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Oakland FL Single Family Homes for Sale

2561 Sky Stone Court, Oakland

2561 Sky Stone Court, Oakland

4 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 1 SubDv. ⋅ 34787 Zip Code

Virtually Staged. This beautiful 4-bedroom, 2.5-bath home in the charming town of Oakland! Ideally located with no rear neighbors, this home offers comfort, privacy, and everyday convenience.Recent updates include new flooring and fresh interior paint in 2025, plus freshly painted exterior in 2026. Enjoy carpet-free living throughout and a tile roof that adds to the home’s curb appeal. Located in a community with excellent amenities, low HOA and NO CDD. this home offers easy access to major highways, making trips to Disney and other Central Florida attractions a breeze. The newly opened Costco is just outside the community, with shopping and everyday essentials close at hand. A wonderful opportunity to enjoy small-town charm in a convenient location!

2561 Sky Stone Court, Oakland

150 Hammock Preserve Loop, Oakland

150 Hammock Preserve Loop, Oakland

4 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code

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.

150 Hammock Preserve Loop, Oakland

100 Mather Smith Drive, Oakland

100 Mather Smith Drive, Oakland

3 Beds ⋅ 2 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code

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.

100 Mather Smith Drive, Oakland

2107 Bay Line Road, Oakland

2107 Bay Line Road, Oakland

3 Beds ⋅ 2 Baths ⋅ Hull Island/Oakland SubDv. ⋅ 34787 Zip Code

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%!!!

2107 Bay Line Road, Oakland

2696 Bobcat Chase Boulevard, Oakland

2696 Bobcat Chase Boulevard, Oakland

3 Beds ⋅ 3 Baths ⋅ Longleaf/Oakland Rep SubDv. ⋅ 34787 Zip Code

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!

2696 Bobcat Chase Boulevard, Oakland

2470 Standing Rock Circle, Oakland

2470 Standing Rock Circle, Oakland

5 Beds ⋅ 3 Baths ⋅ Oakland Trails SubDv. ⋅ 34787 Zip Code

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.

2470 Standing Rock Circle, Oakland

81 Millholland Street, Oakland

81 Millholland Street, Oakland

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

2273 Standing Rock Circle, Oakland

2273 Standing Rock Circle, Oakland

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. Equipped with FULLY PAID-OFF TESLA SOLAR PANELS, this home offers massive utility savings with no additional lease or loan payments—pure modern efficiency from day one! With major shopping, dining, and entertainment options located within 15 minutes of this community, you have no shortage of lifestyle at your fingertips! You can get to Disney parks in about 20-25 minutes! You're also zoned to A rated schools, and have a very popular charter school - Oakland Avenue Charter School just minutes away. Come tour this home today!

2273 Standing Rock Circle, Oakland

1016 Catori Road, Oakland

1016 Catori Road, Oakland

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

137 Petris Avenue, Oakland

137 Petris Avenue, Oakland

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

239 Largovista Drive, Oakland

239 Largovista Drive, Oakland

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

2471 Sky Stone Court, Oakland

2471 Sky Stone Court, Oakland

4 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 1 SubDv. ⋅ 34787 Zip Code

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.

2471 Sky Stone Court, Oakland

320 W Sadler Avenue, Oakland

320 W Sadler Avenue, Oakland

2 Beds ⋅ 1 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

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.

320 W Sadler Avenue, Oakland

1112 Hull Island Drive, Oakland

1112 Hull Island Drive, Oakland

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

312 Briley Avenue, Oakland

312 Briley Avenue, Oakland

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

223 Largovista Dr., Oakland

223 Largovista Dr., Oakland

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

1603 Johns Cove Ln, Oakland

1603 Johns Cove Ln, Oakland

6 Beds ⋅ 4 Baths ⋅ Johns Cove SubDv. ⋅ 34787 Zip Code

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.

1603 Johns Cove Ln, Oakland

1134 Prado Lane, Oakland

1134 Prado Lane, Oakland

5 Beds ⋅ 8 Baths ⋅ Grove/Oakland SubDv. ⋅ 34787 Zip Code

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.

1134 Prado Lane, Oakland

1152 Prado Lane, Oakland

1152 Prado Lane, Oakland

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

1155 Prado Lane, Oakland

1155 Prado Lane, Oakland

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

2241 White Feather Loop, Oakland

2241 White Feather Loop, Oakland

3 Beds ⋅ 3 Baths ⋅ Oakland Trls Ph 1 SubDv. ⋅ 34787 Zip Code

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.

2241 White Feather Loop, Oakland

16 Oakland Pointe Circle, Oakland

16 Oakland Pointe Circle, Oakland

5 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code

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.

