Oakland, Florida listings for sale

$1,996,500 - Oakland, FL

1258 Ridge Lake Way Oakland, FL - Pre-Construction. To be built. Welcome 1258 Ridge Lake Way, nestled in the final phase of the sought-after Oakland Park community. This custom-built modern farmhouse by RCB Homes offers a perfect blend of style and comfort. Spanning just under 6,280 square feet, this two-story residence features four spacious bedrooms and four luxurious bathrooms, providing ample space for relaxation and entertainment. As you enter, you'll be captivated by the open-concept design that seamlessly connects the living areas, creating a warm and inviting atmosphere. The gourmet kitchen, with its state-of-the-art appliances and elegant finishes, is a chef's delight. Enjoy breathtaking views of Lake Apopka from your private cul-de-sac location, offering tranquility and privacy. With a three-car garage, there's ample room for vehicles and storage. Experience the perfect blend of modern living and serene surroundings in this pet-friendly oasis. Don't miss the opportunity to make this stunning property your forever home! Conveniently located just minutes away from downtown Winter Garden, residents enjoy easy access to a myriad of amenities, dining, shopping, and entertainment options. Embrace the coveted golf cart district lifestyle, offering unparalleled convenience and access to the best of Oakland Park and beyond. Explore the nearby West Orange Trail, offering endless opportunities for outdoor recreation and leisure amidst scenic surroundings. Don't miss the chance to call this exquisite property your new home. Schedule a showing today and seize the rare opportunity to immerse yourself in the luxury lifestyle of Oakland Park, Oakland, Florida. With its unparalleled amenities, scenic surroundings, and refined living spaces, this residence offers a lifestyle of unparalleled sophistication and comfort. Make it yours today!

$1,700,000 - Oakland, FL

1207 Ridge Lake Way Oakland, FL - Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours - YOUR WAY! The Oakland Park subdivision is a short walk on the West Orange Trail to downtown Winter Garden. Enjoy easy access to the community pool & clubhouse, dining, shopping & entertainment. This is luxury living at its best. Call us to discuss your options!

$1,499,900 - Oakland, FL

141 Millholland Street Oakland, FL - Live the "Lake Life" in a Tropical Paradise – Key West Vibes in Oakland, Florida! Welcome to your own slice of paradise in the heart of The Town of Oakland – one of Central Florida’s most desirable and fastest-growing communities. Situated on a sprawling 1.12-acre lot along the shores of Lake Apopka – Florida’s 4th largest lake – this gorgeous custom home spans nearly 4,000 square feet of beautifully designed space that embraces the outdoors at every turn. With 8-mile panoramic lake views that stretch across the water, you’ll wake up to breathtaking sunrises and unwind to the sounds of nature and incredible sunsets every evening. Just a short walk, bike or golf cart ride from the vibrant charm of Downtown Winter Garden, this Key West-style lakefront retreat blends luxury, nature, and laid-back living like no other. Step outside and into your own resort-style backyard, complete with a heated tropical pool oasis, cascading waterfall, spa, and hidden grotto, all surrounded by lush, vibrant landscaping that makes every day feel like a tropical getaway. Entertain guests, relax in the sun, or enjoy evenings by the lake under the stars – this backyard is pure magic! Inside, every inch of this home is built for comfort and peace of mind – including a whole-home Generac generator so you're always prepared. Whether you’re looking for a private retreat, love hosting unforgettable gatherings, or simply craving the serenity of a lakefront lifestyle, this home delivers. Best of all? You’re located within the golf cart district, just minutes from Plant Street Market, Crooked Can Brewery, charming restaurants, boutique shops, and everything downtown Winter Garden has to offer. You’re also just steps from the West Orange Trail – a 22-mile scenic mixed-use path that connects Oakland to Winter Garden and all the way to Apopka - perfect for biking, walking, skating, or just soaking up the Florida sun. This isn’t just a home – it’s a lifestyle. Come see it for yourself – paradise is waiting. Don’t miss the chance to make it yours!

$899,000 - Oakland, FL

70 Millholland Street Oakland, FL - BUYER failed to close. YOUR opportunity is knocking! *** NEW ROOF will be installed prior to closing with negotiated offer *** 2.25% ASSUMABLE mortgage is available (up to ~ 425K) *** 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 is located downstairs, which could be utilized as an OFFICE or 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!

