Winter Garden/Oakland Homes with Park/Greenbelt View

Winter Garden/Oakland Homes with Park/Greenbelt View

Welcome to the enchanting neighborhoods of Winter Garden and Oakland, Florida, where lush landscapes and charming communities await you. Nestled just a stone's throw from the vibrant city of Orlando, this picturesque region offers a delightful blend of small-town charm and modern conveniences.

Winter Garden is renowned for its historic downtown, featuring quaint boutiques, delectable dining options, and a thriving farmers' market that brings the community together every Saturday. With its beautiful parks, scenic trails, and warm, welcoming atmosphere, it’s no wonder that Winter Garden has become a sought-after destination for families and individuals alike.

Oakland, a neighboring gem, boasts a rich history and a close-knit community feel. Here, you’ll find stunning homes with breathtaking views of parks and greenbelts, perfect for those who appreciate nature’s beauty. Imagine waking up to the serene sight of lush greenery and vibrant flora right outside your window, providing a tranquil backdrop for your daily life.

The homes in this region are designed to embrace the outdoors, with many featuring spacious backyards and easy access to nearby parks. Whether you’re looking for a cozy single-family home or a modern townhouse, Winter Garden and Oakland offer a variety of options that cater to diverse lifestyles.

Living in Winter Garden and Oakland means not only enjoying the comforts of home but also embracing an active lifestyle with endless opportunities for outdoor recreation. From hiking and biking to picnicking in the park, this region truly embodies the best of Florida living. Discover your dream home with a park or greenbelt view in this idyllic community today!

Newest Winter Garden/Oakland Homes with Park/Greenbelt View

$359,999
3 Beds ⋅ 3 Baths ⋅ Orchard SubDv. ⋅ 34787 Zip Code
Some photos are Virtually Staged. WELCOME to a HOME that truly stands out in THE ORCHARD, a desirable GATED COMMUNITY in WINTER GARDEN! This beautifully updated 3-BEDROOM, 2.5-BATHROOM TOWNHOME is perfectly positioned with NO REAR NEIGHBORS and a BEAUTIFUL OPEN GREEN SPACE BEHIND THE HOME, offering a peaceful and private setting. From the moment you arrive, the inviting PRIVATE ENTRYWAY and spacious ATTACHED 2-CAR GARAGE set the tone for the comfort and convenience this home offers. Step inside to discover NO CARPET ON THE FIRST FLOOR, UPDATED LAMINATE FLOORING, and numerous recent updates throughout. The home features NEW LIGHT FIXTURES AND CEILING FANS (2026), NEW FAUCETS (2026), and NEW CARPET UPSTAIRS (2026). Major systems have also been thoughtfully updated, including a NEW HVAC SYSTEM (2025) and ROOF (2020). The WASHER AND DRYER (2024) add even more value and convenience. The open-concept main living area seamlessly connects the living room, dining area, and kitchen, creating a warm and welcoming space for both everyday living and entertaining. The kitchen features GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, ABUNDANT CABINETRY, a LARGE WALK-IN PANTRY, and a BREAKFAST BAR WITH PENDANT LIGHTING. A versatile FLEX ROOM just off the main living area provides endless possibilities and can easily serve as a HOME OFFICE, PLAYROOM, EXERCISE ROOM, OR ADDITIONAL SITTING AREA. A convenient HALF BATH WITH UPDATED FIXTURES, large storage closet, and direct access to the garage complete the first floor. A DEDICATED LAUNDRY AREA adds even more convenience to the home’s thoughtful design. From the dining area, sliding glass doors open to the PEACEFUL BACKYARD SETTING, where you can relax and enjoy the expansive green space and the added privacy of NO REAR NEIGHBORS. Upstairs, the NEW CARPET INSTALLED IN 2026 continues into the spacious loft, currently used as an office and complemented by additional cabinetry. The generous PRIMARY SUITE features a MASSIVE WALK-IN CLOSET WITH A WINDOW and a private ensuite bathroom offering DUAL SINKS, a STANDING SHOWER, SEPARATE JETTED SOAKING TUB, and PRIVATE WATER CLOSET. Two additional bedrooms are thoughtfully located on the opposite side of the primary suite and share a full bathroom featuring a TUB AND SHOWER COMBINATION. The HOA COVERS THE EXTERIOR OF THE HOME, LAWN MAINTENANCE, AND COMMON AREAS, providing added convenience and peace of mind. Residents of THE ORCHARD enjoy GATED SECURITY, a TRANQUIL COMMUNITY POOL, and PLAYGROUND, all in a prime WINTER GARDEN LOCATION just minutes from shopping, dining, top-rated schools, and the charm of DOWNTOWN WINTER GARDEN. TASTEFULLY UPDATED, WELL-MAINTAINED, AND MOVE-IN READY, this townhome offers an exceptional combination of STYLE, COMFORT, PRIVACY, AND CONVENIENCE, with many of the major updates already completed for you. Come see why you will love calling THE ORCHARD HOME!

