34760 Zip Code FL 2 Car Garage Real Estate, Homes for Sale

5 Beds ⋅ 8 Baths ⋅ Grove/Oakland SubDv. ⋅ 34760 Zip Code

Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers an extraordinary standard of luxury estate living. Every detail speaks to a level of craftsmanship and thoughtfulness that simply cannot be replicated. Five generously sized bedrooms, each with its own private ensuite bath, provides unmatched comfort and privacy for family and guests alike. Two additional powder baths serve the main living areas, while a dedicated pool bath keeps the outdoor experience seamless. At the heart of the home, a dramatic double island kitchen commands attention — equal parts showpiece and hardworking hub — crowned by soaring coffered ceilings that lend architectural depth and timeless elegance throughout. Step outside to your own private resort, where a sparkling pool and spa, summer kitchen, and covered lanai with roll-down screens create the ultimate Florida lifestyle — open-air breezes or a fully enclosed retreat, all at the touch of a button. Beyond your front door, The Grove places you steps from The Harvest District's boutique shops and restaurants, with exclusive access to the resort amenities at nearby Briley Farm — all reachable by foot or golf cart.

1134 Prado Lane, 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

$2,395,000

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, and a spacious loft across 3,712 square feet of elegantly curated living space—where classic design meets modern sophistication in the main house. Enhancing both versatility and privacy, the property also includes a beautifully appointed 785 square foot garage casita with its own private entrance, complete with a living room, kitchenette, bedroom, and full bathroom—ideal for guests, multigenerational living, or a private home office retreat. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1137 Prado Lane, Oakland

$2,045,357

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Nestled within the exclusive Grove community in the heart of Oakland and Winter Garden's coveted golf cart district, this bespoke pre-construction residence is a rare opportunity to own something truly one-of-a-kind. Five bedrooms, five full bathrooms, a powder room, and a gracious loft unfold across 3,725 square feet of living space where timeless architecture and modern sophistication coexist effortlessly — every detail considered, every finish deliberate. Element Home Builders has built its reputation on craftsmanship that doesn't cut corners and design that doesn't follow trends — because the Clementine wasn't designed to be fashionable. It was designed to be unforgettable. Step outside and you're two minutes from the West Orange Trail and just a short golf cart ride from the vibrant energy of Downtown Winter Garden — boutique shopping, acclaimed dining, weekend farmers markets, and the kind of small-town charm that's increasingly impossible to find this close to the city. This isn't just a home. It's a lifestyle you'll never want to leave.

1225 Water Maple Drive, Oakland

$629,999

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current market conditions, this property presents an excellent opportunity for buyers seeking newer construction without delays or renovation needs. A compelling option for buyers looking for value, condition, and immediate occupancy.

38 S Pollard Street, Oakland

$1,949,000

5 Beds ⋅ 5 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code

Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space. Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy layout. The main living areas seamlessly blend together, creating the perfect setting for entertaining, with a spacious great room flowing into a designer kitchen complete with a large island, walk-in pantry, and premium finishes. The primary suite, conveniently located on the main level, offers a private retreat with a spa-inspired bathroom and generous walk-in closet. Upstairs, you’ll find additional bedrooms along with a versatile loft space ideal for a media room, office, or play area. Designed for the Florida lifestyle, the outdoor living space is truly exceptional. Enjoy a resort-style pool and spa, expansive lanai, and dedicated firepit area—perfect for relaxing or hosting gatherings year-round. Additional highlights include a two-car garage with a separate golf cart bay, high ceilings, and thoughtful architectural details throughout. This is a rare opportunity to own a beautifully crafted home in one of the area’s most desirable communities.

511 Briley Avenue, Oakland

$683,000

3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

Beautifully renovated pool home in the desirable Town of Oakland, within the golf cart district, and no HOA. Located in an area seeing significant growth with nearby luxury new construction and vacant lots selling for a premium, this property offers both charm and long-term value in one of West Orange County’s most sought-after locations. This updated single-story ranch home features a bright, open layout with the kitchen flowing seamlessly into the living room. The renovated kitchen includes quartz countertops, updated cabinetry, and a large island with eat-in seating, creating a great space for everyday living and entertaining. The living room is warm and inviting with a wood-burning fireplace and plenty of natural light. Recent improvements include a new kitchen, updated bathrooms, new flooring, new windows, interior and exterior paint, gutters, and a resurfaced pool and paver pool deck. A spacious enclosed Florida room with large windows and a slider that overlooks the backyard and pool, providing additional living space filled with natural light. The home also features a very large indoor utility room that could easily function as a home office, flex space, or additional storage. Outside, you’ll find a large in-ground pool and a fully fenced backyard, perfect for relaxing or entertaining. Located just minutes from downtown Oakland, the West Orange Trail, and Plant Street in downtown Winter Garden, offering easy access to restaurants, shops, and community events. Updated pool homes with no hoa in this area are very rare.

