Courtesy: COMPASS FLORIDA LLC
407-203-9441
Some homes simply sit in a neighborhood. This one feels like it belongs there. Welcome to 150 Hammock Preserve Loop, a 2023 Rockwell Homes residence tucked into the heart of Oakland Park, where the front porch looks out toward mature oak trees and the best parts of the Winter Garden lifestyle are never far from home. Step inside and you’re immediately greeted by a dedicated office to the left of the entry, creating the perfect work-from-home space while keeping it separate from the main living areas. Throughout the home, thoughtful custom updates give each space a personality of its own. The primary suite is conveniently located on the main floor, while the additional bedrooms and spacious loft are upstairs, creating a layout that offers both separation and flexibility. A rare three-car garage provides the extra space that can be difficult to find in Oakland Park, whether you need room for vehicles, golf carts, bikes, storage, or all of the above. Out back, the generous yard offers plenty of room to create your own outdoor retreat, including space for a future pool. But what makes this home especially difficult to replicate is everything beyond the front door. Oakland Park is one of Winter Garden’s most sought-after communities for a reason. Tree-lined streets, front porches, parks, playgrounds, two resort-style community pools, a clubhouse, dog park, waterfront spaces, and miles of trails create a neighborhood designed to actually be enjoyed. Hop on your bike and connect to the West Orange Trail, or grab the golf cart and head toward Downtown Winter Garden for a morning at the Farmers Market, drinks at Crooked Can, dinner along Plant Street, boutique shopping, community events, and everything surrounding Plant Street Market. Here, weekends can start with coffee on the front porch beneath the oaks, turn into an afternoon by the pool or on the trail, and end with a golf cart ride into Downtown Winter Garden. Built in 2023, filled with custom touches, complete with a dedicated office, rare three-car garage, and a backyard ready for what comes next, 150 Hammock Preserve Loop offers more than a beautiful home. It offers the Oakland Park lifestyle that makes this neighborhood so special.
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: 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: 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: THE REAL ESTATE COLLECTION LLC
407-656-7814
A rare opportunity to own a beautifully maintained home in the heart of Oakland, offered at an exceptional value under $500,000. Located in the sought-after Longleaf at Oakland community, this 3-bedroom, 2.5-bath home offers a thoughtful layout, beautiful outdoor space, and a prime location—all at a price point that is increasingly hard to find in this desirable area. Set on a quiet cul-de-sac, the home welcomes you with a modern and functional layout designed for both everyday living and entertaining. Inside, luxury vinyl plank flooring, recessed lighting throughout, and a bright, comfortable feel create a welcoming atmosphere. The kitchen features granite countertops and custom shelving, while additional custom shelving in the laundry room adds both style and practical storage. Spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room provide flexibility for everyday living. A water softener system adds another thoughtful touch to the home. Step outside to a fully fenced backyard offering privacy and flexibility for pets, play, gardening, or simply enjoying your own outdoor space. The peaceful setting and cul-de-sac location create an inviting sense of privacy while still keeping you close to everything Oakland and Winter Garden have to offer. The location is hard to beat. Take a quick walk to the West Orange Trail or enjoy easy access to the Oakland Nature Preserve. Downtown Winter Garden's shops, restaurants, farmers market, and charming atmosphere are just minutes away, while the Florida Turnpike provides convenient access throughout Central Florida. Orlando's world-class theme parks are approximately 20 minutes away. Beautifully cared for, ideally located, and thoughtfully priced, 1184 Bobcat Chase Blvd offers an exceptional opportunity to enjoy the best of Oakland living with comfort, convenience, and a price point that makes this home stand out.
