Courtesy: THE REAL ESTATE COLLECTION LLC
407-656-7814
Welcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath residence located in the gated community of Johns Landing, offering private boat access to scenic Johns Lake. From the moment you step into the foyer, you’ll appreciate the soaring volume ceilings, tile flooring throughout the main living areas, and an abundance of natural light that creates a bright and inviting atmosphere. To the left, a spacious living and dining room combination provides an ideal setting for entertaining and offers convenient access to the kitchen. The kitchen is well-appointed with solid wood cabinetry, granite countertops, stylish backsplash, a breakfast bar, and stainless steel appliances. The kitchen opens to a generous living area featuring sliding glass doors that lead to a large paver patio with fruit trees—perfect for indoor-outdoor living and relaxing gatherings. The primary suite is thoughtfully tucked down the hallway and showcases engineered hardwood flooring, a walk-in closet, and a beautifully renovated en-suite bath. The primary bath features a standalone shower, garden tub, and dual vanities. Three additional bedrooms, a guest bathroom, and a laundry room complete the interior layout. Residents of Johns Landing enjoy resort-style amenities including basketball, tennis, and pickleball courts, a playground, an open dock with private boat ramp, and a gazebo. Upgrades include: Water Heater (2024), Roof (2018), Double Pane Windows and New Slider (2024). Conveniently located near downtown Winter Garden, downtown Clermont, downtown Oakland, and major highways, this home offers both tranquility and accessibility. Don’t miss the opportunity to enjoy lake-access living in this desirable community!
Courtesy: URBAN-O REAL ESTATE SOLUTIONS
407-822-1063
Welcome to this beautifully maintained home located in the gated waterfront community of John’s Landing, nestled along the scenic 2,600-acre John’s Lake chain. This property offers a blend of upgraded features, generous living spaces, and an exceptional community lifestyle. A brand-new roof will be delivered at closing, as the replacement process is already underway through the insurance company. Step inside to a bright foyer and sitting area, enhanced by custom in-wall built-ins, crown molding, and shutters or blinds in every room. Additional features include upgraded ceiling fans, a fire wood fireplace, an intercom system, pre-wiring for a security system, and a versatile Florida room that has been converted into a bar/game room area. A spacious bonus room offers flexibility as an office or optional 5th bedroom. The home also includes a 5-ton Carrier A/C system installed in 2020, offering reliable, efficient cooling. The kitchen features cherry wood cabinetry, stainless-steel appliances, and generous storage. The bathrooms are finished with cultured marble countertops, and the primary suite includes a luxurious Jacuzzi garden tub. Built-in attic flooring adds valuable extra storage. Sitting on an oversized lot, this property offers exceptional outdoor potential—ample space to build a large pool, or even create a guest house or independent efficiency (subject to county approval). The fully fenced backyard adds privacy and versatility for future projects. John’s Landing residents enjoy exclusive access to a private community boat ramp, tennis courts, and a playground, making it the perfect place to enjoy Florida living. The home also includes a 3-car garage and rests on a quiet cul-de-sac. Ideally located less than 5 miles from Montverde Academy, with quick access to the Florida Turnpike, SR-429, major shopping, dining, and daily conveniences.
Courtesy: MARK SPAIN REAL ESTATE
855-299-7653
One or more photo(s) has been virtually staged. Experience the height of Florida luxury in this stunningly renovated 5-bedroom pool home, nestled within an exclusive gated community featuring a private boat ramp and lake access. Boasting soaring ceilings, quartz countertops, and a striking panoramic landing, this residence blends architectural elegance with modern sophistication. Peace of mind is built-in with a brand-new roof, new A/C, and fresh designer paint inside and out. The main-level primary suite offers a serene escape, while the meticulously renovated garage has been transformed into a pristine, high-end showroom that must be seen to be believed. Outside, your private screened-in oasis features a sparkling pool and a lush backyard with a mature mango tree. Perfectly positioned for convenience, you are minutes from the Turnpike and SR 429, placing Downtown Orlando, world-class dining, and Disney’s magic less than 30 minutes away. This is more than a home; it is a rare opportunity for the discerning buyer to secure a premium lifestyle in a hidden lakeside gem. Your upgraded sanctuary awaits.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two laundry rooms, and a detached casita with a full ensuite—ideal for guests, in-laws, or extended stays. Inside, the home showcases elevated finishes at every turn, including Sierra Pacific windows—62 in total—filling the home with natural light, an impressive Euro-style 9'+ bifold slider, and a stunning gas fireplace anchoring the main living space. The chef’s kitchen boasts Wolf and Sub-Zero appliances, exquisite Quartzite counters in both the main and back kitchens, and a fully equipped back kitchen designed for effortless entertaining. A custom primary closet with lighted rods adds a boutique touch to everyday living. Outdoor living is equally exceptional. Enjoy a lap pool and hot tub, gas fire pit, and luxurious marble coping and pool decking, all beautifully framed by a $70,000 professionally designed landscaping package and a fully fenced yard for privacy. Additional upgrades include Sonos speakers, security system with cameras, clay tumbled pavers on the porches, and a Generac generator for added comfort and peace of mind. With a 4-car garage, impeccable craftsmanship, and a leaseback opportunity, this home offers the best of luxury and convenience. Furniture is negotiable, allowing you to tailor the space to your vision. Discover refined living in one of Oakland’s most desirable communities—this model home truly sets the standard.
