Oakland Schools and Nearby Homes for Sale and Rent

Please click on one of the below schools to see properties that are marked as being nearby those schools in the MLS.


Middle Schools

High Schools





Newest Oakland Homes by School

  • 70 MILLHOLLAND STREET, OAKLAND, FL - MLS# O5799491

    West Orange High - O5799491 - 70 MILLHOLLAND STREET, OAKLAND, FL 34760
    3 Days on yellowkey

    $475,000 | Single Family Home | 4 beds | 3.0 baths

    Enjoy LAKE breezes, sunsets, PARKS, the highly sought after West Orange Trail for biking or exercising, then top it off w/ an afternoon summer swim in your private POOL! Nestled amongst oaks in the quaint town of Oakland, adjacent to Winter Garden, & just minutes to historic downtown is this custom built, open floor plan, 4/3+BONUS room w/ solar heated POOL, screened enclosure, covered patio for outdoor entertainment, & WATER VIEWS. MASTER suite is to the back right of the home & features French doors to the pool, wood floors, garden TUB, shower, dual sinks, GRANITE counter, walk-in closet, & private toilet. Living area includes high ceilings, French doors to the patio, & a wood burning fireplace for cool winter nights! Kitchen features GRANITE counters, STAINLESS appliances, & walk-in pantry. Just past the kitchen is the dining area which can be dressed up formally or kept as a casual setting. Laundry is located downstairs. Travel upstairs to find two bedrooms, full bath, & LOFT which would be a perfect spot for a theater room. Full bath includes dual sinks, tub/shower & toilet w/ water views! Upstairs hallway overlooks the living room which adds a more open feel. Just minutes to the Turnpike, highway travel, shops, restaurants, Oakland Nature Preserve, & infamous downtown Winter Garden. Enjoy a stroll to the public dock to catch a breathtaking sunset over Lake Apopka or take a ride on your golf cart. Homes in Southern Oaks don’t last long! Schedule your showing today!!

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    Listing is courtesy of: BHHS FLORIDA REALTY

  • 1915 WHITE FEATHER LOOP, OAKLAND, FL - MLS# O5797887

    West Orange High - O5797887 - 1915 WHITE FEATHER LOOP, OAKLAND, FL 34787
    10 Days on yellowkey

    $336,575 | Single Family Home | 3 beds | 2.5 baths

    Under Construction. Brand NEW energy-efficient home ready July 2019! The Whitaker's open kitchen overlooks the family room and living room and the upstairs game room can be set up for work or play. Enjoy the outdoors on the front porch, back lanai, or courtyard. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429. Known for their energy-efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills.

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    Listing is courtesy of: MERITAGE HOMES OF FL REALTY

  • 1921 WHITE FEATHER LOOP, OAKLAND, FL - MLS# O5797891

    West Orange High - O5797891 - 1921 WHITE FEATHER LOOP, OAKLAND, FL 34787
    10 Days on yellowkey

    $343,859 | Single Family Home | 3 beds | 2.5 baths

    Under Construction. "Under Construction" Brand NEW energy-efficient home ready October 2019! The Whitaker's open kitchen overlooks the family room and living room and the upstairs game room can be set up for work or play. Enjoy the outdoors on the front porch, back lanai, or courtyard. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429. Known for their energy-efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills.

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    Listing is courtesy of: MERITAGE HOMES OF FL REALTY

  • 1939 WHITE FEATHER LOOP, OAKLAND, FL - MLS# O5797897

    West Orange High - O5797897 - 1939 WHITE FEATHER LOOP, OAKLAND, FL 34787
    10 Days on yellowkey

    $309,733 | Single Family Home | 3 beds | 2.5 baths

    Under Construction. "Under Construction" Brand NEW energy-efficient home ready October 2019! Enjoy the functionality of the open kitchen, living room and lofty dining area that opens to the second floor of the beautiful Chandler home. Relax on the front porch or use the optional upstairs pocket office for tackling home and paperwork. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429. Known for their energy-efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills.

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    Listing is courtesy of: MERITAGE HOMES OF FL REALTY

  • 1945 WHITE FEATHER LOOP, OAKLAND, FL - MLS# O5797906

    West Orange High - O5797906 - 1945 WHITE FEATHER LOOP, OAKLAND, FL 34787
    10 Days on yellowkey

    $330,193 | Single Family Home | 3 beds | 2.5 baths

    Under Construction. "Under Construction" Brand NEW energy-efficient home ready October 2019! The Kipling's open kitchen overlooks dual living areas on the first floor. Upstairs loft separates the master suite and bedrooms for privacy. Relax on the lanai or in the courtyard. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429. Known for their energy-efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills.

