The median home value in Oakland, FL is $588,000.
This is
higher than
the county median home value of $369,000.
The national median home value is $338,100.
The average price of homes sold in Oakland, FL is $588,000.
Approximately 79.18% of Oakland homes are owned,
compared to 12.37% rented, while
8.45% are vacant.
Oakland real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Oakland real estate agent to arrange a tour today!
Courtesy: THE REAL ESTATE COLLECTION LLC
407-656-7814
Office condo for sale. Selling both Units as 1. Units G1 & G2 are located side by side and have internal access to one another. Both units are located on the second floor of the office building in the heart of Oakland. Unit G1 if fully furnished, square footage is 1,970 includes reception area, conference room, 4 private offices, common workspace area, filing and printing room, extra storage room, bathroom and kitchen/breakroom area. Unit G2 is located by outside door from walkway or within G1 unit just off the kitchen is a hallway that leads into the G2 unit. Unit G2 is 700 square feet, includes private bathroom, kitchenette area with cabinets and a sink, large open space with vinyl flooring. Conveniently located close to state road 50, FL Turnpike, Downtown Winter Garden and Clermont.
Courtesy: KELLER WILLIAMS ELITE PARTNERS III REALTY
321-527-5111
Welcome to Oakland Trails which is situated on the West Orange Trail and in-between the popular downtowns of both Winter Garden and Clermont! This is a Meritage home that was built with beauty and energy efficiencies in-mind. The owners took it a step further by placing Tesla solar panels on the roof to easily support the whole-home and pool energy needs each month. There are 2 Tesla walls in the garage as well. The location of this home is ideal as it’s across the street from the community pool and mailboxes. Enter to find beautiful tile plank flooring, tray ceilings, and upgraded lighting fixtures. The gourmet kitchen has double ovens, a steam dishwasher, quartz countertops, tile backsplash and walk-in pantry. Entertaining is easy with the dedicated dining room which is spacious and still open to the kitchen and family rooms. Fill the home with sound as Sonos speakers were installed in the dining room and kitchen. Relaxation awaits in the primary suite with a luxurious garden tub, frameless shower with upgraded tile, dual vanities, dual walk-in closets and dedicated AC unit. The secondary bedrooms share a bathroom with a quartz countertop. The set of triple sliding glass doors extends the living space to the covered patio with automatic screens, heated and salt water lap pool, spa and spacious backyard. The French travertine tile is stunning and you’ll even find a fruiting Blue Banana tree! The garage has a dedicated AC unit as well, epoxy flooring and overhead storage. Additional upgrades include custom shelving in the laundry room, Ring doorbell, ADT security system and gutters. Oakland Trails is near the Turnpike and 429 so it’s easy to move around town. Don’t miss your chance to see this beautiful home!
Courtesy: BHHS FLORIDA REALTY
407-876-2090
*** NEW ROOF will be installed prior to closing *** Pre-holiday special-BRING YOUR OFFER! Experience LUXURY living in this stunning, CUSTOM-built POOL home, perfectly redesigned to capture elegance and modern comfort. Nestled in the charming town of Oakland in the GOLF CART DISTRICT with partial WATER views, this exceptional residence sits on over a quarter of an ACRE (.3) and features an open-concept layout with high-end finishes. The gourmet kitchen boasts premium appliances, while the expansive living area seamlessly connects to the outdoor oasis, offering a sparkling pool and a spacious covered patio, perfect for entertaining. This home has maximized its space by offering a family 5 bedrooms and 3 baths. The newly RENOVATED kitchen features Australian Dolomite counters, CAFE appliances, including an induction cooktop with vented hood, built-in oven with air fryer, built-in microwave/convection oven, and beverage fridge, under cabinet lighting, solid WOOD shaker cabinetry with soft close doors and drawers, tile backsplash, ample seating at the island, instant hot water and filtered water dispenser, and coastal style lighting to complete the design. Folding GLASS doors were added to enhance the indoor-outdoor living space. Step into your oasis for an evening by the SALTWATER-HEATED pool and enjoy a cold beverage by the fire-pit. The first floor is enhanced with wood plank TILE flooring, shiplap accent ceilings and walls, a STONE wood