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$1,275,000
3 Beds 3 Baths Southern Oaks At Oakland Shores SubDv. 34760 Zip Code
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.

81 Millholland Street, Oakland

$479,900
3 Beds 3 Baths Oakland Trls Ph 2 SubDv. 34787 Zip Code
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!

2273 Standing Rock Circle, Oakland

$825,000
4 Beds 4 Baths Hull Island/Oakland Ph 2 SubDv. 34787 Zip Code
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!

1016 Catori Road, Oakland

$1,495,000
4 Beds 4 Baths Town/Oakland SubDv. 34760 Zip Code
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!

137 Petris Avenue, Oakland

$889,900
4 Beds 3 Baths Oakland Parkb-3 SubDv. 34787 Zip Code
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.

226 Hammock Preserve Loop, Oakland

$675,900
4 Beds 3 Baths Johns Landing SubDv. 34787 Zip Code
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!

239 Largovista Drive, Oakland

$850,000
4 Beds 4 Baths Oakland Parkb-3 SubDv. 34787 Zip Code
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.

166 Hammock Preserve Loop, Oakland

$364,500
3 Beds 3 Baths Longleaf/Oakland Rep SubDv. 34787 Zip Code
Welcome to 1511 Sweet Apple Street, 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!

1511 Sweet Apple Street, Oakland

$1,400,000
4 Beds 4 Baths Hull Island At Oakland SubDv. 34787 Zip Code
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.

1112 Hull Island Drive, Oakland

$415,000
3 Beds 2 Baths Oakland Town SubDv. 34760 Zip Code
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.

521 W Herriott Avenue, Oakland

$3,295,000
6 Beds 7 Baths Briley Farm SubDv. 34760 Zip Code
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.

312 Briley Avenue, Oakland

$540,000
4 Beds 3 Baths Johns Landing Ph 2 SubDv. 34787 Zip Code
Virtually Staged. Welcome to this spacious two-story home located in the highly desirable gated community of John's Landing in beautiful Oakland. Offering 4 bedrooms, 2.5 bathrooms, and over 2486 square feet of living space, this home combines generous room sizes, a functional layout, and an exceptional location to create the perfect place to call home. Step inside to discover multiple living and gathering spaces designed for everyday living as well as entertaining family and friends. The well-designed floor plan offers an inviting flow between the main living areas, while all four bedrooms are thoughtfully situated upstairs, creating a comfortable separation between living and private spaces. The expansive primary suite provides the perfect retreat at the end of the day, with plenty of room to relax and unwind. Outside, you'll appreciate the oversized backyard offering plenty of room for outdoor entertaining, play, gardening, or simply enjoying Florida's beautiful weather. With nearly a third of an acre, there is space that's increasingly difficult to find in today's market. Residents of John's Landing enjoy the security of a gated entrance along with outstanding community amenities including a lakefront dock, tennis courts, and playground. Ideally located just minutes from historic downtown Winter Garden, the West Orange Trail, the Florida Turnpike, shopping, dining, and everyday conveniences, this home offers the perfect combination of privacy, recreation, and accessibility. If you've been searching for a spacious home on a large homesite in one of West Orange County's most desirable communities, this is an opportunity you won't want to miss. Schedule your private showing today and experience everything this exceptional property has to offer!

223 Largovista Dr., Oakland

$2,615,320
6 Beds 7 Baths Grove/Oakland SubDv. 34787 Zip Code
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.

1152 Prado Lane, Oakland

$2,575,000
5 Beds 7 Baths Grove/Oakland SubDv. 34787 Zip Code
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.