16 Oakland Pointe Circle, Oakland

2017 Boss Hewett Street, Oakland

2017 Boss Hewett Street, Oakland

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

219 Largovista Drive, Oakland

219 Largovista Drive, Oakland

5 Beds ⋅ 4 Baths ⋅ Johns Landing SubDv. ⋅ 34787 Zip Code

Beautiful house, fully remodeled luxury residence in the exclusive gated community of John's Landing. Offering nearly 4,000 sq/ft, this impressive 5 bedrooms, 4 bath home features, 2 of the bedrooms is a suite, high-end finishes, and a seamless modern design throughout. Porcelain tile flooring, a stunning gourmet kitchen with island with quartz countertops, custom cabinetry and a premium stainless steel appliances. Every details has been thoughtfully upgraded; spa inspired master bathroom include designer walk-in shower,LED mirrors, and luxury fixtures. Step outside to a private screened-in pool and spa, creating the perfect setting for entertaining and relaxed living. Residents enjoy gated access and private boat/jet sky ramp to John's Lake, ideal for boating and jet skis. Also prime location access to Turnpike Hwy and just minutes from Winter Garden, Clermont, Downtown Orlando and all Disney Parks.

219 Largovista Drive, Oakland

250 N Walker Street, Oakland

250 N Walker Street, Oakland

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

812 Johns Point Drive, Oakland

812 Johns Point Drive, Oakland

5 Beds ⋅ 6 Baths ⋅ Johns Cove 43/104 SubDv. ⋅ 34787 Zip Code

Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout. Designed for effortless entertaining, the open-concept layout showcases a chef’s kitchen with a waterfall quartz island, custom cabinetry, premium stainless steel appliances, and a full-slab backsplash, all flowing into an expansive living area with designer lighting and seamless indoor-outdoor access. The primary suite offers a private retreat with abundant natural light, custom closets, and a spa-inspired bath featuring a freestanding soaking tub and luxury walk-in shower. Step outside to a screened pool, upgraded travertine deck, and private pier, creating an unparalleled waterfront lifestyle ideal for relaxation and entertaining. Additional highlights include a concrete tile roof (maintained), smart home features, updated HVAC, epoxy garage, modern laundry room, and high-end upgrades throughout. Ideally located minutes from Downtown Winter Garden, premier dining, shopping, and top-rated schools, this is a rare opportunity to own an unparalleled lakefront property.

812 Johns Point Drive, Oakland

1106 Sarah Mathews Drive, Oakland

1106 Sarah Mathews Drive, Oakland

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34787 Zip Code

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1106 Sarah Mathews Drive, Oakland

1970 Standing Rock Circle, Oakland

1970 Standing Rock Circle, Oakland

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

1146 Prado Lane, Oakland

1146 Prado Lane, Oakland

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

1173 Prado Lane, Oakland

1173 Prado Lane, Oakland

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 Single Family Homes for Sale

There are 30 single family homes for sale in Oakland, Florida as of 2026-10-04, at a median list price of $810,500 and a median of 73 days on market. Detached homes, which make up most of what is for sale here.

Oakland single family homes for sale at a glance

Active single family homes	30
Share of the Oakland market	96.8% of 31 listings
Median list price	$810,500
Median price per square foot	$305
Median size	3,479 square feet
Median year built	2019
Median days on market	73
On market 60+ days	16 (53.33%)

Source: Stellar MLS via the Bridge RESO feed, pulled 2026-10-04. Updated weekly.

How Oakland single family homes compare to the rest of the city

The median single family home in Oakland asks $810,500 against $796,000 for the city as a whole, and $305 per square foot against $284. Single Family Homes make up 96.8% of everything on the market here.

9 of them, 30.0%, are asking less than they did originally, at a median reduction of 3.85%. That is the size of a first concession, not a final one.

Oakland single family homes by price range

Under $250,000	1	3.3%
$250,000 to $400,000	0	0.0%
$400,000 to $600,000	6	20.0%
$600,000 and up	23	76.7%

Oakland single family homes by bedroom count

2 bedrooms	1
3 bedrooms	6
4 bedrooms	10
5 bedrooms+	13

Other Oakland searches

All Oakland Homes for Sale

Zip codes

34787 (23), 34760 (7)

Frequently asked questions

How many single family homes are for sale in Oakland, FL?

There were 30 active single family homes listed in Oakland as of 2026-10-04, 96.8% of the 31 residential listings in the city. That count comes from the Stellar MLS feed and is refreshed weekly.

What is the median price of a single family home in Oakland, FL?

The median asking price was $810,500 as of 2026-10-04, or about $305 per square foot. The median single family home on the market is 3,479 square feet and was built in 2019.

How long do single family homes take to sell in Oakland?

Median days on market was 73 as of 2026-10-04. 16 of the 30 active single family homes, 53.33%, have been listed 60 days or longer, and that is usually where the negotiating room is.

Are Oakland single family homes cheaper than houses in Oakland?

The median single family home asks $810,500 against $796,000 for all Oakland listings, and $305 per square foot against $284 citywide. Price per square foot is the fairer comparison.

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.