242 Winter Nellis Circle, Winter Garden
$419,999
3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code
Storey Grove **YES IT HAS A BACKYARD!!*BACKS TO GREENSPACE!!** 2023 built ** Open floorplan * Beautiful wood ceramic tile entire 1st floor ** Attractive tv wall wood accent inlay in the family room ** White kitchen cabinetry with quartz counters and large cooking island ** All bedrooms are on the 2nd floor ** Nice size +/-16x20 brick paver patio area and 2 car detached garage ** Great RING security system, RING cameras, doorbell and door and window sensors ** Tesla EV power outlet is already in place in the garage ** Overhead storage racks in the garage are included ** Storey Grove community amenities include a huge resort style community pool, fitness center, basketball courts, 2 children's playground and green space area. Landscaping and exterior paint included in the HOA. Room measurements are from builder floor plan. Buyers to verify all room measurements.

10648 Words Drive, Winter Garden
$239,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort & Spa SubDv. ⋅ 34787 Zip Code
Exceptional opportunity to own a spacious top-floor 3-bedroom, 3-bathroom condo at The Grove Resort & Water Park, just minutes from Walt Disney World! This fully furnished 1,544 sq. ft. “Sable” floor plan offers an ideal combination of personal vacation use and income-producing potential through The Grove’s professionally managed hotel rental program. Located on the 7th and top floor of Building 1, the condo features a spacious split-bedroom layout, three full bathrooms, a well-equipped kitchen with granite countertops, comfortable living and dining areas, and a screened balcony with elevated views. The Grove delivers the complete Orlando resort experience with Surfari Water Park featuring water slides, a lazy river, splash areas and private cabanas, multiple onsite dining options, a full-service spa, fitness center, arcade, and a 20-acre activity lake offering fishing and water activities. When you're not enjoying the condo yourself, the turnkey rental program provides professional management for vacation rentals. Whether you're looking for your own Orlando getaway or a furnished vacation rental investment near Disney, this top-floor 3-bedroom residence offers an outstanding opportunity at one of Central Florida's most amenity-rich resort destinations.

14501 Grove Resort Ave Unit 1707, Winter Garden
$1,170,000
5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 5 SubDv. ⋅ 34787 Zip Code
Welcome home to this like-new luxury home in Lakeshore Preserve, the highly desirable community in Horizon West (West Orange County). Great location just off the 429 Western Beltway providing easy access to Orlando and Tampa, and less than 8 miles to Disney parks. You can even view the Disney fireworks nightly from this neighborhood. Wonderfully situated on one of the largest Executive Home sites with views of the green space in the back and a pond across the street, the Toll Brothers Gardenia Model is sure to please the pickiest buyers. This floor plan of just under 4200 sf offers 10' ceilings, 2 primary suites, 3 additional bedrooms, an enormous bonus room, 4 1/2 bathrooms, an extended screened patio downstairs and screened balcony upstairs to enjoy the views and outdoors. Attractive tile roof, tankless water heater, low-e windows and natural gas provide the maximum energy efficiency. Beautiful upgrades are found throughout the home starting with the luxury vinyl plank flooring in all the downstairs living areas. The well-appointed kitchen features an extended island with eating area, upgraded appliances and fixtures, convection oven, deep farmhouse sink and plenty of cabinetry. Off the kitchen is the butler's pantry and walk-in pantry leading to a formal dining room. Entertaining is a breeze with the open floor plan combining the kitchen with the family room with 3 huge sliding doors opening to the oversized brick-paver screened patio. The downstairs primary suite is spacious and works well for multi-generational households. The upstairs primary suite is even larger and its luxury, spa-like bathroom is like no other with a custom stand-alone 7' tub, oversized frameless shower with multiple shower heads, and 2 walk-in closets with custom organizers. A 22' x 18' loft separates the primary bedroom from the remaining 3 bedrooms and 2 additional full bathrooms. Come enjoy the Lakeshore lifestyle and amenities including clubhouse where numerous social activities are held to network with fabulous neighbors, a resort-style pool, fitness center, volleyball court, playgrounds, dog park, and canoes to enjoy Panther Lake which wraps around the clubhouse. The HOA fee includes grounds maintenance, 1 gig internet, cable, sidewalk pressure washing, and all amenities. Make your appointment to view this one in person. It's even more beautiful than the photos.

