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$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
$2,300,000
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
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
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!

141 Millholland Street, Oakland
$650,000
5 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code
PRICE IMPROVEMENT!! Nestled in between Clermont and Winter Garden, this custom-built, 5-bedroom, 3-bathroom home has over 3,000 square feet! There’s also a 3-car garage, backyard lanai and screened in outdoor grill area that even has a storage area/workshop complete with electricity and lights. Outside you’ll immediately notice the meticulously cared for yard with lush landscaping, mature trees and an irrigation system. The roof and A/C were replaced in 2017, the entire interior has been freshly painted and the carpets have been steam cleaned. Once inside, there’s a large formal dining room with chandelier as well as a formal living room. This unique split floor plan features an oversized master bedroom with a walk-in closet, ensuite bathroom with dual sinks, a garden tub and separate handicapped accessible shower. The other side of the house has 3 more bedrooms that share a hallway bathroom. Upstairs there’s an enormous private loft bedroom with an ensuite bathroom and walk-in closet. There are extra cabinets scattered throughout the house for even more storage space. The kitchen features an island, an eat-in area with plenty of room for a big table, large pantry and plenty of cabinet and counter space for easy entertaining. The kitchen opens to the great room with vaulted ceilings, creating one massive space for living. There’s a laundry room right off the kitchen with plenty of under the staircase storage. Oakland still has that small town feel where residents can enjoy Speer Park and the Jack Voss Park fishing pier. The park has basketball, tennis and pickleball courts, a sizeable playground, lots of majestic shade trees and a gazebo. You can ride your bike to the West Orange Trail near the Arts and Heritage Center or take a short ride to the Killarney Station Trailhead. The Oakland Nature Preserve is also nearby and offers visitors a close-up look at nature and special events throughout the year. Right around the corner is historic downtown Winter Garden with its one-of-a-kind shops, restaurants and farmer’s market. And a short drive will bring you to Clermont with their state-of-the-art medical facilities, an abundance of shopping, grocery stores, restaurants, golf courses and more! The Florida Turnpike interchange is in Oakland, making for a short drive to the airport, attractions and all that Orlando has to offer. Make your appointment now to see this amazing house before it is gone!

8 Oakland Pointe Cir, Oakland
$700,000
4 Beds ⋅ 3 Baths ⋅ Town Of Oakland SubDv. ⋅ 34760 Zip Code
NO HOA | Golf cart district | 624 sqft ADU | 1-block from WEST ORANGE TRAIL | walking distance Speer Park | Blocks away from Lake Apopka. Welcome to this charming 4 bed 3 bath WITH GUEST SUITE WITH FULL KITCHEN, BATHROOM, WASHER AND DRYER (additional 624 sqft of living space) ranch-style home in the heart of historic Oakland, ideally located on a spacious corner lot in the highly desired Golf Cart District. Under the majestic canopy oak trees, this 2,282 sqft home offers the perfect Florida lifestyle with a great sense of community with NO HOA. Just a few blocks away from the West Orange Trail, Lake Apopka's dock, pickleball courts, and Spear Park, outdoor activities are right at your doorstep. Inside, the open and spacious layout, this well-designed floor plan features a cozy living room, a dedicated office space, and a kitchen perfect for large gatherings. One of the home's UNIQUE FEATURES is the above the garage GUEST SUITE. Complete with its own private bathroom, kitchenette, washer and dryer, and a separate entrance. Perfect for guests, in-laws, private workspace or man cave! Oakland’s downtown area retains its historical charm with preserved buildings and a community-centric layout. The town has a rich history from the late 19th century and maintains its small-town feel. Nearby, the Oakland Nature Preserve offers walking trails, educational programs, and lovely views of Lake Apopka. Hop on your golf cart and you’re minutes away from Historic Downtown Winter Garden, full of restaurants, shops, an award-winning farmers market, and tons of family activities. This home is also 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 this awesome opportunity to own a piece of paradise in a prime location. Schedule your private showing today and see for yourself!