burning fireplace, updated vanities and mirrors in the baths, and a custom built laundry area. The downstairs PRIMARY suite connects to the pool deck through FRENCH doors and includes a dual vanity, TUB, shower, and walk-in closet. An additional room with Murphy bed is located downstairs, which could be utilized as an OFFICE, guest suite. Upstairs you’ll find three additional rooms and one full bath. One bedroom features a 3X10 area that can easily accommodate a desk. The middle room is unique in its design and could be used as a bedroom, play room, or office. The shower and vanity area in the upstairs bath is separated by a pocket door, providing privacy and freedom for use by multiple family members. Key UPDATES: extensive redesigned kitchen, interior PAINT (walls, trim, doors, & ceiling), first floor wood plank TILE, vinyl FENCE (2024), POOL heat pump and filter (2022), pool salt cell (2024), 4-ton AC (2021), 80 gallon Hybrid Water Heater (2024), water heater (~2/3 years old), lighting fixtures, flat LED recessed lighting, garage door opener, spring, & wheels (2021-2023), custom floor to ceiling garage shelving, and a new roof coming soon! Located in the golf cart district which connects to historic downtown Winter Garden where you can enjoy the brewery, shopping, outdoor dining, a play, the FARMERS MARKET, and so much more. Enjoy proximity to the Oakland Town Center, the 22 mile long West Orange Trail, Speer Park's playgrounds, tennis & pickleball courts, basketball courts, picnic areas, & the Healthy West Orange Arts & Heritage Center. Enjoy the tranquility of this peaceful neighborhood, with easy access to the Turnpike, East-West Expressway, 429, grocery shopping, theme parks, and golf courses, this home offers a lifestyle of unparalleled beauty and convenience. Embrace the enchanting OAKLAND-WINTER GARDEN lifestyle and make this exquisite residence your next place to live!
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Under Construction. Welcome to your dream retreat in the Central Florida's most coveted new community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. This custom-built masterpiece by Pioneer Builders blends timeless elegance with modern convenience, offering a quintessential French farmhouse style that exudes warmth and charm. Step inside this 5-bedroom, 4.5-bathroom haven and be greeted by an inviting open floor plan flooded with natural light, perfect for both family living and entertaining guests. The spacious living area boasts soaring ceilings offers a welcoming ambiance for gatherings or quiet evenings at home. The gourmet kitchen is a chef's dream, featuring top-of-the-line appliances, custom cabinetry, and a large island with ample seating. Whether you're hosting a formal dinner party or a casual brunch, this kitchen is sure to inspire culinary creativity. Retreat to the luxurious master suite, complete with a spa-like ensuite bathroom and oversized closet. Four additional bedrooms offer plenty of space for family members or guests, each thoughtfully designed with comfort and style in mind. Outside, discover your own private oasis with a custom pool, lush landscaping and a covered patio with summer kitchen perfect for al fresco dining or lounging in the Florida sunshine. Casita or in-law suite optional. With a 3-car garage providing plenty of storage space and a convenient location close to parks, schools, and shopping, this home truly has it all. Don't miss your chance to own this one-of-a-kind property in Oakland, FL. Schedule your private showing today and experience luxury living at its finest!
Courtesy: CT HOMES REALTY CORPORATION
407-578-6545
Check out this charming two-story Chandler Floor Plan from Meritage Homes, perfect for families who enjoy hosting guests of all ages! The open, spacious kitchen overlooks the living and dining areas, making it ideal for hosting dinner parties or game nights with friends! For your privacy, all bedrooms are located on the second floor, along with a loft that can be used as an office area or a playroom! Upgrades include a gourmet kitchen with granite counters, stainless steel appliances, and wood laminate floors! The property features a rear-load double garage with an oversized (pavers) driveway. Oakland Trails offers several amenities, including a resort-style pool, dog parks, and a playground. It's also conveniently located between Winter Garden and the City of Clermont, near shopping, restaurants, and major toll roads (Turnpike, 429, and 408). Don't miss this opportunity and contact us to schedule your private showing today!
