Oakland FL Real Estate & Homes for Sale

Welcome to Oakland Trails! This better than new home is set on a premium lot with no rear neighbors. To many upgrades to mention!

Customized to pure-perfection, this impressive three-bedroom, two-bath, every detail in this single-story home has been cleverly planned. As you enter the home from the wrap-around porch, you'll take immediate notice of the efficient floor plan and attention to detail. Features such as wood laminate floors, 9' elevated ceilings, 8' interior doors, custom window treatments, beautifully detailed moldings, and bronze decor compliment the home's interior throughout. The gourmet kitchen is located at the heart of the home and features gourmet kitchen with KitchenAid appliances, an electric cooktop and convection oven, Quartz countertops, a geometrical natural stone backsplash and an oversized island. A bonus kitchen extension room is perfect for a coffee bar or wine room. Privately located on both sides of the home are comfortable bedrooms. The master retreat is bright and inviting, quietly tucked away from the other bedrooms within the home. The tranquil master bath offers walk in shower with rain shower head, his and her vanities, and two expansive walk-in closets. Built to provide a high level of functionality while also serving as a space primed for entertainment, the home offers a paved and screened lanai blurring indoors and out. The well manicured gardens are edged with concrete, providing both protection and beauty. The HOA dues include lawn care so there's no need to mow or care for the lawn. Located in Orlando's prime nature-lover communities with immediate access to the West Orange Trail and the Oakland Nature Preserve. Longleaf at Oakland residents enjoy access to a neighborhood park, playground, and community pool. The home is located within the golf cart district with convenient access to the Historic Downtown Winter Garden and an award-winning Farmers Market. Private showings are available - inquire today.

BACK ON MARKET TILL MARCH 24TH, 2023. Opportunity to own a Unique Property in The Beautiful Town of Oakland, Florida. A very short drive to downtown Winter Garden. This home has been a well-cared-for family home for multiple generations and properties like this Do Not come on the market often. The home needs minor updates to make this the perfect home. A new septic system was installed in 2023. The property has a separate apartment off the carport, which could be used as a Mother-In-law Suite or it can be rented for extra income. The Town of Oakland has a small town field while being so close to everything. This property is a Must See, before it goes pending, as these types of properties Do Not come available often.

Are you looking for direct access to nature without going too far? This practically brand-new home sits on a corner lot in the small historical town of Oakland. The location is prime with only 3 miles to the famous downtown Winter Garden to enjoy the weekly farmers market, the brewery, and plenty of great dining and shopping. You can also just walk across the street to hike through the Oakland Nature Preserve, or walk along or bike on the 22 mile West Orange Trail.This move-in ready home first welcomes you with a wrap-around porch that has a view of the trail and a built-in porch swing. The interior of the home includes a generous sized gourmet kitchen equipped with Kitchen Aid appliances, wine fridge, butler's pantry, and a large kitchen island perfect for coming together as a family. The kitchen opens to a gathering room with pocket sliding doors which allows plenty of natural light to flow in through this open floor plan. Completing the first floor there are 2 office spaces along with a bath, a walk in pantry, and a drop zone from the garage. The second floor is equally as spacious with 3 bedrooms, 2 full baths, and a loft which could be converted into a 4th Bedroom if needed. The upstairs also includes an upstairs laundry room with a laundry sink. You can transport yourself to the spa when you walk into the master bath which includes a super shower, bench seating, and a rain shower head. (Seller is willing to provide a credit to the buyer towards Lighting & Fans.) Some additional upgrades include a full home Vivint security system with cameras, full house gutters, wood look vinyl flooring, and an epoxied garage floor with built-in garage sink.The HOA includes lawn care, mulching, and shrub trimming. A community pool and playground is also provided for the homeowners. Longleaf at Oakland is conveniently located just under 30 minutes to downtown Orlando, 30 minutes to all the Orlando theme Parks and entertainment, and less than 5 minutes to the the Florida Turnpike. Call for your private showing today!

