Courtesy: LUXE PROPERTIES LLC
305-809-7650
NO HOA! VERY LARGE LOT! Discover your next home at 131 Ryan Ct in charming Oakland, FL. This well-maintained 3-bedroom, 2-bathroom house features beautiful wood-look tile floors throughout the entire home. Recent updates make this property move-in ready. The roof was replaced in 2021, followed by a new AC system in 2020, All new duct work in 2026, Septic pumped 2026, All weather porch windows 2026, new windows in 2023, and a brand-new water heater in 2024. The kitchen showcases wood cabinets paired with elegant quartz countertops installed in 2025, complemented by stainless steel appliances. The home's standout feature is the screened porch that runs the full length of the house, perfect for relaxing while overlooking the spacious backyard. This outdoor space offers plenty of room for entertaining, gardening, or simply enjoying Florida's beautiful weather. Location is key with this property. Situated in the heart of Oakland, you'll be close to local favorites including a coffee shop, florist, and cafe. The popular West Orange Trail is just a short distance away, ideal for biking, walking, or jogging. Downtown Winter Garden is nearby, offering additional dining and entertainment options. Daily conveniences are easily accessible with shopping centers and restaurants located throughout the area. This location provides the perfect blend of small-town charm and modern amenities. Whether you're looking for your first home or your next home, this Oakland property offers comfortable living in a great neighborhood The combination of recent improvements, outdoor living space, and prime location makes this house a great opportunity for your next chapter.
Courtesy: BHHS FLORIDA REALTY
407-876-2090
*** A RARE Offering in Oakland Park Custom-Built Luxury ONE-STORY Living *** An exceptional opportunity to own a custom-built residence in the highly sought-after community of Oakland Park, where timeless architectural details, refined finishes, and an extraordinary setting come together. This beautifully appointed 4 bedroom, 3.5 bath home with mudroom and OVERSIZED garage (2.5), with more than 700 square feet of space, offers a highly desirable feature rarely found in Oakland Park: a thoughtfully designed, single-story floor plan with TWO spacious PRIMARY suites. Situated on a premium corner lot, nearly a QUARTER acre, the property enjoys an exceptional sense of privacy, with mature oak trees, no rear neighbors, and a neighboring park, providing additional open space and lasting privacy. Inside, soaring vaulted ceilings, stunning WOOD flooring, elegant crown molding, a cozy FIREPLACE, and an impressive collection of custom millwork, including shiplap accents and exposed timber details, establish a warm yet sophisticated aesthetic appearance. The heart of the home is an expansive, open-concept kitchen and great room designed for both everyday living and effortless entertaining. The beautifully appointed kitchen features custom-panel THERMADOR appliances, including a 6 burner GAS cooktop, built-in oven and microwave, a walk-in pantry, and a coffee bar conveniently connected to the formal dining room. A charming breakfast nook completes this exceptional gathering space. One of the home’s most distinctive features is the expansive screened-in courtyard, creating a seamless extension of the indoor living areas. Finished with elegant travertine pavers, this private outdoor retreat features a kitchen complete with a grill and sink, making it ideal for entertaining or simply enjoying the Florida lifestyle. The generous courtyard also presents an exciting opportunity for a future swimming POOL, allowing the next owner to further customize the space. A separate covered rear porch and welcoming front porch provide additional opportunities to enjoy the home’s beautiful surroundings. The primary suite toward the back of the home includes a comfortable sitting area and an oversized eight-foot sliding glass door opening directly to the courtyard. The luxurious en-suite bath offers a quartz-topped vanity, walk-in shower, and garden tub. The second primary suite features an adjacent full bath and its own courtyard access, ideal for multigenerational living, visiting guests, or an extended-stay retreat. Two additional bedrooms with walk-in closets are towards the back of the home along with a full bath. A conveniently located half bath serves the main living areas and has access to the courtyard. The home is a short GOLF-CART ride to Historic Downtown Winter Garden's award-winning restaurants, shopping, farmers market, and events. This golf-cart-friendly waterfront community offers two pools (one resort styled pool), a clubhouse, parks, playgrounds, dog park, lake-side walking trails, and access to the 22-mile West Orange Trail, with easy reach to interstate travels, golf, and world-renowned theme parks. More than a home, it is the Winter Garden lifestyle. A rare combination of one story custom craftsmanship, privacy, exceptional outdoor living, and an irreplaceable location along the West Orange Trail, this remarkable Oakland Park residence offers a lifestyle that is increasingly hard to find.
Courtesy: DOWN HOME PROPERTIES, LLLP
352-753-0976
Welcome to this well-maintained home in the gated community of John's Landing! With 4 bedrooms, 2.5 baths, a spacious bonus broom, and a separate office that could be converted back to a bedroom, there's plenty of room to make this home fit your needs. The Kitchen features a cozy nook for everyday meals, while the enclosed patio- with its built-in bar and entertaining area- is ready for relaxing or gathering with family and friends.The roof and water heater are approximately 3 years old. Enjoy the space, flexibility, and community amenities John's Landing has to offer. Come see if this homies the right fit for you!