305 Briley Ave, Oakland
$575,000
3 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Discover the charm of this custom-built home, completed in 2020, with no HOA! Situated just minutes from downtown Winter Garden, this stunning, four-year-old residence is ready to welcome you. Featuring 3 spacious bedrooms, 2.5 bathrooms, an office, and a generous loft, this home is thoughtfully designed with premium features throughout; including electrical plug in the front yard that can be used to charge Electric Vehicles! Step onto the expansive front porch and into the inviting entryway, showcasing a glass staircase railing, luxury vinyl flooring, and an open view of the main living area. To your immediate right, you'll find a half bath and an office with custom glass doors, perfect for use as a guest room, playroom, or TV room. The kitchen is a chef’s delight with a gas stove and an oversized island adorned with custom lighting. Adjacent to the kitchen is a mudroom leading to a large laundry room, and access to the side entry and extended driveway. The kitchen opens to a spacious family room that connects to the primary bedroom, featuring French doors to a private deck. The primary bathroom offers double sinks, a walk-in shower, and a custom closet with a barn door that is sure to impress. From the family room, large tandem sliding doors lead to an amazing outdoor space perfect for entertaining. The oversized patio, with wood wall and ceiling, is prepped for a summer kitchen and offers covered access to the garage and fenced-in long driveway. Upstairs, you'll find 2 additional large bedrooms and an oversized loft with a wood beam ceiling, along with a hookup for a stackable washer and dryer! Conveniently located near the turnpike and within close proximity to all that Winter Garden has to offer, such as Downtown Winter Garden and its famously known for Farmers Market, Winter Garden Trail, shopping, dining, and entertainment. In addition to great public schools, this home is also near the TOP rated Oakland Avenue Charter School while enjoying quick access to the 429, 408, and the Turnpike. This home has it all and a must-see! Don’t miss out on this exceptional opportunity and schedule your showing today!

306 W Hull Avenue, Oakland
$619,000
3 Beds ⋅ 2 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code
***New Price - Plus a Seller concession available to Buyer at closing***. This well-maintained, custom built split floorplan, home boasts pride of ownership. As you enter the property, you will be greeted by the lush lawn and mature landscaping. As you enter the home, the foyer leads you directly into the open great room with French doors accessing the expansive Florida room. Beyond the Florida room, the fully fenced backyard with mature trees offers a tranquil and private green space. The kitchen features custom oak cabinets, breakfast bar, dining area along with an adjacent dining room creating an ideal space for entertaining or large family gatherings. The 9’ ceilings, crown moldings, 5” baseboards, custom blinds and oak wood floors throughout the home are just a few of the custom touches you’ll notice. The spacious primary bedroom with ensuite features a garden tub and dual walk-in closets. The oversized garage has epoxy flooring and includes a workshop area, room for golf cart parking and a rear entrance garage door that leads to the covered outdoor patio perfect for grilling or an outdoor kitchen. There is also an air-conditioned flex space with a built-in desk and shelving perfect for an office or crafting room. New roof in 2023, new cypress fence in 2023, newer air conditioner. This home is in the Oakland Pointe community, nestled among majestic live oaks and dirt roads, in the heart of historic old town Oakland, located on the south shore of Lake Apopka. This home is within walking distance to the quaint Town Center, the West Orange Trail, the community park with a playground, tennis, pickle ball and basketball courts, along with the neighboring Jack Voss Park with a brand- new pier, making this location perfect for your family. The golf cart friendly area allows for a quick ride to all the fun Downtown Winter Garden Entertainment District has to offer, like great restaurants, shops, farmers market, festivals, events and just minutes to the Oakland Nature Preserve and more! The town of Oakland is conveniently located to all the major interchanges, only 25 min from Downtown Orlando, quick access to all the major attractions as well as multiple world-famous Florida beaches.

15 Oakland Pointe Circle, 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
$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