Welcome home to this beautiful 5-bedroom, 3-bathroom pool home located in the Westside Village community! At the front of the home is a great flex space that could be used as a work from home office or a great playroom for the little ones! As you continue in you'll find the formal dining room in the middle and the open concept kitchen and living room at the back of the home. This amazing space has 2 sets of sliding glass doors overlooking the backyard. Off the living room is a bedroom and full bathroom that is the perfect space for an in-law suite or for out-of-town guests! Upstairs offers an amazing and spacious loft that is lined with the rest of the bedrooms in the home. The master bedrooms features tray ceilings with a generous sized ensuite complete with a double sink vanity, soaking tub, and glass enclosed shower. Out the sliding glass doors is the spot you'll want to relax every night after a long days work. This rectangular pool offers a ledge for lounging before dipping down into the deep end for a cool swim. Schedule your private showing today, you wont want to miss out!

Check Virtual Tour 1. This immaculate, LAKEFRONT home in Oakland is waiting to take your breath away! Nestled on Hull Island with gorgeous views of Lake Apopka, this home exemplifies the tranquility and peace that Central Florida has to offer. Approaching the property, you'll immediately notice the beautifully manicured lawn and a spacious driveway, leading up to a 3 car garage. Upon entering, you'll be enveloped in the open, airy layout of the main floor. The beautiful staircase greets you at the entrance, accompanied with the high, tray ceilings and excess windows for ample natural lighting, to provide a warm welcome to your loved ones. The living room, kitchen, and dining room, seamlessly flow together, connected by the modern design choices and large windows that truly bring the outdoors inside. You're bound to fall head over heels for the stunning kitchen, with an oversized kitchen island, chic hardware, modern appliances, and excess space to tackle a meal of any size with absolute ease. The dining room lies right next to the kitchen, for added convenience when hosting, and includes large windows by the table so you can enjoy your meal with a magnificent view. Heading upstairs, you'll find the bonus loft space, perfect for a den, movie room, or so much more. You can certainly tailor this home to meet the needs of your family! All of the bedrooms include ample storage, space, and natural lighting so everyone can feel comfortable in their own space. The master bedroom is destined to be your own personal oasis, with stunning lake views, a gorgeous tray ceiling, abundant storage space, and a master bathroom that epitomizes luxury. Relax in the oversized soaking tub while looking out over the lake, enjoy the large walk-in shower with an opulent rain shower head, or get ready for a night out on one of the two spacious vanities. This bathroom will surely become your own spa! Heading outside, you'll find the shaded patio area and sizable backyard. This is the ideal place to host a family BBQ, soak up the warm Florida sun, or just appreciate the exquisite views all around you. Located conveniently close to major highways, attractions, downtown Winter Garden, and so much more, you'll never be too far from anything you could want or need. Don't wait on this amazing property, schedule your private showing TODAY!!

Welcome to Oakland Trails a Beautiful neighborhood located in the small but homey city of Oakland! This home is a spacious 5 Bedroom and 3.5 Bathroom home ready to be your forever home. Starting from the moment you step in you will be greeted by a cozy Great Room and a Dining Room, passing along you'll find yourself in a beautiful Kitchen and Living Room, the perfect spot to entertain. The First Floor includes: - Master Bedroom - Laundry Room (Inside) - 2 Car Garage Make your way upstairs to find a gorgeous loft and all the additional rooms! The upstairs is perfectly spaced to make the most use of the space while still being comfortable and not feeling compressed! Upstairs features a Bonus Room that can be used as an office/den/6th room. The home sits on a peaceful corner lot with neighbors to the right of the house only! (Solar Panels generate over 100% of electricity usage, you only have to pay the Electric Company taxes.

Welcome to this beautiful home, located in Oakland Trails in Winter Garden. Right as you walk in, you're greeted with a stunning view of the upgraded kitchen. This two year old home features 4 bedrooms, 2 and a half baths, and a gorgeous living area perfect for entertaining! Downstairs there is waterproof luxury vinyl throughout. The kitchen features upgraded appliances, and a gorgeous backsplash going up the whole wall behind the vent hood. The neighborhood of Oakland Trails is walking distance to the West Orange Trail. You're also within minutes of the Turnpike, which gets you to any part of central Florida very quickly! You'll also be able to get to downtown Oakland and downtown Winter Garden with just a short drive! You don't want to miss this opportunity for a nearly new construction home! Call today for your private showing!