Courtesy: UNLOCK REALTY GROUP INC
470-509-3301
Welcome to this stunning, like-new 3-bedroom, 2-bath home in the charming Hull Island community of Oakland, just 0.5 miles from the West Orange Trail, 1.5 miles to Costco, and only 10 minutes from historic downtown Winter Garden. Recently updated and truly move-in ready, this split-plan residence shines with beautiful wood-look tile flooring throughout (no carpet anywhere!), fresh backyard turf just one year old, a brand-new dishwasher, and thoughtful upgrades in every room. Step inside to an inviting open layout where natural light abounds. The gourmet L-shaped kitchen is a chef’s dream, featuring abundant 42” maple cabinetry, quartz countertops, a tiled backsplash with sleek LED under-cabinet lighting, a gas range, a large center island with breakfast bar, an oversized walk-in pantry, and a built-in tech desk perfect for daily organization, charging devices, or remote work. Tucked at the rear for ultimate privacy, the serene primary suite offers a tray ceiling, expansive windows, and a spa-like ensuite bath with dual quartz vanities, an oversized shower showcasing upgraded subway tile and river rock flooring, semi-frameless glass enclosure, private water closet, and a huge walk-in closet. Two bright secondary bedrooms share a stylish hall bath at the front of the home. Relax or entertain on the covered lanai overlooking the fully fenced backyard with fresh turf and an extended paver patio. The custom backyard playhouse conveys, along with the washer, dryer, and security system. Additional upgrades include a tankless gas water heater, interior laundry room with utility sink, blinds on all windows, and all appliances included. Hull Island residents enjoy a resort-style pool with cabana, playground, bark park, scenic walking trails, and a peaceful dock on Lake Apopka, plus easy access to the Florida Turnpike. Impeccably maintained and turnkey in every way, schedule your private showing today and fall in love!
Courtesy: OAKSTRAND REALTY
888-912-5258
This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully curated for comfort, sophistication, and style. From the moment you arrive, the home commands attention with its architectural presence and grand entryway. Inside, soaring ceilings, designer finishes, and expansive living spaces create a refined yet inviting atmosphere. The heart of the home is the gourmet chef’s kitchen, seamlessly connected to the main living areas and perfect for both intimate gatherings and large-scale entertaining. A private office provides the ideal work-from-home environment, while multiple ensuite bedrooms ensure comfort and privacy for family and guests. The 4-car garage offers ample space for vehicles, storage, or a future car collection. Resort-style outdoor living takes center stage with a beautifully appointed summer kitchen, covered lanai, and a sparkling custom pool with spa, all overlooking the lush, manicured grounds of the corner lot. Whether hosting celebrations or enjoying quiet evenings at home, this outdoor oasis elevates everyday living. Nestled within one of Oakland’s most coveted luxury communities- Briley Farm, this home offers exclusivity, elegance, and convenience—just minutes from vibrant Winter Garden, top-rated schools, charming parks, and premier dining. A true masterpiece in Briley Farm, this residence delivers the ultimate blend of luxury and lifestyle.
