Winter Garden/Oakland Homes with Buyer Approval Required Community Features

Winter Garden/Oakland Homes with Buyer Approval Required Community Features

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area is renowned for its picturesque landscapes, charming downtown, and a strong sense of community that beckons families, retirees, and young professionals alike. With its rich history and a commitment to preserving its natural beauty, Winter Garden is a delightful blend of old-world charm and modern conveniences.

As you explore this beautiful locale, you'll discover a plethora of outdoor activities, from the scenic West Orange Trail, perfect for walking, biking, and jogging, to the serene lakes that offer fishing and boating opportunities. The historic downtown area boasts a variety of boutique shops, delightful eateries, and a thriving farmer's market that draws locals and visitors every Saturday. The community's warm spirit is palpable, making it a place where neighbors become friends.

For those considering making Winter Garden or Oakland their home, the community features homes with buyer approval required, ensuring that residents are part of a thoughtfully curated neighborhood. This feature fosters a sense of belonging and enhances the overall quality of life, as it attracts like-minded individuals who value community engagement and collaboration.

With its excellent schools, abundant recreational options, and a strong focus on sustainability, Winter Garden and Oakland offer an idyllic setting for anyone looking to plant roots in Central Florida. Embrace the charm of this vibrant area and discover your dream home in this welcoming community!

Newest Winter Garden/Oakland Homes with Buyer Approval Required Community Features

3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

ONE-YEAR HOME WARRANTY AVAILABLE WITH A FULL-PRICE OFFER! Welcome to this beautifully maintained 3-bedroom, 2-bathroom FIRST-FLOOR condo in the gated Southern Pines community of Winter Garden. Featuring a FRESH INTERIOR REPAINT (2026), UPDATED FIXTURES, a bright, open-concept layout, and NO CARPET THROUGHOUT FOR EASY MAINTENANCE, this home is truly move-in ready. Step inside to a spacious open living area offering a dedicated dining room and breakfast nook just off the kitchen. The kitchen features STAINLESS STEEL APPLIANCES, GRANITE COUNTERTOPS, NEUTRAL CABINETRY, and a pantry offering additional storage. The desirable split-bedroom floor plan provides added privacy, with the primary suite positioned on one side of the home and two additional bedrooms with a guest bathroom on the opposite side. All three generously sized bedrooms feature walk-in closets, providing plenty of storage throughout the home. Ideal as a primary residence or investment property, this low-maintenance condo offers excellent rental potential in a desirable Winter Garden location. HOA dues include internet and basic cable, adding further value and convenience. Southern Pines offers an impressive collection of resort-style amenities, including a pool and spa, fitness center, tennis courts, indoor basketball and volleyball courts, playground, dog park, clubhouse, theater room, billiards room, BBQ area, resident car wash station, and on-site management. Conveniently located near highly regarded public schools, Publix, Winter Garden Village, the West Orange Trail, and vibrant Downtown Winter Garden, with easy access to SR-429, Florida’s Turnpike, and major Orlando attractions. Whether you're searching for a comfortable primary residence or a great investment opportunity, this well-located Winter Garden condo delivers space, convenience, amenities, and value.

431 Southern Pecan Circle Unit 101, Winter Garden

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

Virtually Staged. Virtually Staged. Best value on Wel Webb Oasis . Experience the renowned 55+ lifestyle at Del Webb Oasis, a world-class, resort-style boutique community offering exclusive amenities, a prime Horizon West location, and natural gas single-family homes nestled in wooded conservation. Residents enjoy a full calendar of social events led by a full-time Lifestyle Director, all centered around a stunning clubhouse. Amenities include a resort-style zero-entry pool with lap lanes and sun shelf, private poolside cabanas, spa, outdoor fire pits with fireworks views, fitness center, tennis and pickleball courts, and a walking trail with exercise stations. Just minutes from Flamingo Crossings, Disney, and major new-construction neighborhoods, Del Webb Oasis is ideally located within one of Central Florida’s fastest-growing master-planned communities, with rising home values throughout the area. Every inch of this thoughtfully designed single-story Palmary floorplan is crafted to make life better, happier, and easier. The home features 3 bedrooms, 2 bathrooms, an open-concept kitchen, café, and gathering room, a covered lanai, and a 2-car garage, offering both comfort and functionality for effortless living and entertaining. Step through the impressive foyer into the heart of the home, where the kitchen, café, and gathering room flow seamlessly to the covered lanai for ideal indoor/outdoor living. The kitchen is appointed with 42” soft-close cabinets, granite countertops, a white center island, built-in stainless-steel appliances, sink and faucet, pendant lighting, and a corner walk-in pantry—perfect for making meals and memories. The private Owner’s Suite features a spacious walk-in closet and a luxurious en suite bathroom with dual-sink granite-topped vanity, private water closet, linen closet, and a luxe super shower. Toward the front of the home, the secondary bedrooms, a full bathroom with shower, and laundry room provide privacy and space for everyone. This home is loaded with functional luxury, including a patio extension, kitchen and owner’s bath, laundry room enhancements, interior doors, electrical upgrades, tile flooring throughout, and professionally designed selections throughout. Located on Sunny Retreat Lane. Get spoiled at Del Webb Oasis—after all, this is your time. Your dream home awaits—schedule your visit today!