Courtesy: LPT REALTY
877-366-2213
Beautiful 2022-built home in Hull Island featuring 5 bedrooms, 4 full bathrooms, approximately 3,781 heated square feet, a private pool, and a two-car garage. Open-concept living with a gourmet kitchen, quartz countertops, a spacious loft, and two primary suites, including one on the first floor. Community amenities include a pool, trails, playground, dog park, and private dock. Buyer to verify all measurements, HOA terms, and property details.
Courtesy: WEMERT GROUP REALTY LLC
407-743-8356
Virtually Staged. **WELCOME HOME** Pond views, beautiful upgrades, and an unbeatable location just minutes from Downtown Winter Garden! BUILT IN 2020 with FRESH EXTERIOR PAINT (2026), this SINGLE-STORY home in the charming Longleaf at Oakland community offers a sought-after floor plan, stylish finishes, and a fantastic location with no direct front or rear neighbors. A welcoming COVERED FRONT PORCH overlooks a peaceful community pond, creating a tranquil setting to relax and enjoy the view. Inside, LUXURY VINYL PLANK FLOORING flows throughout the home, complementing the light, bright, and OPEN LIVING SPACES. The home chef will appreciate the well-appointed kitchen featuring QUARTZ COUNTERTOPS, timeless cabinetry topped with crown molding, a gray ARABESQUE MOSAIC TILE BACKSPLASH, stainless steel appliances, a BUILT-IN OVEN and microwave, cooktop with vent hood, and a spacious ISLAND with PENDANT LIGHTING. A convenient BUILT-IN WORK SPACE just off the kitchen is ideal for a home office or homework station. The thoughtfully designed floor plan offers comfortable bedrooms and beautifully finished bathrooms with granite countertops and gray cabinetry, plus CUSTOM CLOSET built-ins in one of the secondary bedrooms. POCKET SLIDING GLASS DOORS open to the SCREENED LANAI, complete with roller shades for added comfort and privacy. Beyond the porch, a FENCED BACKYARD provides a rare bonus for this style of home, offering outdoor space while still enjoying the convenience of a 2-CAR REAR FACING GARAGE with epoxy flooring. Additional street parking is available out front. Even better, the HOA takes care of the lawn maintenance! Longleaf at Oakland is a quaint, welcoming community with a pool and playground just steps from your front door. Outdoor enthusiasts will love being just a 5-minute stroll from the West Orange Trail, while the shops, restaurants, farmers market, and charm of Historic Downtown Winter Garden are all less than 10 minutes away! Commuters will appreciate quick access to the Florida Turnpike, SR 50, and SR 429, with Lake Apopka, parks, shopping, and everyday conveniences all nearby. ZONED FOR TOP RATED SCHOOLS - Tildenville Elementary, Lakeview Middle, and West Orange High School. Enjoy the benefits of NEWER CONSTRUCTION, thoughtful UPGRADES, LOW MAINTENANCE LIVING, and a prime Oakland location without sacrificing proximity to everything Winter Garden has to offer. Schedule your tour today!
Courtesy: ALL REAL ESTATE & INVESTMENTS
407-917-8206
Pre-Construction. To be built. Experience custom living at its finest in this beautifully crafted J&J Building home, ideally located in the heart of charming Oakland. Offering 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this home combines thoughtful design with modern appeal. The primary suite is conveniently located on the main floor, providing a private retreat. Enjoy Florida’s year-round sunshine and entertain with ease in the outdoor summer kitchen, perfect for gathering with family and friends. Situated directly across from Speer Park which features pickle ball, a tennis court and a basketball court. Located just moments from Lake Apopka, the West Orand Trail, three miles to downtown Winter Garden, and steps from the charm of downtown Oakland, this home offers a unique blend of outdoor recreation, small-town character, and custom craftsmanship. Don’t miss the opportunity to make this exceptional property your own!
Courtesy: ALL REAL ESTATE & INVESTMENTS
407-917-8206
Under Construction. Discover the perfect blend of custom craftsmanship, modern style, and small-town charm in this beautifully designed J&J Building home. Featuring 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this distinctive residence offers a thoughtfully designed layout with the primary suite conveniently located on the second floor. Sleek vinyl windows add a contemporary touch, while the summer kitchen creates the perfect setting for outdoor entertaining and enjoying Florida living year-round. Ideally situated across from Speer Park where you can enjoy an active lifestyle featuring pickleball, tennis, and basketball courts. Just up the street from Lake Apopka, the West Orange Trail, three miles from downtown Winter Garden, and right next to charming downtown Oakland, this home offers a wonderful opportunity to enjoy the beauty of nature and the appeal of a welcoming community, all close to home. Experience the best of custom living in a location that truly stands out!