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    Listing is courtesy of: MERITAGE HOMES OF FL REALTY

  • 1999 WHITE FEATHER LOOP, OAKLAND, FL - MLS# O5797881

    West Orange High - O5797881 - 1999 WHITE FEATHER LOOP, OAKLAND, FL 34787
    10 Days on yellowkey

    $356,975 | Single Family Home | 3 beds | 2.5 baths

    Brand NEW energy-efficient home ready NOW! Enjoy cooking in this Baldwin home’s gourmet kitchen with quartz countertops and farmhouse kitchen sink. Tranquil dry pond views from front porch and balcony. Additional features include upgraded vinyl floors. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429. Known for their energy-efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills.

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    Listing is courtesy of: MERITAGE HOMES OF FL REALTY

  • 2327 STANDING ROCK CIRCLE, OAKLAND, FL - MLS# G5017682

    West Orange High - G5017682 - 2327 STANDING ROCK CIRCLE, OAKLAND, FL 34787
    16 Days on yellowkey

    $345,000 | Single Family Home | 3 beds | 2.5 baths

    Move-In Ready, ENERGY STAR Certified Home! The home features stunning modern finishes throughout and Beautiful front porch. The Gourmet Kitchen has a large island overlooking the dining room and living room, double ovens, cook top, 42” white cabinets with crown molding, granite countertops, upgraded stainless steel appliances, back-splash and pendants lights. First floor has Elegant Vinyl Plank, except powder room, 10’ high ceiling with 8’ doors and 5¼ baseboards. The stairs, leading up to the loft and 3 bedrooms are upgraded to the aluminum rail with stainless steel cables, and the upstairs loft is spacious to fit your family’s needs. The Master Suite has a tray ceiling & 4 recess lights, and both bathrooms have double sinks with granite countertops. The home is conveniently placed between two streets, providing a long parking pad in the back, easily fitting 6 cars beside the 2 in the over-sized 2 car garage. Cool off in the community pool, while the kids play at the park. The Community is walking distance to the West Orange Trail and conveniently close to Central Florida's major employment, services, main highways and entertainment corridors including Disney Springs and Walt Disney World. Known for their energy-efficient features, this home will help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills. The house also comes equipped with a Ring Doorbell with camera, Smart switch and thermostat. This house offers over $35K in upgrades.

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    Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC

  • 2749 BOBCAT CHASE BOULEVARD, OAKLAND, FL - MLS# O5794045

    West Orange High - O5794045 - 2749 BOBCAT CHASE BOULEVARD, OAKLAND, FL 34760
    27 Days on yellowkey

    $365,950 Increased | Single Family Home | 4 beds | 3.0 baths

    Under Construction. BRAND NEW HOME - MOVE IN THIS SUMMER! Enjoy the best of both worlds at this peaceful oasis in a prime location. Located across from Oakland Nature Preserve, this new home allows you to escape stress and relax in nature. Long commutes are shortened with proximity to Florida’s Turnpike and the 429. Spend the day at local restaurants/farmer’s markets in Downtown Winter Garden and unwind as you enjoy Florida beauty on the West Orange Trail. The Seamist floorplan offers a private bedroom with full bath on the main floor, ideal for guests or a home office. Create meals for your loved ones in the kitchen while overlooking mature landscaping including preserved Oak Trees. This home has no rear or front neighbors. Spend the evening outside on the oversized covered lanai that features beautiful brick pavers. This home is priced to sell and sure to make you feel like you’ve found “home.” Longleaf at Oakland is a fully maintained community located conveniently off Oakland Avenue and W Colonial Drive. Community features a cabana area, pool, playground, and trails that lead to the West Orange Trail. Come see everything Longleaf at Oakland has to offer! Pictures for illustration purposes only. Options may vary.

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    Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC

  • 15250 SUNSET OVERLOOK CIRCLE, OAKLAND, FL - MLS# O5791541

    West Orange High - O5791541 - 15250 SUNSET OVERLOOK CIRCLE, OAKLAND, FL 34787
    38 Days on yellowkey

    $475,000 Reduced | Single Family Home | 5 beds | 3.0 baths

    Fall in love with this stunning home situated in Lake Pointe Community! This 5-bedroom, 3-bath home has lots of upgrades to offer. The welcoming exterior is enhanced by mature landscaping, 3-car garage and a well-maintained driveway. This house also offers a screened-in pool, outside shower and a deck for lounging. The interior boasts brilliant features with high ceilings, a separate dining area, an open floor plan, living room and a spacious family room, enhanced by carpet and ceramic tile flooring. The fully-equipped kitchen comes with solid wood cabinets, granite countertops and stainless appliances. Has an attic and a bonus room that can be an office or game room based on your needs. Living here also gives you access to John Lake Pointe's amenities such as a resort-style pool, clubhouse, playground and a tennis court. A 25-min drive to Disney and other attractions, this must-see home is perfect as a primary residence or a retirement home.