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
***MOTIVATED SELLER - EASY TO SHOW - PRICED TO SELL*** Welcome to your dream home in the heart of beautiful Oakland. This stunning two-year-old, one-story residence boasts four spacious bedrooms and three luxurious baths, all designed in an open floor plan that complements modern living. On a serene conservation lot in a peaceful cul-de-sac, this home offers unparalleled privacy with a private fenced yard and a screen-enclosed patio, ideal for relaxing or entertaining. The home also features a charming brick-paved driveway and faces lush green space, adding to its picturesque appeal. Inside, you'll find incredible storage throughout, ensuring everything has its place. The primary retreat is a sanctuary, complete with a walk-in shower, garden tub, double sinks and a spacious walk-in closet. The convenience of an indoor laundry room near the bedrooms adds to the home's functionality. Additionally, the garage floors boast a sleek epoxy finish, enhancing durability and aesthetics. Conveniently near downtown Winter Garden and downtown Clermont, you'll enjoy easy access to vibrant shopping, dining and entertainment options. Nature enthusiasts will love the proximity to West Orange Trail and the Oakland Nature Preserve, ideal for weekend adventures. Commuters will appreciate the easy access to the Florida Turnpike, making travel a breeze. In the desirable Hull Island community, this home benefits from natural gas and offers an array of amenities including a sparkling pool, a fun-filled playground and a picturesque boardwalk with breathtaking views of Lake Apopka. Don't miss this exceptional opportunity to own a piece of paradise. Schedule your private tour today and experience the elegance and charm of this beautiful offering!
Courtesy: BHHS FLORIDA REALTY
407-876-2090
Experience the essence of WATERFRONT living in this stunning custom-built Key West inspired retreat, nestled on the tranquil waters of LAKE APOPKA, overlooking spectacular sunsets. Nearly 275 feet of waterfront & 1.12 ACRES could be yours. Nearby LAKE LOTS are up to 1M+. This tropical CORNER lot home brings classic island charm, offering breathtaking water views from nearly every room, & includes 4 bedrooms, 3.5 baths, & a large BONUS room (potential 5th bedroom) with balcony, which could be used as a MOTHER-IN-LAW suite or game room. Escape to your own serene paradise with the island-style SALTWATER POOL, framed by natural stone accents & a cascading waterfall. An expansive deck invites you to lounge under the sun or shade. Complete with an integrated heated SPA, the pool area is designed for seamless indoor-outdoor living, offering a peaceful escape from everyday life. Whether you’re enjoying a refreshing dip or hosting al fresco gatherings, this tranquil sanctuary is your personal slice of paradise. Step inside to discover an open concept living space, bathed in natural light & accented by vaulted ceilings, tile floors, a wood burning fireplace, FRENCH doors, & panoramic water views. The kitchen is equipped with a COOKTOP, built-in oven & microwave, two sinks, & ample storage & counter space. Two of the bedrooms are located on the west side of the home & are connected by a Jack & Jill bath. The 4th room would be ideal as an office & includes pocket doors with glass (no closet). The upstairs bonus area has a lot of potential & includes a full bath, wet bar with a mini refrigerator & sink, & its very own balcony overlooking the lake. The spacious downstairs PRIMARY suite offers an abundant of natural light, a fireplace, connection to the pool, spa-like bath with soaking TUB, & a walk-in closet with custom shelving. The laundry room is generous in size & includes a utility sink & additional storage. Bring your grill & connect to the gas line to complete your outdoor kitchen