.

Winter Garden boasts a delightful historic downtown area filled with boutique shops, cozy cafes, and a thriving farmer's market that draws visitors from near and far. The scenic West Orange Trail runs through the area, offering miles of paved paths for walking, biking, and enjoying the beautiful Florida weather. Oakland, with its serene lakes and lush greenery, provides a tranquil escape, perfect for nature lovers and outdoor enthusiasts.

One of the standout features of this region is the availability of homes in communities with no deed restrictions. These properties offer the freedom to personalize your living space without the constraints often found in traditional neighborhoods. Whether you're looking to create a beautiful garden, park your RV, or simply enjoy your property without limitations, these homes provide the perfect canvas for your dreams.

The community extras are abundant in Winter Garden and Oakland, with an array of recreational facilities, parks, and family-friendly events that foster a strong sense of community. From local festivals to outdoor concerts, there’s always something happening here.

If you're seeking a place that combines the warmth of community with the freedom of homeownership, Winter Garden and Oakland are waiting to welcome you with open arms. Discover your perfect home in this vibrant and inviting region today!

Newest Winter Garden/Oakland Homes with No Deed Restriction Community Extras

2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code

Experience refined Florida living in this beautifully appointed 2024-built residence, ideally situated within the gated community of Del Webb Oasis. Thoughtfully designed with 2 bedrooms plus a versatile bonus room—perfect as a 3rd bedroom, private home office, den, or sitting room—the home offers a desirable split-bedroom floor plan that provides both privacy and comfort. upgrades are showcased throughout, including luxury vinyl flooring, recessed lighting, and contemporary finishes. At the heart of the home, the stylish kitchen features Tier 3 upgraded finishes complemented by Whirlpool appliances, creating an inviting space that seamlessly blends modern design with everyday functionality. Step outside to the screened-in lanai, an ideal setting for peaceful morning coffee, outdoor dining, or relaxing Florida evenings. The 2-car garage is equally well appointed with sleek epoxy flooring and an EV charger for added convenience. Beyond the home, Del Webb Oasis offers a gated, amenity-rich lifestyle designed for recreation, relaxation, and connection. Association fees include cable and internet, while the community provides an exceptional setting to stay active, socialize, and enjoy the best of Florida living. Adding to its appeal, the property is approximately 20 minutes from the Walt Disney World Resort area, depending on traffic—placing world-class dining, shopping, entertainment, and recreation within easy reach. Built in 2024 and beautifully upgraded throughout, this exceptional residence delivers the perfect combination of modern luxury, low-maintenance living, and resort-style convenience.

13418 Princess Street, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Orchard Pk/Stillwater Xing Ph SubDv. ⋅ 34787 Zip Code

WELCOME TO 3019 CHERRY ORCHARD LANE, A BEAUTIFULLY REMODELED HOME IN THE HEART OF WINTER GARDEN! This stunning residence has just undergone an impressive transformation, offering a fresh, modern, move-in-ready interior that truly stands out in the neighborhood. The home features NEW INTERIOR AND EXTERIOR PAINT (2026), a COMPLETELY RENOVATED KITCHEN, and BEAUTIFULLY UPDATED BATHROOMS, all thoughtfully redesigned with contemporary finishes and attention to detail. Every improvement was carefully selected to create a bright, stylish, and welcoming atmosphere throughout the home. This is a rare opportunity to own a beautifully renovated property offering a level of updates and finishes that is difficult to find in the surrounding area. Ideally located in desirable Winter Garden, with convenient access to shopping, dining, entertainment, parks, major roadways, and everything this highly sought-after area. MOVE-IN READY and beautifully refreshed from the inside out, schedule your private showing and come see what makes this home truly special!

3019 Cherry Orchard Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code

Virtually Staged. **Virtually Staged | Tenant Occupied | Great Investment Opportunity** Beautiful two-story home in the desirable Storey Grove community in Winter Garden, currently rented for the full year—ideal for investors seeking immediate rental income. This home offers 3 bedrooms, 2.5 bathrooms, approximately 1,717 sq. ft. of living space, peaceful pond views, and a detached two-car garage. The open-concept layout features a kitchen with island overlooking the family and dining areas. Upstairs, the primary suite includes an oversized bathroom and walk-in closet. Residents enjoy a clubhouse, fitness center, resort-style pool, hedge maze, and dog park. Conveniently located near SR-429, US-192, and SR-545, just minutes from Walt Disney World, Orange County National Golf Center, shopping, dining, and Walmart. A great opportunity in one of Winter Garden’s most sought-after communities.