Courtesy: DALTON WADE INC
888-668-8283
CLOSE BY DECEMBER 31, 2026! Establish Florida residency now to potentially unlock increased Homestead tax savings under Amendment 3—NO 5-YEAR WAIT! Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direct access to local walking trails. Built in 2018 and impeccably maintained, this home features an open-concept layout with towering 10-foot ceilings throughout. The main level boasts gorgeous tile flooring, a built-in office desk, a convenient wet bar, and carefully curated interior lighting that enhances the home's warm character and sophisticated ambiance. The gourmet kitchen shines with 42-inch refinished maple cabinets, updated hardware, quartz countertops, a stunning center quartz island, and a striking ceiling-height marble backsplash. Upstairs, enjoy the warmth of bamboo stairs and beautiful bamboo flooring across all bedrooms, each equipped with walk-in closets. Additional notable upgrades include quartz countertops in all bathrooms, beautiful zebra blinds, a 2026 refrigerator, and an epoxy-finished two-car garage. Step outside to exceptional exterior enhancements added in 2025 and 2026, including striking exterior accent lighting that delivers incredible nighttime curb appeal and presence, a fully sealed paver driveway, a welcoming front porch with ceiling fans, and an extended paver pathway wrapping around the house. Practical features include a brand-new gutter system connected to a downpour drainage system, plus a reliable irrigation system. Located in a top-rated school district, this home places you moments away from the scenic Oakland Nature Preserve, community parks like Speer Park, vibrant local farmers markets, rich cultural attractions like the historic Garden Theatre, and nearby dining favorites. Don't miss this incredible gem!
Courtesy: OAK AVENUE REAL ESTATE LLC
407-720-5000
Under contract-accepting backup offers. Beautifully crafted by J&J Building, this exceptional 4-bedroom, 4.5-bath custom home combines thoughtful design, elegant finishes, and effortless indoor-outdoor living. Situated on a desirable corner lot, the home is filled with incredible natural light and offers a layout designed for both everyday comfort and entertaining. At the heart of the home, the stylish kitchen is complemented by a wet bar and a full scullery (back kitchen) with a second refrigerator, oven, sink and built-in pantry, creating the perfect blend of style and functionality. The main-level primary suite provides a private retreat, while three additional upstairs bedrooms each feature their own en-suite bathroom, offering comfort and privacy for family and guests alike. The downstairs office and upstairs loft area also provide flexible options to meet all your needs. The oversized attic storage with drop down stairs is perfect for all your seasonal items! Step outside to your own private oasis through the huge pocketing sliding glass doors, and enjoy the salt water pool, spa, and inviting outdoor living space with automated retractable screens—ideal for enjoying Florida living year-round. And the large garage has 2 EV plugs and 2 garage doors- 1 perfect for your golf cart! Just across the street, a beautiful pond provides a peaceful natural backdrop, with scenic sunset views and abundant wildlife adding to the home's special setting. Enjoy an exceptional lifestyle just steps from the West Orange Trail and within the Golf Cart District, offering convenient access to downtown Winter Garden's charming shops, restaurants, and vibrant community atmosphere. A rare opportunity to enjoy custom craftsmanship, beautiful surroundings, and an unbeatable location—all in one remarkable home.
Courtesy: LPT REALTY
877-366-2213
Welcome to this beautifully maintained, fully furnished, six-year-old townhome in the charming town of Oakland! Featuring 2 bedrooms, 2.5 baths, and a two-car garage, this home combines abundant natural light with thoughtful upgrades and inviting outdoor space. A covered front porch welcomes you into an open great room featuring Shaw luxury vinyl tile flooring, neutral tones, recessed LED lighting, and dual-pane Low-E windows with cordless faux wood blinds. The kitchen offers 42-inch cabinetry, granite countertops, a gray subway tile backsplash, and a spacious island with upgraded pendant lighting and a large undermount sink. Appliances include a Whirlpool Gold microwave, range, and dishwasher, along with an LG French-door refrigerator. A generous pantry with a California Closets shelving system keeps everything organized. The adjoining dining area features upgraded lighting and a full-glass door with built-in blinds leading to a private 19-by-15-foot paver courtyard—an inviting setting for outdoor dining or relaxing. A built-in desk nook with granite countertops, drawers, and cabinetry provides a convenient workspace. The first-floor laundry room includes a California Closets laundry station and access to under-stair storage, while a half bath is located off the stair landing. Upstairs, both spacious bedrooms offer walk-in closets and private bathrooms. The primary suite features a California Closets organization system with a built-in vanity. Its ensuite bath includes dual sinks, granite countertops, Moen faucets, a private water closet, and a tiled shower with decorative accents, frameless glass, and an upgraded showerhead. The second bedroom’s private bath features granite countertops and a tiled tub/shower combination with an accent inlay. The courtyard connects to the two-car garage, complete with epoxy flooring and a Bluetooth-enabled opener. Additional features include gutters, a Taexx built-in pest control system, Nest thermostat, Ring security system and doorbell, Alexa-compatible front porch lighting, and prewiring for ceiling fans in the great room and bedrooms. Enjoy community walking paths, a playground, and a pool, with lawn care included in the HOA. Conveniently located near the West Orange Trail, downtown Winter Garden, downtown Clermont, Florida’s Turnpike, and Winter Garden Village, this home offers easy access to shopping, dining, recreation, and major roadways.