1155 Prado Lane, Oakland

$679,900
4 Beds 4 Baths Hull Island/Oakland Ph 2 SubDv. 34787 Zip Code
Virtually Staged. Enjoy single-level living in lakefront Hull Island in this meticulously maintained 2,852 sq ft home built in 2022, with owned rooftop solar that keeps utility costs well below the Florida norm for a home this size. Four bedrooms, four full baths, and a two-car garage, all just minutes from historic Winter Garden's shops, restaurants, and Saturday farmers market. All four bedrooms, including the primary suite, plus the kitchen and all main living areas, are on the first floor. The only upstairs space is a private bonus suite with its own full bath, which functions equally well as a media room, flex room, or guest quarters well removed from the rest of the house. The foyer opens into a connected great room, dining area, and kitchen, with three sliding glass doors along the back wall looking out to a covered and screened lanai. Ceramic tile runs throughout the main living areas. The kitchen features the upgraded gas-range configuration with a Bosch refrigerator, GE stainless appliances, Silestone quartz counters, and an oversized island with seating. Finishes include 42-inch cabinets stacked to the 9'4" ceiling with crown molding. Inside: soft-close dovetail drawers, a three-tier pot and pan organizer, and a pull-out pantry. The owned rooftop solar system was installed in 2023 and carries a 25-year limited warranty through 2048. Combined with the tankless gas water heater, it helps keep monthly utility costs exceptionally low. The primary suite sits at the back of the first floor with a tray ceiling, dual raised-height vanities, a large walk-in shower with a built-in recessed shelf, and a walk-in closet with custom shelving that passes directly through to the laundry room. The upstairs bonus suite measures 18'8" x 25'6" and has its own full bath. It is pre-wired as a dedicated media space, with structured Cat6 throughout, a ceiling-mounted projector outlet, and TV and data chases ready for a wall-mounted display. Additional features include a two-car garage with a 220V/30A outlet suitable for Level 2 EV charging, a workshop, or additional appliances; a Ring doorbell, alarm system, and cameras that convey with the home; upgraded satin nickel interior door hardware with a coordinated front door handleset; upgraded light fixtures; and front gutters. Hull Island amenities include a community pool, clubhouse, playground, and community fishing pier, with the West Orange Trail at the community's doorstep.

2017 Boss Hewett Street, Oakland

$1,049,000
4 Beds 3 Baths Oakland Town SubDv. 34760 Zip Code
Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

250 N Walker Street, Oakland

$515,000
4 Beds 3 Baths Oakland Trls Ph 1 SubDv. 34787 Zip Code
INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by newer(2024) luxury plank flooring, a large living/dining area, built-in OFFICE SPACE, and a half sized bathroom. The kitchen is a CHEF'S DREAM featuring granite counters, a large eat-in island, stainless steel appliances, built-in oven and microwave, designer pendant lighting, closet style pantry, and a dedicated coffee/work station. WOW! Head upstairs and pass through the BONUS LOFT area into an OVERSIZED MASTER SUITE with tray ceilings, a large split vanity master bath, and a MASSIVE WALK-IN CLOSET equipped with built-in shelving and organizers. The second floor also contains three secondary bedrooms, a full size hallway bathroom, and a large laundry room. Additional features of the home include: a FULL SOLAR PANEL SYSTEM(providing significant energy savings), an oversized two car garage, built-in security system, and paver driveway. The Oakland Trails community includes a community pool and clubhouse, dog park, playground, and walking trails. Located minutes away from the WEST ORANGE TRAIL this area is a hotbed for outdoor recreation and is ZONED FOR EXCELLENT SCHOOLS! In close proximity to major commuting highways, downtown Winter Garden, and ample shopping amenities, this is a PRIME LOCATION home and MOVE-IN ready for it's next owners. DON'T DELAY!! Book your private showing today.

2259 White Feather Loop, Oakland

$796,000
5 Beds 3 Baths Oakland Trls Ph 2 SubDv. 34787 Zip Code
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!

1970 Standing Rock Circle, Oakland

$2,310,600
5 Beds 6 Baths Grove At The Harvest District SubDv. 34787 Zip Code
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.

1146 Prado Lane, Oakland

$2,380,160
5 Beds 6 Baths Grove At The Harvest District SubDv. 34787 Zip Code
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.

1173 Prado Lane, Oakland

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Oakland FL Homes for Sale

There are 30 homes for sale in Oakland, Florida as of 2026-09-17, at a median list price of $869,950 and a median of 66 days on market. Every active Oakland listing is above, newest first. What follows is what those listings add up to.

