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$350,000
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
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521 W Herriott Avenue, Oakland
$499,999
3 Beds ⋅ 2 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code
Virtually Staged. Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and timeless appeal. Surrounded by mature landscaping and stately oak trees, this property offers a serene escape with no HOA to limit your creativity. Quiet dirt roads wind through the neighborhood, adding a touch of rural nostalgia, while the vibrant shops and cafes of Oakland’s quaint downtown are just a short stroll away. Inside, the home welcomes you with a warm and inviting layout. The living room, filled with natural light, provides a cozy space for relaxing or entertaining. It connects seamlessly to a well-appointed kitchen, featuring stainless steel appliances, granite countertops, and plenty of cabinetry for storage—ideal for home-cooked meals. The primary bedroom offers a peaceful retreat with a standard closet and an en-suite bathroom boasting dual vanities and a luxurious soaking tub. Two additional bedrooms, each with standard closets, provide versatile space for family, guests, or a home office, with a second full bathroom conveniently nearby. The exterior is a true highlight, with mature landscaping creating a private, tranquil setting. Towering oak trees provide shade and beauty, complemented by colorful, well-kept gardens. The spacious backyard is perfect for barbecues, gardening, or simply soaking in the calm of your own oasis. A charming front porch invites you to enjoy morning coffee while greeting neighbors on the peaceful dirt road. Located in the heart of Oakland, this home blends small-town charm with modern convenience. Enjoy local events, dining, and community spirit just steps away, with easy access to highways for commuting. With no HOA, you have the freedom to make this property your own.

409 E Gulley Avenue, Oakland
$500,000
Oakland Park SubDv. ⋅ 34760 Zip Code
Lot 262

1264 Ridge Lake Way, Oakland
$875,000
Oakland Park SubDv. ⋅ 34760 Zip Code
Lot 256

1269 Ridge Lake Way, Oakland
$2,353,078
4 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Welcome to La Cascina — a stunning semi-custom home by Pioneer Builders nestled among century-old oaks in The Grove at The Harvest District. This 4-bedroom, 4-bath, 2-half-bath home with a dedicated office impresses from the moment you step inside, with soaring vaulted ceilings, a dramatic floating staircase, and a natural gas fireplace that anchors the main living space with warmth and elegance. The thoughtfully designed layout flows from a formal dining room into an eat-in kitchen with a breakfast nook — perfect for everything from quiet mornings to lively gatherings. Two dedicated laundry rooms add a level of everyday convenience rarely found at any price point. Outside your door, golf-cart your way to Downtown Winter Garden's shops and restaurants— this is Florida living at its finest.

1204 Water Maple Drive, Oakland
$799,999
5 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code
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
$2,186,921
3 Beds ⋅ 6 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres in the beautiful Town of Oakland. The property is a seamless blend of charming Old Florida and modern-day Luxury Living at its finest. The community is thoughtfully designed to provide the ultimate retreat for our residents. Lot 15 will be custom pool home meticulously designed to complement its natural surroundings, with a spacious floor plan. Briley Farm offers a seamless combination of residential luxury and convenience, with custom homes designed for enjoying the best of indoor and outdoor living. At Briley Farm you'll discover comfortable countryside living amongst the welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

100 W Railway Avenue, Oakland
$2,395,000
5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 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, and a spacious loft across 3,712 square feet of elegantly curated living space—where classic design meets modern sophistication in the main house. Enhancing both versatility and privacy, the property also includes a beautifully appointed 785 square foot garage casita with its own private entrance, complete with a living room, kitchenette, bedroom, and full bathroom—ideal for guests, multigenerational living, or a private home office retreat. 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.