Courtesy: PREMIER SOTHEBYS INT'L REALTY
407-581-7888
Come tour this stunning two-story Meritage Home thoughtfully designed for modern living and effortless entertaining! The open-concept floor plan features a spacious kitchen that seamlessly overlooks the living and dining areas, creating a setting for family gatherings or dinner parties. Upstairs, enjoy a versatile loft ideal for movie nights, game days or relaxing with friends. Go outside to your extended patio and unwind with morning coffee or evening wine, all while enjoying privacy of no rear neighbors. Upgrades abound, including a gourmet kitchen with granite countertops, stainless steel appliances and elegant luxury vinyl flooring, designed with comfort and efficiency in mind, this home includes a state-of-the-art fresh air system, spray foam insulation, and high-speed fiber optic internet for exceptional performance and connectivity. The fully fenced backyard and paver driveway offer style and convenience. Community amenities include a resort-style pool, dog parks, and playground, providing fun and relaxation for everyone. The neighborhood is just two minutes away to the West Orange Trail Head, offering easy access to outdoor recreation. It is also conveniently between Winter Garden and Clermont, you'll be just minutes from top-rated schools, shopping, dining and easy access to major highways. Fall in love. Make it yours.
Courtesy: WEMERT GROUP REALTY LLC
407-743-8356
Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE UPGRADES—creating a home that truly feels “better than new.” Step inside to an inviting OPEN-CONCEPT LAYOUT, where the chef’s kitchen overlooks the spacious living area. Recessed lighting, NEW TILE FLOORING on the main level (2023), and ceiling fans throughout (2020) elevate the home’s comfort and style. The entire home is also PREWIRED WITH CAT 6, ideal for high-speed connectivity. The DREAM KITCHEN is a showstopper with stylish cabinetry, stone countertops, a breakfast bar, built-in oven, cooktop stove with POT FILLER, tile backsplash, walk-in pantry, and a GALLEY-STYLE COFFEE BAR AREA—perfect for morning routines or entertaining. A spacious Kitchen dinette area overlooks the backyard, adding a warm and functional touch to the heart of the home. In the Living room, enjoy a CUSTOM ACCENT WALL (2023) and views of the large backyard through dual sliding glass doors. A separate Dining room offers flexibility for family gatherings or can easily serve as a formal living room. The first floor also includes a VERSATILE OFFICE/PLAYROOM, convenient under-stair storage, and ONE OF THE FIVE BEDROOMS—complete with laminate wood flooring—located next to a full bathroom, providing a perfect space for guests or multigenerational living. Upstairs, a GENEROUS LOFT creates a perfect secondary living area. The UPDATED PRIMARY SUITE (2025) features a beautiful tray ceiling, a LUXURIOUS EN SUITE BATH with dual vanities, a step-in shower, and a huge walk-in closet. Three additional bedrooms and another full bath offer plenty of comfortable space for family and guests. A paver driveway leads to the generous 3-CAR GARAGE featuring epoxy flooring, additional kitchen-style cabinetry, and PREWIRING for an electric vehicle. Outside, enjoy a large covered patio and an EXPANSIVE BACKYARD, ideal for future customization, gatherings, or play. Oakland Trails is loved for its peaceful setting and small-town charm, offering access to the West Orange Trail, playgrounds, green spaces, and TOP-RATED SCHOOLS. Ideally positioned near DOWNTOWN WINTER GARDEN, residents enjoy quaint dining and gatherings spots, PLANT STREET MARKET, charming shops, and easy access to SR 429 for seamless commuting. Every detail has been thoughtfully crafted for ELEVATED LIVING—come experience the exceptional quality and SOPHISTICATION this home offers. Schedule your showing today!
Courtesy: RE/MAX EXCLUSIVE COLLECTION
407-447-2829
Find out about the unique chance to be the owner of a 2,700 sqft home which sits on 2.55 private acres which we think is the ideal setting for space, privacy, and great growth. This 1983 built home has been very well preserved in it’s original condition which makes it the perfect choice for buyers who are after land, character and the freedom to update the home to suit their own style. In the home you’ll find a large open floor plan which has high vaulted ceilings and large picture windows that allow in lots of natural light. We have a fantastic floor to ceiling stone fire place which is a great spot for get together or a quiet night in. The kitchen is the heart of the home large with TONS of cabinetry, a large center island, built in appliances and it has plenty of space for friends and family to gather. It is a hard space to find today. A large enclosed summer room sunroom which extends your living area even more. In this space you may set up a game room, fitness area, home office, or use it for year round relaxation which includes the beauty of the back yard. The home has 4 large bedrooms and 2 full bathrooms which still present in the beautiful 1983 character they did back when, which we think is a great chance for a buyer that wants to update, modernize or keep the vintage look. Outside we have many options. With 2.55 acres which is plenty for gardens, animals, outdoor workshops, RV storage, or creating your own private retreat. Also included in the deal is a detached casita that is perfect for guests, extended family, an office, or has the chance to be used for a future rental income. The home has a private well and septic which means you have full independence and lower utility costs, ideal is who prefer rural living without giving up convenience.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floor plan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Heath Stone also features a 2-car detached garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Hearth Stone model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Pre-Construction. To be built. Introducing the Sunburst Model by Davila Homes Discover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floorplan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Sunburst also features a 3-car garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Upstairs, enjoy a stunning covered terrace, ideal for morning coffee, evening gatherings, or simply taking in the views of your surroundings. With its blend of functionality and sophistication, every space in the Sunburst is designed to make daily living both easy and elegant. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Sunburst model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.
