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$1,600,000
5 Beds ⋅ 5 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
Introducing 100 Millholland St, an immaculate modern contemporary Custom-Built Home in the heart of Oakland! Situated in the coveted community of Southern Oaks, this home sits on just under a Half-Acre Elevated Lot boasting unparalleled Sunset Lakefront Views. Entering the home, you’re captivated by the Custom Saltwater Aquarium and Expansive Open Floor Plan featuring 20ft Ceilings in the Great Room with Floor to Ceiling Glass. The Luxury Kitchen features a beautiful island with seamless access to the pool deck, perfect for entertaining guests. Off the Great Room you’ll find a stunning, Formal Dining room encompassed by panoramic glass windows overlooking the lake. The awe-inspiring first-floor Primary Suite offers sanctuary with its 12ft Ceilings, a Floating Fireplace, and a Vast Picture Window framing Picturesque Lake Views. French Doors lead to the pool, while two expansive walk-in closets and a lavish Primary Bath await within, boasting a Large Steam Shower, Modern Soaking Tub, and a stylish Double Vanity illuminated by pendant lighting. Completing the first floor is a versatile Private Office/Bedroom and a spacious Bonus/Game/Pool Cabana Room with a luxurious Pool Bath and Private Entry, perfect for a Mother-in-law’s Suite! Ascend to the second floor to find a Second Primary Suite featuring Vaulted Ceilings, French Doors opening to an Oversized Balcony overlooking the lake, and an Ensuite Bath with Glass Shower, Garden Tub, and Dual Vanities. Another ensuite bedroom is located on this level as well. Travertine pavers lead you through the rock garden to the Incredible backyard Oasis where you’ll find the Multi-Level Pool and Fire Pit Deck that’s surrounded by stunning rock landscaping and artificial turf! The Heated Pool features a Large Spa, Sun Shelf with Bubblers and Digitally Controlled LED Lighting. There are also Two Large Covered Lania’s paired with the 20ft x 10Ft Fire Pit Deck features a 6ft Travertine Fire Pit offering the ideal outdoor setup for entertaining and family fun! The Home also Features Ensuite Bathrooms and Built-In Closets in all Bedrooms, Two Laundry Rooms, a Custom Stamped Concrete Driveway, Security System, Extensive Subsurface Drainage/Repurpose Watering System, 400 AMP Power Service and more. Originally built in 2015 with a recent Addition and Renovation in 2023, this home exudes meticulous attention to detail and maintenance. The home sits on a Corner Lot with no neighbors to the north and east offering privacy and unobstructed lakefront views. The home is also located directly beside Oakland Park, walking distance to the West Orange Trail and in the Golf Cart Friendly Zone of Winter Garden allowing a short ride to Downtown Winter Garden and its famous Shops, Restaurants, Bars and Breweries! This home is truly one-of-a-kind and a rare find in the Oakland/Winter Garden area! Call today to schedule a tour! Must See Marketing Video - https://player.vimeo.com/video/933670698?autoplay=1

100 Millholland Street, Oakland
$725,000
4 Beds ⋅ 4 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code
Discover the charm of this 4-bedroom, 3.5-bathroom single-family home in Oakland, Florida, boasting 2836 sq ft and a 2-car attached garage with NO HOA. Recently painted inside and out, this beautiful home features a new roof and numerous elegant updates throughout. Inside, an open floor plan includes a formal dining room (or office space) and breakfast nook, with the master suite conveniently located on the 1st floor, featuring a bath with double vanities and a walk-in shower. Two additional bedrooms, a full bathroom, and a half bathroom for guests are also on the 1st floor, while the 2nd floor offers a versatile bonus room suitable for various needs, along with the fourth bedroom and third full bathroom. Enjoy outdoor relaxation on the screened back porch. Located in the Golf Cart District just minutes from Historic Downtown Winter Garden, hop in your golf cart and enjoy local restaurants, shops, and a weekly farmers market with ease. Enjoy a morning or evening walk or run on the West Orange Trail located just a block away, or stroll down to Historic Downtown Oakland, where you can enjoy a large community park and playground, have a scoop of ice cream and other treats from Oakland General, see the seasonal community art at the Healthy West Orange Arts and Heritage Center, take in stunning Lake Apopka views at the nearby pier, or partake in the numerous community events put on by this charming small town, including holiday events, block parties, and local farmers’ markets. Don't forget to enjoy Florida's natural beauty at the Oakland Nature Preserve. Take advantage of the proximity to desirable schools, including Oakland Charter School and the international magnet program at Tildenville Elementary. This home is nestled among the historic oak trees of Oakland but conveniently located just minutes away from the Turnpike and SR 429 for easy access to Downtown Orlando and Disney World. Don't miss out on the opportunity to make this home your own—schedule a showing today!