1137 Prado Lane, Oakland
$2,045,357
5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Nestled within the exclusive Grove community in the heart of Oakland and Winter Garden's coveted golf cart district, this bespoke pre-construction residence is a rare opportunity to own something truly one-of-a-kind. Five bedrooms, five full bathrooms, a powder room, and a gracious loft unfold across 3,725 square feet of living space where timeless architecture and modern sophistication coexist effortlessly — every detail considered, every finish deliberate. Element Home Builders has built its reputation on craftsmanship that doesn't cut corners and design that doesn't follow trends — because the Clementine wasn't designed to be fashionable. It was designed to be unforgettable. Step outside and you're two minutes from the West Orange Trail and just a short golf cart ride from the vibrant energy of Downtown Winter Garden — boutique shopping, acclaimed dining, weekend farmers markets, and the kind of small-town charm that's increasingly impossible to find this close to the city. This isn't just a home. It's a lifestyle you'll never want to leave.

1225 Water Maple Drive, Oakland
$1,654,248
4 Beds ⋅ 5 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Discover the opportunity to build your dream home in the sought-after Briley Farm community with J&J Building. This thoughtfully designed custom residence will feature 4 spacious bedrooms and 4.5 luxurious bathrooms, blending timeless craftsmanship with modern comfort. From the moment you arrive, an oversized front porch welcomes you with classic Southern charm—perfect for relaxing evenings and morning coffee. Inside, the open and functional layout is ideal for both everyday living and entertaining, with high-end finishes and attention to detail throughout. Enjoy seamless indoor-outdoor living with both side and rear porches, offering additional space for gathering, grilling, or simply taking in the peaceful surroundings. The home also includes a three-car attached garage, providing ample room for vehicles, storage, or hobbies. Each bedroom is designed with comfort and privacy in mind, while the primary suite will serve as a true retreat with a spa-inspired bath. With 4.5 bathrooms, convenience is built into every corner of the home. This is your chance to personalize a beautifully crafted home in Briley Farm—where quality construction meets a serene, upscale setting.

360 N Jefferson Street, Oakland
$629,999
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current market conditions, this property presents an excellent opportunity for buyers seeking newer construction without delays or renovation needs. A compelling option for buyers looking for value, condition, and immediate occupancy.

38 S Pollard Street, Oakland
$1,949,000
5 Beds ⋅ 5 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code
Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space. Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy layout. The main living areas seamlessly blend together, creating the perfect setting for entertaining, with a spacious great room flowing into a designer kitchen complete with a large island, walk-in pantry, and premium finishes. The primary suite, conveniently located on the main level, offers a private retreat with a spa-inspired bathroom and generous walk-in closet. Upstairs, you’ll find additional bedrooms along with a versatile loft space ideal for a media room, office, or play area. Designed for the Florida lifestyle, the outdoor living space is truly exceptional. Enjoy a resort-style pool and spa, expansive lanai, and dedicated firepit area—perfect for relaxing or hosting gatherings year-round. Additional highlights include a two-car garage with a separate golf cart bay, high ceilings, and thoughtful architectural details throughout. This is a rare opportunity to own a beautifully crafted home in one of the area’s most desirable communities.

511 Briley Avenue, Oakland
$683,000
3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code
Beautifully renovated pool home in the desirable Town of Oakland, within the golf cart district, and no HOA. Located in an area seeing significant growth with nearby luxury new construction and vacant lots selling for a premium, this property offers both charm and long-term value in one of West Orange County’s most sought-after locations. This updated single-story ranch home features a bright, open layout with the kitchen flowing seamlessly into the living room. The renovated kitchen includes quartz countertops, updated cabinetry, and a large island with eat-in seating, creating a great space for everyday living and entertaining. The living room is warm and inviting with a wood-burning fireplace and plenty of natural light. Recent improvements include a new kitchen, updated bathrooms, new flooring, new windows, interior and exterior paint, gutters, and a resurfaced pool and paver pool deck. A spacious enclosed Florida room with large windows and a slider that overlooks the backyard and pool, providing additional living space filled with natural light. The home also features a very large indoor utility room that could easily function as a home office, flex space, or additional storage. Outside, you’ll find a large in-ground pool and a fully fenced backyard, perfect for relaxing or entertaining. Located just minutes from downtown Oakland, the West Orange Trail, and Plant Street in downtown Winter Garden, offering easy access to restaurants, shops, and community events. Updated pool homes with no hoa in this area are very rare.