13360 Sunny Retreat Lane, Winter Garden

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

Welcome to this beautifully maintained 4 bedroom, 3 bathroom corner lot home in the desirable Storey Grove community of Winter Garden. Built in 2021 and thoughtfully finished with elegant taste throughout, this residence offers a bright, open-concept layout designed for both everyday comfort and effortless entertaining. The spacious kitchen anchors the main living area with stylish cabinetry, a large center island with seating, beautiful backsplash, and generous counter space. Situated on an oversized corner lot, the property offers additional outdoor space and an impressive fully fenced backyard. Enjoy Florida living from the covered patio, expansive paver area, and custom pergola, creating the perfect setting for outdoor dining, entertaining, or simply relaxing at home. The home has been exceptionally cared for and is in great condition, offering four generously sized bedrooms, three full bathrooms, a two car garage, and attractive curb appeal. An additional highlight is the home's solar panel system, with no outstanding balance for the buyer to assume, providing the benefit of solar without taking over a solar loan. Meaning additional savings! You will also find that this home is conveniently located near Water spring Elementary, Water Spring Middle and Horizon High School. With its oversized homesite, tasteful finishes, inviting indoor outdoor living spaces, and convenient location within Storey Grove, this home offers an exceptional opportunity to enjoy the best of Winter Garden living.

11006 Robert Frost Drive, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Harvest/Ovation Ph 2 SubDv. ⋅ 34787 Zip Code

A truly exceptional luxury residence in the highly desirable **Harvest at Ovation community of Winter Garden**. Professionally designed and curated by a team of renowned **architects and interior designers**, this magazine-worthy home showcases sophisticated interiors, premium finishes, elegant décor, and exceptional attention to detail throughout. Every space has been thoughtfully designed to create a refined yet comfortable living experience, with **designer-selected furnishings and décor available for negotiation**. A standout feature is the **fully finished private studio above the garage**, complete with a full bathroom, walk-in closet, and independent access—perfect as a guest suite, executive office, private workspace, or additional living space. The gourmet kitchen features premium finishes and a state-of-the-art smart double-door refrigerator with internet connectivity. Enjoy Florida living in the screened outdoor area with mosquito protection, electric retractable awning, outdoor grill, and fenced yard. Additional upgrades include whole-home water filtration, premium kitchen water purification, epoxy garage flooring, LED ceiling lighting, and paver waterproofing. Ideally located near **excellent schools, shopping, dining, major highways, and Central Florida attractions**. **A rare opportunity to own a fully designed and beautifully curated luxury home where architecture, interiors, and lifestyle come together seamlessly. This is a home that truly needs to be experienced in person.** **Upgrades are negotiable: solar panels, whole-house water purification system, electric vehicle charger, furniture, and internet-connected double-door refrigerator.

16192 Honey Harvest Street, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Southern Pines SubDv. ⋅ 34787 Zip Code

**Click the Virtual Tour Link for 3-D walk-through tour** Welcome home to this well maintained FIRST FLOOR 3-bedroom, 2-bath condominium in Winter Garden, ideally located near shopping, dining, and with easy access to major roadways for trips to the airport and theme parks. This corner unit condo offers convenience to parking and features an open floor plan with spacious living room plus a den - perfect for a home office or flex space. The kitchen includes a breakfast bar, pantry, and convenient laundry room just through the kitchen. The split floor plan provides privacy to the primary suite with walk-in closet, linen closet, and en-suite bathroom. Additional bedrooms also feature walk-in closets and the hallway bathroom has an extended vanity for extra space and storage. Residents of Southern Pines Condos enjoy an exceptional array of amenities such as a pool and spa, outdoor kitchen, clubhouse with theater, office space and billiards, indoor basketball and racquetball courts, fitness center, playroom, covered outdoor playground, tennis and beach volleyball courts, and a car wash station. The gated community's HOA fee includes cable, internet, water, sewer, trash, and exterior maintenance, making for a truly low-maintenance lifestyle. Call for a showing today!