Courtesy: LORI GILMORE REAL ESTATE LLC
407-402-2623
LOCATION, LOCATION, LOCATION. Located in the HEART of OAKLAND and steps from DOWNTOWN WINTER GARDEN! TWO QUANT AND HIGHLY DESIRED TOWNS offering FESTIVALS, FARMERS MARKETS, EVENTS FOR ALL OCCASSIONS! Come see this BEAUTIFUL, WELL MAINTAINED HOME BUILT IN 2022 WITH A CONSERVATION/PROTECTED PRESERVE VIEW in OAKLAND! This home looks like a BRAND NEW MODEL HOME! There will never be homes built across the street from you so in this location you only have homes built on ONE SIDE of the street making this STREET SO SPACIOUS! The home has an OPEN DESIGN and LUXURY VINYL PLANK THROUGHOUT most of the home! This ONE OWNER home has been maintained in pristine, LIKE NEW condition with SELLER ADDING OVER $90,000 IN CUSTOMIZATIONS to this home including being the ONLY HOME IN THE COMMUNITY with a CUSTOM BRICK ACCENT OPTION ON THE FRONT OF THE HOME. Home has a WATER PURIFICATION, FILTRATION, R.O. SYSTEM, CUSTOM CLOSET SYSTEMS, CUSTOM LAUNDRY ROOM, GARAGE FINISHED WITH EPOXY FLOORING AND SHELVING SUSPENDED FROM CEILING FOR TONS OF STORAGE Home also has TANKLESS GAS WATER HEATER AND GAS COOKING! This home has a beautiful kitchen with elegant choices, TONS OF CABINET SPACE, A CUSTOM-FINISHED WALK IN PANTRY, POTTERY BARN DRAPERIES and a CHEF’S DREAM for appliances. The home also has a beautiful covered and inviting front porch to welcome your guests and a large, covered back porch as well with a very private and beautiful backyard that has been IMMACULATELY MAINTAINED. The MASTER BEDROOM has two LARGE WALK IN CLOSETS, A HUGE WALK IN SHOWER IN THE MASTER BATHROOM AND A PRIVATE WATER CLOSET. The second floor has large guest bedrooms and a LARGE BONUS/MEDIA/GAMEROOM! COME LIVE IN THE HEART OF IT ALL YET TUCKED AWAY IN A PEACEFUL QUIET ENCLAVE on a PEACEFUL QUIET STREET. You will be located just steps from the WEST ORANGE TRAIL, a few minutes from HISTORIC DOWNTOWN WINTER GARDEN, 1 mile to the Oakland Nature Preserve, a few minutes to the Town of Oakland and parks, Less than 2 miles to the Florida Turnpike which makes getting anywhere easy, 6 miles to the WINTER GARDEN VILLAGE and steps to shopping, restaurants, boutiques and all! This home is in a HIGHLY DESIRED ADDRESS in the TOWN OF OAKLAND. Come visit this QUIET, FRIENDLY and SMALL NEIGHBORHOOD because you are sure to want to stay forever! Qualified buyers may receive a 1-year interest rate buydown for the first year paid for by the Seller's preferred lender when financing this home (subject to credit approval and program availability) also Seller Financing Available.
Courtesy: LA ROSA REALTY KISSIMMEE
407-930-3530
Discover a private retreat in Hull Island at Oakland, an intimate community of limited residences offering a peaceful, exclusive feel near charming downtown Winter Garden and the celebrated West Orange Trail. Enjoy community amenities and a dock for taking in sunrise along Lake Apopka. With no immediate rear neighbors or neighbors on one side, this home backs to a conservation area for added privacy and a natural backdrop. Featuring 5 bedrooms, 4 full bathrooms and 3,658 square feet, the home offers an open kitchen, a versatile loft and a primary suite with its own screened porch overlooking nature. A rear patio with pavers and a covered screened enclosure creates an inviting setting for relaxing and entertaining. Room to gather, space to unwind and a setting to enjoy. Schedule your private showing.
Courtesy: RC GROUP REALTY LLC
407-492-6778
Virtually Staged. This beautiful 4-bedroom, 2.5-bath home in the charming town of Oakland! Ideally located with no rear neighbors, this home offers comfort, privacy, and everyday convenience.Recent updates include new flooring and fresh interior paint in 2025, plus freshly painted exterior in 2026. Enjoy carpet-free living throughout and a tile roof that adds to the home’s curb appeal. Located in a community with excellent amenities, low HOA and NO CDD. this home offers easy access to major highways, making trips to Disney and other Central Florida attractions a breeze. The newly opened Costco is just outside the community, with shopping and everyday essentials close at hand. A wonderful opportunity to enjoy small-town charm in a convenient location!
