Oakland Florida Homes for Sale

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

Listing courtesy of KELLER WILLIAMS CLASSIC. murraycoleman@kw.com

$1,275,000

3 Beds ⋅ 3 Baths ⋅ O6442710 MLS

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

Listing courtesy of EXP REALTY LLC. 888-883-8509

$1,495,000

4 Beds ⋅ 4 Baths ⋅ O6440357 MLS

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

Listing courtesy of REGENCY REAL ESTATE LLC. 407-469-5021

$199,000

2 Beds ⋅ 1 Baths ⋅ O6436879 MLS

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

Listing courtesy of OFFERPAD BROKERAGE FL LLC. 813-534-6326

$3,399,000

5 Beds ⋅ 7 Baths ⋅ O6434256 MLS

Set within the picturesque Briley Farm community in Oakland, Florida, this exceptional 5-bedroom, 7-bath estate offers an extraordinary blend of timeless design, spacious living, and resort-style amenities. Situated on an expansive 0.52-acre homesite, the residence encompasses approximately 5,092 square feet of beautifully designed living space, creating an ideal setting for both everyday living and unforgettable entertaining. Inside, soaring vaulted ceilings and thoughtfully designed living spaces create an impressive sense of scale and openness. A dedicated office provides the perfect environment for working from home, while the private sauna offers a peaceful retreat at the end of the day. A welcoming fireplace adds warmth and character to the home's elegant interiors. Step outside and discover your own private resort. The sparkling pool provides a refreshing escape, while the outdoor kitchen creates an exceptional setting for al fresco dining and entertaining family and friends. The spacious grounds provide plenty of room to relax and enjoy the peaceful surroundings of Briley Farm. The property also features a private sauna, three-car garage and a private casita/guesthouse, providing exceptional flexibility for guests, extended family, or a private retreat. Briley Farm offers a rare combination of tranquil countryside living and convenient access to the best of Central Florida. Located on 111 acres in Oakland, the community features resort-style amenities including pickleball courts, tennis, a basketball half-court, a resort-style pool, splash pad, and convenient golf-cart access to Downtown Winter Garden. A remarkable opportunity to own a truly exceptional luxury residence in one of Central Florida's most sought-after communities.

515 N Nixon Street, Oakland

Listing courtesy of REGENCY REAL ESTATE LLC. 407-469-5021

$415,000

3 Beds ⋅ 2 Baths ⋅ O6430972 MLS

Under contract-accepting backup offers. PRICE REDUCED - Accepting Offers! The home has recently been entirely staged on the inside of the property - come tour this BEAUTY! NOTE: to add extra storage, a (large shed) can be added onto the property within the purchase of the home. NO HOA! Welcome to this brand-new construction home in the heart of Oakland! This thoughtfully designed 3-bedroom, 2-bathroom residence offers 1,170 square feet of modern living space on a 0.09-acre homesite. The open-concept floor plan features luxury vinyl plank flooring throughout the main living areas and bedrooms, with porcelain tile flooring in both bathrooms for added durability and style. The kitchen is equipped with quartz countertops, modern cabinetry, stainless steel appliances, and a functional layout that flows seamlessly into the living and dining areas, making it ideal for everyday living and entertaining. Contemporary lighting, designer fixtures, and quality finishes can be found throughout the home. The primary suite includes a walk-in closet and an ensuite bathroom with a quartz vanity and a porcelain tile shower. Two additional bedrooms provide flexibility for family, guests, or a home office. Additional features include an indoor laundry area, energy-efficient windows, modern exterior finishes, and a paver driveway. Conveniently located near downtown Winter Garden, the West Orange Trail, shopping, dining, parks, major highways, and local attractions, this move-in-ready home offers the opportunity to enjoy low-maintenance living in the desirable Town of Oakland. Don't miss your chance to own this newly built home in one of Central Florida's most sought-after communities.

521 W Herriott Avenue, Oakland

Listing courtesy of REAL BROKER, LLC. 855-450-0442

$3,295,000

6 Beds ⋅ 7 Baths ⋅ O6429415 MLS

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

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155

$3,495,000

5 Beds ⋅ 6 Baths ⋅ O6405707 MLS

Luxury new construction model home by Element Home Builders located in the exclusive custom home community of Briley Farm in Oakland. This thoughtfully designed residence offers approximately 4,900 square feet of elevated living space with 5 bedrooms, 5.5 bathrooms, and a spacious 3-car garage. Designed for both everyday living and entertaining, the home features soaring ceilings, expansive open-concept living areas, designer finishes, and seamless indoor-outdoor flow. The chef’s kitchen is the centerpiece of the home with premium appliances, custom cabinetry, oversized island, generous prep and storage space, and a fully equipped back kitchen designed for seamless entertaining and everyday functionality. The luxurious primary suite offers a spa-inspired bath and oversized walk-in closet, while additional guest suites, flex spaces, and entertaining areas provide comfort and functionality throughout. Outdoor living is equally impressive with a resort-style pool, covered lanai, and beautifully designed entertaining spaces perfect for enjoying Florida living year-round. Professionally furnished by Arhaus, the home showcases elevated designer selections and a warm modern aesthetic throughout. Located just minutes from downtown Winter Garden, top-rated schools, restaurants, shopping, the West Orange Trail, and major highways, Briley Farm offers a rare combination of privacy, luxury, and convenience. This professionally designed model home is available with a lease-back opportunity from the builder, offering a unique investment opportunity with immediate income potential. A rare opportunity to own one of Central Florida’s premier luxury model homes in one of the area’s most desirable custom home communities.

402 N Pollard Street, Oakland

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155

$799,999

5 Beds ⋅ 3 Baths ⋅ TB8513260 MLS

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

Listing courtesy of JACK KELLER INC. 727-586-1497

$999,000

4 Beds ⋅ 3 Baths ⋅ G5110973 MLS

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

Listing courtesy of COAST TO COAST REAL ESTATE PRO. 352-296-8930

$619,000

4 Beds ⋅ 3 Baths ⋅ O6394442 MLS

Under contract-accepting backup offers. NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and low-maintenance living. Don’t miss the opportunity to own a move-in-ready home in Oakland, conveniently located near parks, trails, and local amenities. Schedule your private showing today!

38 S Pollard Street, Oakland

Listing courtesy of MS LAND & BUILDING LLC. 407-466-7000

$1,250,000

6 Beds ⋅ 8 Baths ⋅ O6362142 MLS

Under contract-accepting backup offers. PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!

620 N Tubb Street, Oakland

Listing courtesy of OAKSTRAND REALTY. 888-912-5258

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Oakland Florida Homes for Sale

Are you looking to buy or sell a home in Oakland Florida? Call or Text (239) 880-8850 to schedule a showing on any Oakland, FL home for sale or to sell your Oakland Florida home! As Realtors specializing in the Oakland area, we can take care of all of your Oakland FL real estate needs including buying pre-existing homes, new construction homes, condominiums, land, commercial and multi-family homes in Oakland Florida. We can also help you find distressed properties in Oakland including HUD Homes, Short Sales and REO Bank Foreclosures. If you need help financing a home in Oakland, we have access to some of the best lenders that service the Oakland Florida area, including lenders that offer credit repair to buy a home and work with home builders in and near the Oakland area to help you build your home while building up your credit. If you are going to buy or sell a home in Oakland Florida, then be sure to Call or Text (239) 880-8850 Today! We are a real estate team specializing in the Oakland, FL area! Displayed are homes for sale in Oakland, FL, a city located in Florida. These Oakland Listings are updated every 15 minutes from the Oakland MLS.