310 E Gulley Avenue, Oakland

$1,975,000

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1106 Sarah Mathews Drive, Oakland

$450,000

3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space. Inside, enjoy a warm and functional layout with 1,419 sq ft of living space and central heating and cooling. The living room is perfect for relaxing evenings by the fire, while the outdoor area is built for Florida living—splash in the pool or unwind under the shade of the trees. Located just minutes from downtown Winter Garden and the West Orange Trail, you’ll love the peaceful setting with quick access to local shops, restaurants, and parks.

310 E Gulley Avenue, Oakland

$950,000

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

$795,000

4 Beds ⋅ 3 Baths ⋅ Town Of Oakland SubDv. ⋅ 34760 Zip Code

Experience the charm of Oakland living in this beautifully updated custom built home located in the heart of town—just minutes to Downtown Winter Garden, Plant Street Market, the West Orange Trail, the Lake Apopka boat ramp/dock and so much more! This move-in ready home is situated on a .27-acre corner lot with no HOA. When entering this 4-bedroom, 3-bathroom home, you’re welcomed by a spacious front patio, beautiful foyer and open floor plan, perfect for entertaining. The flex space to the left of the front entryway offers a great space for an office, secondary dining area or den. The living room overlooks the breathtaking kitchen and exterior screened in patio with beautiful views of the private backyard. The downstairs bedroom and full bath offer flexibility, while the spacious upstairs includes a stunning primary suite with dual closets, and an en suite bath. There are two additional bedrooms upstairs with a shared Jack and Jill bathroom, as well as, a large laundry room with a stackable washer & dryer, sink and plenty of cabinet and countertop space. This home boasts countless updates throughout, including, but not limited to, New Taj Mahal quartzite countertops + backsplash (2024), brand new kitchen sink, hardware and faucet (2024), High end appliances and a brand new gas stove (2025) perfect for the chef at heart! The office features new custom built-in shelving (2024), and the entire interior has been freshly painted (2024). Stylish new fixtures, mirrors, and an updated fireplace façade add to the elegant aesthetic (2024). Move in stress free with upgrades such as a Newer Metal Roof (2022), Shingle Roof (2014), consistent servicing of the HVAC system, Double-Pane Windows throughout and new Plumbing & Electric (2014). Enjoy Florida living in your gorgeous backyard oasis—complete with new sod (2024), lush landscaping, a paver patio, hot tub, and a spacious screen-enclosed brick paver patio with an outdoor kitchen area. This home is truly turn-key and perfectly positioned for nature lovers, golf cart enthusiasts and downtown living alike. Don’t miss this rare opportunity to own this wonderful home in the sought-after Oakland neighborhood—schedule your private showing today!

101 W Oakland Avenue, Oakland

$571,000

3 Beds ⋅ 2 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code

Located in the heart of Downtown Oakland, this well-built and meticulously maintained CBS construction ranch house offers a perfect blend of comfort, style, and convenience. Located on a spacious corner lot, under heritage oak trees, the home features an open and airy split floor plan with high ceilings and sky lights, creating a bright and inviting atmosphere. With numerous updates and renovations, to its roof, double pane, windows, wood flooring, fully renovated kitchen and primary bathroom with steam shower, PVC shutters, fresh interior, and exterior paint, HVAC system and more, ensure a move-in-ready experience. Living in Oakland is like stepping back in time to a more relaxed Florida lifestyle, where canopy tree-lined streets, historic charm, and a strong sense of community create a peaceful setting to call home. Just a short walk to the Lake Apopka pier and one block from the West Orange Trail, along with the Oakland Nature Preserve, .8 miles away, it offers endless outdoor activities. Plus, it’s only minutes from Historic Downtown Winter Garden, Oakland’s sister city, known as the area’s hub for entertainment, dining, shopping, the famed farmers market, a local brewery, and a thriving business district. This prime location catty-corner from Oakland's Speer Park, with tennis, pickle ball and BB courts and playground, this home is a rare find, offering both small-town charm and modern conveniences nearby!

201 Briley Avenue, Oakland

$865,000

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

First Buyer Failed to Close. This is YOUR opportunity. BACK-UP Offers are ENCOURAGED! *** 2.25% ASSUMABLE rate is available for a Buyer! *** NEW ROOF will be installed prior to closing with negotiated offer. 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!

70 Millholland Street, Oakland

$600,000

3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

This home has been beautifully remodeled with a warm, cozy mid-century modern feel. This 3 bedroom, 2 bath home boasts many amazing upgrades including luxury vinyl flooring through out.You will find solid wood cabinets, solid surface countertops, and premium tile in both the Kitchen and the bathrooms. Modern light fixtures and plantation shutters add the perfect touch to this recently painted interior. The block exterior was refurbished with concrete siding and custom wood detail. A new garage was built this year keeping with the mid-century look. The pitched roof was designed for extra storage above the 2 car bay. Enjoy gazing at your own fruit trees in this quiet,quaint town from the covered front porch or the wrap around back deck with gazebo. This home sits on a .25 acre newly custom frenced lot and is close to the West Orange Trail. Oakland is a golf cart friendlytown with access to Winter Garden's Historical Downtown. This turn-key home is a must see for anyone looking for the charm of old Oakland.

