Oakland Town Homes for Sale

Oakland Town Homes for Sale

Welcome to Oakland Town, a picturesque subdivision nestled in the heart of Oakland, Florida, within the vibrant Orange County. This charming community is renowned for its serene atmosphere, friendly neighbors, and a strong sense of community that makes it a perfect place to call home.

Oakland Town boasts a variety of beautifully designed homes for sale, catering to diverse lifestyles and preferences. From cozy single-family residences to spacious modern designs, you’ll find a range of options that suit families, retirees, and everyone in between. Each home is thoughtfully crafted, often featuring open floor plans, lush landscaping, and state-of-the-art amenities that enhance your everyday living experience.

Living in Oakland Town means embracing a lifestyle that balances tranquility with accessibility. Residents enjoy easy access to local parks, scenic trails, and recreational activities that highlight the natural beauty of Central Florida. The community’s proximity to downtown Orlando ensures that you’re never far from shopping, dining, and entertainment options, while still being able to retreat to your peaceful haven at the end of the day.

Families will appreciate the highly-rated schools in the area, making Oakland Town an ideal choice for those looking to settle down and raise children in a nurturing environment. With a strong focus on community events and gatherings, neighbors quickly become friends, fostering a welcoming atmosphere where everyone feels at home.

Explore the homes for sale in Oakland Town today and discover the perfect blend of comfort, community, and convenience. Your dream home awaits in this enchanting subdivision!

Newest Oakland Town Homes for Sale

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

Virtually Staged. 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 spacious primary suite includes a walk-in closet and an ensuite bathroom with a quartz vanity and a porcelain tile shower. Two additional bedrooms offer 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

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. 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

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

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

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Uno Sorlie | Broker & Founder of HopKey Realty Orlando

Uno Sorlie is the Broker and Founder of HopKey Realty, a full-service real estate company focused on helping clients buy and sell homes across Central Florida. Originally from Norway, Uno moved to the U.S. in 2008 and quickly established himself in the real estate industry through hard work, deep market knowledge, and a passion for client service. Uno began his career in property management, overseeing vacation rentals throughout the Orlando area. By 2012, he transitioned into real estate sales, specializing in the same vacation and second homes he had been managing for years. This background gave him a unique perspective on both the investment side and the emotional side of homeownership — a combination that continues to benefit his clients today. Over the years, Uno has helped countless buyers, sellers, and investors navigate the Central Florida market with clarity and confidence. His hands-on experience with vacation homes, short-term rentals, and relocation clients allows him to provide strategic insight across a wide range of transactions. Uno is known for his transparent communication, calm demeanor, and commitment to doing what’s best for his clients — always. When he’s not working with buyers and sellers, Uno enjoys spending time with his family, traveling between Norway and Florida, and studying shifts in both U.S. and international real estate trends. Contact Uno today

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Mike Dudley | Orlando Realtor® at HopKey Realty

Mike Dudley brings nearly two decades of international real estate experience to HopKey Realty. His journey began in 2005 with his family’s business, Florida Villas Sales & Rentals, based in the UK, where he worked with British and European buyers and sellers seeking vacation and investment properties in Florida. In 2009, Mike and his family relocated their business to Central Florida, establishing a transatlantic presence with teams operating in both the U.S. and UK. Following the 2008 market crash, Mike founded the Dudley Elite Team, an international group specializing in residential properties and Disney-area short-term vacation rentals. His global network has connected him with clients from Colombia, Brazil, China, Canada, Europe, and across the U.S. Throughout his career, Mike has partnered with top brokerages across South and Central Florida and consistently ranked among the region’s top-producing agents. He was named one of Orlando’s Top 35 Agents Under 35 in 2020 and earned the ORRA YPN 20 Under 40 Rising Stars in Real Estate award in 2021. In 2023, he was recognized in the Top 1% of agents in Central Florida. Now a proud member of HopKey Realty, Mike continues to bring unmatched global perspective, negotiation expertise, and dedication to every client relationship — whether they’re right here in Florida or halfway around the world. Contact Mike today

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Amelia Ali | Orlando Realtor® at HopKey Realty

Amelia became a licensed Realtor® in 2023 and has quickly built a reputation for serving both buyers and sellers across Central Florida with professionalism and care. With over 11 years of experience as a Mortgage Loan Processor, she brings a deep understanding of the lending side of real estate—a perspective that allows her to expertly guide clients through every step of the home financing process. Her background gives her clients a distinct advantage in today’s competitive market, helping them navigate complex procedures with confidence and clarity. Whether you're buying your first home or selling your fifth, Amelia is committed to making the experience as smooth and stress-free as possible. Contact Amelia today

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