Oakland FL Homes for Sale

5 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

Beautiful 2022-built home in Hull Island featuring 5 bedrooms, 4 full bathrooms, approximately 3,781 heated square feet, a private pool, and a two-car garage. Open-concept living with a gourmet kitchen, quartz countertops, a spacious loft, and two primary suites, including one on the first floor. Community amenities include a pool, trails, playground, dog park, and private dock. Buyer to verify all measurements, HOA terms, and property details.

2010 Boss Hewett Street, Oakland

$1,627,000

4 Beds ⋅ 4 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Experience custom living at its finest in this beautifully crafted J&J Building home, ideally located in the heart of charming Oakland. Offering 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this home combines thoughtful design with modern appeal. The primary suite is conveniently located on the main floor, providing a private retreat. Enjoy Florida’s year-round sunshine and entertain with ease in the outdoor summer kitchen, perfect for gathering with family and friends. Situated directly across from Speer Park which features pickle ball, a tennis court and a basketball court. Located just moments from Lake Apopka, the West Orand Trail, three miles to downtown Winter Garden, and steps from the charm of downtown Oakland, this home offers a unique blend of outdoor recreation, small-town character, and custom craftsmanship. Don’t miss the opportunity to make this exceptional property your own!

20 W Vick Avenue Unit 2, Oakland

$1,645,000

4 Beds ⋅ 4 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Under Construction. Discover the perfect blend of custom craftsmanship, modern style, and small-town charm in this beautifully designed J&J Building home. Featuring 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this distinctive residence offers a thoughtfully designed layout with the primary suite conveniently located on the second floor. Sleek vinyl windows add a contemporary touch, while the summer kitchen creates the perfect setting for outdoor entertaining and enjoying Florida living year-round. Ideally situated across from Speer Park where you can enjoy an active lifestyle featuring pickleball, tennis, and basketball courts. Just up the street from Lake Apopka, the West Orange Trail, three miles from downtown Winter Garden, and right next to charming downtown Oakland, this home offers a wonderful opportunity to enjoy the beauty of nature and the appeal of a welcoming community, all close to home. Experience the best of custom living in a location that truly stands out!

20 W Vick Avenue Unit 1, Oakland

$695,000

5 Beds ⋅ 4 Baths ⋅ Johns Landing Ph 01 44/47 SubDv. ⋅ 34787 Zip Code

Welcome to 726 Regina Circle in Oakland, Florida! This spacious two-story home offers five bedrooms, four bathrooms, and an inviting layout designed to accommodate a variety of living needs. The interior features vaulted ceilings, a formal dining area, and comfortable living spaces, including a family room with a fireplace. The kitchen offers granite countertops, a breakfast bar, an island, and ample cabinetry, creating a functional space for everyday living and entertaining. The primary suite features an en-suite bathroom with dual vanities and a separate soaking tub and shower. Step outside to enjoy the private swimming pool and outdoor space, ideal for relaxing or entertaining guests. A two-car garage provides additional parking and storage. Conveniently located in the Oakland and Winter Garden area, the property offers access to nearby shopping, dining, parks, trails, and major roadways. Schedule your private showing and discover the possibilities this home has to offer.

726 Regina Circle, Oakland

$489,900

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

Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direct access to local walking trails. Built in 2018 and impeccably maintained, this home features an open-concept layout with towering 10-foot ceilings throughout. The main level boasts gorgeous tile flooring, a built-in office desk, a convenient wet bar, and carefully curated interior lighting that enhances the home's warm character and sophisticated ambiance. The gourmet kitchen shines with 42-inch refinished maple cabinets, updated hardware, quartz countertops, a stunning center quartz island, and a striking ceiling-height marble backsplash. Upstairs, enjoy the warmth of bamboo stairs and beautiful bamboo flooring across all bedrooms, each equipped with walk-in closets. Additional notable upgrades include quartz countertops in all bathrooms, beautiful zebra blinds, a 2026 refrigerator, and an epoxy-finished two-car garage. Step outside to exceptional exterior enhancements added in 2025 and 2026, including striking exterior accent lighting that delivers incredible nighttime curb appeal and presence, a fully sealed paver driveway, a welcoming front porch with ceiling fans, and an extended paver pathway wrapping around the house. Practical features include a brand-new gutter system connected to a downpour drainage system, plus a reliable irrigation system. Located in a top-rated school district, this home places you moments away from the scenic Oakland Nature Preserve, community parks like Speer Park, vibrant local farmers markets, rich cultural attractions like the historic Garden Theatre, and nearby dining favorites. Don't miss this incredible gem!