living. Venture to the SAND BAR & take in a romantic SUNSET by the fire-pit for a fun evening by the water. Additional UPDATES & features: ** FREE 2024 Massimo 4 seater GOLF CART **, high quality CertainTeed Carriage House roof shingles (2016), 12X30 steel SHED (2022) with covered porch, 2 walking doors, 2 garage doors & generator, whole-house generator (~ 2022), newer lakeside lower level doors (2022), spray foam insulated walls & attic, ultraviolet germ light in AC ducting, Shack Shine holiday lights, 2.5 GARAGE, & LOW HOA. Whether you’re taking in sunsets, kayaking from your backyard, or enjoying the vibrant local culture, this Key West-style oasis invites you to savor the laid-back Florida lifestyle. Located in the GOLF CART district which connects to historic downtown Winter Garden where you can enjoy the brewery, shopping, outdoor dining, a play, the FARMERS MARKET, and so much more. Enjoy proximity to the Oakland Town Center, the 22 mile long West Orange Trail, Speer Park's playgrounds, tennis & pickleball courts, basketball courts, picnic areas, & the Healthy West Orange Arts & Heritage Center. Conveniently located near the Turnpike, East-West Expressway, 429, grocery shopping, theme parks, & golf courses, this home offers a lifestyle of unparalleled beauty & convenience. Embrace the enchanting Oakland-Winter Garden lifestyle & make this exquisite residence your next place to live!
Courtesy: OAK AVENUE REAL ESTATE LLC
407-720-5000
LOT 264: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orang Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden, and 20 minutes to Disney property or 30 minutes to our international airport.
Courtesy: OAK AVENUE REAL ESTATE LLC
407-720-5000
LOT 262: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orang Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden, and 20 minutes to Disney property or 30 minutes to our international airport.
Courtesy: LAKESIDE REALTY WINDERMERE INC
407-876-5575
Nestled in the quaint Town of Oakland enjoy this 3 bedroom 2 bath home on a quiet street with oversized lot. Home offers a new roof 8/2024, HVAC 3/2024, and a hot water heater in 8/2024. Interior remodeled with new drywall, engineered hardwood flooring, fixtures and new doors. Home is close to Oakland Nature Preserve, West Orange Trail, Oakland Farmers Market, and the public park.
Courtesy: GLOBALWIDE REALTY LLC
352-456-9788
Prime opportunity to own a beautiful corner lot in the highly sought-after Winter Garden area of Orange County! This ready-to-build lot offers the perfect setting for your dream home, investment. Surrounded by scenic views, mature trees, and conveniently located near top-rated schools, shopping, dining, and major roadways, this property provides the tranquility of nature with the conveniences of city living. With close proximity to parks, recreational areas, and the vibrant downtown Winter Garden, this land is a blank canvas ready for endless possibilities. Don’t miss this chance to secure your piece of paradise in one of Central Florida’s fastest-growing communities!
Courtesy: LA ROSA REALTY ORLANDO LLC
407-288-7384
This one of a kind gem is located in the sought-out Oakland Trails community. Conveniently located with ready access to Orlando, Winter Garden, Clermont and the rest of the State via Route 50 and the Florida turnpike. A single family home that will check all of your boxes. Right on the West Orange trail. This 3 bedroom, 2 1/2 bathroom home duplicates your living space in the existent terrace with has an outdoor kitchen, living and seating areas. The oversized lot leaves plenty of room for the pool of your dreams. Family room, foyer and dinning room light fixtures DO NOT convey, nor does the Maytag water purifier, the fire pit and the outside lighting poles. Come with your offers as the Seller is highly motivated!