11367 Great Rock Street, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 2 SubDv. ⋅ 34787 Zip Code

Location, location, location!! Incredible opportunity to own a popular Whitman II model in the desirable Oakland Trails community with direct walkable access to the West Orange Trail! Imagine walking or biking to dinner in downtown Winter Garden just minutes away! You're also just minutes from the Florida Turnpike and all the new shopping in Clermont, including Costco just down the road. The location of this home is incredible! From the moment you step through the glass-paneled front door, you are greeted by a bright and airy two story foyer featuring warm luxury vinyl flooring and a contemporary staircase accented with sleek, industrial cable railings. The main level effortlessly transitions into a sun-drenched living space, anchored by large sliding glass doors that open up to an outdoor patio and frame views of the surrounding neighborhood. A neutral color palette and recessed lighting throughout enhance the sophisticated, move-in-ready aesthetic of the home. At the heart of the home is a chef-inspired gourmet kitchen designed for effortless entertaining. The massive central island takes center stage, featuring gleaming white quartz countertops, a deep undermount sink, and comfortable breakfast bar seating for four beneath stylish pendant lighting. Striking dark espresso cabinetry provides an abundance of storage space and beautifully contrasts the modern herringbone tile backsplash. Equipped with premium stainless steel appliances—including a built-in wall oven and microwave combo, a cooktop, and a French-door refrigerator—this kitchen is as functional as it is beautiful, complete with a spacious walk-in pantry nearby. Opposite the main living area, a formal dining space is defined by its soaring high-volume ceiling and a dramatic, modern halo chandelier that casts a warm glow over your dinner parties. Upstairs you'll love the oversized loft area that's open to below - perfect for cozier gatherings with the family. The secondary bedrooms are generously sized and each have their own walk in closets. The primary suite features a grand entrance with french doors leading to the large bedroom with two massive walk in closets, a tray ceiling, and more french doors leading to the spa inspired primary bath. The upstairs laundry room is conveniently placed to complete the home. With major shopping, dining, and entertainment options located within 15 minutes of this community, you have no shortage of lifestyle at your fingertips! You can get to Disney parks in about 20-25 minutes! You're also zoned to A rated schools, and have a very popular charter school - Oakland Avenue Charter School just minutes away. Come tour this home today!

2273 Standing Rock Circle, Oakland

3 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 2 SubDv. ⋅ 34787 Zip Code

Beautiful **3-bedroom, 2-bathroom condo at The Grove Resort & Water Park**, offered **fully furnished and turnkey**! Enjoy the perfect combination of comfort, resort-style living, and investment potential in the Orlando area. The unit features a spacious living area, fully equipped kitchen, TVs throughout, in-unit washer and dryer, and a private balcony. The Grove offers outstanding amenities including heated pools, hot tub, Surfari Water Park, lazy river, water slides, splash area, FlowRider, 24-hour fitness center, restaurant, bar & grill, arcade, mini golf, and Lake Austin access. Conveniently located near Disney and Orlando’s world-famous theme parks, with complimentary daily shuttle service to Disney parks. Ideal as a vacation home, second home, or investment property. Rental opportunities may be available through the resort program, subject to applicable rules and requirements. **Fully furnished, fantastic amenities, and an unbeatable Orlando vacation lifestyle!**

14501 Grove Resort Avenue Unit 2608, Winter Garden

6 Beds ⋅ 6 Baths ⋅ Oakland Parka SubDv. ⋅ 34787 Zip Code

Virtually Staged. Welcome to 907 Celadon, overlooking a broad conservation landscape with Lake Apopka views. Main home highlights include a first-floor primary suite, two substantial rooms off the foyer offering flexibility for two private offices, a guest suite or au pair suite, and a nearly 40-foot screened porch with new summer kitchen. A separate 907-square-foot carriage house apartment above the garage offers exceptional flexibility for multigenerational living, extended-stay guests or an in-law suite. Across the rear of the home, the kitchen, dining and living areas unfold as one expansive social space. The chef’s kitchen offers generous workspace for more than one cook, with extensive cabinetry throughout—including an entire wall of cabinetry—plus storage beneath the oversized island and seating for six. A long wall of sliding glass doors opens to the screened porch, extending the living space outdoors. Beyond it, the fully landscaped backyard offers generous green space with room to envision a future pool and pool house. Set apart from the main living spaces, the first-floor primary suite occupies its own wing at the rear of the home. A door from the kitchen closes the wing from the rest of the first floor, while the bedroom opens directly to the screened porch. An expansive dressing room—with extensive built-ins, a center island and chandelier—and a spacious primary bath complete the suite. Upstairs, three bedrooms and an oversized loft give younger family members a level of their own. The loft is currently arranged for movies, Xbox, play and a homework station, while the first floor remains where everyone comes together. Daily routines are easier here. Bright blue built-in lockers off the mudroom keep bags and shoes organized, while the large laundry room includes a dedicated dog wash station. Connected to the main residence by a covered breezeway, the carriage house includes a separate entrance, kitchenette, full bath and closet. Currently used as a private executive office, it offers flexibility for extended family or guests as needs change. Oakland Park’s golf-cart lifestyle is one of its signature advantages, and 907 Celadon has a dedicated golf-cart garage for it. Historic Downtown Winter Garden—Plant Street, the Farmers Market, dining and Crooked Can—is an easy cart ride from home. Direct access to the West Orange Trail offers 22 miles for walking, jogging and biking, plus community pools and green spaces.