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    Listing is courtesy of: ELEVATE REAL ESTATE BROKERS

  • 912 JOHNS POINT DRIVE, OAKLAND, FL - MLS# O5789229

    West Orange High - O5789229 - 912 JOHNS POINT DRIVE, OAKLAND, FL 34787
    47 Days on yellowkey

    $1,625,000 | Single Family Home | 5 beds | 6.0 baths

    Stunning Mediterranean Lakefront home located on beautiful Johns ski-lake in a private gated community of Custom Homes. This exquisite 6065 sq. ft Lakefront home features 5 bedrooms, 6 bathrooms, a 4-car spacious garage and an infinity edge pool and amazing lake views. Features include soaring vaulted coffer ceilings, hardwood floors, a glass enclosed and temperature controlled wine cellar with additional butler’s bar with sink and ice maker. A private elevator takes you to a fully equipped 6 seat Home Theater. The magnificent Formal living room has a a gas fireplace and custom builtins. Surround sound both inside and outside, an upstairs large game room and gym over look the lake. Experience the Florida Lake Life that includes a Large Screened Lanai with a Summer Kitchen. Enormous Uncovered Paver Patio for entertaining, Outdoor Shower, Vanishing Edge Pool and Spa. This house comes with a covered boat dock with a ski boat lift and 2 jet-ski lifts. The chef-inspired kitchen has top of the line Viking appliances, Murano glass light fixtures and a curved sink in the middle of the center Granite island – perfect for entertaining. The master suite, is spacious and luxurious with Lake Views and a dry bar and mini refrigerator to cap an amazing Private space. The Master Bath has a Soaking tub and and a walk through shower join the His and Her separate bathrooms. Owner is an Agent The Downstairs Guest Ensuite assures all guests feel pampered.

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    Listing is courtesy of: STIMMELL REALTY

  • 520 LARGOVISTA DRIVE, OAKLAND, FL - MLS# O5781202

    West Orange High - O5781202 - 520 LARGOVISTA DRIVE, OAKLAND, FL 34787
    59 Days on yellowkey

    $1,700,000 | Single Family Home | 5 beds | 5.0 baths

    Pre-Construction. To be built. LAKEFRONT luxury custom home opportunity on Johns Lake! Take out the boat or jet skis from your own private dock. Pool and spacious yard overlooking the lake with Southwestern views for nightly sunsets. Downstairs master with a large upstairs guest suite for family and friends. This home also boosts home theater room, game room, second-floor bonus room, bar, large balcony, patio, eat-in kitchen, formal dining, full laundry upstairs and down, and summer kitchen. Located for quick access to Florida's Turnpike, Clermont, Gotha, Winter Garden, and Walt Disney World.

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    Listing is courtesy of: THE HOPE GROUP

  • 1101 BOBCAT CHASE BOULEVARD, OAKLAND, FL - MLS# O5784774

    West Orange High - O5784774 - 1101 BOBCAT CHASE BOULEVARD, OAKLAND, FL 34787
    66 Days on yellowkey

    $345,710 Increased | Single Family Home | 3 beds | 2.0 baths

    Under Construction. BRAND NEW HOME - ALMOST COMPLETE! If you are looking for a peaceful place to call home, look no further. This brand-new home offers mature landscaping with no rear or front neighbors and views of the beautiful West Orange Trail. Located across from the Oakland Nature Preserve, you will find your place to relax and feel undisturbed. The open floor plan and kitchen with central island allows you to entertain your loved ones. Spend the evening outside on the front patio enjoying scenic Florida skylines or grill out back on the covered lanai that features beautiful brick pavers. This plan is priced to sell and sure to make you feel like you’ve found “home.” Longleaf at Oakland is a fully maintained community located conveniently off Oakland Avenue and W Colonial Drive. Commuting from this location is a breeze with close proximity to the Florida Turnpike and 429. Community features a cabana area, pool, playground, and trails that lead to the West Orange Trail. Come see everything a home in Longleaf at Oakland has to offer! Pictures for illustration purposes only. Options may vary.

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    Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC

  • 1805 STANDING ROCK CIRCLE, OAKLAND, FL - MLS# O5771982

    West Orange High - O5771982 - 1805 STANDING ROCK CIRCLE, OAKLAND, FL 34787
    121 Days on yellowkey

    $374,990 Reduced | Single Family Home | 4 beds | 3.0 baths

    WHY WAIT TO BUILD THIS MODEL HOME IS MOVE IN READY. !!!! If you been dreaming of an energy-efficient, two-story home in the Winter Garden area? Well then, WELCOME HOME to Oakland Trails! Home is sure to impress! This beautiful 4 Bedroom/ 3 Bath Energy efficient Meritage Home construction offers plenty of natural light, tray ceilings & recess lighting. Guest are greeted by entering a lovely foyer, which leads to a beautiful gourmet kitchen includes, 42” white cabinetry, granite countertops, Kenmore elite glass top range, dishwasher, and microwave, Refrigerator as well as a built-in convection oven. Recess lighting and pendant lighting over the large island granite countertops. Kitchen is open to the light & bright living area, great for entertaining! Inside second-floor laundry room with linen closet as well as pre-plumbed for a future laundry sink. Glass French doors lead out to the covered patio. master bath offers large dual walk-in closets, luxurious dual shower. Enjoy West Orange Trail, Shopping at Winter Garden Grove, & Convenient access to turnpike entrance & 429! Come make this your new home today! SELLER WILL PAY CLOSING COSTS !!