Oakland market at a glance

Active listings30
Median list price$869,950
Median price per square foot$299
Median size3,545 square feet
Median year built2019
Median days on market66
On market 60+ days16 (53.33%)
Priced below original asking11 (36.67%)

Source: Stellar MLS via the Bridge RESO feed, pulled 2026-09-17. Updated weekly.

What the numbers say for Oakland buyers

11 of the 30 Oakland homes on the market (37%) are asking less than they did on day one, and 16 (53%) have been listed 60 days or longer. Those two figures are the practical case for making an offer here. A seller 66 days in who has already cut once is a different negotiation than one of the 14 listings still inside its first 60 days.

Across the 11 Oakland listings that have already come down, the typical reduction is 7.27% off the original asking price. That is the size of a first concession, not a final one.

Oakland homes by price range

Under $250,00000.0%
$250,000 to $400,00013.3%
$400,000 to $600,000620.0%
$600,000 and up2376.7%

Property types in Oakland

Single Family Residence29
Townhouse1

Neighborhoods and subdivisions in Oakland

Every Oakland subdivision with an active listing or its own page here, ranked by inventory. A subdivision showing 0 still appears: this is a live MLS feed and inventory changes daily. The 30 homes in named subdivisions are 100% of the Oakland market; the rest are on unplatted land or were listed without a subdivision name.

Oakland Trls5 active$515,000
Oakland Town3 active$619,000*
Johns Landing3 active$675,900*
Grove At The Harvest District3 active$2,310,600*
Grove/Oakland3 active$2,575,000*
Oakland Parkb-32 active$869,950*
Hull Island/Oakland2 active$752,450*
Briley Farm1 active$3,295,000*
Oakland1 active$1,250,000*
Oakland Pointe1 active$799,999*
Town/Oakland1 active$1,495,000*
Oakland Park1 active$2,098,000*
Johns Cove 43/1041 active$2,550,000*
Hull Island At Oakland1 active$1,400,000*
Longleaf/Oakland Rep1 active$364,500*
Johns Cove1 active$795,000*

Subdivision names come from the MLS as agents entered them. Active count and median list price as of 2026-09-17. * Medians on rows with fewer than 4 listings are indicative only. Open a subdivision for days on market, price per square foot and sales history.

About Oakland

Oakland is a town of 3,516 at the 2020 census, up 38.5 percent from 2,538 in 2010, on 2.10 square miles.

Its post office opened in 1860, closed in 1867 and reopened in 1877. During the Civil War it was the only post office operating inside what is now Orange County, because the Orlando office was closed from 1861 to 1866.

In the boom of the 1880s Oakland was the commercial center of west Orange County and incorporated in 1887. Then a fire in the business district, a run of freezes through the 1890s and the growth of neighbouring Winter Garden left it a village instead of a town.

Oakland zip codes

34787 (23 listings), 34760 (7 listings)

Oakland homes by property type

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Frequently asked questions

How many homes are for sale in Oakland, FL?

There were 30 active residential listings in Oakland as of 2026-09-17, at a median list price of $869,950. That count comes from the Stellar MLS feed and is refreshed weekly.

What is the median home price in Oakland, FL?

The median list price in Oakland was $869,950 as of 2026-09-17, or about $299 per square foot. The median home on the market is 3,545 square feet and was built in 2019.

How long do homes take to sell in Oakland?

Median days on market was 66 as of 2026-09-17. 16 of the 30 listings, 53% of the Oakland market, have been listed 60 days or longer, and that is where most of the negotiating room sits.

Are Oakland sellers reducing their prices?

11 Oakland listings, 36.67% of the market, are now asking less than they did originally, at a median reduction of 7.27%. That is the size of a typical first concession here, and it is usually not the last one.

What neighborhoods are in Oakland, FL?

16 named subdivisions had at least one active listing in Oakland as of 2026-09-17, and every one is listed above with its own median price and days on market. Oakland Trls led with 5 active listings at a median of $515,000.

What zip codes cover Oakland, FL?

Oakland listings sat in 2 zip codes as of 2026-09-17: 34787 with 23 active listings, 34760 with 7 active listings.

The Homes In Orlando Team at NextHome Neighborhood Realty covers Orange, Seminole, Lake and Volusia counties. Call or text 407-616-9019 to see any Oakland listing on this page.