Courtesy: LAKESIDE REALTY WINDERMERE INC
407-876-5575
CLOSING COST ASSISTANCE AVAILABLE! Set in Longleaf at Oakland, directly across from Oakland Nature Preserve and the 22-mile West Orange Trail, this END-UNIT TOWNHOME offers a rare combination of natural surroundings and everyday convenience. A covered front porch overlooking a large grassy area welcomes you home and provides a peaceful place to relax and enjoy beautiful Florida sunsets. ADDITIONAL WINDOWS fill the end-unit home with natural light and create a bright, open feel. UPGRADED luxury vinyl flooring flows throughout the first floor. The OPEN FLOOR PLAN brings the living spaces together, with spacious living and dining areas that flow naturally into the kitchen. UPGRADED 42-inch white cabinetry with crown molding, stone countertops, a tile backsplash, a generous island with additional seating and a LARGE WALK-IN PANTRY create an inviting and functional setting for everything from casual mornings to entertaining friends and family. Just beyond the main living area, a PRIVATE COURTYARD connects the home to the detached TWO-CAR GARAGE by a covered walkway. With the garage positioned separately from the home, the courtyard becomes a private extension of the living space for grilling, entertaining or unwinding outdoors. Offering 1,652 sf, the townhome features TWO BEDROOMS plus a large LOFT that can serve as a HOME OFFICE, MEDIA ROOM, PLAYROOM or additional living area, and 2.5 BATHROOMS. Both bedrooms are located on the second floor and have PRIVATE ENSUITE BATHROOMS, giving the second bedroom the comfort and privacy of a SECOND PRIMARY SUITE. The primary suite includes an expansive WALK-IN CLOSET, while the bathroom is finished with UPGRADED shower tile and an UPGRADED glass shower door. SMART HOME features, including a Ring doorbell, security camera and MyQ garage-door opener add everyday ease. ENERGY-EFFICIENT double-pane windows and a programmable Nest thermostat help keep energy use and monthly electric costs down. Tall oak trees enhance the community’s natural setting, along with a COMMUNITY POOL, PLAYGROUND and WALKING TRAILS. Just outside the community, you can spend mornings walking beneath the trees, head out for a bike ride or follow the WEST ORANGE TRAIL into HISTORIC DOWNTOWN WINTER GARDEN for dining, shopping and the award-winning Saturday Farmers Market. Here, you can feel connected to nature without leaving convenience behind. Florida’s Turnpike entrance is approximately one mile away, while everyday shopping, including the new Costco in Clermont, is less than 10 minutes from home. It is an ideal setting for enjoying a quieter community atmosphere while remaining connected to work, recreation and everything the surrounding area has to offer.
Courtesy: KELLER WILLIAMS WINTER PARK
407-545-6430
Welcome home to Hull Island, where thoughtful upgrades, a private preserve setting, and resort-style amenities come together. Extended driveway upgraded with builder. This beautifully maintained 3-bedroom, 2-bath home backs to protected conservation land with no rear neighbors. High ceilings, electronic shades, and abundant natural light give the home an open, airy feel. The chef’s kitchen features an oversized granite island, a gas stove, pot filler, 42-inch cabinets, and additional upper cabinetry for storage. Tile backsplash, built in conventional oven and microwave. From the kitchen, you can look out over the pool while preparing meals. The spacious primary bedroom has been updated to the larger size upgrade with the builder. Master bathroom features a double vanity and a very large walk in shower with dual showerheads and a built-in bench, providing both comfort and convenience. Built in 2024, this custom fully automated SALT WATER 7FT screened-in pool area and overhead waterfall is made for relaxing and entertaining. You can control everything for the pool and waterfall , the color, the raindrops you can make it heavy or light all from the fingertips of your phone. It includes a summer kitchen with a sink and a gas fire pit that you can control with your phone. The home also offers a washer and dryer, an electric tankless water heater, and a recently installed Generac natural-gas whole-house generator designed to turn on automatically during a power outage. This home also has an irrigation system heling you keep the landscaping looking its best year- round! This home also has a water softener! The HOA is $165 per month, with no CDD. Community amenities include a resort-style pool, playground, dog park, and a boardwalk leading to a dock and fishing pier on Lake Apopka. Residents also have a private entrance to the 120-acre Oakland Nature Preserve. Downtown Winter Garden, the West Orange Trail, farmers markets, shopping, dining, golf, and pickleball are all close by. Home built in 2021 builder: M/I Homes Of Orlando LLC With its preserve views, inviting outdoor space, and convenient location, and privacy this move-in-ready home is a rare find. The photos are not virtually staged—this home truly is breathtaking! Seller has an assumable mortgage at a low interest rate of 2.375%!!!