310 E Gulley Avenue, Oakland
$88,000
Oakland Town SubDv. ⋅ 34760 Zip Code
An exceptional opportunity to build your dream residence in the charming and highly desirable Town of Oakland, Florida. This beautiful homesite offers the perfect canvas for a custom home surrounded by the character, tranquility, and small-town elegance that Oakland is known for. Ideally positioned near the scenic West Orange Trail, residents enjoy easy access to miles of biking and walking trails, picturesque natural surroundings, and a vibrant outdoor lifestyle. The property is also just minutes from the historic charm, dining, and boutique shopping of nearby Winter Garden, Florida. With convenient access to major roadways including Florida State Road 50 and Florida's Turnpike, commuting to the greater Orlando, Florida area, world-class attractions, shopping, and dining is effortless. As a courtesy to the Buyer(s) Seller is providing copy of the Survey to the Buyer(S). The survey is for informational purposes only. It is not current and may not reflect recent changes. Buyer(s) is responsible for verifying all property boundaries and obtaining an updated survey if required. Buyer(s) may have a discount showing this courtesy survey to the company Buyer(s) choose to get an update survey,

406 W Herriott Avenue, Oakland
$395,000
34760 Zip Code
Sold Data Entry.

329 E Gulley Avenue, Oakland
$2,300,000
4 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Situated within the exclusive Grove community, this custom-built La Cascina residence by Pioneer Builders delivers refined luxury and exceptional craftsmanship throughout. Offering 4 bedrooms, 6 bathrooms, and 3,902 square feet of thoughtfully designed living space, this new construction home blends timeless design with modern comfort. The open-concept floor plan features expansive living and dining areas highlighted by vaulted ceilings in the living room, a fireplace, and seamless indoor-outdoor flow. The gourmet kitchen showcases premium finishes and connects effortlessly to the main living spaces, making it ideal for both everyday living and entertaining. A private office provides a dedicated space for work or study. The primary suite offers a serene retreat with a spa-inspired bath, while each secondary bedroom includes an ensuite bathroom for added privacy. A standout feature of the home is the interior sauna, offering a true wellness experience within the comfort of your own residence. Outdoor living is elevated with a custom pool and spa, summer kitchen, and covered entertaining areas designed for year-round enjoyment. Additional highlights include a 3-car garage and high-end finishes throughout. Located just a 10-minute golf cart ride from downtown Winter Garden and a 2-minute walk to the West Orange Trail, this home combines luxury living with unmatched access to recreation, dining, and shopping.

1118 Sarah Mathews Drive, Oakland
$395,000
Oakland Heights SubDv. ⋅ 34760 Zip Code
Looking for the best little town near Orlando? Oakland has so much character and charm. New construction in all around up to 4M. You now have the chance to build your custom dream home.

321 E Gulley Avenue, Oakland
$2,675,000
4 Beds ⋅ 5 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Custom Home by Element Home Builders

1179 Prado Lane, Oakland
$360,000
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintained, this home features 3 spacious bedrooms and 2 full bathrooms. The open and inviting floor plan offers a bright living room filled with natural light, a cozy family room ideal for relaxing, and a large dining area that’s perfect for hosting gatherings. The welcoming foyer greets you with a flexible space that can be used as a home office, reading nook, or a stylish sitting area. The kitchen boasts ample cabinet space, modern appliances, and a breakfast bar for casual dining. Additional highlights include: Central air conditioning and heating throughout the home Ceiling fans with lighting in each bedroom Freshly painted interiors with neutral tones Brand new Laminate wood-style flooring for easy maintenance Indoor laundry area for added convenience Fully fenced yard offering privacy and security Gated driveway with plenty of parking space Spacious backyard perfect for pets, play, or outdoor entertaining Whether you’re looking for your first home, a family retreat, or a peaceful escape close to everything, 507 W Oakland Avenue is the perfect choice. Don’t miss out on this rare gem — call today to schedule your private tour and experience the charm of Oakland living!

507 W Oakland Avenue, Oakland
$57,000
Oakland Town SubDv. ⋅ 34760 Zip Code
If you're looking for land in Oakland, you have certainly found it! Located in the most picturesque neighborhood in central Florida, this beautiful lot could be the site of your next home. Oakland is quaintly situated in between Winter Garden and Clermont, blending small town feel with activity brimming everywhere you turn.