206 Mather Smith Drive, Oakland
$842,500
3 Beds ⋅ 3 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code
Oh, what an amazing area Oakland is!! Even more amazing is this three-bedroom home with two and half baths featuring a massive 25x15 loft over garage. New Fresh Look the owners gave it, now we are up to new build standards and beyond. Impressive dental crown in the living areas. With the Recently completed Kitchen Renovation, walls were removed to open the floor plan to give you a spacious feel. Kitchen features a Wolf induction stove with a commercial grade hood with lights and a multitude of fan speeds. Z-Line dishwasher cabinet front. KitchenAid refrigerator, Huge farm sink sits in the middle of the quartz island that has additional deep cabinets below so you won’t need a ladder to get whatever it is you have stored. Over the Top quiet close cabinets deep for all your pots and pans with the coolest hardware for handles. All adorned with quartz backsplash. Two huge pantries that have pull out drawers and fully equipped with electricity for those appliances you want out of sight. French doors lead out back to a tropical paradise. With its lush landscaping you wouldn’t know you had neighbors. Just installed motorized awnings to prolong your days out back enjoying the pool area. Enjoy yearlong soaking in the upgraded led lights and heated pool. Your days will be perfect for recreation and relaxation. After your morning walk or run on the West Orange trail. You won’t be able to contain yourself thinking of the COMPLETE PRIVACY your Lot offers. When you get back to take a dip in your private oasis pool. Let's don’t forget to mention your magical side entrance. Stroll through the courtyard with pavers, fenced in along with beautiful hedges surrounding its perimeter giving the privacy desired. A second outdoor getaway location to be enjoyed! The Oversized garage is Nestled amongst the majestic oaks of Downtown Oakland and Winter Garden. Beautifully appointed in one of Oakland’s most sought-after neighborhoods. This residence is strategically positioned in the highly desired Golf Cart District. Just jump on your golf cart and in minutes you are in Historic Downtown Winter Garden. Also enjoy preferred enrollment & walking distance to renowned Oakland Charter School. Nestled just a stone's throw away from the West Orange Trail, this property provides easy golf cart access to the vibrant Downtown Winter Garden, brimming with an array of restaurants, shops, a weekend farmers market, and an abundance of family activities. Enjoy 22.26 miles of paved Trail from the Orange/Lake County line, the town of Killarney and Oakland, the city of Winter Garden, across U.S. 441, through downtown Apopka to Welch Road. Stop and enjoy the butterfly garden at the Tildenville outpost!

207 Mather Smith Drive, Oakland
$730,000
4 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
This custom built home is on the market for the first time and is nestled in the heart of Oakland! Sitting on just under a half acre of land, this delightful property offers a perfect blend of comfort, style, and convenience, making it an ideal place to call home. As you enter this meticulously maintained residence you will be greeted by a spacious living area, perfect for relaxing or entertaining guests. The well-appointed kitchen features modern appliances, sleek stone countertops, and ample storage space, making meal preparation a breeze. This home boasts 4 bedrooms and 2 bathrooms split plan, providing plenty of space for the whole family. The master suite offers a peaceful retreat with a luxurious en-suite bathroom and a walk-in closet, ensuring privacy and comfort. Outside, you'll find a beautifully landscaped yard, ideal for enjoying the Florida sunshine and hosting outdoor gatherings with friends and family. The property also includes a 3-car garage with plenty of storage space and large driveway for your convenience. Located in the desirable Oakland area, this home offers easy access to Oakland Nature Preserve, The West Orange Trail, shopping and dining in nearby Downtown Winter Garden and is close to major roadways, making commuting a breeze. Schedule a showing to see your next home today.