418 E Gulley Avenue, Oakland

$570,000

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

$510,000

3 Beds ⋅ 2 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code

Homes to market in OAKLAND are a RARITY! This exquisite one-story residence is a true gem, nestled on a substantial 0.29-acre CORNER lot. Located mere steps from the FISHING PIER on Lake Apopka, Speer Park, the Town Center, and the 22-mile West Orange Trail, this property offers unparalleled convenience and charm. Enjoy leisurely evening strolls or a GOLF CART ride to downtown Winter Garden. As you enter this elegant home, you are welcomed by an expansive living room bathed in natural light, offering partial WATER views of Lake Apopka and serene views of the lush backyard and butterfly garden. The thoughtfully designed split floor plan ensures privacy and functionality, featuring 3 bedrooms, 2 baths, a dining area, a kitchen with updated appliances and an eat-in space, an inviting living room, an interior laundry room with ample storage, a covered patio off the living room, a wrap-around front porch with a cozy swing, and a two-car garage. The generously sized primary suite is a sanctuary of comfort, boasting two closets (including a walk-in), a sitting area or potential office space, FRENCH DOORS leading to the side yard, and a recently updated, spa-like bathroom. The luxurious primary bath includes dual sinks, QUARTZ countertops, a garden tub, a shower, and a walk-in closet. Just outside the primary suite, envision creating a delightful paver patio or a pergola with a garden. On the opposite side of the home, you will find two additional bedrooms, one of which features a spacious walk-in closet (~5X8), as well as a full bath with a tub. The home has a warm and inviting ambiance throughout. With a touch of love and vision, this property holds endless possibilities for transformation into your dream home. The exterior of the home provides a wrap around front porch with swing, a covered back patio, and mature landscaping, along with a lime, avocado, papaya, and citrus tree. Recent updates include a new roof (2023), AC handler, kitchen appliances, a fully remodeled primary bath, and updated plumbing (2019). The Oakland Pointe community, composed of 31 homes, is nestled among majestic live oaks in the historic heart of Oakland and boasts a low HOA fee of $420 per year. Enjoy proximity to the Town Center, the West Orange Trail, Speer Park's playgrounds, tennis and pickleball courts, basketball courts, and picnic areas, as well as stunning sunsets from the fishing pier on Lake Apopka. The bi-weekly Farmers Market, local coffee shop, and the Yoga on the Porch-Summer Series at the Healthy West Orange Arts and Heritage Center add to the community's charm. Just a mere 10-minute drive away to downtown Winter Garden, you will find outdoor dining, festivals, a splash park, theater, brewery, Farmers Market, and much more. Conveniently located near the Turnpike, East-West Expressway, grocery shopping, dining, theme parks, and golf courses, this home offers a lifestyle of unparalleled beauty and convenience. Embrace the enchanting Oakland lifestyle and make this exquisite residence your next place to live!

2 Oakland Pointe Circle, 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

$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

$652,000

4 Beds ⋅ 2 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code

****MULTIPLE OFFERS....HIGHEST & BEST BY 5/6/2024 BY 2PM**** Welcome to this beautifully renovated 4-bedroom, 2-full bath home located at 200 Mather Smith Dr in the charming town of Oakland, Florida with NO HOA!! This stunning property has been completely transformed and boasts exquisite upgrades throughout. As you step inside, you'll be greeted by the spacious and open floor plan that seamlessly connects the living, dining, and kitchen areas. The tastefully designed kitchen features modern stainless-steel appliances, custom cabinetry, sleek countertops, and ample storage space, making it a chef's dream. The four bedrooms are generously sized and offer plenty of natural light, creating a serene and inviting atmosphere. The bathrooms have been meticulously upgraded with stylish fixtures and finishes, providing a spa-like experience. The huge backyard includes a large patio that is perfect for entertaining friends & family and a shed with shelving for plenty of storage. The 2-car garage has new paint, epoxy floor, and wooden storage shelves. This home is the perfect location for outdoor enthusiasts and those seeking the vibrant downtown Oakland experience & events. Situated just steps away from the West Orange Trail, you'll have easy access to miles of scenic biking, walking, and jogging paths in addition you will be walkable to Oakland Avenue Charter School Golf cart path to Downtown Winter Garden where you can explore the vibrant shops, boutiques, and restaurants, or take part in the various community events and festivals held throughout the year. Schedule a showing today and envision yourself living in this renovated gem!

200 Mather Smith Drive, Oakland

$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

$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

$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

$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

34760 Zip Code 2 Car Garage Real Estate & Homes

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