Courtesy: KELLER WILLIAMS CLASSIC
407-292-5400
A vaulted central living space carries the eye from the front dining room through an island kitchen to glass doors opening onto a garden-framed patio, giving this single-story Oakland home a natural indoor-outdoor rhythm. The kitchen serves as the everyday hub, with an expansive island, breakfast-bar seating, abundant cabinetry and clear sightlines that keep meal preparation connected to the main gathering area. Just beyond the living room, the open-air patio is arranged beneath pergola-style shade and surrounded by planted beds, creating an inviting place for morning coffee, outdoor meals or a quiet evening beneath the trees. The split-bedroom plan adds practical separation, positioning the primary suite apart from two secondary bedrooms and a full hall bath. Multiple windows and a tray ceiling shape the primary bedroom, while its en suite bath includes dual sinks, a separate tub and shower and a walk-in closet. Ceramic tile extends through the main living areas, kitchen and bathrooms, with carpet in the bedrooms and an interior laundry area supporting an easy daily routine. Set on a 0.28-acre corner lot with no HOA, the property combines open lawn, mature landscaping and room to enjoy the outdoors, while an attached two-car garage and broad driveway add useful parking and storage. Located in a golf cart-friendly community, you’ll enjoy easy access to downtown Winter Garden’s shops, restaurants and local events, along with the nearby West Orange Trail for walking and biking. This Oakland location offers a relaxed residential setting with convenient access to everything that makes the Winter Garden area so enjoyable.
Courtesy: HOMEVEST REALTY
407-897-5400
Virtually Staged. Welcome to 2470 Standing Rock Circle, a beautifully maintained Montclair model by Meritage Homes in the desirable Oakland Trails community. Offering 3,446 square feet, 5 bedrooms, and a spacious open floor plan, this home has been meticulously cared for and is truly move-in ready. The first floor features a bedroom with a full bath, providing a comfortable and private space for guests. The main living areas flow seamlessly together and include surround sound in the living room, creating an inviting space for everyday living and entertaining. Step outside to the extended covered lanai spanning the full length of the home, with additional pavers extending the outdoor living area into the fully fenced backyard. Upstairs, you'll find the spacious primary suite with a tray ceiling, three additional bedrooms, and an oversized loft currently used as a theater room, complete with surround sound. This flexible space is perfect for movie nights, a game room, home office, or additional living area. Adding even more value, the exterior of the home will be freshly painted prior to closing, and the garage floor will receive a fresh epoxy finish. Located in charming Oakland, residents enjoy convenient access to the West Orange Trail, Oakland Nature Preserve, and Lake Apopka, while being just minutes from Historic Downtown Winter Garden with its restaurants, shops, Plant Street Market, Farmers Market, and year-round community events. With easy access to shopping, dining, and major roadways, this home offers plenty of space in a fantastic Central Florida location.
Courtesy: EXP REALTY LLC
888-883-8509
Virtually Staged. Some homes are defined by finishes. Others are defined by a setting that simply cannot be recreated. Tucked along the shoreline of Lake Apopka in historic Oakland, this 3,887 square-foot custom residence offers something increasingly difficult to find in Central Florida: substantial living space, privacy, mature surroundings and expansive lake views, all just minutes from Winter Garden. The experience begins on the approach. Crest the hill toward Millholland Street and Lake Apopka comes into view before the home settles into its private setting below. Step through the front door and your attention returns immediately to the water. A dramatic two-story living space, sweeping wood staircase and expansive windows fill the home with natural light and lake views from nearly every room. The spacious floor plan features three bedrooms, three full baths, a dedicated office and a spacious upstairs loft/bonus room. The first-floor primary suite offers privacy, custom closets and stunning lake views. A second bedroom and full bath are also downstairs, offering flexibility for guests or multigenerational living. At the center of the home, the kitchen opens to the surrounding living spaces with a panoramic view of the lake. Portions of the interior retain its original character, presenting an opportunity to update the kitchen and baths to your own style while preserving the architecture and generous proportions of the home. The enclosed main-floor patio creates a comfortable living space extension overlooking the water. Both the upstairs bedroom and the loft with wet bar lead to a large open-air deck with elevated views across Lake Apopka. Approximately 52 feet of natural shoreline provides privacy and a front-row seat to the area's native wildlife- ospreys, bald eagles, herons and other birdlife. Intentionally maintained as a natural shoreline rather than a recreational waterfront, creating a peaceful buffer between the home and the lake. The oversized three-car garage is equally impressive. Designed as a serious workshop, it features built-in cabinetry and pegboard, numerous electrical outlets, a pneumatic system with quick-connect ceiling hose reels, and additional storage and a garage-attic winch. A large private driveway provides plenty of parking and easy turnaround. The property has also benefited from numerous improvements, including an architectural-shingle roof, replacement double-pane windows, French doors and sliding glass doors, an enlarged upper deck, newer water heater, cooktop, microwave and carpet, HVAC servicing, duct cleaning, electrical evaluation and corrective work, septic servicing, irrigation improvements, restored drainage swale and additional landscaping. The fireplace and chimney have also been serviced, along with extensive pest-exclusion work. Beyond the property, Oakland offers the oak-lined streets and small-town character that make this corner of Central Florida so distinctive. The West Orange Trail, Oakland Town Center, historic Downtown Winter Garden and Plant Street are all nearby, along with convenient access to shopping, dining and major roadways. Kitchens and bathrooms can be transformed. A private Lake Apopka setting, substantial custom architecture, two levels of outdoor living and views like these are much harder to replicate. Modernize what you want. Preserve what you love. The lake, the views and the setting are already here.
