Winter Garden/Oakland Homes with Buyer Approval Required Community Features

Winter Garden/Oakland Homes with Buyer Approval Required Community Features

Welcome to the enchanting community of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This charming region is a perfect blend of small-town warmth and modern conveniences, making it an ideal place to call home. With its lush landscapes, vibrant downtown area, and rich history, Winter Garden offers a unique lifestyle that appeals to families, retirees, and everyone in between.

Winter Garden is renowned for its picturesque streets lined with historic buildings, boutique shops, and delightful eateries. The nearby Oakland area complements this charm with its serene atmosphere and beautiful natural surroundings, including the stunning views of Lake Apopka. Residents enjoy a plethora of outdoor activities, from hiking and biking along scenic trails to fishing and boating on the lake.

For those considering a move to this idyllic region, the homes in Winter Garden and Oakland feature a variety of architectural styles, catering to diverse tastes and preferences. Many of these homes are situated within communities that require buyer approval, ensuring a harmonious living environment. These communities often boast exceptional amenities, including sparkling pools, fitness centers, and beautifully landscaped parks, fostering a sense of community and connection among residents.

With its excellent schools, proximity to major highways, and a thriving local economy, Winter Garden and Oakland stand out as a prime location for both new families and seasoned homeowners. Experience the charm and allure of this wonderful area—your dream home awaits in Winter Garden and Oakland!

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

$870,000
5 Beds ⋅ 5 Baths ⋅ Harvest/Ovation Ph 2 SubDv. ⋅ 34787 Zip Code
A truly special luxury residence in the highly desirable Harvest at Ovation community of Winter Garden. Professionally designed and curated by a team of high-end architects and interior designers, this magazine-worthy home features soaring ceilings, premium finishes, designer furnishings, elegant décor, and exceptional attention to detail throughout. A standout feature is the fully finished private studio above the garage, complete with full bathroom, walk-in closet, and independent access—perfect as a guest suite, additional apartment, executive office, or private workspace. 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 fully paid solar panels, whole-home water filtration, premium kitchen water purification, epoxy garage flooring, LED ceiling lighting, EV charger, and paver waterproofing. Ideally located near excellent schools, shopping, dining, major highways, and Central Florida attractions. **Designer furnishings and décor are negotiable.** A rare opportunity to own a beautifully designed luxury home where every detail has been thoughtfully perfected. This is one you truly need to see in person.