$840,000 - Oakland, FL

1319 Johns Cove Ln Oakland, FL - Welcome to a home that blends comfort, function, and fun for all behind the gates of a peaceful, well-kept neighborhood just minutes from the turnpike. This spacious residence features a smart split floor plan with four generously sized bedrooms and five full bathrooms plus one half bathroom, including a guest suite perfect for visiting friends or extended family. Inside, custom cabinets and walk-in closets provide both beauty and practical storage, while the expansive kitchen and living areas create an ideal environment for gathering and relaxing. The bonus game room offers a dedicated space for entertainment or hobbies, giving everyone room to unwind. Step outside to enjoy your screened-in pool and dedicated pool bathroom, great for hosting weekend get-togethers or simply enjoying Florida's warm evenings without the bugs crashing the party. For the outdoor enthusiast, the community offers a private boat ramp for easy access to fishing, boating, and jet skiing just moments from your front door. A roomy two car garage with extended driveway ensures plenty of space for vehicles and storage, while the manicured setting provides a true sense of tranquility. With its thoughtful layout and desirable features, this home delivers convenience, comfort, and quality for everyday living and special occasions alike.Whether you're into early morning fishing, afternoon swims, or simply relaxing in your own space, this property offers something for everyone. Opportunities like this don’t stay available long, this one’s in a prime location with space to live, play, and make lasting memories.

$825,000 - Oakland, FL

1301 Johns Cove Lane Oakland, FL - Don’t miss out on this incredible opportunity within the sought-after Johns Cove gated community! This small, sought-after gated community on Johns Lake is ideally located just off the Florida Turnpike, close to Old Winter Garden, the airport, and all the Attractions. The community has its own private boat ramp, providing access to Johns Lake, which is renowned for fishing, boating, jet-skiing, and paddle boarding. Welcome to this stunningly, beautifully remodeled 4-bedroom, 2-bathroom custom pool home—truly turn-key and move-in ready! This home has been completely updated in 2024, offering stylish living and peace of mind from day one. From the moment you arrive, you’ll be impressed by the manicured lawn and vibrant flower beds. The side-entry two-car garage adds to the home’s fantastic curb appeal. Step inside through the foyer to a beautiful, freshly remodeled and painted interior that opens into a spacious dining area. This home features a split floor plan—with the primary suite and one bedroom on one side, and two additional bedrooms and a full bath on the other, offering flexibility for families and guests alike. The primary suite is a true retreat, complete with a luxurious en-suite bathroom featuring a custom tub, walk-in shower, and a stunning walk-in closet. All finishes, including elegant porcelain tile flooring, are brand new. The heart of the home is the expansive open-concept kitchen and living area, highlighted by an oversized quartz island with a farmhouse-style sink—perfect for entertaining. The custom-designed kitchen offers modern cabinetry, sleek finishes, and seamless access to the family room. Enjoy cozy evenings in the family room, which showcases a state-of-the-art electric fireplace and a custom entertainment bar. From here, step through the doors to your covered outdoor seating area and brand-new 2024 custom pool, featuring a sun shelf and tranquil water fountain—perfect for relaxing or hosting. Additional features: New roof, windows, HVAC system, and tankless water heater (2024), Fully fenced backyard—great for pets. Fresh exterior and interior paint (2024). This fully renovated home combines luxury, comfort, and convenience in one of the most desirable communities in the area. It won’t last long—schedule your private showing today!

$760,000 - Oakland, FL

2340 Standing Rock Circle Oakland, FL - Welcome to an extraordinary residence nestled in the highly sought-after Oakland Trails community—just steps from the scenic West Orange Trail and moments from the charm of downtown Winter Garden. This beautifully appointed home showcases sophisticated upgrades, including a striking custom stone accent wall in the main living and dining areas and matching stonework along the staircase, creating a seamless blend of rustic warmth and modern elegance. Prepare to be captivated by the show-stopping fifth bedroom, thoughtfully transformed into a boutique-inspired primary closet—offering a luxurious, walk-in experience that feels straight out of a designer showroom. Upstairs, a generous loft provides the ideal space for a playroom, media lounge, or family retreat. The chef’s kitchen is designed to impress, with ample space for entertaining and everyday living. Step outside and enjoy the privacy of having no rear neighbors - and with plenty of room for a pool. Additional highlights include a beautiful tile roof, a rare 3-car garage, and fully paid-off solar panels for energy efficiency and long-term savings. Ideally located near major roadways, this home offers both convenience and tranquility in one of the area’s premier neighborhoods. Don’t miss this opportunity to own a truly exceptional home in an unbeatable location.