8222 Topsail Place, Winter Garden
$989,000
4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to 14038 Jomatt Loop, where impressive curb appeal, spacious living, and exceptional outdoor entertaining come together. This home is located just steps from A rated schools, has fresh exterior paint, and a large driveway with 3 car garage. Inside, the spacious open floor plan creates an inviting flow between the main living areas, offering plenty of room for everyday life and entertaining. A dedicated theater room provides the perfect setting for movie nights, sporting events, and unforgettable gatherings. Step outside and discover your own private retreat. The beautiful pool, surrounded by a freshly screened lanai, creates an ideal space for relaxing, entertaining, and enjoying the Florida lifestyle year-round. A durable metal fence adds both privacy and peace of mind while complementing the beautifully landscaped property. For added convenience, the home is equipped with a state-of-the-art security system. From its attractive exterior and expansive lot to its upgraded outdoor living spaces and versatile interior, this exceptional home offers the perfect blend of comfort, style, privacy, and entertainment. Schedule your private showing today!

14038 Jomatt Loop, Winter Garden
$468,000
3 Beds ⋅ 2 Baths ⋅ Oak Park At Winter Garden SubDv. ⋅ 34787 Zip Code
Located in the desirable charming golf cart community of Oak Park within a couple blocks of walking distance (or golf cart) to historical Winter Garden vibrant downtown with dining, boutique shopping and entertainment featuring a theatre and an award-winning farmers market. Then golf cart over to Newton Park on Lake Apopka featuring a boardwalk, boat ramp; playground, picnic areas along with a view of fabulous sunsets This well built cement block Maronda home offers a blend of charm and convenience with low HOA dues, and can be easily updated. A fully detailed Maronda Home original purchase package with survey, and an album of construction photos are available. Step out of this home into a wonderful screened solar heated pool and covered lanai for year-round enjoyment. The almost third acre overlooks the scenic well maintained Veterans Park offering acres of a variety of sports (including 10 pickle ball courts), playgrounds, picnic areas and green fields with wooded areas. The backyard is fenced on 3 sides and easily fenced and gated on each side for privacy. Within the wooded area in the back of the lot is a large attractive storage shed. Hop on the scenic West Orange Trail just minutes from this home for a walk, run or bike ride. Commuting via the 429 and the Florida Turnpike gives easy access to all of Central Florida and its theme parks.

665 Stevelynn Circle, Winter Garden
$299,000
Arrowhead Lakes SubDv. ⋅ 34787 Zip Code
Opportunity to own a ready to build spring fed lakefront land. 11 minutes to Disney World. 14 minutes to Orange County National Golf Center and Lodge.A2 zoning. A+ schools. No HOA. Established neighborhood. Well, Septic, Electricity, Fishing Dock, Boat Ramp, Shed, Private Gate are all ready and permitted. All you need is the Architectural and Engineering plans. Farmland Rural District, which allows for agricultural uses, single-family homes, and modular dwellings. Property is being sold As-Is, Where-Is. Buyer and buyer’s agent to conduct their own due diligence to verify all property information, including utility access, zoning, setbacks, and land use possibilities.

