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4 Beds ⋅ 3 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code

Custom Entertainer’s Dream Courtyard Home, Welcome to the charming town of Oakland, Florida—just minutes from the Florida Turnpike, Johns Lake, new hospitals, top dining options, and the convenience of the new Costco. This beautifully designed custom residence is situated on an oversized corner lot, featuring a private, screen-enclosed pool that offers comfort, functionality, and luxury living. From the moment you arrive, you’ll be captivated by the circular driveway with dual entrances, mature shade trees, and the impressive side-entry garage. Step inside to discover an open, light-filled floor plan with abundant windows and large sliding doors that seamlessly connect indoor and outdoor living spaces. Modern upgrades continue throughout the home, including three HVAC units—including new systems in 2024 and 2025, a 2022 water heater, energy-efficient construction with ICF (Insulated Concrete Forms), double-pane windows and sliders, and spray foam insulation in the attic. Other updates include a new roof (2024), fresh interior paint and pool deck paint (2025), and remodeled kitchens and bathrooms. The foyer leads to spacious formal living and dining areas, each with views of the expansive screened patio—ideal for entertaining. The chef’s kitchen boasts stone countertops, modern cabinetry with illuminated uppers, built-in ovens, a cooktop, undermount lighting, an outdoor vent system, a corner pantry, and a picturesque window over the sink. It overlooks the sunny dinette, soaring two-story family room with a cozy fireplace, and a striking wood staircase with wrought iron railings. Designed with a split-bedroom layout, each of the four bedrooms offers ensuite bath access. The 1st floor primary suite is a private retreat, featuring high ceilings, wood floors, patio/pool access, and a two-sided gas fireplace that enhances the bedroom and private bath. The ensuite includes a soaking tub, separate glass-enclosed shower, dual vanities, linen closet, water closet, and a spacious walk-in closet. The 2-story family room is delightful, featuring a fireplace, high ceilings, and multiple windows that provide ample natural light. Adjacent to the family room is the spacious dinette. Two double-pane sliding doors lead to the covered patio, where you can enjoy the fenced backyard, which includes a fire pit. Down the hall is another bedroom suite with a remodeled bath, a full-size laundry room, and garage access. Upstairs, you’ll find two additional bedrooms—one with a private balcony overlooking the corner park—and a bonus room with its own balcony view of the pool. Each room shares another jack-and-jill full bath with separate vanities. The backyard is a true Florida oasis—fully fenced with pavers for a clean look, a large screened-in pool area, and ample space for pets and play. With direct access to the popular West Orange Trail, outdoor adventures are just steps away. This exceptional home combines location, design, and functionality—perfect for visiting relatives and entertaining. Don’t miss your chance to own this one-of-a-kind property in one of Central Florida’s most desirable communities.

100 Demens Street, Oakland

4 Beds ⋅ 3 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code

** Ask your lender about RATE BUY DOWN options. Did you know some lenders have minimal closing costs? Inquire for more information. ** Discover the beauty of lakefront living on the shores of Lake Apopka with this 4-bedroom, 3-bath, 3 CAR garage home with an air-conditioned BONUS space (~ 400 sqft) over the garage. Lake Apopka is the headwaters of the Ocklawaha Chain of Lakes, which connects to Lake Beauclair, Lake Dora, Lake Harris, Lake Griffin and the St Johns River. This waterway system allows boaters to travel from Lake Apopka all the way to the Atlantic Ocean via the St. Johns River, making it one of Florida’s most interconnected lake chains. Boasting expansive water views and stunning sunsets, this property offers a rare opportunity to create your dream waterfront oasis. Inside, you’ll find a spacious layout with an abundance of natural light, spacious living areas, and a primary suite with serene lake views. While the home needs some updating, the solid structure and unbeatable location provide the perfect canvas for customization. As you enter the home you’ll be captivated by the views. On the east side you’ll find the generously sized PRIMARY SUITE, which includes a garden tub, dual sinks, shower, walk-in closet, and FRENCH doors that lead to the screened-in patio. Adjacent to the primary suite is another bedroom and full bath. The 2nd bath also connects to the patio. On the west side of the home are two additional bedrooms, one full bath, and a spacious laundry room with utility sink. The kitchen, which includes stainless steel appliances, opens to the family room, eat-in kitchen area, and the breathtaking and elevated lake views. A separate formal dining space is carved out in the home which makes entertaining a breeze. The property has plenty of room for a pool should you desire to build a backyard oasis. Relax and unwind on the screened-in patio or stroll to the DOCK for an evening sunset cruise. 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 & basketball courts, & picnic areas. Conveniently located near the Turnpike, East-West Expressway, 429, grocery shopping, theme parks, & golf courses, this home offers a lifestyle of unparalleled beauty & convenience. Embrace the enchanting Oakland-Winter Garden lifestyle & make this exquisite residence your next place to live!

111 Millholland Street, Oakland

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

5 Beds ⋅ 5 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Looking for a bit of Oakland History - NOW available 525 N Tubb! Property includes the main house, an apartment and a workshop. The house is a 3500 square foot home with three bedrooms, three baths, powder bathroom, large kitchen, large living room, dining room and much more. There are ten-foot ceilings throughout, and all appliances remain. Attached to the main house is a screened breeze way, a two-car garage, a 1300 square foot workshop and storage room. An amazing feature of this house is a 629 square foot apartment with a two-car carport and deck. This attached area can be a rental or an in-law suite. This circa 100-year-old home sits on 3/4 acre filled with various fruit and flowering trees and shrubs and giant oaks. The wiring, plumbing has been updated and the roof replaced in March of 2020.

525 N Tubb Street, Oakland

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

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