907 Celadon Street, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code

If you’ve been searching for a spacious Winter Garden home with a private pool, peaceful conservation views and room for everyone, this former model may be exactly what you’ve been waiting for! With 5 bedrooms, 4 full bathrooms and the potential for a 6th bedroom, this home combines privacy, flexibility and Florida indoor-outdoor living in a way that’s increasingly difficult to find. Situated on a peaceful wooded conservation lot, the home has been thoughtfully updated with a renovated kitchen, LVP flooring throughout the first floor, and new carpet and paint upstairs. Generous living and dining areas provide plenty of room for everyday living and entertaining, while the family room features easy access to the screened pool and deck. The spacious primary suite includes a private sitting area and built-in shelving, creating a comfortable retreat. Upstairs, the oversized bonus room with its own adjoining full bathroom offers exceptional flexibility and could serve as a second primary suite, private guest quarters, media room or game room. Need even more space? The downstairs office could potentially be converted into a 6th bedroom, making this floor plan adaptable to a variety of needs. Step outside to one of the home's most appealing features—the screened-in pool and deck overlooking the wooded conservation area. With no immediate rear neighbor, it's a private setting for morning coffee, afternoons by the pool, entertaining friends or simply relaxing at the end of the day. Located in the beautiful gated Wintermere Pointe community, this home brings together the space, privacy and flexibility along with a private pool and conservation setting that can be difficult to find. Call and schedule your private showing today!

2242 Wintermere Pointe Drive, Winter Garden

6 Beds ⋅ 4 Baths ⋅ Mcallister Landing SubDv. ⋅ 34787 Zip Code

A new dryer was installed in May 2024, and a new washing machine was installed in August 2025 with a two-year warranty. In June 2026, the upstairs A/C indoor unit was replaced. The installation included all labor and materials, as well as product registration for parts warranty. 1523 Juniper Hammock Street welcomes you with a striking two-story façade, graceful architectural lines, and a beautifully composed exterior that creates an impressive sense of arrival. At the rear, the home opens to a lush, peaceful setting dominated by mature trees and natural greenery, offering a refreshing backdrop and a greater sense of privacy. A partial water view from the side adds another layer of beauty without taking away from the secluded, tree-lined atmosphere. Together, the elegant exterior and serene natural surroundings create a home that feels both distinguished and wonderfully connected to the outdoors.

1523 Juniper Hammock Street, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code

Amazing, 4 bedroom, 3.5 bath 3327sqft, WATERFRONT home in highly desirable Waterleigh west of Disney. This luxurious home has a large covered and paved front porch to watch the morning rise and day go by and a large covered back paved patio to enjoy those peaceful, colorful, sunsets over the water with about 50 feet of frontage. The foyer and front formal dining room have elegant arched hallways and coffered ceilings. Walk into the main living area through the main hall or through the Butlers pantry to the Gourmet kitchen. Next to the Butlers pantry is a large walk-in closet pantry for extra storage. The Gourmet kitchen has light, tiered, cabinets with crown molding, all stainless steel appliances, and accented by gorgeous Quartz counters. glass cooktop with separate built in microwave and oven. (French door fridge with bottom freezer will be installed.) The large sink island features the sink and breakfast bar overlooking the family and cafe area with plenty of windows and door for great neutral light and amazing views of the water and large back yard . The home has tall ceilings and tiled with wood plank type tile throughout the first floor except for the first floor Master bedroom. The Master also faces West overlooking the pond for great sunset views. Very large with coffered ceilings and lots of light. The cute double doors lead into the spacious master-bath with large separate vanities, double sinks, separate shower stall, separate toilet room, garden tub, linen closet, and Massive clothes closet. Back in the main great room is a hall filled with more cabinet storage space, leading to the large laundry room, garage, and stairs. The beautiful wood stairs and iron rail leads up to a spacious 20x18 loft/game room. All of the bedrooms have walk-in closets. One has a separate private bath, and the other two split bedrooms share a hall bath split with dual sinks and separate room for baths and toilet for maximum use. The home has modern decor styled raised panel doors throughout and plenty of storage space. This home has Smart technology for easy use and remote functionality. This amazing home is in the highly desirable community “Waterleigh.” Located just off the 429 west of Disney, This community amenities include a huge resort style pool, fitness gym, club house, dog park, huge sports fields, playground, beach volleyball, Tennis, lake view BBQ/picnic area, with sidewalks that wind around the scenic lakes, nature, and community for a relaxing and enjoyable lifestyle with periodic fitness stops if you choose. Fast and easy access anywhere. New Florida Hospital, restaurants and shopping are all close and many more are being built nearby. Great schools; Water Spring Elementary, Water Spring Middle, and Horizon Highschool.