121 S Nixon Street, Oakland
$450,000
Town/Oakland SubDv. ⋅ 34760 Zip Code
Discover this rare 0.31-acre residential lot in the heart of Oakland, one of the most charming and fastest-growing towns in Central Florida. Tucked just a few blocks from downtown Oakland, you’ll find yourself surrounded by the area’s signature tree-lined unpaved and stone roads, giving the neighborhood a warm, small-town character that’s hard to find today. Oakland continues to grow with new, luxurious communities, yet opportunities like this, a vacant lot with no HOA in the downtown core, are truly uncommon. From here, you’re just minutes to Plant Street in downtown Winter Garden, with its award-winning restaurants, local shops, and vibrant events, while still enjoying the peaceful lakeside setting Oakland is known for along the shores of Lake Apopka, one of Florida’s largest lakes. This property blends charm, convenience, and location, an ideal setting to build your dream home in a community that feels both timeless and connected.

N Daniels Street, Oakland
$300,000
Briley Farm SubDv. ⋅ 34760 Zip Code
As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to opportunity to build with one of three of Central Florida’s leading custom home builders, Element Home Builders, Pioneer Builders, and J&J Builders. Each residence will be meticulously designed to complement its natural surroundings, with spacious floor plans that flow from room to room, planned to be airy yet cozy and ready for your personal touch. At Briley Farm, you'll find a seamless combination of residential luxury and convenience, with homes built for enjoying the best of indoors and out. Briley Farm boasts serene scenery as a picturesque backdrop for new home construction, while still near shopping, restaurants, and major highways. At Briley Farm you'll discover comfortable countryside living under a canopy of welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

380 N Jefferson Street, Oakland
$375,000
The Grove SubDv. ⋅ 34760 Zip Code
Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home. Set in the illustrious community of The Grove, Lot 41 is a generously sized corner lot ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal location. Access to modern amenities, including walking trails, parks, and recreational areas. Close proximity to top-rated schools, shopping, dining, and entertainment. Easy access to major highways, ensuring seamless connectivity to Orlando and surrounding areas. This homesite is your chance to become part of a vibrant and growing community while enjoying the privacy and comfort of a custom-built home tailored to your lifestyle. Don’t miss this opportunity to secure your spot in one of Oakland’s most desirable locations.

1225 Water Maple Drive, Oakland
$390,000
3 Beds ⋅ 1 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Welcome to 121 W. Oakland Ave. This Charming Bungalow is in the heart of Oakland, you can walk to the Farmers Market on Thursdays, and the downtown area to include West Orange Biking trail and adorned Speer park. Situated on a corner lot, this property offers added privacy & w/ fenced in yard and wooden deck for entertaining. As you enter from the cozy front porch, you are captivated by the spacious living room with vaulted ceilings and Hardwood flooring with a stunning Brick wood burning fireplace. The primary bedroom and the other 2 bedrooms all have hardwood flooring as well. The kitchen is appointed with lots of counter space and natural sunlight overlooking the backyard. For added convenience, the dining area is just off the kitchen. NO HOA>>>>Oaklands quaint town is a stones throw away from Bustling Winter Garden, Clermont, and Disney can be found within 25-30 mins drive. Convenient to all major Arteries & shopping too. Schedule your private showing today and experience the beauty of this "one of a kind" home.