16192 Honey Harvest Street, Winter Garden
$249,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
$290,000
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
$275,000
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
$699,000
2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Phase 2 SubDv. ⋅ 34787 Zip Code
Welcome to this ELEGANTLY UPGRADED and nearly new 2-bedroom, 2-bath residence in the highly sought-after Del Webb Oasis of Winter Garden, a GUARD-GATED 55+ community where resort-style living meets everyday sophistication. Perfectly situated on one of ONLY TWO PREMIUM HOMESITES of its kind within the community, this exceptional property enjoys a truly rare distinction: an EXCLUSIVE SIDE EASEMENT that creates exceptional privacy, expanded green space, and a level of openness rarely found in community living, with no immediate neighbor on one side and convenient proximity to the clubhouse area. From the moment you arrive, the home impresses with its REFINED CURB APPEAL, lush landscaping, and a spacious 2-car garage enhanced with CUSTOM STORAGE SOLUTIONS. Inside, a bright OPEN-CONCEPT LAYOUT welcomes you with abundant natural light and meticulous attention to detail throughout every space. The Kitchen is a TRUE SHOWPIECE, equipped with premium stainless steel appliances, a GAS COOKTOP, BUILT-IN OVEN, a CUSTOM BUILT-IN PANTRY WITH PULL-OUT DRAWERS, generous cabinetry, and stone countertops, all seamlessly flowing into the living and dining areas. The Living Room has been elevated with an INTEGRATED SURROUND SOUND SYSTEM, creating the perfect setting for daily enjoyment and entertaining. The Primary Suite is a private retreat featuring a CUSTOM-DESIGNED WALK-IN CLOSET SYSTEM and a well-appointed en-suite bath with dual vanities, generous storage, and a walk-in shower. An additional SECONDARY BEDROOM provides comfortable accommodations for family or guests, while the DEDICATED DEN, enhanced with UPGRADED HIGH BASEBOARDS and RECESSED LIGHTING, offers the flexibility of a home office, hobby room, or formal sitting area. CUSTOM CLOSET SYSTEMS throughout ensure every space is as functional as it is beautiful. Step outside to where this property truly STANDS APART. The expansive SCREENED-IN LANAI opens to an EXTENDED OUTDOOR DECK and a fully appointed BUILT-IN OUTDOOR KITCHEN (BBQ Area), all framed by CUSTOM OUTDOOR LIGHTING, creating an exceptional outdoor retreat designed for year-round Florida living. Additional highlights include a WHOLE-HOME WATER FILTRATION AND SOFTENER SYSTEM, FRESH INTERIOR PAINT throughout, and additional RECESSED LIGHTING both inside and outside that elevates the home's ambiance day and night. Residents of Del Webb Oasis enjoy RESORT-STYLE AMENITIES, including a 12,000 SF clubhouse with coffee bar, lounge, and wine lockers, a sparkling pool, state-of-the-art fitness center, tennis courts, and a vibrant social calendar, along with included cable and internet, fostering the active and connected lifestyle that Del Webb is famous for. IDEALLY LOCATED in Winter Garden, you are just minutes from the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for boutique shops, dining, and a weekly farmers market. Enjoy outdoor recreation along the WEST ORANGE TRAIL, or take a short drive to WORLD-CLASS ATTRACTIONS including Walt Disney World Resort and Universal Studios. Convenient access to FL-429 and major roadways makes it easy to enjoy the very best of Central Florida. This exceptional residence offers a RARE OPPORTUNITY to enjoy elevated, low-maintenance living on one of the community's most coveted homesites, where every upgrade has been thoughtfully chosen and every detail meticulously executed. Homes of this caliber and setting are a TRUE RARITY in Del Webb Oasis. Now is the time, don't miss your chance to call this home.

15139 Canopy Cover Drive, Winter Garden
$275,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
This first-floor condo in the gated Southern Pines community offers 1,216 square feet of well-designed living space with an open floor plan, private outdoor area, and two full bathrooms. Making it a strong fit for first-time buyers, down-sizers, or investors. The layout connects the living area directly to the outdoor space, and both bedrooms provide solid closet storage. The kitchen offers ample counter space and cabinetry for everyday living. Southern Pines residents enjoy access to a pool and spa, fitness center, indoor basketball and racquetball courts, tennis and pickleball courts, a media room, billiards lounge, business center, BBQ area, car wash station, and playground. All within a secure, gated community. Located minutes from the West Orange Trail, Johns Lake, SR 408, and the Florida Turnpike, with top-rated Orange County schools nearby and Orlando International Airport 23 miles away. Winter Garden’s dining and retail corridors are within easy reach. Low-maintenance living with resort-style amenities in a location that works. Schedule your showing today.

1300 Eastern Pecan Place Unit 102, Winter Garden
$890,000
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Stunning home 4 bedrooms all suites, located in the Lakeshore community. This beautiful residence offers a perfect blend of modern elegance and comfort. House just has been used from Original owner twice a year since built as a second home, looks brand new! Fully upgraded Kitchen with High end Jen Air appliances, Quartz Waterfall Island countertop, upgraded cabinets and quartz countertops thru out the house.. Extensive custom Carpentry work thru out the house. Deep Lot with plenty of space for a large pool with pre wired and pre plumbing for a future summer kitchen. Residents enjoy resort-style amenities, including clubhouse, fitness center, resort-style pool and proximity to top-rated schools, shopping, and major highways.

8289 Topsail Place, Winter Garden
$279,900
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
$829,900
5 Beds ⋅ 3 Baths ⋅ Stoneybrook West Un 06 SubDv. ⋅ 34787 Zip Code
WOW!!! OVER $60,000 RECENT PRICE REDUCTION!! BRAND NEW AC SYSTEM INSTALLED LAST WEEK (7/2/26) 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
$235,000
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
$279,900
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
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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