112 W Sadler Avenue, Oakland
$255,000
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Welcome to a promising canvas awaiting your personal touch! This 3 bedroom, 1.5-bathroom home presents a wonderful opportunity for those with a vision for transforming a space into their dream residence. In need of light rehab, this property allows you to infuse your unique style while creating a comfortable and personalized haven.

411 W Hull Avenue, Oakland
$535,000
3 Beds ⋅ 2 Baths ⋅ Hull Island At Oakland SubDv. ⋅ 34760 Zip Code
Welcome to this like-new home in the intimate community of Hull Island. This split floorplan 3 bedroom 2 bathroom home has been lovingly updated. As you step inside through the foyer, you are drawn to the two well-appointed secondary bedrooms, sharing a stylishly designed hall bath at the front of the house. Beautiful wood-look tile spreads throughout the home - no carpet here! The L-shaped kitchen is a culinary enthusiast's dream, featuring an abundance of 42” maple cabinets crowned with modern LED under-cabinet lighting that accentuates the backsplash, and luxurious quartz countertops. Not to mention a gas range! The island provides not only a quick spot for on-the-go meals but also a spacious prep area for the family chef. The generously sized walk-in pantry is your ideal companion for all of those bulk shopping trips. Adjacent to the kitchen, a tech-savvy desk area serves as a versatile hub for sorting mail, charging devices, or exploring your next Pinterest-worthy recipe. The primary suite, tucked away for privacy at the rear of the home, is bathed in natural light through its expansive windows and features an elegant tray ceiling. The deluxe ensuite bath is a sanctuary of comfort, showcasing a dual-sink quartz-topped vanity, an oversized shower adorned with upgraded subway tile and a river rock floor, a semi-frameless enclosure, an enclosed water closet, and a spacious walk-in closet. Step out onto the covered lanai and enjoy the privacy of a fenced-in backyard. Other upgrades include an interior laundry room with a utility sink, blinds on all windows, a tankless gas hot water heater, and an additional pavered area in the backyard. All appliances convey, making this a truly move-in ready home! Hull Island offers a community pool with a cabana area, a bark park, picnic trails, and a viewing dock off of Lake Apopka. Minutes away from downtown Winter Garden, the Florida Turnpike, and walking distance to the West Orange Trail. Schedule your showing today!

1808 Western Trailway Drive, Oakland
$957,000
4 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code
One or more photo(s) has been virtually staged. Price improvement just made on this beautiful property! In the heart of historic Oakland, welcome to the ultimate lakefront living experience with an opportunity to own a beautiful, 4 bedroom, 3 full bath home, on .64 acres, in this quaint town with over 118 feet of waterfront living on Lake Apopka! As you enter the property, when greeted beyond the foyer and 11 foot ceiling line family room, you are immediately swept away with breathtaking views of the 30,000 acre lake, making it the perfect setting for relaxation and entertainment. Imagine yourself enjoying your morning coffee while watching the sunrise on the large 30' x 40' ft deck, with an herb garden and citrus trees close-by, or the oversized dock closer to the water. The lake views are absolutely stunning, with the option to entertain family and friends with a barbecue on the back lawn 16' x 16' covered cabana to also experience the beautiful Florida sunsets. A private boat dock with a Leeson brand lift, measuring 21' x 26', allows immediate lakefront access where you can indulge in your favorite water activities, from wakeboarding, skiing, wake surfing, fishing, body boarding and kayaking, which is ideal for any boater or fishing enthusiast. It's a hidden gem to know that Lake Apopka is part of the Harris Chain of Lakes, which flows through the Apopka-Beauclair Canal with direct access North to the Ocklawah River, which continues through canals and locks that will take you all the way to the Atlantic Ocean in Jacksonville! A new full home 24kw Generac Generator adapting to two 420LP tanks conveys with the property. The oversized garage includes a workshop area. Water Heater and Air Conditioner are within 5 years new. The landscaping on this property is immaculate with a thorough french drain system that handles the irrigation flowing from the lake, which keeps your water bill low. Walking distance to the West Orange Trail and community park with a playground, tennis court and pickle ball court, along with the neighboring Jack Voss Park with its' brand new pier, make this location perfect for your family. It's location is also just a bike or golf cart away to the town schools, and everything fun and beautiful Downtown Winter Garden has to offer, like great restaurants, shops, farmers market, festivals and events! The town is also very close to major interchanges so you’re only 25 min from Downtown Orlando, Disney and Universal! Very low HOA costs, as this is a very small and quaint neighborhood. Don’t miss this rare opportunity and schedule your private showing today! <div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=71roZuXue7S&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div> Bedroom Closet Type: Walk-in Closet (Primary Bedroom).