2199 White Feather Loop, Oakland

$364,900

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

Welcome to this beautifully maintained, fully furnished, six-year-old townhome in the charming town of Oakland! Featuring 2 bedrooms, 2.5 baths, and a two-car garage, this home combines abundant natural light with thoughtful upgrades and inviting outdoor space. A covered front porch welcomes you into an open great room featuring Shaw luxury vinyl tile flooring, neutral tones, recessed LED lighting, and dual-pane Low-E windows with cordless faux wood blinds. The kitchen offers 42-inch cabinetry, granite countertops, a gray subway tile backsplash, and a spacious island with upgraded pendant lighting and a large undermount sink. Appliances include a Whirlpool Gold microwave, range, and dishwasher, along with an LG French-door refrigerator. A generous pantry with a California Closets shelving system keeps everything organized. The adjoining dining area features upgraded lighting and a full-glass door with built-in blinds leading to a private 19-by-15-foot paver courtyard—an inviting setting for outdoor dining or relaxing. A built-in desk nook with granite countertops, drawers, and cabinetry provides a convenient workspace. The first-floor laundry room includes a California Closets laundry station and access to under-stair storage, while a half bath is located off the stair landing. Upstairs, both spacious bedrooms offer walk-in closets and private bathrooms. The primary suite features a California Closets organization system with a built-in vanity. Its ensuite bath includes dual sinks, granite countertops, Moen faucets, a private water closet, and a tiled shower with decorative accents, frameless glass, and an upgraded showerhead. The second bedroom’s private bath features granite countertops and a tiled tub/shower combination with an accent inlay. The courtyard connects to the two-car garage, complete with epoxy flooring and a Bluetooth-enabled opener. Additional features include gutters, a Taexx built-in pest control system, Nest thermostat, Ring security system and doorbell, Alexa-compatible front porch lighting, and prewiring for ceiling fans in the great room and bedrooms. Enjoy community walking paths, a playground, and a pool, with lawn care included in the HOA. Conveniently located near the West Orange Trail, downtown Winter Garden, downtown Clermont, Florida’s Turnpike, and Winter Garden Village, this home offers easy access to shopping, dining, recreation, and major roadways.

2107 Gopher Tortoise Terrace, Oakland

$849,000

4 Beds ⋅ 4 Baths ⋅ Hull Island/Oakland Ph 2 SubDv. ⋅ 34787 Zip Code

LOCATION, LOCATION, LOCATION. Come see this BEAUTIFUL, WELL MAINTAINED HOME BUILT IN 2022 WITH A CONSERVATION/PROTECTED PRESERVE VIEW in OAKLAND! This home looks like a MODEL HOME and is located in the HEART of OAKLAND! There will never be homes built across the street from you so in this location you only have homes built on ONE SIDE of the street making this STREET SO SPACIOUS! The home has an OPEN DESIGN and LUXURY VINYL PLANK THROUGHOUT most of the home! This ONE OWNER home has been maintained in pristine, LIKE NEW condition with SELLER ADDING OVER $90,000 IN CUSTOMIZATIONS to this home including being the ONLY HOME IN THE COMMUNITY with a CUSTOM BRICK ACCENT OPTION ON THE FRONT OF THE HOME. Home has a WATER PURIFICATION, FILTRATION, R.O. SYSTEM, CUSTOM CLOSET SYSTEMS, CUSTOM LAUNDRY ROOM, GARAGE FINISHED WITH EPOXY FLOORING AND SHELVING SUSPENDED FROM CEILING FOR TONS OF STORAGE Home also has TANKLESS GAS WATER HEATER AND GAS COOKING! This home has a beautiful kitchen with elegant choices, TONS OF CABINET SPACE, A CUSTOM-FINISHED WALK IN PANTRY, POTTERY BARN DRAPERIES and a CHEF’S DREAM for appliances. The home also has a beautiful covered and inviting front porch to welcome your guests and a large, covered back porch as well with a very private and beautiful backyard that has been IMMACULATELY MAINTAINED. The MASTER BEDROOM has two LARGE WALK IN CLOSETS, A HUGE WALK IN SHOWER IN THE MASTER BATHROOM AND A PRIVATE WATER CLOSET. The second floor has large guest bedrooms and a LARGE BONUS/MEDIA/GAMEROOM! COME LIVE IN THE HEART OF IT ALL YET TUCKED AWAY IN A PEACEFUL QUIET ENCLAVE on a PEACEFUL QUIET STREET. You will be located just steps from the WEST ORANGE TRAIL, a few minutes from HISTORIC DOWNTOWN WINTER GARDEN, 1 mile to the Oakland Nature Preserve, a few minutes to the Town of Oakland and parks, Less than 2 miles to the Florida Turnpike which makes getting anywhere easy, 6 miles to the WINTER GARDEN VILLAGE and steps to shopping, restaurants, boutiques and all! This home is in a HIGHLY DESIRED ADDRESS in the TOWN OF OAKLAND. Come visit this QUIET, FRIENDLY and SMALL NEIGHBORHOOD because you are sure to want to stay forever! Qualified buyers may receive a 1-year interest rate buydown for the first year paid for by the Seller's preferred lender when financing this home (subject to credit approval and program availability) also Seller Financing Available.