121 W Oakland Avenue, Oakland
$480,000
4 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Discover the wonderful blend of functionality, efficiency, and flexibility in this beautifully maintained two-story home nestled in the heart of Oakland, FL. Built in 2006, this 4-bedroom, 2-bathroom residence offers a rare opportunity to enjoy modern amenities, income potential, and eco-conscious living—all just minutes from the West Orange Trail and charming downtown Winter Garden. Property Highlights: - 1,680 sq ft of well-designed living space - Fully fenced in backyard - No HOA – enjoy the freedom to use your property your way - Solar-powered with a robust 15kWh system, keeping energy costs low - Dual HVAC systems for optimal comfort on both floors - Full kitchen downstairs + half kitchen upstairs — possibilities of in-law suite, rental potential, or multi-generational living - 14' x 12' elevated deck / covered patio — outdoor entertaining or private oasis - Optional furnished sale for a move-in ready experience - 10' gate to access backyard— boat, RV, or trailer storage - 18' x 22' carport as well as 12' x 30' gravel lot offers ample parking - Roof estimates available—opportunity for buyers to personalize or negotiate Outdoor Appeal: A spacious backyard offers room to expand patios, garden, or build additional outdoor amenities. The elevated deck and gated access make it both functional and private—perfect for Florida living. Location: Enjoy small-town charm with easy access to major highways, schools, parks, and the community of Oakland. Zoned for top-rated schools and close to everything Central Florida has to. Don't miss your chance to own this energy-efficient, flexible-use property in a sought-after location.

312 W Hull Avenue, Oakland
$450,000
3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code
Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space. Inside, enjoy a warm and functional layout with 1,419 sq ft of living space and central heating and cooling. The living room is perfect for relaxing evenings by the fire, while the outdoor area is built for Florida living—splash in the pool or unwind under the shade of the trees. Located just minutes from downtown Winter Garden and the West Orange Trail, you’ll love the peaceful setting with quick access to local shops, restaurants, and parks.

310 E Gulley Avenue, Oakland
$367,500
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Historic Oakland! Welcome to 500 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home features an open floor plan with thoughtfully designed living space and NO HOA restrictions! You’ll fall in love with the bright, clean, and welcoming feel throughout with brand-new flooring and fresh interior paint. The heart of the home is the completely renovated chef’s kitchen, featuring all-new cabinets, sleek countertops, and modern appliances—perfect for anyone who loves to cook or entertain. Enjoy the flexibility of a main-level bedroom and full bathroom, ideal for guests, multigenerational living, or a private home office. Upstairs, you’ll find two additional bedrooms and another full bathroom, offering comfort and privacy for the whole family. Set on a peaceful, nature-filled corner lot with attached an garage plus plenty of parking Residents of the 34760 zip code enjoy the unique charm of mail pickup at the historic Oakland Post Office, where you’ll also find the latest issue of the Orange Observer and a quaint Little Free Library out front. Oakland also hosts a variety of beloved community events, including Heritage Day, Santa meet-and-greets, Easter egg drops, and weekly farmers markets in-front of the Heritage Center, an ever changing art gala. The town is a scenic rest stop along the West Orange Bike Trail and is home to numerous parks and landmarks. Speer Park features two playgrounds, tennis, pickleball, and basketball courts. The Jake Voss public fishing pier provides a peaceful spot for watching sunsets on Lake Apopka. Prairie House Coffee serves local coffee, baked goods, floral arrangements, and gifts inside a charming 1860s residence. Disney enthusiasts will love Recycling the Magic, which offers an eclectic shopping experience filled with Walt Disney World props, resort decor, and memorabilia. Just 3.5 blocks from the upcoming boutique district at 300 S. Tubb Street, this location offers walkability to a future hub of shopping, dining, and community spaces—modeled after Winter Garden’s beloved Plant Street. Nearby, luxury estate communities like Briley Farm and The Grove are bringing multi-million-dollar homes to Oakland, setting the stage for strong equity growth. This is your chance to own a move-in ready gem in Oakland at an affordable value!