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: 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: REAL BROKER, LLC
855-450-0442
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. 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: REGENCY REAL ESTATE LLC
407-469-5021
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: 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: 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: OLYMPUS EXECUTIVE REALTY INC
407-469-0090
Under contract-accepting backup offers. A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor bedroom and full bath ideal for guests, extended family, or an in-law arrangement**, plus the exceptional Winter Garden lifestyle buyers are looking for. Tall ceilings, 8-foot doors, elegant architectural details, high-end décor, and thoughtfully designed living spaces create an elevated yet comfortable feel throughout. (If the buyer prefers not to keep the furniture and furnishings, they can be excluded from the sale.) The showpiece kitchen is truly the heart of the home, featuring premium quartz countertops, a 5-burner gas range, stainless steel hood, striking designer backsplash, and spacious walk-in pantry. The spa-inspired primary suite offers an expansive private bathroom and generous walk-in closet, creating the perfect retreat. And for a little extra personality, the home even has its very own “Harry Potter” closet! Enjoy Florida living from the inviting screened front porch, complete with a porch swing perfect for morning coffee, an afternoon book, or relaxing at the end of the day. The back patio and fenced yard provide another comfortable setting for entertaining, outdoor dining, or simply enjoying the beautiful Florida weather. An expansive 3-car garage offers exceptional space and storage. Offered fully furnished with beautiful, high-end furnishings and décor, this home is truly turnkey—just bring your suitcase and start enjoying the lifestyle. Located near highly regarded schools and just moments from the West Orange Trail, walk, bike, take your golf cart, or drive to charming Downtown Winter Garden, the Farmers Market, restaurants, shopping, and entertainment. Move in before the holidays and experience everything this incredible community has to offer, including festive neighborhood traditions and upcoming celebrations such as the golf cart parade, fall festival, and more. An exceptional opportunity to own a remarkably equipped home in one of the area’s most desirable communities at an amazing value.
Courtesy: THE PROPERTY FIRM
407-530-5444
Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Longleaf at Oakland community! From the moment you arrive, you will appreciate the inviting feel, thoughtful layout, and pride of ownership throughout. Inside, enjoy spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room designed for everyday living and entertaining. Step outside to a wonderful backyard and porch area, with both the family room and porch pre-wired for speakers—perfect for creating an effortless indoor-outdoor entertaining experience. The two-car garage even features an electric vehicle charging outlet. The location is hard to beat— take a quick 5-minute walk to the West Orange Trail, enjoy the shops, dining, and charm of Downtown Winter Garden just 10 minutes away, and reach the Florida Turnpike in minutes. Beautifully cared for, ideally located, and truly move-in ready—this is the Oakland home you’ve been waiting for!
Courtesy: SOUTHERN PRESTIGE REALTY INC
407-614-3873
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.
Courtesy: OFFERPAD BROKERAGE FL LLC
813-534-6326
Hot Oakland opportunity. Motivated seller, bring all offers. This two-bed, one-bath on a no HOA lot puts you minutes to John’s Lake boat access and the West Orange Trail, plus a short hop to downtown Winter Garden dining and shops. Fix and flip, hold as a rental, or tear down and build new. The upside is real and the seller is ready. Quiet small-town setting with outdoor perks and growth around you. Don’t wait. Opportunities at this price and location move fast.
Courtesy: HOMEVEST REALTY
407-897-5400
Welcome to this extraordinary custom lakefront estate offering breathtaking views of Lake Apopka and the ultimate Florida waterfront lifestyle. Designed with luxury and functionality in mind, this one-of-a-kind home showcases premium upgrades, exceptional craftsmanship, and direct lake access. The heart of the home is a chef-inspired kitchen featuring a natural gas cooktop, double ovens, expansive center island, abundant counter space, separate breakfast dinette, and a custom walk-in pantry with floor-to-ceiling shelving. The kitchen opens seamlessly to the spacious family room with soaring 12-foot ceilings and triple sliding glass doors that frame spectacular lake views and fill the home with natural light. Step outside to your private waterfront oasis where a covered, screened lanai overlooks professionally landscaped grounds and unforgettable sunsets. The impressive 20' x 60' brick paver patio leads to a private dock with an electric covered boat lift, providing direct access to Lake Apopka. Enjoy fishing from your dock, boating the scenic Harris Chain of Lakes via the Apopka-Beauclair Canal, or spending the day exploring the waterfront restaurants, shops, and attractions of historic downtown Mount Dora and Tavares. The thoughtfully designed floor plan includes a formal dining room with soaring ceilings and a private office with double doors, ideal for working from home. The luxurious primary suite is a true retreat with panoramic lake views, spa-inspired bath featuring a frameless floor-to-ceiling tiled double shower with dual shower heads and built-in bench, soaking tub, dual vanities, and custom walk-in closets. A hidden Murphy door provides private access to two secondary bedrooms and a full bath, creating the perfect guest or family wing. The oversized fourth bedroom offers an ensuite bath and walk-in closet, ideal for guests or multigenerational living. Additional premium features include a 24kW natural gas whole-house generator, electric vehicle charging station, water softener, security system, surround sound, insulated garage doors and ceiling, garage utility sink, overhead storage, and a spacious laundry room with built-in cabinetry, extensive counter space, and utility sink. The oversized three-car garage and expansive six-car brick paver driveway provide ample parking and storage. Located in the sought-after gated community of Hull Island, residents enjoy resort-style amenities including a community pool, gazebo, playground, bark park, and exclusive private access to the 150-acre Oakland Nature Preserve with miles of scenic trails. Nestled in the charming Town of Oakland, this exceptional home is just minutes from Winter Garden Village, historic Downtown Winter Garden, the award-winning Winter Garden Farmers Market, the West Orange Trail, Downtown Clermont, shopping, dining, major hospitals, Orlando's world-famous attractions, Orlando International Airport, and major highways. Florida's beautiful east and west coast beaches are approximately one hour away.