32 Oakland Pointe Circle, Oakland
$630,000
4 Beds ⋅ 4 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
One or more photo(s) has been virtually staged. Enjoy a beautiful view of Lake Apopka from this lovely house on a corner lot gorgeous, custom-built home in the heart of Downtown Oakland! This home features 4 bedrooms and 3.5 bathrooms. One of the bedrooms can be used as a flexspace for a den, pool table, or media room. The living room has a cozy fireplace and French doors that lead to a covered porch. The AC, ROOF and WATER HEATER were recently replaced. There's a big formal dining room, a welcoming kitchen with a large pantry, and a breakfast area with easy access to the side-entry garage and porch. Unlike many houses nearby with multiple floor levels, this one is all on ONE LEVEN and has a smart layout with two bedrooms on each side. The yard is green and well-kept, and you can relax in the peaceful private yard surrounded by nature. The house has high ceilings, lots of windows, and spacious front and back porches, creating a perfect retreat for those seeking tranquility. Conveniently located just a block from Downtown Oakland, and a short walk, run or bike ride from historic Downtown Winter Garden, along the fabulous 26-Mile West Orange Trail! Located in the golf cart district! Whichever mode of transportation you choose, you are mere minutes from the numerous dining, shopping & entertainment options Downtown Winter Garden provides! Easy access to SR 50, Florida’s Turnpike and SR429/Wekiva Parkway - this home is right in the center of it all!

50 Demens Street, Oakland
$309,000
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
If you are looking for a great starter home, or even a great investment property at an excellent price, in a great location, then look no further! This charming home is located on a corner lot in beautiful Oakland, Florida. The home offers an open floor plan that flows seamlessly from the kitchen to the great room. The kitchen features wood cabinets, laminate countertops, and stainless steel appliances with an adjacent laundry room. There are fans in the bedrooms for extra comfort. The flooring in the home is laminate and ceramic throughout. This property is located just two miles from downtown Winter Garden which offers a variety of shopping, restaurants, breweries and more! The home is located just 2 blocks from the West Orange Trail, half a mile to Lake Apopka access/dock, and 1 mile to the Oakland Nature Preserve! This location also boasts quick access to major roads such as the 429, Florida Turnpike and the 408, making for an easy commute and travel to Orlando and all of Central Florida.

500 W Oakland Avenue, Oakland
$305,000
2 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Welcome to your dream home in the charming community of Oakland, FL! This 2-bedroom, 2-bathroom cottage is a haven of modern comfort, with a newer roof, HVAC, and water heater all installed in 2020. Nestled on a generous, fenced lot, this property offers the perfect backdrop for outdoor gatherings or serene solitude. Step inside to discover a cozy, open floor plan and tastefully updated bathrooms and kitchen that make everyday living a breeze. Conveniently located, you're just minutes away from Oakland's quaint parks, local shopping, and delightful dining options. This home is more than just a place to live—it's a lifestyle.