$710,000 - Oakland, FL

729 Strihal Loop Oakland, FL - One or more photo(s) has been virtually staged. *Once-in-a-Lifetime Opportunity! **EXTERIOR PAINTING INCLUDED** PLUS 10k TOWARDS YOUR CLOSING COSTS** This stunning 6-bedroom, 3.5-bathroom pool home is the epitome of comfort and luxury! **New Roof**, **New AC**, and **New Quartz Countertops** make this home as fresh as it gets. Upon entering, you are greeted with soaring ceilings and an open, spacious layout — perfect for those who love to entertain. The large dining and living room combo flows effortlessly into an extra-large family room, and the expansive kitchen is a chef’s dream, featuring brand new quartz countertops, stove top, and dishwasher. The **master suite** is conveniently located on the **first floor**, offering ultimate privacy and comfort. Step outside to your private **screened-in pool** with a lush, beautiful backyard featuring the sweetest mango tree you'll ever find. Fresh interior paint and brand-new appliances are just a few of the home’s upgrades. Located in a **gated community**, this home ensures comfort, security, and peace of mind. **Don't miss out on this gem! ** - **5 Bedrooms** - **3.5 Bathrooms** - **Master Suite on First Floor** - **Screened Pool & Beautiful Backyard** - **Fresh Paint & New Upgrades** This home is ready for you to move in and enjoy! Bring your offers and make this home yours Today!!

$700,000 - Oakland, FL

2127 Bay Line Road Oakland, FL - WELCOME HOME TO HULL ISLAND! This home offers a serene retreat for those looking for a blend of modern living mixed with nature. The HIGH Ceilings and Large Windows create a light-filled and most inviting atmosphere. Step inside to an open floor plan featuring 4 Bedrooms, 4 Baths plus huge bonus room. Gorgeous WOOD-LOOK tile flooring throughout this OPEN-CONCEPT floor plan. Spacious kitchen is a standout feature, complete with 42-inch cabinetry, large island with farm sink, boast a gas stove, vented hood and stainless steel appliances. Kitchen opens to dining and living rooms offering the perfect areas for entertaining. The primary suite, tucked away for privacy at the rear of the home, is bathed in natural light through its expansive windows. The deluxe owner’s bath includes: his and her vanities and a frame-less shower with tile that extends to the ceiling. Two walk-in closet will have you wanting to go shopping to fill them. 3-way split plan features an en-suite bedroom and 2 secondary bedrooms that share a hall bath located at the opposite end of the home. Large bonus room is a perfect home office or 5th bedroom with private full bathroom. Just outside, you can enjoy your covered Lanai, overlooking the pristine conservation area, creating a peaceful and private outdoor oasis, perfect for morning coffee, evening drinks, or just relaxation. Other upgrades include an interior laundry room with a utility sink, blinds on all windows, brand new carpet in bedroom and a tankless gas hot water heater. Not to mention that the Location is Second to None! In this Lakefront Community, you will enjoy AMAZING Amenities, including the Community Pool, a lengthy Fishing Pier, a Charming Gazebo for those weekend picnics, as well as a Community Park, Bark Park, and Playground. Hull Island has a private entrance to Oakland Preserve nature trails. The Town of Oakland is a picturesque and historic area known for its gorgeous lakes, friendly atmosphere, and fantastic proximity to everything that Central Florida has to offer. You are MERE minutes to Shopping, Restaurants, the West Orange Recreation Trail, and an incredible Farmers Markets (every Saturday), in Downtown Winter Garden. You are also close to the shops and restaurants of Winter Garden Village, as well as Downtown Clermont’s amazing lake-view restaurants and shops. You are just a 30-minute drive from Downtown Orlando, Orlando International Airport, Hospitals, Attractions, and Major Roadways. You are only an hours’ drive from some of Florida's Finest Beaches.

$660,000 - Oakland, FL

410 E Gulley Avenue Oakland, FL - 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.

Oakland, Florida listings for sale

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