Courtesy: REAL BROKER, LLC
855-450-0442
Under contract-accepting backup offers. PRICE REDUCED - Accepting Offers! The home has recently been entirely staged on the inside of the property - come tour this BEAUTY! NOTE: to add extra storage, a (large shed) can be added onto the property within the purchase of the home. NO HOA! Welcome to this brand-new construction home in the heart of Oakland! This thoughtfully designed 3-bedroom, 2-bathroom residence offers 1,170 square feet of modern living space on a 0.09-acre homesite. The open-concept floor plan features luxury vinyl plank flooring throughout the main living areas and bedrooms, with porcelain tile flooring in both bathrooms for added durability and style. The kitchen is equipped with quartz countertops, modern cabinetry, stainless steel appliances, and a functional layout that flows seamlessly into the living and dining areas, making it ideal for everyday living and entertaining. Contemporary lighting, designer fixtures, and quality finishes can be found throughout the home. The primary suite includes a walk-in closet and an ensuite bathroom with a quartz vanity and a porcelain tile shower. Two additional bedrooms provide flexibility for family, guests, or a home office. Additional features include an indoor laundry area, energy-efficient windows, modern exterior finishes, and a paver driveway. Conveniently located near downtown Winter Garden, the West Orange Trail, shopping, dining, parks, major highways, and local attractions, this move-in-ready home offers the opportunity to enjoy low-maintenance living in the desirable Town of Oakland. Don't miss your chance to own this newly built home in one of Central Florida's most sought-after communities.
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thoughtfully designed living space on a private 0.5-acre homesite. Featuring 6 bedrooms, 6 full bathrooms, and 1 half bath, this home showcases one of Element's most sought-after floor plans, blending timeless architecture with modern luxury. Designed for both everyday living and elegant entertaining, the open-concept layout features a gourmet chef's kitchen, expansive great room, private office, loft, and spacious covered lanai. Enjoy true Florida living with an extended outdoor entertaining area complete with a resort-style pool, spa, and fully equipped summer kitchen for seamless indoor-outdoor living. Every detail reflects the exceptional craftsmanship, premium finishes, and attention to detail that define Element Home Builders. With construction just beginning, buyers have the rare opportunity to personalize select finishes and own a brand-new custom luxury home in one of Oakland's most desirable communities. Briley Farm is an exclusive enclave just minutes from historic Downtown Winter Garden, the West Orange Trail, top-rated schools, boutique shopping, dining, and major highways, offering convenient access to Downtown Orlando, Walt Disney World, and Orlando International Airport. Experience the perfect blend of luxury, privacy, and convenience in one of Central Florida's premier custom home communities.ning, and major roadways, while maintaining the privacy and charm of luxury estate living. Renderings are for illustration purposes only. Features, specifications, and finishes are subject to change without notice.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers an extraordinary standard of luxury estate living. Every detail speaks to a level of craftsmanship and thoughtfulness that simply cannot be replicated. Five generously sized bedrooms, each with its own private ensuite bath, provides unmatched comfort and privacy for family and guests alike. Two additional powder baths serve the main living areas, while a dedicated pool bath keeps the outdoor experience seamless. At the heart of the home, a dramatic double island kitchen commands attention — equal parts showpiece and hardworking hub — crowned by soaring coffered ceilings that lend architectural depth and timeless elegance throughout. Step outside to your own private resort, where a sparkling pool and spa, summer kitchen, and covered lanai with roll-down screens create the ultimate Florida lifestyle — open-air breezes or a fully enclosed retreat, all at the touch of a button. Beyond your front door, The Grove places you steps from The Harvest District's boutique shops and restaurants, with exclusive access to the resort amenities at nearby Briley Farm — all reachable by foot or golf cart.