!!! Move in Ready !!! Beautiful Townhome now available in the sought after community of Longleaf at Oakland. This lovely, like new 3 bedroom, 3 bathroom townhome features an en suite on the first floor. The kitchen boasts 42" cabinets, beautiful white back splash, stainless steel appliances and granite countertops. You'll love the open floor plan, overlooking the courtyard. On the second floor you'll find the spacious Owner's suite and guest bedroom each equipped with private bathrooms. This end unit open floor-plan home boasts an outside patio with a two car garage, and extended driveway. This townhome is located in Oakland, just minutes away from Downtown Winter Garden and adjacent to West Orange Trail and Oakland Preserve. The community features sidewalks with a playground, and community pool with Cabanas. This home will not last long, it was made just for you! Sellers are motivated!!

Located in the Town of Oakland a short drive from historic downtown Winter Garden. Great single-family home with NO HOA across from all new construction homes. Sits on a large double corner lot on a tree lined street, perfect for a first time home buyer or investor. There is also a detached shed. Park your boat, RV, etc and not worry about a HOA. Close to the Downtown Winter Garden, Oakland Nature Preserve, Fowlers Grove Shopping Mall, West Orange Bike Trail. Easy access to 429, FL Turnpike and 408. which is nestled in between Clermont and Winter Garden

LEASE PURCHASE OPTION AVAILABLE. No qualifying & No credit check! Minimal paperwork & quick closing!LOCATION, LOCATION, LOCATION...right in the center of Florida, North, South, East, & West, close to everything. It's only 2 minutes to get onto the Florida Turnpike. It's one of the largest & nicest homes in John's Landing & in the Town of Oakland! John's Landing is on the shores of 2,500 acre John's Lake, one of the most desirable upscale neighborhoods in Oakland/Winter Garden area & it's just 6 minutes drive to beautiful, quaint, & fun downtown Winter Garden, rated one of the best small towns to live in the USA, with festivals, restaurants, outdoor cafes, theater, water park, West Orange trail running thru the middle of the town, & the #1 rated Farmer's Market in the USA! You'll fall in love with this beautiful 5 bedroom, 4 bathroom waterfront screened-in pool & spa Old World Tuscan style decor estate home with 4,475 sq. ft. under air & a total of 5,500 sq. ft. under roof. All the rooms in the house are large! Watch Disney fireworks each night in the neighborhood 200 feet from the house. You'll love spectacular sunsets over the pond from your screened-in pool & spa in back of the house. A great house for entertaining. The large chef's kitchen has granite counters, 42" cherry cabinets, a center island for food prep, stainless steel appliances, a 3 person breakfast bar, & large dinette area to entertain guests. Enter your large 500 sq. ft. covered & screened-in lanai from the sliding patio doors in the family room or from the pool bath, & entertain guests while enjoying ice cold drinks watching a beautiful sunset over the lake or watching your loved ones play in the pool & spa. There's beautiful pond views from the downstairs second bedroom, pool bathroom - located right next to the second bedroom, both downstairs & upstairs large family rooms, the large kitchen & dining area, the downstairs utility room with a utility sink and cabinets, the upstairs master bathroom, & the third bedroom. The large master bedroom has a large walk-in closet & another area that could be converted to a closet or keep it as an office/storage/nursery area. The upstairs family room/loft area has a 4 speaker surround sound system & could be a media, family or game room. The fifth bedroom could serve as an in-law suite with a closet & a bathroom inside it or it could be a game room, media room, a home theater. or a man cave The home has tons of storage space. The oversized 2 car garage has storage cabinets, a refrigerator and a utility tub & the house has 5 extra large closets, in addition to each of the 5 bedrooms, & 3 of the 4 bathrooms having a closet. The friendly gated community of John's Landing has a boat ramp, dock & pier for fishing, a tennis court & playground. Watch Disney fireworks from the pier each night & the 4th of July. From the home it's just 17 minutes to Disney & Universal Studios, 18-20 minutes to downtown Orlando & Sea World, 25-30 minutes to the Orlando airport, & 5 minutes to Clermont. Friendly neighbors & a great location near 4 hospitals, restaurants, grocery stores, shopping, entertainment, FL turnpike, 429, 528, Hwy 50 & 27 just perfect for your family's new home! HOA info at: johnslandinghoa.com.

Large 4 Bedroom 2 Bathroom 3-way split floor plan with an Office and a 2 car Garage. Exclusively located in a gated community with easy access to Florida's Turnpike, 408, Hwy 50 to head in any direction. It is only 20 minutes away from Downtown Orlando and Universal Studios Orlando. In a private lake community, a boat ramp facing Johns chain of Lakes, great for fishing and skiing in a lake of more than 2,417 acres.