Courtesy: REAL BROKER, LLC
855-450-0442
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintained, this home features 3 spacious bedrooms and 2 full bathrooms. The open and inviting floor plan offers a bright living room filled with natural light, a cozy family room ideal for relaxing, and a large dining area that’s perfect for hosting gatherings. The welcoming foyer greets you with a flexible space that can be used as a home office, reading nook, or a stylish sitting area. The kitchen boasts ample cabinet space, modern appliances, and a breakfast bar for casual dining. Additional highlights include: Central air conditioning and heating throughout the home Ceiling fans with lighting in each bedroom Freshly painted interiors with neutral tones Brand new Laminate wood-style flooring for easy maintenance Indoor laundry area for added convenience Fully fenced yard offering privacy and security Gated driveway with plenty of parking space Spacious backyard perfect for pets, play, or outdoor entertaining Whether you’re looking for your first home, a family retreat, or a peaceful escape close to everything, 507 W Oakland Avenue is the perfect choice. Don’t miss out on this rare gem — call today to schedule your private tour and experience the charm of Oakland living!
Courtesy: HOMEVEST REALTY
407-897-5400
One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue Charter School and minutes from Historic Downtown Winter Garden, where you can explore boutique shops, award-winning restaurants, and the scenic West Orange Trail. Inside, the thoughtfully designed layout features primary suites on both the first and second floors, offering flexible living arrangements perfect for multigenerational families or guests. The open floor plan and spacious living areas create a comfortable flow throughout, ideal for everyday living and entertaining alike. Step outside to your own backyard oasis, complete with a sparkling pool and spa surrounded by lush landscaping—perfect for relaxing weekends or hosting gatherings. Additional highlights include a brand-new roof installed in September 2025, offering long-term peace of mind and value. With its ideal location, privacy, and resort-style outdoor living, this home perfectly captures the essence of Florida living!
Courtesy: REAL BROKER, LLC
855-450-0442
Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a mother-in-law suite, perfect for multi-generational living or hosting extended guests. The primary bedroom provides a peaceful retreat with ample space and natural light throughout. New Roof 2022 & New AC 2025! Step outside to discover your personal oasis featuring a screened-in solar-heated pool area with a generous patio – ideal for year-round Florida living and entertaining. The premier lot offers breathtaking pond views, creating a serene backdrop for morning coffee or evening gatherings. This exclusive gated community provides residents with exceptional amenities including private lake access, a fishing pier for those peaceful weekend mornings, tennis courts for staying active, and a playground for family fun. The community perfectly balances privacy with recreation opportunities. Location couldn't be better – you're just minutes from charming downtown Winter Garden with its vibrant dining and shopping scene. All major parkways are easily accessible, making commuting a breeze. Theme Parks enthusiasts will appreciate being only 25 minutes from world-famous attractions like Disney and Universal Studios. Nearby conveniences include grocery shopping at the local market less than a mile away, and nature lovers will enjoy Oakland Nature Preserve just around the corner for hiking and wildlife viewing. This property combines luxury living with practical convenience in one of Florida's most desirable communities.
Courtesy: EXP REALTY LLC
888-883-8509
Welcome to your dream home in the highly sought-after Johns Landing community! This immaculate 4-bedroom, 3-bathroom residence offers a perfect blend of elegance, comfort, and convenience—nestled in the heart of charming Oakland, FL. From the moment you step inside, you’ll be greeted by soaring ceilings, abundant natural light, and an open-concept layout ideal for both entertaining and everyday living. This home has been meticulously maintained-- with fresh exterior paint, 2 nest thermostats, engineered hardwood flooring, electric water heater 2024, upgrades to bathrooms, new roof in 2021 and more! The chef’s kitchen boasts granite countertops, stainless steel appliances, and a spacious island, seamlessly flowing into the family room and dining area. The private owner’s suite features a spa-like bathroom with dual vanities, a soaking tub, and a walk-in shower. Step outside to your covered lanai and enjoy peaceful views of your beautifully landscaped yard—perfect for morning coffee or evening gatherings. Beyond the comfort of home, you’ll love the location! Just minutes from Walt Disney World Resort, Universal Orlando Resort, SeaWorld, and Orlando’s world-class dining, shopping, and entertainment and the famous Downtown Winter Garden area. Outdoor enthusiasts will appreciate easy access to the West Orange Trail for biking and walking, as well as nearby Lake Apopka for boating and fishing. With close proximity to major highways, commuting to Downtown Orlando or Orlando International Airport is a breeze. The neighborhood features 2 pickleball courts, tennis court and playground as we well as community boat ramp to John's Lake. Don’t miss this rare opportunity to own a slice of Florida paradise—schedule your private tour today!