17101 Arrowhead Boulevard, 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
$834,999
7 Beds ⋅ 4 Baths ⋅ Verde Park Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to 16004 Ollivet, an exceptional residence where thoughtful design, high-end upgrades, and everyday functionality come together in one of Winter Garden's most desirable communities. Meticulously maintained and beautifully appointed, this move-in-ready home offers the perfect balance of elegant living, modern convenience, and timeless style. From the moment you enter, you'll appreciate the bright, open floor plan, soaring ceilings, and abundance of natural light that create an inviting and spacious atmosphere. Designed for both entertaining and everyday living, the expansive main living area flows seamlessly into the dining space and gourmet kitchen, making it easy to host family gatherings or enjoy quiet evenings at home. The chef-inspired kitchen is the heart of the home, featuring abundant cabinetry, generous countertop space, a large center island, quality appliances, and ample storage. Whether you're preparing a weeknight dinner or entertaining guests, this space offers both beauty and functionality. The spacious primary suite serves as a private retreat, offering a relaxing escape at the end of the day. One of its standout features is the professionally designed custom walk-in closet, providing exceptional organization, premium built-ins, and a luxurious boutique-style feel. The en-suite bathroom complements the space with modern finishes. A versatile flex room adds even more value to the home and has been enhanced with custom built-in cabinetry, making it an ideal home office, executive workspace, library, study, craft room, or media room. The custom storage solutions maximize functionality while adding a design element that sets this home apart. The additional bedrooms are generously sized and thoughtfully positioned to provide comfort and privacy for family members or guests. Every room reflects the pride of ownership found throughout the home. One of the home's rare and highly desirable features is the four-car tandem garage, offering exceptional flexibility and abundant space for multiple vehicles, a golf cart, recreational equipment, a workshop, fitness area, or additional storage. The tandem configuration provides even more usable garage space while maintaining a clean and organized feel. Step outside to the covered lanai, where you can enjoy your morning coffee, unwind after a long day, or entertain family and friends while overlooking the backyard. The outdoor living space provides the perfect extension of the home's interior. Conveniently located near Historic Downtown Winter Garden, Horizon West, shopping, dining, entertainment, parks, walking trails, major highways, and Central Florida's world-famous attractions, this home offers both convenience and an exceptional lifestyle. With its designer upgrades, custom built-in features, spacious open floor plan, rare four-car tandem garage, and outstanding location, this home truly stands out. Every detail has been thoughtfully curated to create a residence that is as functional as it is beautiful. Schedule your private showing today and experience everything this remarkable property has.

16004 Ollivett Street, Winter Garden
$480,000
2 Beds ⋅ 2 Baths ⋅ Grova Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park, a luxury vacation condo-hotel community offers owner privacy and convenience. Located 5 minutes from Walt Disney World, ownership of the largest 2-bedroom provides a family friendly place to vacation and relax. Let's discuss more about this 2B When you step through the door, you enter directly into the living space. The unit features in-unit laundry, with full-size washer and dryer. The kitchen is well-equipped with all major appliances, so you can certainly cook here if desired. The living space is spacious, and also includes a dining area. You can be making $ on the day of closing! Financial statements are available! Please note that this is a condo-hotel, so you could not live here full time due to zoning restrictions

14501 Grove Resort Avenue Unit 3425, Winter Garden
$849,000
5 Beds ⋅ 5 Baths ⋅ Osprey Ranch-Ph 1 SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Welcome to one of the most beautifully designed homes in Horizon West, nearly 3700 square feet of luxury living space, and only 4 minutes from Disney World, Firework views nightly. This house is a MUST SEE. The open-concept floor plan includes an expansive great room that flows seamlessly to the covered lanai and spacious backyard. Perfectly positioned to capture breathtaking sunset views over open farmland. There is plenty of room to build your dream pool, and there are no rear neighbors! Built less than 2 years ago, this exceptional 5-bedroom, 4.5-bath residence offers spacious rooms, stunning modern farmhouse finishes throughout, and ample storage (a premium in Florida). From the moment you step inside, the home delivers an unforgettable WOW factor. Anchored by an oversized island and a designer gourmet kitchen with a gas range for any chef’s delight. The stellar floor plan features premium cabinetry, quartz countertops, and premium fixtures. There are three ensuite bedrooms, including a spacious primary suite, plus two secondary ensuite spaces. One of these ensuite spaces is conveniently located downstairs, making it ideal for guests or multigenerational living. Community amenities include: Pool, Splash Pad, Playground, Hiking & Biking Trails. Perfectly situated in the heart of Horizon West, this home is within walking distance of Flamingo Crossings shopping and dining, and the brand-new Ovation Elementary School. Convenient access to Hamlin, downtown Winter Garden, MCO, major roadways, shopping, dining, and entertainment make this location truly hard to beat. A rare combination of design, quality, functionality, views, and proximity to Disney. This is Central Florida luxury living at its best!

15652 Gentle Rain Drive, Winter Garden
$525,000
3 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to Oakland Trails, one of Oakland’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and location. Built in 2018, the home features a bright, open-concept floor plan with spacious living areas, a modern kitchen, and plenty of room for both everyday living and entertaining. Step outside and enjoy all the amenities that make Oakland Trails so special, including a resort-style community pool and playground. Outdoor enthusiasts will love being just minutes from the renowned West Orange Trail, offering miles of scenic paths for walking, running, and biking through some of Central Florida’s most beautiful landscapes. Conveniently located near historic downtown Winter Garden, shopping, dining, and major roadways, this home combines small-town charm with everyday convenience. Whether you're relaxing at the pool, exploring the nearby trail system, or enjoying all that the area has to offer, this property delivers the Florida lifestyle you've been looking for.

2241 White Feather Loop, Winter Garden
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