210 S Pollard Street, Oakland
$769,000
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Small town living in nature-filled Oakland. Bring your golf cart! No HOA!! This 2-story custom home proudly stands on a .27-acre corner lot, just 2 blocks to the 20+ mile West Orange Trail, half a mile to Lake Apopka access/dock, and 1 mile to Oakland Nature Preserve! On days you want a break from exploring Florida’s wild beauty, this magazine-worthy property can accommodate. The 4 bedroom, 3 bathroom floor plan keeps 1 bedroom/bathroom downstairs, while the upstairs holds the primary bedroom/bathroom with dual closets, and 2 secondary bedrooms with a shared bath. The open-concept gathering areas share a gas fireplace for cozy evenings, and the formal but versatile dining room can be transformed to meet any other living space needs. Outdoors, the fenced backyard offers a screen-enclosed porch with outdoor kitchen area, and beyond the screen is another patio area with firepit and 6-person spa, completely open to Florida’s night sky. Over $60K in upgrades have been completed within the past 2 years to ensure an elegant living experience inside and out. Bonus: The oversized garage has room for 2 cars and your golf cart, plus the attic has flooring for storage. This Oakland treasure is located less than a half mile to Speer Park for playground, picnics & tennis. Convenient roadways West Colonial Dr and FL Turnpike are nearby, both which can start your journey to wherever you may need to go. Two miles to downtown Winter Garden with shopping, restaurants, breweries and more! Schedule a showing today!

101 W Oakland Avenue, Oakland
$857,500
4 Beds ⋅ 4 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
THIS is your RARE opportunity to own a slice of old Florida with this gorgeous, custom-built Colonial Revival home in the heart of Downtown Oakland! Conveniently located just a block from Downtown Oakland, and a short walk, run or bike ride from historic Downtown Winter Garden, along the fabulous 26-Mile West Orange Trail! Located in the golf cart district! Whichever mode of transportation you choose, you are mere minutes from the numerous dining, shopping & entertainment options Downtown Winter Garden provides! Checking in at 3,838 square feet of living space and situated on a large 0.29 acre lot framed by amazing, mature oak trees - This custom-built Colonial Revival home is the dictionary definition of CURB APPEAL! You will immediately fall in love with the beautiful brick, full-facade wrap-around front porch. As you enter the home through the stately, double wooden doors, the grand foyer and its lovely staircase opens up to the living room on your right and to your left is the dining room with loads of natural light, beautiful hardwood floors and custom coffered ceiling. From there, you will find a lovely, open kitchen with solid wood 42” cabinetry, a granite preparation island and breakfast nook. The large family room features new carpet and a wood-burning fireplace. Once upstairs, you will find a lovely loft with beautiful hardwood floors, and French doors that lead out to a roomy, relaxing covered patio with new composite decking. The relaxing master bedroom features new carpet, dual walk-in closets and a roomy master bathroom with dual vanities, a relaxing garden bath and a walk-in shower. Bedrooms 2 & 3 are both nicely sized with ample closet space and a shared jack-and-jill bathroom. The expansive bonus room features bamboo flooring, an ensuite bathroom and private stairway access – the perfect space for a second master, home office or guest suite! Additional Features: NEW ROOF installed 2021, New Main AC 2022, Town of Oakland water, Irrigation system utilizes private well, Oversized 2-car garage with built-in storage shelves and lots of natural light. *LOCATED JUST ONE BLOCK from the 26-Mile WEST ORANGE TRAIL! IN THE GOLF CART DISTRICT!* Easy access to SR 50, Florida’s Turnpike and SR429/Wekiva Parkway - this home is right in the center of it all! **Stunning views of 30,000 Acre Lake Apopka (Florida’s 4th largest lake) are just two blocks away at the Jake Voss Pier!** The perfect place for enjoying and observing Florida’s natural wildlife habitat and starting your day with an amazing sunrise or winding down after a busy day watching the sunset. Schedule a showing today before this unique opportunity is gone!

10 Vandermeer Street, Oakland
$65,000
Oakland Town SubDv. ⋅ 34760 Zip Code
PRICE IMPROVEMENT!! Don't let this amazing opportunity pass you by! Your chance to build a dream house on this quiet and very desirable lot in the town of Oakland. Walking distance to playgrounds, park and picnic areas.

528 W Hull Avenue, Oakland
$410,000
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Beautiful oversized corner lot in charming Oakland. Nice open floor plan. Workshop is in the Garage and offers tons of storage. There is no HOA, so bring your boats and RV's to this property that has plenty of room to park/store them. This house has been under renovation, so requires work including a new roof. However, the property offers many possibilities to suit your vision of a dream home.

202 W Oakland Avenue, Oakland