Courtesy: CREEGAN GROUP
407-622-1111
Price reduced to $585,000 on this Stunning Home in Oakland Trails! This immaculate 3-bedroom, 2.5 bath home blends thoughtful upgrades with a warm, inviting layout. From the moment you walk in, pride of ownership is evident. The bright, open living area features built-in HEOS speakers, perfect for entertainment. The chef’s kitchen will impress with 42" wood cabinetry, granite countertops, under-cabinet and ambient above-cabinet lighting, stainless steel appliances, a massive island with sink, reverse osmosis water system, and an expansive dining area ideal for hosting. Step through the impressive 12-ft sliding glass doors, framed with custom drapery, onto a 640 sq. ft. screened patio. Overlooking wide open green space with no rear neighbors, this outdoor haven is perfect for relaxing, grilling, and gathering with friends and family. The spacious primary suite offers two walk-in closets and a luxurious 16x9 bathroom with a soaking tub and a separate shower. At the front of the home, two generous secondary bedrooms include one with Murphy-style bunk beds for space-saving versatility. The large laundry room features built-in cabinetry, a stainless steel utility sink, and extra closet storage. Even the garage is a standout, with three overhead 4x8 storage racks to keep everything organized. Residents of Oakland Trails enjoy a dog park, playground, and beautiful community pool. And direct access to the West Orange trail. Located minutes from downtown Winter Garden, with easy access to the 429, the 408, and the Florida Turnpike, this home delivers comfort, convenience, and style all in one.
Courtesy: BHHS FLORIDA REALTY
407-876-2090
Seller is offering First Mortgage Owner Financing up to $750,000 at 4.3% interest rate with a 3-year Balloon structure, to be organized by a real estate attorney. Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly. Set beneath a canopy of majestic, centuries-old oaks, this meticulously designed home offers a rare combination of elegance, comfort, and accessibility. With a spacious open floor plan, soaring 14-foot ceilings, and oversized 8-foot doors throughout, the home is both grand in scale and thoughtfully functional. Fully handicap accessible and designed with mobility in mind, it offers seamless, barrier-free living that accommodates all stages of life. At the heart of the home lies a gourmet kitchen, professionally designed by a chef and custom builder. This culinary centerpiece features top-of-the-line appliances, generous prep space, and luxury finishes—perfect for everything from everyday meals to large-scale entertaining. The open-concept design continues into expansive living and dining areas that flow effortlessly into the outdoors, creating an ideal environment for both intimate gatherings and lively celebrations. Step outside to your own private oasis: a beautifully screened-in pool, complemented by a fully equipped summer kitchen and ample patio space for lounging or dining under the stars. Whether you’re enjoying a quiet morning coffee poolside or hosting a weekend cookout, the outdoor living area is designed to elevate your lifestyle year-round. Located just steps from the Oakland Farmers Market, Charter School, Heritage Center, and Post Office, this home is at the center of a walkable, welcoming community where neighbors know one another and nature thrives. With direct golf cart access to vibrant Downtown Winter Garden, you’re only minutes from award-winning restaurants, unique shops, live entertainment, and a bustling weekly farmers market. Outdoor enthusiasts will love the nearby West Orange Trail and Lake Apopka’s scenic shoreline, perfect for biking, walking, birdwatching, or kayaking. And when adventure calls, you’re a short drive from some of the world’s most celebrated destinations, including Walt Disney World, Universal Studios, and Downtown Orlando. Combining small-town charm with big-city convenience, this location is truly second to none. More than just a residence, 101 N Starr Street is a destination for those seeking refined, accessible living in one of Central Florida’s most desirable communities. With its custom design, premium features, and unbeatable location, this home offers a lifestyle of beauty, comfort, and lasting value.
