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$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
$85,000
2 Beds ⋅ 1 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
**8MULTIPLE OFFERS***The asset manager has requested a 'HIGHEST AND BEST' response from the outstanding buyer(s) for the following property: 537 WEST HERRIOTT AVENUE, OAKLAND, FL 34760 BY 3:00 PM October 2,2024*** Quarter of an acre ,end of the street lot close to Downtown Winter Garden walking distance to the neighborhood Park . There is a structure in the lot that might need removal to build your dream home here. ***No access to the structure***

537 W Herriott Avenue, Oakland
$285,000
3 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Nestled in the quaint Town of Oakland enjoy this 3 bedroom 2 bath home on a quiet street with oversized lot. Home offers a new roof 8/2024, HVAC 3/2024, and a hot water heater in 8/2024. Interior remodeled with new drywall, engineered hardwood flooring, fixtures and new doors. Home is close to Oakland Nature Preserve, West Orange Trail, Oakland Farmers Market, and the public park.

527 W Herriott Avenue, 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
$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
$365,000
3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
One or more photo(s) has been virtually staged. Welcome to beautiful 524 W Oakland, a charming updated home nestled in the heart of Oakland, FL! You'll be delighted by this 3-bedroom, 1.5-bathroom home on an OVERSIZED PRIVATE Lot that is perfectly positioned just minutes from the vibrant Historic Downtown Winter Garden and along the scenic W Orange Trail, where you have immediate access to the Oakland Nature Preserve, Lake Apopka & more! This location is one of a kind! Inside you will discover a fresh and inviting interior featuring new flooring and windows throughout. The open living area is ideal for both relaxation and entertaining. The spacious primary bedroom boasts a walk-in closet for your convenience and En-Suite Bath. A large bonus room off the kitchen offers endless possibilities—perfect as a family room, home office, or bedroom. Additional highlights include an inside laundry area and an oversized corner lot that provides ample space for outdoor enjoyment and potential expansion. Don’t miss your chance to own this lovely home in a serene yet conveniently located neighborhood just 30 minutes from the Airport & 30 minutes from Disney! Schedule a showing today!

524 W Oakland Avenue, 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
$261,000
2 Beds ⋅ 1 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Welcome to this beautifully renovated 2-bedroom, 1-bathroom home at 412 W Herriot Ave, Oakland, FL. With 1,015 sq ft of modern living space, this home has been completely updated. As you enter, you'll notice the spacious open living area, perfect for gatherings and everyday living. The modern kitchen features new stainless steel appliances, elegant countertops, and custom cabinetry. Both bedrooms are comfortable with ample natural light and closet space. The stylish bathroom has been fully updated with modern fixtures, a chic vanity, and a luxurious tub/shower combo. This home also includes energy-efficient upgrades like new windows and a central air conditioning system, ensuring comfort and savings on energy costs. Situated in a quiet neighborhood, it's conveniently close to schools, parks, and shopping centers, with easy access to major highways.

412 W Herriott Avenue, 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
$1,696,482
5 Beds ⋅ 5 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Custom Home Sold Off Market.

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

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

1808 Western Trailway Drive, Oakland
$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
$305,000
2 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Welcome to your dream home in the charming community of Oakland, FL! This 2-bedroom, 2-bathroom cottage is a haven of modern comfort, with a newer roof, HVAC, and water heater all installed in 2020. Nestled on a generous, fenced lot, this property offers the perfect backdrop for outdoor gatherings or serene solitude. Step inside to discover a cozy, open floor plan and tastefully updated bathrooms and kitchen that make everyday living a breeze. Conveniently located, you're just minutes away from Oakland's quaint parks, local shopping, and delightful dining options. This home is more than just a place to live—it's a lifestyle.

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

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

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

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

202 W Oakland Avenue, Oakland