1213 Foltz Loop, Oakland

$1,050,000

5 Beds ⋅ 4 Baths ⋅ Hull Island SubDv. ⋅ 34787 Zip Code

Discover a private retreat in Hull Island at Oakland, an intimate community of limited residences offering a peaceful, exclusive feel near charming downtown Winter Garden and the celebrated West Orange Trail. Enjoy community amenities and a dock for taking in sunrise along Lake Apopka. With no immediate rear neighbors or neighbors on one side, this home backs to a conservation area for added privacy and a natural backdrop. Featuring 5 bedrooms, 4 full bathrooms and 3,658 square feet, the home offers an open kitchen, a versatile loft and a primary suite with its own screened porch overlooking nature. A rear patio with pavers and a covered screened enclosure creates an inviting setting for relaxing and entertaining. Room to gather, space to unwind and a setting to enjoy. Schedule your private showing.

1316 Southern Sun Drive, Oakland

$565,000

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

$367,500

2 Beds ⋅ 3 Baths ⋅ Longleaf At Oakland SubDv. ⋅ 34787 Zip Code

Set in Longleaf at Oakland, directly across from Oakland Nature Preserve and the 22-mile West Orange Trail, this END-UNIT TOWNHOME offers a rare combination of natural surroundings and everyday convenience. A covered front porch overlooking a large grassy area welcomes you home and provides a peaceful place to relax and enjoy beautiful Florida sunsets. ADDITIONAL WINDOWS fill the end-unit home with natural light and create a bright, open feel. UPGRADED luxury vinyl flooring flows throughout the first floor. The OPEN FLOOR PLAN brings the living spaces together, with spacious living and dining areas that flow naturally into the kitchen. UPGRADED 42-inch white cabinetry with crown molding, stone countertops, a tile backsplash, a generous island with additional seating and a LARGE WALK-IN PANTRY create an inviting and functional setting for everything from casual mornings to entertaining friends and family. Just beyond the main living area, a PRIVATE COURTYARD connects the home to the detached TWO-CAR GARAGE by a covered walkway. With the garage positioned separately from the home, the courtyard becomes a private extension of the living space for grilling, entertaining or unwinding outdoors. Offering 1,652 sf, the townhome features TWO BEDROOMS plus a large LOFT that can serve as a HOME OFFICE, MEDIA ROOM, PLAYROOM or additional living area, and 2.5 BATHROOMS. Both bedrooms are located on the second floor and have PRIVATE ENSUITE BATHROOMS, giving the second bedroom the comfort and privacy of a SECOND PRIMARY SUITE. The primary suite includes an expansive WALK-IN CLOSET, while the bathroom is finished with UPGRADED shower tile and an UPGRADED glass shower door. SMART HOME features, including a Ring doorbell, security camera and MyQ garage-door opener add everyday ease. ENERGY-EFFICIENT double-pane windows and a programmable Nest thermostat help keep energy use and monthly electric costs down. Tall oak trees enhance the community’s natural setting, along with a COMMUNITY POOL, PLAYGROUND and WALKING TRAILS. Just outside the community, you can spend mornings walking beneath the trees, head out for a bike ride or follow the WEST ORANGE TRAIL into HISTORIC DOWNTOWN WINTER GARDEN for dining, shopping and the award-winning Saturday Farmers Market. Here, you can feel connected to nature without leaving convenience behind. Florida’s Turnpike entrance is approximately one mile away, while everyday shopping, including the new Costco in Clermont, is less than 10 minutes from home. It is an ideal setting for enjoying a quieter community atmosphere while remaining connected to work, recreation and everything the surrounding area has to offer.