Courtesy: CENTRAL FLORIDA REALTY
321-234-1744
Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and maintained home is a turnkey away from being yours! 4 bed, 2.5 bath, the primary bed in the second level. The landscape perfectly accentuates your front porch. Step inside your fully upgraded home; complete with luxury upgrades ranging from lighting, designer finishes, and brand-name appliances. Up the stairs, you will find an upgraded railing and an accent wall leading you to four oversized bedrooms, two full bathrooms. The floor plan upstairs is split surrounding your flex/loft space allowing plenty of privacy and space for everyone. The primary suite has ample natural light and dimension with the tray ceilings along with the accent windows that beam light through them. The primary bathroom features quartz tile, two sinks, and a luxurious shower. The two extra bedrooms upstairs are generous in size and full of natural light. With an upstairs laundry room with ample storage. With a spacious community pool onsite, spring, summer, and fall days can be spent in the sun, just steps from your home. A beat away from the West Orange Trail, you can hop on your bike, or even jump on for a quick run. 10 minutes away from the desirable Downtown Winter Garden, and 15 minutes away from all major roadways, this home location truly gives you the best of Oakland, with the benefits of Winter Garden.
Courtesy: KELLER WILLIAMS ELITE PARTNERS III REALTY
321-527-5111
Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, built in 2020 and tucked away on a quiet cul-de-sac in the highly desirable town of Oakland. This home offers a beautifully designed open-concept main level with a spacious living area that flows seamlessly into the dining space and upgraded kitchen featuring quartz countertops, stainless steel appliances, a large pantry, and a functional layout ideal for everyday living or entertaining. Upstairs, the bonus room provides flexible space for an office, media room, or play area. The primary suite includes a walk-in closet and private bath with dual sinks, while two additional bedrooms and a full bath complete the second level. Additional highlights include energy-efficient construction, a two-car garage, an inside laundry room, a screened lanai, and a fully fenced backyard. Located minutes from Downtown Winter Garden and directly across from the Oakland Nature Preserve and the West Orange Trail, this home offers the rare blend of peaceful living and exceptional convenience. Enjoy access to miles of walking and biking trails, scenic boardwalks, parks, and year-round community activities. With nearby access to the Florida Turnpike, commuting to Orlando, the airport, or the theme parks is quick and easy. This move-in-ready Oakland home is the perfect combination of comfort, style, and location.
Courtesy: THE PROPERTY FIRM
407-530-5444
***SELLER SAYS SELL! BEST priced home in the community!*** Welcome to John’s Landing, a gated lakefront community in the charming town of Oakland, offering private lake access and a community dock on Johns Lake. Step inside this spacious 4-bedroom, 3-bathroom home with a 3-car garage and make it your own. The thoughtfully designed split floor plan includes a family room, formal living room, kitchen nook, and a formal dining area—perfect for both relaxed living and entertaining. The heart of the home is the kitchen, featuring stone countertops, 42-inch wood cabinetry, tiled backsplash, stainless steel appliances, and a pantry. A convenient kitchen bar opens to the living room, which boasts vaulted ceilings and luxury vinyl flooring, creating a spacious and cohesive feel. The primary suite is a true retreat, with vaulted ceilings, luxury vinyl flooring, sliding glass doors that open to the extended back patio, and a large en suite bathroom complete with a garden tub, walk-in shower, walk-in closet, and private water closet. Two bathrooms feature barrier-free tubs, offering enhanced accessibility and comfort. The three additional bedrooms are conveniently located together, with two sharing a Jack-and-Jill bathroom—ideal for families or guests. Outside, enjoy the extended patio, perfect for relaxing or entertaining. Residents of John’s Landing have access to exceptional community amenities, including private lake access, a boat ramp to Johns Lake, tennis courts, and a playground. Located just minutes from the West Orange Bike Trail that takes you to historic downtown Winter Garden, and major roadways including the Florida Turnpike, 429, and 408, this home offers both convenience and tranquility. You’ll love the close proximity to top-rated schools, shopping, and dining, all while enjoying the charm of suburban living. Homes in this community rarely last—don’t miss your chance to live in one of Oakland’s most desirable neighborhoods. Schedule your private tour today and get ready to make this home yours.
Courtesy: NEW HOMES REAL ESTATE, INC.
407-947-2475
Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours - YOUR WAY! The Oakland Park subdivision is a short walk on the West Orange Trail to downtown Winter Garden. Enjoy easy access to the community pool & clubhouse, dining, shopping & entertainment. This is luxury living at its best. Call us to discuss your options!
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.