8819 Sonoma Coast Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hawksmoor-Ph 1 SubDv. ⋅ 34787 Zip Code

Welcome home to Hawksmoor, a highly sought-after community in Horizon West and Winter Garden. This home is like new, as it was used primarily as a Vacation home. Just minutes from the theme parks and major highways. This spacious bungalow-style home offers 2,372 sq ft of contemporary design for today's lifestyle. The highlight of the home is the upgraded Gourmet Kitchen, complete with light cabinetry, a beautiful backsplash, etc. Just off the Kitchen is a wonderful space for entertaining friends and family. In addition, you have a private office on the first floor.. Dining room chandelier along with washer & Dryer do not convey Upstairs,you'll find an expansive loft that provides multiple options as a Media Room, playroom, game room, etc. Two additional bedrooms upstairs are a very generous size to be used as bedrooms or guest rooms.. The primary suite features a beautiful tray Ceiling,a luxurious en-suite bathroom, and abundant closet Space. A second-floor laundry is ideal for the entire family. A list of the multilpe amenties offered by this sought after community. Call to view this like new home before it is to late!

16614 Wingspread Loop, Winter Garden

RARE corner 2.5-acre homesite in Winter Garden's sought-after Lake Avalon. No HOA and A-1 zoning that welcomes a custom estate, ADU, extra garage, barn, horses, or RV and boat storage. High and dry with gentle slope, mature trees, and a mix of cleared and wooded ground already prepped for plans and permitting, this 333-by-327-foot parcel offers real, usable space and strong frontage just minutes from Hamlin Town Center, Horizon West amenities, and Disney's back entrance. Enjoy country privacy without giving up convenience or top-rated schools. Utilities and survey are available; bring your own builder or partner with a local custom firm that knows the area. Corner, no-HOA acreage this close to the growth corridor is increasingly scarce - an opportunity to design the property you've been waiting for rather than settle for a typical subdivision lot.

17206 Red Bird Road, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code

Welcome to 15675 Panther Lake Drive, an exceptional lakefront residence within the prestigious Lakeshore Preserve community of Winter Garden, where refined interiors, expansive water views, and effortless Florida living come together in a beautifully curated setting. Offered fully furnished, this sophisticated five-bedroom, five-bathroom residence has been thoughtfully enhanced with custom millwork, elevated finishes, and carefully selected upgrades throughout. The heart of the home is an expansive open-concept living space, seamlessly connecting the family room, dining area, and kitchen while framing beautiful views of the lake. Designed equally for intimate everyday living and sophisticated entertaining, the main level also features a dedicated coffee station, generous pantry and storage spaces, laundry room, and a private primary suite offering the convenience of first-floor living. One of the three garage bays has been thoughtfully transformed into a fully equipped private fitness studio, creating a dedicated wellness space within the residence while offering the flexibility to be converted back to garage use if desired. Upstairs, four additional bedrooms are complemented by a spacious loft and private home office. Expansive windows throughout the upper level capture the lake views and bring an abundance of natural light into the home. Beyond its interiors, the property's waterfront setting creates a sense of openness and tranquility, offering a beautiful lake view and access, summer kitchen, Florida room, heated pool and a spa. It is a true oasis from morning through evening. Ideally positioned in Winter Garden, the residence provides the privacy and distinction of an upscale community while remaining conveniently connected to the area's exceptional dining, shopping, entertainment, and lifestyle destinations. 15675 Panther Lake Drive represents a rare opportunity to acquire a fully furnished*, beautifully appointed lakefront home where comfort, functionality, and the Florida lifestyle exist in perfect balance.

15675 Panther Lake Drive, Winter Garden

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