Courtesy: REAL BROKER, LLC
407-279-0038
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. Equipped with FULLY PAID-OFF TESLA SOLAR PANELS, this home offers massive utility savings with no additional lease or loan payments—pure modern efficiency from day one! 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!
Courtesy: HOMEVEST REALTY
407-897-5400
Welcome to this beautifully designed 4-bedroom, 3.5-bath home offering stylish upgrades and exceptional indoor-outdoor living in the charming Town of Oakland. From the inviting covered entry and brick-paver driveway to the bright, open interior, every space has been thoughtfully designed for comfortable everyday living and effortless entertaining. The impressive kitchen features abundant cabinetry, expansive countertops, stainless-steel appliances, a natural gas cooktop, built-in oven and microwave, subway-tile backsplash, and an oversized center island with generous seating. Fabulous pantry features custom shelving and refrigerator. The kitchen flows seamlessly into the spacious living area, highlighted by a dramatic floor-to-ceiling accent wall with a sleek electric fireplace and built-in cabinetry. The formal dining room offers soaring ceilings, abundant natural light, and an elegant statement fixture. The spacious first-floor primary suite provides a peaceful retreat with a tray ceiling and a luxurious ensuite bathroom featuring a large glass-enclosed shower, separate soaking tub, dual-sink vanity, huge walk-in closet and distinctive designer finishes. Upstairs, you will find three additional bedrooms and a versatile bonus room—perfect for a home office, media room, playroom, or additional gathering space. One of the upstairs bedrooms includes a private ensuite bathroom, providing an ideal arrangement for guests. Sliding glass doors open to a private, screened outdoor oasis featuring an extended brick-paver patio, covered dining space, multiple conversation areas, and a relaxing 8-person spa—perfect for enjoying Florida living throughout the year. A privacy fence enhances the peaceful backyard setting. Residents of Hull Island enjoy access to a community pool, dog park, playground, and picnic area. The neighborhood also offers convenient access to the Oakland Nature Preserve, 22-mile West Orange Trail, and downtown Oakland. Enjoy the town’s Thursday farmers market, Arts and Heritage Center, local coffee shop, and Speer Park, with vibrant downtown Winter Garden just minutes away. Conveniently located near major highways, theme parks, downtown Orlando, Orlando International Airport, restaurants, shopping, and hospitals, this exceptional Oakland home combines contemporary style, thoughtful design, and an outstanding Central Florida lifestyle. You're only an hours' drive to some of Florida's finest beaches. Schedule your private showing today!
Courtesy: REGENCY REAL ESTATE LLC
321-303-4539
FRONT PORCH CHARM, WEST ORANGE TRAIL VIEWS, AND A HOME FULL OF CHARACTER IN THE HEART OF OAKLAND! Start your mornings from the covered front porch and porch swing, taking in the peaceful surroundings and views of the West Orange Trail just beyond your front door. Step inside to soaring spaces, abundant natural light, and architectural details that immediately make an impression. A grand staircase leads to a striking bridge-style balcony overlooking the family room, while a beautiful brick gas-burning fireplace anchors the living space and creates a warm, inviting centerpiece for gathering and entertaining. Designed with both everyday living and flexibility in mind, the spacious floor plan features a formal dining room, dedicated office, bonus room, and enclosed sunroom offering even more space to relax and enjoy the Florida lifestyle year-round. A generously sized walk-in closet provides exceptional storage, while thoughtful features such as a central vacuum system add everyday convenience. Roof Replacement in 2025 and HVAC replacement in 2022 add peace of mind for years to come. Located within Oakland's golf cart district, this home offers extra garage space for your golf cart, bikes, and moreWhether you're enjoying coffee on the porch swing, relaxing beside the fireplace, or simply taking in the peaceful small-town atmosphere, this home offers a wonderful combination of space, character, and location in sought-after Oakland. Come experience the charm and lifestyle that make this community such a special place to call home!