200 Southern Pecan Circle Unit 104, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

NEWLY UPDATED LAMINATE FLOORING THROUGHOUT THE MAIN AREAS, BEDROOMS, AND STAIRS!!!! kITCHEN AND BATHROOMS HAVE CERAMIC TILE!!!! This amazing ready to move in 2 bed / 2 bath condo in the pristine gated community of Southern Pines with a lot of amenities. Located in the heart of charming Winter Garden and only 15 miles to Orlando. Condo Includes: 1 car GARAGE - Bonus room which is attached to living room, Walk-in closets in both bedrooms and In-unit laundry closet. Community Features Include: Water, internet, exterior & community maintenance included, amenities: Oversized Swimming pool and gazebo lounge areas - Spa / Hot Tub, Fully equipped fitness center with attached playroom, Indoor Basketball Court & Racquetball Court, Outdoor Pickleball / Tennis Court & Beach Volleyball Court, Covered Playground, Outdoor Kitchen including charcoal grills, mini fridge, sink & vending machines, Carwash station, Easy to access mailboxes at front of the community. Schedule your showing today.

417 Southern Pecan Circle Unit 201, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Stunning 2-bedroom, 2-Bath condo on the second floor, 1276 sq ft, with new carpet in the bedrooms and stairs. All Appliances updated in the last few years, and the A/C is just a little over a year old. Walk to the pool, enjoy views of the retention pond, and be close to all the community amenities. Don't miss this gem?

143 Southern Pecan Circle Unit 206, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Stoneybrook West Un 06 SubDv. ⋅ 34787 Zip Code

WOW!!! OVER $90,000 RECENT PRICE REDUCTION!! BRAND NEW AC SYSTEM INSTALLED 7/2/2026 Experience refined Florida living in this beautifully enhanced home located within a highly desirable golf course community. The property offers both style and peace of mind with a roof replaced just five years ago and a recently sealed and painted exterior. Inside, the home is designed for both comfort and entertainment, featuring an immersive surround sound system throughout the main level and an impressive dedicated theater/bonus space. Every detail has been curated to elevate everyday living. Step outside to your own private retreat—an exceptional backyard showcasing a custom pool and spa with a striking grotto feature, creating the perfect setting for relaxing or entertaining guests year-round. Residents enjoy access to an array of resort-style amenities, including a clubhouse with dining, fitness center, tennis and basketball courts, beach volleyball, playgrounds, and an expansive community pool. Ideally situated just minutes from world-renowned attractions like Walt Disney World, with convenient access to major expressways and premier shopping and dining destinations nearby, this home offers the perfect balance of luxury, location, and lifestyle. One or more photo(s) have been virtually staged. PLEASE REMOVE SHOES BEFORE ENTERING THE HOME!

13412 Fox Glove Street, Winter Garden

1 Beds ⋅ 1 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Welcome to Southern Pines in the heart of Winter Garden. This well-maintained 1-bedroom, 1-bath upper-level condo offers a bright and functional layout with abundant natural light. The kitchen features granite countertops, ample cabinetry, and a practical layout that connects to the living and dining areas, creating a comfortable flow for everyday living. The open layout and high ceilings help maximize the space and give the unit an airy feel. The bedroom is comfortable and well-sized, offering a quiet and private retreat. This unit also includes an attached 1-car garage and additional storage, a valuable feature within the community. Southern Pines is a gated community with resort-style amenities including a pool, fitness center, tennis courts, basketball, racquetball, sand volleyball, playground, and clubhouse. The HOA covers lawn care, water, cable, and internet for added convenience. Ideally located near Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail, with easy access to SR-429, Florida Turnpike, SR-408, and SR-50. Daily conveniences are just minutes away, including Publix (approx. 3 minutes) and Costco (approx. 8 minutes). Make this property your home today.

131 Southern Pecan Circle Unit 201, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code

Virtually Staged. Beautiful 2-bedroom, 2-bathroom condo just under 1,300 sq ft in one of the most desirable areas of Winter Garden. Both bedrooms feature large walk-in closets, and the layout is exceptionally well designed, making the home feel spacious and comfortable. The unit COMES WITH A 1-CAR GARAGE, a rare and valuable feature. All appliances are BRAND NEW, including refrigerator, microwave, stove, and dishwasher. A washer and dryer are also included. The flooring has been completely renovated to elegant wood flooring throughout. The main living area offers a separate flex space that is PERFECT for a home office or a kids’ play area. Conveniently located next to the community car wash, with resort-style amenities that include an amazing clubhouse, pool area with barbecue grills, fully equipped gym, tennis courts, basketball courts, and more.

225 Southern Pecan Circle Unit 208, Winter Garden

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