Courtesy: HOMEVEST REALTY
407-897-5400
Built in 2019, this stunning townhouse in Oakland offers contemporary living with all the amenities you could desire. Perfectly positioned for convenience, you're just minutes from the highway, making trips to Orlando a breeze, and only a short drive from the vibrant downtown Winter Garden. The home features luxury vinyl planking throughout the main level, enhancing both the style and practicality of the space. The open floor plan creates a warm and inviting atmosphere, ideal for entertaining guests or enjoying quiet evenings at home. Upstairs, you’ll find the spacious primary bedroom, providing a peaceful retreat at the end of the day. The secondary bedroom is also located upstairs and boasts its own en-suite bathroom, offering comfort and privacy for family or guests. One of the standout features of this townhouse is the large patio out back, perfect for outdoor dining, gardening, or simply unwinding after a long day. The neighborhood itself offers a community pool, providing a refreshing retreat on warm days. This townhouse truly has it all: modern design, prime location, and fantastic amenities. Another amazing benefit of this location is that the community is right across the street from the scenic West Orange Trail—perfect for biking, jogging, or leisurely walks. Schedule your tour today and experience the best of Oakland living!
Courtesy: OAK AVENUE REAL ESTATE LLC
407-720-5000
LOT 261: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden, and 20 minutes to world famous theme parks or 30 minutes to our international airport.
Courtesy: OAK AVENUE REAL ESTATE LLC
407-720-5000
LOT 246: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden, and 20 minutes to our famous theme parks or 30 minutes to our international airport. Buyer must use an Oakland Park approved custom home builder only: J&J Builders or RCB Homes.
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Pre-Construction. To be built. Introducing Briley Farm, an exquisite 111-acre sanctuary nestled in the historic charm of Oakland, Florida. Designed by renowned Element Home Builders, this brand-new architectural design evokes a Modern Farmhouse vibe, epitomizing luxury with a touch of heritage. A welcoming front porch creates small-town charm. The open kitchen connects to the family gathering areas. Top-of-the-line appliances and upscale finishes create a gourmet's dream. Step into a world of boundless elegance, where the open floor plan effortlessly merges indoor and outdoor living. The primary suite is luxe and expansive featuring a huge master closet, a private covered porch area, and a spa-like master bath. Entertain with ease as you transition from the expansive interior to the sprawling covered lanai and open patio with a fire pit, the summer kitchen makes al fresco dining a breeze. The sparkling pool and spa are a perfect gathering spot for relaxing. Entertain family and friends in this lavish resort-style outdoor space. With ample space for relaxation and recreation, Briley Farm is the quintessential backdrop for creating lasting memories with family and friends. This meticulously crafted residence boasts versatility and room to grow with 5 beds and 4 & 1/2 baths, ensuring every household member finds their perfect retreat within this idyllic oasis. Experience the epitome of refined living at Briley Farm—a timeless retreat where luxury meets tranquility amidst the natural splendor of Oakland's historic landscape.
Courtesy: ASCENT REAL ESTATE INC.
407-712-5779
Prime Location with Florida Turnpike Frontage! Motivated seller. This C-1 Zoned 1.02 acres is right near the border of booming Winter Garden and Clermont. Located just over a mile from the Highway 50 and only 20 minutes from Orlando. This property is a great location with heavy daily traffic counts. Perfect for a variety of possible uses such as: restaurants, hotel, hospital, medical center, funeral home, college/university, childcare facility, business offices, and much more! Next to Busy 7-11. Possible future golf access from surrounding neighborhoods. Land is Right off Florida Turnpike Exit. Land is cleared and ready for Immediate Buildout. Building construction site plan available. Site plan approved by county. Please See Oakland Zoning Codes for additional Zoning Use information.
Courtesy: RE/MAX TITANIUM GROUP
352-241-6363
PRIME LOCATION HWY 50 FRONTAGE. This C-1 Zoned 3.52 +/- acres is right near the border of booming Winter Garden (population 48,000) and just East of Clermont (population 44,000). Located just over a half mile from the Florida Turnpike and only 20 minutes from Orlando. This property is a great location with average daily traffic counts of over 25,000! Perfect for a variety of possible uses such as: restaurants, hotel, hospital, medical center, funeral home, college/university, childcare facility, business offices, and much more! See Oakland Zoning Codes for additional Zoning Use information. Possible future golf cart access from surrounding neighborhoods.