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    Listing is courtesy of: PARK PLACE REALTY & INVESTMENT

  • 306 N TUBB STREET, OAKLAND, FL - MLS# O5769198

    West Orange High - O5769198 - 306 N TUBB STREET, OAKLAND, FL 34760
    132 Days on yellowkey

    $425,000 Reduced | Single Family Home | 6 beds | 3.0 baths

    Stop the Car...It may take a minute to take ALL of this one in! This Historic Home was Built in 1886 before the beautiful Town of Oakland was established in 1887! This beautiful home has all of it's elegance and character carried through for over a century! With more than ten total rooms including formal dining room, living room, library, game room, and more it has all that you need to create and unbelievable atmosphere for family, guests, entertainment and more! This home features an upstairs balcony in the front and back so you can relax and enjoy looking at Downtown Oakland, or gazing out over the larger than 1/2 acre fenced lot in the backyard! Maybe it's future holds as the most inviting Bed and Breakfast in Central Florida. History, elegance, and beauty are already here! The only word to describe the Town of Oakland is Historical with its original brick roads, large oak trees, nature preserve, blocks from the pier on Lake Apopka. Speer Park is located across the street with playground, tennis courts, picnic tables, pavilion and more for family and friends. Highly rated Oakland Avenue Charter School is just moments away! This town has it all, and this unbelievable home sits right in the middle of it all in Downtown Oakland. It has also been CONFIRMED that this large lot can be subdivided into three separate lots!! Plenty of land if a builder brings the plans! This is a MUST SEE!! Schedule your showing today!!

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    Listing is courtesy of: GO REALTY LLC

  • 237 LARGOVISTA DRIVE, OAKLAND, FL - MLS# S5011453

    West Orange High - S5011453 - 237 LARGOVISTA DRIVE, OAKLAND, FL 34787
    198 Days on yellowkey

    $325,000 Reduced | Single Family Home | 3 beds | 2.5 baths

    Beautiful Home with 3 bedrooms 2 and a half bathroom in a Lakefront, gated community. This is a move-in ready home with 3 car garage. High ceilings light off the entrance. Huge master bedroom downstairs with a sitting area and sliding doors that offers access to screened lanai; a very spacious master bath with separate tub and shower and walk in closet.A formal living room and dinning room separated from the family room. Kitchen has a nook area. Upstairs will find an enormous loft and 2 bedrooms that are bigger for an average room and a full bathroom.The spacious loft is big enough to add 2 new rooms. With excellent location, this subdivision is located just off Hwy 50, near the turnpike entrance which puts you minutes from Downtown Orlando, the resort areas, shopping, restaurants, and more. The community offers a private boat ramp, tennis courts and a playground.

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    Listing is courtesy of: RE/MAX PRIME PROPERTIES

  • 239 LARGOVISTA DRIVE, OAKLAND, FL - MLS# O5731553

    West Orange High - O5731553 - 239 LARGOVISTA DRIVE, OAKLAND, FL 34787
    323 Days on yellowkey

    $377,000 Reduced | Single Family Home | 4 beds | 2.5 baths

    Lovely Home Poised On Spacious Lot In the Fabulous Gated Lakefront Community With Tree Lined Streets Of John's Landing. Step inside and be impressed with the open floor plan and high ceilings leading to the massive family room with pretty Bamboo wood floor over looking the large covered porch and lovely back yard. This home is very spacious and you will be pleased with the bright and cheerful living room and dining room and the large Den / Office. The kitchen comes with pretty granite counters, Lovely cabinets and pretty ceramic tiles including the dinette area. The master suite is downstairs and features a lovely & Spacious glamour bath with separate tub and shower and huge walk in closet. All bedrooms are Spacious. There is a huge bonus media / theatre room or Man's cave upstairs. There are so many closets you will be very happy. This gated community offers a tennis court, play area and the community boat dock for the residents here on John's lake. This pristine lake is known for Bass fishing. Here you will be close to everything - the turnpike, the 429 Hwy, shopping and all major conveniences. This home awaits you today.

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    Listing is courtesy of: RE/MAX 200 REALTY