2224 Gopher Tortoise Terrace, Oakland

$600,000

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

$615,000

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

$730,000

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

$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. 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

$800,000

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

$1,445,000

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

$329,950

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

Virtually Staged. JUST REDUCED!!!!!!!!!!!!!!!!!!!!!! A well-maintained, stunning, and ready-to-move-in townhouse located in the highly desirable Longleaf at Oakland community. Built in 2019, this beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and 1,620 square feet of bright, open-concept living space designed for both relaxation and entertaining. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large and contemporary kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, with premium finishes that seamlessly flow into the main living and dining areas, making it ideal for both everyday living and entertaining. Upstairs, the primary suite serves as your private retreat, featuring an En-suite bath and ample closet space, alongside two additional bedrooms perfect for family, guests, or a dedicated home office. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community provides everything the Florida Lifestyle has to offer ! Living here means embracing an incredible Central Florida lifestyle. The Longleaf community features a sparkling resort-style pool with a cabana, a playground, and scenic walking paths. Best of all, you are just steps away from the historic West Orange Trail and the Oakland Nature Preserve, making outdoor adventures effortless. When you want to head out for dinner or shopping, the vibrant culture of downtown Winter Garden and the famous Plant Street Market are only minutes away. Plus, with quick access to major highways like the Florida Turnpike and SR-429, you are seamlessly connected to all of Orlando's world-class theme parks, dining, and entertainment. Don't miss the opportunity to make this beautiful turnkey property your own!

1511 Sweet Apple Street, Oakland

$559,000

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

$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

$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

$779,000

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

PRICE REDUCED! Make this 6-bedroom, 4-bath home in gated Johns Cove your own in time for the holidays. Set on a private cul-de-sac with no rear neighbors, it offers room to gather and space to unwind. Formal living and dining rooms, a large family room, vaulted ceilings, and a double staircase welcome you inside. The kitchen features stainless steel appliances, granite countertops, an island, and a breakfast area with pond views. The first-floor primary suite overlooks the pool and includes dual vanities, a garden tub, separate shower, and walk-in closet. Upstairs offers spacious bedrooms and a dedicated movie room. Enjoy a screened saltwater pool and spa, updated full pool bath, covered lanai, and private balcony. Residents have access to a private boat ramp on Johns Lake for fishing, boating, paddleboarding, and kayaking. Near West Orange Trail, Downtown Winter Garden, Winter Garden Village, shopping, dining, and schools. Motivated sellers are ready for their next chapter!

1603 Johns Cove Ln, Oakland

$2,495,000

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

LOCATED IN THE GOLF CART DISTRICT OF DOWNTOWN WINTER GARDEN, PLANT STREET! Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floor plan 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

$2,665,990

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

$649,900

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

$949,900

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

$999,000

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

$2,550,000

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

$1,975,000

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

$1,699,900

5 Beds ⋅ 4 Baths ⋅ Oakland Park B-2 SubDv. ⋅ 34787 Zip Code

Welcome home to calm, light-filled luxury on a peaceful pond in the sought-after golf cart district—just steps from the West Orange Trail and 3 miles to historic Downtown Winter Garden. This 4-bed, 3-bath custom home sits on a large lot and features an open, airy floor plan with upscale laminate flooring throughout. The gourmet kitchen is built to entertain: commercial-grade hood, gas range, Bosch appliances, pot filler, walk-in pantry, and appliance garage. Fully retractable sliding glass doors open the living area to the outdoors, with surround sound and custom-tinted windows adding comfort and privacy. One bedroom is on the main level; upstairs offers a Jack-and-Jill suite plus a private primary retreat with tray ceiling, spotlight accents, walk-in shower, soaking tub, and a stunning light-filled built-in closet. A rare bonus: a private in-law suite above the garage with its own kitchen, living area, bedroom, and stackable laundry—ideal for guests or multi-generational living. Outside, escape to your own oasis surrounded by bamboo, olive, lime, and persimmon trees, with a covered patio, full fencing, and even rocket launch views from your backyard. Unbeatable location. Unmatched lifestyle. Schedule your private showing today.