Courtesy: REGENCY REAL ESTATE LLC
321-303-4539
Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the exclusive, boutique enclave of The Grove at the Harvest District in the charming Town of Oakland, Florida. Spanning an impressive 4,658 square feet, this stunning residence offers six generously sized bedrooms, each with its own private ensuite bath, delivering the ultimate in comfort and privacy for family and guests alike. A dedicated home office provides the perfect retreat for focused work, while the airy upper-level loft adds flexible living space ideal for a media room, playroom, or secondary lounge. Step outside and experience true Florida luxury a custom pool serves as the centerpiece of the outdoor living area, perfectly positioned to capture serene pond views that make every morning and evening feel like a private escape. Seamless indoor-outdoor integration defines this home's design philosophy, with expansive windows flooding the interior with natural light and blurring the line between inside and out. Inside, Davila Homes' signature craftsmanship is evident at every turn: timeless architecture, high-end finishes, an open-concept layout designed for effortless entertaining, and a gourmet kitchen appointed with state-of-the-art appliances. Every detail was thoughtfully curated and personalized through Davila's exclusive Design Center experience. The Grove is one of Oakland's most intimate and sought-after communities, featuring just 44 homesites surrounded by lush common areas, water features, walking trails, and bike paths. Minutes from the vibrant shops and dining of Downtown Winter Garden, top-rated West Orange County schools, and the beloved West Orange Trail, yet tucked away in the quiet charm of one of Central Florida's most historic small towns.
Courtesy: RE/MAX TOWN & COUNTRY REALTY
407-695-2066
Exceptional 6-bedroom, 4-bathroom home on a private cul-de-sac in the highly desirable gated community of Johns Cove. This spacious residence features formal living and dining rooms, a large family room, soaring vaulted ceilings, and a double staircase. The kitchen offers stainless steel appliances, granite countertops, a large island, abundant cabinetry, and a breakfast area with tranquil pond views. The first-floor primary suite overlooks the pool and includes an en-suite bath with dual vanities, garden tub, separate shower, and walk-in closet. Upstairs offers generously sized bedrooms and a dedicated movie room. Enjoy a screened heated saltwater pool and spa, updated full pool bath, covered lanai, private balcony, and no rear neighbors. Residents enjoy a private boat ramp on Johns Lake, ideal for bass fishing, boating, paddle boarding, and kayaking. Near West Orange Trail, Downtown Winter Garden, Winter Garden Village, dining, shopping, and top-rated schools.
Courtesy: REGENCY REAL ESTATE LLC
321-303-4539
Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charming Oakland, Florida. Masterfully built by the renowned Justice & Wood Builders — whose principals each bring over 25 years of custom homebuilding experience — this stunning residence delivers the perfect blend of timeless craftsmanship, thoughtful design, and elevated luxury living. Spanning 4,210 square feet of livable space (5,914 total sq ft) across a thoughtfully designed floor plan, The Wildflower offers 5 bedrooms, 5 full baths, and 2 half baths, providing ample room for families who prioritize space and style. From the moment you arrive, every detail speaks to the quality and care poured into this home. Inside, a versatile loft and flex room provides endless possibilities — a home office, media room, playroom, or private retreat. The open, flowing layout is designed for both everyday living and effortless entertaining. Step outside to your own private resort. A custom pool and spa take center stage in the backyard oasis, a covered rear lanai with roll down screens, a fireplace complemented by a summer kitchen and cabana — perfect for hosting under the Florida sun. Enjoy evenings at home with a built in fire pit and beautiful landscape lighting. A 3-car garage rounds out the thoughtful features that make this home as functional as it is beautiful. Located just minutes from downtown Winter Garden's vibrant dining and shopping scene, top-rated schools, and easy access to the Florida Turnpike, The Grove offers the rare combination of peaceful small-town living with big-city convenience. Estimated completion Spring 2027. Secure your lot today and experience the Justice & Wood difference — where every home is built with excellence, without cutting corners.
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Welcome to Oakland Trails, one of Oakland’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and location. Built in 2018, the home features a bright, open-concept floor plan with spacious living areas, a modern kitchen, and plenty of room for both everyday living and entertaining. Step outside and enjoy all the amenities that make Oakland Trails so special, including a resort-style community pool and playground. Outdoor enthusiasts will love being just minutes from the renowned West Orange Trail, offering miles of scenic paths for walking, running, and biking through some of Central Florida’s most beautiful landscapes. Conveniently located near historic downtown Winter Garden, shopping, dining, and major roadways, this home combines small-town charm with everyday convenience. Whether you're relaxing at the pool, exploring the nearby trail system, or enjoying all that the area has to offer, this property delivers the Florida lifestyle you've been looking for.
Courtesy: JACK KELLER INC
727-586-1497
Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.
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.
