34760 Zip Code FL Real Estate, Homes with Family Room for Sale

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

$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

$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

$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

34760 Zip Code Real Estate & Homes with Family Room

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