500 W Oakland Avenue, Oakland
$604,000
5 Beds ⋅ 3 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code
Charming 1959 Gem in the Town of Oakland with In-Law Suite. Find where timeless character meets small town charm in the heart of Oakland, FL. This beautifully maintained 4-bedroom, 2-bath, plus the Multi-generational suite home offers almost 2,500 square feet of living space, blending vintage appeal with the comfort and flexibility today's buyers are seeking. Nestled on a quiet street just minutes from the West Orange Trail and the scenic beauty of Lake Apopka, this unique property is perfect for those who appreciate the warmth and personality of a home with history. This mid-century home residence showcases many of its original features—from the striking parquet style ceiling in the living room along with the built-in shelving, to the exposed beams in the dining room, this home is inviting and full of character. The home’s thoughtful layout includes the spacious in-law suite that includes a private entrance and an ADA accessible bathroom, prime for multigenerational living, hosting guests, or creating a private work-from-home retreat. Step inside and discover generously sized bedrooms and a living space that flows effortlessly through the dining space overlooking your outdoor oasis. Step out onto the vaulted ceiling, screened-in lanai that overlooks a spacious backyard—perfect for relaxing evenings, lively gatherings, or enjoying Oakland’s peaceful atmosphere. Whether you’re looking for a forever home with vintage charm or an opportunity to personalize a home with great bones, this is your canvas. Don't miss your chance to own a piece of Oakland's history! Schedule your private showing today and experience firsthand the character, comfort and community this home has to offer.

410 E Gulley Avenue, Oakland
$410,000
Town/Oakland SubDv. ⋅ 34760 Zip Code
Discover this RARE 0.31-acre residential lot located in the charming town of Oakland, one of the most desirable and rapidly appreciating areas in West Central Florida. Just a few blocks from Oakland’s historic downtown, this property is set on picturesque unpaved and stone roads, adding a unique character and peaceful atmosphere to the neighborhood. Oakland is known for its warm community feel, seasonal events, and its privileged location along the shores of Lake Apopka, one of Florida’s largest lakes. Additionally, it borders the sought-after area of Winter Garden, renowned for its vibrant historic downtown, local restaurants, excellent infrastructure, and appeal as a top destination for Central Florida residents. This lot offers the perfect blend of serenity and convenience, ideal for building your dream home in a location that combines nature, culture, and close access to everything you need. Bonus: The seller already has a custom home project available, featuring 4 bedroom suites, 6 bathrooms, 2 offices, a den, and a bonus room. The planned layout includes 3,850 sqft of air-conditioned space and a total construction area of 5,024 sqft, offering a spacious and well-designed floor plan ready to be brought to life.

N Daniels Street, Oakland
$795,000
4 Beds ⋅ 3 Baths ⋅ Town Of Oakland SubDv. ⋅ 34760 Zip Code
Experience the charm of Oakland living in this beautifully updated custom built home located in the heart of town—just minutes to Downtown Winter Garden, Plant Street Market, the West Orange Trail, the Lake Apopka boat ramp/dock and so much more! This move-in ready home is situated on a .27-acre corner lot with no HOA. When entering this 4-bedroom, 3-bathroom home, you’re welcomed by a spacious front patio, beautiful foyer and open floor plan, perfect for entertaining. The flex space to the left of the front entryway offers a great space for an office, secondary dining area or den. The living room overlooks the breathtaking kitchen and exterior screened in patio with beautiful views of the private backyard. The downstairs bedroom and full bath offer flexibility, while the spacious upstairs includes a stunning primary suite with dual closets, and an en suite bath. There are two additional bedrooms upstairs with a shared Jack and Jill bathroom, as well as, a large laundry room with a stackable washer & dryer, sink and plenty of cabinet and countertop space. This home boasts countless updates throughout, including, but not limited to, New Taj Mahal quartzite countertops + backsplash (2024), brand new kitchen sink, hardware and faucet (2024), High end appliances and a brand new gas stove (2025) perfect for the chef at heart! The office features new custom built-in shelving (2024), and the entire interior has been freshly painted (2024). Stylish new fixtures, mirrors, and an updated fireplace façade add to the elegant aesthetic (2024). Move in stress free with upgrades such as a Newer Metal Roof (2022), Shingle Roof (2014), consistent servicing of the HVAC system, Double-Pane Windows throughout and new Plumbing & Electric (2014). Enjoy Florida living in your gorgeous backyard oasis—complete with new sod (2024), lush landscaping, a paver patio, hot tub, and a spacious screen-enclosed brick paver patio with an outdoor kitchen area. This home is truly turn-key and perfectly positioned for nature lovers, golf cart enthusiasts and downtown living alike. Don’t miss this rare opportunity to own this wonderful home in the sought-after Oakland neighborhood—schedule your private showing today!

101 W Oakland Avenue, Oakland