Courtesy: GOYAL & DECOSTER REALTY
407-693-7403
Under contract-accepting backup offers. Under Construction. Rare opportunity to finish a custom AR Homes "Carrabelle" build exactly the way you want it - priced to reflect its current stage. 166 Hammock Preserve Loop is roughly three-quarters complete: framing, block construction, roof, windows, and drywall are in, and the home is currently paused at that stage. What's left is the fun part - flooring, cabinetry, fixtures, paint, and finishes - which means the next owner gets to select every surface in a 3,186-square-foot, four-bedroom, four-bath custom home instead of settling for someone else's choices. The Carrabelle plan delivers a two-story, open-concept layout on a 6,914-square-foot corner homesite in Oakland Park: a first-floor guest suite and flex room, a dramatic 21-foot foyer, an open kitchen and great room with decorative beams, a covered lanai and cabana with an open-air courtyard and fireplace, and a second-floor primary suite with a spa-style bath and walk-in closet. A three-car garage and an optional suite above it round out the plan. Full floor plan available on request. Sold AS IS. The original building permit has expired and is disclosed; a buyer will need to re-permit to resume construction. AR Homes has provided an itemized estimate to complete the home - available to serious buyers - along with the original plan set and specifications, so you're not guessing at scope. This is a straightforward, priced-to-reflect-its-stage opportunity for a buyer (or a buyer working with their own GC) who wants a real custom home in Oakland Park without paying new-construction-complete pricing for it. Located in the sought-after Oakland Park community, with tree-lined streets, walking trails, and community events, close to downtown Winter Garden's shops and dining. Cash, conventional, or construction/renovation financing. Buyer and buyer's agent to verify all information including HOA details, permit status, and completion costs. Seller makes no representations or warranties regarding the condition or completeness of existing work.
Courtesy: APPROVED PATRIOT REALTY LLC
386-661-8000
Welcome to this beautiful and impeccably maintained 4-bedroom, 2.5-bath home in the desirable Johns Landing community of Oakland! This exceptional family home offers space, comfort, flexibility, and all the features buyers are looking for. The spacious floor plan includes a large bonus room and an additional room currently being used as an office, which can easily be converted back to a bedroom to suit your family's needs. The heart of the home is the generously sized kitchen, complete with a convenient kitchen nook—perfect for everyday meals, morning coffee, and family gatherings. Wood and carpet flooring add warmth and character throughout the home. Step outside and prepare to be impressed by the enclosed patio, featuring a spectacular built-in bar and entertaining area that truly sets this home apart. It is the perfect place to relax, entertain family and friends, watch the big game, or create unforgettable memories year-round. This home has been lovingly cared for and is immaculate inside and out. The roof is approximately three years old, the water heater is approximately three years old, and the air-conditioning system was recently serviced approximately three months ago. Located in the gated Johns Landing community, residents enjoy an array of amenities and recreational opportunities. This is more than a house—it is a beautiful place to call home, with the space, features, and flexibility today's buyers desire. Come see it for yourself—you'll immediately appreciate the pride of ownership and everything this special home exemplifies. Schedule your private showing today; this one is truly worth seeing!
Courtesy: SOUTHERN PRESTIGE REALTY INC
407-614-3873
Virtually Staged. JUST REDUCED!!!!!!!!!!!!!!!!!!!!!! A well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 2019, this beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and 1,620 square feet of bright, open-concept living space designed for both relaxation and entertaining. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large and contemporary kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, with premium finishes that seamlessly flow into the main living and dining areas, making it ideal for both everyday living and entertaining. Upstairs, the primary suite serves as your private retreat, featuring an En-suite bath and ample closet space, alongside two additional bedrooms perfect for family, guests, or a dedicated home office. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community provides everything the Florida Lifestyle has to offer ! Living here means embracing an incredible Central Florida lifestyle. The Longleaf community features a sparkling resort-style pool with a cabana, a playground, and scenic walking paths. Best of all, you are just steps away from the historic West Orange Trail and the Oakland Nature Preserve, making outdoor adventures effortless. When you want to head out for dinner or shopping, the vibrant culture of downtown Winter Garden and the famous Plant Street Market are only minutes away. Plus, with quick access to major highways like the Florida Turnpike and SR-429, you are seamlessly connected to all of Orlando's world-class theme parks, dining, and entertainment. Don't miss the opportunity to make this beautiful turnkey property your own!
Courtesy: NUMBER 1 BROKER, LLC
407-566-3400
Welcome to 2471 Skystone Ct, located in the desirable Oakland area! This spacious two-story home offers a thoughtfully designed floor plan with 4 bedrooms, 3.5 bathrooms, a private study, upstairs game room, and a 2-car garage. The main level features a separate living room, a dedicated study perfect for a home office, and an open-concept kitchen overlooking the breakfast nook and expansive great room. Step outside to the covered lanai, ideal for relaxing or entertaining year-round. Upstairs, the generous primary suite includes a private bath and walk-in closet. Three additional bedrooms, a large game room/loft, and convenient upstairs laundry provide plenty of flexibility for family, guests, work, or entertainment. Enjoy the Florida lifestyle with access to a community pool and nearby bike and walking trails, perfect for outdoor recreation. Located in the charming Oakland area with convenient access to Winter Garden, major roadways, shopping, dining, and Walt Disney World, this home offers a great combination of space, community amenities, and location.
Oakland is located in Florida. Oakland, Florida has a population of 3,444. Oakland is more family-centric than the surrounding county with 42.26% of the households containing married families with children. The county average for households married with children is 31.51%.
The median household income in Oakland, Florida is $124,856. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Oakland is 37.1 years.
The average high temperature in July is 92.2 degrees, with an average low temperature in January of 46.8 degrees. The average rainfall is approximately 52.1 inches per year, with 0 inches of snow per year.