906 Allendale Lane, Oakland

$2,360,990

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

Under Construction. 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

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Oakland FL Homes for Sale

There are 33 homes for sale in Oakland, Florida as of 2026-10-30, at a median list price of $849,000 and a median of 63 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 listings	33
Median list price	$849,000
Median price per square foot	$287
Median size	3,430 square feet
Median year built	2019
Median days on market	63
On market 60+ days	17 (51.52%)
Priced below original asking	13 (39.39%)

Source: Stellar MLS via the Bridge RESO feed, pulled 2026-10-30. Updated weekly.

What the numbers say for Oakland buyers

13 of the 33 Oakland homes on the market (39%) are asking less than they did on day one, and 17 (52%) have been listed 60 days or longer. Those two figures are the practical case for making an offer here. A seller 63 days in who has already cut once is a different negotiation than one of the 16 listings still inside its first 60 days.

Across the 13 Oakland listings that have already come down, the typical reduction is 3.85% off the original asking price. That is the size of a first concession, not a final one.

Oakland homes by price range

Under $250,000	0	0.0%
$250,000 to $400,000	3	9.1%
$400,000 to $600,000	5	15.2%
$600,000 and up	25	75.8%

Property types in Oakland

Single Family Residence	30
Townhouse	3

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. Every one of the 33 Oakland listings carries a subdivision name.

Hull Island at Oakland6 active$824,500

Grove at the Harvest District5 active$2,495,000

Trls4 active$562,000

Oakland Town3 active$1,627,000*

Johns Landing3 active$695,000*

Longleaf at Oakland3 active$364,900*

Oakland Trails2 active$609,950*

Oakland Shores1 active$600,000*

Town at Oakland1 active$1,445,000*

Briley Farm1 active$3,295,000*

Johns Cove 43/1041 active$2,550,000*

Johns Cove1 active$779,000*

Oakland Park B-21 active$1,699,900*

Hull Island1 active$1,050,000*

Other Orange County Homescounty-wide

Subdivision names come from the MLS as agents entered them. Active count and median list price as of 2026-10-30. * 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.

More Oakland subdivisions

No active listing today. Each page keeps its sales history and refills as inventory changes.

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 (27 listings), 34760 (6 listings)

Oakland homes by property type

Frequently asked questions

How many homes are for sale in Oakland, FL?

There were 33 active residential listings in Oakland as of 2026-10-30, at a median list price of $849,000. 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 $849,000 as of 2026-10-30, or about $287 per square foot. The median home on the market is 3,430 square feet and was built in 2019.

How long do homes take to sell in Oakland?

Median days on market was 63 as of 2026-10-30. 17 of the 33 listings, 52% 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?

13 Oakland listings, 39.39% of the market, are now asking less than they did originally, at a median reduction of 3.85%. That is the size of a typical first concession here, and it is usually not the last one.

What neighborhoods are in Oakland, FL?

14 named subdivisions had at least one active listing in Oakland as of 2026-10-30, and every one is listed above with its active count and median list price. Hull Island at Oakland led with 6 active listings at a median of $824,500.

What zip codes cover Oakland, FL?

Oakland listings sat in 2 zip codes as of 2026-10-30: 34787 with 27 active listings, 34760 with 6 active listings.

Is Oakland a buyer's or seller's market?

By our local two-factor read, Oakland is a balanced market as of October 2026: 4.7 months of supply against 4.4 across the four counties, and sellers closing at 97.2 percent of original asking price against 96.0 percent regionally.

Full answer and method: Is Orange County a Buyer's or Seller's Market?

The Homes In Orlando Team at NextHome Neighborhood Realty works with buyers and sellers across six Central Florida counties and publishes market data for Orange, Seminole, Lake, and Volusia. Call or text 407-616-9019 to see any Oakland listing on this page.